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$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
$775,000
4 Beds ⋅ 3 Baths ⋅ Dommerich Hills Fifth Add SubDv. ⋅ 32751 Zip Code
Sought-after Dommerich Hills POOL Home with no HOA! This spacious block-construction residence sits on an oversized lot—over a quarter acre—and offers nearly 3,000 square feet of living space with a rare dual-primary-suite floor plan. The first primary suite is conveniently located on the main level, featuring a private en-suite bath with French doors that open directly to the pool. Upstairs, the second primary suite creates a true retreat with a huge oversized bedroom, walk-in closet, additional closet, custom built-ins, and recently updated bathroom. The large kitchen offers abundant cabinet space, granite counters and a double oven—perfect for holiday cooking and entertaining. Other highlights include a formal dining room, separate family room, and a generous living room with built-ins, fireplace and French doors that lead to the pool and very large private backyard. Fully fenced yard is perfect for pets, or you could building an outdoor kitchen and entertainment area, lots of possibilities. Roof 2021, fresh exterior paint (October 2025), and tons of storage space throughout the home. Large indoor laundry room with tons of cabinetry with new flooring. 2 car garage. The home is equipped with a Ring security system covering the front door, driveway, and backyard. Located in one of Maitland’s most desirable neighborhoods—Dommerich Hills. Zoned for top-rated, A+ schools. Dommerich Elementary, Maitland Middle and Winter Park High. Home is surrounded by multiple parks, including one just minutes away with basketball courts, playground, and picnic area. This is the lifestyle everyone wants!

2550 Big Bend Trail, Maitland
$770,000
4 Beds ⋅ 5 Baths ⋅ Oakleigh 3rd Add SubDv. ⋅ 32751 Zip Code
In the Heart of Maitland Winter Park boundary ~ 0.36 Acre Pool Home ~ 4200 Square Foot ~ 4 Bedrooms ~ 5 Bathrooms ~ Pool Home **For those with vision!** This rare opportunity in Maitland’s coveted Oakleigh neighborhood offers the ideal canvas for renovation or redesign. Surrounded by lakefront estates on an oversized lot, this expansive 4,200 sq ft traditional ranch sits on over one-third of an acre and is filled with natural light. The great room overlooks a private outdoor oasis with a pool, mature landscaping, and a brick-paved patio—perfect for entertaining. The chef’s kitchen features a commercial gas range, double ovens, built-in refrigerator, and a cozy dinette with a wood-burning fireplace—ready for your modern touch. A flexible double-primary split floor plan includes 4 bedrooms, 5 baths, and multiple living spaces, offering endless potential for customization. The primary suite showcases wood beams, hardwood floors, and a sitting area with pool views. The spacious en-suite includes dual showers, walk-in closets, and a skylit garden tub awaiting your personal style. Just minutes from Downtown Maitland, Minnehaha Park, and Lake Maitland, with easy I-4 access, this property offers both prime location and unmatched potential. Whether you’re an investor, designer, or homeowner ready to create your dream home, **51 Oakleigh Lane** is ready to become a masterpiece.

51 Oakleigh Lane, 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
$680,000
3 Beds ⋅ 4 Baths ⋅ Orangedale Park SubDv. ⋅ 32751 Zip Code
HUGE Price Reduction!! There is simply nothing that compares to this deal! This exquisite attached single family home blends contemporary elegance with unbeatable convenience in a truly coveted Maitland address. Just a stroll from Maitland Preparatory School and mere minutes from the vibrant heart of Downtown Winter Park, this residence offers the best of both worlds. From the moment you arrive, you’ll sense the refined lifestyle within. soaring ceilings, abundant natural light, and premium finishes throughout. The chef’s kitchen is a showpiece sleek cabinetry, stone countertops, and top-tier appliances. Entertain effortlessly with open living spaces that flow seamlessly to relaxing patios or balconies. With 3 bedrooms and 3½ baths, each space is a sanctuary. The primary suite impresses with its spa-style bath and custom closets. Upstairs, the laundry is tucked neatly beside the bedrooms for ease and efficiency. Thoughtfully designed storage niches and built-ins complete the picture. The real magic is the location. You’re only 5 minutes from Winter Park’s world-class dining, boutique shops, cultural venues, riverside parks, and Sunday farmer’s market. Stroll through cobbled streets, enjoy al fresco cafés, or catch live music on Park Avenue this home gives you that full lifestyle. Live luxuriously in a community where neighbors share the same roof and an unspoken sense of sophistication reigns. While it feels like condominium living, this is fee simple ownership in a four-unit enclave with NO HOA fees. You get the benefits without the burden. This is more than just a home it’s a statement. Don’t miss your opportunity to own a residence that’s as beautiful as it is brilliantly located.

183 Orange Place, Maitland
$970,000
4 Beds ⋅ 3 Baths ⋅ Dommerich Hills SubDv. ⋅ 32751 Zip Code
Sold data entry only

2031 Chippewa Trail, Maitland
$915,000
4 Beds ⋅ 3 Baths ⋅ Dommerich Hills SubDv. ⋅ 32751 Zip Code
One-story home in Dommerich Hills within walking distance to Dommerich Elementary and Maitland Middle schools. Move-in ready with wonderful pool. Beautifully landscaped.

2021 Chippewa Trail, 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
$765,000
4 Beds ⋅ 3 Baths ⋅ Maitland Grove SubDv. ⋅ 32751 Zip Code
A fantastic 4-bedroom, 2.5-bath home with an office/flex space, located on a prime interior lot in the established Maitland Groves neighborhood. Major systems updated with a 40-year architectural roof (2013), Plumbing Re-pipe (2019); New windows and sliding doors (2023); Newer carpet in bedrooms; HVAC/AC (2006 with New Air Handler Blower Motor (Sept. 2025)), water heater (2008), and a whole-house generator (2008). Highlights include an open floorplan, cathedral ceilings, a cozy fireplace, and a spacious, updated island kitchen, white cabinetry with a breakfast nook. The large laundry/mudroom conveniently connects to an oversized side-entry 2-car garage, perfect for groceries and kids. A flex space overlooking the backyard offers great potential as an office, fitness area, or playroom. Both bathrooms feature double sink vanities, and the primary suite has sliding door access and views of the backyard. The property is landscaped for privacy, featuring a partially covered front entry courtyard and both open and covered patios in the backyard. Located in a top school district near Lake Sybelia Elementary, with easy access to parks, sport courts, bike paths, shopping, restaurants, a hospital, and the I-4 corridor.

380 White Oak Cir, Maitland
$939,000
5 Beds ⋅ 4 Baths ⋅ Dommerich Woods SubDv. ⋅ 32751 Zip Code
Under contract-accepting backup offers. Discover a rare opportunity in Dommerich Woods, a distinguished and established Maitland neighborhood celebrated for its rich heritage. Situated on .33 acre of lushly landscaped grounds, this remarkable property welcomes with paver drive and enjoys a tranquil setting along a peaceful creek connecting Lake Minnehaha and Lake of the Woods - creating an atmosphere of natural elegance and privacy. Re-roofed in 2023, this expansive 5 bedroom, 3 1/2 bath residence offers 4,144 HSF, and WHOLE HOUSE WATER SOFTNER, showcases a versatile TWO-LEVEL design, perfectly suited for refined living and gracious entertaining. The main level opens with a foyer leading into a bright, open living and dining area, where CEILING FANS throughout the main level add comfort and elegance. From here, step out onto the COVERED UPPER DECK with sweeping views of the SCREENED POOL, TROPICAL GARDEN, and serene backyard retreat - an ideal setting for morning coffee or evening gatherings. At the heart of the home, the GOURMET KITCHEN blends style and functionality with SOLID WOOD CABINETRY, a built-in WINE REFRIGERATOR and WINE RACK, granite countertops, and a CENTER ISLAND with SEATING, and REVERSE OSMOSIS WATER SYSTEM under the DOUBLE SINK. The adjacent laundry room offers exceptional storage, keeping household essentials organized. For added convenience , a two-car garage with built-in cabinets and workshop area, adjoins the spacious laundry room that has granite counters and washer and dryer. Also on the main level , adjacent to the primary bedroom with en-suite bath, a bedroom has been thoughtfully converted into a large closet featuring a CUSTOM CLOSET system, providing abundant space for wardrobe organization. Both levels feature inviting WOOD-BURNING FIREPLACES that add ambiance to the living spaces. On the lower level, a spacious family room, kitchenette, study/library/office, two bedrooms, full bath and half bath provide the perfect complement to easy living. Along the hallway, built-in wood shelving creates a refined showcase for books, art, or personal collections. While one bedroom includes a custom built in desk- ideal for work or study, a second bedroom adds flexibility for creative projects. This level opens onto the screened pool and patio area, designed for seamless indoor-outdoor living. Outside, tropical plantings, METERED IRRIGATION, and a winding private walkway leads along the soft murmur of the BORDERING CREEK. An added bonus is the storage room located below the kitchen which is approximately 375 sq.ft. Whether hosting guests or enjoying a quiet evening, this private oasis offers the ultimate backdrop for relaxed Florida living. Enjoy the opportunity to join the Dommerich Beach Civic Association with membership options including access to a private picnic area, boat ramp, canoe and kayak storage, and unforgettable evening sunsets. With its rare combination of design, flexible spaces, and an idyllic setting , this residence presents a unique opportunity to experience the very best of Maitland and Central Florida living. All this is convenient to some of Central Florida's finest schools, shopping, restaurants, parks, entertainment, businesses and more!

791 Sequoia Trail, Maitland
$1,655,000
5 Beds ⋅ 5 Baths ⋅ Lake Colony Ph 01 Rep SubDv. ⋅ 32751 Zip Code
Showpiece Charles Clayton Home in Gated Lake Colony Estates Every detail of this 5-bedroom, 4.5-bath plus office residence was designed to impress, including a full in-law apartment and an outdoor living space that feels like a private resort. Set on a prime corner lot, this home combines timeless craftsmanship with modern finishes: tile roof, travertine downstairs, hardwood upstairs, sleek wrought iron staircase, coffered ceilings, plantation shutters, and designer lighting. The chef’s kitchen is built for both cooking and entertaining—gas stove, double ovens, custom cabinetry, granite counters, oversized breakfast bar, and sunny dining nook. A two-sided stone fireplace connects the office and family room, adding warmth and character. The primary suite is a retreat of its own: spa-style shower with six body sprayers and dual rain heads, a private tankless water heater, and a two-story custom closet built for a true collection. Guests enjoy privacy with a separate stairway leading to a full in-law apartment complete with family room. Step outside to the ultimate backyard: screened, gas-heated pool, tongue-and-groove ceiling patio, outdoor kitchen with grill, sink, granite workspace, storage, TV, and built-in keg fridge. Additional highlights: spotless 3-car epoxy garage with workshop, built-in office cabinetry, 12-foot ceilings, beadboard accents, and a dog run. And the best part? All of this is in close proximity to Orangewood Christian School and just minutes from Winter Park, top-rated dining, and shopping. A rare opportunity to own a true Maitland showpiece.

104 E Lake Colony Drive, Maitland
$1,035,000
4 Beds ⋅ 4 Baths ⋅ Maitland Club Rep SubDv. ⋅ 32751 Zip Code
A truly unique opportunity in the Maitland / Winter Park area, the Maitland Club community features a 24/7 guard-gated entrance for this executive home! This 4 BR, 3.5 BA home has all the features of a dream home, including a downstairs guest/in-law suite with private entry, a large front den for a home office, and a versatile bonus room ideal for a second office, gym, wine room, or hobby space. The renovated chef’s kitchen boasts wood cabinetry, granite counters, stainless steel appliances, an above-range pot filler, island seating, and a 6' x 6' walk-in pantry with custom shelving. Elegant finishes include wood floors throughout, plantation shutters, crown molding, and upgraded millwork. The family room features a cozy fireplace and offers beautiful views of the pool and mature backyard landscaping. The large primary suite showcases a seating area, custom walk-in closet, and remodeled bath with double vanities, beautiful tile work, new cabinetry, and even a window seat. The guest bedrooms on the second floor are generously sized with an updated Jack-and-Jill bath and custom storage solutions built into the closets. Enjoy a private backyard retreat with a resurfaced and heated pool featuring custom lighting, decorative tile, and a relaxing water feature, plus a covered patio and no rear neighbors. Upgrades are countless in this loved home, including ceiling storage and tool cabinets in the oversized 3-car garage, a new roof (2023), replumbed (2022), HVAC replacement (2022), new wood floors, custom closet built-ins, and even fresh paint. Community amenities include tennis, basketball, playground, and proximity to Orangewood PreK-12th grade School with quick access to Winter Park, I-4 Express, and all of Central Florida! Don't miss your chance to claim this dream custom home as your own!

904 Brightwater Circle, Maitland
$855,000
4 Beds ⋅ 3 Baths ⋅ Versailles SubDv. ⋅ 32751 Zip Code
Welcome to Versailles, where timeless architecture meets everyday ease just steps from the shimmering waters of Lake Minnehaha. This beautifully updated home offers peace of mind with a NEWER ROOF, 4-year-old HVAC, NEW IRRIGATION SYSTEM and APPLIANCES approximately 5 years old. Inside, the thoughtfully designed split floor plan ensures privacy for the primary suite, while elegant formal living and dining rooms create the perfect setting for entertaining. At the heart of the home, the chef’s kitchen boasts an island overlooking the inviting family room with custom built-in shelving. Enjoy the screened in lanai located off of the kitchen and family room with plenty of space for multiple seating areas. The versatile 5th bedroom currently serves as a sophisticated study. The private primary retreat features a spacious walk-in closet and a spa-inspired bath with double vanity, separate shower, and soaking tub. Updated secondary bathrooms add to the home’s refined appeal. Beyond the home, enjoy private neighborhood access to Lake Minnehaha—ideal for paddle boating, kayaking, or simply taking in golden-hour sunsets on the PRIVATE DOCK over the water. With Lake Minnehaha visible just across the street, the location is second to none. You’ll also appreciate being zoned for TOP RATED schools and just minutes from Maitland Blvd, I-4, 436, and the area’s best shopping, dining, parks, and recreation. An optional HOA adds flexibility to enjoy the community your way.

939 Versailles Circle, Maitland
$849,000
4 Beds ⋅ 3 Baths ⋅ Highland Park Estates First Add SubDv. ⋅ 32751 Zip Code
sold data only

811 Collie Lane, Maitland
$2,475,000
6 Beds ⋅ 6 Baths ⋅ Packwoods Plan/Maitland SubDv. ⋅ 32751 Zip Code
The Winter Park Chain is the context; the shoreline of Lake Minnehaha is the setting. A three-story, columned home opens with an honest, crafted tone: new low-profile concrete tile roof, operable cypress shutters with hand-forged hardware, Chippendale balustrades, and a beveled front door offering almost 6,200 sq. ft. curated for light, views, and everyday lake living. Inside, the home is bright and airy—sunlight does the work here. A direct foyer sightline leads you to a rear wall of French doors that draw in a calm, even glow of natural light across heart-of-pine floors and disciplined millwork: raised-panel wainscot, multi-step crown molding, and architectural beams. Those doors open to a full-length covered lanai; beyond, a heated saltwater pool and spa step down to a deep backyard and a private dock with a covered boat slip and adjoining lounge deck. The kitchen is built to perform so life feels easy. Morning coffee, weeknight pasta, Saturday crowds, it handles all of it. Sub-Zero refrigeration with additional refrigerator drawers, a Thermador six-burner gas range, two dishwashers, and a warming drawer. Granite counters surround a prep island with rinse sink; the peninsula takes the laptops and late plates. A dry bar with wine cooler ties to the dining room for effortless pours and keeps glassware close at hand. Just off the family room, the primary suite claims a quiet corner and opens to the lanai; coffee at sunrise, warm light at day’s end. A large custom walk-in closet answers storage; the bath finishes the suite with tumbled marble, Kohler fixtures, and a cast-iron vintage tub. At the center of the first floor, a deliberate service run keeps daily life organized: powder bath, temperature-controlled wine cellar, a straight sightline to the first of two laundry rooms and the garage entry ending at a private interior stair to a secluded in-law/guest suite with its own full bath. It’s independent, quiet, and ideal for long stays or live-in support. The main stair brings you to a second level arranged with intent. One wing holds three bedrooms around a shared bath. An office corridor carries you to the lake-view great room under a coffered ceiling; triple French doors open to the full-length upper veranda. Another bedroom on this wing enjoys its own veranda access with a full bath close by. Above it all, the third floor is a generous, flexible loft fit for a screening room, billiards or game lounge, studio, gym, or a collector’s library with practical storage tucked to the edges. Quiet systems match the craft: Cat-5 wiring, surround sound, central vacuum, and two laundry rooms. Recent updates keep the essentials current: new HVACs (2020, 2021) and a new dock (2024). Zoned for Maitland Middle and Winter Park High, this home is tuned to everyday rhythm: water out back, light throughout, spaces that work the way you live. From lanai shade to the last light on the lake, it delivers on its promise—an honest, crafted place where the architecture serves the life it keeps.

604 Minnehaha Lane, Maitland
$975,000
4 Beds ⋅ 3 Baths ⋅ Floridahaven SubDv. ⋅ 32751 Zip Code
This 2436 square foot single family home has 3 bedrooms and 2.5 bathrooms. This home is located at 360 Lake Seminary Cir, Maitland, FL 32751.

360 Lake Seminary Circle, Maitland
$765,000
4 Beds ⋅ 3 Baths ⋅ Dommerich Hills First Add SubDv. ⋅ 32751 Zip Code
This beautifully updated 4 bedroom, 3 bathroom home offers a perfect blend of modern upgrades and charm, situated in the highly sought-after Dommerich neighborhood. No detail has been overlooked in this move-in ready property, with all major systems having been replaced, including: 2023 AC, 2019 roof, replumbed with PVC, new hot water heater, & upgraded electric panel. The open floor plan has a spacious master suite addition by NuDesign, created for ultimate comfort. The renovated kitchen has white cabinetry, sleek GE stainless steel appliances, and granite countertops that seamlessly complement the oversized pantry wall. The kitchen flows into a versatile family room (currently used as a dining room by the owners). The heart of the home is the formal living room featuring a brick wood-burning fireplace and French doors that lead out to the covered patio and screened saltwater pool—ideal for relaxing or entertaining year-round. Enjoy a spacious deck with pavers and plenty of room for lounging. The floor plan includes the original 3-bedroom, 2-bath layout + master suite expansion, offering a sitting space, large walk-in closet, and a spacious bathroom with glass shower. French doors lead out to the pool area, extending the living space to the outdoors. Additional features include wood flooring in all bedrooms plus living/family rooms, updated tile in the kitchen/dining rooms, hurricane shutters and plantation shutters, new double-paned windows, and freshly painted exterior in 2023. This home is connected to sewer, and the cast iron waste lines were coated in 2023 with a lifetime, transferrable warranty for the new owner. Great, convenient location, walking distance to Dommerich Elementary and Maitland Middle School, and zoned for Winter Park High School.

808 Ponca Trail, Maitland
$2,770,000
5 Beds ⋅ 6 Baths ⋅ Poors Add SubDv. ⋅ 32751 Zip Code
Exquisite Lakeview pool home, built in 2021, combines modern elegance and timeless style. Located in the heart of Maitland, with front-row seats to unforgettable sunsets over Lake Sybelia! This Five bedroom, Five and a half bath residence boasts 4,697 square feet of tastefully designed living space. Inside you’re met by a grand foyer and airy layout flooded with natural light, soaring ceilings, wide-plank hardwood floors, custom window treatments, and designer finishes throughout. The gourmet kitchen is an entertainer's delight-equipped with top-of-the-line Wolf and Sub-zero appliances, Taj Mahal quartzite, stunning 12-foot waterfall island, 48” 8 burner gas range with pot filler, large walk-in pantry, with butler’s pantry adjoining the kitchen and dining— the open concept design is perfect for both entertaining and every day living. The living room’s quartz-accented fireplace and sleek glass folding doors provide a seamless flow between indoor and outdoor living. Retreat to the primary suite's spa-inspired bathroom with custom designed walk-in closet, dual vanities, soaking tub and double walk-through shower. A sleek cable railing staircase leads to four generously sized Bedrooms-three with ensuite baths, four bathrooms, a designated Office and versatile Loft/Flex space. Enjoy breathtaking lake views whether working or unwinding! Equally impressive is the beautifully landscaped outdoor living space, with expansive covered lanai, multiple lounge areas, fully equipped summer kitchen, gas fire pit and luxurious salt-water pool and spa. Property features smart home technology, custom closets systems, remote controlled window treatments, surround sound, full-house generator, 500 lb propane tank, 3 car garage with epoxy flooring and so much more! A short walk to Lake Lily and the Maitland Farmers Market, and minutes to Winter Park and I-4. This exceptional home combines refined luxury with an unbeatable location. Don’t miss out on this rare find!

216 N Lake Sybelia Drive, Maitland
$1,153,000
4 Beds ⋅ 3 Baths ⋅ Lake Colony Ph 01 Rep SubDv. ⋅ 32751 Zip Code
Welcome to this custom-built 4 bedroom, 3 bathroom home located in the gated community of Lake Colony Estates. This beautifully remodeled property includes an enclosed private mother-in-law suite or office, perfect for extended family, guests, or remote work. Enjoy a breathtaking courtyard view from the expansive formal living area, featuring an open and airy layout surrounded by manicured landscaping for total privacy and tranquility. This meticulously maintained home includes numerous recent upgrades which include a newer tile roof (2019), two replaced AC units, two replaced water heaters, newer double pane windows, triple-stranded bamboo flooring, newer screened in pool enclosure, brand-new above ground spa, a private putting course and more. The gourmet kitchen is outfitted with updated GE Monogram appliances, a new Bosch dishwasher, and opens seamlessly to a brand-new outdoor kitchen and grilling area. A new Samsung washer and dryer are also included for added convenience. This home is being offered furnished aside from a few personal items and a couple items with sentimental value —just bring your suitcase and move right in. This home is rare find in one of the area’s most exclusive communities. Schedule your private showing today!

1353 W Lake Colony Drive, Maitland
$1,920,000
4 Beds ⋅ 3 Baths ⋅ Maitland Isle SubDv. ⋅ 32751 Zip Code
Experience the ultimate in lake lifestyle living with this beautifully renovated four-bedroom, three-bath home located on the canal to Lake Maitland — one of the most desirable lakes on the Winter Park Chain-of-Lakes. Tucked away on a quiet cul-de-sac just one house from open water, this home offers the perfect blend of waterfront serenity and access to vibrant city amenities. Inside, the residence has been thoughtfully updated over the past six years, preserving its character while incorporating modern finishes. Refinished original hardwood floors flow through the main living areas, and the remodeled kitchen features quartz countertops, a glass backsplash, a Wolf gas cooktop, and opens to a bright, sunlit family room with three sets of French doors that lead to the pool, side deck, and expansive outdoor living areas. The spacious living room and a stylish media/den with a striking marble accent wall provide comfortable spaces to relax or entertain. The primary suite features French doors to the pool and a luxurious en-suite bath with a soaking tub, large glass shower, dual sinks, and a showstopping glass walk-in closet. Two additional bedrooms share a Jack-and-Jill bath, and a fourth bedroom with a full bath adds flexibility. Outdoor living takes center stage with a completely renovated pool featuring a HeatWave heating and cooling system and a sand-blasted marble deck. A generous covered lanai offers plenty of space to relax, grill, and entertain, and includes a 20x15-foot SunSetter motorized awning with LED lighting for shade and ambiance. Enjoy canal-front lounging on the WearDeck composite deck, or hop on your boat or Jet Ski from the covered boathouse with hoist lift and floating dock. Recent upgrades include a new Bosch A/C system (2024) with 10-year warranty and a new roof (2019) with transferrable warranty. Located minutes from Park Avenue in downtown Winter Park, this home also offers quick access to Maitland’s cultural corridor with its growing list of restaurants, Lake Lily Park, the Maitland Public Library, and the popular Lake Lily Farmers’ Market. This is a rare opportunity to enjoy the best of waterfront living in an unbeatable Central Florida location.

210 Shell Point W, Maitland
$2,650,000
5 Beds ⋅ 5 Baths ⋅ Dommerich Estates 2nd Add SubDv. ⋅ 32751 Zip Code
Stunning waterfront residence on Lake Minnehaha, part of the celebrated Winter Park Chain of Lakes! This spacious 5-bedroom, 4.5-bath home is designed for luxurious lakefront living and effortless entertaining. The gourmet kitchen is a chef’s dream, featuring a Thermador 6-burner gas range, GE Monogram side-by-side refrigerator and freezer, Bosch dishwasher, wine refrigerator, and a separate prep area with additional GE oven and dishwasher. The expansive first-floor primary suite offers lake views, a spa-style bath with custom cabinetry, an oversized shower, and a dedicated shoe closet. An additional first-floor bedroom with a private ensuite bath is ideal for guests or in-laws. Upstairs, you’ll find three additional bedrooms, two full baths, and a private office with serene views. Enjoy Florida living year-round with a resort-style outdoor space that includes a covered lanai, sparkling pool and spa, fire pit, and a covered boat dock. Bring your ski boat and jet skis — your backyard is a waterfront playground. Plantation shutters throughout add a classic touch to the interior. Zoned for top-rated Dommerich Elementary, Maitland Middle, and Winter Park High. Rare opportunity to live on the water in one of Central Florida’s most sought-after communities!

591 Dommerich Drive, Maitland
$1,110,000
4 Beds ⋅ 4 Baths ⋅ Dommerich Woods SubDv. ⋅ 32751 Zip Code
This Is It – The Dommerich Gem You've Been Waiting For! Nestled on a beautiful corner lot in one of Maitland's most desirable neighborhoods, this completely renovated 4-bedroom, 3.5-bath pool home is truly a showstopper! From the moment you enter the foyer, you’ll be captivated by gorgeous hardwood floors, plantation shutters throughout, and an abundance of natural light that fills every corner of the home. The open-concept layout is perfect for every day living, featuring custom built-ins and a welcoming family room that flows seamlessly into a cozy bench-style dining area. The heart of the home is the chef-inspired kitchen, boasting a large island with seating for six, gas range, farmhouse sink, ample storage with a built-in desk space. Adjacent to the kitchen is a flexible formal living space—ideal for a home office, playroom, or second entertainment area. Step outside to your private backyard oasis, complete with a covered porch with tongue-and-groove ceilings, sparkling pool, lush tropical landscaping, and your very own putting green! Inside, two secondary bedrooms share a full bath, while a third features a private ensuite that was added during the renovation. The primary suite is a retreat in itself, offering dual custom closets, French doors leading to the backyard, and a luxurious bathroom with a massive marble shower, freestanding soaking tub, and double vanities. As a bonus, a small, climate-controlled office space was added in the garage—perfect for working from home. Located in the heart of Dommerich, you’re just minutes from Park Avenue’s renowned shopping and dining, top-rated schools, and everything that makes this community so special. Don’t miss this rare opportunity to make this home yours!

791 Arapaho Trail, Maitland
$1,399,900
4 Beds ⋅ 5 Baths ⋅ Beg 635 Ft E & 430 Ft N Of Sw Cor Of Sw1/4 Of Ne1/ SubDv. ⋅ 32751 Zip Code
Under Construction. Exquisite One-Story Pool Home with Summer Kitchen | Over 3,200 SF of Luxury Living in beautiful Maitland on an oversized lot! Impeccably designed and ideally located, this stunning single-story estate offers luxurious and refined living space with 4 bedrooms, 3 full baths, 2 half baths, and a private study. The open floor plan showcases rich wood flooring throughout, soaring ceilings, and quartz countertops for a seamless blend of comfort and sophistication. The gourmet kitchen boasts Bosch appliances and quartz counters and flows effortlessly into the spacious great room and dining area—perfect for entertaining. The luxurious owner’s suite features a spa-like bath and generous, dual walk-in closets. Step outside to a true Florida oasis: a resort-style pool and spa, covered lanai, and a fully equipped summer kitchen designed for indoor-outdoor living year-round. Additional highlights include: Designer-appointed finishes Oversized 2-car garage Prime location near top restaurants, shopping, and I-4 access This rare, one-level luxury residence offers timeless design and modern convenience in one of Central Florida’s most desirable locations. Close to endless dining and shopping options, come see this and make it yours today. rendering is an artist's conception and may be subject to change

850 Hillcrest Avenue, Maitland
$3,500,000
Coopers Sub SubDv. ⋅ 32751 Zip Code
Prime mixed-use commercial property perfectly situated between the vibrant cities of Maitland and Winter Park. This centrally located asset offers both visibility and versatility. The listing encompasses a 29-unit multifamily building, adjacent commercial building 429 E. Kennedy Blvd, and a commercial lot 34 N. West St —offering incredible potential for future development, expansion, or mixed-use revitalization. Whether you’re an investor or developer, this is a rare opportunity to be part of a growing community with active revitalization efforts. New roof installed in 2023.

421 E Kennedy Boulevard, Maitland
$1,350,000
4 Beds ⋅ 2 Baths ⋅ Maitland Point SubDv. ⋅ 32751 Zip Code
The home you’ve been searching for has officially hit the market! Welcome to 2047 Howell Branch Road, the four bedroom, two bath home offering 2960 square feet of pure comfort. The beautiful exterior with its striking curb appeal will immediately draw you in before you even set foot inside. Entering through the foyer, you will feel a welcoming ambiance being flanked by a home office on one side and a multi purpose room on the other, flowing right into the wide open living spaces straight ahead. The family room features a brick fireplace, high cathedral ceilings and so much natural light seamlessly connecting to the kitchen, which has been updated to perfection. The large island has a beautiful stainless farmhouse sink and the cooktop encompassed inside the whitewashed brick nook will tempt even the most novice chef into whipping up an extravagant meal. The abundant natural light reflects off the stunning countertops and decorative mirrored backsplash adorning additional countertop space and even more cabinet storage for all of your culinary supplies. The dining area sits right next to the kitchen, centered around a beautiful bay window and wooden beamed ceiling with an artistically designed chandelier. The split floor plan is tastefully done with the master off to one side featuring a large ensuite bathroom with dual closets, a seating area, a large tub and walk in shower. To the other side of the living space is a hallway with the additional three bedrooms, a bathroom, the indoor laundry room with garage access and a flight of stairs leading up to the loft overlooking the downstairs that can be used in a number of creative ways. Exiting through either the main living area or the dining room, you will walk out onto a beautifully redone patio featuring marble tile under cover with a large ceiling fan. The backyard of this home is something out of your imagination, fully encompassed by a newer wood fence and featuring a fire pit and a hand constructed tree house with ninja warrior vibes, not to mention the newly installed heated pool featuring a sizeable sun shelf and color-changing lights to keep the fun going well into the evening hours. The sheer size of the backyard alone will have you continuously coming up with ways to take the fun outdoors. With neighborhood lake access, zoning for top rated schools and close proximity to everything the cities of Maitland and Winter Park have to offer, this is the one you won’t want to miss. Schedule your life-changing showing today!

2047 Howell Branch Road, Maitland
$1,100,000
4 Beds ⋅ 3 Baths ⋅ Versailles SubDv. ⋅ 32751 Zip Code
One or more photo(s) has been virtually staged. Seller may consider buyer concessions if made in an offer & this property qualifies for a credit up to $17,250 through the seller's preferred lender | Welcome to Versailles, where timeless style meets a top to bottom 2025 RENOVATION that redefines luxury living! Taken down to the studs and rebuilt with intention, this private POOL HOME is the one you have been waiting for. Major mechanical updates include: FULL REWIRE & ELECTRICAL (2025) | ALL NEW PLUMBING (2025) | WATER HEATER (2025) | Most windows replaced with HIGH END SLIDING GLASS DOORS (2025) | FRESH EXTERIOR PAINT (2025) | NEW ROOF (2023) | A/C (2014). Inside, the layout is bright, open and effortlessly liveable evidenced in the soaring ceilings and architectural details – including wood beam accents, a dramatic floor to ceiling fireplace, and a catwalk style second floor that creates an elevated yet inviting vibe. The great room connects the family room, kitchen, and dining areas, all with views to the pool and backyard thanks to an entire back wall of windows and sliding doors. OPTIONAL 4TH BEDROOM IS THE FORMAL LIVING ROOM AND CAN BE ENCLOSED AS THE BUYER DESIRES FOR OFFICE/ 4TH BEDROOM NEEDS. The magazine worthy kitchen is equal parts chic and functional featuring solid wood two-tone cabinetry, an OVERSIZED ISLAND WITH BAR SEATING, high end appliances (including an INDUCTION COOKTOP!), and a CUSTOM WALK-IN PANTRY for all your storage needs. Just off the dining area, a cozy sunken living room adds additional versatile space for everyday living or entertaining. Your MAIN FLOOR OWNER’S SUITE is a spectacular retreat; light filled and spacious with a CUSTOM DESIGNED WALK-IN CLOSET and spa-caliber bathroom delivering ZERO ENTRY DUAL MOEN SHOWERS with digital temperature and pressure controls, and sleek finishes throughout. Upstairs, two generous bedrooms and a large guest bath with a free standing acrylic soaking tub and separate shower offer comfort and style for family or guests. Also noteworthy; your laundry room is outfitted with smart, space saving solutions that include a state of the art combination washer/dryer and abundant storage. Outside, your PRIVATE BACKYARD OASIS awaits – a large open air pool with brand new pavers and lush landscaping, all fully fenced on a .30 ACRE LOT with a covered lanai – plus mature trees, a convenient circular driveway and endless curb appeal to round out the exterior. Additional highlights; light-toned ENGINEERED HARDWARD FLOORS and UPGRADED TILE THROUGHOUT, ideal split bedroom layout, attic storage in the garage, an optional HOA and you are ZONED FOR TOP-RATED SCHOOLS. Lake Minnehaha is visible just across the street and you are only minutes from Maitland Blvd, I-4, 436 and the area’s best shopping, dining, several parks and tons of recreation. Style, substance and location, this home is the total package. Schedule your tour today and come experience quiet luxury with a modern edge in your new Maitland pool home!

941 Versailles Circle, Maitland