32751 Zip Code FL Lake Front Real Estate, Homes for Sale

3 Beds ⋅ 1 Baths ⋅ Osborne Manor SubDv. ⋅ 32751 Zip Code

This is a once in a lifetime opportunity to lovingly restore one of Maitland's oldest, historic homes, built in 1886, or choose to build your own dream home on this almost half an acre lot. It is situated in the prime location of the Maitland/Winter Park area; steps from beautiful Lake Sybelia. Most of the million-dollar homes in the neighborhood have recently been rebuilt. When you take a walk inside; you will be taken back to early Florida; with the wrap around wood porch, original windows, hardwood floors and high ceilings. There is so much character in this home! There is also a guest cottage out back that could be restored as well. This home and lot are in a very sought-after location and neighborhood, surrounded by beautifully appointed redone, large homes all around Lake Sybelia. This is a unique opportunity no matter what you as the buyer choose; restore or build in one of the prettiest neighborhoods and locations in Central Florida.

251 W Horatio Avenue, Maitland

$969,000

4 Beds ⋅ 3 Baths ⋅ Druid Isle SubDv. ⋅ 32751 Zip Code

Welcome to your private lakefront retreat on one of Maitland's most coveted streets—Druid Isle. Tucked away on a quiet peninsula surrounded by water on every side, this exclusive one-way-in, one-way-out street offers an unmatched sense of privacy and tranquility. Situated at the end of the cul-de-sac, this beautifully updated 4-bedroom, 3-bathroom pool home combines modern finishes with an incredible waterfront lifestyle. Inside, you'll find a bright, open floor plan featuring brand-new luxury vinyl flooring throughout, fresh interior paint, and thoughtfully updated spaces designed for both everyday living and entertaining. Every detail has been carefully refreshed, making this home completely move-in ready. Step outside to your own private oasis where a sparkling pool overlooks the water, creating the perfect setting for relaxing or hosting family and friends. The exterior has been transformed with all-new professional landscaping, a brand-new paver driveway, and a newly paved walkway leading to a dedicated fire pit area—an ideal place to gather and enjoy breathtaking sunsets over the lake. Whether you're looking for peaceful waterfront living, exceptional privacy, or a home that's been completely updated from top to bottom, this Druid Isle gem offers a rare opportunity to own one of Maitland's most desirable lakefront properties. Experience the beauty, serenity, and lifestyle that only Druid Isle can provide. ROOF - 2017 HOT WATER HEATER - 2026 AC - 2012 PLUMBING - Updated 2018 ELECTRICAL - Updated 2018

1301 Druid Isle Road, Maitland

$825,000

4 Beds ⋅ 2 Baths ⋅ Dommerich Estates 2nd Add SubDv. ⋅ 32751 Zip Code

Under contract-accepting backup offers. Beautifully updated pool home in the highly sought-after Dommerich Estates! This spacious 4 bedroom, 2 bath residence offers 2,061 square feet of thoughtfully designed living space and located one block from deeded lake access to the Winter Park Chain of Lakes. The lake lot includes a boat ramp, pier for relaxing or fishing and a storage rack for kayaks and canoes! Recent updates include a New Roof (2026), New HVAC system (2026), Water Heater (2022), Newly updated bathrooms, New interior doors, frames and baseboards, beautiful luxury vinyl plank flooring, New gutters, New pool screen enclosure and updated landscaping! The versatile floor plan includes formal living and dining areas, along with a generous family room complete with custom built-in shelving and picturesque views of the sparkling pool. French doors open to a screened lanai with a private pool, heated spa, and outdoor shower, perfect for relaxing or entertaining year-round. The stunning kitchen is a true centerpiece, featuring quartzite countertops, a farmhouse sink, marble backsplash, GE profile stainless steel appliances, and abundant cabinetry for exceptional storage. The oversized laundry room includes a washer, dryer, extra refrigerator, and even more storage. The split-bedroom layout provides added privacy. The primary bedroom is complete with an updated ensuite bath with a stunning glassed shower with designer tile. The guest bedrooms share an updated bath with dual sinks and tub with stunning tile. The 4th bedroom is ideal for a home office with built in cabinetry. Gorgeous light fixtures and windows adorned with wooden shutters add to the beauty of the home. Ideally located a few blocks to top-rated Dommerich Elementary and Maitland Middle School, as well as Maitland Community Park, where you'll enjoy tennis courts, basketball courts, playgrounds, and scenic walking and jogging trails. This exceptional home combines an unbeatable location, outstanding updates, and access to one of Central Florida's most desirable neighborhoods.

1633 Choctaw Trail, Maitland

$699,000

3 Beds ⋅ 2 Baths ⋅ Dommerich Estates 1st Add Maitland SubDv. ⋅ 32751 Zip Code

**BOATING/LAKE ACCESS** Welcome to 553 Arapaho Trail, where timeless MID-CENTURY CHARM meets thoughtful modern living in the highly sought-after DOMMERICH ESTATES community of Maitland. Offering OVER 1,500 SQUARE FEET of beautifully maintained living space, this 3-BEDROOM, 2-BATHROOM HOME features a desirable SPLIT FLOOR PLAN designed for both privacy and everyday comfort. From the moment you arrive, you'll appreciate the exceptional curb appeal with LUSH, MATURE LANDSCAPING, a NEWLY PAINTED EXTERIOR, and an EXTRA-WIDE, EXTRA-LONG BRICK PAVER DRIVEWAY with room for up to SIX VEHICLES. Inside, the home's original character has been carefully preserved while incorporating today's most important updates, including a NEW ROOF (2025), NEW GUTTERS, WHOLE-HOUSE REPIPE, ELECTRICAL UPGRADES, HARDWOOD FLOORING THROUGHOUT, NEW KITCHEN APPLIANCES, an UPGRADED PRIMARY EN-SUITE, stylish UPDATED LIGHTING FIXTURES, an EXTENDED ATTIC WITH ABUNDANT STORAGE, and a PAINTED GARAGE FLOOR. One of the neighborhood's rare homes with BURIED ELECTRICAL SERVICE, the property also offers a cleaner streetscape and added peace of mind. Step outside and discover your own private backyard retreat featuring an INCREDIBLE SCREENED-IN POOL, an expansive BRICK PAVER POOL DECK, and a charming BRICK PAVER GARDEN WALKWAY winding through beautifully landscaped grounds—perfect for entertaining or relaxing year-round. Beyond the home, DOMMERICH ESTATES continues to impress with its welcoming sense of community and location within one of Central Florida's most desirable school districts, originally designed around A-RATED SCHOOLS to make walking and biking to class safe and convenient. Residents also enjoy access to a VOLUNTARY, LOW-COST HOA that includes a PRIVATE BOAT RAMP to the WINTER PARK CHAIN OF LAKES, opening the door to BOATING, PADDLEBOARDING, FISHING, and unforgettable days on the water. The CITY OF MAITLAND offers the perfect balance of convenience and charm with its WALKABLE NEIGHBORHOODS, beautiful parks, local festivals, downtown concerts, and community events, while world-renowned PARK AVENUE in Winter Park is just minutes away for AWARD-WINNING DINING, BOUTIQUE SHOPPING, ART GALLERIES, and weekend brunch. This is more than just a home—it's an opportunity to experience one of CENTRAL FLORIDA'S MOST BELOVED NEIGHBORHOODS and lifestyles.

553 Arapaho Trail, Maitland

$299,000

3 Beds ⋅ 3 Baths ⋅ Park Lake Twnhs SubDv. ⋅ 32751 Zip Code

Virtually Staged. Welcome to this beautifully updated two-story townhouse in the heart of Maitland, offering a well arranged floor plan, stylish finishes, and exceptional functionality. Featuring three bedrooms and two and a half bathrooms, the thoughtfully designed layout separates the living room from the kitchen and dining area, creating distinct yet connected spaces that feel open, organized, and highly functional. Walk into the fully renovated kitchen, showcasing elegant Calacatta quartz countertops, updated cabinetry, stainless steel appliances, and modern finishes that make it the centerpiece of the home. Waterproof luxury vinyl plank (LVP) flooring extends throughout the entire residence, complemented by updated lighting and fixtures that give the home a fresh, contemporary feel. Upstairs, the spacious primary suite offers a generous walk-in closet and private access to a screened balcony—the perfect place to enjoy your morning coffee or unwind in the evening. Step outside to your private courtyard, an inviting outdoor retreat perfect for relaxing or entertaining. Residents also enjoy access to a sparkling community pool, perfect for cooling off during Florida's warm summer months. Ideally situated with quick access to I-4 and Orange Avenue, this home places you just minutes from Downtown Orlando, top-rated hospitals, shopping, dining, and entertainment. Nearby attractions such as the Orlando Science Center and Orlando Museum of Art provide endless opportunities for culture and recreation, while schools and everyday conveniences are all within easy reach. With tasteful updates throughout, modern finishes, and an unbeatable Maitland location, this move-in-ready townhouse offers the perfect combination of style, comfort, and convenience. Schedule your private showing today!

812 Park Lake Circle Unit 7, Maitland

$230,000

2 Beds ⋅ 2 Baths ⋅ Lake Maitland Terrace Apts SubDv. ⋅ 32751 Zip Code

Welcome to Lake Maitland Terrace! A serene neighborhood perched beautifully on Lake Maitland offering a lakefront pool & clubhouse. Enjoy this first floor corner home with screened porch & lake view. Delight in the retro vibe of this original unit OR renovate to your heart's content. One assigned parking space steps from your front door. Welcome Home!

1140 S Orlando Avenue Unit G8, Maitland

$259,000

3 Beds ⋅ 3 Baths ⋅ Park Lake Grove Condo SubDv. ⋅ 32751 Zip Code

Welcome home to this spacious 3-bedroom, 2.5-bath condo in the desirable Park Lake Grove community. Enjoy peaceful lake views from your living room, and the convenience of an attached 1-car garage. The thoughtfully designed floor plan offers generous living space, 2 primary bedrooms with en suites upstairs, natural light, and plenty of storage. Community amenities include a pool and lake access. Conveniently located near shopping, dining, major highways, and downtown Orlando.

603 Waverly Lane Unit 405B, Maitland

$225,499

2 Beds ⋅ 2 Baths ⋅ Park Lake Twnhs SubDv. ⋅ 32751 Zip Code

Why pay Winter Park prices when you can live minutes away? Welcome home to this beautifully updated 2-bedroom, 1.5-bath townhouse in the heart of Maitland, where location, lifestyle, and value come together. From the moment you walk in, you'll appreciate the many upgrades already completed, including a gorgeous kitchen with quartz countertops and stainless steel appliances, luxury vinyl plank flooring throughout, new energy-efficient windows and sliding glass doors, updated lighting, an updated half bath, and a new A/C (2022). The home features a spacious, fenced private courtyard. You have a partial garage/carport area, or you can utilize the entire space for outdoor living. Picture a patio furniture set, an outdoor TV, a grilling station, and a safe place for the kids to play or the pets to run around. Upstairs, you will find two HUGE bedrooms joined by a Jack-and-Jill bathroom. You cannot find bedrooms this big in newer homes. Each bedroom easily fits a king-sized bed and all furnishings needed. Both bedrooms have dual closets, and then there is an additional closet on the upstairs landing, so storage space will not be an issue. Outside, you'll discover one of the community's hidden gems—an expansive open green space and Park Lake just steps from your front door. Whether you're walking the dog, enjoying time with the kids, or spending a quiet evening outdoors, you'll love the sense of space and tranquility. And then there's the location, because your lifestyle should be just as important as the features of your home. Imagine grabbing coffee in Winter Park, spending Saturday mornings at Lake Lily, or meeting friends on Park Avenue, all without paying Winter Park prices. With easy access to I-4 and several major healthcare campuses nearby, this home is ideally situated for professionals, commuters, and anyone looking for a low-maintenance lifestyle close to everything. Most of the heavy lifting has already been done. All that's left is for you to move in and make it yours. This one won't last long, so schedule your showing today!

820 Park Lake Circle Unit 11, Maitland

$425,000

3 Beds ⋅ 3 Baths ⋅ Enclave/Maitland A-F SubDv. ⋅ 32751 Zip Code

Under contract-accepting backup offers. Welcome to Montacino at Enclave, Maitland—a peaceful, gated oasis where style, comfort, and convenience come together. This move-in-ready 3-bedroom, 2.5-bath townhome showcases timeless character, quality craftsmanship, and a premium location with no rear neighbors, offering tranquil, private views. The A/C system is less than one year old, providing added peace of mind. Inside, the open-concept living, dining, and kitchen area is perfect for entertaining, featuring beautiful ceramic tile flooring, elegant crown molding, and an abundance of natural light. Designer upgrades throughout—including updated lighting, mirrors, and hardware—create a refined, modern feel. Just off the kitchen, a covered rear patio overlooks a spacious, tree-lined green space that is fully maintained by the HOA, allowing you to enjoy the outdoors without the upkeep. The welcoming foyer is flanked by a convenient half bath on one side and access to the attached one-car garage on the other. Upstairs, the spacious primary suite has elegant wood flooring and features a private balcony, a generous walk-in closet, and a well-appointed en-suite bath. Two additional bedrooms, a full bathroom, and a laundry closet with built-in storage shelves complete the second floor, offering comfort and functionality for everyday living. Perfectly located just minutes from Downtown Orlando and Winter Park, this home offers the best of both worlds—easy access to shopping, dining, and entertainment while nestled in a serene lakeside community. Residents enjoy a resort-style pool, scenic sidewalks overlooking Lake Charity, and the security and convenience of low-maintenance living in a beautifully maintained gated neighborhood. This is your opportunity to enjoy resort-style living in one of Maitland's most desirable gated communities. (Attached to pics is additional info on HOA amount)

1395 Benevolent Street, Maitland

$599,000

4 Beds ⋅ 4 Baths ⋅ Enclave/Maitland A-F SubDv. ⋅ 32751 Zip Code

Welcome home to a rare find, one of the largest floor plans in the community, sitting right on Lake Charity. This Mediterranean style townhome greets you with sweeping water views, mature landscaping, and a peaceful stillness that is hard to find this close to everything. Inside, wood floors and tile carry you through the first level. Plantation shutters run throughout the home and you'll find real wood cabinetry, a detail that speaks to the quality of this build. A large family room and dining room combo with a half bath offers plenty of space to entertain. The kitchen features newer appliances and granite countertops, opening into a bright and functional living space. The primary suite is located on the first floor and is oversized, with double vanities, a jacuzzi tub plus separate shower, and a walk in closet. Head upstairs to a spacious landing area that connects three additional bedrooms, featuring walk in closets with closet systems, along with two full bathrooms. Step outside to the true showstopper. Townhomes rarely feel private, but this courtyard is your own Mediterranean oasis. Grow plants, entertain, or simply enjoy the quiet. Another great feature of this home is the all new energy efficient windows and new AC unit, keeping utilities low without sacrificing comfort. Walk through the covered entry to your oversized two car garage, a rare find, offering plenty of room for both vehicles plus storage. As a resident, you'll enjoy a resort style community pool overlooking Lake Charity, all within a gated neighborhood. Minutes from Maitland Boulevard and I4, you're close to Downtown Orlando, Maitland, and Park Avenue. If you're looking to be in the heart of Maitland with the space, privacy and lake views to match, this is the home for you.

1132 Charming Street, Maitland

$975,000

Hollieanna Shores SubDv. ⋅ 32751 Zip Code

Rarely does a homesite like this surface in one of Maitland's most coveted pocket communities. Tucked at the end of a quiet cul-de-sac, 119 Hollie Ct offers a rare chance to build your dream home in an established neighborhood where lots almost never change hands. This secluded, private parcel gives you room to design exactly the home you've always pictured, all in a setting that blends peace and privacy with true Central Florida convenience. Zoned residential, the lot is a blank canvas waiting for your vision—whether that's a modern retreat, a classic family home, or something entirely your own. The real showstopper is what comes with it. Deeded access to the neighborhood boat ramp puts the renowned Chain of Lakes within easy reach, opening the door to boating, fishing, and lazy afternoons on the water whenever the mood strikes. That kind of waterfront recreation is a rare perk, and here it's part of everyday life. Beyond the community, everything you need sits close by. Shopping, restaurants, major roads, theme parks, and the airport are all just minutes away, giving you quiet suburban calm without giving up quick access to the rest of the region. Opportunities like this simply don't come along often. A private lot, lake access, and a premier Maitland address rarely align in a single offering. Bring your builder, bring your plans, and start turning your dream home into reality. Schedule your private showing today before this rare lot slips away!

119 Hollie Court, Maitland

$834,900

3 Beds ⋅ 2 Baths ⋅ Dommerich Hills Second Add SubDv. ⋅ 32751 Zip Code

Discover a rare waterfront, pool-home in the desirable Dommerich Hills neighborhood. This exceptional property offers the ideal combination of family-friendly living, modern convenience, and breathtaking natural beauty. The open floor plan welcomes you with vaulted ceilings and natural light in the living room, dining room, kitchen, and family room. Bamboo flooring enhances the bedrooms and living room, while cool and durable tile flooring extends throughout the remaining living areas. The family room features a wood-burning stone fireplace. Just outside, a lakeside fire pit is perfect for relaxing with family and friends while taking in peaceful water views and sunsets. The 12-foot-deep lanai overlooks the screened swimming pool and the 120 feet of lake frontage. Across the water lies a protected nature preserve, providing a backdrop of trees and nature. Whether hosting holiday gatherings, celebrating special occasions, or enjoying quiet evenings at home, the layout provides flexibility and comfort. Imagine your own pineapple patch and fruit trees! You’ll have seasonal oranges, Key limes, plums, and kumquats. Whether you're enjoying your morning coffee overlooking the lake or spending evenings under the stars, the outdoor spaces invite you to slow down and savor every season. The original 1968 home was replaced with a new home in 1997, incorporating the updated building codes that required hurricane-resistance structures. The home was connected to the new City of Maitland sewer system in 2025. New water heater 2026. This is more than just a home; it's a lifestyle. Here, families have room to grow, creating lasting memories, and nature is always just outside the door. This home has an exceptional waterfront setting and is situated very close to the Maitland and Winter Park Chain of Lakes. With a bright and inviting interior, thoughtful features, and an outstanding location, with A-rated schools, this property offers a rare opportunity to enjoy peaceful lakeside living without sacrificing convenience.

2624 Tuscarora Trail, Maitland

$420,000

2 Beds ⋅ 2 Baths ⋅ Lake Maitland Terrace Apts SubDv. ⋅ 32751 Zip Code

Welcome to Lake Maitland Terrace, where this beautifully renovated condominium offers a rare opportunity to enjoy Chain of Lakes living. Included with the property is a leased boat dock on the Winter Park Chain of Lakes, paid through 7/31/2027, with the lease transferable to the new owner and renewable. This stunning 2-bedroom, 1.5-bath residence features picturesque lake views from both bedrooms as well as the screened front porch. The screened-in front porch is the perfect place to relax while overlooking the expansive lakefront campus, complete with a sparkling pool, fishing dock, putting green, and shuffleboard courts. From the moment you step inside, you'll appreciate the exceptional quality of the modern renovation, thoughtfully designed with both style and function in mind. The beautifully updated kitchen is ideal for entertaining, featuring premium finishes, generous workspace, and a party-size ice maker. It flows seamlessly into the dining area, where abundant built-in storage provides both convenience and organization. The spacious primary suite serves as a private retreat, complete with a walk-in closet, an updated half bath, and tranquil lake views to wake up to each morning. Whether you're looking for a full-time residence or a weekend escape, this move-in-ready home offers an exceptional lifestyle in one of Winter Park's most desirable waterfront communities. This is a rare opportunity you won't want to miss.

1140 S Orlando Avenue Unit K15, Maitland

$950,000

3 Beds ⋅ 2 Baths ⋅ Dommerich Woods SubDv. ⋅ 32751 Zip Code

Outstanding Dommerich Woods location on .28 acre lot with serene views of the nature preserve! This immaculate home offers the perfect blend of comfort, style and privacy. Tucked away on a charming tree-lined cul-de-sac, 823 Woods Court welcomes you with exceptional curb appeal. Step inside to a spacious foyer introducing gleaming wood floors, elegant crown molding, and an abundance of natural light. The versatile floor plan offers several inviting living spaces! At the front of the home, the formal living & dining rooms flow seamlessly into the beautifully updated kitchen, complete with a cozy breakfast nook, new cabinetry, quartz countertops, stainless steel appliances and an oversized breakfast bar overlooking bright family room. French doors open to the spectacular 28x11 sunroom with vaulted ceilings and a stunning wall of windows, providing breathtaking views of the manicured backyard, two private patios and the tranquil nature preserve- creating a peaceful retreat you'll enjoy year-round. The spacious primary suite features two closets and a generously sized en-suite bath with dual vanities and built-in storage. Two additional guest bedrooms and a large guest bathroom with built-in closets provide plenty of space for family and visitors. Additional updates and features include fresh interior paint, an inside laundry room, a two-car garage with new garage door, a new Trane HVAC system. new water heater. irrigation system with new well pump, Roof 2018 & NO HOA! Excellent schools: Dommerich Elementary, Maitland Middle & Winter Park High! Residents enjoy access to the Dommerich boat ramp on Lake Minnehaha/Chain of Lakes, as well as a short stroll to the newly refurbished boardwalk leading to Maitland Community Park. This move-in ready home combines an exceptional location, thoughtful updates, and picturesque surroundings ...WELCOME HOME!

823 Woods Court, Maitland

$375,000

3 Beds ⋅ 2 Baths ⋅ Lakewood Shores SubDv. ⋅ 32751 Zip Code

Under contract-accepting backup offers. Sensational ALL-Block Home in Maitland with NO HOA and Deeded Private Lake Access! Nestled within Lakewood Shores, a charming and welcoming enclave of 42 homes, this 3BR/2BA residence offers a leisurely lifestyle with deeded access to Lake of the Woods via private neighborhood boat ramp. Venture inside to discover an openly flowing traditional layout, soft natural light, well-equipped kitchen w/skylights, separate dining area, and a cozy living room with a wood-burning fireplace. Each bedroom is generously-sized, while the primary bedroom has an en suite w/step-in shower. Enjoy the entertaining possibilities of the screened-in lanai, as well as the fenced-in backyard boasting a shed with electricity connected. Other features: attached carport w/newly epoxy floors, indoor laundry area, new electrical service panel, updated windows/plumbing/water heater, cost-savings well sourced irrigation system, near Maitland Art Center, Lake Lily Park, and the Enzian Theater, close to Downtown Maitland, Park Avenue, Winter Park Village, I-4, and much more! Call and schedule your private showing today!

110 N Lakewood Circle, Maitland

$419,900

2 Beds ⋅ 2 Baths ⋅ Lake Maitland Terrace Apts SubDv. ⋅ 32751 Zip Code

Virtually Staged. RARE LAKEFRONT opportunity to Live right on LAKE MAITLAND! Sip your morning coffee with one of the most premier views in the entire community! BONUS: It's on the main FIRST floor, so NO STAIRS! Just a pure unencumbered view of Lake Maitland right from your living room! And only a few steps to the dock or community pool!! This unit has the EXTRA HALF BATHROOM and has been tastefully updated to accentuate it's incredible mid century modern original features, that are in immaculate condition! There may never be another unit quite like this one! The high end plantation shutters offer privacy when needed, but can stay wide open for that view! Enjoy the remodeled Community POOL & Clubhouse all on the stunning water front of Lake Maitland which is also connected to the Winter Park Chain of Lakes. Plenty of fishing, fun and relaxing to be had on the community dock, shuffleboard and putting green! So many amenities nestled amongst the towering shade trees and mature landscaping. The Mid Century Modern architecture is about as timeless of a look that you can find that fits the Maitland/Winter Park lifestyle. You couldn't ask for a better location at just minutes from downtown Winter Park, Park Ave, SunRail station and all the restaurants surrounding the 17/92 Maitland/Winter Park Corridor. All Units recently had metal roof replacement in 2025 and were just freshly painted as well. It's completely move in ready with all New Luxury Vinyl Plank Flooring, Kitchen and bathroom updates,. This unit has not been available for many years, so don't miss out on this view!

1140 S Orlando Avenue Unit H3, Maitland

$800,000

3 Beds ⋅ 3 Baths ⋅ Lakewood Shores 1st Add SubDv. ⋅ 32751 Zip Code

Under contract-accepting backup offers. Nestled on the shores of skiable Lake of the Woods, this beautifully maintained 3-bedroom, 2 and a half bath waterfront residence offers over 105 feet of private lake frontage with breathtaking open-water views. Designed for those who embrace the lake lifestyle, the property features a private boat launch, two docks, and a solar-powered boat lift, providing effortless access to one of Central Florida's most desirable private lakes. Inside, vaulted ceilings and abundant natural light create an inviting atmosphere, while the updated kitchen opens seamlessly to the living and dining spaces, making everyday living and entertaining a pleasure. The primary suite enjoys peaceful water views, and the home's coastal-inspired finishes enhance the relaxed lakefront setting. A spacious rear deck overlooks the water and serves as the perfect place to enjoy sunrise coffee, sunset gatherings, and weekends on the lake. Additional highlights include a durable metal roof, wood floors, mature landscaping, generous outdoor living spaces, and a prime Maitland location convenient to shopping, dining, top-rated schools, Winter Park, and Downtown Orlando. Rarely does an opportunity arise to own a move-in ready waterfront home with this combination of frontage, amenities, and direct access to skiable waters.

195 Cedarwood Drive, Maitland

$295,000

2 Beds ⋅ 2 Baths ⋅ Sun Bay Club Condo Ut 1 SubDv. ⋅ 32751 Zip Code

Ground-floor 2BR/2BA in the gated, lake-access community of Sun Bay Club in Maitland, FL — updated and move-in ready! The kitchen was renovated in 2023 with new cabinets, quartz countertops, and updated appliances (microwave 2024, dishwasher 2025). Both bathrooms were updated in 2026: the primary with a new double-sink vanity, modern lighting, and a pocket door for privacy, and the hall bath with a new vanity, mirror, and lighting. Durable wood-look tile and wood flooring throughout — no carpet. This is a two-story building, which falls outside Florida's SIRS and milestone inspection requirements that apply to condos three stories and taller. The open-concept living space extends through sliding glass doors to an enclosed sunroom overlooking the pond, ideal as a home office or morning coffee spot, and each bedroom opens to its own private screened patio. The primary suite adds a walk-in closet with built-in shelving; the second bedroom offers double closets with built-in shelving as well. HOA fee includes cable/internet, lake access for boats and jet skis, a large lakefront pool, a tennis court, and all exterior maintenance, including the roof. Minutes to Maitland and Winter Park shopping and dining, and easy access to highway I-4. Great option for low maintenance living as a primary residence or an investment opportunity. Schedule a viewing today!

1000 Winderley Place Unit 141, Maitland

$638,900

3 Beds ⋅ 3 Baths ⋅ Enclave At Maitland A-F SubDv. ⋅ 32751 Zip Code

"PRICE IMPROVEMENT" ON THIS MOVE-IN READY 3-BED, 2.5-BATH SINGLE FAMILY HOME IN THE "EXCLUSIVE GATED COMMUNITY OF ENCLAVE AT MAITLAND", FL 32751. Nestled within the highly sought-after & gated community of Enclave at Maitland, Single Family Homes rarely come on the market and this home offers a Luxury Interior Footprint that's a perfect balance of privacy, elegance, and convenience. Fully updated & loaded with high-end finishes, the triple split-plan layout features separate Formal Dining & Family Rooms that maximize both entertaining and day-to-day privacy. Enter through a HUGE 21' Long Foyer into the Large Family Room which boasts a 14' High Tray Ceiling and the Centerpiece of the home. Just off the Family Room is the Formal Dining room, perfect for entertaining & family dinners. The Kitchen is perfectly designed for the Serious Chef, boasting Level 3, 42" Maple Cabinetry with Upper Crown Molding, Premium Granite, Center Island with a (3) Person Breakfast Bar, Stainless Appliance Package including Double Built-In Ovens, French Style Refrigerator, Flat-Top Range, Tons of Counter & Storage Space, Dual Stainless Sink, Custom Tile Backsplash, Pendant & Recessed Lighting, Closet Pantry and an adjoining Sunlit Dinette that provides the perfect spot for casual morning coffee. The Primary Suite is the Perfect Couples Retreat! The Bedroom is generous in size and will accommodate all of your oversized furniture & features a HUGE Tray Ceiling, Crown Molding, Laminate flooring, and Dual Walk-In Closets outfitted w/Custom Storage Organizers. The En-Suite Bathroom offers His-and-Her Maple Vanities w/Undermount Sinks, Granite Counters, Deep Garden Soaking Tub wrapped in Custom Tile, Large Walk-In Shower engineered with Dual Shower heads at opposite ends, Under-Cabinet Accent Lighting and a Glass Block Window for lots of natural lighting. On the opposite side of the residence, Two Additional Bedrooms share a beautifully appointed Full Bathroom, offering an ideal setup for Children & Guests. If you work from home or just looking for a quiet space, you'll enjoy the Private Office/Den located just off the Family Room. The Interior Laundry Room is highly functional and included Front-Load Washer & Dryer, Integrated Wash Tub/Sink & Upper Storage Cabinets. Your living space effortlessly expands outdoors through a Triple-Slider to the 12'x16' Covered Back Porch w/Premium Slate Tile flooring. Here, you can unwind against the peaceful backdrop of an unobstructed Lake View & Conservation Area. Additional Features: Prestigious Maitland Lifestyle, Low-Maintenance Luxury, Directly Across from the Pool, Block & Stucco, Barrell Tile Roof, Freshly Painted Inside & Out, High Ceilings Throughout, Carrier HVAC (2021), Vacuflo Central Vac System, GE Hybrid 50 Gal Water Heater (2016), Double-Paned Windows, 18x18 Tile Flooring Flowing Diagonally, Premium 8" Crown Molding, Elegant Custom Arches, Tray Ceilings, 8’ High Doors, Upgraded 6" Baseboards, Surround Sound Speaker & Prewire, Security System, Ceiling Fans/Light, Pre Plumbing for Summer Kitchen, Epoxy Coated Garage Floor and (2) Garage Door Openers, Custom Garage Storage, Paver Driveway, Beautiful Palms, Magnolias & Ivy, Private Mailbox, Irrigation System and more. Incredible location close to I-4, Downtown Maitland, Altamonte & Orlando, Shopping, Dining, Theme Parks, Turnpike, Beaches and all Central Florida has to offer. Call today for more info or schedule a private showing. This is Move-In Ready Perfection!

1404 Caring Court, Maitland

$1,095,000

4 Beds ⋅ 4 Baths ⋅ Maitland Club Rep SubDv. ⋅ 32751 Zip Code

This elegant Mediterranean-inspired one-story residence is in the gated community of Maitland Club overlooking a tranquil pond. A well maintained 4 bedroom, 4 bath Plus home office with recent updates that include a new roof, hot water heater, pool heater, and a re-pipe. The home features a soft neutral interior palette throughout with an elegant formal living room filled with natural light featuring soaring ceilings and a dramatic wall of arched windows and French doors overlooking the outdoor living area. The dining room and home office are just off the entry foyer. The home office offers a warm workspace with hard wood flooring, custom bookcases and cabinetry. This room could be a temporary guest room it features a closet and is adjacent to the pool bath. The kitchen offers generous workspaces with extensive cabinetry, solid surface countertops, a center island, and a breakfast bar overlooking the family room. The open concept includes a planning desk and a casual dining space overlooking the pool. The spacious family room is designed for comfortable everyday living and effortless entertaining, featuring high ceilings, recessed lighting, and a fireplace framed by custom built-in audio-visual cabinetry. An oversized primary suite with a dramatic tray ceiling and expansive sitting area creates a true retreat-like atmosphere with an en-suite attached that features a large double vanity with dressing table, a relaxing garden tub and a large walk-in shower. On the opposite side of the home find three generous sized guest rooms and two full baths, laundry and hall to three car garage. The sparkling pool with tiered entry steps is surrounded by an expansive covered patio offering multiple seating and dining areas, all overlooking a lovely pond. Roof, Garage Floor and Pool heater warranties are available upon request.

1911 Belford Court, Maitland

$184,900

2 Beds ⋅ 2 Baths ⋅ Visconti West Condo SubDv. ⋅ 32751 Zip Code

If you are looking for a terrific property, look no further! You or your tenant can live the lifestyle deserved in this RESORT-STYLE, video-monitored GATED COMMUNITY located on beautiful Lake Shadow in the heart of Maitland Center. This two-bed/two-bath, 2nd-story, CORNER UNIT features an OPEN floor plan with a LIVING/DINING COMBO and 9-FOOT CEILINGS. The KITCHEN includes a breakfast bar, closet pantry, INSIDE UTILITY CLOSET with washer and dryer, and neutral tile. All appliances convey at closing. DOUBLE MASTERS each offer an en-suite bath and a walk-in closet. The 20 X 20 living area provides lots of sunlight and features a built-in nook with glass shelving you can use as you choose. In 2024, the interior was painted, and carpet was installed. Through sliders, you can unwind at the end of a busy day on the SCREEN-ENCLOSED tiled LANAI and enjoy a TRUE ESCAPE. If extra storage is needed, a patio closet awaits! This GORGEOUSLY LANDSCAPED and PET-FRIENDLY community offers two LAKESIDE POOLS with Wi-Fi access, a club-quality FITNESS CENTER, grand CLUB ROOM with CATERING KITCHEN, fully-equipped BUSINESS CENTER, lighted TENNIS courts, BASKETBALL court, car wash area, two laundry facilities, 24-HOUR MAINTENANCE, WATER, SEWER, and a Monday-Friday VALET WASTE REMOVAL SERVICE. The condo community boasts a newer tile roof, reflecting ongoing care and investment in the property. Located minutes away from SR 414, I-4, 429, Routes 434 and 436; it is a quick drive to downtown Orlando, Cranes Roost Park, and to the upscale shopping and dining at Altamonte Mall, Altamonte Towne Center, Winter Park Village, and Winter Park’s quaint Park Avenue. Enjoy Florida living at its best! This property may be under audio & visual surveillance.

1440 Lake Shadow Circle Unit 8201, Maitland

$899,000

4 Beds ⋅ 2 Baths ⋅ Versailles SubDv. ⋅ 32751 Zip Code

Ideally in one of Maitland’s desired neighborhoods, Versailles, this fully renovated home blends timeless architecture with modern comfort. With sun-filled interiors, an open-concept layout, a serene primary suite and freshly landscaped grounds, every detail supports effortless living. This three-bed, two-bath home stretches over 2,151 square feet and is situated on 0.29 of an acre. This classic ranch style offers a split bedroom plan with endless function. A gracious foyer welcomes you into this serene space with blonde oak flooring, limewash accent walls, a vaulted ceiling with wood beam accents, fresh neutral tones, designer fixtures and ambient lighting that softens the spaces. This home features formal dining and a flex space that could be a fourth bedroom or office, offering many layout choices. The combined kitchen and living room showcases a wood-burning fireplace with a fluted marble surround as the focal point. The kitchen combines crisp, clean-lined cabinets and warm-wood-toned floor-to-ceiling storage cabinets finished with brushed-gold hardware. A waterfall center island with quartz counters that continue up the backsplash for a stylish design. Clear view sliders open to a covered porch with a tongue and groove ceiling feature and is part of a screened pool, making entertaining a breeze. Recently installed turf grass for ease of maintenance and keeps it all looking very fresh. The pool was recently refinished and a side-yard sauna rounds out this oasis. The primary suite is a private retreat with an oversized walk-in shower with beautiful vertical Zellige tile. Dual vanities with custom arched mirrors, sconce lighting and porcelain-marble floors add to the space. Built-in linen closets and dual bedroom closets make organization simple. Additional highlights include both baths completely renovated, new kitchen appliances (LG/GE stainless steel) induction range, new interior doors and hardware, new ceiling fans, new Pella front doors and Impervia slider doors across the back of the home, new Pella front windows, a new Hass garage door (2025), the whole yard professionally designed and landscaped (2026), a sauna (2024), a roof (approximately 2018) and a water heater (2023). This neighborhood enjoys a community lake lot with access to Lake Minnehaha, part of the Winter Park lake chain. Strategic location close to major roadways, short distance to the Sunrail and close to all amenities that make Maitland special. Zoned for some of the best Orange County schools: Lake Sybelia, Maitland Middle and Winter Park High, a nationally renowned school for its International Baccalaureate Program.

908 Versailles Circle, Maitland

$485,000

3 Beds ⋅ 3 Baths ⋅ Enclave/Maitland A-F SubDv. ⋅ 32751 Zip Code

Welcome to this beautifully maintained lakefront townhome in a highly desirable gated community in Maitland with almost 1900 square feet of thoughtfully designed living space. This 3-bedroom, 2.5-bath residence combines comfort, functionality, and picturesque lake views. Enjoy serene views of Lake Charity from the charming front porch, formal dining room, and two upstairs bedrooms. Soaring ceilings and abundant natural light create an airy, inviting atmosphere throughout the home. The spacious open-concept kitchen overlooks the family room and features ample counter seating for barstools, generous cabinetry, and a nice pantry. A private courtyard provides a welcoming outdoor retreat and leads to the oversized 2-car garage with abundant attic storage above. The separate dining room offers a perfect setting for entertaining while enjoying tranquil lake views. A convenient guest bathroom is located on the first floor as well. Upstairs, the massive Primary suite serves as a true retreat, featuring a custom walk-in closet and a spa-inspired en-suite bath with a soaking tub, separate shower, and dual vanities. Two additional bedrooms have stunning views of the lake. One includes a Murphy bed with beautiful built-ins and a custom closet. Another full bath, and a spacious laundry room with plenty of storage complete the second floor. The reasonable HOA fee includes use of the sparkling pool, the secure gate, all landscaping, all maintenance of the exterior of this townhome including the roof, repairs, and paint, and high-speed internet with cable TV, through Spectrum. Offering exceptional space, beautiful water views, and a sought-after gated location, this townhome is the ideal place to call home. *A complimentary complete one-year Home Warranty is provided for extra peace of mind. (A recent Lender's appraisal is also available.)

1106 Charming Street, Maitland

$975,000

3 Beds ⋅ 3 Baths ⋅ Hollieanna Shores SubDv. ⋅ 32751 Zip Code

Located in a premier Maitland neighborhood, 119 Hollie Ct presents a rare opportunity to own a beautifully maintained home in an established pocket community where properties seldom come on the market. This secluded one-level residence sits on a private lot and includes deeded access to the neighborhood boat ramp and the renowned Chain of Lakes, bringing waterfront recreation within easy reach. Inside, you will find 2,192 square feet of bright and inviting living space across 3 bedrooms and 3 bathrooms. The kitchen opens directly into the gathering room, where a cozy fireplace creates a warm focal point for relaxing or hosting friends and family. An adjoining sunroom takes full advantage of the home's southern exposure, filling the interior with natural light throughout the day and adding a cheerful energy to everyday living. The split floor plan is designed with privacy in mind. The oversized primary suite occupies one side of the home and features a large ensuite bathroom with double sinks, a separate shower, and a soaking tub for those well-deserved moments of relaxation. On the opposite side, two additional bedroom suites provide comfortable and independent spaces for family members or visiting guests. A small bonus area adds welcome flexibility, serving nicely as a home office, hobby room, or creative studio. Outside, the backyard offers a true personal retreat. A sparkling pool and a terrace shaded by a beautiful pergola create the perfect setting for entertaining outdoors or simply unwinding in peace. The seamless blend of indoor and outdoor spaces makes this home ideal for the Florida lifestyle. Beyond the property itself, the location delivers everyday convenience with easy access to shopping, restaurants, theme parks, major roads, and the airport. You get the best of quiet suburban living without sacrificing proximity to everything Central Florida has to offer. Homes in this neighborhood rarely become available, making this a truly unique opportunity. Schedule your private showing today and see everything this special property has to offer before it is gone.

119 Hollie Court, Maitland

$331,000

2 Beds ⋅ 2 Baths ⋅ Maitland Harbour Apts SubDv. ⋅ 32751 Zip Code

Experience the best of lakeside living in this beautifully updated third-floor corner residence with panoramic views of Lake Maitland. Perfectly positioned along Orlando Avenue and adjacent to Fort Maitland boat ramp, the home combines convenience with a truly unique lifestyle just minutes from Winter Park’s shopping, dining, and cultural attractions. Inside, you’ll find luxury vinyl plank flooring throughout and a stunning kitchen designed for modern living, showcasing quartz countertops, sleek stainless steel appliances, custom cabinetry, and stylish finishes that create an inviting atmosphere for both cooking and entertaining. The spacious primary suite is highlighted by a custom-designed closet for optimal storage and comfort. Enjoy community amenities that make every day feel like a retreat, including a pool overlooking the lake and access to boat slips (via waitlist) on the highly coveted Winter Park Chain of Lakes. Whether you’re seeking a serene escape or a vibrant, connected lifestyle, this condo delivers the rare combination of location, water views, and thoughtful updates in one of Central Florida’s most desirable areas.

1000 S Orlando Avenue Unit A31, Maitland

$2,999,000

6 Beds ⋅ 5 Baths ⋅ Lake Sybelia Shores SubDv. ⋅ 32751 Zip Code

Welcome to luxury lakefront living at its absolute finest in the heart of Maitland, Florida. Nestled along the pristine shores of Lake Sybelia, this extraordinary three-story estate offers an unparalleled combination of elegance, comfort, and breathtaking waterfront views. Boasting 5,355 square feet of thoughtfully designed living space, this stunning residence features six spacious bedrooms, four and a half bathrooms, and an open-concept floor plan perfectly crafted for both entertaining and everyday living. Expansive walls of glass fill the home with natural light while showcasing panoramic lake views from nearly every room. The main living area seamlessly connects the gourmet kitchen, dining room, living room, and family room, all overlooking the sparkling waters of skiable Lake Sybelia. Designed with indoor-outdoor living in mind, each floor features a balcony spanning the entire width of the rear of the home, creating multiple spaces to relax and enjoy Florida’s spectacular sunsets. Step outside to your private resort-style oasis complete with a gorgeous pool, lush landscaping, and direct lake access with your own private boat dock and lift, perfect for boating, skiing, and waterfront recreation year-round. The upstairs retreat is anchored by an impressive primary suite featuring serene lake views and private balcony access. The upper level also includes a dedicated private office, ideal for working from home while enjoying stunning lakefront views. Two additional bedrooms share a beautifully designed Jack-and-Jill bathroom, while another flexible bedroom space can easily serve as a nursery, fitness room, or additional guest bedroom. Every level of the home has been carefully designed to maximize comfort, privacy, and functionality while maintaining a sophisticated and timeless aesthetic throughout. The lower level offers endless entertainment possibilities with a spacious game room, a full movie theatre, an additional guest bedroom, and a full bathroom ideal for visitors or multi-generational living. Completing this exceptional property is a beautiful temperature controlled wine cellar holding almost 2,000 wine bottles, a two-car garage with additional storage space, a large home generator, and countless luxury details throughout. This one-of-a-kind Lake Sybelia estate delivers the perfect balance of upscale living, modern convenience, and the ultimate waterfront lifestyle in one of Central Florida’s most desirable locations.

1166 N Lake Sybelia, Maitland

$325,000

2 Beds ⋅ 2 Baths ⋅ Lake Maitland Terrace Apts SubDv. ⋅ 32751 Zip Code

One or more photo(s) has been virtually staged. Where Maitland's pristine waters meet a modern lifestyle! This luxury condominium in the coveted Lake Maitland Terrace community offers a rare blend of elegance and convenience on the shores of Lake Maitland within the famed Winter Park Chain of Lakes. Nestled among lush green spaces, this impeccably maintained mid-century modern complex boasts easy access to boutique shops, upscale dining, and vibrant entertainment. This unit stands out with its unique two-bedroom, one-and-a-half-bath layout—a rare find in the community, where most units are built with just one bath. Sunlight floods in through large windows, and warm wood floors flow throughout. This charming efficiently designed kitchen, with light cabinetry with contrasting hardware, quartz counters, and stainless steel appliances, is perfect for entertaining. Beyond the comforts of the home, enjoy the exclusive opportunity to secure a boat slip—a prized amenity in this tranquil lakeside retreat. Complex is amenity-rich with sidewalks, a community pool where residents enjoy lake access with beautiful views. The amenities include a clubhouse with a full kitchen, kayak racks, a fishing pier, and a personal storage unit. Walk to Lake Lily Park’s events, the Enzian Theater, and be just minutes from Winter Park Village and Park Avenue. Zoned for top-rated schools—Dommerich Elementary, Maitland Middle, and Winter Park High—this is a chance to embrace the best of Maitland living. Don’t miss your chance to claim this exceptional retreat as your own.

1140 S Orlando Avenue Unit I14, Maitland

$815,000

4 Beds ⋅ 3 Baths ⋅ Stonewood First Add SubDv. ⋅ 32751 Zip Code

From the moment you step inside, you’re welcomed by a stunning double-sided fireplace and a sought-after conversation pit — the perfect setting to unwind with your favorite vinyl record, a glass of wine, and great company. Beyond the fireplace, the home opens into an expansive open-concept living space designed for both everyday comfort and effortless entertaining. The chef-inspired kitchen is the centerpiece of the home, featuring premium Forno appliances, a massive 11-foot island with seating for six, and a 6-burner Forno gas range with electric oven. Vaulted ceilings enhance the sense of space, while thoughtful details like the pot filler, apron sink, designer backsplash, and elegant cabinet hardware elevate the entire experience. Adjacent to the kitchen, the butler’s pantry offers butcher block countertops, abundant cabinetry, and a wine fridge — ideal for hosting and extra prep space. A conveniently located full guest bathroom nearby provides privacy and easy access for visitors, separate from the primary and secondary bedrooms. Situated on beautiful Lake Ruby, the outdoor living is just as impressive along with beautiful sunsets. Spend evenings around the fire pit overlooking the water, relax in the screened-in patio, or host unforgettable gatherings in the spacious backyard. A dedicated grilling patio makes outdoor entertaining easy year-round and perfect for holidays, cookouts, and waterfront living at its finest.

457 Forestwood Lane, Maitland

$1,795,000

3 Beds ⋅ 3 Baths ⋅ Sheridan Place SubDv. ⋅ 32751 Zip Code

Welcome to an extraordinary lakefront sanctuary at 631 Lake Catherine Drive, where sophisticated luxury meets serene waterfront living in one of Maitland's most coveted locations. This meticulously renovated residence, rebuilt down to the studs, represents the pinnacle of modern Florida elegance and is offered at $1,795,000. Positioned on an elevated lot overlooking the sparkling waters of Lake Catherine, this stunning home captures breathtaking lake views from nearly every room while offering the privacy and tranquility of a gated rear driveway accessible from a peaceful cul-de-sac. The heart of this home is the chef's kitchen, appointed with premium Cafe appliances, a Miele dishwasher, gleaming quartz countertops, and the convenience of a pot filler faucet. Expansive glass sliders seamlessly connect the kitchen to an inviting deck, creating the perfect setting for alfresco dining while drinking in panoramic lake vistas. The adjacent laundry room elevates everyday living with a built-in coffee bar and sink, transforming a functional space into a stylish amenity. Throughout the home, rich wood flooring flows beneath soaring vaulted ceilings accented by architectural beams, while recessed lighting and all-new windows bathe every corner in natural light. The luxurious primary suite offers a private retreat with its own mini-split system for personalized climate control, a spacious dressing room within the walk-in closet, and a spa-inspired ensuite bathroom featuring double vanities and a generous walk-in shower. Two additional well-appointed bedrooms provide flexibility, with the second bedroom boasting its own private ensuite with walk-in shower, while the third bedroom offers versatility as either a guest room or sophisticated home office. A third full bathroom in the hallway ensures comfort and convenience for family and guests alike. The attached garage has been thoughtfully enhanced with a dedicated gym area, while the exterior showcases fresh landscaping and a newer roof. Beyond the walls of this exceptional residence lies an equally impressive lifestyle. Zoned for the highly regarded Lake Sybelia Elementary and Maitland Middle Schools, this walkable community places you in close proximity to neighboring lakes and the charming ambiance of Lake Lily. Just ten minutes from Winter Park's iconic Park Avenue, residents enjoy effortless access to world-class shopping, dining, and cultural experiences. This is more than a home; it is a lifestyle of refined waterfront living where every detail has been carefully considered to create an absolutely stunning residence that must be experienced to be truly appreciated.

631 Lake Catherine Drive, Maitland

$204,950

1 Beds ⋅ 1 Baths ⋅ Lake Maitland Terrace Apts SubDv. ⋅ 32751 Zip Code

PRICE IMPROVEMENT! Live the lake lifestyle in this beautifully updated 1-bedroom condo located in the iconic mid-century modern community of Lake Maitland Terrace. Completely refreshed in 2025, this first-floor residence features a brand-new HVAC system, new appliances including washer, dryer, and kitchen disposal, updated kitchen countertops, and new flooring throughout the living areas. Freshly painted and thoughtfully enhanced, the home blends timeless mid-century character with modern comfort and style. The spacious bedroom showcases sleek modern concrete flooring, adding to the authentic architectural aesthetic and contemporary feel. Perfectly positioned within a charming two-story mid-rise building, this residence offers effortless access to the community’s exceptional waterfront amenities and relaxed lakefront atmosphere. Set on Lake Maitland—the largest lake on the Winter Park Chain of Lakes—residents enjoy direct lake access for boating, kayaking, canoeing, fishing, and water-skiing. A private community dock is located on-site, while the City of Maitland public boat ramp sits conveniently next door. Boat slips may also be available upon request. The location is truly unbeatable. Just one block from Lake Lily and Fort Maitland Park, and only minutes from Park Avenue, residents can walk to the Maitland Farmers Market, local restaurants, coffee shops, gym, dry cleaning, barber shop, boba tea, and more—all directly across the street. Enjoy easy biking access to Park Avenue for premier shopping, dining, and entertainment. Residents of Lake Maitland Terrace enjoy outstanding amenities including a newer community pool, lakefront clubhouse with breathtaking views available for private events, on-site laundry facilities, free unlimited water, and twice-weekly valet trash service. Experience maintenance-free living where iconic mid-century modern design meets modern updates and an unmatched Central Florida lakefront lifestyle.

1140 S Orlando Avenue Unit E2, Maitland

$970,000

4 Beds ⋅ 3 Baths ⋅ Dommerich Estates 3rd Add Maitland SubDv. ⋅ 32751 Zip Code

Beautifully updated four-bedroom, 2.5-bath home in the heart of Dommerich Estates, one of Maitland’s loved neighborhoods known for its top-rated schools, tree-lined streets and access to the Winter Park Chain of Lakes. Just steps from the neighborhood lake lot and nearby Maitland Community Park, this home offers over 2,300 square feet with warm wood flooring, crisp light walls and thoughtful designer updates throughout. Formal living and dining spaces flow into an open kitchen and gathering area, with large sliding doors leading to the backyard for effortless indoor-outdoor entertaining. The kitchen features custom 42-inch cabinetry, quartz countertops, stainless steel appliances, peninsula seating and generous pantry and laundry space. The living room centers around a charming brick, wood-burning fireplace with expansive backyard views. Outside, enjoy a screened porch, a PebbleTec pool, a paver deck and additional green space perfect for relaxing or entertaining. The spacious primary suite includes double vanities, a walk-in shower and ample closet space. Major updates include a roof (2022), Trane XV19 variable-speed HVAC (2024), updated kitchen finishes (2022), a Pentair pool heater, a new pool pump, a Jandy iAquaLink automation system, recessed lighting, a Google Nest doorbell and Lutron Caseta smart home controls. Enjoy close proximity to Dommerich Elementary and Maitland Middle, zoned for Winter Park High, plus easy access to parks, Lake Lily, the Enzian Theater, restaurants and more.

1851 Huron Trail, Maitland

$703,000

3 Beds ⋅ 3 Baths ⋅ Dommerich Ests 1st Add SubDv. ⋅ 32751 Zip Code

Welcome to 1761 Tippicanoe Trail, a beautifully maintained home nestled on a quiet, tree-lined street in one of Maitland’s most desirable neighborhoods. This inviting residence blends timeless charm with thoughtful updates, offering comfort, style, and an exceptional location. Step inside to find warm and welcoming living spaces filled with natural light, spacious gathering areas, and a functional layout ideal for both everyday living and entertaining. The well-appointed kitchen flows seamlessly into the dining and family areas, creating an easy and comfortable lifestyle. The home features comfortable bedrooms, including a peaceful primary suite with a newly remodeled primary bathroom designed with modern style and convenience in mind. Additional updates include a newer AC system that is only one year old, providing peace of mind and energy efficiency. Enjoy Florida living year-round with a private backyard perfect for relaxing or hosting guests. Residents also enjoy deeded lake access, adding even more appeal to this special Maitland property. Don't miss the virtual walk through and floor plan sketch. Located in a great school district and just minutes from Park Avenue, beautiful parks, shopping, dining, and major roadways, this home offers the perfect combination of location, lifestyle, and value. Don’t miss the opportunity to make 1761 Tippicanoe your next home.

1761 Tippicanoe Trail, Maitland

$215,000

2 Beds ⋅ 2 Baths ⋅ Park Lake Twnhs SubDv. ⋅ 32751 Zip Code

A beautiful affordable condo in Maitland. 2 bedrooms and 1 ½ baths with a 1 car garage. The kitchen has been updated with white cabinets and new counter tops. The appliances have been updated. There is a large dining room and separate living room. The utility room is on the 1st floor with an updated barn door for access. The 1st floor has wood flooring while the second floor has carpeting. The second floor has two bedrooms with an updated bathroom. The shower has been remodeled to allow easy access. This home has a large patio with artificial grass flooring. The one car garage is an added bonus. The property has had the window replaced, a new water heater (2026) and the electrical panel upgraded within the past couple of years. The A/C system was replaced in 2022. This wonderful unit is at a great price and will not last long.

814 Park Lake Circle Unit 8, Maitland

$1,695,000

4 Beds ⋅ 5 Baths ⋅ Lake Colony Ph 02 SubDv. ⋅ 32751 Zip Code

Priced for quick sale! Modern, mediterranean lakefront residence in one of Maitland’s most desirable GATED communities, positioned on a private cul-de-sac atop a natural rise. Set on over 1.3 acres with approximately 179 feet of frontage on Lake Jackson (ski lake), the property offers a rare combination of elevation, privacy and expansive water views in a central Maitland location with quick access to I-4, downtown Maitland and Park Avenue, Winter Park. Lake Colony Estates is conveniently located across the street from Orangewood School. The home was custom built by Keith Groninger, a 10-time Parade of Homes winner. A tree-lined drive leads to a paved driveway and a welcoming entry with imported hand-crafted 8-foot wood doors and tile roof. Inside, the foyer opens to a dramatic great room with 20-foot cathedral ceilings, clerestory windows and a floor-to-ceiling wood burning fireplace, butlers pantry and wet bar. The home has been refreshed with white interior paint, enhancing the natural light and giving the interiors a timeless backdrop. The gourmet kitchen is designed for both function and gathering, featuring 3cm granite countertops, a large island, 5-burner gas cooktop with custom stone and mortar arch detail, tumbled marble backsplash and vaulted ceilings with exposed wood beams sourced from Pennsylvania. Expansive lake-facing pocketing windows frame Lake Jackson and open the chef’s kitchen to the screened porch for effortless outdoor dining and entertaining The first-floor primary suite features engineered hardwood floors, direct access to the outdoor pool and a spacious bath finished in tumbled marble with a soaking tub, dual vanities and walk-in shower. A large custom walk-in closet provides generous storage. Upstairs, three oversized bedrooms each offer ensuite baths and a large bonus room overlooking the lake. Outdoor living is centered around the covered, screened porch, lakefront setting and gated pool. The private and expansive lawn -179 feet of shoreline, complemented by a private boathouse (newer lift) with direct access to Lake Jackson for boating, skiing, jet skis, canoes, paddleboards and more! Also, enjoy sunrise views over Lake Jackson! Additional features include two new ACs, oversized three-car garage, amazing storage and closet spaces, mature and new landscaping and carefully maintained architectural detailing throughout. Four point, roof certification and wind mitigation reports will be provided by the sellers. Seawall maintained by HOA. No flood insurance required on the home.

1244 E Lake Colony Drive, Maitland

$420,000

3 Beds ⋅ 3 Baths ⋅ Moorings On Lake Maitland Condo Bldg 04 SubDv. ⋅ 32751 Zip Code

Welcome to The Moorings on Lake Maitland, one of the most in-demand communities in the area. Consider this unit, 3-bedrooms and 2-1/2 baths, approximately 1700 square feet of living space with a 1-car garage, and overlooking the beautiful peaceful courtyard, to be your blank slate. Gleaming wood floors and fresh painted throughout, it is just waiting for you to make it your own. You'll love this comfortable living space, and there is so much to work with! From the entry foyer you'll find the eat-in kitchen immediately on your right. Head through the kitchen to the spacious dining room, and into the living room with vaulted ceiling and zen garden view. Half-bath and inviting screened lanai complete the ground floor living space. Upstairs you'll find the large primary suite, also overlooking the courtyard, and two more bedrooms, both front-facing, and a full bath in the hallway. The laundry room with washer, dryer and utility sink is in the garage. The grounds, pool and club house are maintained by the community, so all you have to so is enjoy the ambiance of the beautiful grounds and the lakefront. The many advantages to this convenient location include being on Lake Maitland, and, easy access to necessities like grocery and drug stores, and restaurants within walking distance. This one is priced to sell, so don't miss this opportunity!

245 Quayside Circle, Maitland

$497,000

3 Beds ⋅ 3 Baths ⋅ Maitland Village SubDv. ⋅ 32751 Zip Code

You've been searching for a single-family home — the space, the privacy, the pride of ownership. What if you could have all of that and never mow the lawn, pay a cable bill, or worry about the water bill again? Welcome to 2011 Michael Tiago Circle, where the spaciousness and elegance of single-family home living meets the effortless ease of a low-maintenance lifestyle — truly the best of both worlds! This stunning, move-in ready, Mediterranean-style end-unit townhome is located in the gated enclave of Maitland Village. Step inside and you'll immediately notice the soaring ceilings, extra windows of an end-unit, added natural light and elevated craftsmanship that sets this home apart: decorative chair-rail and wainscoting grace the first floor and crown molding flows throughout every level, lending an air of elegance and sophistication. The open-concept kitchen is a true showstopper, featuring granite countertops, Samsung stainless steel appliances, and 42" custom cabinetry thoughtfully designed for real life — including a pantry cabinet with pull-out drawers, a corner Lazy Susan that maximizes every inch of storage, and a dedicated pull-out trash and recycling cabinet to keep things tidy and tucked away. Whether you're hosting a dinner party or meal-prepping for the week, this kitchen is ready for it all. Sliding glass doors open to your private covered porch overlooking a serene pond— the perfect backdrop for morning coffee or evening unwinding. Upstairs, a versatile loft provides the perfect flex space for a home office, exercise space or playroom. The large primary suite features a walk-in closet and a luxurious bath with dual vanities, soaking tub, glass enclosed shower and private water closet. The other two sizeable bedrooms are down the hall for privacy and share a full bathroom. The Maitland Village HOA fee includes community gated access, swimming pool and clubhouse, lawn/shrub care, irrigation, cable/high-speed internet, water/sewer, trash/recycle pick-up and pest inspections. Conveniently located with easy access to I-4, SR 414/429 and just minutes to local parks, the Orlando Sportsplex, Maitland City Center, Winter Park and Altamonte Springs for a variety of shopping, dining and entertainment options. Make your appointment to see this beautiful home today!

2011 Michael Tiago Circle, Maitland

$467,000

2 Beds ⋅ 2 Baths ⋅ Moorings On Lake Maitland Condo SubDv. ⋅ 32751 Zip Code

Updated 2 bedroom 2 bathroom located on the second floor of sought after Moorings Lakefront Community with spectacular views of Lake Maitland of the Winter Park Chain of Lakes. The condo offers a large screened-in balcony overlooking Lake Maitland. The open floorpan offers a split plan with a generous size master retreat with a private door to the balcony and a secondary ensuite. The updated spacious kitchen features stainless steel appliances and a breakfast nook situated in a bay window. The dining living room combo is very spacious making it perfect for relaxing or entertaining. The condo offers washer and dryer in the unit as well as a private storage closet on the same floor just across the hall. The Moorings Lakefront community offers an amazing recently updated pool and spa area along a large clubhouse. Whether you're looking for a primary residence or a low-maintenance lakefront retreat, this condo and community offers an amazing combination of comfort and convenience.

204 Quayside Circle Unit 201, Maitland

$362,500

3 Beds ⋅ 3 Baths ⋅ Enclave/Maitland A-F SubDv. ⋅ 32751 Zip Code

This beautiful Maitland Florida town home feels like living in a gated resort! 3 bedrooms, 2 1/2 baths, plus garage and loaded with upgrades including hardwood floors on both levels, crown molding, tall wood cabinets, stone counters and so much more. Welcoming entry foyer with half bath, kitchen with island sink, large breakfast bar, stainless appliances, granite counters and custom backsplash. Inviting living room and dining area offer plenty of space for entertaining, french door opens to private covered porch which overlooks the rear yard. Upstairs the ensuite primary bedroom has a walk-in closet, great covered balcony area and a dual sink bathroom with glass enclosed shower. Additional 2 bedrooms in the front of the upstairs share a hall bath and laundry closet with washer and dryer included. Montacino is a gated European feeling award winning community with amazing pool area, lake frontage and a convenient location to shopping and i4. This townhouse has a quiet location within the community offering privacy in the back area. All exterior maintenance is included (roof and paint too)! HOA dues include new fiber with internet and channel package and all Montacino amenities.

1393 Benevolent Street, Maitland

$769,000

4 Beds ⋅ 2 Baths ⋅ Maitland Isle SubDv. ⋅ 32751 Zip Code

Welcome to an exceptional residence in the Maitland Isle subdivision, where timeless elegance meets modern comfort. This beautifully updated four-bedroom, two-bath home spans 2,413 square feet and offers exclusive private lake access to Lake Maitland on the prestigious Winter Park Chain of Lakes. Designed for refined living and effortless entertaining, the home features a thoughtfully curated interior with upgraded finishes, including laminate flooring, enhanced baseboards, wet bar in family room and a seamless, light-filled layout. The kitchen, enhanced with quality wood cabinetry, flows seamlessly into the main living areas, while generously sized split bedroom plan provides flexibility for family, guests or a home office. A comprehensive list of upgrades reflects pride of ownership such as a newer roof (2020), resurfaced pool (2020), advanced air-conditioning system with Enviracare Elite air purification (2019), updated electrical panels (2012), replumbing (2006) and a water heater (2022). More recent enhancements include full interior and exterior painting (2025), a newly installed wooden fence and a serviced sprinkler system with a new impeller (2026). Outdoors, enjoy a private retreat with a sparkling pool and covered deck with an outdoor entertainment area, ideal for year-round Florida living. Residents of Maitland Isle benefit from exclusive access to Lake Maitland, offering a rare opportunity for boating and waterfront recreation within one of Central Florida’s desirable communities. Ideally in a top-rated school district and just a short distance to the charm of downtown Maitland, this home delivers a lifestyle of convenience, prestige and tranquility. A rare offering where location, quality and lifestyle converge.

101 Mariner Way, Maitland

$299,000

2 Beds ⋅ 2 Baths ⋅ Sun Bay Club Condo SubDv. ⋅ 32751 Zip Code

Elegantly renovated two-bedroom, two-bath second-floor condo in the gated community of Sun Bay Club on Lake Destiny in Maitland. Vaulted ceilings and abundant windows create a bright, airy atmosphere throughout. The gourmet kitchen has been fully updated with 42-inch custom hardwood cabinets, Zodiaq (Cambrian) quartz countertops, a Kohler farmhouse sink, stainless steel appliances, and porcelain wood-plank floors. The kitchen opens to the dining and living areas, featuring a built-in desk, wood-burning fireplace, custom built-ins, clerestory windows, and triple sliding doors leading to a private balcony with a storage closet. The split floorplan includes the primary suite with a walk-in closet and a renovated bath with dual vanities, hardwood cabinets, designer fixtures, a glass-block shower, and natural light from a private skylight. The secondary bedroom has two wall closets and an upgraded bathroom with custom cabinets, a tub, and a skylight. Meticulously maintained with pride of ownership reflected throughout. Features include double-door entry, knockdown ceilings, designer finishes, ample storage, and an interior laundry closet. Additional updates include a new Carrier AC (2023), a new hot water heater (2025), and a new tile roof with gutters, downspouts, and skylights (2024). Sun Bay Club offers a beautiful lakefront pool, lake access with a boat ramp, a tennis court, a dog park, a community meeting room, and a car wash area for residents. Its central location is just minutes from I-4, RDV Sportsplex, Publix, shopping, and dining. Downtown Maitland, Winter Park, and Orlando are only a short drive away.

1000 Winderley Place Unit 239, Maitland

$250,000

2 Beds ⋅ 2 Baths ⋅ Lake Maitland Terrace Apts SubDv. ⋅ 32751 Zip Code

Welcome to Lake Maitland Terrace. Corner unit with screened in porch and lake view. As-is property.

1140 S Orlando Avenue Unit K10, Maitland

$329,900

3 Beds ⋅ 3 Baths ⋅ Villas Lake Destiny SubDv. ⋅ 32751 Zip Code

Under contract-accepting backup offers. Back on the market through no fault of the property. Recently appraised at $340,000 and inspections were completed without issue. A great opportunity for a qualified buyer seeking a smooth transaction and quick closing. Tucked into one of Maitland's most coveted lakefront enclaves, this beautifully updated townhome sits within a quietly maintained, tree-lined setting with direct access to Lake Destiny, a private community boat ramp, resort-style pool, and tennis courts, all just minutes from I-4, the 414, RDV Sportsplex, and the dining and shopping corridors of Maitland Center. First impressions set a private and secluded tone with a wrought-iron gated courtyard leads to a covered entry porch before you reach the front door. Inside, soaring vaulted ceilings and a dramatic arched transom window above the sliding glass doors flood the main level with natural light, creating an airy, open feel that far exceeds the square footage on paper. Wide-plank tile flooring runs throughout the main living areas, connecting the open living and dining spaces to a thoughtfully updated kitchen featuring white shaker cabinetry with crown accents, solid stone countertops, stainless steel appliances including a French door refrigerator and built-in microwave, pendant lighting above the breakfast bar peninsula, and a subway tile backsplash. The sliding doors open directly to a private screened patio framed by mature landscaping, creating the kind of indoor-outdoor flow that defines Florida living at its best. Upstairs, three generously sized bedrooms each offer ceiling fans, ample closet space, and brand new carpet and paint. The primary suite stands out with a 26ft footprint, two closets including a walk-in, and an ensuite bath featuring dual vanities, a full-wall vanity mirror, and a walk-in shower. Two additional bedrooms and a full bath complete the upper level, with the layout providing genuine separation and privacy between spaces. Back on the main floor, a versatile 9x9 bonus room with indoor laundry handles the day-to-day, and the full-size washer and dryer convey. The big-ticket items are handled: 30-year tile roof replaced in 2023, HVAC installed in 2020, and brushed nickel fixtures updated throughout. The one-car garage with additional driveway parking and the gated courtyard entry give this unit a sense of privacy and security rare in townhome living. Whether you are looking for a low-maintenance primary residence, a lock-and-leave second home, or a smart investment in a well-managed community with real amenities and a lakefront address, this one makes an easy case.

1010 Winderley Place Unit 127, Maitland

$485,000

3 Beds ⋅ 3 Baths ⋅ Enclave/Maitland A-F SubDv. ⋅ 32751 Zip Code

Welcome to this beautiful Mediterranean-style townhome in the exclusive, gated community of Montacino in Maitland, Florida. Updated 3 bedroom, 2.5 bath home overlooking Lake Charity. Expansive views of the lake are seen from the front porch, two bedrooms and the dining room. Separate dining room with tons of natural light. Open concept kitchen with updated cabinets and stainless steel appliances. The large family room is open to the kitchen for ease of entertaining. Situated between the garage and your back door is an open air, private courtyard. Enjoy a two and a half car garage with full attic for additional storage. The second floor includes three bedrooms, finished laundry with closets that have been professionally customized. Secondary bedroom boasts a Murphy bed for guests with build-in storage. You will enjoy resort style living with the sparkling community pool and tranquil walks along the shores of Lake Charity. Extra guest parking is located just outside the garage. Internet/TV package and lawn care included. Located just 1/4 mile from I-4 and the Maitland Boulevard exchange with easy access to Winter Park, downtown Orlando and Altamonte Springs. Close by is Trelago Market where the new Trader Joes is being built. A must see property.

1106 Charming Street, Maitland

$599,000

2 Beds ⋅ 2 Baths ⋅ West Cove Condo SubDv. ⋅ 32751 Zip Code

TURN KEY AND RENOVATED IN SOUGHT-AFTER WEST COVE!! Wake up to breathtaking sunrises with a stunning, unobstructed view stretching across Lake Maitland—the largest lake in the highly sought-after Winter Park Chain of Lakes—from this beautifully renovated, truly turnkey condominium. All flooring, bathrooms, fixtures, paint, AC, water heater, sliding door to balcony, kitchen/appliances, and closet systems have been painstakingly updated to the highest level, making for an unparalleled opportunity to simply move right in and begin enjoying immersive lake views. The primary suite has been reimagined and has its own ensuite bath and a new built-in closet with copious storage, complete with signature views of Lake Maitland. This spacious residence offers an ideal central location, just moments from an array of dining options, Lake Lily Park, Enzian Theater, and convenient access to Interstate 4 via Lee Road or Maitland Boulevard. The monthly association fee—lower than most lakefront communities—provides exceptional value and includes access to lakefront docks (with boat slips available on a first-come basis), a fitness center, an inviting lobby for entertaining, a heated pool and spa, a grilling area with seating, storage for canoes, kayaks, and paddleboards, assigned and guest parking, laundry facilities on every floor, Spectrum cable and internet, as well as water, sewer, and trash services. This property may be under audio/visual surveillance.

1100 S Orlando Avenue Unit 306, Maitland

$745,000

4 Beds ⋅ 3 Baths ⋅ Dommerich Estates 1st Add SubDv. ⋅ 32751 Zip Code

In the heart of Dommerich, this thoughtfully renovated mid-century pool home offers deeded access to the Winter Park Chain of Lakes & a well-executed floor plan designed for everyday living. Set on a .20-acre lot measuring 79’ x 111’, the home balances indoor comfort with outdoor livability, beginning with a welcoming front entry that opens to a casual foyer. To the left is a shared formal living and dining space filled with natural light from large-format windows. Wide plank engineered wood flooring, charming built-ins & updated finishes continue throughout the main living areas, creating a cohesive & visually consistent interior. Toward the back of the home, the layout transitions to a family room & adjoining Florida room, which, when used together, create a spacious secondary living area, or may function separately as a family room, casual dining area, office or reading room, all overlooking the pool and functionally connected to the kitchen. The kitchen is positioned at the center of the home & features white shaker cabinetry, grey quartz countertops, a large island with a butcher block countertop, seating and storage on all sides, a vent hood over the range, stainless steel appliances & a large white ceramic single-bowl farmhouse sink with a pull-down commercial-style faucet, along with windows overlooking the pool & backyard. The home offers an ideal split-bedroom plan, with the primary suite located on the back left side of the home and added in 2018 by Winter Brothers Construction. The suite includes a spacious bedroom with recessed lighting, separate closets with built-in organization & a well-appointed bath with dual vanities, a freestanding soaking tub, a glass-enclosed walk-in shower with rain shower head & a private water closet. On the opposite side of the home are three additional bedrooms, including one with an en-suite bath designed with a pedestal sink, wall-mounted storage & a glass-enclosed walk-in shower, along with a full hall-entry bath which comes with a tub/shower combination & new vanity (2026). Highlights of the backyard include a paver deck, saltwater swimming pool with a generous shallow shelf, child safety fence, play set, raised garden bed, lawn space for people and pets and a mature peach tree that produces fresh peaches. The home also features an attached two-car garage with a laundry area, professional landscaping and a newly installed white privacy fence with gated access on both sides. In addition to its charm & interior updates, the home offers meaningful system improvements, including electrical panels (2018), two HVAC systems (2018 and 2022), a full re-pipe to PVC/CPVC, roof replacement (2017–2018) & an electric water heater (2018). The property owner has the option to join the Dommerich Estates Beach Civic Association, which provides access to a private boat ramp, picnic area and lakefront amenities on Lake Minnehaha. Residents also enjoy convenient access via the neighborhood boardwalk to Maitland Community Park, offering tennis and basketball courts, trails, pavilions and year-round activities. Zoned for Dommerich Elementary, Maitland Middle and Winter Park High and located just minutes to Park Avenue, Lake Lily, the Maitland SunRail station and major roadways, this is an opportunity to own a move-in ready home in a well-established neighborhood with strong school zoning, a true sense of community and lake access to the Winter Park Chain of Lakes.

150 Seneca Trail, Maitland

$324,000

2 Beds ⋅ 2 Baths ⋅ Maitland Harbour Apts SubDv. ⋅ 32751 Zip Code

Offered at a newly improved price, this highly desirable residence at Maitland Harbour is located within a boutique 38-unit lakefront condominium community nestled in the heart of Maitland. Ideally positioned on Lake Maitland—the largest lake on the Winter Park Chain of Lakes—this intimate and picturesque enclave offers access to the entire chain and a truly exceptional waterfront lifestyle. A hidden gem, Maitland Harbour blends timeless Mid-Century Modern architecture with the serenity of lakefront living. Designed by renowned architect Manfred Lopatka, a protégé of Frank Lloyd Wright, and built in 1964, the community reflects a distinctive Central Florida interpretation of classic modernist design. Inside this beautifully updated 2-bedroom, 2-bath residence offering 952 square feet, you will find light-filled living space with a clean, cohesive aesthetic throughout. The kitchen, renovated in 2020, features quartz countertops, a subway tile backsplash, open wood shelving, and a pass-through to the dining area, creating both functionality and visual connection to the main living space. The open-concept living and dining areas are bright and inviting, with warm-toned wood flooring and neutral finishes. The primary suite is a true retreat, complete with updated flooring (2020), soft natural light, newly added barn-style closet doors for improved storage access, and direct access to the private balcony—ideal for enjoying morning coffee or evening breezes. The en-suite bath, renovated by a previous owner, features neutral finishes and a glass-enclosed shower. The secondary bedroom is spacious and offers consistent updated flooring and fresh paint, and is located adjacent to a full guest bath with recent updates including vanity, lighting, and fixtures. Additional improvements include a new refrigerator (2023), new windows (2024), new HVAC (2025), and fresh interior paint (2025/2026). The community has completed major improvements including new roofs, pool enclosure, and exterior paint, and both the milestone inspection and structural integrity reserve study have been completed and are available for review. Residents enjoy a full suite of lakefront amenities including a waterfront pool, courtyard, boat slips, fishing pier, kayak storage, community room, private storage, covered parking, and an expansive entertaining deck overlooking Lake Maitland. The location is adjacent to historic Fort Maitland Park and directly across from Lake Lily, the heart of Maitland’s Cultural Corridor, known for concerts, the Maitland Art Festival, and the Sunday Farmers Market, and is just a short walk to the Enzian Theater and local dining, with easy access to Winter Park’s Park Avenue offering premier shopping, restaurants, museums, and year-round events. Enjoy low-maintenance lakefront living with beautiful interior spaces, a private balcony, and access to one of Central Florida’s most sought-after waterfront settings.

1000 S Orlando Avenue Unit B25, Maitland

$649,000

3 Beds ⋅ 2 Baths ⋅ N/A SubDv. ⋅ 32751 Zip Code

Virtually Staged. FINAL SUBMISSION WINDOW – SELLER HAS SET A FIRM DEADLINE TO SECURE CONTRACT. ALL PROPOSALS DUE MAY 11. FULLY RENOVATED Maitland home offered for a limited time only. Seller will review all submitted contracts, including those below list price, and is open to structuring terms that work - including potential closing cost assistance or rate buydown with acceptable terms. Contracts must be submitted by May 11. Seller will make a decision immediately thereafter. This property will be removed from the market if not sold by the deadline. MAJOR PRICE IMPROVEMENT Fully reimagined designer pool home with deeded access to skiable Lake Seminary, offering a rare blend of modern luxury, privacy, and prime Maitland location. Tucked away in a peaceful setting, this home lives like a private retreat while remaining just minutes from everything Maitland and Winter Park have to enjoy. At the heart of the home is a true showpiece kitchen, thoughtfully designed with a striking waterfall-edge island, full-height quartz backsplash, beverage fridge, and a clean, modern aesthetic reminiscent of a custom build. The open-concept layout is filled with natural light and flows effortlessly into the main living spaces—perfect for both elevated entertaining and everyday living. The primary suite delivers a spa-inspired retreat, featuring a freestanding soaking tub, oversized walk-in shower with dual heads, and carefully curated designer finishes that create a true sense of escape. Step outside to your own private backyard oasis, complete with a sparkling pool, expansive paver patio, and newly fenced yard—designed for both relaxation and hosting. The oversized lot offers exceptional flexibility, with ample space to add a garage, guest house, or additional storage to suit your needs. This home has been fully renovated with a strong emphasis on quality craftsmanship and high-end finishes throughout, including a new roof, HVAC, windows, flooring, and more—offering true move-in-ready peace of mind. Enjoy deeded access to skiable Lake Seminary via recorded easement—an exceptional and increasingly rare feature in this area. Buyer to verify access and use. Conveniently located near Maitland and Winter Park, with easy access to shopping, dining, and major roadways—giving you the perfect balance of privacy and accessibility.

106 Oakwood Drive, Maitland

$799,000

4 Beds ⋅ 2 Baths ⋅ Maitland Grove SubDv. ⋅ 32751 Zip Code

Under contract-accepting backup offers. ENTERTAINING MAITLAND GROVE POOL HOME. Step inside to discover oversized rooms, including a spacious great room overlooking the covered lanai and swimming pool in a private setting perfect for gatherings. Back yard includes a vinyl privacy fence, Pool resurfaced with Pebble Tec. Patio and pool decking have pavers with plenty of room for extra lounging. Lots of Room for everyone, including lIving Room, Dining Room and 4 bedrooms. Kitchen features all new SS appliances and sink w/ faucet, a separate breakfast room and laundry room. Primary room features en suite updated bathroom with dual vanity, shower, w/ tub, walk in closet and large slider doors overlooking the serene pool. Home offers lots of closet and ample storage. Extra Long driveway with side entry oversized garage includes utility sink. Home has been lovingly cared for. Call to view today!

320 White Oak Circle, Maitland

$988,000

4 Beds ⋅ 3 Baths ⋅ Wellington SubDv. ⋅ 32751 Zip Code

Welcome to this stunning home in Maitland, located at 1817 Braeloch Ct. A welcoming foyer opens to elegant formal living and dining rooms featuring gorgeous fixtures, plantation shutters throughout, 5½-inch baseboards, and beautiful manufactured wood flooring. Vaulted ceilings and skylights fill the home with natural light, while a cozy wood-burning fireplace and stylish wet bar create the perfect setting for entertaining. The completely renovated kitchen by Braden Kitchens offers abundant cabinetry and storage, with even more storage available in the spacious laundry room. The luxurious primary suite has been fully updated and features a beautifully redone bathroom and a custom built-in closet system. Step outside to a private screened pool and an impressive redesigned porch with pavers, vaulted ceilings, and skylights—perfect for relaxing or hosting guests. The home also includes a convenient half bath, two additional bedrooms with walk-in closets, a second bathroom that serves as a pool bath with a shower and linen closet, and a third bedroom with French doors leading directly to the pool area. Additional highlights include a central vacuum system, an oversized two-car garage, a shingle roof installed in 2021, A/C (2018), and a newer water heater for peace of mind. Residents also enjoy HOA community access to a private boat ramp and dock on the lake, which features a private skiing and slalom course. Boat storage at the private dock may also be available for an additional $100 per year, offering even more convenience for enjoying the Florida waterfront lifestyle.

1817 Braeloch Court, Maitland

$885,000

4 Beds ⋅ 3 Baths ⋅ Dommerich Estates 1st Add SubDv. ⋅ 32751 Zip Code

Welcome to your dream home! This beautifully updated 4-bedroom, 3 bath residence is in one of the area's most desirable neighborhoods. Enjoy a perfect blend of comfort, style, and functionality, complete with modern renovations and exceptional outdoor living spaces. This corner lot home with multiple picturesque windows provides an abundance of natural light! Generously sized bedrooms provide ample space for family, guests, or a home office and include 2 master suites, both with 2 closets. Enjoy cooking and entertaining in the stunning, updated kitchen featuring modern appliances, sleek countertops, and plenty of storage. Luxury vinyl flooring throughout but still the charm of original wood floors in 3 of the bedrooms. Step outside to your own backyard oasis with a sparkling pool with a waterfall feature and paver patio, perfect for relaxing or hosting gatherings. Eco-friendly and convenient, the property includes an electric vehicle charging station. Tucked away yet ready in a moment’s notice is space for your boat, camper, or recreational vehicles. The attached one car garage offers secure storage for tools, bikes, toys, golf cart, hobbies or projects. You are just steps from the neighborhood lake lot where members can enjoy incredible sunsets, fishing, or launch your watercraft and enjoy a day on the lake. Dommerich Estates has a strong sense of community and was designed and built around A rated schools so walking and biking to school is safe and easy. The City of Maitland, despite its close proximity to Orlando, is vibrant with a small-town feel providing events designed to foster connections among residents with walkable neighborhoods, multiple parks and downtown street parties and concerts!

535 Pawnee Trail, Maitland

$415,000

2 Beds ⋅ 1 Baths ⋅ Lake Maitland Terrace Apts SubDv. ⋅ 32751 Zip Code

Experience turn-key living at its best in this beautifully renovated, designer-owned, lakefront condo, conveniently located in the sought-after Lake Maitland Terrace community on the Winter Park Chain of Lakes. This stunning 2-bedroom, 1-bath residence was thoughtfully redesigned with high-end finishes and an open, modern layout that maximizes both style and functionality. FURNITURE IS NEGOTIABLE! The completely updated interior features luxury “wood-like” vinyl plank flooring throughout, for enhanced durability. Enjoy a stylish kitchen with custom cabinetry, quartz countertops, tile backsplash, and newer appliances, and a beautifully remodeled bath with marble herringbone tile and designer fixtures. Additional upgrades include all new electrical, recessed lighting with dimmers, updated plumbing, custom closets, shiplap accents, new interior doors and trim, high-end Emtek door knobs throughout, and sound-reducing flooring underlayment for added comfort. Lake Maitland Terrace offers a true lakefront lifestyle, with private access to Lake Maitland, the largest lake on the Winter Park Chain. Residents enjoy a community dock and fishing pier, kayak & paddleboard racks, a sparkling pool, a clubhouse with lake views, shuffleboard courts, bike storage, and convenient on-site laundry....but this unit has it's OWN Washer and Dryer! Ideally located near shopping, dining, theaters, and just minutes from Park Avenue in Winter Park, this fresh and modern move-in ready condo offers effortless living in one of Maitland’s most desirable waterfront communities. Don't forget.... the FURNITURE IS NEGOTIABLE!

1140 S Orlando Avenue Unit H-13, Maitland

$325,000

2 Beds ⋅ 2 Baths ⋅ Lake Maitland Terrace Apts SubDv. ⋅ 32751 Zip Code

This luxury condominium is in the established complex of Lake Maitland Terrace which sits on the shores of Lake Maitland, Winter Park Chain of Lakes. This immaculately maintained complex includes 11, 2-story, mid-century modern buildings sprawled across several acres, creating beautiful green space and picturesque views across the lake. This unit is special. A complete renovation with every detail accounted for, it is turnkey with enduring design. Warm wood floors are carried through spaces, kitchen has been opened to living room and flanked with windows allowing natural light to shine. Kitchen features white 42-inch shaker style cabinetry, quartz counters, subway tile backsplash, open shelving and stainless appliances. Counter seating is inviting and creates great kitchen function with loads of counter space for the aspiring chef. Primary suite is spacious with large closet storage, and renovated bath. Secondary bedroom and additional bath add to the flexibility of the unit, a guest room or home office. Indoor laundry makes this lock-and-go lifestyle even more appealing. Custom window treatments, closet system storage, updated HVAC, and fresh paint throughout. The location is pristine with walkability to the Enzian independent theatre, Lake Lily Park with a recreational trail and park, and home to community events, many restaurants and more. A short distance to Winter Park Village and Park Avenue and zoned for incredible schools with Dommerich Elementary, Maitland Middle & Winter Park Highschool. Complex is amenity-rich with sidewalks, community pool, generous dock, shuffleboards and more. Make this rare opportunity yours to own a little slice of this Maitland treasure.

1140 S Orlando Avenue Unit F11, Maitland

$504,000

2 Beds ⋅ 2 Baths ⋅ Moorings On Lake Maitland Condo Bldg 03 SubDv. ⋅ 32751 Zip Code

LAKEFRONT PARADISE ON LAKE MAITLAND AND THE WINTER PARK CHAIN OF LAKES. Cue the Jimmy Buffett music as you arrive home to your own serene tropical lakefront paradise here at The Moorings on Lake Maitland. The pace feels a bit more relaxed here on the water! This beautiful, move-in ready FULL lakefront condo is located on the third floor of building 3 which is closest to the water. Imagine every day feeling like a tropical vacation in this coveted community with no outside maintenance for you to tend to. Step onto the elevator and effortlessly arrive at your front door. Step inside to find breathtaking panoramic views of sparkling Lake Maitland through oversized glass doors leading to your own private balcony. Enjoy lake views from every single room, even from both bathtubs! Start your mornings with quiet reflections on your peaceful balcony with the soothing sounds of nature and the lake waters gently lapping on the shoreline. Wind down your evenings visiting with friends on the community lawn or expansive dock under painted skies with cool lake breezes. Launch a kayak from the community dock and explore the wonders and natural beauty found throughout the coveted Chain of Lakes. Have your own boat? Newly renovated Fort Maitland Park is next door with day parking and a convenient boat launch. And from time to time, it’s possible that a private boat slip at The Moorings could come available for private purchase or lease. The spacious interior of this condo offers a pleasing neutral color palette with luxury vinyl wood flooring in the living area and primary suite. Attractive oversized tile graces the foyer, kitchen, dining alcove, bathrooms, and balcony. The current décor leans into a vintage Florida tropical vibe allowing you to easily envision the vacation-every-day-feeling! The spacious foyer includes a walk-in storage closet. The well-appointed kitchen is outfitted with custom wood cabinetry, gorgeous granite counters, stainless appliances, a closet pantry in the hall, and glorious water views from the large pass-through opening with breakfast bar. Dine with friends surrounded by water views from the dinette, from the main dining area (currently used as additional living area), or from your balcony. No worries about lugging laundry to a community space--enjoy a double door laundry closet. The combo living dining area is currently set up as all living space providing wonderful entertaining and lounging opportunities. Wake up every morning to serene water views in this private primary suite with double windows for unobstructed views and French door access to the balcony. The beautiful en-suite has a granite dual sink vanity, walk-in closet, and a garden soaking tub and shower with water views as well! Imagine the relaxing baths you could have here! BR two has cozy carpet and a double door closet with easy access to the hall bath with granite sink vanity and a tub/shower. This is a tranquil community with abundant privacy, but opportunities abound for connection if you’d like. The clubhouse has regular gatherings and events, and the recently refurbished pool and spa are ideal for total relaxation or for connecting with friends. Popular restaurants such as Luke’s, Antonio’s, and Athena’s are found just outside the community and a stone’s throw will land you at Enzian Theater with Eden Bar, the Maitland Art Center, all of the wonderful cultural venues and retail establishments of Winter Park and Orlando, and so much more. Welcome home!

206 Quayside Circle Unit 302, Maitland

$725,000

4 Beds ⋅ 3 Baths ⋅ Dommerich Estates 2nd Add SubDv. ⋅ 32751 Zip Code

Virtually Staged. ONE OF A KIND for Dommerich Estates, this LAKE VIEW Home is designed for soaking in unforgettable sunsets and unwinding after a long day. Located directly across the street from the neighborhood lake lot, you will enjoy unobstructed views of the water, easy access to the boat ramp and fishing dock or launch your canoe or kayak for a peaceful paddle on the lake that also connects to the Winter Park Chain of Lakes! 4 generous bedrooms and 3 baths provide plenty of space for family and guests. Beautiful wood floors flow throughout and are complemented by crown molding for a classic touch. The spacious living room has a wood-burning fireplace and built-in cabinets to display all your treasures. It’s also large enough to be used for a combination living room/dining room and enjoy the lake views while you dine. The open kitchen and family room look out onto the screened patio and pool with a relaxing water feature. Feel secure during hurricane season with an installed and powerful Briggs and Stratton generator that will keep the power going to the kitchen, 4th bedroom and bath during the storm! Upgraded electrical system and the home has been replumbed for your peace of mind. Dommerich Estates has a strong sense of community and was designed and built around A rated schools so walking and biking to school is safe and easy. Social events at the lake lot provide a fun opportunity for neighbors to meet neighbors and there is a boardwalk that connects you to Maitland Park with playgrounds, tennis courts, walking trails and basketball courts. The City of Maitland is vibrant with a small-town feel providing events designed to foster connections among residents with multiple parks and downtown events and concerts! Don’t pass on this opportunity to own this rare, lake view home in one of the best neighborhoods in the area!

570 Dommerich Drive, Maitland

$1,825,000

4 Beds ⋅ 4 Baths ⋅ Maitland Cove SubDv. ⋅ 32751 Zip Code

Welcome to a rare opportunity on the shores of Lake Sybelia, one of Maitland’s most desirable recreational lakes. This custom, one-owner home offers 3,754 square feet of thoughtfully designed living space that has been well-maintained with potential for cosmetic enhancements. A brick-paved horseshoe driveway and inviting front porch set the tone. Inside, rich wood floors, vaulted wood ceilings in the living and family rooms, two fireplaces, and custom built-ins showcase quality rarely found today. The spacious layout features four bedrooms and 3.5 baths, including two primary suites ideal for multi-generational living. Generous walk-in closets and a blend of wood, tile, and carpet add comfort and function. A new A/C (Oct 2025) and a 6.5-year-old roof provide peace of mind. Living areas open to a bright rear sunroom with tranquil lake views. Whether you’re entertaining by the fire, enjoying coffee on the porch, or heading out onto the lake, this property delivers the Florida lifestyle at its finest.

1111 Audubon Way, Maitland

$226,000

2 Beds ⋅ 1 Baths ⋅ Lake Maitland Terrace Apts SubDv. ⋅ 32751 Zip Code

Welcome to Lake Maitland Terrace Condominiums — where lakefront living meets modern comfort in the heart of Maitland. This beautifully renovated 2-bedroom, 1-bath condo offers stylish, move-in-ready living just steps from the shores of Lake Maitland, part of the coveted Winter Park Chain of Lakes. Inside, you’ll find luxury vinyl plank flooring throughout, creating a seamless and contemporary feel. The updated kitchen and bathroom feature elegant stone countertops, complemented by plantation shutters that add timeless charm and privacy. A new storm door enhances both curb appeal and energy efficiency, while major systems have already been taken care of — with a water heater from 2023 and a brand-new HVAC system installed in 2025 for peace of mind. Beyond your front door, enjoy private access to a large community dock on Lake Maitland — perfect for soaking in sunset views, boating, or simply enjoying the tranquil waterfront setting. Residents also enjoy a variety of amenities including a sparkling pool, clubhouse, shuffleboard courts, and even a putting green for relaxed afternoons close to home. Location is everything, and this condo delivers. Just down the street, the new Life Time Winter Park luxury Athletic Country Club is set to open in May 2026, bringing premier fitness, wellness, and social experiences right to your doorstep. Whether you’re looking for a primary residence, seasonal retreat, or low-maintenance investment, this fully updated lakefront condo offers an exceptional opportunity in one of Maitland’s most desirable communities.

1140 S Orlando Avenue Unit E13, Maitland

$235,000

3 Beds ⋅ 3 Baths ⋅ Park Lake Grove Condo Ph D SubDv. ⋅ 32751 Zip Code

Now is your chance...3 BR 3 BA Townhome great location close to I-4 and 17/92, Community pool, newer roof (4 yrs) Quiet dead end Street Enter through gate or garage door. Back door opens to laundry room with brand new water heater, brand new garage door opener and a washer and dryer, then into the galley kitchen with a new stainless steel fridge. You have a dining room living room combo and one bedroom and full bath on first floor. Lots of closet space. Front door opens to wooded area and small front porch. Upstairs there are 2 bedroom suites. One bath has shower one with tub. One offers a balcony with lake view overlooking green area. Big closets. Brand new carpet staircase and upstairs bedrooms. This home is close to fine dining restaurants, shopping, hospital, winter Park Village and downtown Maitland Lake Lily and 2 farmers markets. Nice quiet walkable neighborhood.

1550 Gulfview Drive Unit 444, Maitland

$448,500

2 Beds ⋅ 2 Baths ⋅ Moorings On Lake Maitland Condo SubDv. ⋅ 32751 Zip Code

Seller to pay up to one year of HOA! Wake up to shimmering lake views and unwind each evening with breathtaking Florida sunsets in this beautifully refreshed 2-bedroom, 2-bathroom condo. From the moment you step off the elevator, you’re welcomed into a light-filled, open-concept living space highlighted by oversized glass sliding doors that lead to a private enclosed patio—seamlessly blending indoor and outdoor living. The kitchen is both bright and inviting, featuring upgraded cabinetry, a spacious eat-in area, and a large island designed for effortless entertaining. Thoughtful updates throughout include upgraded flooring, brand-new carpet installed just six months ago, and a newer AC unit replaced two years ago for added comfort and peace of mind. Custom-tailored curtains complete the space with a refined, polished finish. cThe primary suite offers a quiet, private retreat with its own bath, while the split-bedroom layout ensures comfort and privacy for guests. Life at The Moorings is centered around a relaxed, lakeside lifestyle—complete with a community pool, heated spa, clubhouse, lushly landscaped grounds, and direct access to Lake Maitland on the Winter Park Chain of Lakes. Spend your days on the lakefront dock or hosting poolside gatherings, then enjoy the convenience of walking to local favorites like Luke’s and Antonio’s or exploring Maitland’s newly designed downtown with green spaces, farmers markets, and vibrant community events.

204 Quayside Circle Unit 504, Maitland

$1,090,000

5 Beds ⋅ 5 Baths ⋅ Wellington SubDv. ⋅ 32751 Zip Code

HARD TO FIND SKI LAKEFRONT! Classic traditional beauty – ready for a lucky buyer to make home. Stunning water & sunset views over Lake of the Woods from most living areas. Enter into the impressive foyer with curved stairway; light & bright large formal rooms with French doors to wrap around covered porch; Large open kitchen, wood cabinets, granite tops, stainless appliances and breakfast nook to sip coffee and bird watch! Inviting family room with fireplace and custom built in surrounds. First level guest suite and full bath; elevator serves to 2nd level huge Master suite, with open deck and lake views; Master bath, dual vanities, Jacuzzi tub and shower, walk in closet. 2 additional large sunny bedrooms share Jack & Jill bath, 3rd upstairs bedroom is ensuite with a large walk in closet. Lovely landscape provides privacy and beauty. New boathouse and dock are ready for action! Super side entry 3 car garage, storage, huge utility room. Survey, pool plan available. Seminole County Schools PLUS excellent Private Schools within a few miles. Neutral colors, tile roof. Bring your water skis, knee boards, fishing poles & kayaks! Sold As-is; seller may consider decor credit with acceptable offer!

1256 Wellington Terrace, Maitland

$130,000

1 Beds ⋅ 1 Baths ⋅ Visconti West Condo SubDv. ⋅ 32751 Zip Code

Virtually Staged. Water views, major system upgrades, and the best value in Visconti. This beautifully updated 1-bedroom, 1-bath condo is priced $16,000 below the next comparable unit in the community and features over $15,000 in recent improvements, including a brand-new Goodman 2-ton 14.3 SEER HVAC system (2025), a new water heater with an expansion tank (2026), and stylish shaker kitchen cabinets (2025). Enjoy tranquil pond views from both the living room and bedroom, with a large sliding glass door leading to your private balcony. The open-concept layout offers abundant natural light, built-in shelving, and a functional floor plan designed for comfortable everyday living. A separate laundry room adds extra convenience and storage. Located within the gated Visconti community, residents enjoy resort-style amenities including two swimming pools, a fitness center, clubhouse, tennis and basketball courts, and scenic paths. HOA fees include water, sewer, and trash service. Conveniently located just minutes from I-4, Downtown Orlando, Winter Park, Altamonte Springs, major employers, shopping, dining, Walt Disney World, Universal Orlando, and Orlando International Airport. Whether you're a first-time homebuyer, downsizing, or seeking a low-maintenance investment property, this move-in-ready condo offers exceptional value and location. Mortgage savings may be available for buyers of this listing.

1275 Lake Shadow Circle Unit 13206, Maitland

$365,000

2 Beds ⋅ 2 Baths ⋅ Lake Maitland Terrace Apts SubDv. ⋅ 32751 Zip Code

This condo was completely renovated in 2023 and is located in one of the best spots within the complex. Positioned directly on the Winter Park chain of lakes, it offers excellent access to everything Winter Park and Maitland have to offer. Residents enjoy being within walking distance to a variety of restaurants and shopping, creating an ideal blend of convenience and lifestyle. This unique corner unit features great views and a screened-in porch on the first floor, perfect for enjoying the surroundings. Because it is a corner residence, the condo is filled with lovely natural light from multiple windows, enhancing the open feel. Its location also provides easy access to the pool area for added everyday convenience. Inside, the condo offers two full baths and extensive upgrades throughout. Raised ceilings contribute to the spacious atmosphere, while newer electrical, plumbing, and a hot water heater provide peace of mind. The home includes newer full-sized appliances, custom cabinetry, granite countertops, newer flooring, custom closets, and an in-unit washer and dryer. Residents enjoy lake access with beautiful views and the community amenities include a clubhouse with a full kitchen, kayak racks, a fishing pier, and a personal storage unit. With renovations completed in 2023, the condo features modern finishes and systems that feel fresh and move-in ready.

1140 S Orlando Avenue Unit F-1, Maitland

$364,000

3 Beds ⋅ 3 Baths ⋅ Enclave/Maitland A-F SubDv. ⋅ 32751 Zip Code

BELOW APPRAISAL + SELLER OFFERING INTEREST RATE BUY-DOWN with acceptable offer. /// Why settle for "standard" when you can own a designer-caliber home in Maitland with a lower monthly payment? Priced at $369,000—well below the recent $384K appraisal—this high-end unit offers instant equity. *LIFESTYLE & LOCATION /// RECLAIM YOUR TIME: Just 10 minutes to Downtown Orlando or Winter Park. PET FRIENDLY: Montecino is a gated, pet-loving community. LAKE CHARITY: Enjoy a scenic walk right outside your door. Maintenance-free living with a resort-style pool and gated security. *UPGRADES & VALUE /// MECHANICALLY NEW: New HVAC (Jan 2025), Bosch dishwasher, and 2026 fridge/microwave. DESIGNER FINISHES: Engineered hardwoods, fresh paint, and designer lighting. HOA BONUS: Monthly dues include High-Speed Internet, WiFi, and expanded TV/Streaming.*PEACE OF MIND /// Home just passed INSPECTION. Between the verified value, mechanical updates, and potential interest rate buy-down, this is the most secure and affordable luxury entry in Maitland. Also available for rent at $2500/month. Seller seeking a long-term, high-quality tenant.

1321 Benevolent Street, Maitland

$689,000

4 Beds ⋅ 3 Baths ⋅ Dommerich Hills 2 Nd Add SubDv. ⋅ 32751 Zip Code

Priced below Appraised Value — and the seller is ready to move. This classic 4-bedroom, 2.5-bath Maitland pool home sits on a spacious quarter-to-half-acre lot with peaceful lake views and delivers 3,000 square feet of open, comfortable living. The updated kitchen and open floor plan make the interior as functional as it is inviting, but the real showstopper is outside — a sparkling pool (Resurface 2025) and generous outdoor living area with a lake backdrop that makes every evening feel like a retreat. The big-ticket items are already handled: 7-year roof, 7-year AC, updated plumbing, and a fully paid-off solar system that virtually eliminates your monthly electric bill — and under Florida law, it won't raise your property taxes. Zoned for top-rated schools and just minutes to Winter Park's dining, shopping, and culture. This is a home with more value than the price tag suggests. Motivated seller. Bring your

2514 Tuscarora Trail, Maitland

$690,000

2 Beds ⋅ 2 Baths ⋅ Moorings On Lake Maitland Condo Bldg 03 SubDv. ⋅ 32751 Zip Code

Luxury lakefront living at its finest awaits at "The Moorings" on Lake Maitland Chain of Lakes. Perfectly positioned on the first floor, this stunning two-bedroom, two-bath residence offers breathtaking lake views from nearly every room, creating a serene and sophisticated backdrop for everyday living. Completely renovated with impeccable attention to detail, the home features designer epoxy flooring throughout the main living areas and luxury statement lighting that elevates the space with warmth and style. The living room invites relaxation with a sleek electric fireplace and expansive glass sliders that open to an extra-large lanai overlooking Lake Maitland—an ideal setting for morning coffee, evening sunsets, or effortless entertaining. The state-of-the-art chef’s kitchen is a true showpiece, thoughtfully designed for both beauty and function. It includes modern quartz countertops, a smart refrigerator with TV, with AI vision that updates your shopping list, planning and interactive features, a wine refrigerator, new stainless steel appliances, a vented hood, cooktop with pot filler, Bosch dishwasher, and a double oven with convection microwave combination and convection oven—perfect for hosting and everyday luxury. A discreet pantry closet houses a stackable washer and dryer, seamlessly integrating convenience into the design. The primary suite is a tranquil retreat with stunning lake views and a custom walk-in closet system complete with jewelry drawer, laundry bins, and generous storage. The spa-inspired primary bath features dual quartz vanities, a frameless glass shower, and a luxurious rain shower head, while the high-end bidet toilet automatically opens upon entry for an added touch of modern indulgence. The guest suite is equally impressive, featuring a custom Murphy bed with integrated storage and desk, dresser, television, and elegant glass closet doors. The adjacent guest bath has been fully reimagined as a spa sanctuary with a jetted soaking tub, designer tile, a custom light-up mirror, and new quartz top vanity. Storage is abundant throughout the home, including a coat closet, a hidden hideaway closet concealed behind a custom bookcase, and thoughtfully designed built-ins that maximize space without sacrificing style. Residents of "The Moorings" enjoy exceptional community amenities, including a resort-style pool with spa and a clubhouse ideal for private parties and social gatherings. The community is impeccably maintained, featuring new exterior paint and seal, a newer roof, and beautifully maintained landscaping, reflecting true pride of ownership. Additional features include a security system, smart thermostat, newer AC, and newer appliances, offering peace of mind and energy efficiency. For outdoor enthusiasts, the community allows storage for kayaks and paddleboards, with boat slip #16 available for rent, providing direct access to the Chain of Lakes lifestyle. Ideally located near Lake Lily’s Farmers Market, popular restaurants, extensive shopping, bus routes, and with easy access to I-4, this home is also zoned for top-rated A+ schools—blending luxury, convenience, and lifestyle into one exceptional offering. This is more than a home—it’s a refined lakeside retreat where comfort, design, and location come together beautifully.

206 Quayside Circle Unit 103, Maitland

$650,000

4 Beds ⋅ 2 Baths ⋅ Dommerich Hills Second Add SubDv. ⋅ 32751 Zip Code

***Charming Dommerich Hills Home with Scenic Lake Views and Modern Updates*** Nestled in the desirable Dommerich Hills, this beautiful 4-bedroom, 2-bath lakeside home offers a serene lifestyle with views of the lush conservation area and Lake Waumpi. Mature trees and an expansive backyard create a peaceful retreat, with ample space to add a pool. The home’s classic Florida charm is enhanced with modern features, including new double-paned, Low-E windows and doors for energy efficiency and comfort. Inside, the home showcases a blend of hardwood and porcelain tile floors throughout, providing an elegant and low-maintenance living space. The updated kitchen boasts stainless steel appliances, granite countertops, and a reverse osmosis system for the purest drinking water. A large office provides additional versatility, perfect as a guest room or a second living space. Recent upgrades include a new roof in 2022, a new AC unit installed in 2021, and a screened porch addition from 2019 that offers a perfect spot to enjoy the outdoors. Located within the sought-after Winter Park School District and already converted to the city sewer system, this home is move-in ready for its new owners. Don’t miss the opportunity to experience the best of Dommerich Hills – schedule your showing today!

2338 Tuscarora Trail, Maitland

$475,000

2 Beds ⋅ 2 Baths ⋅ Lake Maitland Terrace Apts SubDv. ⋅ 32751 Zip Code

Take advantage of a rare opportunity to own one of only five double units at Lake Maitland Terrace, perfectly situated on the Winter Park chain of lakes. This 1,224-square-foot ground-floor residence offers 2 bedrooms and 2 baths and has been fully reimagined and renovated with designer finishes, luxury appointments, and thoughtful accessibility features, creating a home that effortlessly blends elegance, comfort, and modern convenience. Bright and inviting, this one-of-a-kind unit features custom cabinetry and lighting, shiplap walls, tongue-and-groove ceilings, wood-grain ceramic tile flooring, and bespoke window treatments throughout. The primary suite includes an ensuite bathroom with a roll-in shower and floating vanity. The gourmet eat-in kitchen comfortably seats eight and boasts a walk-in pantry and built-in appliances. Prewired for Smart-Home technology, this home allows for effortless voice activated control of the AC, lighting, TV, music, and front door locks. A dedicated laundry area completes the thoughtful design. Owners will also enjoy a front patio, accessible parking, and the convenience of walking to Lake Lily, the Enzian Theater, nearby shops and restaurants, as well as direct access to the lakes. This is a rare opportunity to own a fully renovated, one-of-a-kind residence that combines style, sophistication, and independence. Call today to schedule your showing.

1140 S Orlando Avenue Unit C2, Maitland

$815,000

4 Beds ⋅ 3 Baths ⋅ Lakewood Shores 1st Add SubDv. ⋅ 32751 Zip Code

Welcome to 185 Birchwood Drive, a rare Maitland SKIABLE LAKEFRONT retreat offering the perfect combination of privacy, elevation, and effortless Florida luxury. Positioned high above the waterline with sweeping lake views, this property delivers true lake living without the typical flood insurance requirement. Inside, the home is bright and inviting with luxury vinyl plank flooring throughout and a functional layout designed for both everyday comfort and entertaining. The open-concept main living space is highlighted by vaulted ceilings and a dramatic wall of glass framing the water, flowing seamlessly into the kitchen with generous cabinetry, stainless appliances, and a large center island ideal for gathering. The home also features beautifully updated bathrooms, and a split floor plan that provides ideal separation for guests, a home office, or multi-generational living. Outdoors, enjoy a private waterfront oasis complete with a resort-style pool, expansive entertaining space, and fully fenced yard perfect for dogs, and a updated 2019 roof. And because the lake is private, you can enjoy boating without the hassle of registering your boat—a rare convenience for waterfront owners. Perfectly located near I-4 with express lane access, 17-92, and just minutes to Park Avenue / Winter Park, this home offers the lifestyle buyers want most: stunning views, privacy, convenience, and true lakefront enjoyment.

185 Birchwood Drive, Maitland

$735,000

3 Beds ⋅ 3 Baths ⋅ Minnehaha Shores SubDv. ⋅ 32751 Zip Code

RARE opportunity to own a Maitland Shores home offering access to Lake Minnehaha AND the Winter Park Chain of Lakes. Residents enjoy exclusive use of the HOA lakefront park with a fishing dock and paved boat ramp that creates quick access to the Nina Canal and Lake Maitland — the largest lake in the Winter Park Chain. The unique location of this home offers an oversized .34-acre homesite that is thoughtfully landscaped with rare tropical plants, rose gardens, and a peaceful front courtyard complete with a bubbling fountain. Ample driveway and garage space accommodate boat or vehicle storage, ideal for enjoying skiable Lake Minnehaha. Inside, this 3 bedroom, 2.5 bath home offers 2,249 square feet of living space in a split floorplan. A unique highlight of the floorplan is the dual primary suites, each with private access to the screened pool, making the home ideal for multi-generational living. Equally beautiful pool views are also visible from the kitchen, breakfast nook, and spacious family room. If you are staying inside, the family room features a large fireplace that creates a cozy focal point. Just off the family room is the remodeled kitchen that is both bright and functional with abundant cabinetry, granite counters, stainless steel appliances, breakfast bar seating, a built-in desk, and a breakfast nook with patio access. Beauty abounds from the patio with a resort-style screened pool, complete with decorative palms surrounding the pool. Steps from the pool begin the meandering gardens with colorful blooms. To aid the avid gardener is a covered and secure garden shed. With such an expansive homesite - more than 15,000 square feet - possibilities for adding a full workshop or even an Accessory Dwelling Unit/ADU could be explored. Adjacent to this estate is Minnehaha Park, a 7.5-acre City of Maitland park offering multiple tennis courts, pickleball courts, walking trails, picnic pavilions, and playgrounds. While the setting of this property is quiet and serene, the home is minutes from Winter Park shopping and dining; downtown Maitland and Maitland City Centre; I-4 access; and zoned Winter Park High School. Additional home updates include a full roof replacement and AC replacement in 2021, making move-in and insurance smooth and easy. Don't miss this chance to get Winter Park Chain of Lakes access for yourself at this exceptional price!

109 Minnehaha Circle, Maitland

$1,199,500

5 Beds ⋅ 4 Baths ⋅ Wellington SubDv. ⋅ 32751 Zip Code

Welcome home to one of the best-kept Maitland secrets, the neighborhood of Wellington. This lakefront home enjoys over 125 feet of linear frontage on Lake of Woods, a spring-fed skiable lake. Home is nearly 3,200 square feet, four bedrooms, three baths with incredible sunset views. Home is spacious with a first-floor primary suite and other bedrooms upstairs with generous flex space. Living space features a wood-burning fireplace with a vaulted ceiling and wood beam architectural accents. Two separate covered porches and screened pool make entertaining a breeze. Other features include solar power energy system (paid in full), newer roof, 2024 air conditioner, updated Hardie board siding, new windows, leaf guard gutter system, replumbed and more. This location is pristine close to many amenities and major roadways. This is a unique opportunity to enjoy lake life at its best.

1232 Wellington Terrace, Maitland

$749,900

2 Beds ⋅ 2 Baths ⋅ West Cove SubDv. ⋅ 32751 Zip Code

LAKEFRONT - Enjoy condo living at its finest from the top-floor Lake Maitland penthouse with million-dollar water and above treetop views, and beautiful panoramic sunrises from multiple rooms. This 9th-floor, 1,685 SF residence features 2 bedrooms, 2 baths, 2 multi-purpose rooms, and an open-concept kitchen, dining, and living area. Centered on the west cove of Lake Maitland, the largest of the Winter Park Chain of Lakes. The primary suite offers a spacious bath with an oversized walk-in shower and walk-in closet. The second bedroom includes guest bath access and a 6-ft soaking tub. Interior features include engineered wood flooring, plantation shutters, grand crown molding, and custom built-ins, display areas and doors. Three sets of French doors open to two balconies overlooking the lake. Balcony features electric hurricane shutters and a private 6’x5’ storage closet. A place of serenity, peace and beauty; with an energy of quiet, expansiveness and closeness to nature. Community amenities include resort-style pool and spa, boat docks, kayak racks, fitness center, clubhouse, and on-site management. Walk to Enzian Theater, Lake Lily Park, community center, library, dining, farmers market; minutes to Park Ave, Whole Foods, Winter Park Village, and major roads.

1100 S Orlando Avenue Unit 956, Maitland

$630,000

4 Beds ⋅ 3 Baths ⋅ Druid Isle SubDv. ⋅ 32751 Zip Code

Nestled in the highly desirable Druid Isle neighborhood, this single-family residence offers the perfect blend of comfort, style, and waterfront living. Boasting 2,162 square feet of thoughtfully designed living space, this 4-bedroom, 3-bathroom home is ideal for both everyday living and entertaining. A welcoming layout and abundant natural light create a warm, inviting atmosphere throughout. Step outside to your own private oasis, where a sparkling pool overlooks serene lakefront views, providing a picturesque backdrop for relaxation and outdoor gatherings. Whether enjoying morning coffee by the water or hosting sunset get-togethers, the outdoor space is designed to make the most of Florida living. The peaceful lake setting adds a sense of privacy and tranquility rarely found so close to it all. Completing the home is a spacious 2-car garage and a prime location in one of the area’s most sought-after neighborhoods. Druid Isle is known for its charm, convenience, and strong sense of community, making this property an exceptional opportunity. This lakefront pool home truly offers the lifestyle you’ve been looking for—comfort, beauty, and an unbeatable location.

1301 Druid Isle Road, Maitland

$897,000

4 Beds ⋅ 2 Baths ⋅ Dommerich Woods SubDv. ⋅ 32751 Zip Code

LOCATION! LOCATION! LOCATION! SERENE HOME in beautiful Dommerich Woods. Located on a quiet cul-de-sac, this unique .28+ acre property offers a single story, 4 bedroom + flex room split plan surrounded by peaceful nature. Brick driveway invites you to a gated courtyard leading to front door & fenced property offering complete privacy including pool, tranquil haven overlooking lush preserve & side yards for garden/play. Step inside to experience spacious foyer & living room with wood burning fireplace & wall of windows to front courtyard. The primary suite boasts a flex room perfect for home gym, office or nursery leading to 21x 14 primary bedroom!! Bright kitchen overlooks sparkling pool & family room leading to additional three bedrooms & guest/pool bath. This delightful home offers so much natural light, great closet space, hardwood floors, 2 car garage, new roof, gutters, AC, ductwork 2018, NO HOA!, Dommerich Elementary, Maitland Middle & Winter Park High & access to boat ramp on Lake Minnehaha leading to the Winter Park Chain of Lakes. WELCOME HOME!

821 Woods Court, Maitland

$3,000,000

Hollieanna Shores 1st Add SubDv. ⋅ 32751 Zip Code

A rare opportunity to secure a Lake Maitland homesite on the desired Maitland–Winter Park Chain of Lakes, an increasingly limited offering as quality lakefront parcels continue to disappear. Along a quiet street with an exceptional sense of privacy, this property lends itself beautifully to a gated approach and captures expansive southern-facing water views, offering breathtaking light throughout the day, from early morning glow to sunset skies. With approximately 27,472 square feet of uplands, the site has been cleared and is poised for new construction. Preliminary estimates suggest the potential for a residence in the approximately 10,000-square-foot range (approximately 40% of the lot size), though all building parameters should be verified through the City of Maitland and your architect/builder during due diligence. Existing improvements include a seawall plus a covered boat lift and dock, delivering immediate enjoyment of the Chain-of-Lakes lifestyle with boating, fishing and watersports right from your backyard. Envision a multi-generational estate designed for life on the water including morning paddle rides, afternoons on the dock and evenings spent poolside watching boats drift by. From here, it’s easy to embrace the local lake culture, whether cruising across the water or heading into Winter Park for boutiques, dining and energy of Park Avenue, while enjoying convenient access to downtown Maitland amenities and major roadways. Additional opportunity of the neighboring lakefront parcel at 125 Whitecaps Circle (approximately 18,500 square feet/.42 acres) is also available, presenting an exceptional option to combine two side-by-side properties for a larger estate footprint or a shared family-and-friends compound. All measurements and development assumptions are provided as estimates and must be confirmed by appropriate governing authorities and your design/construction team.

127 Whitecaps Circle, Maitland

$315,000

3 Beds ⋅ 2 Baths ⋅ Sun Bay Club Condo SubDv. ⋅ 32751 Zip Code

Wake up to water views, an abundance of natural light, and tropical serenity in this beautifully appointed, private ground-floor residence. Embrace a calm, relaxing lifestyle in this light-filled, ground-floor condo surrounded by lush tropical landscaping, located in Maitland’s popular gated community of Sun Bay Club. Designed for effortless living, this spacious 3-bedroom, 2-bath residence offers a rare no-stairs layout and exceptional privacy, set on a desirable lot with no direct rear neighbors and tranquil pond views both behind and to the side. The elegant living area is anchored by a wood-burning fireplace, and flows through French doors into a sunlit, enclosed Florida room, with expansive windows and sliding glass doors—perfect for morning coffee, evening relaxation, or entertaining while enjoying serene, tropical surroundings. Sliding glass doors in the primary bedroom and kitchen open directly to the Florida room, enhancing the indoor-outdoor lifestyle. The kitchen features beautiful quartz countertops, stainless steel appliances, and a charming breakfast nook overlooking the pond, creating an inviting space to start each day. The second bedroom opens to a private patio with peaceful water views, while the third bedroom faces the front and offers flexibility as a home office, playroom, or guest retreat. LVP and ceramic tile flooring, abundant storage, and a thoughtfully designed layout provide both comfort and sophistication. Meticulously maintained with evident pride of ownership throughout. Recent upgrades include a newer A/C (2022) and a brand-new hot water heater (2025), newly painted areas interior. Enjoy the ease of walking to the community pool, lakes, and tennis courts, while coming home to a quiet, private setting. Centrally located just minutes from I-4, Winter Park, the beaches, the parks, hotels, dining, and shopping. Call today for your showing appointment!

1000 Winderley Place Unit 142, Maitland

$952,000

4 Beds ⋅ 3 Baths ⋅ Maitland Shores SubDv. ⋅ 32751 Zip Code

Welcome to 67 Cypress Lane, a stunning single-owner custom residence nestled among majestic Cypress and Oak trees across from Lake Maitland in one of the area's most coveted neighborhoods. This architectural gem, expertly crafted from Western Red Cedar, offers two stories of thoughtfully designed living space with 4 bedrooms and 3 full baths. Step inside to discover hardwood floors flowing throughout the first level, leading to a dramatic sunken living room and formal dining room perfect for entertaining. The heart of the home is the spectacular family room featuring soaring 17-foot ceilings, a wood-burning fireplace, and expansive windows that bathe the space in natural light. The well-appointed kitchen boasts granite countertops, a charming breakfast nook, and glass sliders opening to a covered side porch—ideal for morning coffee or evening relaxation. The main level also includes a convenient guest bedroom and full bath, separate living and dining rooms, plus an attached 2-car garage. Upstairs, retreat to the loft-style primary suite with private en suite bath, two additional guest bedrooms, a hall bath, and laundry facilities for ultimate convenience. Outdoor living shines here with a front deck off the family room and multiple porch spaces. The quiet, dead-end street ensures peace and privacy. For just $100/year, the optional HOA provides deeded park access to beautiful Lake Maitland directly across the street—feel the refreshing lake breeze from your front door! Just minutes from the Winter Park Racquet Club and all that downtown Winter Park and Maitland have to offer. Zoned for award-winning Dommerich Elementary, Maitland Middle, and Winter Park High School. Complete with Terminix termite bond for peace of mind. This tranquil neighborhood retreat offers a rare combination of custom quality, natural beauty, and an unbeatable location. Don't miss this exceptional opportunity!

67 Cypress Lane, Maitland

$1,025,000

4 Beds ⋅ 4 Baths ⋅ Dommerich Woods SubDv. ⋅ 32751 Zip Code

On a quiet street in one of Maitland's desirable neighborhoods, this home blends timeless elegance with modern comfort. This stunning residence offers a combination of sophistication and functionality, making it the ideal place to call home. Boasting four bedrooms, 3.5 baths and plenty of flex space, this residence spans over 2,600 square feet and sits on a generous .33-acre lot. Natural light draws you into the entry with views of the backyard oasis. The abundance of outdoor living that includes a covered porch with vaulted ceilings, private pool, two separate sitting areas with composite decking and garden areas, provide the backdrop for hosting family and friends. The kitchen is outfitted with stainless appliances (2025), ample cabinetry, a large walk-in pantry and granite/butcher block countertops. This split plan offers three bedrooms and two baths on the second level, one bedroom is complete with an en-suite bath. The peaceful owner's retreat is on the lower ground floor and is completely private from the rest of the living areas. It features a flex space/office as you enter the primary bedroom with a set of solid double doors. Once inside, you will notice two walk-in closets, an en-suite bath with a jacuzzi tub and separate shower, along with a walkout to a private courtyard area. Updates include roof in 2025, exterior paint in 2025, new wood fence in 2024, one HVAC in 2024 and solid wood doors with Baldwin hardware. Other features of the home include optional access to the Lake Minnehaha boat ramp, which leads to the exclusive Chain of Lakes. With easy access to downtown Maitland, Interstate 4, Maitland Community Park, Dommerich Elementary and Maitland Middle Schools, this home is a must-see!

798 Sequoia Trail, Maitland

$1,165,000

5 Beds ⋅ 3 Baths ⋅ Dommerich Estates 1st Add SubDv. ⋅ 32751 Zip Code

Built in 2014 and set within the highly sought-after Dommerich Estates neighborhood of Maitland, this thoughtfully maintained two-story home offers a rare blend of space, function, and location. With five bedrooms, three full bathrooms, and a flexible bonus room, the layout is designed to adapt easily to modern living. The entry opens to a formal dining space, while an additional room just off the foyer provides an ideal spot for a home office, den, or reading lounge. Dark hardwood floors anchor the main living areas and create a warm, cohesive feel throughout. At the heart of the home, the open kitchen and family room flow seamlessly together and look out over the backyard—perfect for both relaxed evenings and hosting gatherings. The kitchen features Bosch stainless steel appliances, granite countertops, a generous island with seating, and custom maple cabinetry, offering both style and practicality. The primary suite is privately positioned on the main level and includes two walk-in closets. Its en-suite bath is finished with double vanities, a soaking tub, a separate shower, and ceramic tile throughout. Two additional bedrooms on the first floor share a full bathroom with ceramic tile and a granite-topped vanity. Upstairs, a spacious bonus room creates endless possibilities, accompanied by two more bedrooms connected by a Jack-and-Jill bathroom with matching granite and tile finishes. Notable extras include an interior laundry room with washer and dryer, dual HVAC systems, and a fully fenced backyard with a lovely patio and plenty of room to add a pool or play area. Ideally located just moments from the new boardwalk leading to Maitland Community Park, residents enjoy easy access to walking paths, green space, playgrounds, and nearby tennis courts, enhancing the neighborhood’s active and outdoor lifestyle. Zoned for Dommerich Elementary, Maitland Middle, and Winter Park High School, the home also grants access to Lake Minnehaha, where residents enjoy a private boat ramp and fishing dock. A standout opportunity in one of Maitland’s most established and beloved lakefront communities. This home is back on the market after the previous buyer experienced a personal change in plans. No issues with the property.

1750 Cheyenne Trail, Maitland

$4,999,000

5 Beds ⋅ 8 Baths ⋅ Floridahaven SubDv. ⋅ 32751 Zip Code

Pre-Construction. To be built. An extraordinary opportunity to claim one of Lake Seminary’s desired shorelines awaits. Masterfully envisioned by Heathrow Custom Homes, this newly built lakefront estate introduces a fresh standard of modern luxury for Maitland and Winter Park. Poised on an expansive 0.69-acre parcel, the residence spans nearly 6,500 square feet of impeccably curated living space, where sophisticated architecture and bespoke finishes harmonize with the tranquil beauty of the lake. A striking floating staircase framed by floor-to-ceiling glass offers a captivating first impression, while the grand entry reveals uninterrupted vistas of the pool terrace and shimmering water beyond. The chef’s kitchen, anchored by a remarkable 20-foot island, features premier appliances, exceptional storage and a concealed full-service scullery, creating an environment for hosting with grace and ease. The great room continues the home’s celebration of light and space with walls of glass that welcome breathtaking lake views at every turn. The primary suite is a serene retreat, showcasing a spa-inspired bath with floating vanities, a freestanding soaking tub, an expansive glass-enclosed shower and extravagant walk-in closets designed for the discerning owner. A secondary bedroom suite and oversized laundry enrich the main level, while an expansive lanai with an extraordinary summer kitchen invites effortless alfresco living, an experience only genuine lakefront living can provide. The second floor unfolds into a generous game room, complete with a wet bar and kitchenette. Three beautifully appointed bedroom suites, two scenic balconies, and a purpose-built home theater create an environment tailor-made for indulgence and entertainment. A new boathouse, soon to be constructed, further elevates the lakefront lifestyle. With three garages, a contemporary parking court, and meticulously executed architectural detail, this residence embodies modern luxury at its most refined. Lake Seminary, home to just 35 exclusive residences, offers coveted privacy while remaining moments from boutique shopping, celebrated dining and best of Winter Park. Immediate access to Interstate 4 and surrounding beltways ensures effortless connectivity throughout Central Florida.

360 Lake Seminary Circle, Maitland

$625,000

4 Beds ⋅ 3 Baths ⋅ Minnehaha Shores SubDv. ⋅ 32751 Zip Code

Welcome to this beautifully refined 4-bedroom, 3-bath POOL HOME in the highly sought-after Minnehaha Shores community of Maitland. Situated on a prominent corner lot with picturesque views of Minnehaha Park, this residence offers thoughtful enhancements, generous indoor–outdoor living, and exclusive neighborhood lake access to the Winter Park Chain of Lakes. Step inside to an airy, open layout filled with natural light, complemented by luxury vinyl plank flooring and plantation shutters throughout. The chef’s kitchen is the heart of the home, featuring granite countertops, subway tile backsplash, butcher-block accents, premium stainless steel appliances, and abundant cabinetry. The kitchen flows seamlessly into the dining and family rooms, ideal for daily living or effortless entertaining. A separate formal living room with pocket doors provides flexible space for work, relaxation, or hosting guests. Four well-appointed bedrooms provide comfort and versatility, including a spacious primary suite with a thoughtfully designed ensuite bath. The fourth bedroom can serve as a home office, guest room, or creative space. A rare dedicated pool bath adds convenience, and all bathrooms showcase modern tile work and stylish finishes. An indoor laundry/utility room enhances day-to-day functionality. Step outdoors to a quintessential Florida oasis with a sparkling private pool, expansive patio, and fully fenced green space, perfect for entertaining, quiet mornings, or recreation. Major improvements completed in 2013 include enhanced electrical and HVAC systems, providing peace of mind and long-term ease. Located at 10 Minnehaha Cir, Maitland, FL 32751, this home rests on a tranquil cul-de-sac surrounded by beautifully maintained homes and a friendly neighborhood atmosphere. Residents enjoy private lake access, a community boat ramp, and a dock—amenities rarely found at this price point. Zoned for top-rated Dommerich Elementary, Maitland Middle, and Winter Park High, this location is among Central Florida’s most desirable. More than move-in ready, this home blends timeless character with modern comfort in one of Maitland’s premier neighborhoods. Every room has a story, every space invites possibility, and each day feels like the start of something special. The best journeys always lead home—and this one begins here.

10 Minnehaha Circle, Maitland

$243,000

3 Beds ⋅ 3 Baths ⋅ Park Lake Twnhs Ph 02 SubDv. ⋅ 32751 Zip Code

Experience lakeside living in this elegant 3-bed, 3-bath townhome in the heart of Maitland! This 1,575 sq ft residence offers refined, comfortable living with tranquil lake views. The townhome features two upstairs ensuite bedrooms—one with a private balcony overlooking the lake, a perfect spot to enjoy your morning coffee—and a convenient first-floor bedroom that provides space and ease. Enjoy a large patio ideal for entertaining, plus community amenities including a pool and park. Prime Maitland location near Maitland City Centre, SunRail, I-4, and upscale dining and shops. Currently leased through 2/2026, this serene lakeside townhome offers the rare flexibility of a strong investment today and a sophisticated primary home tomorrow. Experience the beauty and convenience of Maitland living—book your private tour today!

806 Town Circle Unit 156, Maitland

$415,000

3 Beds ⋅ 2 Baths ⋅ Lake Eulalia Heights SubDv. ⋅ 32751 Zip Code

Step into timeless style with this completely updated mid-century modern home tucked away on a quiet Maitland cul-de-sac. This 3-bedroom, 2-bath residence offers 1,521 sq ft of thoughtfully designed living space featuring refinished terrazzo floors, brand-new windows, and abundant natural light. The modern kitchen shines with new cabinets, stone countertops, and stainless-steel appliances, while both bathrooms have been beautifully remodeled with contemporary finishes. Fresh interior and exterior paint, new lighting and ceiling fans throughout, and lush new landscaping make this home truly move-in ready. Enjoy the best of Central Florida living—just steps from Maitland’s shops and restaurants and minutes from charming downtown Winter Park

6 Barnard Court, Maitland

$571,000

3 Beds ⋅ 4 Baths ⋅ Enclave/Maitland A-F SubDv. ⋅ 32751 Zip Code

Data Entry

1240 Trust Lane, Maitland

$159,000

2 Beds ⋅ 1 Baths ⋅ Lake Maitland Terrace Apts SubDv. ⋅ 32751 Zip Code

Welcome to Lake Maitland Terrace, a charming lakeside community of Mid-Century Miami Modern condos set within eleven cottage-style buildings along the shores of Lake Maitland. Residents enjoy resort-style amenities, including a recently renovated lakeside pool, fishing dock, putting green, shuffleboard courts, and a clubhouse with kitchen. This first-floor, two-bedroom, one-bath condo in the Arlington Building has been maintained by the same owner for nearly 30 years. Updates include a 2021 AC, 4-year-old water heater, newer windows and front door, and a new roof (2023–2024). The open great room flows into the dining area, and the adjacent kitchen features a 2nd entrance. Much of the interior remains in original condition, and the old carpet has been removed, providing an ideal opportunity for a new owner to update and make it their own. Additional features include one designated parking space, ample guest parking, enclosed bicycle storage, convenient laundry facilities, and racks for kayaks and paddleboards. The location is unbeatable—walk to the Enzian Theater and Lake Lily, or drive just five minutes to downtown Winter Park with easy access to I-4. Condo is being sold AS IS.

1140 S Orlando Avenue Unit A5, Maitland

$540,000

2 Beds ⋅ 2 Baths ⋅ Moorings On Lake Maitland Condo Bldg 03 SubDv. ⋅ 32751 Zip Code

Welcome to The Moorings, a rarely available lakeside community perfectly positioned across from beautiful Lake Lily. This fully renovated 4th-floor condo combines modern elegance with stunning water views of Lake Maitland, visible right from your living room and screened-in balcony. Inside, you’ll find an open, light-filled layout with white-oak luxury vinyl flooring that sets a clean, contemporary tone. The kitchen has been completely updated with premium appliances, quartz countertops, and brass fixtures, creating a space that’s both stylish and functional. The primary bedroom suite features a spacious walk-in closet and a beautifully finished en-suite bathroom with a large walk-in shower. A second bedroom and full bath offer plenty of room for guests or a home office. Additional conveniences include an in-unit laundry room with washer and dryer, plus elevator access for easy entry. Residents of The Moorings enjoy a host of amenities, including a sparkling community pool, private boat docks, a scenic pier with seating area, a fitness center, and a clubhouse for gatherings. Located just minutes from top-rated restaurants, shopping, and entertainment in Maitland and Winter Park, this condo offers the ideal blend of tranquility and city convenience. Come experience lakefront living at its finest.

206 Quayside Circle Unit 404, Maitland

$1,425,000

3 Beds ⋅ 3 Baths ⋅ Hollieanna Shores SubDv. ⋅ 32751 Zip Code

Sophisticated and timeless, this stunning one-story home was completely reimagined in 2019 by multi-award-winning builder and design through Z-Properties. Taken down to the studs and rebuilt with the finest materials, this split-plan three-bedroom, three-bath residence blends modern design with an inviting, incredible design feel. Gorgeous high grade wood flooring throughout along with expansive windows and walls of glass flood the interiors with natural light, taking advantage of picturesque views! The backyard is a sanctuary setting with Signature Landscape mature landscaping and sparkling pool and separate spa. The open concept design is ideal for daily living and entertaining, with a seamless flow extremely well thought-out living areas. A designer-inspired gas fireplace in the dining area creates a sophisticated and welcoming ambiance, while two sets of glass doors in the living room open to the inviting outdoor living spaces. The stately kitchen is a showpiece, featuring Thermador Pro Series appliances, a Sub-Zero wine tower, and elegant counters that elevate form and function. The primary suite offers a private retreat with a generous walk-in closet and a spa like well-appointed bath. Two additional bedroom suites are equally refined, each with custom closets for optimal storage and organization. Outside, every detail has been thoughtfully curated. The private front courtyard, centered around a tranquil Zen fountain private courtyard, sets the tone for the home's refined elegance. The rear outdoor living area features Brazilian IPE wood decking surrounding the heated saltwater pool, alongside lush landscaping, complete with sculpted hedges and tropical palms, creates a resort-like ambiance. A built-in summer kitchen includes a gas grill and green egg off the kitchen, and flex space is framed by a beautiful bougainvillea hedge for added serenity, ideal for effortless outdoor entertaining. Lastly there is a fully finished garage with indoor/outdoor carpeting and is temperature controlled with its mini-split AC unit. Residents of Hollieanna Shores enjoy deeded lake access to Lake Maitland, part of the prestigious Winter Park Chain-of-Lakes, via a private community boat ramp. Ideally with convenient access to major roadways, this exceptional home offers easy commutes to downtown Winter Park, Orlando and area airports, a sophisticated retreat in one of Central Florida's desirable Maitland/Winter Park hidden gem neighborhoods!

123 Hollie Court, Maitland

$850,000

2 Beds ⋅ 3 Baths ⋅ Moorings On Lake Maitland Condo Bldg 05 SubDv. ⋅ 32751 Zip Code

Every so often, a property comes along that redefines what lake living can be, and this is that home. Thoughtfully reimagined from top to bottom, this two-bedroom, two-and-a-half-bath residence blends refined design with the effortless lifestyle of the Winter Park Chain of Lakes. Go inside to discover a fully renovated interior anchored by a showstopping 14-foot Cambria quartz waterfall island, the heart of a kitchen designed for entertaining and everyday luxury. The GE Monogram and Café appliance suite, paired with custom solid wood, soft-close cabinetry, makes every detail feel bespoke. Natural light fills the living spaces through PGT double-pane insulated windows and Andersen French doors, framing tranquil garden views that create a sense of calm and privacy. Upstairs, two spacious bedroom suites offer comfort and style, each crafted with high-end finishes and thoughtful touches throughout. Beyond the walls, enjoy the rare privilege of a dedicated boat slip on Lake Maitland, Winter Park’s largest and sought-after body of water. Cruise the connected lakes, explore the historic canals or simply unwind at sunset, all just near home. Built in 1985 and completely transformed with modern systems, including a 2023 HVAC and water heater, this residence offers peace of mind to match its beauty. A one-car garage adds convenience, while every finish reflects care, quality and craftsmanship. Here, luxury isn’t just found inside, it’s a way of life, lived by the water.

219 Quayside Circle, Maitland

$613,000

2 Beds ⋅ 2 Baths ⋅ Moorings On Lake Maitland Condo SubDv. ⋅ 32751 Zip Code

Elegant lakefront on the shores of Lake Maitland! Experience timeless refinement in this exquisitely renovated lakefront condominium, where bespoke craftmanship meets modern luxury. Every detail has been thoughtfully curated - from the custom millworker and intricate moldings to the tailored built-ins that evoke charm of a grand London flat. Light filled living spaces open to serene lake views, creating an atmosphere of both grace and tranquility. The gourmet kitchen is a study in elegance and function, featuring hand finished cabinetry, premium appliances, and stone surfaces. Gracious living room flows seamlessly into a charming sunroom, featuring French doors and classic brick flooring. The primary suite offers a peaceful, retreat with lake views, spa-inspired finishes and impeccable attention to detail. With rich textures, layered lighting, and designer finishes throughout, this home balances sophistication and warmth in perfect measure. Located in an exclusive building with exceptional amenities including pool, spa, clubhouse, a BOAT SLIP and 1 covered carport space. This residence embodies elevated lakefront living, with distinctive character. Call today for your private viewing of this exquisite condo. Please note there is a $640 transfer fee for boat slip paid at closing by Buyer.

204 Quayside Circle Unit 202, Maitland

$792,150

3 Beds ⋅ 2 Baths ⋅ Northwood Heights SubDv. ⋅ 32751 Zip Code

Perfectly positioned on the tranquil shores of Lake Seminary, this beautiful home offers the ultimate lakefront lifestyle in the heart of Maitland. From the moment you arrive, the home’s refreshed landscaping and elegant façade set the tone for what awaits inside. Step through the doors and you’re greeted by open living spaces accented by engineered hardwood floors, stylish finishes, and large windows that frame breathtaking views of the lake. The kitchen is a showcase of both function and design, featuring stainless steel appliances, generous counter space, and an open layout perfect for both entertaining and everyday living. The living room takes full advantage of the home’s lakefront setting, offering panoramic water views. The primary suite serves as a private retreat, featuring a large bathroom with dual vanities, a walk-in shower, and a spacious closet. Outdoors, the expansive backyard offers endless possibilities, whether you envision a custom pool, extended patio, or simply space to unwind and entertain with stunning lake views. An above-ground hot tub and patio overlook the glistening lake, creating the perfect setting to unwind while enjoying kayaking, boating, and fishing right from your own backyard. Set on nearly an acre of pristine land, the property features a rare combination of privacy, space, and stunning water views all just minutes from Maitland’s vibrant dining scene and major roadways, this home offers the perfect blend of lakeside tranquility and everyday convenience.

195 E Faith Terrace, Maitland

$779,500

3 Beds ⋅ 2 Baths ⋅ Dommerich Estates 1st Add SubDv. ⋅ 32751 Zip Code

Welcome to this charming, move-in ready home nestled in the desirable, family-friendly Dommerich neighborhood. Featuring 3 bedrooms, 2 full bathrooms, and an open-concept living area filled with natural light, this home has the perfect blend of comfort and style. Featuring 2 additional dedicated office rooms, ideal for remote work or creative space, this home is ideal for modern living. The updated kitchen boasts stainless steel appliances, marble countertops, and ample cabinet space. Step into an open, light-filled interior with brand new flooring throughout and breathtaking floor-to-ceiling windows that has panoramic views of the sparkling saltwater pool. In the cooler months enjoy your own wood burning fireplace. Outside, enjoy a spacious paver driveway, a large 2-car garage, and a private backyard oasis. Major upgrades include a brand new roof (2025), ensuring peace of mind for years to come. Additional upgrades include recessed lighting, new flooring throughout, marble bathroom tiling, energy-efficient windows, new paver driveway and fresh interior/exterior paint. Enjoy private boat ramp access to the Winter Park Chain of Lakes. Zoned for A-rated Dommerich Elementary, Maitland Middle School and Winter Park High School. Walking distance to the Maitland Community Park, Maitland Social and the Maitland City Center. Minutes from Winter Park’s Park Avenue, known for its exquisite shopping and dining. Don’t miss out on this opportunity!

421 Arapaho Trail, Maitland

$400,000

2 Beds ⋅ 2 Baths ⋅ West Cove SubDv. ⋅ 32751 Zip Code

Breathtaking views of Lake Maitland, the largest lake of the desirable Winter Park Chain of Lakes. Enjoy sunrises across the lake from the privacy of your balcony overlooking the pool. This 2-bedroom, 2-bath condo within West Cove Condos is centrally located in close proximity to a variety of restaurants, Lake Lily Park, Enzian Theater and easy access to I-4 and Maitland Blvd. Your association fees include access to the lakefront docks (boat slips assigned on availability basis and free of charge), work out room, lobby area for entertaining, heated swimming pool and spa, grilling area with sitting space, storage racks for canoes, kayaks and paddleboards, assigned and guest parking, laundry room on each floor, cable and internet through Spectrum, plus water, sewer and trash. Elevator has secured access to your floor.

1100 S Orlando Avenue Unit 208, Maitland

$251,500

2 Beds ⋅ 2 Baths ⋅ Lake Maitland Terrace Apts SubDv. ⋅ 32751 Zip Code

Live on Lake Maitland, part of the Winter Park Chain of Lakes, for just $250,000! This 2-bedroom, 1.5-bath condo in Lake Maitland Terrace is one of the most desirable units in the community, offering 816 square feet and a prime second-floor corner location with a screened-in front porch. Inside, you’ll find spacious living areas with bamboo flooring, plantation shutters, and abundant natural light. The porch extends your living space and is the perfect spot to quietly sip your morning coffee. Thoughtful upgrades set this home apart. The washer and dryer are conveniently located in the hallway, preserving closet space in both bedrooms. The primary bedroom features a true walk-in closet, and both bedrooms include custom closet systems that maximize storage and style. Opportunities to live on the Winter Park Chain of Lakes at this price point are incredibly rare. With its generous layout, upgraded features, and unbeatable location, this condo is a standout that won’t last long.

1140 S Orlando Avenue Unit F9, Maitland

$255,000

1 Beds ⋅ 1 Baths ⋅ Lake Maitland Terrace Apts SubDv. ⋅ 32751 Zip Code

Step inside this beautifully reimagined Lake Maitland Terrace condo, where every detail has been thoughtfully updated for style and function. Renovated in 2021, this spacious one-bedroom residence embraces a modern design with clean lines, custom finishes, and a touch of industrial character from the exposed ceiling piping. The open layout features a bright great room that flows seamlessly into the kitchen, designed with both cooking and entertaining in mind. Highlights include Caesarstone quartz countertops, a mirrored backsplash, a farmhouse sink, KraftMaid soft-close cabinetry, and an oversized island with seating. Premium appliances such as a KitchenAid convection oven with induction cooktop, Bosch dishwasher, French-door refrigerator, and in-unit washer and dryer add convenience and sophistication. Originally configured as a two-bedroom, the condo has been transformed into a larger one-bedroom retreat but can easily be converted back if desired. The bathroom offers a tub/shower combination and an extra-wide pedestal sink. Enjoy a low-maintenance lifestyle with resort-style amenities, including a community pool, shuffleboard courts, fishing pier, and access to Lake Maitland and the Chain of Lakes. The unbeatable location puts you within walking distance of the Enzian Theater and Lake Lily, while Winter Park Village, Park Avenue, and A-rated schools are just minutes away.

1140 S Orlando Avenue Unit J2, Maitland

$535,000

2 Beds ⋅ 2 Baths ⋅ Moorings On Lake Maitland Condo SubDv. ⋅ 32751 Zip Code

RARE OPPORTUNITY – Enjoy lakefront living with a PRIVATE BOAT SLIP on the Winter Park chain of lakes in this top-floor penthouse condo. The Moorings on Lake Maitland, one of Central Florida’s most coveted waterfront communities. This spacious 2-bedroom, 2-bath residence offers soaring vaulted ceilings, breathtaking lake views, and your own assigned private boat slip—a rare find on the Winter Park Chain of Lakes. Step inside to an abundance of natural light and a thoughtfully designed floor plan with no upstairs neighbors, ensuring maximum privacy and quiet. The large living area opens to a glass-enclosed sunroom with panoramic views of Lake Maitland—perfect for morning coffee or relaxing at sunset. The kitchen is bright and functional, featuring a breakfast nook and walk-in pantry. The split-bedroom layout offers privacy and flexibility. The primary suite includes a handicap-accessible bath, generous closet space, and tranquil lake views. The guest bedroom and full second bath are perfect for visitors or a home office. The laundry is conveniently located tucked off the main hall, and with custom closets in both bedrooms the amount of storage is great. For larger items the unit includes a locking storage closet on the landing, and is perfect for bikes, golf clubs, holiday decorations etc. The unit comes with one reserved covered parking space and plenty of guest parking. The complex has a newly renovated pool, hot tub & clubhouse. Whether you're looking for a primary residence or a low-maintenance lakefront retreat, this rare top-floor condo offers an unbeatable combination of comfort, convenience, and waterfront access. Live the Florida lake lifestyle—schedule your private showing today!

202 Quayside Circle Unit 404, Maitland

$475,000

4 Beds ⋅ 3 Baths ⋅ Maitland Village SubDv. ⋅ 32751 Zip Code

Charming and Spacious Townhome in Maitland! Welcome to 1938 Michael Tiago a beautifully maintained 4-bedroom, 2.5 bathroom home located in the desirable Maitland Village Community with a POND VIEW and END UNIT. This stunning property offers a perfect blend of classic charm and modern convenience, making it an ideal place to call home. As you approach this inviting residence, you’ll notice the lush landscaping and curb appeal that instantly sets the tone for what’s inside. Step into the spacious living area, where natural light pours in through large windows, creating a warm and inviting atmosphere. The open-concept floor plan seamlessly flows into the dining area and kitchen, making this space perfect for both everyday living and entertaining guests. Crown molding enhances the rooms adding just that right touch! Custom Plantation Shutters adorn all the windows downstairs & upstairs. The kitchen is a chef's dream, featuring stainless steel appliances, granite countertops, and ample cabinet space for all your culinary needs. A walk in panty is another feature of the kitchen. Whether you're preparing a weeknight meal or hosting a dinner party, this kitchen will exceed your expectations. The primary suite is generously sized and offers a peaceful retreat, complete with a private en-suite bathroom featuring a dual vanity, soaking tub, and a separate walk-in shower. Two additional well-appointed bedrooms provide plenty of space for family. The fourth bedroom featuring French Doors is located downsttairs...it can also be used as an office if needed. The Loft upstairs is light & bright and would make a great office or home school area. The Tile Roof brings long lasting peace of mind. This is an End Unit which allows for more light to filter thru from outside. Hot Water Heater is new. New Stainless Steel Dishwasher & Disposal are being installed. HOA fees cover exterior maintenance, 500 Mbps internet, 250 channel cable, water, sewer, trash, lawn care, sprinklers, streetlights, community pool, clubhouse, gate access and management services. Your low HOA fee takes care of all the yard work so you can enjoy the Community Pool. This makes living here "totally carefree living at its best". Other highlights include tile & engineered wood flooring throughout downstairs, a covered porch with a pond view, no neighbor on one side and a 2-car garage that has 2-car EV-ready. Located just minutes from shopping, dining, and major roadways, this home offers the convenience of being close to everything while providing a quiet, serene neighborhood feel. Don't miss your chance to own this charming Maitland home. Schedule a showing today and make 1938 Michael Tioga your new address!

1938 Michael Tiago Court, Maitland

$395,000

2 Beds ⋅ 2 Baths ⋅ Moorings On Lake Maitland Condo SubDv. ⋅ 32751 Zip Code

SELLER PAYING CONCESSIONS OF 6 MONTH HOA FEES. Something is very special about Lakefront Living! Come visit this beautiful Lakefront Condo located at The Moorings On Lake Maitland, part of the Winter Park chain of lakes. Enjoy the Florida lifestyle in a carefree home with lake front amenities. Imagine Entertaining Family & Friends at the Pool or Heated Spa and the Clubhouse of the Moorings on Lake Maitland. Enjoy relaxing on the Lake Front Dock or on your own Private Enclosed Patio! Step inside this spacious 2 bedroom 2 bath great room plan, perfect for relaxing or entertaining. The beautifully upgraded kitchen has stainless steel appliances and granite counters and a charming dining nook. The master suite features an updated ensuite bath with dual sinks and a walk in shower with a custom glass enclosure. There is a generous walk in closet with custom built ins. Imagine coffee in the morning with lake views from your living room or your spacious patio. Only 5 minute drive to Winter Park's shops & Sidewalk Dining along the famed Park Avenue. Stroll over to Maitland's lovely Lake Lilly Park for Seasonal Events, Art Festivals, Concerts and local Farmer's Market! Incredible Location & Lifestyle!!!!

204 Quayside Circle Unit 304, Maitland

$2,550,000

Hollieanna Shores 1st Add SubDv. ⋅ 32751 Zip Code

Wonderful lakefront lot opportunity to create a custom legacy estate on Lake Maitland, part of the Maitland-Winter Park Chain of Lakes. Lakefront homesites are becoming increasingly rare, and this offering is truly special. Tucked away on a quiet street, the property enjoys a very private setting with the ability to be gated, along with sweeping southern lake views that capture both sunrise and sunset in equal measure. Photos #9–#14 illustrate a thoughtfully conceived design concept created specifically to complement the lot’s dimensions and orientation, while maximizing panoramic lake views and indoor-outdoor living. With approximately 18,500 square feet of upland to be developed, there is potential to build a residence of approximately 7,500 square feet (roughly 40% of the lot size). The site has already been cleared and is ready for construction, allowing a future owner to move seamlessly from vision to reality. Property enhancements include a seawall, gated front entry drive, and a covered boat lift with dock—offering immediate access to boating, fishing, and water sports. This is a rare canvas for a multi-generational lakefront estate, where architectural distinction meets a lifestyle centered on the water. Days may be spent wakeboarding, casting a fishing line, or relaxing poolside as boats glide across the lake, while evenings invite effortless cruises across the water to the Winter Park Racquet Club for dinner, cocktails, and social gatherings. Nestled in a secluded enclave of Maitland, the property is just minutes from the boutiques and dining of Park Avenue, with convenient access to downtown Maitland, major roadways, and the greater Orlando area. Note: The adjacent lakefront property, 127 Whitecaps Circle (24,472 square feet, approximately 0.56 acres) is also listed for sale, presenting a rare opportunity to combine two neighboring lakefront parcels and create a private compound for family or friends. All building calculations and development potential to be confirmed with the City of Maitland and the buyer’s builder and architect during due diligence, as any referenced figures are preliminary and not officially verified.

125 Whitecaps Circle, Maitland

$899,000

4 Beds ⋅ 3 Baths ⋅ Maitland Isle SubDv. ⋅ 32751 Zip Code

This beautifully updated residence, nestled on a desirable corner lot in the tranquil Maitland Isle Subdivision, offers nearly 2,900 square feet of refined living with four bedrooms and two and a half baths. The home enjoys private lake access to Lake Maitland on the Winter Park Chain of Lakes, combining natural beauty with everyday convenience. Designed with a split, open floor plan filled with abundant natural light, it showcases a completely renovated kitchen (2020) featuring a large island with granite countertops, wood cabinetry and stainless steel appliances. Upstairs, the spacious primary suite is a private retreat with its own balcony overlooking the pool and backyard, while the lushly landscaped grounds include mango, avocado and tangerine trees, creating a serene tropical escape. Recent updates elevate this home’s appeal, including new carpet (2025), a pool cleaner (2025), one A/C unit (2025), plantation shutters (2025), dishwasher (2025), new windows (2024), a car charger installation (2024), washing machine (2024) and attic insulation (2022). Additional enhancements include renovated baths, luxury vinyl plank flooring, updated exterior doors, outdoor fencing and energy-efficient solar panels (2018) that provide approximately $250 per month in electricity savings. The roof, pool equipment, and more have also been thoughtfully upgraded for peace of mind. Perfectly positioned within an excellent school district—Lake Sybelia Elementary, Maitland Middle and Winter Park High—this home is close to Maitland City Center, Park Avenue, and local dining, parks and recreation. Combining comfort, modern updates and an exceptional location, this Maitland Isle property is an outstanding opportunity in one of the area’s most sought-after neighborhoods.

121 Mariner Way, Maitland

$825,000

4 Beds ⋅ 3 Baths ⋅ Wellington SubDv. ⋅ 32751 Zip Code

Welcome to your dream home in the friendly community of Wellington in Maitland. This impressive 4-bedroom, 3-bathroom residence spans 3,853 square feet and sits on a spacious 0.34-acre lot, perfect for family gatherings and entertaining. Step inside to discover an open layout filled with natural light. High ceilings and porcelain tile floors create an inviting atmosphere. The heart of the home, a gourmet kitchen, is equipped with stainless steel KitchenAid appliances, granite countertops, and a breakfast bar for casual dining. You'll love the convenience of two large pantries for all your cooking needs. The cozy family room has a beautiful fireplace and is open to the kitchen. The downstairs also includes a bedroom and bathroom perfect for in laws to stay the weekend! The upstairs includes the master suite, 2 additional bedrooms, another bathroom, a multi-function room perfect for movie night or workouts, and a well appointed laundry room. The master suite is a true retreat, showcasing a walk-in closet and a spa-like ensuite with a deep soaking tub and a spacious walk-in shower. It also features a large walk in closet, and an extra nook area for an office or nursery. Enjoy evenings on the sprawling patio, or cozy up by the fireplace indoors. Your outdoor oasis features a saltwater heated pool, a covered entertainment area, and a fire pit for memorable nights under the stars. The lush yard provides plenty of space for gardening and outdoor activities. Located near Kewannee Park, enjoy nature trails, playgrounds, and more, all within a quick bike ride. The nearby downtown Winter Park offers delightful dining and shopping. With easy access to I-4 and local attractions, this home is perfectly positioned for convenience. This family-friendly property includes SMART home features, energy-efficient windows, solar panels, and ample parking for your boat or RV. Come see how this spacious home can elevate your lifestyle.

1888 Derbyshire Road, Maitland

$995,000

3 Beds ⋅ 3 Baths ⋅ Dommerich Woods SubDv. ⋅ 32751 Zip Code

BACK ON THE MARKET!! Welcome to 1630 Chinook Trail, a fully renovated custom patio-style home making its market debut. Designed by builder Phil Kerr and architect Alan Berman, this home features French doors from nearly every room opening to a sparkling pool. Inside you’ll find 3 bedrooms plus a den, guest suite with walk-in closet and ensuite bath, and a 4th bedroom converted into a spacious master closet that can easily be re-converted. The open floor plan boasts a chef’s kitchen with a 10-ft island, 2 dishwashers, double-wide fridge, double ovens with convection, pot filler, and gas range. Additional highlights include a gas fireplace, Nuvo sound system, tankless water heater, energy-efficient windows, and a 2-car garage with workshop space. Outdoors enjoy a travertine front patio, fenced backyard with deck and tree fort, and a resort-style pool with travertine decking and water feature. This home has deeded lake access and a private boat ramp into Lake Minnehaha and walking distance to top-rated schools and Maitland Community Park.

1630 Chinook Trail, Maitland

$352,500

3 Beds ⋅ 2 Baths ⋅ N/A SubDv. ⋅ 32751 Zip Code

+++ AMAZING REHAB OPPORTUNITY IN MAITLAND WITH DEEDED LAKE ACCESS +++ HERE IS A GREAT CHANCE TO OWN IN BEAUTIFUL MAITLAND ON A STREET WITH ONLY 9 HOUSES, NO HOA, AND A BOAT RAMP (FOR RESIDENTS ONLY) ONTO 58 ACRE LAKE SEMINARY! PRICED WITH NEEDED RENOVATIONS IN MIND, THIS SOLID BLOCK HOME IS WAITING TO BE RETURNED TO PRISTINE CONDITION. MANY OF THE HOMES ON THIS STREET HAVE BEEN COMPLETELY RENOVATED. THIS HOME HAS 3 BEDROOM AND 2 FULL BATHS. THE KITCHEN AND UTILITY ROOM ARE LARGE AND ALL BEDROOMS ARE GOOD SIZE. THE LARGE FAMILY ROOM BOASTS A BRICK WOOD BURNING FIREPLACE. THE BACKYARD HAS A BEAUTIFUL IN-GROUND GUNITE AND CONCRETE POOL WITH THE ORIGINAL BRICK PAVER PATIO! HOME IS LOCATED MINUTES TO DOWNTOWN WINTER PARK AND I-4 RAMP.

106 Oakwood Drive, Maitland

32751 Zip Code Lake Front Real Estate & Homes

Browse All 32751 Zip Code FL Lake Front Properties for Sale