Location: Maitland
Do Not Show Listings
2130 DELORAINE TRL, MAITLAND, FL 32751
$829,00018 Days on yellowkey MLS ID: O6397018
REDUCED by $21,000 (2.5%) on 04/21/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2175 Built: 1964 Tax: $10,394 (2025)Community: Highland Park Estates First AddSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$10,394
Elementary School: Dommerich Elem
High School: Winter Park High
Tax Year: 2025
Middle School: Maitland Middle
Remarks: Welcome to this beautifully renovated pool home in the highly sought-after Dommerich neighborhood of Maitland. Offering over 2,000 square feet of living space, this 3-bedroom, 2-bath residence perfectly blends modern upgrades with comfortable, functional living. Inside the home is designed for both everyday living and entertaining. The spacious living room serves as the heart of the home, featuring a stunning marble fireplace and seamless flow into multiple gathering areas, including a dedicated dining space just off the kitchen, a family room that leads to the outside and access to the bedrooms. The fully renovated chef’s kitchen is a true standout, showcasing soft-gray shaker cabinetry, quartz countertops, a Carrera marble backsplash, and stainless steel appliances. With ample counter space and a built-in water filtration system, this kitchen is as functional as it is beautiful. Throughout the home, you’ll find upgraded Italian wood-plank porcelain tile flooring, offering both durability and elegance. The primary suite provides a peaceful retreat with a walk-in closet and a fully updated ensuite bathroom featuring a double-sink vanity, granite countertops, and a spacious walk-in shower with marble and porcelain finishes. Step outside into your private backyard oasis. Designed for true Florida living, this space features a Pebble Tec pool, paver deck, covered gazebo with ceiling fan, a 65” outdoor TV, and a premium sound system perfect for entertaining or relaxing year-round. The lush landscaping, grassy area, and additional storage shed complete the outdoor experience. Additional highlights include a new roof (2019), A/C system (2021), WiFi-enabled irrigation system, fresh interior paint, and new LG washer, dryer, and dishwasher. Located in the desirable Dommerich area, just minutes from top-rated schools, dining, shopping, and major roadways, this home offers the perfect combination of location, upgrades, and lifestyle. This is the one you’ve been waiting for.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Mario Zendeli (407-325-3893)
1001 VERSAILLES CT, MAITLAND, FL 32751
$1,050,000Listed 04/25/2026 9:01AM MLS ID: O6401795
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3625 Built: 1981Monthly Fee: $29 Tax: $6,161 (2025)Community: VersaillesSingle Family
Taxes:$6,161
Elementary School: Lake Sybelia Elem
Remarks: One or more photo(s) has been virtually staged. Nestled within the quiet, established community of Versailles, this exceptional residence invites you to slow down and savor the good life. Offering over 3,600 sq. ft., this home features 4 spacious bedrooms and 3 full baths, with a layout that is both functional and flexible. The PRIMARY SUITE is conveniently located on the MAIN FLOOR and features an EXPANSIVE ATTACHED OFFICE, CRAFT ROOM OR SITTING ROOM—perfect for today’s lifestyle. This generous space also presents a unique opportunity for reconfiguration, allowing you to expand the primary bedroom and/or create a truly luxurious bath retreat tailored to your vision. Upstairs, three additional BEDROOMS ARE IMPRESSIVELY SIZED, offering plenty of room for family or guests. A STANDOUT FEATURE of the home is the BONUS ROOM with its own private entrance, located just off the rear garage—ideal for a game room, media lounge, or entertainment hub complete with space for a pool table, ping pong table, and a large-screen TV. At the heart of the home, the EXPANSIVE 23 x14 kitchen is filled with potential and already equipped with premium appliances, including a SubZero refrigerator, separate SubZero freezer, and a Viking cooktop. Built-in desk space and charming banquet seating create a welcoming spot for casual dining and everyday moments. The inviting family room is designed for cozy evenings, featuring a wood-burning fireplace, beverage fridge, ice maker, and sink—perfect for entertaining or unwinding. For larger gatherings, the expansive living room and adjacent dining area provide an elegant backdrop, whether hosting dinner parties, game nights, or enjoying music by a grand piano. Step outside to your private oasis, set on NEARLY HALF ON AN ACRE of beautifully landscaped grounds. The generous deck surrounds a stunning 10-foot-deep SWIMMING POOL offering endless possibilities for outdoor entertaining, relaxation, and recreation. Life in Versailles extends beyond your front door. HOA Residents can enjoy PRIVATE ACCESS TO LAKE Minnehaha, complete with a dock—perfect for paddleboarding, kayaking, or soaking in breathtaking sunset views. Just beyond the back gate, Maitland Community Park offers an array of AMENITIES including playgrounds, tennis courts, basketball, racquetball, and scenic fitness trails. A convenient paved path even connects you to nearby shopping and dining, including Publix. Ideally located with easy access to Maitland Boulevard, SR 414, I-4, and 436, SUNRAIL station is close and ZONED IN TOP RATED SCHOOLS, this home offers both tranquility and convenience. With an optional HOA, you have the freedom to enjoy the community on your terms. This is more than a home—it’s a lifestyle waiting to be embraced. Make your appointment today to view this lovely home!
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Heather Frazee (321-689-9465)
790 S LAKE SYBELIA DR, MAITLAND, FL 32751
$975,00052 Days on yellowkey MLS ID: G5108209
REDUCED by $20,000 (2.0%) on 04/08/2026
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 2021 Built: 1958 Tax: $6,881 (2025)Community: Acreage & UnrecSingle Family
Taxes:$6,881
High School: Edgewater High
Remarks: One or more photo(s) has been virtually staged. Rare opportunity to own a private 0.66-acre Estate homesite in Maitland with deeded Lake Sybelia access. 790 S Lake Sybelia Drive offers a unique combination of land, privacy, and lake rights in one of Maitland’s most desirable communities. Set on a secluded, no-HOA .66 acre's of land, the property includes 12 feet of lake frontage extending approximately 268 feet into Lake Sybelia, providing true and usable access. Private lake access you can actually use — without the $2M price tag. The updated home features 3 bedrooms and 2.5 bathrooms, a warm living room with a wood-burning fireplace, a panoramic window seat, and a spacious Florida room. Move in and enjoy as-is, or take advantage of the property’s full potential. This property is ideal for expansion, a second-story addition, pool, guest house, or a custom new build, offering flexibility rarely found in Maitland. The 0.66-acre lot is fully fenced with mature landscaping and provides ample space for outdoor living, entertaining, storing your RV or Boat. Opportunities combining large land for privacy and Lake Sybelia access are increasingly rare. Recent updates include: Roof (2019), AC (2023), insulation (2025), and updated electrical and plumbing. Ideally located near Lake Sybelia Park, the Iconic Enzian Theater, Maitland Art & History Center, Lake Lily Park, and just minutes to Winter Park and Downtown Orlando. Enjoy paddleboarding at sunrise or relaxing in your private backyard retreat — this property delivers a rare blend of space, privacy, and lake access in the heart of Maitland.
Listing is courtesy of: LISA REALTY PARTNERS (407-500-5472)
Listing Agent: Lisa Pownall (407-927-1698)
1241 MANCHESTER RD, MAITLAND, FL 32751
$625,00025 Days on yellowkey MLS ID: S5146896
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2038 Built: 1963 Tax: $4,268 (2024)Community: English Estates Unit 2Single Family
Taxes:$4,268
Elementary School: English Estates Elementary
High School: Lake Howell High
Tax Year: 2024
Middle School: South Seminole Middle
Remarks: Step into this beautifully renovated 4-bedroom, 2-bathroom home located in the heart of Maitland, where space, comfort, and modern design come together effortlessly. From the moment you walk in, you’ll notice the bright open-concept layout that creates a warm and inviting atmosphere, perfect for both everyday living and unforgettable family moments. The seamless flow between the living, dining, and kitchen areas makes this home ideal for gatherings, entertaining, or simply enjoying time at home. Natural light fills the space, enhancing every detail and making each room feel open, airy, and welcoming. Each bedroom offers comfort and versatility, whether you need space for a growing family, a home office, or guest accommodations. The thoughtful updates throughout the home provide a true move-in ready experience. As part of the renovations, the seller has a new roof scheduled, adding even more value for the future owner. Enjoy the charm and convenience of living in Maitland, with easy access to shopping, dining, parks, and major roadways. This is more than just a house—it’s a place where everyday life feels a little more special.
Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)
Listing Agent: Ricardo Araque (305-922-3413)
987 BRIGHTWATER CIR, MAITLAND, FL 32751
$1,100,0001 Day on yellowkey MLS ID: O6401747
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3270 Built: 1996Monthly Fee: $395 Tax: $12,450 (2025)Community: Maitland Club RepSpa: YesSingle Family
Taxes:$12,450
Remarks: Set on a generous one-third acre lot, the property offers ample room for outdoor enjoyment, from a potential playground to a thoughtfully designed lanai with dedicated areas for dining and lounging. Every corner of this home invites you to linger and enjoy. Ideally located near everything you love, this home offers easy access to premier grocery destinations, vibrant shopping and dining, major roadways, perfectly blending luxury with everyday convenience. Just minutes from Whole Foods, Trader Joe’s, Altamonte Mall, and the renowned shops and restaurants along Park Avenue in Winter Park, you’ll enjoy the best of Central Florida living right at your doorstep. Well-maintained home with A/C replaced in 2017. Interior upgrades completed in 2020, including a renovated kitchen, updated appliances, new flooring, and three beautifully updated bathrooms. No pool heater. Homes of this caliber do not last long.... come experience it for yourself.
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Gale Milgrim (407-443-9832)
1170 WILLOWBROOK TRL, MAITLAND, FL 32751
$759,00017 Days on yellowkey MLS ID: O6396754
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2159 Built: 1966 Tax: $4,455 (2025)Community: Maitland WoodsSpa: NoSingle Family
Taxes:$4,455
Remarks: Towering oaks and Spanish moss flowing in the breeze set the stage for this oasis in the heart of Maitland. This charming 4 bedroom, 2 bath abode with a tropical courtyard pool has been lovingly updated with luxe finishes and features. Step inside the covered airy breezeway where travertine pavers surround the screen enclosed pool deck and the true front door entrance. Beautiful crown moulding and wood-look ceramic tile flooring runs throughout the house (no carpeting). Double pane windows and sliders with build-in blinds accent the courtyard views. Arched doorways open to the poolside family room with wood-burning marble-surround fireplace and custom built-ins. Large enough for all your family and friends, the spacious living and dining rooms with custom window shutters and recessed lighting is sure to impress. Total kitchen remodel features handmade subway tile backsplash, quartz countertops, stainless steel appliances, and the most charming in-kitchen dining area with views out to the pool. A renovated full hall bathroom with double sink quartz vanity and tub/shower combo opens to the pool and is close to the 3 guest bedrooms (one bedroom also has sliders to the pool). Your large primary suite is tucked away at the back of the house with dressing area, walk-in closet, and separate toilet/shower room. And the views to the pool through the double sliders are inspiring. Indoor/outdoor living is a breeze in this unique Maitland courtyard style pool home. Plus, a fully fenced backyard is still big enough for children and pets to play. You’ll love the location with easy access to I-4, the shops and restaurants of Downtown Maitland and Lake Lily (home of a weekly farmer’s market), and walking distance to Lake Sybelia and lakefront Homer Hough Park. Improvements include NEW hot water heater 2026; NEW solar pool heater 2022; NEW paver driveway and motor court 2022; NEW roof 2021; NEW travertine pool deck 2021; NEW HVAC 2020; NEW Gernerac house generator; and Replumb CPVC 2015.
Listing Agent: Steven Ritz (321-277-8271)
2809 WAUMPI TRL, MAITLAND, FL 32751
$745,0009 Days on yellowkey MLS ID: O6399820
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2330 Built: 1971 Tax: $6,426 (2024)Community: Dommerich Hills 6Th AddSpa: NoSingle Family
Taxes:$6,426
Remarks: Completely Remodeled 2026 | Single-Story | Split Floorplan | The redesigned kitchen features 42" shaker cabinetry, Calcutta quartz countertops, a marble backsplash, and new stainless steel Fisher & Paykel appliances. Bathrooms have been completely remodeled with updated finishes. Luxury vinyl flooring extends through all common areas, complemented by LED recessed lighting and updated fixtures throughout. The open layout provides clear sight-lines between the kitchen and family room, creating a connected main living area. The pavers meet manicured lawns and fresh landscaping for a clean, contemporary finish that is 100% move-in ready. Additional features include an interior laundry room and a fully fenced backyard with a pool. Enjoy being just minutes from Park Avenue, Lake Lily, and Maitland City Centre where you'll find farmers markets, local dining, and boutique shopping. With easy access to I-4, 417, and the Maitland Exchange, you're well connected to everything Central Florida has to offer.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Farhad Haniff (516-587-2799)
1421 SUNNYSIDE DR, MAITLAND, FL 32751
$999,999155 Days on yellowkey MLS ID: O6358123
REDUCED by $100,001 (9.1%) on 04/24/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2116 Built: 1966 Tax: $5,513 (2024)Community: Maitland Park SouthSingle Family
Taxes:$5,513
Remarks: One or more photo(s) has been virtually staged. Priced below appraised value for a limited opportunity to capture instant equity. Welcome to 1421 Sunnyside Drive, Maitland, FL, a beautifully maintained 4-bedroom, 2.5-bath single-family home with a pool, located on a corner lot directly adjacent to Winter Park. While this home carries a Maitland address, it sits just steps from Winter Park homes, offering the best of both locations. This move-in-ready residence features thoughtfully designed indoor and outdoor living spaces and is zoned for the top-rated Dommerich Elementary School. From the moment you arrive, manicured landscaping and an inviting covered front porch create a warm first impression. Inside, natural light fills the home through skylights and bay windows, highlighting hardwood floors and a wood-burning fireplace. The open layout provides a seamless flow between living spaces, ideal for everyday living and entertaining. The chef’s kitchen serves as the heart of the home and features custom hardwood cabinetry, granite countertops, stainless steel appliances, a wine chiller, and a spacious breakfast island with ample seating. The kitchen opens to the main living areas, creating a functional and welcoming space. The primary suite offers a private retreat with wood floors and French doors leading directly to the porch. The ensuite bathroom includes an oversized shower with spa-style jets and customized storage. Three additional bedrooms and a full bathroom are located down a terrazzo-finished hallway and include custom upgrades. The dining area captures beautiful morning light through the bay window, while the living room features French doors that open to the outdoor living space. The private backyard oasis is designed for year-round enjoyment and includes a heated pool enclosed by a full screened deck and patio, creating a true indoor-outdoor lifestyle. Additional features include a custom built-in home office with abundant storage, a freshly refinished two-car garage, and an oversized driveway with a 30-amp electrical hookup for an RV or boat. The home has been freshly painted inside and out, includes new carpet, and reflects quality craftsmanship throughout. Enjoy quick access to Winter Park’s shops, dining, parks, and cultural offerings, along with the conveniences of Maitland living, making this home an exceptional opportunity in a highly desirable Central Florida location.
Listing is courtesy of: STRICKLAND REALTY GROUP INC (407-448-5068)
Listing Agent: Amanda Binns (407-448-5068)
921 N THISTLE LN, MAITLAND, FL 32751
$1,049,0008 Days on yellowkey MLS ID: R4911080
REDUCED by $51,000 (4.6%) on 04/22/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2300 Built: 1967 Tax: $4,489 (2025)Community: Highland Park EstatesSpa: YesSingle Family
Taxes:$4,489
Remarks: Central location, fully renovated, A-rated schools, a resort-style pool - this Dommerich home checks every box - and it is move-in ready, turnkey for your lifestyle. Situated in one of Central Florida’s most sought-after neighborhoods for over 60 years, Dommerich is known for its top-rated schools, tree-lined streets, parks, and unmatched convenience. This home sits right in the heart of it all. Originally built in 1967 and thoughtfully reimagined in a top-to-bottom renovation completed in 2019, the property blends classic charm with modern design and systems. Major updates include roof, HVAC, plumbing, electrical, windows, doors, insulation, appliances, kitchen, primary wing addition, natural gas connection, and a Rinnai tankless water heater. Inside, the open-concept living and dining spaces flow seamlessly to a designer pool and screened patio, creating an ideal indoor-outdoor lifestyle. The modern kitchen features extensive cabinetry with drawer-based storage, a coffee bar, and easy access to the garage and main living areas. A standout feature is the 2019-built primary suite addition, offering vaulted ceilings, a custom walk-in closet, en-suite bath, laundry, utility closet, and direct access to the pool area. The home also includes a second primary bedroom with its own en-suite bath that doubles as a pool bath, plus two additional bedrooms and a shared hall bath. The curb appeal is anchored by a mature, storybook-style shade tree, setting the tone for the character found throughout the property. Enjoy a short walk to the schools on a secluded sidewalk or take in the open sports fields across the street and Maitland Community park a few streets over.
Listing is courtesy of: VISTA NATIONAL MANAGEMENT INC (407-252-5052)
Listing Agent: Garrett Mcginnis (321-278-9511)
781 GOLDWATER CT, MAITLAND, FL 32751
$860,00065 Days on yellowkey MLS ID: O6383680
0 Days Off yellowkey (back on 4/23/2026)
REDUCED by $25,000 (2.8%) on 04/14/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2550 Built: 1970 Tax: $5,042 (2025)Community: Maitland Highlands DommerichSingle Family
Taxes:$5,042
Remarks: Under contract-accepting backup offers. Rare Dommerich Opportunity - 5 Bedrooms | 3 Baths + Office with a Pool on an Oversized Lot! Finding a true 5-bedroom, 3-bath home with a dedicated office in Dommerich is incredibly rare—and this one delivers, beautifully. Tucked away on a quiet cul-de-sac and set on over 1/3 acre, 781 Goldwater Ct offers space, privacy, and a lifestyle that’s hard to match. From the moment you arrive, the home’s charm stands out—featuring a welcoming front courtyard perfect for morning coffee or a peaceful garden retreat. Inside, a flexible and functional layout is designed for both everyday living and entertaining. Formal living and dining rooms pair seamlessly with a warm, inviting family room complete with a fireplace and built-ins. The kitchen is both stylish and practical, with granite countertops, stainless steel appliances, bar seating, and a sunny breakfast nook—all opening to the main living areas. Durable wood-look tile flows throughout for easy maintenance and modern appeal. The split-bedroom floor plan provides ideal privacy, with a spacious primary suite in its own wing featuring a renovated bath, dual sinks, and a large walk-in closet. On the opposite side, four generously sized secondary bedrooms include extra storage (two with walk-in closets!) and beautifully updated bathrooms—including a convenient pool bath. Step outside to enjoy true Florida living: a sparkling 20,000+ gallon pool surrounded by an expansive paver deck, offering plenty of room to entertain or unwind. A separate green space adds flexibility for play or pets, while maintaining a low-maintenance yard. An added surprise - this extra-large homesite and unique street allows for a rear entry garage. Not only does that add charm and curb appeal to the front of the home, but if you are a car lover or just need extra parking space, this is the home for you! The lengthy driveway and oversized garage can accommodate multiple vehicles or even a boat! Additional highlights include abundant storage, indoor laundry, enhanced insulation, and major system updates: Roof (2023), AC (2021), PEX replumb, sewer connection (no assessment), and fresh exterior paint. No HOA or community fees! Located just steps from Dommerich Elementary and Maitland Middle, with easy access to parks, dining, Park Avenue, and I-4—this is location and lifestyle in one. Plus, this home is zoned for Winter Park High School! Opportunities like this in Dommerich don’t come often—this is one worth seeing today!
Listing Agent: Erin Baker (407-719-0030)
140 E FAITH TER, MAITLAND, FL 32751
$525,00044 Days on yellowkey MLS ID: V4947849
0 Days Off yellowkey (back on 4/24/2026)
REDUCED by $15,000 (2.8%) on 04/22/2026
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2748 Built: 1956 Tax: $5,451 (2024)Community: Northwood HeightsSingle Family
Taxes:$5,451
Elementary School: Lake Orienta Elementary
High School: Lyman High
Middle School: Milwee Middle
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. NEW ROOF 2022 - NEW AC 2022 - NEW ELECTRICAL PANELS 2022 - REPLUMB 2022 - NEW SEPTIC 2025 - 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.
Listing is courtesy of: LPT REALTY LLC (386-388-7877)
Listing Agent: Greg Roberts, Llc (407-927-5303)
1610 LYNDALE BLVD, MAITLAND, FL 32751
$1,021,00037 Days on yellowkey MLS ID: G5109784
REDUCED by $54,000 (5.0%) on 04/24/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2598 Built: 2006 Tax: $17,444 (2025)Community: Dixie TerraceSingle Family
Taxes:$17,444
Remarks: PRICE REDUCTION, Incredible price for this property! LOCATION, LOCATION, LOCATION! Ideally situated just off Park Avenue in the highly desirable Maitland/Winter Park area, this beautifully maintained home offers the perfect blend of charm, functionality, and convenience. Featuring 4 bedrooms and 3.5 bathrooms, the home welcomes you with elegant formal living and dining spaces enhanced by detailed trim work, crown molding, and updated lighting. The spacious kitchen is designed for both everyday living and entertaining, showcasing a large quartz island and seamlessly overlooking the inviting family room, highlighted by a stunning fireplace. Step outside to a private backyard retreat complete with a spacious deck and covered patio—ideal for enjoying Florida’s outdoor lifestyle and hosting gatherings year-round. The primary suite, located on the second floor, offers a peaceful escape with its own private balcony—perfect for morning coffee or evening relaxation. The spa-like primary bathroom has been fully updated with a large walk-in shower, freestanding soaking tub, and modern finishes, along with an expansive walk-in closet featuring custom built-ins. Additional highlights include a freshly painted interior, a newer roof (2023), a fully fenced yard, large shed and beautifully landscaped grounds with irrigation and mature fruit trees. The extended driveway leads to a detached 2-car garage equipped with an electric vehicle charging station for modern convenience. Home is zoned for Winter Park Highs school and Dommerich Elementary. It is also conveniently located just minutes from Enzian Theater, Park Maitland School and the top shopping and dining destinations Winter Park has to offer, this move-in ready home delivers exceptional living in one of Central Florida’s most sought-after locations.
Listing is courtesy of: CAPITAL EQUITY REAL ESTATE CO (321-300-4211)
Listing Agent: Christian Del Pino (407-925-9389)
2150 TORTOISE SHELL DR, MAITLAND, FL 32751
$429,9002 Days on yellowkey MLS ID: O6392895
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1512 Built: 1997Monthly Fee: $17 Tax: $5,334 (2025)Community: WinfieldSingle Family
Taxes:$5,334
Middle School: Lockhart Middle
Remarks: One or more photo(s) has been virtually staged. Welcome to this beautifully maintained home in the heart of Maitland, offering the perfect blend of comfort, functionality, and Florida lifestyle living. This thoughtfully designed residence features a bright and open layout with spacious living areas, soaring ceilings, and an abundance of natural light throughout. The kitchen serves as the heart of the home, complete with ample cabinetry, generous counter space, and a convenient breakfast bar that opens seamlessly to the main living and dining areas, ideal for both everyday living and entertaining. Sliding glass doors lead to a private backyard with a paver patio, creating the perfect space to relax or host gatherings. The primary suite offers a peaceful retreat with plenty of space, natural light, and an en-suite bathroom for added convenience. Additional bedrooms are well-sized and versatile, perfect for guests, a home office, or growing households. Situated on a quiet street, this home features a fully fenced yard, mature landscaping, and a two-car garage. Conveniently located near shopping, dining, major roadways, and top-rated schools, this property combines tranquility with accessibility. Don’t miss the opportunity to make this move-in ready Maitland gem your own, schedule your private showing today.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Claire Sims Llc (203-767-8109)
106 OAKWOOD DR, MAITLAND, FL 32751
$649,90042 Days on yellowkey MLS ID: O6390412
REDUCED by $30,000 (4.4%) on 04/16/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1877 Built: 1963 Tax: $1,940 (2024)Community: N/ASingle Family
Taxes:$1,940
Remarks: One or more photo(s) has been virtually staged. 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.
Listing Agent: Kikzeny Cartagena (215-359-6910)
623 GREEN MEADOW AVE, MAITLAND, FL 32751
$525,00072 Days on yellowkey MLS ID: O6380203
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1909 Built: 1970 Tax: $2,070 (2024)Community: Forest Brook 3Rd SecSingle Family
Taxes:$2,070
Remarks: Welcome to this two-owner concrete block home offering the perfect blend of comfort, character, and Florida outdoor living — all with no HOA and an ideal Central Florida location. A majestic Kapok tree gracefully anchors the front yard, while a lush, foliaged trellis guides you to the inviting front entrance, setting the tone for the unique charm found throughout. Inside, you’ll discover an open floorplan designed for both everyday living and effortless entertaining. The kitchen is a true showstopper, featuring a gorgeous tongue-in-groove ceiling, stylish pendant lighting, and a chef-inspired gas range that will delight any home cook. The living spaces flow seamlessly, creating a bright and welcoming atmosphere. The generous primary bedroom offers a relaxing retreat, while three additional bedrooms and two full baths provide flexibility for family, guests, or a home office. An oversized double garage adds convenience and plenty of storage. Step outside to your private backyard oasis. A screened patio and rear yard pergola invite year-round outdoor enjoyment, while the terraced backyard leads down to a serene pondfront, inground pool — perfect for relaxing, entertaining, or simply taking in the peaceful water views. Ideally located just minutes from Full Sail University, along with Winter Park, Casselberry, Winter Springs, and Altamonte Springs, this home offers both tranquility and easy access to shopping, dining, and major commuter routes. This is Florida living at its finest — schedule your private showing today! ROOF/HVAC/Water Heater 2021
Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)
Listing Agent: John Muccigrosso, Pa (407-234-6330)
2040 THUNDERBIRD TRL, MAITLAND, FL 32751
$700,00046 Days on yellowkey MLS ID: O6389391
0 Days Off yellowkey (back on 3/13/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1856 Built: 1963 Tax: $5,731 (2025)Community: Dommerich/ Highland ParkSingle Family
Taxes:$5,731
Remarks: 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!
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Crystal Grohowski, Llc (407-462-7736)
612 GREEN MEADOW AVE, MAITLAND, FL 32751
$500,0003 Days on yellowkey MLS ID: O6401412
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1707 Built: 1970 Tax: $5,400 (2024)Community: Forest Brook 3Rd SecSpa: YesSingle Family
Taxes:$5,400
Remarks: Welcome to a home that doesn’t just check boxes — it supports your lifestyle. Tucked into one of Maitland’s beloved neighborhoods, Forest Brook, this delightful property blends comfort, practicality, and a little everyday serenity. *Lots of new since 2023: Whole house generator, 20’x12’ shed, front and back sod (just completed 4/2026), renovated driveway, gutters, vinyl fence in backyard & so much more!!* Home oozes charm showcasing a sunny yellow exterior with shutter details, white columns on covered front porch, fresh Florida style landscaping, finished concrete driveway, all leading you to covered front entry with pretty leaded glass front door. Step inside to tiled foyer entry and you’ll find a split floor plan offering privacy, flow, and room to spread out — whether you’re hosting, working from home, or simply enjoying a quiet morning. Separate formal dining room complete with sparkling chandelier and French door to patio has yard views. Generous living room has wood floors, new ceiling fan and wall of windows with double French doors to patio plus Plantation shutters. Inviting kitchen is a true gathering spot with a large island with seating on both sides, not to mention all the counter space, white cabinetry, complete stainless steel appliance package and new window above sink. Dedicated office/bonus space has ceiling fan and French door to patio with Plantation shutters. Spacious primary suite flaunts Plantation shutters, new ceiling fan, a walk-in closet plus an en-suite bath with adult height dual vanities, private commode and tiled shower stall. Two guest bedrooms on the other side of the home share updated bath with stylish modern vanity, dual sinks, decorative framed mirrors, chic light and a tub/shower combo. Unwind out back on the oversized covered and screened patio with dual ceiling fans offering lots of gathering space. Every room on the backside of the home contains a French door making it the perfect opportunity for that indoor-outdoor feel. Oversized backyard is fully fenced, freshly sodded and creates the perfect lush, green space ready for play, pets, gardening or gatherings. 20’x12’ shed is a dream for storage lovers or anyone who needs extra space – double doors, tons of room and endless possibilities. No power outages here! A whole house generator keeps life running smoothly no matter the weather. No scrambling, no stress — just uninterrupted comfort and security. Tree lined streets and quick access to parks, major connectors like 436, 414, N Orlando Avenue, Howell Branch Rd/Horatio, Red Bug Rd plus the YMCA, Advent Health and endless dining and shopping options like the Maitland City Center, Downtown Winter Park and so much more— it’s the kind of place where life feels a little easier and a lot more enjoyable!
Listing is courtesy of: FLORIDA HOME TEAM REALTY LLC (407-774-8100)
Listing Agent: Stacy Wayne (407-415-9484)
140 WIGWAM PL, MAITLAND, FL 32751
$649,9003 Days on yellowkey MLS ID: O6401560
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2236 Built: 1957 Tax: $3,978 (2025)Community: Dommerich EstatesSingle Family
Taxes:$3,978
Remarks: One or more photo(s) has been virtually staged. Tucked away on a cul-de-sac in beautiful Maitland, this 3-bedroom, 3-bath home with a bonus room offers space, comfort, and privacy on a generous 1/3-acre lot. With 2,236 square feet of living space and a 2-car garage, the home features an updated kitchen and upgraded bathrooms, blending modern touches with everyday functionality. Enjoy cozy evenings by the fireplace or relax in the bright sunroom overlooking the fully fenced backyard with a concrete wall for added privacy. A screened-in porch provides the perfect spot to enjoy Florida living year-round. This home’s prime location in Maitland provides easy access to top-rated schools, parks, shopping, dining, and major highways, making it both a peaceful retreat and a convenient base for daily living!
Listing Agent: Blake Bolton (407-318-0361)
67 CYPRESS LN, MAITLAND, FL 32751
$1,130,000107 Days on yellowkey MLS ID: O6371328
REDUCED by $95,000 (7.8%) on 04/16/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2292 Built: 1979Monthly Fee: $8 Tax: $4,139 (2024)Community: Maitland ShoresSingle Family
Taxes:$4,139
Remarks: Welcome to 67 Cypress Lane, a stunning single-owner custom residence nestled among majestic Cypress and Oak trees across from Lake Maitland in one of the area's most coveted neighborhoods. This architectural gem, expertly crafted from Western Red Cedar, offers two stories of thoughtfully designed living space with 4 bedrooms and 3 full baths. Step inside to discover hardwood floors flowing throughout the first level, leading to a dramatic sunken living room and formal dining room perfect for entertaining. The heart of the home is the spectacular family room featuring soaring 17-foot ceilings, a wood-burning fireplace, and expansive windows that bathe the space in natural light. The well-appointed kitchen boasts granite countertops, a charming breakfast nook, and glass sliders opening to a covered side porch—ideal for morning coffee or evening relaxation. The main level also includes a convenient guest bedroom and full bath, separate living and dining rooms, plus an attached 2-car garage. Upstairs, retreat to the loft-style primary suite with private en suite bath, two additional guest bedrooms, a hall bath, and laundry facilities for ultimate convenience. Outdoor living shines here with a front deck off the family room and multiple porch spaces. The quiet, dead-end street ensures peace and privacy. For just $100/year, the optional HOA provides deeded park access to beautiful Lake Maitland directly across the street—feel the refreshing lake breeze from your front door! Just minutes from the Winter Park Racquet Club and all that downtown Winter Park and Maitland have to offer. Zoned for award-winning Dommerich Elementary, Maitland Middle, and Winter Park High School. Complete with Terminix termite bond for peace of mind. This tranquil neighborhood retreat offers a rare combination of custom quality, natural beauty, and an unbeatable location. Don't miss this exceptional opportunity!
Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)
Listing Agent: Kelly Price (407-645-4321)
210 ALPINE DR, MAITLAND, FL 32751
$550,00025 Days on yellowkey MLS ID: O6395056
3 Days Off yellowkey (back on 4/23/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1328 Built: 1950 Tax: $7,052 (2025)Community: Sunset RidgeSingle Family
Taxes:$7,052
Remarks: Under contract-accepting backup offers. Don't miss this Great opportunity in the Maitland-Winter Park area! There's Potential for Renovation, Expansion or Development with this property. Imagine the Improvements that can be made for the Future. This is a One Owner Home held be the same family since the 1960s. New roof in 2022. The adjacent property at 220 Alpine is also available for purchase.
Listing is courtesy of: PREMIUM PROPERTIES R.E SERVICE (407-380-2800)
Listing Agent: Beth Hathaway (407-314-1300)
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