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$519,999
4 Beds 3 Baths Winfield SubDv. 32751 Zip Code
Welcome to 1776 Bobtail Drive, a home that offers an easy, natural flow and a layout designed for everyday living. This property is now being reintroduced with a refreshed presentation and a full 3D walkthrough experience, giving buyers the ability to explore every space at their own pace before stepping inside in person. Inside, the home features an open-concept layout where the kitchen, dining, and living areas connect seamlessly, creating a comfortable and functional main living space. Upstairs, generously sized bedrooms offer flexibility for families, guests, or home office needs, while the overall layout supports a wide range of lifestyles. Located in highly desirable Maitland, the home offers convenient access to shopping, dining, major roadways, and all Central Florida amenities. Private showings available upon request.they’ve been waiting for.

1776 Bobtail Drive, Maitland

$338,000
3 Beds 2 Baths Branch Tree SubDv. 32751 Zip Code
Charming three bedroom, two bath home in the heart of Maitland! Roof and AC both updated in 2021. This home features an open layout with great natural light and an easy, flowing floor plan. All new kitchen appliances and cabinets installed 2022. The living spaces feel airy and inviting, with newly refinished wood flooring, vaulted ceilings and a split floor plan. Outside, enjoy a fully fenced backyard, ideal for pets, play, or creating your own outdoor oasis. The screened-in covered porch is a total vibe, perfect for morning coffee, relaxing evenings, or hosting friends year-round Florida style. Whether you're a first-time buyer, downsizing, or looking for a smart investment, this home checks all the boxes with comfort, style, and location. Conveniently located near shopping, dining, and major roadways, you’ll love the accessibility and laid-back Maitland lifestyle.

410 Poplar Court, Maitland

$899,000
4 Beds 4 Baths Dommerich Hills SubDv. 32751 Zip Code
NEW PRICE…NEW OPPORTUNITY!! This beautiful, impeccably maintained and updated four bedroom and three and a half bath pool home absolutely has it all, including the added benefit of new electrical wiring throughout. Perfectly located in Maitland’s much sought after Dommerich neighborhood and walking distance to top rated elementary and middle schools. This attractive split-floor plan offers for spacious bedrooms and three full baths on the first level and a bonus room/5th bedroom with half bath on the second level. The gorgeous kitchen, boasts handsome, solid wood cabinets, granite countertops, and stainless steel appliances with double ovens. The first floor open layout includes a large dining area with brick fireplace leading into a wonderfully sized family room with fireplace and custom built-ins. Newly installed double pane, hurricane proof French doors brings in tons of natural light and leads out to your private oasis, including the newly resurfaced pool with new pool pump and filter, brick paver deck, open patio, and super fun gazebo with gas grill and nighttime lighting for entertaining! Awesome potential to install gas into the kitchen, as well. This home is fully supported by a new Generac system, never to be without power! Entire interior just freshly painted and new carpets installed in bedrooms and bonus room. Newer ROOF (2021), HVAC (2020) and tankless water heater. Samsung washer and dryer also included. Gorgeous architectural landscape with LED lighting add to its charm and warmth. This opportunity does not come along often and is absolutely MOVE-IN READY! Look forward to meeting you there!

2112 Chippewa Trail, Maitland

$299,000
2 Beds 2 Baths Sun Bay Club Condo SubDv. 32751 Zip Code
Elegantly renovated two-bedroom, two-bath second-floor condo in the gated community of Sun Bay Club on Lake Destiny in Maitland. Vaulted ceilings and abundant windows create a bright, airy atmosphere throughout. The gourmet kitchen has been fully updated with 42-inch custom hardwood cabinets, Zodiaq (Cambrian) quartz countertops, a Kohler farmhouse sink, stainless steel appliances, and porcelain wood-plank floors. The kitchen opens to the dining and living areas, featuring a built-in desk, wood-burning fireplace, custom built-ins, clerestory windows, and triple sliding doors leading to a private balcony with a storage closet. The split floorplan includes the primary suite with a walk-in closet and a renovated bath with dual vanities, hardwood cabinets, designer fixtures, a glass-block shower, and natural light from a private skylight. The secondary bedroom has two wall closets and an upgraded bathroom with custom cabinets, a tub, and a skylight. Meticulously maintained with pride of ownership reflected throughout. Features include double-door entry, knockdown ceilings, designer finishes, ample storage, and an interior laundry closet. Additional updates include a new Carrier AC (2023), a new hot water heater (2025), and a new tile roof with gutters, downspouts, and skylights (2024). Sun Bay Club offers a beautiful lakefront pool, lake access with a boat ramp, a tennis court, a dog park, a community meeting room, and a car wash area for residents. Its central location is just minutes from I-4, RDV Sportsplex, Publix, shopping, and dining. Downtown Maitland, Winter Park, and Orlando are only a short drive away.

1000 Winderley Place Unit 239, Maitland

$578,000
3 Beds 4 Baths Oakland Shores SubDv. 32751 Zip Code
Virtually Staged. Welcome to 502 Oak Lane in Maitland, a beautifully updated 3 bedroom, 3.5 bathroom pool home offering comfort, character, and peace of mind. Thoughtfully improved throughout, the home features fully updated plumbing, including the replacement of the original cast iron plumbing, along with a brand-new pool pump. Inside, you will find a well-designed layout with spacious living areas, updated finishes, and abundant natural light. Each bedroom has access to its own private bathroom, providing excellent privacy and flexibility for family members, overnight guests, or a home office. The home has been meticulously maintained and is truly move-in ready. Step outside to your private backyard oasis, complete with a swimming pool that is perfect for relaxing, entertaining, or enjoying Florida living year-round. Located on a quiet street in Maitland, the home is approximately 10 minutes from Winter Park and offers convenient access to major highways, shopping, dining, and everyday conveniences. This is a rare opportunity to own a fully updated pool home in one of Maitland’s most desirable and centrally located areas.

502 Oak Lane, Maitland

$329,900
3 Beds 3 Baths Villas Lake Destiny SubDv. 32751 Zip Code
Under contract-accepting backup offers. Back on the market through no fault of the property. Recently appraised at $340,000 and inspections were completed without issue. A great opportunity for a qualified buyer seeking a smooth transaction and quick closing. Tucked into one of Maitland's most coveted lakefront enclaves, this beautifully updated townhome sits within a quietly maintained, tree-lined setting with direct access to Lake Destiny, a private community boat ramp, resort-style pool, and tennis courts, all just minutes from I-4, the 414, RDV Sportsplex, and the dining and shopping corridors of Maitland Center. First impressions set a private and secluded tone with a wrought-iron gated courtyard leads to a covered entry porch before you reach the front door. Inside, soaring vaulted ceilings and a dramatic arched transom window above the sliding glass doors flood the main level with natural light, creating an airy, open feel that far exceeds the square footage on paper. Wide-plank tile flooring runs throughout the main living areas, connecting the open living and dining spaces to a thoughtfully updated kitchen featuring white shaker cabinetry with crown accents, solid stone countertops, stainless steel appliances including a French door refrigerator and built-in microwave, pendant lighting above the breakfast bar peninsula, and a subway tile backsplash. The sliding doors open directly to a private screened patio framed by mature landscaping, creating the kind of indoor-outdoor flow that defines Florida living at its best. Upstairs, three generously sized bedrooms each offer ceiling fans, ample closet space, and brand new carpet and paint. The primary suite stands out with a 26ft footprint, two closets including a walk-in, and an ensuite bath featuring dual vanities, a full-wall vanity mirror, and a walk-in shower. Two additional bedrooms and a full bath complete the upper level, with the layout providing genuine separation and privacy between spaces. Back on the main floor, a versatile 9x9 bonus room with indoor laundry handles the day-to-day, and the full-size washer and dryer convey. The big-ticket items are handled: 30-year tile roof replaced in 2023, HVAC installed in 2020, and brushed nickel fixtures updated throughout. The one-car garage with additional driveway parking and the gated courtyard entry give this unit a sense of privacy and security rare in townhome living. Whether you are looking for a low-maintenance primary residence, a lock-and-leave second home, or a smart investment in a well-managed community with real amenities and a lakefront address, this one makes an easy case.

1010 Winderley Place Unit 127, Maitland

$120,000
3 Beds 2 Baths Carrington Park A Condo SubDv. 32751 Zip Code
Welcome to this spacious 3-bedroom, 2 bath main floor condo in Carrington Park, offering comfort, convenience and strong investment potential. This unit features numerous updates including a new HVAC system, new front door, new tub/shower combo and new updated bathroom vanities. The kitchen has been refreshed with new cabinets, updated countertops and newer appliances, along with some new flooring throughout. The open layout provides generous living and dining space, while the screened in porch offers a relaxing outdoor retreat. With three well-sized bedrooms and easy ground floor access, this condo is ideal for anyone seeking low maintenance living in a desirable community. Carrington Park offers inground pool, playgrounds, green space, security guard, fitness center and is in the heart of Maitland.

2423 Branch Way Unit 105, Maitland

$485,000
3 Beds 3 Baths Enclave/Maitland A-F SubDv. 32751 Zip Code
Welcome to this beautiful Mediterranean-style townhome in the exclusive, gated community of Montacino in Maitland, Florida. Updated 3 bedroom, 2.5 bath home overlooking Lake Charity. Expansive views of the lake are seen from the front porch, two bedrooms and the dining room. Separate dining room with tons of natural light. Open concept kitchen with updated cabinets and stainless steel appliances. The large family room is open to the kitchen for ease of entertaining. Situated between the garage and your back door is an open air, private courtyard. Enjoy a two and a half car garage with full attic for additional storage. The second floor includes three bedrooms, finished laundry with closets that have been professionally customized. Secondary bedroom boasts a Murphy bed for guests with build-in storage. You will enjoy resort style living with the sparkling community pool and tranquil walks along the shores of Lake Charity. Extra guest parking is located just outside the garage. Internet/TV package and lawn care included. Located just 1/4 mile from I-4 and the Maitland Boulevard exchange with easy access to Winter Park, downtown Orlando and Altamonte Springs. Close by is Trelago Market where the new Trader Joes is being built. A must see property.

1106 Charming Street, Maitland

$824,900
5 Beds 3 Baths Dommerich Hills 6th Add SubDv. 32751 Zip Code
Welcome to Dommerich Hills, where modern style meets everyday comfort. This beautifully renovated home offers the freedom of **NO HOA** and has been thoughtfully updated from top to bottom. From the paver driveway and elegant double-door entry to the bright, open-concept interior, every detail has been designed to make you feel at home. The heart of the home is a stunning chef-inspired kitchen featuring sleek custom cabinetry, stainless steel appliances, and a striking waterfall island with custom wood accents,perfect for entertaining family and friends. The spa like bathrooms has glass-enclosed showers, contemporary fixtures, and designer finishes that create a relaxing retreat. Step outside and discover your own private Florida oasis. A covered lanai overlooks the sparkling pool and expansive paver patio, creating the ideal space for outdoor dining, weekend gatherings, or simply unwinding in the sunshine. Conveniently located just minutes from major highways, shopping, dining, and entertainment, this beautifully renovated home combines modern design with everyday functionality. Schedule your private showing today and experience everything this exceptional property.

2801 Waumpi Trail, Maitland

$599,000
2 Beds 2 Baths West Cove Condo SubDv. 32751 Zip Code
TURN KEY AND RENOVATED IN SOUGHT-AFTER WEST COVE!! Wake up to breathtaking sunrises with a stunning, unobstructed view stretching across Lake Maitland—the largest lake in the highly sought-after Winter Park Chain of Lakes—from this beautifully renovated, truly turnkey condominium. All flooring, bathrooms, fixtures, paint, AC, water heater, sliding door to balcony, kitchen/appliances, and closet systems have been painstakingly updated to the highest level, making for an unparalleled opportunity to simply move right in and begin enjoying immersive lake views. The primary suite has been reimagined and has its own ensuite bath and a new built-in closet with copious storage, complete with signature views of Lake Maitland. This spacious residence offers an ideal central location, just moments from an array of dining options, Lake Lily Park, Enzian Theater, and convenient access to Interstate 4 via Lee Road or Maitland Boulevard. The monthly association fee—lower than most lakefront communities—provides exceptional value and includes access to lakefront docks (with boat slips available on a first-come basis), a fitness center, an inviting lobby for entertaining, a heated pool and spa, a grilling area with seating, storage for canoes, kayaks, and paddleboards, assigned and guest parking, laundry facilities on every floor, Spectrum cable and internet, as well as water, sewer, and trash services. This property may be under audio/visual surveillance.

1100 S Orlando Avenue Unit 306, Maitland

$745,000
4 Beds 3 Baths Dommerich Estates 1st Add SubDv. 32751 Zip Code
In the heart of Dommerich, this thoughtfully renovated mid-century pool home offers deeded access to the Winter Park Chain of Lakes & a well-executed floor plan designed for everyday living. Set on a .20-acre lot measuring 79’ x 111’, the home balances indoor comfort with outdoor livability, beginning with a welcoming front entry that opens to a casual foyer. To the left is a shared formal living and dining space filled with natural light from large-format windows. Wide plank engineered wood flooring, charming built-ins & updated finishes continue throughout the main living areas, creating a cohesive & visually consistent interior. Toward the back of the home, the layout transitions to a family room & adjoining Florida room, which, when used together, create a spacious secondary living area, or may function separately as a family room, casual dining area, office or reading room, all overlooking the pool and functionally connected to the kitchen. The kitchen is positioned at the center of the home & features white shaker cabinetry, grey quartz countertops, a large island with a butcher block countertop, seating and storage on all sides, a vent hood over the range, stainless steel appliances & a large white ceramic single-bowl farmhouse sink with a pull-down commercial-style faucet, along with windows overlooking the pool & backyard. The home offers an ideal split-bedroom plan, with the primary suite located on the back left side of the home and added in 2018 by Winter Brothers Construction. The suite includes a spacious bedroom with recessed lighting, separate closets with built-in organization & a well-appointed bath with dual vanities, a freestanding soaking tub, a glass-enclosed walk-in shower with rain shower head & a private water closet. On the opposite side of the home are three additional bedrooms, including one with an en-suite bath designed with a pedestal sink, wall-mounted storage & a glass-enclosed walk-in shower, along with a full hall-entry bath which comes with a tub/shower combination & new vanity (2026). Highlights of the backyard include a paver deck, saltwater swimming pool with a generous shallow shelf, child safety fence, play set, raised garden bed, lawn space for people and pets and a mature peach tree that produces fresh peaches. The home also features an attached two-car garage with a laundry area, professional landscaping and a newly installed white privacy fence with gated access on both sides. In addition to its charm & interior updates, the home offers meaningful system improvements, including electrical panels (2018), two HVAC systems (2018 and 2022), a full re-pipe to PVC/CPVC, roof replacement (2017–2018) & an electric water heater (2018). The property owner has the option to join the Dommerich Estates Beach Civic Association, which provides access to a private boat ramp, picnic area and lakefront amenities on Lake Minnehaha. Residents also enjoy convenient access via the neighborhood boardwalk to Maitland Community Park, offering tennis and basketball courts, trails, pavilions and year-round activities. Zoned for Dommerich Elementary, Maitland Middle and Winter Park High and located just minutes to Park Avenue, Lake Lily, the Maitland SunRail station and major roadways, this is an opportunity to own a move-in ready home in a well-established neighborhood with strong school zoning, a true sense of community and lake access to the Winter Park Chain of Lakes.

150 Seneca Trail, Maitland

$799,900
3 Beds 2 Baths Druid Isle SubDv. 32751 Zip Code
Substantial price reduction for LAKESIDE LIVING in Maitland, Florida! LEASE OPTION CONSIDERED! Nestled canal front with direct access to Lake Charity, this vintage block home is built like a fortress with all the modern luxuries of today. A unique home for those who desire authenticity in both design and quality. A side entry garage leads to a courtyard like entrance with a marble path and asian influenced landscape. Double doors open into an expansive footprint with 3 large bedrooms, 2 baths and over 3,000 sq ft of living space. A 42 x 12 sunroom overlooking the water pays homage to the nostalgic Florida charm of this decade. No expense was spared when renovating this interior. Luxurious finishings and professional installation can make all the difference! Especially noted in the kitchen and baths! Upon entering, a Balsato Beige Porcelain fireplace surround wall anchors the space with plenty of areas to create conversational seating, a designer’s dream! The kitchen island is open to the entire living space with tons of storage and a double waterfall edge in Taj Mahal Quartzite. The perimeter counters are done in beautiful Bora Bora Quartz by Sharifstone. Real wood cabinetry in white dove compliments the earth tones giving a more transitional than modern vibe. Brushed gold hardware, lighting & plumbing fixtures are the perfect “jewelry” for the space! All new high end appliances convey. A brick fireplace graces the dining/living room wall (sounding like a song), yet another functional design opportunity to really create a home that works for YOU. There’s plenty of spots for an office, although not formally mentioned and the ability to use some of the square footage to create an additional “room” if needed. The primary suite closet takes the cake with all the fun features a dream closet should have! The ensuite bath has a lovely vanity with Quartz tops, dual sinks and a gorgeous shower with designer tile and a frameless glass door. Hardware is all in a matte black. The additional 2 bedrooms share a bath that has also had a complete remodel! This home is move in ready with a timeless style throughout. Flooring is a cohesive blend of tile and luxury vinyl plank. New roof 2024. With ideal proximity to fine dining & shopping in Maitland, Winter Park’s infamous Park Avenue and the Theme Parks, you’ll find yourself “staycationing” a little more often!

1501 Druid Isle Road, Maitland

$2,000,000
5 Beds 5 Baths Hollieanna Shores 1st Add SubDv. 32751 Zip Code
Under contract-accepting backup offers. Under Construction. A striking blend of refined luxury and sleek contemporary architecture, this exceptional new construction residence is set to be completed in July 2026. Designed for effortless living and elevated entertaining, the home showcases 5 well-proportioned bedrooms, 4.5 designer bathrooms, and approximately 3,695 square feet of thoughtfully curated interiors. From the moment you enter, you’ll experience a bright, open layout that flows seamlessly from one space to the next. At the heart of the home is a culinary-inspired kitchen, complete with premium appliances, custom cabinetry, quartz surfaces, and a generous island that invites gathering and conversation. The living and dining areas are ideal for hosting, framed by expansive windows that capture views of the outdoor retreat. The private primary suite feels like a personal spa, featuring a serene bath with dual vanities, a freestanding soaking tub, a walk-in shower, and a spacious wardrobe closet. Each additional bedroom offers comfort, style, and ample storage—perfect for family, guests, or a dedicated office. Outside, the property transforms into an outdoor sanctuary with a shimmering pool, a covered lanai designed for year-round enjoyment, and a fully equipped summer kitchen ready for unforgettable weekends. A rare opportunity to own a remarkable residence where modern design meets everyday livability—a home you’ll never want to leave.

103 Whitecaps Circle, Maitland

$649,000
3 Beds 2 Baths N/A SubDv. 32751 Zip Code
Virtually Staged. FINAL SUBMISSION WINDOW – SELLER HAS SET A FIRM DEADLINE TO SECURE CONTRACT. ALL PROPOSALS DUE MAY 11. FULLY RENOVATED Maitland home offered for a limited time only. Seller will review all submitted contracts, including those below list price, and is open to structuring terms that work - including potential closing cost assistance or rate buydown with acceptable terms. Contracts must be submitted by May 11. Seller will make a decision immediately thereafter. This property will be removed from the market if not sold by the deadline. MAJOR PRICE IMPROVEMENT Fully reimagined designer pool home with deeded access to skiable Lake Seminary, offering a rare blend of modern luxury, privacy, and prime Maitland location. Tucked away in a peaceful setting, this home lives like a private retreat while remaining just minutes from everything Maitland and Winter Park have to enjoy. At the heart of the home is a true showpiece kitchen, thoughtfully designed with a striking waterfall-edge island, full-height quartz backsplash, beverage fridge, and a clean, modern aesthetic reminiscent of a custom build. The open-concept layout is filled with natural light and flows effortlessly into the main living spaces—perfect for both elevated entertaining and everyday living. The primary suite delivers a spa-inspired retreat, featuring a freestanding soaking tub, oversized walk-in shower with dual heads, and carefully curated designer finishes that create a true sense of escape. Step outside to your own private backyard oasis, complete with a sparkling pool, expansive paver patio, and newly fenced yard—designed for both relaxation and hosting. The oversized lot offers exceptional flexibility, with ample space to add a garage, guest house, or additional storage to suit your needs. This home has been fully renovated with a strong emphasis on quality craftsmanship and high-end finishes throughout, including a new roof, HVAC, windows, flooring, and more—offering true move-in-ready peace of mind. Enjoy deeded access to skiable Lake Seminary via recorded easement—an exceptional and increasingly rare feature in this area. Buyer to verify access and use. Conveniently located near Maitland and Winter Park, with easy access to shopping, dining, and major roadways—giving you the perfect balance of privacy and accessibility.

106 Oakwood Drive, Maitland

$725,000
3 Beds 2 Baths Highland Park Ests SubDv. 32751 Zip Code
Virtually Staged. Set on one of the most sought-after streets in Dommerich, this completely renovated home combines the solid construction of a 1963 block home with thoughtful modern updates throughout. From the moment you arrive, the circular driveway, classic brick accents, and welcoming front porch set the tone. Inside, a bright foyer opens to beautiful solid maple wood floors and a light, airy feel that carries throughout the home. To the right, the formal living room features built-in shelving and a striking brick wood-burning fireplace, while the adjoining formal dining room connects directly to the kitchen and can be closed off with pocket doors if you want a little separation. The eat-in kitchen is truly the heart of the home, showcasing rich solid cherry cabinetry, unique man-made glass countertops, a large farmhouse sink, and top-of-the-line stainless Bosch appliances including a built-in oven and gas cooktop. A generous peninsula overlooks the oversized family room, where French doors open to a stunning Florida room that fills the home with natural light. This space is a showstopper—large, lined with windows, and finished with soaring shiplap ceilings—creating the kind of room you’ll use year-round, with direct access to the backyard. The primary suite is spacious and refined with crown molding, a built-in closet plus a walk-in, and a beautifully renovated bath featuring matching glass countertops, a Kohler vanity, and a glass shower with both a large rain head and handheld fixture. Two additional bedrooms are generously sized and share an updated hall bath with a large vanity, classic subway tile, and a soaking tub. The interior also includes a well-equipped laundry room with cabinetry, a cedar storage closet, and access to the two-car garage. Out back, the fully fenced private yard offers plenty of room for entertainment, recently re-sodded with irrigation and enclosed with a brand new wood fence installed in 2025—leaving ample space for a future pool or patio if desired. Additional upgrades include smooth flat ceilings with recessed lighting throughout, new drywall, plantation shutters, updated windows and doors, and an energy-efficient hybrid water heater. Beyond the home itself, the location is hard to beat—just a short walk to Dommerich Elementary, Maitland Middle School, and Maitland Community Park offering tennis courts, indoor racquetball, and playgrounds. Zoned for highly regarded Winter Park High School. Call today to schedule your private showing!

2040 Geronimo Trail, Maitland

$515,000
3 Beds 2 Baths Westminster SubDv. 32751 Zip Code
Beautifully renovated 3-bedroom, 2-bathroom home featuring modern finishes and a bright, open layout. Wood-look tile flows throughout the entire home, creating a cohesive and low-maintenance living space. The stunning white kitchen is the heart of the home, complete with quartz countertops, new appliances, recessed lighting, a large island, and stylish pendant lighting—perfect for cooking and entertaining. The open-concept great room and kitchen create an inviting and spacious feel ideal for gatherings. A split floor plan offers privacy, with two bedrooms located in the front right portion of the home along with a fully renovated guest bathroom featuring a new vanity, bright white tile, and a tub. Just off the kitchen, the sunroom is filled with natural light and provides access to the expansive backyard as well as the large primary suite. The primary bedroom retreat features double barn doors leading to a beautifully updated bathroom with a spacious walk-in shower with built-in seat and a walk-in closet with custom built-ins conveniently located within the bathroom. Step outside to enjoy the large patio area, perfect for outdoor entertaining, surrounded by mature trees that enhance the home’s charm and privacy. Additional updates include a new roof installed in 2023. Conveniently located near I-4 for easy commuting and close to numerous restaurants, grocery stores, and everyday conveniences, this move-in-ready home combines modern upgrades with a fantastic location.

830 Faith Street, Maitland

$500,000
4 Beds 3 Baths Northwood Heights SubDv. 32751 Zip Code
Virtually Staged. NEW ROOF 2022 - NEW AC 2022 - NEW ELECTRICAL PANELS 2022 - REPLUMB 2022 - NEW SEPTIC 2023 - Seperate detached GUEST HOUSE offering built-in monthly income potential. Previously rented under market value at $900/month, the guesthouse is currently vacant and ready for a new tenant, a private space for adult children, or a comfortable in-law suite. Endless possibilities to maximize value and flexibility! The spacious single-level layout features 3 bedrooms, 2 bathrooms in the main house, plus an updated guest suite. Enjoy an open living and dining area with a stone fireplace, designer lighting, and luxury vinyl plank flooring. The upgraded kitchen includes wood cabinets, granite countertops, penny tile backsplash, and new stainless appliances. A bright family room leads to two outdoor seating areas, including a brick courtyard with a second fireplace. The oversized primary suite and additional bedrooms feature new plush carpet, while the bathrooms have been fully updated. The detached guest suite offers 1 bedroom, 1 bath, a sitting area, and a wet bar. Additional features include a washer and dryer, security cameras, and a Google/Nest doorbell, all conveying with the home. Double carport, oversized driveway, and a private lot on a quiet street. Conveniently located near downtown Maitland with easy access to I-4.

140 E Faith Terrace, Maitland

$534,900
3 Beds 2 Baths Dommerich Woods Unit 2 SubDv. 32751 Zip Code
Dommerich Woods gem! Tucked away on a cul-de-sac street in one of Maitland’s most sought-after neighborhoods, this beautifully updated 3-bedroom, 2-bath block home is the one you’ve been waiting for. Move-in ready and genuinely charming from the moment you walk in. The open floor plan feels airy and welcoming, with vaulted ceilings and natural light pouring through every room. The living room centers around a classic brick fireplace that anchors the space perfectly, while the kitchen is a true standout-quartz countertops, stainless appliances, 40-inch soft-close shaker cabinets and a built-in pantry. The layout flows effortlessly between living, dining and family spaces, making it as functional as it is inviting. The split bedroom layout offers great privacy for everyone. The primary suite is a real retreat- vaulted ceiling, spacious walk-in closet and a completely redone en-suite bath with a lovely garden window. Both bathrooms have been given a fresh, modern look that feels clean and polished. The updates list is long and impressive: newer LVP flooring throughout, AC (2022), water heater (2023), roof replaced in 2016, replumbed in 2008, newer paint inside and out, newer light fixtures and ceiling fans. Laundry is indoors and connects right to the two-car garage-a detail you’ll appreciate daily. Out back, the expansive yard is a genuine sanctuary. Mature trees, lush landscaping and total privacy make it the kind of space you’ll actually use. A large shed with 50-amp power is ready for a workshop, hobby space or serious storage-and with NO HOA, bring the toys too! Just minutes from Kewannee Park, the Seminole bike trail and easy access to major roads and local shops and restaurants. It’s a rare find in a neighborhood where homeowners rarely leave. Come take a look.

1230 Hollyridge Trail, Maitland

$860,000
5 Beds 4 Baths Dommerich Hills Fifth Add SubDv. 32751 Zip Code
One or more photo(s) has been virtually staged. Welcome to 1135 Thunder Trail, a beautifully updated pool home in Maitland, Florida, located in the highly desirable Dommerich Hills neighborhood. Situated on an oversized lot with no HOA, this property offers nearly 3,000 square feet of flexible living space, combining comfort, functionality, and the best of Florida outdoor living. Step inside to an open and inviting floor plan featuring a formal living room and dining area that flow seamlessly into a spacious family room, perfect for everyday living and entertaining. The heart of the home is the fully upgraded gourmet kitchen, complete with high-end appliances, double ovens, large cooktop, stone countertops, custom cabinetry, oversized refrigerator, and a massive center island designed for gathering. The family room is warm and stylish with a fireplace, custom feature wall, and a built-in wine bar with beverage coolers, bar sink, and coffee station. Large windows fill the home with natural light and provide views of the private backyard oasis. The first-floor primary suite offers a true retreat with dual walk-in closets, French doors leading to the pool, and a renovated ensuite bathroom featuring double vanities and a walk-in shower. Upstairs, you’ll find an expansive bonus room (26x17) with a half bath and built-in daybed, ideal as a media room, game room, home office, or guest suite, plus three additional bedrooms, a full bath with dual sinks, and custom built-ins throughout. Step outside to your private backyard paradise, featuring a sparkling in-ground pool, outdoor shower, fire pit area, multiple gazebo seating spaces, mature landscaping, and fruit trees. The fully fenced yard offers privacy and plenty of space for pets or play, while built-in gas lines make outdoor cooking effortless. Recent upgrades include: * New roof (2022) * New windows (2021) * New doors (2025) * HVAC (2019) * Fresh interior paint & updated landscaping Additional features include a two-car garage, large indoor laundry room with cabinetry, irrigation well, city sewer, and abundant storage throughout. Located just minutes from Maitland Social, Maitland City Centre, shopping, dining, and parks—and zoned for top-rated schools including Dommerich Elementary School, Maitland Middle School, and Winter Park High School—this home offers the perfect combination of location, lifestyle, and value. If you’ve been searching for a move-in ready pool home in Maitland with no HOA and top schools, this is the one.

1135 Thunder Trail, Maitland

$700,000
3 Beds 2 Baths Dommerich/ Highland Park SubDv. 32751 Zip Code
Here is your chance to be in the coveted Dommerich neighborhood and have a move in ready 3/2 pool home! This home has been tastefully renovated to include newer front living room Anderson Windows and Sliding Doors. Newer kitchen countertops, NEW ROOF 2025, Second bath updated in 2017, HVAC 2015, Water Heater 2015. The Salt Cell for the pool 2025, Refrigerator and Dishwasher 2025 and updated LED lighting throughout. All your important insurance items taken care of! Now, let's talk about this home! This Mid-Century Modern is MOVE IN READY! You will absolutely love the natural light from the beautiful front windows. Your kitchen is aesthetically pleasing with a wonderful flow and makes entertaining a breeze! The walk in pantry is ideal for extra storage. The Primary Suite is spacious and offers an updated en-suite with a walk in shower. The secondary rooms are nice sized and provide ample natural light as well as garden views. You will spend the majority of your time in your luxurious pool and relaxing on the covered deck area. With several areas of dedicated lounge space and sheltered area from the sun, this backyard oasis is a rare find! All the while, still providing you plenty of greenspace for play and pets. This home is ideally situated to Dommerich Elementary and minutes to Maitland Middle as well as Zoned for Winter Park High School, you are the Trifecta of Schools! Minutes to Publix, Walmart, Target, downtown Winter Park and Maitland, the Sun Rail and to the I-4 Maitland Exchange. Don't miss your chance to see why so many live and love to call Dommerich HOME!

2040 Thunderbird Trail, Maitland

$415,000
2 Beds 1 Baths Lake Maitland Terrace Apts SubDv. 32751 Zip Code
Experience turn-key living at its best in this beautifully renovated, designer-owned, lakefront condo, conveniently located in the sought-after Lake Maitland Terrace community on the Winter Park Chain of Lakes. This stunning 2-bedroom, 1-bath residence was thoughtfully redesigned with high-end finishes and an open, modern layout that maximizes both style and functionality. FURNITURE IS NEGOTIABLE! The completely updated interior features luxury “wood-like” vinyl plank flooring throughout, for enhanced durability. Enjoy a stylish kitchen with custom cabinetry, quartz countertops, tile backsplash, and newer appliances, and a beautifully remodeled bath with marble herringbone tile and designer fixtures. Additional upgrades include all new electrical, recessed lighting with dimmers, updated plumbing, custom closets, shiplap accents, new interior doors and trim, high-end Emtek door knobs throughout, and sound-reducing flooring underlayment for added comfort. Lake Maitland Terrace offers a true lakefront lifestyle, with private access to Lake Maitland, the largest lake on the Winter Park Chain. Residents enjoy a community dock and fishing pier, kayak & paddleboard racks, a sparkling pool, a clubhouse with lake views, shuffleboard courts, bike storage, and convenient on-site laundry....but this unit has it's OWN Washer and Dryer! Ideally located near shopping, dining, theaters, and just minutes from Park Avenue in Winter Park, this fresh and modern move-in ready condo offers effortless living in one of Maitland’s most desirable waterfront communities. Don't forget.... the FURNITURE IS NEGOTIABLE!

1140 S Orlando Avenue Unit H-13, Maitland

$299,000
2 Beds 2 Baths Lake Maitland Terrace Apts SubDv. 32751 Zip Code
Under contract-accepting backup offers. Fresh price on this luxury condominium is in the established complex of Lake Maitland Terrace which sits on the shores of Lake Maitland, Winter Park Chain of Lakes. This immaculately maintained complex includes 11, 2-story, mid-century modern buildings sprawled across several acres, creating beautiful green space and picturesque views across the lake. This unit is special. A complete renovation with every detail accounted for, it is turnkey with enduring design. Warm wood floors are carried through spaces, kitchen has been opened to living room and flanked with windows allowing natural light to shine. Kitchen features white 42-inch shaker style cabinetry, quartz counters, subway tile backsplash, open shelving and stainless appliances. Counter seating is inviting and creates great kitchen function with loads of counter space for the aspiring chef. Primary suite is spacious with large closet storage, and renovated bath. Secondary bedroom and additional bath add to the flexibility of the unit, a guest room or home office. Indoor laundry makes this lock-and-go lifestyle even more appealing. Custom window treatments, closet system storage, updated HVAC, and fresh paint throughout. The location is pristine with walkability to the Enzian independent theatre, Lake Lily Park with a recreational trail and park, and home to community events, many restaurants and more. A short distance to Winter Park Village and Park Avenue and zoned for incredible schools with Dommerich Elementary, Maitland Middle & Winter Park Highschool. Complex is amenity-rich with sidewalks, community pool, generous dock, shuffleboards and more. Make this rare opportunity yours to own a little slice of this Maitland treasure.

1140 S Orlando Avenue Unit F11, Maitland

$535,000
3 Beds 3 Baths Northgate SubDv. 32751 Zip Code
***UNDER CONTRACT - ACCEPTING BACKUP OFFERS*** Welcome to this stunning 3-bedroom home offering modern upgrades, thoughtful design, and exceptional indoor-outdoor living.Extensively remodeled in 2021, the interior of this home was thoughtfully updated to create a modern and inviting space. The highly desirable open floor plan seamlessly connects the kitchen and living room—perfect for hosting gatherings and enjoying everyday life with ease. Major system updates include a new roof (2023), new AC unit (2023), and ductwork balancing completed in 2025 for improved airflow and comfort. The home also features energy-efficient double pane windows for added comfort and efficiency year-round. Crown molding throughout adds an elegant touch, while the interior was freshly painted in 2023. This home is fully smart-home capable, allowing you to control nearly all lighting and the AC with your voice or through the wall-mounted tablet.The kitchen is equipped with amazing features for any home chef such as a gas range, prep sink and new app-controlled smart appliances installed in 2023. There is an abundance of cabinet storage and countertop space, providing plenty of room for entertaining and everyday organization.The spacious primary suite is thoughtfully separated from the additional bedrooms, offering privacy and a peaceful retreat. The luxurious primary bathroom features dual shower heads, a freestanding soaking tub, and a generous walk-in closet—creating a true spa-like experience at home.Two spare bedrooms feature brand-new carpet (2025), and a dedicated den provides the perfect space for a home office, study, or flex room to fit your needs.Enjoy a spacious yard with plenty of room for pets, complete with a pool (2019), a cozy wood-burning fire pit, a shed, and a patio area with propane hookups ready for your grill.With extensive updates, smart-home features, and exceptional outdoor living space, this home is ready to impress. Schedule your showing today!

1531 Glastonberry Road, Maitland

$504,000
2 Beds 2 Baths Moorings On Lake Maitland Condo Bldg 03 SubDv. 32751 Zip Code
LAKEFRONT PARADISE ON LAKE MAITLAND AND THE WINTER PARK CHAIN OF LAKES. Cue the Jimmy Buffett music as you arrive home to your own serene tropical lakefront paradise here at The Moorings on Lake Maitland. The pace feels a bit more relaxed here on the water! This beautiful, move-in ready FULL lakefront condo is located on the third floor of building 3 which is closest to the water. Imagine every day feeling like a tropical vacation in this coveted community with no outside maintenance for you to tend to. Step onto the elevator and effortlessly arrive at your front door. Step inside to find breathtaking panoramic views of sparkling Lake Maitland through oversized glass doors leading to your own private balcony. Enjoy lake views from every single room, even from both bathtubs! Start your mornings with quiet reflections on your peaceful balcony with the soothing sounds of nature and the lake waters gently lapping on the shoreline. Wind down your evenings visiting with friends on the community lawn or expansive dock under painted skies with cool lake breezes. Launch a kayak from the community dock and explore the wonders and natural beauty found throughout the coveted Chain of Lakes. Have your own boat? Newly renovated Fort Maitland Park is next door with day parking and a convenient boat launch. And from time to time, it’s possible that a private boat slip at The Moorings could come available for private purchase or lease. The spacious interior of this condo offers a pleasing neutral color palette with luxury vinyl wood flooring in the living area and primary suite. Attractive oversized tile graces the foyer, kitchen, dining alcove, bathrooms, and balcony. The current décor leans into a vintage Florida tropical vibe allowing you to easily envision the vacation-every-day-feeling! The spacious foyer includes a walk-in storage closet. The well-appointed kitchen is outfitted with custom wood cabinetry, gorgeous granite counters, stainless appliances, a closet pantry in the hall, and glorious water views from the large pass-through opening with breakfast bar. Dine with friends surrounded by water views from the dinette, from the main dining area (currently used as additional living area), or from your balcony. No worries about lugging laundry to a community space--enjoy a double door laundry closet. The combo living dining area is currently set up as all living space providing wonderful entertaining and lounging opportunities. Wake up every morning to serene water views in this private primary suite with double windows for unobstructed views and French door access to the balcony. The beautiful en-suite has a granite dual sink vanity, walk-in closet, and a garden soaking tub and shower with water views as well! Imagine the relaxing baths you could have here! BR two has cozy carpet and a double door closet with easy access to the hall bath with granite sink vanity and a tub/shower. This is a tranquil community with abundant privacy, but opportunities abound for connection if you’d like. The clubhouse has regular gatherings and events, and the recently refurbished pool and spa are ideal for total relaxation or for connecting with friends. Popular restaurants such as Luke’s, Antonio’s, and Athena’s are found just outside the community and a stone’s throw will land you at Enzian Theater with Eden Bar, the Maitland Art Center, all of the wonderful cultural venues and retail establishments of Winter Park and Orlando, and so much more. Welcome home!

206 Quayside Circle Unit 302, Maitland

$850,000
4 Beds 2 Baths Maitland Grove SubDv. 32751 Zip Code
Welcome to 351 White Oak Drive in Maitland, a beautifully reimagined residence where modern elegance meets everyday comfort. This completely renovated 4-bedroom, 2-bath home is essentially brand new, showcasing refined finishes and thoughtful upgrades throughout. The heart of the home is a gourmet kitchen designed to impress, featuring sleek cabinetry, premium surfaces, and an open layout perfect for entertaining and daily living. The spa-like primary bathroom offers a serene retreat with luxurious finishes that evoke a high-end resort experience. Enjoy seamless indoor-outdoor living with a private pool that has been completely done including new tile and new pool equipment , ideal for relaxing weekends or hosting guests. Generously sized bedrooms, updated baths, and a functional floor plan provide comfort, style, and flexibility for families or professionals alike. This home has been completely redone with elegance and quality in mind—delivering the look, feel, with everything feeling new and fresh in an established Maitland neighborhood. Move-in ready and truly turn-key, this is a rare opportunity to own a fully updated home with timeless appeal. Roofs updated in 2022 and 2021, updated Electrical and Plumbing. One of a kind set appointment for viewing before it gone!

351 White Oak Circle, Maitland

$599,900
4 Beds 3 Baths Stonewood SubDv. 32751 Zip Code
Virtually Staged. Short Sale. Welcome to this beautifully maintained 4-bedroom, 3-bathroom pool home offering the perfect blend of space, style, and location! From the moment you walk in, you’ll love the open layout and rich hardwood floors that create a warm and inviting atmosphere throughout. Designed for both everyday living and entertaining, this home features a dedicated office plus separate living, dining, and family rooms—giving everyone their own space while still feeling connected. The updated fireplace serves as a stunning focal point in the main living area, enhanced by natural light pouring in through the skylights. Recent upgrades provide added peace of mind and value, including a paver driveway and new gutters installed in 2019, full home re-pipe in 2021, air ducts sealed and new insulation added in 2021, a new pool pump and new AC compressor (one unit) in 2022, and new bedroom flooring in 2023.The kitchen is a true standout with 42” cabinetry, granite countertops, and newer stainless steel appliances, all overlooking the main living areas for seamless entertaining. A built-in wet bar adds the perfect touch for hosting gatherings and holiday celebrations. Retreat to the spacious primary suite and enjoy large closets throughout the home, providing ample storage for every lifestyle. Step outside to your private backyard oasis featuring a sparkling pool and expansive deck—ideal for relaxing weekends, outdoor dining, and Florida sunshine year-round. Located with easy access to Uptown Altamonte, I-4, 436, and Maitland Boulevard, this home places you just minutes from Lake Lily, Winter Park Village, Downtown Winter Park, and Cranes Roost—offering endless options for dining, shopping, parks, and entertainment. This home truly checks every box—space, updates, location, and a pool to top it all off! ????

448 Stonewood Lane, Maitland

$448,500
2 Beds 2 Baths Moorings On Lake Maitland Condo SubDv. 32751 Zip Code
Seller to pay up to one year of HOA! Wake up to shimmering lake views and unwind each evening with breathtaking Florida sunsets in this beautifully refreshed 2-bedroom, 2-bathroom condo. From the moment you step off the elevator, you’re welcomed into a light-filled, open-concept living space highlighted by oversized glass sliding doors that lead to a private enclosed patio—seamlessly blending indoor and outdoor living. The kitchen is both bright and inviting, featuring upgraded cabinetry, a spacious eat-in area, and a large island designed for effortless entertaining. Thoughtful updates throughout include upgraded flooring, brand-new carpet installed just six months ago, and a newer AC unit replaced two years ago for added comfort and peace of mind. Custom-tailored curtains complete the space with a refined, polished finish. cThe primary suite offers a quiet, private retreat with its own bath, while the split-bedroom layout ensures comfort and privacy for guests. Life at The Moorings is centered around a relaxed, lakeside lifestyle—complete with a community pool, heated spa, clubhouse, lushly landscaped grounds, and direct access to Lake Maitland on the Winter Park Chain of Lakes. Spend your days on the lakefront dock or hosting poolside gatherings, then enjoy the convenience of walking to local favorites like Luke’s and Antonio’s or exploring Maitland’s newly designed downtown with green spaces, farmers markets, and vibrant community events.

204 Quayside Circle Unit 504, Maitland

$647,000
3 Beds 2 Baths Dommerich Hills First Add SubDv. 32751 Zip Code
WELCOME TO YOUR DOMMERICH HOME - This tastefully updated Mid Century ranch is perfectly positioned on a gentle rise above the tree lined streets of Dommerich, offering both charm and modern functionality. As you enter the foyer, you are immediately welcomed by the clean lines and modern touches of the decor. The imported Italian tile and Terrazzo floors flow throughout this open floor plan and its' volume ceilings. The Curava countertops and subway tile backsplash perfectly frame the deep stainless sink and the crisp white cabinets in the bright eat-in kitchen. Just beyond the breakfast bar, the space opens to a generous dining room anchored by a striking fireplace - perfect for everyday meals or entertaining. Multiple living spaces provide incredible versatility, including a spacious family room, a cozy den ideal for relaxing or reading, and a bright Florida room that overlooks the backyard. These areas offer flexible options for work, play, or additional entertaining space. The primary suite offers a comfortable retreat with an en-suite bathroom and walk-in closet, while the additional bedrooms are well-sized and filled with natural light. Both bathrooms have been thoughtfully remodeled with a clean, modern design. Step outside to your shady private backyard where a brick paver terrace and mature trees create the perfect setting for outdoor living, dining, and relaxation. Recent upgrades include: all new LED light fixtures throughout, Energy Star double-pane windows and doors(214), new A/C system (2020), new water heater (2023), new gutters (2026), New Vinyl Fence (2019), Designer remodel in both bathrooms (2017), along with the recent public sewer connection—providing peace of mind for years to come. Located in the highly desirable Dommerich school district and convenient to shopping, dining, and major roadways, this move-in ready home combines classic style, modern updates, and an exceptional location. Don’t miss your opportunity to make this Dommerich home your own—schedule your private showing today.

1000 Kewannee Trail, Maitland

$1,000,000
5 Beds 4 Baths Maitland Club SubDv. 32751 Zip Code
Discover this beautifully staged expansive Florida residence offering timeless architecture and more than 3,500 square feet of thoughtfully designed living space. This exceptional 5-bedroom, 4-bath POOL home includes a spacious 3-car garage and is perfectly positioned on over a third-acre cul-de-sac lot. Designed for both comfort and flexibility, the 1st floor contains the primary bdrm, 3 additional bdrms plus kitchen, family room, formal living room and dining room. Upstairs features a private in-law, teen or guest suite complete with its own bonus/sitting room, bedroom, and full bath—an ideal private retreat for extended family or visitors. The split floor plan provides privacy for everyone, while the expansive living areas create a warm and inviting atmosphere for gathering and entertaining. The newer open kitchen flows seamlessly into the family room, making it the heart of the home. Downstairs, you’ll also find a dedicated home office, as well as an exercise room and full bath, perfect for an active lifestyle. Major updates include HVAC systems replaced in 2015 and 2016, and the entire home was fully replumbed in 2026 for added peace of mind. Enjoy Florida living at its best with your oversized private pool/spa and generous lanai and outdoor space. (Pool heater and pool light are being sold as-is.) This elegant home combines classic charm, thoughtful updates, and incredible space—ready to welcome its next owner. The Maitland Club is a 24 hour upscale guard gated community- Only 10 minutes to Winter Park, Whole Foods, Trader Joe’s, the Altamonte mall and easy access to I-4.

984 Brightwater Circle, Maitland

$529,500
4 Beds 2 Baths Greenwood Gardens Sec 01 SubDv. 32751 Zip Code
Welcome to one of Maitland’s most unique and captivating pool homes — perfectly positioned just steps from downtown Maitland and Lake Lily Park. This stunning 4-bedroom, 2-bath residence combines architectural character with everyday livability. Soaring vaulted ceilings and expansive windows flood the home with natural light, creating a sun-drenched family room that feels both grand and inviting. The open layout flows effortlessly, ideal for entertaining or relaxed Florida living. Step outside and you’ll discover a true backyard oasis. Surrounded by lush, mature Florida foliage, the oversized pool becomes your private retreat. A dramatic grotto-style waterfall spa adds resort-level ambiance — the kind of feature guests won’t stop talking about..... Condition? New Roof 2024, New A/C condenser and compressor 2025, Tankless Gas Hot Water heater, New Electrical panel, 2022. Pool was added in 2006 - inspected & verified in good condition Dec. 2025.... Location? It doesn’t get better. Enjoy walking distance to: • Downtown Maitland • Lake Lily Park • Maitland Public Library • The Maitland Bike Path • Maitland Center SunRail Station • Parks, schools, and local favorites • And yes — Whole Foods and Trader joes are just down the street. This is more than a home — it’s a lifestyle property in one of Central Florida’s most charming communities.

721 Gamewell Avenue, Maitland