Location: Maitland , 32751
Do Not Show Listings
755 CRANES CT, MAITLAND, FL 32751
$1,395,500369 Days on yellowkey MLS ID: O6299581
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4566 Built: 2009Monthly Fee: $199 Tax: $10,895 (2024)Community: Lake Sybelia CoveSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$10,895
Elementary School: Lake Sybelia Elem
High School: Edgewater High
Tax Year: 2024
Middle School: Maitland Middle
Remarks: One or more photo(s) has been virtually staged. Exceptional value meets timeless elegance in this incredible home nestled in the heart of Maitland, privately situated on a cul de sac within an exclusive gated enclave of custom residences. Perfectly positioned between Lake Sybelia and Lake Catherine, this one owner estate offers a rare blend of sophistication, comfort, and versatility with five spacious bedrooms, four and a half baths, and a three car garage, complemented by soaring ceilings, refined architectural details, and a thoughtfully designed open layout. The gourmet kitchen features solid wood cabinetry, a large island, newer refrigerator, walk in pantry, and dual breakfast bars that seamlessly connect to the formal dining and family rooms, where a cozy gas fireplace and wet bar create an inviting setting for everyday living and entertaining. Designed with flexibility in mind, this home effortlessly adapts to your family’s needs, ideal for traditional living, multigenerational arrangements, a private guest retreat, or a dedicated work from home environment with two wings including one with its own kitchen, expansive living area and bedroom and bath. Upstairs, the luxurious owner’s retreat provides a peaceful escape with a loft style office and sitting area, dual walk in closets, and a spa inspired bath. Outdoors, enjoy a lush tropical setting featuring a sparkling saltwater pool with new equipment, along with papaya trees and blooming amaryllis that create a serene, resort-style atmosphere. Additional highlights include a new roof (2023), first floor laundry with newer appliances, tray ceilings, elegant archways, and low HOA fees, all just minutes from top rated schools, parks, dining, shopping, Winter Park’s Park Avenue and the Winter Park Village as well as many local favorites, offering the perfect combination of privacy, convenience, and endless possibilities to create a space that truly reflects your lifestyle. Enjoy scenic walkability or a bike ride along Lake Sybelia to local cafés, the Sunday Farmers Market, and the Maitland Art Museum in one of Central Florida’s most sought after communities. Schedule your private showing today and experience the extraordinary lifestyle this Maitland home provides.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Jo Ann Lamar (321-231-0052)
1400 LAKE SHADOW CIR #10104, MAITLAND, FL 32751
$148,00079 Days on yellowkey MLS ID: O6377476
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 672 Built: 2000 Tax: $2,238 (2025)Community: Visconti WestCondo
Taxes:$2,238
Tax Year: 2025
Middle School: Lockhart Middle
Remarks: One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Welcome to Visconti, a ~ GATED ~ WATERFRONT COMMUNITY ~ in the heart of Maitland where convenience and lifestyle come together. There is NOTHING you have to do this unit!! This well maintained, FIRST FLOOR, 1 bedroom, 1 bath condo is MOVE-IN READY and positioned with peaceful LAKE AND CONSERVATION VIEWS right outside your door. Tucked toward the back of the community, the setting offers added privacy, quiet surroundings, and a true retreat feel while still being close to everything Maitland has to offer. Recent 2026 improvements set the tone immediately and include BRAND NEW APPLIANCES (JAN 2026) with BRAND NEW WASHER AND DRYER INCLUDED!!, UPGRADED fixtures, FRESH INTERIOR PAINT (JAN 2026), and LUXURY VINYL PLANK FLOORING (JAN 2026) throughout, BRAND NEW WINDOW BLINDS (JAN 2026), and BEAUTIFUL COORDINATING PATIO TILE (JAN 2026), complemented by tile in the bathroom and on the patio for easy, LOW MAINTENANCE living. The layout delivers a light, bright OPEN CONCEPT design that makes smart use of the space. Sliding glass doors bring in great natural light and open to a SCREENED PATIO, ideal for morning coffee or unwinding at the end of the day while enjoying the WATER AND GREENERY VIEWS. The primary bedroom offers a WALK IN CLOSET, and the IN UNIT LAUNDRY ROOM located just off the kitchen adds everyday convenience. Residents of Visconti enjoy RESORT STYLE AMENITIES including a waterfront gazebo, SPARKLING POOL, fitness center, clubhouse, playground, tennis courts, and beautifully maintained grounds. WATER SERVICE AND VALET TRASH are included in the HOA, making condo living simple and efficient. Centrally located near 434, 414, and I 4, with easy access to Maitland Promenade, Winter Park Village, Cranes Roost Park, Uptown Altamonte, shopping, dining, and recreation. Downtown Orlando is a short drive away, offering the best of both convenience and location. If you are looking for FIRST FLOOR LIVING in a GATED, WATERFRONT Maitland community with updated finishes, strong amenities, and a peaceful setting, this home checks all the boxes. Schedule your tour today.
Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)
Listing Agent: Jenny Wemert (407-809-1193)
103 WHITECAPS CIR, MAITLAND, FL 32751
$2,000,00037 Days on yellowkey MLS ID: O6382220
0 Days Off yellowkey (back on 3/16/2026)
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3695 Built: 2026 Tax: $3,439 (2024)Community: Hollieanna Shores 1St AddSpa: YesSingle Family
Taxes:$3,439
Elementary School: Dommerich Elem
High School: Winter Park High
Remarks: 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.
Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)
Listing Agent: Christopher Christensen (407-312-8003)
101 WHITECAPS CIR, MAITLAND, FL 32751
$2,150,00071 Days on yellowkey MLS ID: O6375435
1 Days Off yellowkey (back on 2/16/2026)
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4004 Built: 2026 Tax: $3,987 (2024)Community: Hollieanna Shores 1St AddSpa: YesSingle Family
Taxes:$3,987
Remarks: Under contract-accepting backup offers. Under Construction. An elite expression of sophisticated design and elevated living, this remarkable residence offers a resort-style experience that stands apart in Maitland. This home is positioned on a sprawling corner lot and immediately captivates with a grand façade and undeniable curb appeal. From the moment you step inside, the experience is dramatic and refined. An impressive foyer sets the stage for the elegant interiors beyond, where high ceilings, natural light, and thoughtfully curated finishes create an atmosphere of sophistication and comfort. Designed for both effortless daily living and elevated entertaining, the open-concept layout flows beautifully from the expansive living room into the formal dining space, framed by a striking wall of oversized sliders that open up to the spacious backyard/pool area. The heart of the home is the show-stopping chef’s kitchen featuring stunning Chantilly quartz countertops, a full Thermador appliance suite, and an oversized walk-in pantry. The primary suite is designed to feel like a five-star retreat, featuring a spa-inspired bath offering a freestanding soaking tub, dual vanities, a glass-enclosed walk-in shower, and an expansive closet. Adding to the home’s rarity and versatility, the main level also features a true guest suite perfect for hosting in comfort, as well as a dedicated office. Outside, the backyard is the definition of resort-style living. The sparkling pool and spa anchor the space, surrounded by a generous covered lanai with a summer kitchen and abundant room for lounge seating and al fresco dining. And beyond the home itself, the lifestyle is exceptional. Residents of Hollieanna Shores enjoy access to a shared boat slip giving you access to the Winter Park Chain of Lakes, offering a level of exclusivity and lake-life convenience that takes this property to another level. All of this is just minutes from Maitland City Centre, beloved local parks, the iconic Enzian Theater, and the upscale dining, shopping, and charm of Park Avenue. This home redefines what luxury living looks like in Maitland, where location, design, and lifestyle come together in a home that feels truly unforgettable.
1695 E HORATIO AVE, MAITLAND, FL 32751
$529,000342 Days on yellowkey MLS ID: O6309191
0 Days Off yellowkey (back on 4/6/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1939 Built: 1959 Tax: $6,513 (2024)Community: Dommerich Estates 1St AddSingle Family
Taxes:$6,513
Remarks: Great Location, this home is located on Community of Dommerich Estates, Maitland, Florida, No HOA, Top Rated Shools, less than 1 mile to Lake Minnehaha and approximately 2.6 miles to Lake Maitland, and less than 1 mile to John Langdon Park, John Hudson Park, and Kings Row Park. House is just revitalized with a new fresh interior Stone Eagle Color Paint, Roof replaced in 2024, AC replaced in 2022, Exterior repainted in 2022, and plumbing repipe in 2019. House had tile throughout interior floor. Schedule to view this wonderful home.
Listing is courtesy of: VISTA REALTY INVESTMENT (407-895-5757)
Listing Agent: Tuan Nguyen (407-446-3264)
1106 CHARMING ST, MAITLAND, FL 32751
$495,00026 Days on yellowkey MLS ID: TB8489671
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1870 Built: 2006Monthly Fee: $520 Tax: $6,232 (2025)Community: Enclave/Maitland A-FSpa: NoTownhouse
Taxes:$6,232
Elementary School: None
High School: None
Middle School: None
Remarks: 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.
Listing is courtesy of: FLAT FEE MLS REALTY (813-642-6030)
Listing Agent: Stephen Hachey (813-642-6030)
353 W LAKE FAITH DR #116, MAITLAND, FL 32751
$349,900145 Days on yellowkey MLS ID: O6352070
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1403 Built: 1974Monthly Fee: $554 Tax: $1,848 (2024)Community: Lake Faith Villas CondoCondo
Taxes:$1,848
Remarks: Discover lakeside living at its finest in this beautifully updated 2nd-floor, private lakefront condo in the highly sought-after Lake Faith Villas in Maitland. Offering 1,400+ sq ft, this spacious 2 bed, 2 bath home features stylish parquet flooring throughout, a modernized kitchen and updated baths, newer appliances, HVAC, water heater, and updated electrical wiring for peace of mind. Enjoy breathtaking sunrise views over Lake Faith each morning and, on clear days, catch the awe-inspiring glow of Cape Canaveral rocket launches right from your balcony—protected by newly installed, storm-rated sliding glass doors. Located in a gated community with a sparkling lakeside pool, this condo offers privacy while still delivering exceptional walkability to Maitland’s shops, cafés, and restaurants. Whether you’re relaxing by the water, entertaining in your updated interior, or exploring the surrounding neighborhood, this home blends comfort, convenience, and the beauty of true Florida lakefront living. Call today to book your showing! This one won't last long!
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Travis Cepregi (407-620-2580)
1000 S ORLANDO AVE #B25, MAITLAND, FL 32751
$335,00034 Days on yellowkey MLS ID: O6391679
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 952 Built: 1964 Tax: $2,559 (2025)Community: Maitland Harbour AptsCondo
Taxes:$2,559
Remarks: Highly desirable Maitland Harbour, a boutique 38-residence lakefront condominium community nestled in the heart of Maitland. Ideally positioned on Lake Maitland—the largest lake on the Winter Park Chain of Lakes—this intimate and picturesque enclave offers access to the entire chain and a truly exceptional waterfront lifestyle. A hidden gem, Maitland Harbour blends timeless Mid-Century Modern architecture with the serenity of lakefront living. Designed by renowned architect Manfred Lopatka, a protégé of Frank Lloyd Wright, and built in 1964, the community reflects a distinctive Central Florida interpretation of classic modernist design. Inside this beautifully updated 2-bedroom, 2-bath residence offering 952 square feet, you will find light-filled living space with a clean, cohesive aesthetic throughout. The kitchen, renovated in 2020, features quartz countertops, a subway tile backsplash, open wood shelving, and a pass-through to the dining area, creating both functionality and visual connection to the main living space. The open-concept living and dining areas are bright and inviting, with warm-toned wood flooring and neutral finishes. The primary suite is a true retreat, complete with updated flooring (2020), soft natural light, newly added barn-style closet doors for improved storage access, and direct access to the private balcony—ideal for enjoying morning coffee or evening breezes. The en-suite bath, renovated by a previous owner, features neutral finishes and a glass-enclosed shower. The secondary bedroom is spacious and offers consistent updated flooring and fresh paint, and is located adjacent to a full guest bath with recent updates including vanity, lighting, and fixtures. Additional improvements include a new refrigerator (2023), new windows (2024), new HVAC (2025), and fresh interior paint (2025/2026). The community has completed major improvements including new roofs, pool enclosure, and exterior paint, and both the milestone inspection and structural integrity reserve study have been completed and are available for review. Residents enjoy a full suite of lakefront amenities including a waterfront pool, courtyard, boat slips, fishing pier, kayak storage, community room, private storage, covered parking, and an expansive entertaining deck overlooking Lake Maitland. The location is adjacent to historic Fort Maitland Park and directly across from Lake Lily, the heart of Maitland’s Cultural Corridor, known for concerts, the Maitland Art Festival, and the Sunday Farmers Market, and is just a short walk to the Enzian Theater and local dining, with easy access to Winter Park’s Park Avenue offering premier shopping, restaurants, museums, and year-round events. Enjoy low-maintenance lakefront living with beautiful interior spaces, a private balcony, and access to one of Central Florida’s most sought-after waterfront settings.
Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)
Listing Agent: Padgett Mccormick (407-645-4321)
1732 RIDGEWOOD AVE #S, MAITLAND, FL 32751
$749,00078 Days on yellowkey MLS ID: O6378854
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2407 Built: 2016Monthly Fee: $425 Tax: $6,155 (2024)Community: Ridgewood Villas CondoTownhouse
Taxes:$6,155
Remarks: This custom two-story townhome delivers what most properties in this category simply don’t; space, light, and a layout that actually makes sense. Open, airy, and thoughtfully designed, every detail feels intentional. Perfectly positioned between Maitland and Winter Park, you’re just minutes from Park Avenue, Winter Park Village, and some of the best dining and shopping in Central Florida. Step inside and you immediately notice how expansive it feels. Soaring ceilings and abundant natural light make the home live far larger than a typical townhome. The first floor flows seamlessly, creating a true open-concept environment ideal for entertaining or everyday living. The oversized island anchors the space, perfect for hosting friends, casual dinners, or setting up a productive work-from-home station. Upstairs is where this home truly stands apart. Three full bedrooms, each with its own ensuite bath, a rare and highly desirable feature. The primary suite offers a private retreat with a spacious layout, generous walk-in closet, dual vanities, and a large walk-in shower that feels straight out of a luxury spa. The secondary suites provide comfort and privacy rarely found in townhome living. Step outside and enjoy a private side yard, a perfect extension of your living space. Whether you’re grilling on the weekend, setting up a small outdoor lounge, or simply enjoying the Florida sunshine, this added outdoor area gives you the flexibility most townhomes don’t offer. A private side-entry two-car garage adds both security and convenience while preserving the home’s clean curb appeal. If you’ve been searching for something near Winter Park that offers style, functionality, and location without compromise, this one checks every box.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Brandon Geers (941-928-5152)
150 SENECA TRL, MAITLAND, FL 32751
$745,00034 Days on yellowkey MLS ID: O6389696
1 Days Off yellowkey (back on 3/27/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2221 Built: 1957Monthly Fee: $8 Tax: $10,543 (2025)Community: Dommerich Estates 1St AddSingle Family
Taxes:$10,543
Remarks: Under contract-accepting backup offers. 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.
109 MINNEHAHA CIR, MAITLAND, FL 32751
$770,00091 Days on yellowkey MLS ID: O6374874
1 Days Off yellowkey (back on 4/2/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2249 Built: 1976Monthly Fee: $13 Tax: $3,547 (2025)Community: Minnehaha ShoresSingle Family
Taxes:$3,547
Remarks: Under contract-accepting backup offers. RARE opportunity to own a Maitland Shores home offering access to Lake Minnehaha AND the Winter Park Chain of Lakes. Residents enjoy exclusive use of the HOA lakefront park with a fishing dock and paved boat ramp that creates quick access to the Nina Canal and Lake Maitland — the largest lake in the Winter Park Chain. The unique location of this home offers an oversized .34-acre homesite that is thoughtfully landscaped with rare tropical plants, rose gardens, and a peaceful front courtyard complete with a bubbling fountain. Ample driveway and garage space accommodate boat or vehicle storage, ideal for enjoying skiable Lake Minnehaha. Inside, this 3 bedroom, 2.5 bath home offers 2,249 square feet of living space in a split floorplan. A unique highlight of the floorplan is the dual primary suites, each with private access to the screened pool, making the home ideal for multi-generational living. Equally beautiful pool views are also visible from the kitchen, breakfast nook, and spacious family room. If you are staying inside, the family room features a large fireplace that creates a cozy focal point. Just off the family room is the remodeled kitchen that is both bright and functional with abundant cabinetry, granite counters, stainless steel appliances, breakfast bar seating, a built-in desk, and a breakfast nook with patio access. Beauty abounds from the patio with a resort-style screened pool, complete with decorative palms surrounding the pool. Steps from the pool begin the meandering gardens with colorful blooms. To aid the avid gardener is a covered and secure garden shed. With such an expansive homesite - more than 15,000 square feet - possibilities for adding a full workshop or even an Accessory Dwelling Unit/ADU could be explored. Adjacent to this estate is Minnehaha Park, a 7.5-acre City of Maitland park offering multiple tennis courts, pickleball courts, walking trails, picnic pavilions, and playgrounds. While the setting of this property is quiet and serene, the home is minutes from Winter Park shopping and dining; downtown Maitland and Maitland City Centre; I-4 access; and zoned Winter Park High School. Additional home updates include a full roof replacement and AC replacement in 2021, making move-in and insurance smooth and easy. Don't miss this chance to get Winter Park Chain of Lakes access for yourself at this exceptional price!
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Erin Baker (407-719-0030)
312 MACARTHUR PL, MAITLAND, FL 32751
$774,90078 Days on yellowkey MLS ID: O6379212
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2441 Built: 1981 Tax: $8,950 (2024)Community: Sybelia PlaceSingle Family
Taxes:$8,950
Remarks: NEW ROOF, NEWER AC, and NO HOA—this beautifully maintained home on a quiet cul-de-sac offers comfort, charm, and an unbeatable location. Nestled just steps from Lake Sybelia. This property provides a peaceful, scenic setting while still being close to all that Maitland has to offer, including popular local restaurants, shops, and community spots. A short drive takes you to the vibrant dining, shopping, and cultural scene of Park Avenue, making this home perfectly positioned for both relaxation and convenience. Inside, the home features a bright and inviting open floor plan, ideal for entertaining and everyday living. The seamless flow between the living, dining, and kitchen areas creates a spacious feel filled with natural light. Step outside to a large backyard that offers plenty of room for outdoor enjoyment, gardening, or entertainment. With its mature landscaping and charming appeal, this property is a true garden oasis with central living at its best. A fantastic opportunity in a highly desirable Maitland neighborhood—don’t miss your chance to make this home your own.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Sean David (407-712-4698)
1000 WINDERLEY PL #239, MAITLAND, FL 32751
$299,00021 Days on yellowkey MLS ID: O6395472
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1164 Built: 1982Monthly Fee: $523 Tax: $489 (2025)Community: Sun Bay Club CondoCondo
Taxes:$489
Remarks: 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.
Listing Agent: Nancy Bagby (407-620-8868)
1010 WINDERLEY PL #127, MAITLAND, FL 32751
$339,00022 Days on yellowkey MLS ID: O6395028
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1563 Built: 1997Monthly Fee: $375 Tax: $4,625 (2025)Community: Villas Lake DestinyTownhouse
Taxes:$4,625
Remarks: Welcome to Villas of Lake Destiny, a gated lakefront community tucked quietly in the heart of Maitland, offering a rare blend of privacy, natural beauty, and unmatched convenience. Residents enjoy a serene, low-traffic setting surrounded by mature landscaping, water features, and direct access to Lake Destiny, including a private community boat ramp, lakefront pool, and tennis courts. Located just minutes from I-4, the Maitland Exchange (414), Maitland Center, RDV Sportsplex, shopping, dining, and major employers, this community delivers an ideal balance of lifestyle and accessibility. This beautifully updated townhome features a private 1-car garage with gated courtyard-style entry, creating both security and a welcoming first impression. Inside, soaring ceilings and a transom window over the sliding glass doors fill the home with natural light, leading to a private screened patio that extends your living space outdoors. The main level showcases all tile flooring, a spacious open-concept living and dining area, and a well-appointed kitchen designed for both function and style. Features include upgraded white shaker cabinets with crown accents, subway tile backsplash, an extra-large stainless steel basin sink, glass cooktop with microwave hood, french door refrigerator, and pendant lighting over the breakfast bar. Upstairs and down, the layout offers flexibility and privacy with three generously sized bedrooms, each with ceiling fans and ample closet space. The oversized primary suite is a true retreat with two closets, including a walk-in, and a large ensuite bath featuring dual vanities, a walk-in shower, and a full wall vanity mirror. Additional highlights include brand new carpet, a 30-year tile roof replaced in 2023, HVAC system installed in 2020, modern brushed nickel fixtures throughout, and a versatile 9x9 bonus room with indoor laundry and washer/dryer included. Whether you are looking for low-maintenance living, proximity to everything Central Florida has to offer, or a quiet lakefront community to call home, this property delivers on all fronts.
Listing is courtesy of: DON HARKINS REALTY LLC (321-377-0341)
Listing Agent: Donald Harkins, Iii (321-377-0341)
51 OAKLEIGH LN, MAITLAND, FL 32751
$1,349,00035 Days on yellowkey MLS ID: V4947925
0 Days Off yellowkey (back on 4/1/2026)
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 4149 Built: 1972 Tax: $5,558 (2025)Community: Oakleigh Third AddSingle Family
Taxes:$5,558
Remarks: Under contract-accepting backup offers. WELCOME TO THIS FULLY RENOVATED LUXURY RESIDENCE IN THE HIGHLY DESIRABLE OAKLEIGH SUBDIVISION IN MAITLAND, offering OVER 4,149 SQ FT OF BEAUTIFULLY UPDATED LIVING SPACE on a 0.36-ACRE LOT WITH A PRIVATE POOL, designed for both elegance and everyday comfort. Originally built in 1972 and COMPLETELY MODERNIZED, this SINGLE-STORY ESTATE FEATURES 4 BEDROOMS AND 5 FULL BATHROOMS, including TWO EXPANSIVE PRIMARY SUITES—perfect for MULTIGENERATIONAL LIVING, MOTHER-IN-LAW OR LUXURY GUEST ACCOMMODATIONS. A welcoming FIREPLACE ANCHORS THE MAIN LIVING AREA, creating warmth and architectural charm. The home has been THOUGHTFULLY UPGRADED THROUGHOUT with a BRAND-NEW ROOF, NEW WINDOWS, NEW GARAGE DOOR, AND FRESH INTERIOR AND EXTERIOR PAINT. WIDE-PLANK LUXURY VINYL FLOORING flows seamlessly throughout the living spaces, leading to a FULLY REDESIGNED CHEF’S KITCHEN featuring CUSTOM CABINETRY, QUARTZ COUNTERTOPS, DESIGNER BACKSPLASH, AND UNDER-CABINET LIGHTING. EVERY BATHROOM HAS BEEN COMPLETELY TRANSFORMED with NEW TILE, MODERN VANITIES, LED MIRRORS, AND SMART HEATED AUTO-LID TOILETS. The MAIN PRIMARY SUITE OFFERS A SPA-LIKE RETREAT with a SOAKING TUB AND DUAL SHOWERS. Step outside to enjoy the RESURFACED PRIVATE POOL, along with ENCLOSED AND OPEN PORCH AREAS PERFECT FOR ENTERTAINING OR RELAXING YEAR-ROUND. Additional features include CENTRAL AIR, FORCED-AIR ELECTRIC HEATING, DURABLE CONCRETE BLOCK CONSTRUCTION, AND A SPACIOUS SINGLE-LEVEL FLOOR PLAN designed for comfort and long-term durability. PROPERTY FEATURES: LIVING AREA: 4,149 SQ FT TOTAL BUILDING: 4,413 SQ FT BEDROOMS / BATHROOMS: 4 BED / 5 FULL BATH LOT SIZE: 15,852 SQ FT (0.364 ACRES) POOL: YES STORIES: SINGLE-STORY A RARE FULLY TURNKEY LUXURY OPPORTUNITY IN ONE OF MAITLAND’S MOST SOUGHT-AFTER NEIGHBORHOODS.
Listing is courtesy of: LA ROSA REALTY CW PROPERTIES L (407-910-2168)
Listing Agent: Ricardo Adames (407-279-0018)
2525 CAPER LN #205, MAITLAND, FL 32751
$119,00025 Days on yellowkey MLS ID: O6393931
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 550 Built: 1973Monthly Fee: $216 Tax: $1,541 (2024)Community: Carrington Park A CondoCondo
Taxes:$1,541
Remarks: This bright and inviting second floor condo offers an abundance of natural light throughout. The unit features a full size kitchen, a spacious bathroom with a bathtub and shower combination, and a large walk-in closet for ample storage. Located in the well-established Carrington Park community, residents enjoy access to three swimming pools, a fitness center, and convenient on-site laundry facilities. One of the community pools is ideally situated just steps from the unit. The property is in a prime location within short walking distance to Publix, as well as a variety of restaurants, shops, and public transportation options.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: David Lozano, Llc (407-257-3533)
210 ALPINE DR, MAITLAND, FL 32751
$550,00022 Days on yellowkey MLS ID: O6395056
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: 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)
200 SPARTAN DR, MAITLAND, FL 32751
$540,00022 Days on yellowkey MLS ID: O6394981
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1830 Built: 1962 Tax: $5,197 (2025)Community: Cool-More SubSingle Family
Taxes:$5,197
Remarks: More photos to come soon! Welcome to 200 Spartan Dr, a beautifully updated 3/2 (with bonus room and large laundry room) pool home in the heart of Maitland. The interior has been thoughtfully opened up by removing walls between the living area and kitchen, creating a much more spacious and modern feel, and a large island was added to make the kitchen the center of the home. The home also features a bonus room offering great flexibility for a home office, workout space, or hobby room. Outside, enjoy a private pool and backyard space perfect for relaxing or entertaining. Conveniently located near shopping, dining, parks, and major roadways, this home offers comfort, functionality, and a great Maitland location. Roof, HVAC, and Water heater from 2018.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Nick Mandiola (407-453-0190)
1024 KEWANNEE TRL, MAITLAND, FL 32751
$549,750267 Days on yellowkey MLS ID: O6331331
0 Days Off yellowkey (back on 3/30/2026)
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 1845 Built: 1965Monthly Fee: $8 Tax: $8,403 (2024)Community: Dommerich Hills 3Rd AddSingle Family
Taxes:$8,403
Remarks: One or more photo(s) has been virtually staged. Welcome home to this well outfitted 4 Bed 2.5 Bath home in sought after Maitland. Tastefully upgraded home on a generous lot, with in ground pool. Great upgraded kitchen with custom cabinets for extra storage complemented with upgraded Stainless Appliances and granite counters. Thoughtful upgrades at every turn. Currently zoned for Winter Park HS. Close to everything that Maitland and Winter Park known for, shopping dining and more. Don’t wait, come see today.
Listing is courtesy of: GLORY INTL. REAL ESTATE CO (386-775-7778)
Listing Agent: Patrick D'Agostino (321-467-4555)
1275 LAKE SHADOW CIR #13102, MAITLAND, FL 32751
$166,900159 Days on yellowkey MLS ID: O6360372
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 707 Built: 2000 Tax: $2,180 (2024)Community: Visconti WestCondo
Taxes:$2,180
Remarks: Immediately available! This refreshed 1-bedroom, 1-bath ground-floor condominium with a deeded 1-car garage is the one you’ve been waiting for in the desirable gated community of Visconti West. Tucked away in the back of the community, this home offers a peaceful retreat with a private patio and tranquil surroundings. Step inside to a bright, airy interior featuring all-tile flooring and an open floor plan perfect for both relaxing and entertaining. The modern kitchen boasts stainless steel appliances and a breakfast bar, ideal for morning coffee or casual meals with friends. Just off the kitchen, you’ll find a convenient laundry closet with a full-size washer and dryer. Special note the windows feature plantation shutters to add to the modern feel. The spacious living room flows seamlessly into the open kitchen and the screened-in balcony, where you can unwind outdoors while enjoying the privacy of your quiet setting. A storage closet on the balcony provides extra space for seasonal items or outdoor gear. In addition to your deeded garage, ample open parking is available for guests. At Visconti West, you’ll enjoy resort-style amenities including a sparkling pool, fitness center, clubhouse, playground, and sports courts. Water service and valet trash are included in your HOA, allowing for low-maintenance living. All this luxury for a low reasonable monthly condo association fee. Ideally located near I-4 and SR-414, you’re minutes from Downtown Maitland, Winter Park Village, Cranes Roost Park, and the shops and dining of Uptown Altamonte. With Downtown Orlando only 15 minutes away, you’ll enjoy the best of both worlds—peaceful living in a vibrant, convenient location. This is a must see to appreciate.
Listing is courtesy of: REDFIN CORPORATION (407-708-9747)
Listing Agent: Juan Castro (407-808-5353)
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