Displaying: For Sale
Location: Maitland
Property Type(s): Single Family
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Maitland - 85 properties found
921 N THISTLE LN, MAITLAND, FL 32751
$1,049,00017 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,489
Elementary School: Dommerich Elem
High School: Winter Park High
Tax Year: 2025
Middle School: Maitland Middle
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)
1241 MANCHESTER RD, MAITLAND, FL 32751
$625,00034 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)
106 OAKWOOD DR, MAITLAND, FL 32751
$649,00051 Days on yellowkey MLS ID: O6390412
REDUCED by $900 (0.1%) on 05/02/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1877 Built: 1963 Tax: $1,940 (2024)Community: N/ASingle Family
Taxes:$1,940
Elementary School: Lake Orienta Elementary
High School: Lyman High
Middle School: Milwee Middle
Remarks: One or more photo(s) has been 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.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Kikzeny Cartagena (215-359-6910)
1244 E LAKE COLONY DR, MAITLAND, FL 32751
$1,895,0004 Days on yellowkey MLS ID: O6402702
Bed: 4 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 4478 Built: 2002Monthly Fee: $342 Tax: $17,421 (2025)Community: Lake Colony Ph 02Single Family
Taxes:$17,421
Elementary School: None
High School: None
Middle School: None
Remarks: Modern, mediterranean lakefront residence in one of Maitland’s most desirable GATED communities, positioned on a private cul-de-sac atop a natural rise. Set on over 1.3 acres with approximately 179 feet of frontage on Lake Jackson (ski lake), the property offers a rare combination of elevation, privacy and expansive water views in a central Maitland location with quick access to I-4, downtown Maitland and Park Avenue, Winter Park. Lake Colony Estates is conveniently located across the street from Orangewood School. The home was custom built by Keith Groninger, a 10-time Parade of Homes winner. A tree-lined drive leads to a paved driveway and a welcoming entry with imported hand-crafted 8-foot wood doors and tile roof. Inside, the foyer opens to a dramatic great room with 20-foot cathedral ceilings, clerestory windows and a floor-to-ceiling wood burning fireplace, butlers pantry and wet bar. The home has been refreshed with white interior paint, enhancing the natural light and giving the interiors a timeless backdrop. The gourmet kitchen is designed for both function and gathering, featuring 3cm granite countertops, a large island, 5-burner gas cooktop with custom stone and mortar arch detail, tumbled marble backsplash and vaulted ceilings with exposed wood beams sourced from Pennsylvania. Expansive lake-facing pocketing windows frame Lake Jackson and open the chef’s kitchen to the screened porch for effortless outdoor dining and entertaining The first-floor primary suite features engineered hardwood floors, direct access to the outdoor pool and a spacious bath finished in tumbled marble with a soaking tub, dual vanities and walk-in shower. A large custom walk-in closet provides generous storage. Upstairs, three oversized bedrooms each offer ensuite baths and a large bonus room overlooking the lake. Outdoor living is centered around the covered, screened porch, lakefront setting and gated pool. The private and expansive lawn -179 feet of shoreline, complemented by a private boathouse (newer lift) with direct access to Lake Jackson for boating, skiing, jet skis, canoes, paddleboards and more! Also, enjoy sunrise views over Lake Jackson! Additional features include two new ACs, oversized three-car garage, amazing storage and closet spaces, mature and new landscaping and carefully maintained architectural detailing throughout. American Home Shield home warranty offered with full price or higher offer for American Home Shield. Four point, roof certification and wind mitigation reports will be provided by the sellers.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Jennifer Sloan (407-810-8333)
2809 WAUMPI TRL, MAITLAND, FL 32751
$745,00018 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)
755 WOODSIDE RD, MAITLAND, FL 32751
$999,9995 Days on yellowkey MLS ID: O6402797
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3049 Built: 1974Monthly Fee: $8 Tax: $6,508 (2024)Community: Forest Brook 5Th SecSingle Family
Taxes:$6,508
Remarks: This is the one you've been waiting for- a SLEEK MODERN HOME, where EVERY MAJOR SYSTEM AND FINISH has been REPLACED, REFRESHED and ELEVATED to perfection! Located at 755 Woodside Road in the community of Forest Brook in Maitland with 3,054 Sq Ft. of living space, in a quiet CUL-DE- SAC, this 3 BEDROOM 3 FULL BATHROOM POOL home with 2 Car garage on a .31 ACRE LOT is effortless Florida living. From the moment you arrive you will be impressed with the mature, manicured landscaping and architectural features that sets the tone for the quality you will find inside. From the moment you enter, the EXPANSIVE OPEN FLOOR PLAN draws you in with an effortless flow between living, dining, and entertaining spaces. SLEEK MODERN CABINETRY, MARBLE FLOORING and DESIGNER FIXTURES elevate every room. The chef-inspired kitchen features a LARGE CENTER ISLAND perfect for casual dining, meal prep or gathering with guests. A stylish PASS THROUG BAR connects seamlessly to the Florida Room making entertaining a breeze. The OVERSIZED PRIMARY SUITE is a true retreat with MARBLE FLOORING, an abundance of natural light and CUSTOM SLIDING GLASS DOORS leading to the expansive pool deck. The en-suite bathroom features FLOATING VANITIES, MARBLE FLOORING and a SEAMLESS GLASS ENCLOSED SHOWER and STAND ALONE TUB that continues the modern aesthetic that feels like a five star hotel everyday. Laundry with sink and overhead cabinets is centrally located near the kitchen and primary suite. The focal point of the family room is the stunning MARBLE FACED FIREPLACE. Two generously sized secondary bedrooms are located off the family room, sharing a beautiful bathroom featuring marble floors, floating dual sink vanity and walk-in shower-consistent with the finishes throughout. The Florida Room is where the fun truly begins. Currently set up as the ultimate entertainment space, this incredible space offers endless possibilities- playroom, game room, movie room or the perfect indoor/outdoor lounge for hosting family and friends.NEW OVERSIZED WINDOWS frame spectacular views of the pool, floods the space with natural light and seamlessly connect the indoors to the out. The THIRD FULL BATH located off the Florida Room serves as the POOL BATH with walk-in shower, Jacuzzi, floating vanity and premium finishes. This homes outdoor spaces provide something for everyone. The large, screened-in pool deck features a Tiki Bar and dedicated PROJECTOR SCREEN AREA (Screen & Tiki Bar CONVEY IN THE SALE) perfect for entertaining pool side.The side yard with artificial turf is clean, low maintenance, and pet friendly. A charming brick paver seating area creates as cozy spot to relax, unwind or let the pets roam freely. Enjoy the tranquility of the sound of water flowing from the stone wall fountain feature in the backyard and bring your garden dreams to life planting your favorites in the large stone faced planter box. ADDITIONAL LIST OF UPGRADES: 2020 HARDSCAPE & LANDSCAPING, 2021 NEW WATER HEATER & POOL PUMP, 2024/2025 REPLACED LARGE AC AND DUCTWORK, AC PRIMARY SIDE UNIT, 2025 NEW FLORIDA ROOM WINDOWS, ADDED RID-O-RUST SYSTEM TO WELL FOR IRRIGATION, SCREENED IN POOL/DECK, ADDED DRY BAR WITH UPPER AND LOWER CABINETS IN DINING AREA. Conveniently located minutes away from boutique shopping, acclaimed dining and vibrant entertainment of the beautiful city of Winter Park with easy access to Orlando and surrounding communities. This home won't last long. Call your Agent to schedule a showing today!
Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)
Listing Agent: Diane Heiken (407-920-4491)
320 WHITE OAK CIR, MAITLAND, FL 32751
$849,00052 Days on yellowkey MLS ID: O6390473
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2681 Built: 1973Monthly Fee: $31 Tax: $3,975 (2025)Community: Maitland GroveSingle Family
Taxes:$3,975
Elementary School: Lake Sybelia Elem
High School: Edgewater High
Remarks: OPEN HOUSE SATURDAY MAY 2, 1:00-3:00! ENTERTAINING MAITLAND GROVE POOL HOME. Step inside to discover oversized rooms, including a spacious great room overlooking the covered lanai and swimming pool in a private setting perfect for gatherings. Back yard includes a vinyl privacy fence, Pool resurfaced with Pebble Tec. Patio and pool decking have pavers with plenty of room for extra lounging. Lots of Room for everyone, including lIving Room, Dining Room and 4 bedrooms. Kitchen features all new SS appliances and sink w/ faucet, a separate breakfast room and laundry room. Primary room features en suite updated bathroom with dual vanity, shower, w/ tub, walk in closet and large slider doors overlooking the serene pool. Home offers lots of closet and ample storage. Extra Long driveway with side entry oversized garage includes utility sink. Home has been lovingly cared for. Call to view today!
Listing is courtesy of: OVERSTREET REAL ESTATE INC (407-595-5546)
Listing Agent: Susan Filebark (407-595-5546)
2514 TUSCARORA TRL, MAITLAND, FL 32751
$749,00086 Days on yellowkey MLS ID: O6380728
REDUCED by $10,000 (1.3%) on 04/30/2026
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 3000 Built: 1971 Tax: $4,200 (2025)Community: Dommerich Hills 2 Nd AddSingle Family
Taxes:$4,200
Remarks: To Buyer “Discover the advantage of owning one of Tuscarora Trail’s premier homesites—where space, privacy, and lifestyle come together, all within the highly sought-after Dommerich school district, supporting both today’s living and tomorrow’s resale value. ” Nestled on a serene lakeside setting in the heart of Maitland, this beautifully upgraded 4-bedroom, 2.5-bath home offers more than just square footage—it delivers a lifestyle steeped in comfort, elegance, and Florida charm. Spanning nearly 3,000 square feet on a generous 0.43-acre lot, this residence frames breathtaking lake and sunset views that greet you with every evening breeze. Sunlight dances through expansive glass doors, illuminating open living spaces that flow effortlessly into a resort-style outdoor oasis complete with a sparkling private pool, covered patio, and lush water-framed views—perfect for quiet mornings with coffee or lively gatherings under starlit skies. Inside, thoughtful updates—like fresh interior and exterior paint, major systems enhanced for modern living, and paid-off solar panels for incredibly low utility costs—blend timeless Florida living with smart sustainability. Situated in the highly sought-after Dommerich Elementary and Winter Park school districts, this home embodies both tranquil retreat and everyday convenience. You’re just minutes from the charming boutiques, world-class dining, and cultural attractions of Winter Park’s Park Avenue, and a comfortable drive to Orlando’s theme parks—including Walt Disney World® Resort—and the region’s major airports for effortless travel. Whether you’re hosting family by the pool, savoring sunset reflections on the lake, or enjoying the top-tier schools and vibrant local lifestyle, 2514 Tuscarora Trail is more than a house—it’s home. NO HOA
Listing is courtesy of: NOELKE REALTY (407-607-7166)
Listing Agent: Tom Noelke (407-607-7166)
775 WOODSIDE RD, MAITLAND, FL 32751
$449,0003 Days on yellowkey MLS ID: O6403039
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1456 Built: 1973 Tax: $3,458 (2025)Community: Forest Brook 5Th SecSingle Family
Taxes:$3,458
Remarks: Welcome to 775 Woodside Road, ideally situated on a quiet cul-de-sac just minutes from Maitland and Winter Park’s most popular destinations. This beautifully updated three-bedroom, two-bath home offers an open floor plan filled with inviting living spaces and abundant natural light. Luxury vinyl flooring was installed throughout the home in 2023, while plantation shutters in the living room and bedrooms add both style and privacy. Sliding glass doors from the dining area and primary bedroom open to the spacious backyard, offering plenty of green space and room for a future pool. The kitchen is both functional and welcoming, featuring soft-close cabinetry, quartz countertops, stainless steel appliances, a designer backsplash, farmhouse sink, and a breakfast bar perfect for casual dining or entertaining. All three bedrooms offer generous closet space, complemented by two additional hallway linen closets. The spacious primary suite includes a walk-in closet and an updated bath with a large glass-enclosed shower and dual-sink vanity. The guest bath features a shower/tub combination and an updated vanity. Recent improvements provide peace of mind and include a newer water heater (2019), HVAC system (2020), roof (2021), and a partial re-pipe to reroute the main sewer line (2021).
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Wendy Williams Crumit (321-356-8590)
140 WIGWAM PL, MAITLAND, FL 32751
$649,90012 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)
210 ALPINE DR, MAITLAND, FL 32751
$550,00034 Days on yellowkey MLS ID: O6395056
0 Days Off yellowkey (back on 5/2/2026)
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)
220 ALPINE DR, MAITLAND, FL 32751
$450,00060 Days on yellowkey MLS ID: O6388051
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 988 Built: 1953 Tax: $5,537 (2024)Community: Sunset RidgeSingle Family
Taxes:$5,537
Remarks: Under contract-accepting backup offers. Opportunity in the Maitland / Winter Park area! This one-owner home, held by the same family since the 1960s, is ideally located near shopping, dining, parks, and major roadways, providing convenient access throughout Central Florida. The property offers potential for renovation, expansion, or redevelopment, with a lot that provides space for future improvements. Ideal for homeowners, builders, or investors seeking a property in a desirable and established area. The adjacent property to the west (210 Alpine) is also available for purchase. Contact the listing agent for additional information and pricing on the neighboring parcel.
653 GREEN MEADOW AVE, MAITLAND, FL 32751
$528,0003 Days on yellowkey MLS ID: O6402661
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1909 Built: 1970 Tax: $1,992 (2024)Community: Forest Brook 3Rd SecSingle Family
Taxes:$1,992
Remarks: One or more photo(s) has been virtually staged. Location, Location, Welcome to your new 4 BED 2 BATH home tucked away on a quiet cul-de-sac street in the desirable Maitland community of "Forest Brook" This one-of-a-kind home offers the perfect blend of charm, space, and functionality. Lovingly maintained, the home welcomes you with a grand Foyer, Formal Living and Dinng rooms, open family room, ideal for gatherings. A new updated Chef's Kitchen, complete with a gas range, beautiful Cherry cabinets, new appliances, and new Quartz countertops. The spacious Florida Room has a fun step up bar with pass through access to the kitchen. Perfect for entertaining and offers its own AC/Heater unit. Step outside to the large wrap around Deck. Tons of space for outdoor entertaining. No neighbors behind you, just tons of conservation space. Additional upgrades include Roof-2021, AC-2023-Fl Room, AC-2025, Gas Water Heater-2010, Kitchen appliances 2023, Electrical panel- 2024. This home is ideally located just minutes from Winter Park, Casselberry, Winter Springs, Easy access to shopping, dining, and major commuter routes. Start living your Best Life.
Listing is courtesy of: A+ REALTY PROFESSIONALS, INC (407-702-5243)
Listing Agent: Darlene Chance (407-247-2307)
350 NORTHWIND RD, MAITLAND, FL 32751
$3,100,00094 Days on yellowkey MLS ID: O6377888
0 Days Off yellowkey (back on 5/1/2026)
REDUCED by $199,000 (6.0%) on 04/11/2026
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4819 Built: 2019 Tax: $18,531 (2025)Community: Lake Maitland Owl PreserveSpa: YesSingle Family
Taxes:$18,531
Remarks: Under contract-accepting backup offers. Nestled within the 9-acre Lake Maitland Owl Preserve, this striking contemporary residence—crafted by acclaimed green builder E2 Homes offers a rare blend of architectural distinction, privacy, and natural beauty. Surrounded by protected conservation land, the home delivers a serene retreat just minutes from the vibrant lifestyle of Winter Park. Designed by internationally recognized architect Jose Vengas, the home showcases dramatic ceiling heights, clean modern lines, and expansive glass walls that flood the interiors with natural light while blurring the line between indoor and outdoor living. The thoughtfully designed open-concept floor plan centers around a show-stopping chef’s kitchen featuring custom cabinetry, a statement marble backsplash, and a full suite of premium Sub-Zero and Wolf appliances perfect for both elevated entertaining and everyday living. Living and dining spaces flow effortlessly to a covered outdoor lounge with a fully equipped summer kitchen, overlooking a resort-style pool and spa designed for year-round enjoyment. Whether hosting guests or unwinding in private, this outdoor sanctuary is truly exceptional. All five bedrooms are generously sized private suites, each offering spa-inspired bathrooms with refined finishes and custom detailing. The primary suite is a true retreat, featuring a luxurious bath experience and expansive walk-in closets designed for both beauty and function. A first-floor owner’s suite provides exceptional flexibility for multi-generational living or guest accommodations, while the upper level reveals gallery-style walkways and an elegant terrace that highlights the home’s architectural artistry. With nearly 5,000 square feet of meticulously curated living space, this exceptional estate delivers modern sophistication in one of Central Florida’s most exclusive and private enclaves—just moments from Winter Park’s renowned dining, boutiques, and cultural destinations.
Listing is courtesy of: SOTERA LIVING (407-725-9660)
Listing Agent: Lianna Dangelo (321-446-3509)
2150 TORTOISE SHELL DR, MAITLAND, FL 32751
$429,90011 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 Agent: Claire Sims Llc (203-767-8109)
790 S LAKE SYBELIA DR, MAITLAND, FL 32751
$960,00061 Days on yellowkey MLS ID: G5108209
REDUCED by $15,000 (1.5%) on 05/01/2026
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 2021 Built: 1958 Tax: $6,881 (2025)Community: Acreage & UnrecSingle Family
Taxes:$6,881
Remarks: One or more photo(s) has been virtually staged. Price Improvement! Rare opportunity to own a private 0.66-acre Estate Homesite in Maitland with deeded Private 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)
2065 DERBYSHIRE RD, MAITLAND, FL 32751
$449,990122 Days on yellowkey MLS ID: S5140785
1 Days Off yellowkey (back on 5/1/2026)
REDUCED by $40,000 (8.2%) on 04/05/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1430 Built: 1959 Tax: $1,582 (2024)Community: English Estates Unit 1Single Family
Taxes:$1,582
Remarks: Under contract-accepting backup offers. Beautifully renovated and move-in ready, this 3-bedroom, 2-bath home offers modern design in a .24 acre lots, solid upgrades, and comfortable living in a prime Maitland location. Featuring an open-concept layout filled with abundant natural light, the home delivers a warm and inviting atmosphere from the moment you enter. The updated kitchen serves as the heart of the home, showcasing sleek cabinetry, a spacious island, and a full suite of stainless steel appliances, including refrigerator, stove, microwave, dishwasher, washer, dryer, and range hood—ideal for both everyday living and entertaining. Contemporary flooring flows seamlessly throughout, enhancing the home’s clean and modern aesthetic. Major systems have been thoughtfully updated, providing peace of mind to the next owner: roof replaced in 2021, A/C updated in 2019, and water heater installed in 2020. The home features copper electrical wiring and durable plumbing with cross-linked polyethylene inside walls and PVC piping beneath, reflecting quality construction and modernization. Spacious living areas delivers comfort and functionality, while the backyard provides a versatile outdoor space ready for relaxation, entertaining, or personalization. The property includes a 2-car garage and is located in a community with NO HOA and NO CDD, offering flexibility and lower ownership costs. Conveniently situated near major roads, shopping, dining, and everyday amenities, this home presents an excellent opportunity for buyers seeking style, reliability, and location in one complete package.
Listing Agent: Ceila Morales (888-883-8509)
535 PAWNEE TRL, MAITLAND, FL 32751
$918,00054 Days on yellowkey MLS ID: O6389344
REDUCED by $47,000 (4.9%) on 05/01/2026
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2500 Built: 1957 Tax: $10,356 (2024)Community: Dommerich Estates 1St AddSingle Family
Taxes:$10,356
Remarks: Under contract-accepting backup offers. Welcome to your dream home! This beautifully updated 4-bedroom, 3 bath residence is in one of the area's most desirable neighborhoods. Enjoy a perfect blend of comfort, style, and functionality, complete with modern renovations and exceptional outdoor living spaces. This corner lot home with multiple picturesque windows provides an abundance of natural light! Generously sized bedrooms provide ample space for family, guests, or a home office and include 2 master suites, both with 2 closets. Enjoy cooking and entertaining in the stunning, updated kitchen featuring modern appliances, sleek countertops, and plenty of storage. Luxury vinyl flooring throughout but still the charm of original wood floors in 3 of the bedrooms. Step outside to your own backyard oasis with a sparkling pool with a waterfall feature and paver patio, perfect for relaxing or hosting gatherings. Eco-friendly and convenient, the property includes an electric vehicle charging station. Tucked away yet ready in a moment’s notice is space for your boat, camper, or recreational vehicles. The attached one car garage offers secure storage for tools, bikes, toys, golf cart, hobbies or projects. You are just steps from the neighborhood lake lot where members can enjoy incredible sunsets, fishing, or launch your watercraft and enjoy a day on the lake. Dommerich Estates has a strong sense of community and was designed and built around A rated schools so walking and biking to school is safe and easy. The City of Maitland, despite its close proximity to Orlando, is vibrant with a small-town feel providing events designed to foster connections among residents with walkable neighborhoods, multiple parks and downtown street parties and concerts!
Listing is courtesy of: BHHS FLORIDA REALTY (407-406-5300)
Listing Agent: Shirley Welch (407-718-1450)
636 HILLCREST AVE, MAITLAND, FL 32751
$549,0004 Days on yellowkey MLS ID: O6403352
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1576 Built: 1977 Tax: $6,383 (2025)Community: Greenwood AcresSingle Family
Taxes:$6,383
Remarks: **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to this beautifully updated 3 bedroom, 2 bathroom home offering nearly 1,600 square feet of comfortable living space in the heart of Maitland. Featuring a modern look throughout, this well maintained property showcases luxury vinyl flooring that flows seamlessly through the main living areas, creating both style and durability. The spacious layout includes generous living and dining areas, perfect for relaxing or entertaining, along with a functional kitchen that offers ample storage and workspace. A brand new roof installed in 2025 adds peace of mind and long term value. Step outside to enjoy a fully fenced backyard, ideal for privacy, pets, or outdoor gatherings. A wooden deck provides the perfect space for weekend barbecues or quiet evenings at home. Situated in a quiet, established neighborhood, this home offers a highly convenient location. You are just minutes from major roadways including I-4 and Maitland Boulevard, making commuting throughout Central Florida simple. Nearby shopping and dining options include Maitland Center, Altamonte Mall, and a variety of local plazas along Orlando Avenue. Parks, schools, and everyday essentials are all within easy reach, adding to the home’s overall appeal. This property combines modern updates, functional outdoor space, and a prime location, making it an excellent opportunity for a wide range of buyers.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Thomas Nickley, Jr (407-629-4420)
1501 DRUID ISLE RD, MAITLAND, FL 32751
$824,00048 Days on yellowkey MLS ID: O6389520
REDUCED by $26,000 (3.1%) on 04/28/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 3000 Built: 1971 Tax: $11,716 (2025)Community: Druid IsleSingle Family
Taxes:$11,716
Remarks: LAKESIDE LIVING in Maitland, Florida! 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!
Listing is courtesy of: LAKEFIELD REALTY GROUP LLC (407-383-6497)
Listing Agent: Autumn Makin (352-455-0044)
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