Location: Winter Garden
Do Not Show Listings
15524 AVIATION ALY, WINTER GARDEN, FL 34787
$569,9008 Days on yellowkey MLS ID: O6398331
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2414 Built: 2015Monthly Fee: $328 Tax: $8,711 (2025)Community: Overlook 2/Hamlin Ph 1 & 6Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$8,711
Elementary School: Independence Elementary
High School: Horizon High School
Tax Year: 2025
Middle School: Bridgewater Middle
Remarks: Welcome home to this updated 3 bedroom, 3.5 bath urban cottage in The Cove at Hamlin with large covered front porch that overlooks a greenbelt. The home offers a bright and sunny 2-story foyer, an inviting kitchen with breakfast area, a large great room with recessed lighting, crown molding and a wall of sliders that open to the covered, screened lanai which allows for that indoor-outdoor Florida living. The kitchen offers 42” cabinets, granite countertops, stainless steel appliances, including a gas range, a large walk-in pantry and center island with space for stools. You will also find a guest bedroom suite with walk-in closet and full bath on the main level in addition to the half bath off the kitchen area. The owner’s suite is found on the second level and is highlighted by French doors, tray ceiling and large windows. The en-suite bathroom has duel sinks, large counter space, frameless glass shower and a walk-in closet with custom closet organizer. You will also find on the second level a quiet nook with a window (perfect for a desk), the third bedroom and bath and the laundry room with cabinets. Some of the additional upgrades in the home are 8’ doors, Plantation blinds, wrought iron bannister, crown molding and a tankless water heater. The exterior features a screened paved lanai, fenced yard, and new turf that was just added to the side yard. The home has a rear two car garage with ample ceiling storage racks. This sought after community is walkable to the Hamlin Town Center that features stores, restaurants, medical services and is highlighted by Popstroke miniature golf and the Cinepolis movie theater. The community offers a resort style pool with splash pad, clubhouse, fitness center, playgrounds and dog park and is located with easy access to SR429 and the Florida Turnpike. A bonus is the accessibility to Disney and nightly views of the fireworks throughout the community. Come make this your NEW home!
Listing is courtesy of: LOKATION (954-545-5583)
Listing Agent: Nancy Foltz (703-772-0215)
15442 ENCHANTED MELODY WAY, WINTER GARDEN, FL 34787
$609,85029 Days on yellowkey MLS ID: S5146095
REDUCED by $3,050 (0.5%) on 04/13/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2420 Built: 2024Monthly Fee: $95 Tax: $8,065 (2025)Community: Osprey Ranch Ph ISingle Family
Taxes:$8,065
Elementary School: Water Spring Elementary
Middle School: Water Spring Middle
Remarks: Welcome to this stunning corner-lot residence located within the exclusive Osprey Ranch community in Winter Garden, just minutes from Walt Disney World and surrounded by fine dining, premium shopping, upscale hotels, and top-rated schools. This beautifully appointed home offers 2,420 sqft of refined living space, featuring 4 spacious bedrooms and 3 full bathrooms, thoughtfully curated to deliver both comfort and sophistication. A standout feature of this residence is the first-floor bedroom with a full bathroom, ideal for multigenerational living, guests seeking privacy, or a flexible office space. Designed for a seamless indoor-outdoor lifestyle, this home showcases: • A fully private fenced backyard, offering both security and tranquility • Custom-designed window treatments, adding a refined designer touch • Expansive bedrooms filled with natural light and generous proportions • A charming private courtyard, perfect for outdoor dining, BBQs, and entertaining Positioned on a premium corner lot, this residence offers enhanced privacy, abundant natural light, and a distinguished presence within the community. Located within a top-rated school district and in one of Central Florida’s most desirable growth corridors, this property seamlessly blends luxury, functionality, and long-term value. An exceptional residence that blends sophistication, comfort, and an elevated way of living.
Listing is courtesy of: A & V FLORIDA REALTY GROUP LLC (786-641-7923)
Listing Agent: Edgar Brito (786-641-7923)
303 SOUTHERN PECAN CIR #107, WINTER GARDEN, FL 34787
$234,90070 Days on yellowkey MLS ID: S5143459
REDUCED by $5,000 (2.1%) on 04/13/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 838 Built: 2005 Tax: $2,540 (2024)Community: Southern PinesSpa: YesCondo
Taxes:$2,540
Elementary School: SunRidge Elementary
High School: West Orange High
Tax Year: 2024
Middle School: SunRidge Middle
Remarks: Freshly painted 1-bedroom, 1 bath. Ready to move-in. Laminate floors in the dining area, living room, and bedroom. Kitchen and Bath have ceramic tiles. Southern Pines has many amenities, like in door basketball court, a Racketball court, tennis, Volleyball, a car wash, a dog park, playground. Fully equipped Gym and theatre, Pool table in the clubhouse, BBQ Grills and a kitchen area with only a small refrigerator and sink, Great counter space with tables and chairs for small parties. Owner financing available, call for details.
Listing is courtesy of: HOMESMART (407-476-0451)
Listing Agent: Maria Lloret (407-929-1994)
7680 GREEN MOUNTAIN WAY, WINTER GARDEN, FL 34787
$658,90010 Days on yellowkey MLS ID: O6389013
1 Days Off yellowkey (back on 4/13/2026)
Bed: 4 Bath: 2.5 Gar: 3 Liv Area Sq Ft: 2385 Built: 2016Monthly Fee: $252 Tax: $8,915 (2025)Community: Summerlake Pd Ph 3ASingle Family
Taxes:$8,915
Elementary School: Summerlake Elementary
Middle School: Hamlin Middle
Remarks: Under contract-accepting backup offers. Welcome to refined Florida living in this pristine Lennar Executive Collection sprawling ranch home, ideally situated on an oversized, fully fenced home site, in the highly sought-after Summerlake community of Horizon West. Offering over 2,300 square feet of thoughtfully designed OPEN floorplan living, this four-bedroom, 2.5-bath residence with a three car garage(2 tandem with professionally installed overhead storage) has been used exclusively by the owners as their second home for vacation (never rented out) and feels nearly new, with several appliances never even used. At the heart of the home, the chef-inspired kitchen showcases a GAS RANGE, stainless steel appliances, granite countertops, a generous island with abundant seating, a walk-in pantry, and a dedicated dining area that easily accommodates both casual and formal dining. Glass sliders open to the screened lanai, extending the living space outdoors and overlooking the oversized backyard with ample room to design a resort-style pool, outdoor kitchen, and/or a private oasis tailored to your vision. The kitchen flows seamlessly into the expansive great room, creating an ideal setting for entertaining and everyday living. Privately tucked away, the Primary Suite offers a serene retreat complete with crown molding, an en-suite bathroom with dual vanities showcasing granite countertops, a soaking tub, separate oversized walk-in shower, and a custom-designed boutique-style closet that enhances both elegance and organization. The light-filled split-bedroom floor plan features tile and luxury vinyl plank flooring throughout, creating a completely carpet-free interior with a clean, modern aesthetic. Three spacious secondary bedrooms and a full bath are privately positioned toward the front of the home. There is also a laundry room with a drop zone located off the garage entry. Additional upgrades include a tankless water heater, water softener, newer A/C system, a wired security system that is also wired for outdoor cameras , crown molding throughout the primary living area, and an in-wall pest system. Low HOA’s that includes but is not limited to lawn care, bush trimming, and mulch application allows for low-maintenance living. Residents of Summerlake enjoy resort-style amenities including a community pool, clubhouse for social events, fitness center, basketball, tennis/pickleball courts, dog park, playgrounds, zip line ,walking paths, multiple ponds ,fishing dock, all conveniently located near shopping, dining, major highways and world renowned theme parks. You can enjoy Disney fireworks from the community viewing areas. Also, the golfer in you will be happy to know that you are only a short drive away from the Orange County National Golf Course. This exceptional home offers the perfect blend of comfort, elegance, and lifestyle convenience in one of Horizon West’s most desirable communities. Summerlake,Hamlin and Horizon schools were all A rated for the 2024/2025 school year!! SEE DRONE TOUR OF INTERIOR , click on Tour#1
Listing is courtesy of: UPSIDE REAL ESTATE INC (407-308-5750)
Listing Agent: Ann Wargo (407-616-3041)
14058 FRASIER ST, WINTER GARDEN, FL 34787
$459,00058 Days on yellowkey MLS ID: V4947394
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1996 Built: 2023Monthly Fee: $110 Tax: $7,893 (2024)Community: Highland RdgSingle Family
Taxes:$7,893
Elementary School: None
High School: None
Middle School: None
Remarks: Welcome to 14058 Frasier Street in the heart of Winter Garden, Florida—where modern comfort meets small-town charm! Located in one of Central Florida’s most sought-after communities, this beautifully maintained home offers the perfect blend of style, space, and convenience. Step inside to discover an inviting open-concept floor plan filled with natural light, high ceilings, and thoughtfully designed living spaces ideal for both everyday living and entertaining. The spacious kitchen serves as the centerpiece of the home, featuring ample cabinetry, generous counter space, and a seamless flow into the dining and living areas—perfect for hosting family and friends. The primary suite provides a private retreat with a well-appointed en-suite bath and generous closet space. Additional bedrooms are comfortably sized and versatile, ideal for guests, a home office, or a growing family. Every detail has been carefully maintained to create a move-in-ready opportunity. Enjoy Florida living year-round with a private backyard space perfect for relaxing evenings, weekend barbecues, or creating your own outdoor oasis. Whether you envision a garden, play area, or custom patio retreat, the possibilities are endless. If you’re looking for a home that offers comfort, location, and lifestyle all in one—14058 Frasier Street is ready to welcome you home. Schedule your private showing today!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Ali Partovi (386-295-5115)
15324 GILLIGAN CT, WINTER GARDEN, FL 34787
$950,00024 Days on yellowkey MLS ID: O6393498
0 Days Off yellowkey (back on 4/13/2026)
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 2794 Built: 2020Monthly Fee: $102 Tax: $641 (2025)Community: Winding Bay Ph 1BSingle Family
Taxes:$641
Remarks: Under contract-accepting backup offers. Winter Garden’s finest — a spacious 4-bedroom, 3.5-bathroom home with a 3-car garage, pool, outdoor kitchen, and breathtaking pond views. This exceptional home is filled with custom upgrades throughout, including custom beams, a striking stone entry wall, built-in dining seating, an expanded drop zone with additional cabinetry, and a custom bar area complete with a wine refrigerator. The gourmet kitchen features 42-inch white cabinets, stainless steel appliances, a large farmhouse sink, and an oversized pantry/storage area. A first-floor den/office offers the perfect flex space for work or relaxation. Upstairs, the primary suite is a true retreat with a custom-designed bath, wood-trimmed tray ceiling, private balcony overlooking the pond, and custom built-ins in the walk-in closet. The adjacent bedroom has been transformed into a dream walk-in closet with shoe storage and a lighted vanity, but can easily be converted back into a bedroom upon request. Two additional bedrooms complete the second floor, including one with its own private ensuite, while the open loft with custom beams creates the perfect setting for a cozy movie night. A second-floor laundry room adds everyday convenience. Step outside into your private resort-style oasis, featuring stunning pond views, a tongue-and-groove stained ceiling, built-in seating, and a fully equipped outdoor kitchen with sink, grill, pizza oven, refrigerator, and stainless hood. The heated UV-filtered pool, connected to the home’s water softener system, is enhanced by a beautiful stone waterfall. A sauna and cold plunge complete this extraordinary outdoor retreat — truly an at-home resort experience. Lush landscaping surrounds the patio and pool area, creating a tropical and private escape, complemented by thoughtfully added rock garden beds and light paver stone walkways along the side of the home that enhance both beauty and functionality. Beyond the pond, a wooded area owned by Disney provides a protected natural backdrop that will never be developed, preserving both privacy and tranquility. The 3-car garage is equally impressive with custom built-ins, overhead storage racks, and a metallic epoxy floor. New exterior painting is currently in progress. Life here extends beyond the home. Morning walks along tree-lined sidewalks, friendly neighbors, nearby parks, and resort-style community amenities create a rhythm that feels both relaxed and vibrant. Residents enjoy access to a resort-style pool, oversized cabana, sports fields, playground, sidewalks, and two dog parks. Located in an area known for top-rated schools, with convenient access to shopping and dining, and just minutes from Walt Disney World Resort, this home perfectly blends Central Florida convenience with the feeling of being tucked into something truly special. More than a house — this is a place to settle in, build memories, and truly feel at home in Winter Garden.
Listing is courtesy of: REAL ESTATE HOUSE FL INC (407-484-0005)
Listing Agent: Gretchen Carlson (407-484-0005)
14501 GROVE RESORT AVE #1105, WINTER GARDEN, FL 34787
$304,000135 Days on yellowkey MLS ID: O6365470
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1265 Built: 2018Monthly Fee: $805 Tax: $3,954 (2025)Community: Grove Resort And Water ParkCondo
Taxes:$3,954
Remarks: Skip the Elevator. Start the Vacation. First-floor units in Tower 1 at The Grove Resort don't come up often — and when they do, they don't last. Guests love them. No elevator wait, instant access to the pools and waterpark, and the kind of easy resort flow that earns five-star reviews and repeat bookings. This fully furnished 2-bedroom split-plan features soaring ceilings and generous room sizes — and sits at the most convenient location in the resort. Step outside and you're poolside in under a minute. No long corridors. No hauling luggage to an elevator. Just flip-flops on, and you're there. When you're not using it? The onsite professional hotel operator handles everything — bookings, housekeeping, check-in, maintenance, accounting, all of it. You own it. They run it. You collect the benefits of a luxury Orlando vacation property without lifting a finger. Located minutes from Walt Disney World®, The Grove draws family travelers year-round. First-floor units like this rarely stay available. Come see why.
Listing is courtesy of: MBI REALTY LLC (407-821-5036)
Listing Agent: Bill Traback (407-821-5036)
15508 BLACKBEAD ST, WINTER GARDEN, FL 34787
$430,000102 Days on yellowkey MLS ID: O6371455
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1754 Built: 2017Monthly Fee: $313 Tax: $6,652 (2025)Community: Summerlake Pd Ph 2C-2ETownhouse
Taxes:$6,652
Middle School: Horizon West Middle School
Remarks: One or more photo(s) has been virtually staged. If you’re looking for low-maintenance living without giving up space, convenience, or community, 15508 Blackbead Way is worth a closer look. This 3-bedroom, 2.5-bath townhome is located in Summerlake, a well-established Winter Garden neighborhood known for its amenities and everyday ease. The main floor features an open, fluid layout designed for both entertaining and day-to-day living, complete with a convenient half bath. The open kitchen flows naturally into the dining and living spaces, creating a connected feel that works just as well for hosting as it does for quiet nights at home. Upstairs, all bedrooms are thoughtfully positioned alongside a centrally located laundry room, keeping everything right where you need it. The generous primary suite offers comfortable separation from the secondary bedrooms and includes a large walk-in closet. One of the most unique features of this home is the oversized driveway—a rare find for a townhome and a direct result of the lot’s placement. It offers exceptional parking and flexibility, and as an added bonus, you can enjoy views of the Magic Kingdom fireworks right from the driveway—an unexpected and special touch that truly sets this home apart. Summerlake residents enjoy a resort-style pool, fitness center, walking trails, parks, playgrounds, and a true sense of community, including Food Truck Thursdays held on the third Thursday of each month. With easy access to shopping, dining, major roadways, and nearby schools, this is an opportunity to enjoy Winter Garden living with comfort, connection, and less upkeep.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Hilary Hall (407-902-9311)
10224 ATWATER BAY DR, WINTER GARDEN, FL 34787
$799,0007 Days on yellowkey MLS ID: S5147252
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3227 Built: 2018Monthly Fee: $230 Tax: $7,456 (2025)Community: Waterleigh Ph 2BSingle Family
Taxes:$7,456
Remarks: Stunning home located in the highly desirable Winter Garden area, offering a modern and spacious floor plan designed for comfortable living and entertaining. This beautifully maintained property features bright open living spaces, a stylish kitchen with ample cabinetry, and generously sized bedrooms. Enjoy a private outdoor area perfect for relaxing or hosting gatherings. Conveniently located near top-rated schools, shopping, dining, major highways, and just minutes from Downtown Winter Garden, Hamlin Town Center, and Disney attractions. An exceptional opportunity to enjoy luxury, location, and lifestyle in one of Central Florida’s most sought-after communities.
Listing is courtesy of: NAIM REAL ESTATE LLC (818-268-9917)
Listing Agent: Samir Naim (818-268-9917)
15408 LEBEAU LOOP, WINTER GARDEN, FL 34787
$580,00060 Days on yellowkey MLS ID: O6383534
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2415 Built: 2022Monthly Fee: $101 Tax: $7,566 (2024)Community: Winding Bay Ph 3Single Family
Taxes:$7,566
Remarks: Discover the ease of low-maintenance living in Horizon West’s Winding Bay with this 2022- built home. No CDD. Low HOA. And a layout that actually works for real life. Winding Bay offers resort-style amenities including a clubhouse, pool, and dog park, and you’re zoned for Water Spring Elementary and Middle plus Horizon High. The location is what continues to drive demand here: you’re right in the heart of Horizon West, close to everything that makes this area so desirable. Inside, the floor plan is practical and well thought out. The main living area is open and bright, connecting seamlessly to the kitchen with a large island, gas range, quartz counters, stainless appliances, and subway tile backsplash. Clean finishes. Functional space. Nothing wasted. The primary suite is downstairs with tray ceilings, a custom walk-in closet, and a well-appointed bath with dual vanities and a beautifully tiled shower. Laundry is also on the first floor, exactly where it should be. Upstairs, a loft with built-in desk space anchors three generously sized bedrooms and a shared bathroom. It’s a great setup for keeping sleeping spaces separate from the main living area. Outside, you have a covered lanai, vinyl-fenced yard, and alley access to the two-car garage, which keeps the front elevation clean and charming. You’re minutes from Hamlin Town Center, Flamingo Crossings, Disney, dining, golf, shopping, and major highways for easy beach access. If you’re looking for newer construction, smart layout, and strong location in Horizon West, this one is worth a look.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Ken Pozek (407-813-2773)
15716 SWEET LEMON WAY, WINTER GARDEN, FL 34787
$739,00089 Days on yellowkey MLS ID: O6375190
REDUCED by $26,000 (3.4%) on 04/13/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2945 Built: 2021Monthly Fee: $118 Tax: $9,510 (2025)Community: Highlands At Summerlake GrovesSingle Family
Taxes:$9,510
Remarks: Beautiful two-story single-family home located in the highly desirable Winter Garden area, featuring a welcoming front porch perfect for morning coffee. This well-maintained residence offers 2,945 sq ft of heated living space with quality flooring, excellent finishes, and tasteful details throughout. The open-concept main level showcases a spacious living area with a custom accent wall and wood panel detailing, flowing seamlessly into the kitchen and dining spaces. The kitchen features elegant cabinetry and appliances, a large pantry, and a generous island ideal for everyday living and entertaining. A stylish powder room and thoughtfully customized laundry room with utility sink add convenience to the main floor. Upstairs, a large loft provides a versatile second living area, ideal for a media room, study, or additional work-from-home space. In addition to the primary suite, the home offers multiple flexible rooms currently well-suited for home offices, a playroom, or guest accommodations, supporting today’s modern lifestyle. The primary suite includes dual vanities and a beautifully finished walk-in shower. The fully fenced backyard offers privacy and ample space for outdoor enjoyment, complemented by a covered rear patio perfect for relaxing or hosting gatherings. Additional highlights include a garage with built-in storage and organization systems. Located in a deed-restricted community with resort-style amenities, including a community pool, playground, and sidewalks, and conveniently close to shopping, dining, top-rated schools, and major roadways. This home offers the ideal blend of comfort, functionality, and location. Schedule your private showing today.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Any Alves (407-455-0618)
9256 GRAND ISLAND WAY, WINTER GARDEN, FL 34787
$750,0009 Days on yellowkey MLS ID: O6397917
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2507 Built: 2017Monthly Fee: $164 Tax: $6,475 (2025)Community: Watermark Ph 2CSingle Family
Taxes:$6,475
Elementary School: Panther Lake Elementary
Remarks: Welcome to Watermark in Winter Garden one of the most sought-after, resort-style communities in Horizon West. This energy-efficient Meritage home has 4 bedrooms, 2.5 baths, and a super functional layout with high ceilings and great natural light throughout. As soon as you pull up, you’ll notice the stone accents on the exterior, brick paver driveway, and clean curb appeal. Inside, the home has been freshly painted and updated with new luxury vinyl plank flooring upstairs, giving it a modern feel without the maintenance headaches. The layout just makes sense 3 bedrooms and a versatile loft upstairs (perfect for a media room, office, or playroom), and a 4th bedroom downstairs that works great for guests or a private home office. The open-concept kitchen seamlessly connects to the main living area and features granite countertops, ample cabinetry, and an easy flow out to the backyard making it ideal for everyday living or having people over. Out back is where this one really stands out. If you're looking for a backyard oasis, look no further. This home has no rear neighbors backing to a retention pond and conservation beyond that. The pool deck is over 1300 square feet with a heated 6 foot deep 484 square foot custom saltwater pool! Enjoy sunsets, watching Disney fireworks at night or the occasional rocket launch in the distance! It’s a great setup for relaxing or entertaining. Watermark has some of the best amenities around resort-style pool, splash pad, gym, clubhouse, tennis, basketball, dog park, and tons of walking and biking trails. You’re also within walking distance to restaurants and just a short drive to Disney, shopping, and everything Winter Garden and Horizon West have to offer. If you’re looking for a clean, move-in ready home in a great location with a strong lifestyle, this one checks all the boxes!
Listing is courtesy of: DENIZ REALTY PARTNERS LLC (407-704-0780)
Listing Agent: Chris Courtney (407-406-0506)
5596 THOMAS SQUARE DR, WINTER GARDEN, FL 34787
$618,00048 Days on yellowkey MLS ID: O6386791
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2458 Built: 2015Monthly Fee: $324 Tax: $8,569 (2025)Community: Overlook At HamlinSingle Family
Taxes:$8,569
Remarks: Welcome to this beautiful 4-bedroom, 3.5-bath home in the highly sought-after Overlook at Hamlin community of Winter Garden. Ideally positioned with a serene front lake view, this well-maintained residence offers over 2,400 square feet of thoughtfully designed living space. The open-concept floor plan features a spacious kitchen overlooking the main living and dining areas, perfect for everyday living and entertaining. Upstairs, the generous primary suite and additional bedrooms provide comfort and privacy for the whole family. Enjoy outdoor living from the rear patio and the convenience of nearby Hamlin Town Center shopping, dining, parks, and top-rated schools, with easy access to FL-429. A wonderful opportunity to own in one of Winter Garden’s most desirable communities.
Listing is courtesy of: XCELLENCE REALTY INC. (866-595-6025)
Listing Agent: Phoebe Yu (407-446-7588)
8275 BAYVIEW CROSSING DR DR, WINTER GARDEN, FL 34787
$565,0009 Days on yellowkey MLS ID: TB8496196
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2019 Built: 2017Monthly Fee: $312 Tax: $5,109 (2025)Community: Waterleigh Phase 1CSpa: YesSingle Family
Taxes:$5,109
Remarks: **New landscaping in progress with pictures to follow, expected by April month end** Welcome to Waterleigh Phase 1 in Horizon West, Winter Garden, one of the most desirable communities in the area, known for resort-style amenities, scenic lakes, and top-rated schools. This rare one-story Arbor floor plan offers an open-concept layout with a highly sought after private fenced backyard - perfect for relaxing, entertaining, and enjoying Florida living at its best. This home features an extended screened-in lanai & patio upgrade, private backyard with a hot tub, cozy electric fireplace, dedicated home gym space, tandem 3-car garage, fresh exterior and interior paint. This home is move-in ready with thoughtful upgrades. Minutes from Hamlin Town Center, shopping, dining, and entertainment, plus quick access to Disney and major highways. Please schedule a showing to come view this rare opportunity to own a single-story home in Waterleigh Phase 1.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Timothy Shepard (727-204-9618)
238 N MAIN ST, WINTER GARDEN, FL 34787
$600,00011 Days on yellowkey MLS ID: O6397340
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1005 Built: 1950 Tax: $5,389 (2025)Community: Orange Grove SubSingle Family
Taxes:$5,389
Elementary School: Dillard Street Elem
Middle School: Lakeview Middle
Remarks: **** HEART OF DOWTOWN WINTER GARDEN **** CAN'T GET MUCH CLOSER TO ***HISTORIC DOWNTOWN WINTER GARDEN *** THAN THIS! SERIOUSLY! FRESH OWNER REDO WITH DISCERNING DESIGN CHOICES ON THIS SOLID & ADORABLE 3 BEDROOM/2 BATH FENCED YARD (SOLID CONCRETE BLOCK) CHARMER. *** NO HOA OR FEES*** HOOOORAY! & WITHIN STEPS TO DOWNTOWN PLANT STREET, TONY'S, HARLOW GROVE RESTAURANT, CHURCHES, FARMERS MARKET, CROOKED CAN FOOD HALL, JESSIE BROCK COMMUNITY PARK, PUBLIC BOAT RAMP AT NEWTON PARK, AND ALL THAT FAST GROWING DOWNTOWN HISTORIC WINTER GARDEN HAS TO OFFER!!! AMAZING CHANGES ARE ON THE HORIZON!!!----GET IN ON YOUR OWN LOCKED IN LOCATION NOW!!!----- (LOCATED WITHIN THE ZONED GOLF CART DISTRICT). WITHIN MINUTES TO HWY 50, FOWLER GROVES/LOWES/TARGET & 429 FREEWAY ENTRANCE, AS WELL AS FLORIDA TURNPIKE AND E-W EXPRESSWAY ENTRANCES BEING MERE MINUTES AWAY ON EAST PLANT STREET; OH SO CENTRALLY LOCATED DIRECTLY IN "TOWN PROPER" JUST A FEW LOTS UP FROM PLANT STREET; & JUST A LITTLE FURTHER DOWN MAIN STREET AND YOU ARE AT THE PUBLIC BOAT RAMP, NEWTON PARK AND THE FARNSWORTH CITY POOL!!! BEYOND EXCELLENT ACCESS TO MULTIPLE GROCERIES, TAILORS & SHOPPING OPTIONS AT HWY 50, PARK AVENUE, DILLARD STREET AND NEARBY OAKLAND! ALSO, THE WEST ORANGE TRAIL RUNS PERPENDICULAR TO MAIN STREET (YOUR STREET) & IS STEPS FROM YOUR HOME-----CONCRETE BLOCK CONSTRUCTION BUILT W/TERMITE BOND/MONTHLY PEST TREATMENT-ALL WITH MASSEY SENTRICON & TRANSFERABLE BOND TO THE NEW OWNER--- HOME HAS GROOMED MATURE OAKS WITH FENCED IN BACK YARD (WOOD PLANK AND VINYL) WITH ELEVATED WOOD DECK FOR FLIPPING OPEN THE BRAND NEW DOUBLE FRENCH DOORS AND ENJOYING FOR ENTERTAINING!!! ***EXCELLENT VALUE/EXCELLENT LOCATION/GOLF CART DISTRICT/NO HOA!***--WHY RENT WHEN YOU CAN (OWN) YOUR OWN PROPERTY FOR JUST A FEW BUCKS MORE PER MONTH? -----HOME WARRANTY OPTIONS AVAILABLE. WITHIN ZILLOW RANGE PRICING! GREAT DEAL. COME SEE FOR YOURSELF...........
Listing is courtesy of: FOLIO REALTY LLC (407-917-0241)
Listing Agent: Jason Fulmer (321-303-6670)
1075 CHASE DR, WINTER GARDEN, FL 34787
$625,00048 Days on yellowkey MLS ID: O6386607
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2125 Built: 2015Monthly Fee: $41 Tax: $2,734 (2024)Community: Island Pointe SubSingle Family
Taxes:$2,734
Remarks: Welcome to 1075 Chase Drive-located in downtown Winter Garden, just minutes from the charm and energy of Plant Street. This rare, newer-construction single-story home offers a blend of modern comfort and timeless style that’s sure to impress. As you enter, custom tile in the foyer sets the tone, with a versatile flex room to the right—perfect for a home office, formal dining room, playroom, or whatever suits your lifestyle.The open-concept design seamlessly connects the kitchen, dining, and family areas, creating an ideal space for entertaining. The large kitchen island is perfect for cooking, casual meals, or hosting friends and family. Sliding glass doors open to create an effortless indoor-outdoor living experience—perfect for those quintessential Florida days. The split floor plan offers privacy, with the primary suite serving as a true retreat, complete with high ceilings, a double vanity, and a spa-like shower. On the opposite side of the home, you’ll find three additional spacious bedrooms, each with plantation shutters and high end laminate flooring. After a long day, unwind on your fully screened back porch with space for multiple seating areas, or head to the side yard to tend your garden. The thoughtfully designed outdoor living space offers plenty of room for grilling, dining, and relaxing—an entertainer’s dream. Just minutes from your front door, Winter Garden’s vibrant Plant Street awaits, offering an award-winning farmer’s market, local dining, boutique shopping, art galleries, Crooked Can Brewery, the West Orange Trail, and year-round festivals.This is a rare opportunity to own a beautifully crafted home in one of Winter Garden’s most desirable neighborhoods—where modern living meets small-town charm. Call for your private showing today.
Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)
Listing Agent: Katie Bray (407-779-6677)
14501 GROVE RESORT AVE #2527, WINTER GARDEN, FL 34787
$270,000122 Days on yellowkey MLS ID: O6368187
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1544 Built: 2018Monthly Fee: $1,103 Tax: $8,868 (2024)Community: Grove Residence & Spa Hotel Condo IiCondo
Taxes:$8,868
Remarks: Short Sale. Short Sale Opportunity – Fully Furnished 3BR/3BA Condo at The Grove Resort – Vacation Rental Only / No Full-Time Residency Investor Alert! Rare opportunity to own a FULLY FURNISHED and equipped 3-bedroom, 3-bath condo in the sought-after The Grove Resort, one of Orlando’s top vacation-only condo-hotel communities, just minutes from Disney. Turnkey for immediate rental. Large balcony, modern kitchen, and in-unit washer/dryer. High occupancy potential through the on-site rental program. Resort Amenities (included for guests): Surfari Water Park, surf simulator, water slides, laser river. Multiple resort-style pools, hot tubs & cabanas. Lake Austin access with fishing and water sports. Fitness center, arcade, full-service spa, on-site restaurants, bars, market, and conference center, 24/7 front desk, concierge, and gated community security. Prime Location, located in Winter Garden, FL, just minutes to Walt Disney World® and major Orlando attractions. Close to shopping, dining, and major highways. This unit is part of a condo-hotel program: no full-time residency allowed. Short-term rentals only. SHORT SALE – priced to sell fast! A great chance to secure a unit below market value in a high-demand tourist location. Ideal for investors looking for short-term rental income with professional management available on-site. Not suitable for full-time occupancy. Contact us today to schedule a showing and take advantage of this exceptional income-generating property!
Listing Agent: Nayane Seabra (407-535-7815)
14501 GROVE RESORT AVE #1612, WINTER GARDEN, FL 34787
$299,000181 Days on yellowkey MLS ID: S5136940
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1375 Built: 2016Monthly Fee: $875 Tax: $6,828 (2024)Community: Grove Resort And Spa Hotel Condo 1Condo
Taxes:$6,828
Remarks: The VIEW! Come enjoy this EXCEPTIONAL Fully Furnished 6th floor Vacation Condo unit with WATER AND CONSERVATION VIEWS plus Evening Fireworks views from your private South-facing Balcony at The Grove Resort and Spa/Water Park in Orlando near Walt Disney World! Experience the Resort FUN yourself and enjoy the income-producing option to rent out your unit when you are away. This Full-service Fully-furnished Luxury Resort unit is the Birch model (split plan 1375 sq ft) in Bldg 1 section H; Bldg 1 allows financing! Two bedroom suites plus sleeper sofa in the great room, TVs in all rooms, Fully equipped Kitchen, inside private Laundry room, a short walk to Attached Garage parking, and the Fitness Center is conveniently just downstairs! Experience lifetime memories at the multitude of amenities on site: the Surfari Water Park with an amazing FlowRider Surf Simulator, Lazy River, Water slides, numerous pools and activities, cabanas, meeting areas, shopping options and Family Fun Center, or escape just minutes away to neighboring theme parks, shopping, restaurants, and more!
Listing is courtesy of: WATSON REALTY CORP (407-298-8800)
Listing Agent: Lois Ann Cox, Pa (407-666-8452)
17006 SEVILLE ORANGE RD, WINTER GARDEN, FL 34787
$718,79917 Days on yellowkey MLS ID: TB8493597
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2224 Built: 2026Monthly Fee: $84 Tax: $2,363 (2025)Community: Northlake/Ovation Ph 1Single Family
Taxes:$2,363
Remarks: Under Construction. This stunning Plant II single-family home is located in the desirable Northlake at Ovation community. This popular one-story, open-concept layout features 4 bedrooms and 3 bathrooms, ideal for modern living. With finishes from the AW Collection Sapphire vibrant blues meet bright whites for a bold look. Enjoy a chef-inspired kitchen with 42" cabinets, quartz countertops, and large island overlooking the living and dining areas, perfect for entertaining. The home also includes luxury vinyl flooring, a private primary suite with walk-in closet, a covered lanai for outdoor living, and a spacious 2-car garage. Conveniently located in Winter Garden near shopping, dining, major roadways, and top-rated schools. Community amenities include pool, clubhouse, playground areas and dog park.
Listing is courtesy of: ASHTON WOODS FLORIDA REALTY LLC (813-918-4491)
Listing Agent: Reed Williams (813-918-4491)
241 N DILLARD ST, WINTER GARDEN, FL 34787
$1,499,999181 Days on yellowkey MLS ID: O6353975
REDUCED by $100,001 (6.3%) on 04/13/2026
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 3507 Built: 1953 Tax: $2,959 (2024)Community: J L Dillard Sub 3Single Family
Taxes:$2,959
Remarks: Seller financing opportunity!!! Welcome to a Once-in-a-Lifetime Opportunity in the Heart of Downtown Winter Garden Nestled beneath the shade of enchanting oak trees, this stately residence sits proudly on a rare triple lot in one of Central Florida’s most coveted locations — the Golf Cart District of Historic Downtown Winter Garden. Blending timeless character with modern comfort, this property captures the essence of classic Florida living just steps from the West Orange Trail, Lake Apopka, and all the boutiques, restaurants, and entertainment that make Plant Street so special. Step inside and you’ll immediately sense the warmth and natural light that fill every corner of this inviting home. Soaring windows and panoramic glass doors create an airy, open atmosphere, seamlessly connecting the indoors with the lush, private grounds outside. The layout offers three spacious bedrooms and three bathrooms perfectly designed for both daily living and entertaining. The primary bedroom is highlighted with a relaxing hot tub, creating a private retreat within this charming home. At the heart of the home, the oversized living and dining areas flow effortlessly into the kitchen and outdoor spaces, ideal for hosting gatherings under the canopy of mature oaks. Every room feels bright and welcoming, and you’ll always be reminded that you’re just moments away from all the charm, energy, and convenience of Downtown Winter Garden — one of the most desirable small-town destinations in Florida. The property’s expansive outdoor footprint sets it apart — a dream for anyone who values space, privacy, and possibility. The triple lot provides ample room for future additions, a pool, or a garden oasis, while a grandfathered-in workshop offers incredible flexibility for hobbies, storage, or creative endeavors. An additional extended driveway offers generous space to accommodate 2–3 vehicles comfortably, with ample room for a boat, RV, or guest parking — a rare find in this highly sought-after downtown location. Whether you’re arriving by car or golf cart, convenience is unmatched. Enjoy the best of Winter Garden living with shopping, dining, the Farmers Market, Plant Street Market, and the Garden Theatre all within minutes, plus easy access to major highways for seamless commutes. From its timeless curb appeal and breathtaking natural light to its unparalleled location and lot size, this property represents a truly rare offering in one of Florida’s most beloved communities. Opportunities like this simply don’t come around twice. Come see for yourself why this remarkable downtown retreat isn’t just a home — it’s a legacy waiting to be continued.
Listing is courtesy of: HOMEVEST REALTY (407-897-5400)
Listing Agent: Erica Diaz (407-897-5400)
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