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$850,000
Lake Maitland Park SubDv. ⋅ 32751 Zip Code
Incredible opportunity to build your dream home on this exceptional corner lot! Walking distance to Winter Park's Park Ave! Lot is located on the corner of Audubon and Magnolia and is surrounded by gorgeous homes. Audubon Rd is a dead end street with no thru traffic. This Maitland address is one block from Winter Park's 32789 zip code. Lot size 70 x 130. Zoned for top-rated schools including Dommerich Elementary, Maitland Middle, and Winter Park High.

1361 Audubon Road, Maitland
$494,500
3 Beds ⋅ 2 Baths ⋅ Druid Hills Park SubDv. ⋅ 32751 Zip Code
Welcome to 370 Sultana Lane, a beautifully reimagined residence nestled within the highly sought after Druid Hills community of Maitland. Thoughtfully renovated from top to bottom with more than $60,000 in improvements, this move-in ready home delivers the perfect combination of modern design, energy efficiency, and long-term value. Step inside to discover a completely redesigned open floor plan filled with natural light streaming through energy-efficient double-pane vinyl windows. New flooring, upgraded lighting, custom blinds, & elegant crown molding is just the start of all that's been done to this home! The showstopper of the home is the stunning, fully renovated kitchen, complete with modern cabinetry, updated appliances, & an contemporary oversized sink.  The spacious family room is anchored by a timeless brick wood-burning fireplace, creating the perfect setting for cozy evenings or gatherings with family and friends. At the front of the home, a flexible living room provides endless possibilities as a home office, media room, playroom, fitness space, or additional living area. Beyond its impressive cosmetic renovations, this home offers exceptional peace of mind with major system updates already completed, including a 2020 roof, newer HVAC system, newer water heater, upgraded electrical panel, PEX plumbing, water softener, and energy-efficient double-pane windows. Outside, fresh exterior paint, new sod, and refreshed landscaping create inviting curb appeal while providing the perfect canvas for your own outdoor oasis. Best of all, there is no HOA, giving homeowners added flexibility and freedom. Perfectly positioned in one of Maitland's most convenient locations, the home is less than a mile from Orangewood Christian School and within two miles of Genesis Sportsplex. Plus, it's only minutes away from Enzian Theater, Lake Lily Park, and the SunRail station. With designer finishes, significant capital improvements, fully paid solar panels, and an exceptional location, 370 Sultana Lane offers a rare opportunity to own a truly move-in ready home where every major detail has already been thoughtfully completed.

370 Sultana Lane, Maitland
$600,000
3 Beds ⋅ 2 Baths ⋅ Oakland Shores 1st Add SubDv. ⋅ 32751 Zip Code
Under contract-accepting backup offers. Seller has received MULTIPLE OFFERS, and are accepting offers until 5pm on Saturday, JULY 11, 2026. Welcome to your own private resort in the heart of Maitland! Perfectly situated on a beautifully landscaped .27-acre lot in the established Oakland Shores neighborhood, this exceptional three-bedroom, two-bathroom home offers close to 1,800 square feet of thoughtfully updated living space designed for both everyday comfort and unforgettable entertaining. The backyard is truly the star of the show, featuring a spectacular saltwater pool and spa completed in 2023. Designed to impress, this outdoor oasis showcases a stunning Tahoe Blue pebble finish, expansive sun shelf, elegant waterfall and scupper features, dramatic integrated fire bowls, and a heater/chiller for year-round enjoyment. The surrounding travertine pool deck, professionally designed landscape lighting, mature landscaping, and fully fenced backyard create an incredibly private setting, while the Paradise Grill summer kitchen(negotiable with the sale) makes outdoor entertaining effortless. The lush, beautifully manicured landscaping is effortlessly maintained by a 10-zone irrigation system with spray heads, back-flow prevention, and convenient Wi-Fi connectivity, allowing you to monitor and control watering schedules from virtually anywhere. Additionally, a comprehensive underground gutter drainage system directs all roof water to the street, minimizing standing water and protecting the home's foundation and landscaping. Inside, the home is equally impressive with an open and inviting layout enhanced by wood laminate flooring installed in 2019, custom white oak interior doors, crown molding, and large picture windows that frame picturesque views of the backyard retreat. The spacious living room, expanded in 2018, features a beautiful wood-burning fireplace added in 2019 along with custom built-in cabinetry and a built-in desk, creating the perfect gathering space. A newly added laundry/utility room(2026) includes the washer and dryer for added convenience. The kitchen is designed for both function and style with custom wood cabinetry, granite countertops, stainless steel appliances, a pantry, and a center island with seating for three, all overlooking the pool through a large picture window. The private primary suite offers custom cabinetry designed for a king-sized bed, custom blackout shades, white oak closet doors, a ceiling fan, and a beautifully remodeled ensuite bathroom completed in 2026 featuring floor-to-ceiling tile, a custom wood vanity, and a spacious frameless glass walk-in shower. Additional highlights include an oversized paver driveway, two-car garage, and an unbeatable location just minutes from Lake Lily Park, the skiable Lake Orienta boat ramp, I-4, and the shopping, dining, and entertainment destinations of Maitland and Winter Park. This is a rare opportunity to own a home where every day feels like a vacation. ROOF - 2016 HVAC - 2018 ELECTRICAL - 2026 WATER HEATER - 2026

623 Woodley Road, Maitland
$735,000
6 Beds ⋅ 3 Baths ⋅ English Estates Unit 3 SubDv. ⋅ 32751 Zip Code
HONEY STOP THE CAR! This Maitland POOL home has EVERYTHING you need and MORE under one roof! Welcome to one of Maitland's most desirable neighborhoods English Estates. This 6 Bedroom, 3 Bathroom estate offers over 2,600 square feet of living space with a Split Bedroom Floor Plan and a Private Pool. This home is Move-In ready and provides comfort with modern style and top of the line updates by offering the perfect combination of luxury and space which is ideal for Large Families, Multi-Generational households, and working professionals seeking a premium residence. Once you step inside, you'll find an Open Concept showcasing the Kitchen, Living Room, and Dining Room with lots of natural light down to the fine details of Wainscoting and Crown Molding. The Kitchen is the Heart of the Home and this Kitchen is surely that! Great space for the whole family to enjoy and gather around the Extra Large Island. The Kitchen comes equipped with Real Wood Cabinets, Granite Countertops, and all major Stainless Steel Appliances including a Gas Stove with Hood Vent, Dishwasher, Fridge, and Microwave. Located off the Kitchen, the Living Room opens up to the Florida Room that leads out to your own Private Pool with Screen Enclosure. The Split Bedroom Floor Plan in this home features 3 Bedrooms on each side of the home, a true even split, giving you a thoughtful layout for everyday living, entertaining, and working from home. The ROOF and AC by Trane with Nest Thermostat are all from 2021. This home comes with Natural Gas at the Stove, Tankless Water Heater, and Dryer. The Extra Long Driveway with Additional Parking on the side provides ample parking for all your vehicles, boats, RV's and toys. Residents enjoy access to A-Rated Schools and a voluntary low-cost HOA. This location is ideal and conveniently located near 1792 which is a short distance to Maitland Community Park and Maitland City Centre where there are local dining spots and recreation activities. This home is also close to Winter Park, Rollins College, AdventHealth, and 10 minutes to Downtown Orlando. Whether you're looking for more space or a new lifestyle, this home delivers! Come enjoy one of Maitland's most established sought-after neighborhoods.

2462 Carolton Road, 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
$235,000
4 Beds ⋅ 2 Baths ⋅ Visconti West Condo SubDv. ⋅ 32751 Zip Code
A rare 4 BR condo with A rated High School could be your next home. Visconti is a high end luxury community featuring a huge lakeside pool with beach entry, fitness center that rivals many commercial gyms, tennis courts, walking paths, and a fantastic clubhouse. The 2nd floor condo has an extremely functional layout that separates the master BR from the other 3 bedrooms. The kitchen is stunning with updated cabinets, solid surface counters and a gorgeous back splash. The common areas feature wood laminate floors with carpet in the bedrooms. Conveniently located in Maitland, this homes is just minutes away from restaurants, shops, I4, 414, and the Maitland business center. A fantastic choice for your main home, a 2nd home or an addition to a rental portfolio.

1460 Lake Shadow Circle Unit 7207, Maitland
$199,000
2 Beds ⋅ 2 Baths ⋅ Visconti East SubDv. ⋅ 32751 Zip Code
Experience resort-style living in the heart of Maitland at the highly desirable gated community of Visconti. This beautifully maintained three-story townhome offers 1,280 square feet of thoughtfully designed living space plus an oversized attached garage, providing the perfect combination of comfort, functionality, and low-maintenance living. The open-concept main living level features luxury vinyl flooring, soaring ceilings, abundant natural light, and a spacious kitchen with stainless steel appliances, updated countertops, tile backsplash, breakfast bar seating, and generous cabinet space. The spacious primary suite offers a large walk-in closet and private bath, while the additional bedrooms provide flexibility for guests, a home office, or growing families. A full-size interior laundry room, ample storage, and neutral finishes make this home truly move-in ready. Visconti residents enjoy an impressive collection of amenities including a gated entrance, resort-style swimming pool, a state-of-the-art fitness center, playground, scenic walking paths, car wash station, and beautifully landscaped grounds shaded by mature oak trees. Conveniently located just minutes from I-4, Winter Park, Downtown Orlando, AdventHealth, RDV Sportsplex, shopping, dining, and entertainment, this home offers the perfect blend of convenience, lifestyle, and value.

1952 Legacy Cove Drive Unit 1952, Maitland
$600,000
2 Beds ⋅ 1 Baths ⋅ Hollieanna Shores SubDv. ⋅ 32751 Zip Code
Data Sold Entry

341 Adams Drive, Maitland
$195,900
1 Beds ⋅ 1 Baths ⋅ Lake Maitland Terrace Apts SubDv. ⋅ 32751 Zip Code
LAKE ACCESS LIVING in one of Central Florida's most desirable locations! Welcome to 1140 S. Orlando Ave E11, a move in ready condo ideally located on the Winter Park and Maitland border in the sought after Lake Maitland Terrace community. Enjoy private access to Lake Maitland, part of the prestigious Winter Park Chain of Lakes, where you can spend your days paddle boarding, kayaking, boating, fishing, or simply relaxing by the water. Community amenities include a brand new lakefront pool, clubhouse available for private events, shuffleboard, putting green, community laundry facilities, COMMUNITY DOCK and additional storage. Inside, you'll find a functional floor plan with separate living and dining spaces, abundant natural light, and a well maintained interior that's ready to enjoy or personalize over time. Whether you're looking for a primary residence, seasonal retreat, or investment opportunity, this condo offers exceptional value in an unbeatable location. Just minutes from Park Avenue and walking distance to local favorites including the Enzian Theater, Eden Bar, Luke's Kitchen and Bar, Antonio's, Francesco's, the Shoppes at Maitland, and beautiful Lake Lily Park. With easy access to downtown Winter Park, downtown Orlando, I 4, shopping, dining, and entertainment, this is low maintenance Florida living at its best.

1140 S Orlando Avenue Unit E11, Maitland
$849,900
3 Beds ⋅ 3 Baths ⋅ Dixie Terrace SubDv. ⋅ 32751 Zip Code
Under contract-accepting backup offers. Perfectly positioned between Maitland and Winter Park, this beautifully maintained 3-bedroom, 2.5-bath pool home offers an exceptional combination of charm, character, and an unbeatable location just minutes from the shops and restaurants of Park Avenue. Warm hardwood floors flow throughout the home, while the impressive two-story family room showcases soaring ceilings and a wood-burning fireplace that creates a welcoming gathering space. Separate living and dining rooms provide flexibility for both everyday living and effortless entertaining. The kitchen is thoughtfully designed with newer stainless-steel appliances and opens to the family room. French doors invite you outside to a private backyard retreat, while the adjacent sunroom is the perfect place to enjoy morning coffee with peaceful views of the pool and lush landscaping. Upstairs, you'll find three spacious bedrooms and two beautifully renovated baths. The primary suite is filled with natural light from a charming bay window and features a spa-inspired bath with marble floors, quartz countertops, dual vanities, and timeless subway tile. Step outside to your own backyard oasis. The covered lanai, complete with a summer kitchen, overlooks a newer saltwater pool and an expansive brick patio, creating the ideal setting for year-round outdoor living, entertaining, or simply unwinding in a private, tranquil setting. Adding to its appeal, the home is located just one house from the Winter Park city limits and is zoned for highly acclaimed Dommerich Elementary, Maitland Middle, and Winter Park High School. Enjoy the convenience of nearby Lake Lily, Enzian Theater, Maitland City Centre, and the boutiques, dining, and vibrant lifestyle of Winter Park's famed Park Avenue. This home offers the rare opportunity to enjoy a peaceful neighborhood setting with the very best of Maitland and Winter Park just moments away.

1783 Sunnyside Drive, Maitland
$550,000
3 Beds ⋅ 2 Baths ⋅ Forest Brook 5th Sec SubDv. ⋅ 32751 Zip Code
This beautifully redesigned and renovated move in ready pool home sits on a quiet cul-de-sac in desirable Maitland. Inside, the open floor plan features a brand-new kitchen with quartz countertops, shaker cabinetry, waterfall island, and stainless-steel appliances. Luxury flooring, remodeled baths, and modern finishes run throughout. Major updates include a new roof, newer HVAC, newer water heater, and French doors that open to a large backyard oasis. A bonus room with a mini split AC offers flexibility for an office or gym. Enjoy the private pool, patio, and proximity to top schools, shopping, and dining.

726 Forest Glen 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
$945,000
5 Beds ⋅ 3 Baths ⋅ Dommerich Hills SubDv. ⋅ 32751 Zip Code
Under contract-accepting backup offers. Welcome to this impressive 5-bedroom, 3-bath split-level POOL home in desirable Dommerich Hills, perfectly nestled on a generous 0.34-acre lot backing to a quiet creek and scenic green space.. Enjoy exceptional privacy and natural beauty with no rear neighbors, creating a peaceful backyard retreat. This remarkable residence offers almost 3400 square feet of living space, providing plenty of room for family living and entertaining. Thoughtfully designed, the home features expansive gathering areas, comfortable bedrooms, and inviting indoor-outdoor living spaces that take full advantage of the beautiful backyard setting. The stunning living room showcases cathedral ceilings with beautiful tongue-and-groove wood detailing, wood burning fireplace creating a warm and inviting atmosphere. French doors open to an expansive outdoor deck overlooking the large backyard and sparkling pool, seamlessly blending indoor and outdoor living. The well-equipped, efficient kitchen is designed for both everyday living and entertaining; appointed with custom shaker cabinetry, granite surfaces, and premium stainless steel appliances serves as the heart of the home. The kitchen boasts a separate breakfast room, with a large picture window capturing beautiful views of the backyard and pool, filling the space with natural light. The oversized primary suite serves as a private retreat, featuring French doors that open to the outdoor deck, an updated en-suite bath, and a large walk-in closet. The secondary bedrooms and guest bath on this level are generously sized and offer ample closet space, providing comfort and flexibility for family members or guests. Downstairs features a spacious family room with a cozy fireplace, two bedrooms, a full guest bath, and a convenient laundry room PLUS wonderful storage room. French doors open to a charming brick terrace overlooking a beautifully manicured backyard that backs onto a peaceful creek. The outdoor space also includes a large swimming pool and a life-size chess/checkerboard area, creating an ideal setting for relaxation and family fun! Recent improvements include windows replaced (2008, 2009), travertine and wood flooring, roof replaced in 2020, A/C' dates2022/2007, freshly painted exterior, and a new sewer connection completed in 2025. A detached two-car garage and long driveway provide abundant parking space, easily accommodating multiple vehicles and making it ideal for guests, recreational vehicles, or a growing family. Ideally located just a short bike ride from highly regarded Dommerich Elementary and Maitland Middle School. Conveniently located just minutes from downtown Maitland, Winter Park, premier shopping, dining, and major roadways, providing easy access to everything Central Florida has to offer. This one-of-a-kind property combines space, privacy, character, and convenience in one remarkable package. Schedule your private showing today and experience all this exceptional home has to offer.

624 Tuscarora Trail, Maitland
$640,000
4 Beds ⋅ 3 Baths ⋅ Orangedale Park Rep SubDv. ⋅ 32751 Zip Code
Location, location!! Discover a rare opportunity to own a single family home plus 2 ADUs, just steps from the iconic Enzian Theater and vibrant Downtown Maitland. This property features three separate units, each with three separate electric meters, water meters and IN-UNIT washer and dryers - a highly sought-after feature for both tenants and owner-occupants alike.With all exterior siding replaced in 2026 on all three units, newer roofs installed in 2026 and 2021, and updated kitchens already completed, this property offers an exceptional turnkey investment with major improvements already in place for long-term peace of mind. This property also has ample parking and an oversized storage shed. The main house is a spacious 2 Bed/1 Bath unit (currently rented for $1,950/month), Unit 2 is a 1 Bed/1 Bath rented for $1,500/month, and Unit 3 is a studio rented for $1,100/month. Current rents are currently below market value and all three units are occupied by long-standing tenants who provide dependable income and minimal turnover. All three leases are set to expire in July and August of 2026, providing future flexibility for an investor or owner-occupant, and two of the tenants have already indicated interest in extending their leases, offering continued income stability from day one. Whether you’re looking to expand your investment portfolio, take advantage of a house-hacking opportunity, or explore the potential for short-term rental income, this property offers exceptional versatility in one of Central Florida’s most sought-after locations. Live in one unit while generating income from the others, or maximize returns through a strategic blend of long-term and short-term rental options. Location truly sets this property apart. Enjoy being just minutes from Winter Park Village, offering endless shopping, dining, entertainment, and a movie theater, while also being a short drive from the charm and excitement of Park Avenue and everything Winter Park has to offer. Residents will love easy access to weekend farmers markets in both Maitland and Winter Park, nearby grocery stores, top-rated restaurants, local boutiques, and convenient commuter routes. The property is also located near Rollins College, adding even more appeal to the location.

245 Orange Place, Maitland
$1,295,000
4 Beds ⋅ 3 Baths ⋅ Kings Row SubDv. ⋅ 32751 Zip Code
Under contract-accepting backup offers. New Price!! Owner Motivated!! Beautifully updated pool home in the sought-after King's Row, Maitland community. This home blends timeless character with modern finishes. The corner lot residence features a three wide driveway, freshly updated landscaping and a commercial grade in ground basketball goal. Exterior paint (2026) creates warm curb appeal. Inside, new wood floors throughout lead to an open living space anchored by an updated kitchen and a classic painted brick wall. The renovated kitchen features quartz countertops, custom cabinetry, pendent lighting, stainless appliances and an updated Fisher Paykel refrigerator. A large island provides seating for four makes entertaining quick and simple. An updated hall pool bath provides easy access for guests both inside and out. Steps away the multi tasked laundry/utility drop/zone is conveniently located off the rear double garage entrance. A commercial grade Speed Queen washer in the laundry/utility room assures your clothes will be clean. Also, an adjacent wall of cabinetry increases the incredible storage in the home. Not only in the front but in the back the corner lot offers an ample spaced backyard retreat. Added is a screened and covered lanai perfect for outdoor parties and gatherings as does the oversized in-ground pool. Zoysia grass/lush landscaping and lighting continue the resort feel. A newer, horizontal stained wood fence adds privacy while maintaining charm. Back inside the living room, a rattan light fixture adds to the ambiance of this bright natural light space. Next to the living space, an office that features a set of French doors lends a place for quiet conversation. The generously sized family room with the afore mentioned painted brick wall is complete with large windows overlooking the sparkling pool and views of three whimsical palms. Down the hallway the newly installed designer wood flooring continues to all bedrooms. Every bedroom just received fresh paint, as well as the newly installed wood floors. All closets feature custom built-ins that add to the level of sophistication/quality in this home. The primary bedroom features another custom painted brick wall with updated sconce lighting. Still another set of French doors lead out to the pool and lanai. The owner's bath features a double vanity with stone counter-tops and updated lighting and faucets. A Mitered frameless glass shower is a great addition to the richness of the space. Zoned for Dommerich Elementary, Maitland Middle, Ninth Grade Center and Winter Park High the schools are highly desirable. A quick and easy close can be the start of your next chapter. This Move-in ready home awaits......

1615 King Arthur Circle, Maitland
$615,000
4 Beds ⋅ 2 Baths ⋅ Forest Brook 5th Sec SubDv. ⋅ 32751 Zip Code
Welcome to 741 Brookside Road in the heart of Maitland! This beautifully updated 4-bedroom, 2-bath pool home offers the perfect blend of modern upgrades, spacious living, and an unbeatable location. No expense was spared during the home's extensive renovations, creating a truly move-in-ready property that combines quality craftsmanship with timeless style. The recently remodeled kitchen is a true showpiece, featuring solid wood cabinetry, elegant Taj Majal granite countertops, upgraded appliances, and abundant workspace for cooking and entertaining. Recent improvements throughout the home include fresh interior paint, a newly renovated guest bathroom, updated plumbing, and a new roof installed in 2024, providing peace of mind for years to come. At the heart of the home is an enormous Florida Room, offering exceptional space for gathering with family and friends while overlooking the tropical backyard retreat. Step outside to your private oasis, complete with a sparkling pool and fountain surrounded by lush landscaping that creates a serene, resort-style atmosphere. Situated on a large fenced corner lot with no HOA, this property offers both privacy and freedom. Its fantastic Maitland location places you just minutes from shopping, dining, parks, and major roadways, making everyday living both convenient and enjoyable. You will be hard-pressed to find another property in this location and price range that offers this level of attention to detail, quality of construction, and thoughtful upgrades throughout. Every improvement has been carefully selected to create a home that is as functional as it is beautiful. Move-in ready and loaded with updates, this rare opportunity combines comfort, style, and outdoor living in one exceptional package. Schedule your private showing today and discover everything this beautiful Maitland home has to offer! Square footage includes Florida Room of 336 square feet not included on tax records.

741 Brookside Road, Maitland
$800,000
3 Beds ⋅ 3 Baths ⋅ Lakewood Shores 1st Add SubDv. ⋅ 32751 Zip Code
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
$1,199,000
5 Beds ⋅ 4 Baths ⋅ Highland Park Estates First Add SubDv. ⋅ 32751 Zip Code
Completely reimagined and renovated, this artfully crafted stunning 5-bedroom, 4-bath residence offers approximately 2,695 square feet of on a spacious corner lot in one of Maitland's most desirable established neighborhoods. The home features an exceptional blend of modern design, luxury finishes, and functional living spaces, including a sparkling pool and expansive outdoor entertaining areas. Step inside to discover an impressive open-concept floor plan highlighted by wide-plank luxury flooring, designer lighting, oversized windows, and a dramatic double-sided tiled fireplace that serves as the centerpiece of the main living areas. The gourmet kitchen has been thoughtfully designed with Kitchen-aid "Black-Ore" Professional series applainces, custom shaker cabinetry, quartz countertops, a large center island, designer backsplash, butlers pantry with wine fridge, and abundant storage, creating the perfect space for everyday living and entertaining. The spacious primary suite offers a private retreat with generous proportions, elegant finishes, and a beautifully appointed spa-inspired bathroom featuring dual vanities, custom cabinetry, a frameless glass walk-in shower, and designer fixtures. Additional bedrooms provide flexibility for family, guests, home offices, or multi-generational living. Outdoor living is equally impressive with a screened covered lanai overlooking the newly resurfaced pool and expansive paver deck, creating a resort-style setting ideal for entertaining year-round. The large fenced backyard offers plenty of room for recreation, pets, and outdoor enjoyment. Located just minutes from Park Avenue, Winter Park, Maitland City Centre, top-rated schools, dining, shopping, and major roadways, this turnkey residence offers luxury living in a prime Central Florida location. A rare opportunity to own a fully renovated pool home that combines timeless architecture with today's most sought-after finishes and amenities.

2491 Lauder Drive, Maitland
$1,499,000
5 Beds ⋅ 4 Baths ⋅ Replat Blk B Poors Add SubDv. ⋅ 32751 Zip Code
Under contract-accepting backup offers. A premier street offering an accessible lifestyle to Maitland’s vibrant downtown corridor, known for its community events, restaurants, Lake Lily Park, the beloved independent Enzian Theater and within view of Lake Sybelia. This custom home was completely rebuilt in 2007, adding significant square footage and incorporating a timeless transitional design. Five bedrooms, four baths, stretching across 4,814 square feet with bonus space, there are many ways to make it your own. Inspired by classic Charleston architecture with Florida influences, the exterior features French doors across the front and rear elevations, lantern-style lighting and a metal roof that enhance the home's charm while filling the interiors with natural light. Shutters and upper-level balconies at both sides of home complete the design. Enter inside to a sweeping staircase with elegant iron details, with neutral travertine flooring that flows throughout the main level and finished with volume ceilings. The kitchen, living and dining spaces blend seamlessly together, complemented by an additional sitting room with privacy doors that provide flexible living options. The kitchen features 42-inch custom cabinetry with glass-paneled doors, granite countertops, a farmhouse sink and high-end stainless-steel appliances. Generous laundry and pantry storage are bonus. The dining area showcases rich hardwood flooring, plantation shutters, built-in surround-sound speakers and direct access to outdoor living spaces. The first floor includes two bedrooms with a shared bath, along with an additional hallway guest bath. Upstairs, beautiful wood floors anchor the rooms, and the spacious primary retreat opens to a private balcony spanning across the back of home and with pool views. An expansive walk-in closet provides exceptional organization, while the primary bath features dual vanities, a rain shower with bench seating and a classic clawfoot tub. Additional upstairs laundry stack for convenience. Secondary bedrooms are spacious and full of light, and great closet storage and additional loft are a bonus. Outdoor living centers around a covered porch overlooking the pool, complete with travertine decking and dramatic fountain features. An additional pool house enhances the backyard and offers endless possibilities for guests, entertaining or a private workspace. Outdoor speaker system adds to the ambience. Additional improvements and features include a newer metal roof (2020), two HVACs (2021), water heater (tankless Rinnai installed by Maitland/Winter Park plumbing), plantation shutters throughout, a freshly painted interior, an extensive interior and exterior lighting package, and thoughtfully designed low-maintenance landscaping featuring front-yard turf, mature plantings and clean rock-bed borders. Exterior ceramic paint has a lifetime warranty. Main floor and primary suite have ceiling-installed concert speakers and outdoor speakers. Lower-floor speakers have individual room controls and are served by a pantry stereo system. This exceptional home offers a desirable location with convenient access to major roadways. Zoned for sought-after schools including Lake Sybelia Elementary, Maitland Middle School and Edgewater High School, a designated magnet school, Park Maitland elementary school, and JCC community center and school. A rare opportunity, this home is a standout in one of Maitland’s special neighborhoods.

255 W George Avenue, Maitland
$210,000
2 Beds ⋅ 2 Baths ⋅ Visconti East Bldg 27 SubDv. ⋅ 32751 Zip Code
Visconti Condo - Gated Community with lots of amenities only 8 miles from Downtown Orlando. This community situated on the north shore of Lake Shadow offers swimming pool, fitness center, clubhouse, tennis and basketball courts. Conveniently located close to I-4 and Maitland Blvd. Multi level home features an open floor plan with kitchen living/dining and office on main 2nd floor and 2 bedrooms 2 bathrooms on the 3rd floor. This home also features an attached 2 car garage with plenty of room for your vehicles or extra storage. HOA includes exterior maintenance, landscaping, valet trash, water, sewer and pest control.

2847 Shadow View Circle Unit 2847, Maitland
$440,000
3 Beds ⋅ 2 Baths ⋅ Pindar Sub SubDv. ⋅ 32751 Zip Code
Under contract-accepting backup offers. Inside, the home opens into a bright and airy open-concept living space highlighted by high tray ceilings, recessed lighting, oversized glossy tile flooring, and an abundance of natural light. The seamless flow between the living, dining, and kitchen areas creates the perfect setting for both entertaining and everyday luxury living.

206 Moseley Avenue, Maitland
$665,000
3 Beds ⋅ 2 Baths ⋅ Highland Park Estates First Add SubDv. ⋅ 32751 Zip Code
Welcome to this beautifully maintained 3 bedroom, 2 bath pool home offering 2,229 square feet of living space in the highly sought-after Dommerich neighborhood of Maitland. The heart of the home is the spacious kitchen featuring knotty pine cabinetry, granite countertops, a gas range, stainless steel appliances, a breakfast bar, and an elegant tray ceiling. The kitchen opens seamlessly to the family room, where a stunning brick accent wall showcases a cozy fireplace and a unique alcove perfect for indoor grilling and entertaining. A separate living room offers additional gathering space with its own fireplace and custom built-in bookshelves. The formal dining room is highlighted by a beautiful chandelier. French doors lead you to a spacious bonus room built in 2025, which is filled with natural light from new windows, providing endless possibilities for a home office, playroom, or flex space. Step outside to your private backyard retreat featuring a sparkling 10-foot-deep pool surrounded by classic herringbone-style pavers, creating the perfect setting for relaxation and outdoor entertaining. An outdoor storage shed provides added convenience. Recent updates include a brand-new roof (2026), newer windows, attractive wood shutters throughout, AC (2015), and water heater (2015) and indoor laundry room. Located within the highly acclaimed Dommerich Elementary, Maitland Middle, and Winter Park High School districts, this home offers the perfect blend of character, comfort, and location—don't miss this rare opportunity to make it yours.

830 Longhaven Drive, Maitland
$410,000
3 Beds ⋅ 2 Baths ⋅ English Estates Unit 2 SubDv. ⋅ 32751 Zip Code
Virtually Staged. HUGE PRICE IMPROVEMENT!!! Move-In Ready Maitland Gem in English Estates! Welcome home to this charming 3-bedroom, 2-bath residence offering convenient one-story living in the highly desirable English Estates community. Blending modern updates with a touch of mid-century modern character, this home is truly turnkey. Step inside to find luxury vinyl plank and ceramic tile flooring throughout—no carpet anywhere. The updated kitchen features granite countertops, 42-inch cabinetry, stainless steel appliances, and a breakfast bar perfect for casual dining and entertaining. The spacious living room flows seamlessly into the dining area, creating an open and inviting atmosphere. The private primary suite includes an en-suite bathroom, while the generously sized secondary bedrooms provide flexibility for family, guests, or a home office. A separate den/family room offers additional living space and opens to a covered, screened porch overlooking the expansive fenced backyard—ideal for outdoor gatherings, pets, and play. Major updates provide peace of mind, including New Roof (2024) HVAC System (2021) Whole-House Repipe (2021) Irrigation System (2022) Septic Drain Field (2018) Double-Pane Windows, New Sod (2026) Additional features include a 2-car garage, paver driveway, covered front porch, and fresh paint. Conveniently located near shopping, dining, parks, and major roadways, with easy access to Winter Park and surrounding Central Florida attractions. Plus, enjoy the benefit of highly regarded Seminole County Public Schools. Beautifully updated, exceptionally maintained, and truly move-in ready—this is a home you won't want to miss!

1291 Oxford Road, Maitland
$180,000
2 Beds ⋅ 2 Baths ⋅ Cherrywood Gardens SubDv. ⋅ 32751 Zip Code
Sold data entry only.

339 Cherrywood Gardens Drive Unit 339, Maitland
$119,900
Coffins SubDv. ⋅ 32751 Zip Code
Vacant parcel likely and ideally suitable for RV, Boat and other residential storage uses. Recorded 14' access easement to Ridgewood Avenue. Partially fenced parcel. Sign on property visible from Ridgewood Avenue. MOTIVATED SELLER WILL PROVIDE FINANCING TO QUALIFIED BUYER. LOW TAXES (Legal Description to be revised to reflect recent sale.)

Ridgewood Avenue, Maitland
$484,000
3 Beds ⋅ 2 Baths ⋅ Winfield SubDv. ⋅ 32751 Zip Code
Welcome to 2155 Fennell Street, a beautifully renovated pool home nestled in the desirable Maitland community. This move-in ready residence has undergone an extensive transformation, offering the perfect blend of modern elegance, functionality, and Florida lifestyle living. From the moment you arrive, you'll appreciate the brand-new roof, new driveway, fresh exterior paint, and impressive curb appeal. Inside, soaring vaulted ceilings and abundant natural light create a bright and inviting atmosphere. The open-concept floor plan features luxury vinyl plank flooring throughout, designer lighting, and fresh interior paint. The fully remodeled kitchen is the heart of the home, showcasing quartz countertops, custom cabinetry, stainless steel appliances, and a spacious breakfast bar overlooking the main living areas. The primary suite offers a private retreat with a beautifully updated ensuite bath featuring dual vanities, designer finishes, and a stunning walk-in shower. Additional bathrooms have been tastefully renovated with modern fixtures and custom tile work. Step outside to your private backyard oasis complete with a resurfaced swimming pool, screened lanai, and fully fenced yard—perfect for entertaining, relaxing, and enjoying year-round Florida sunshine. Conveniently located near shopping, dining, parks, major highways, and top area amenities, this exceptional property offers the rare opportunity to own a truly turnkey home in one of Maitland's most sought-after locations. Schedule your private showing today and experience this stunning home.

2155 Fennell Street, Maitland
$225,000
2 Beds ⋅ 2 Baths ⋅ Park Lake Twnhs SubDv. ⋅ 32751 Zip Code
Under contract-accepting backup offers. Maitland's Hidden Gem! Discover comfort, style, and convenience in this BEAUTIFULLY MAINTAINED 2-bedroom, 1.5-bath condo in the desirable Park Lake Townhouses community of Maitland with NEW A/C 2026 and NEW Water Heater 2026. Located minutes from Park Ave, Trader Joes, Lifetime Fitness and all Winter Park/Maitland has to offer! Offering the FEEL OF A TOWNHOME with two spacious levels, a private patio, and a one-car garage, this home is tucked away in a QUIET LOCATION with PEACEFUL GREEN SPACE VIEWS from the front. Step inside to find EASY-CARE TILE FLOORING throughout the main level and a bright, welcoming Living Room filled with NATURAL LIGHT from the large front window. A convenient half bath and SPACIOUS CLOSET are located just off the hallway before the home opens into the Dining and Kitchen areas. Perfect for both everyday living and entertaining, the Dining area features sliding glass doors leading to a PRIVATE FENCED PATIO, creating a wonderful outdoor space for morning coffee, grilling, or relaxing evenings. The patio also provides direct access to the ATTACHED ONE-CAR GARAGE. Just off the Dining area, you'll find a DEDICATED LAUNDRY ROOM complete with an included washer and dryer. The beautiful Kitchen is sure to impress with its abundance of cabinetry, GRANITE COUNTERTOPS, stainless steel appliances, CHIC TILE BACKSPLASH, and center island that adds both functionality and style. Upstairs, two generously sized bedrooms provide comfortable retreats. The Primary Bedroom features ATTRACTIVE HARDWOOD FLOORING, while the second bedroom is carpeted for added comfort. Both bedrooms offer DOUBLE MIRRORED CLOSET DOORS and share a well-appointed en suite bath. FROSTED GLASS-PANELED INTERIOR DOORS throughout the home add a modern and distinctive touch. Adding even more value and peace of mind, the home features a NEW AC SYSTEM and NEW WATER HEATER. Residents of Park Lake Townhouses enjoy a SPARKLING COMMUNITY POOL along with HOA-covered trash collection, lawn care and exterior maintenance, including the roof, making for a LOW-MAINTENANCE LIFESTYLE. Ideally located, you're just minutes from the boutiques, restaurants, and cafés of PARK AVENUE IN WINTER PARK, as well as CULTURAL DESTINATIONS such as Rollins College, Morse Museum of American Art, and Winter Park Scenic Boat Tour. Nearby shopping, dining, and entertainment options abound at MAITLAND CITY CENTRE, while commuters will appreciate EASY ACCESS to I-4, SR 414, and downtown Orlando. With its STYLISH UPDATES, private outdoor space, attached garage access, and EXCEPTIONAL LOCATION near some of Central Florida's most beloved destinations, this CHARMING residence is ready to welcome you home. Act quickly—this GEM won't last long!

892 Park Lake Circle Unit 69, 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
$405,000
4 Beds ⋅ 2 Baths ⋅ Indian Hills Unit 1 Rep SubDv. ⋅ 32751 Zip Code
Discover a beautifully transformed 4-bedroom, 2-bath Maitland gem, a turnkey showpiece that blends modern style, smart upgrades, and undeniable curb appeal. The home greets you with a fresh look, mature landscaping, manicured hedges, and a custom front deck with modern horizontal railing, creating a welcoming entry and the perfect spot to enjoy your morning coffee. Step inside to an open and airy layout with abundant natural light, wood-look flooring, updated lighting fixtures, and multiple living areas ideal for both everyday living and entertaining. The renovated kitchen features white shaker cabinetry, modern countertops, stylish backsplash details, stainless steel appliances, and ample cabinet space. The dishwasher and oven were recently updated between 2022 and 2024. The kitchen flows seamlessly into the dining and living areas, creating a functional and inviting layout. The home offers spacious bedrooms along with versatile flex spaces perfect for a home office, guest room, or additional living area. The primary suite includes an updated ensuite bathroom with a glass-enclosed walk-in shower and a custom-designed primary closet with built-in organization. Out back, enjoy a fully refreshed backyard featuring brand new sod, a brand new paver patio, and a covered, screened back porch ideal for relaxing or entertaining year-round. Additional upgrades include a brand new driveway, solar panels for energy efficiency (to be paid off in full by the sellers at closing upon an accepted offer), smart home features, updated bathrooms, and modern finishes throughout. Adding to the appeal, HOA membership is optional, offering buyers the freedom of homeownership without mandatory HOA dues or restrictions. Conveniently located near shopping, dining, parks, and major roadways, this beautifully maintained Maitland home combines comfort, functionality, and contemporary style in one of Central Florida's most desirable communities.

1327 Chipola Trail, 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