Location: Winter Garden
Do Not Show Listings
5079 PALMETTO PARK DR, WINTER GARDEN, FL 34787
$930,00014 Days on yellowkey MLS ID: G5114492
Bed: 5 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3866 Built: 2017Monthly Fee: $190 Tax: $6,877 (2026)Community: Orchard Hills Ph 3Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,877
Elementary School: Keene Crossing Elementary
High School: Windermere High School
Tax Year: 2026
Middle School: Bridgewater Middle
Remarks: Welcome to this beautifully maintained 5-bedroom, 3.5-bath home with a spacious 3-car garage, offering the perfect blend of comfort, style, energy efficiency, and location. From the moment you step inside, you’ll appreciate the soaring ceilings, open living spaces, and thoughtful upgrades throughout. The custom stone fireplace, bring an inviting ambiance to those cozy evenings or when entertaining guests year round. At the heart of the home is the gourmet kitchen, featuring granite countertops, built-in appliances, abundant cabinetry, and plenty of space for cooking and entertaining. The adjoining living area is highlighted by a built-in fireplace, creating a warm and inviting focal point for family gatherings. One of the home’s standout features is the fully owned solar system, helping keep monthly electric costs exceptionally low—averaging approximately $33 per month. The exterior has been recently painted, adding fresh curb appeal. Step outside to the expansive backyard designed with possibilities in mind. The generous outdoor space offers ample room to add a pool whilst still leaving plenty of space for a dedicated grilling and outdoor dining area. Whether you're hosting summer barbecues, family gatherings or relaxing with friends, the spacious yard provides the ideal setting for creating your own private outdoor retreat. The modern floor plan offers five bedrooms and 3.5 bathrooms, providing flexibility for families, guests, or a home office, along with a generous 3-car garage for vehicles and additional storage. Ideally located in one of Winter Garden’s most desirable communities, this home is zoned for highly rated schools and offers convenient access to Walt Disney World, SR-429, downtown Orlando, and Orlando International Airport (MCO), making commuting, travel, shopping, dining, and entertainment easily accessible. If you’re looking for a move-in-ready home with premium features, exceptional energy savings, generous living space, and an outstanding location, this home is ready to welcome you.
Listing is courtesy of: FLORIDA PLUS REALTY, LLC (352-901-9100)
Listing Agent: Claire Brooks (407-967-5829)
14301 WHITE MOSS WAY, WINTER GARDEN, FL 34787
$949,99925 Days on yellowkey MLS ID: G5114391
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 4053 Built: 2015Monthly Fee: $190 Tax: $9,701 (2026)Community: Orchard HillsSpa: NoSingle Family
Taxes:$9,701
Remarks: Virtually Staged. Beautifully maintained 5-bedroom, 3.5-bath home with over 4,000 square feet in the highly sought-after Orchard Hills community. Situated on a spacious corner lot, this home offers an ideal floor plan with the primary suite on the first floor and expansive living spaces designed for both everyday living and entertaining. The gourmet kitchen features stainless steel appliances, double wall ovens, an oversized center island, abundant cabinetry, a butler’s pantry, and a large walk-in pantry, all overlooking the open family room and screened lanai. This home is loaded with valuable upgrades, including a SOLAR energy system that helps keep electric costs exceptionally low, with most monthly electric bills averaging around just $33. Additional improvements include a HYBRID energy-efficient water heater, a Pelican whole-house WATER FILTRATION system, and CUSTOM his-and-hers walk-in closets in the primary suite. There is NO CARPET throughout the home, with luxury vinyl plank flooring covering the entire second floor for a modern, low-maintenance finish. The spacious first-floor primary suite offers a private retreat with dual custom walk-in closets and an elegant en-suite bath featuring dual vanities, a makeup station, an oversized walk-in shower, and a soaking tub. Upstairs, you’ll find four additional bedrooms, two full bathrooms, a large loft, and a separate bonus/media room, providing flexible space for family, guests, or working from home. The back yard is fully fenced and plenty of room for a pool. Residents of Orchard Hills enjoy resort-style amenities including a community pool, fitness center, clubhouse, playground, dog park, and walking trails with the pool and clubhouse being a couple of minutes walk. The home is zoned for highly rated schools and is conveniently located just minutes from Walt Disney World, the rapidly growing Hamlin Town Center, shopping, dining, and entertainment. With easy access to SR 429, the Florida Turnpike, and SR 408, commuting is simple, and Orlando International Airport is within easy reach. Combining energy efficiency, extensive upgrades, generous living space, and an exceptional location, this home is truly move-in ready.
8721 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787
$679,00082 Days on yellowkey MLS ID: G5111855
0 Days Off yellowkey (back on 7/21/2026)
REDUCED by $16,000 (2.3%) on 06/08/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2842 Built: 2015Monthly Fee: $342 Tax: $8,082 (2025)Community: Waterleigh Ph 1ASpa: NoSingle Family
Taxes:$8,082
Elementary School: Panther Lake Elementary
High School: Horizon High School
Tax Year: 2025
Middle School: Water Spring Middle
Remarks: A second chance opportunity to own this exceptional home! Back on the market through no fault of the property, as the previous contract was unable to close due to the buyer's financing. Corner lot! Pool home! Located in Horizon West's Waterleigh - Marina Bay neighborhood. With views of Hickorynut Lake from the front porch and theme park fireworks from the back porch and pool, you have found resort-style living with easy access to everything Central Florida has to offer. Looking for more privacy while enjoying the heated pool? Simply close the privacy curtains that are installed around the pool cage. Inside, you’ll find a spacious home that includes 4 bedrooms, 3 and a half bathrooms, a flex space, a loft, ample storage, and much more. The primary suite is located on the first floor, while one of the second floor bedrooms is designed like a secondary primary with a bathroom en suite. Take advantage of numerous upgrades throughout including, Smart Home features, security options, car charger in garage, wood and tile flooring throughout, granite countertops, plantation shutters, under stairs storage and attic storage where drywall and lighting have been added. Recent updates include, pool (June 2023), exterior paint (Feb 2022), HVAC (Jan 2022), pavers cleaned & sealed (June 2023). When not enjoying the beauty of your home, take advantage of the numerous resort-style amenities that come with living in Waterleigh including, lawn & landscaping maintenance provided by the HOA, two large clubhouses with rentable space, four resort-style pools, two fitness centers, tennis, sand volleyball, mini-golf course, walking paths that take advantage of how the neighborhood wraps around the lake, regular community events, and so much more. As you venture outside of the community you find the home’s location puts you in close proximity to schools, Orange County National Golf, the numerous village centers of Horizon West, Historic Downtown Winter Garden, and quick access to all Central Florida has to offer with 429 connecting you to the Florida Turnpike, 408, and I-4.
Listing is courtesy of: KELLER WILLIAMS ELITE PARTNERS III REALTY (321-527-5111)
Listing Agent: Joshua Howard (407-739-9118)
14543 GOLDEN HARBOR LN, WINTER GARDEN, FL 34787
$525,00025 Days on yellowkey MLS ID: O6420711
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2039 Built: 2017Monthly Fee: $164 Tax: $7,337 (2025)Community: Watermark Ph 2CSingle Family
Taxes:$7,337
Middle School: Hamlin Middle
Remarks: Welcome to this beautifully updated 3-bedroom single-family home in the watermark community of Winter Garden! This move-in ready residence features freshly painted interior walls throughout the entire home and brand new flooring on the entire second floor, including the staircase. The spacious upstairs living area is flooded with natural light and provides an open, airy feel for relaxing or entertaining. Strategically located in Horizon West area, this home provides an unbeatable combination of convenience and lifestyle: Just 0.2 miles from highly-rated Panther Lake Elementary School (8/10) 3.1 miles from Hamlin Middle School (9/10) Directly across the street from Starbucks, 7-Eleven, Walgreens, and a variety of restaurants. Only 15 minutes to Disney Magic Kingdom. Buyer Agents are welcome.
Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)
Listing Agent: Steven Koleno (804-656-5007)
142 SOUTHERN PECAN CIR #205, WINTER GARDEN, FL 34787
$297,90038 Days on yellowkey MLS ID: O6414551
1 Days Off yellowkey (back on 7/21/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1453 Built: 2005Monthly Fee: $563 Tax: $3,928 (2025)Community: Southern Pines CondoCondo
Taxes:$3,928
Elementary School: SunRidge Elementary
High School: West Orange High
Middle School: SunRidge Middle
Remarks: Under contract-accepting backup offers. Seller Offering Up to $7,000 Toward Buyer Closing Costs and a one YEAR AHS Home Warranty. Use our Preferred Lender and they will contribute $1000 towards closing costs with loan approval at closing! $8000 total value to BUYER at closing!! Move-in ready and priced under $298,000, this beautifully updated condominium in the gated Southern Pines community offers exceptional value just minutes everything needed for a balanced lifestyle. Located only 7 minutes from Historic Downtown Winter Garden, this second-floor residence combines modern upgrades, generous storage, and resort-style amenities in one of the area's most convenient locations. The open-concept floor plan features spacious living and dining areas accented by engineered hardwood flooring that extends throughout the main living spaces and into a dedicated office alcove with custom built-in shelving. Fresh interior paint, updated lighting fixtures, ceiling fans and plenty of windows create a bright, contemporary feel throughout. The primary suite offers brand-new carpet, a generous walk-in closet, and a private bath featuring a large walk-in shower, granite-topped vanity, and updated lighting. Two additional bedrooms also feature new carpeting, updated fans and lighting fixtures, and oversized walk-in closets. A well-appointed secondary bath includes an extended granite vanity with abundant storage and a versatile tub/shower combination. At the center of the home, the upgraded kitchen showcases white cabinetry, granite countertops, a new stainless-steel sink with drying rack and pull-down faucet, plus a complete suite of brand-new appliances including refrigerator, range, microwave, and dishwasher. A dedicated laundry area with storage shelving and a separate adjacent linen closet provide added convenience, while multiple walk-in closets in the bedrooms have an uncommon amount of storage for condominium living. Major systems have already been addressed for peace of mind. The HVAC system has recently had seasonal servicing. The hot water heater is awaiting permitting and will be replaced in June 2026, and the home is protected by a transferable home warranty plan. (Covers Appliances, Ceiling Fans, HVAC, HWH, disposal, plumbing and more) Southern Pines residents enjoy an impressive amenity package including gated entry, on-site management, resort-style pool and spa, fitness center, tennis courts, indoor basketball court, volleyball court, playground, pet park, clubhouse with theater room, billiards room, computer center, BBQ area, and even a resident car wash station. Conveniently located just minutes from Publix, Winter Garden Village, the West Orange Trail, Downtown Winter Garden, major shopping, dining, and entertainment, with quick access to the Turnpike, SR 429, I-4, Orlando attractions, and area employers. HOA dues include internet, basic cable, recreational amenities, trash service, and exterior lawn and maintenance. No worries here about Roof Replacement or Exterior Maintenance cost, true worry free living. This is the complete condominium lifestyle package—updated with NEW NEW NEW is really move-in ready in an amenity-rich, and ideally located community. Come see it today, we would love to show it to you.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Mildred Hershiser (407-758-5263)
13011 TRANQUIL WATER ALY, WINTER GARDEN, FL 34787
$514,99049 Days on yellowkey MLS ID: O6414240
REDUCED by $20,000 (3.7%) on 07/21/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2078 Built: 2025Monthly Fee: $160 Tax: $1,747 (2025)Community: Serenade At OvationSingle Family
Taxes:$1,747
Elementary School: None
Middle School: None
Remarks: Major Price Improvement!! Take advantage of the 4.99% interest rate if you close by the end of July 2026!!! Welcome to Serenade at Ovation, one of Winter Garden's most desirable new home communities, where modern design meets an unbeatable Central Florida lifestyle. This completed brand-new Cooper floor plan offers 2,078 square feet of thoughtfully designed living space with 3 bedrooms, 2.5 baths, a versatile loft, and a 2-car garage, all perfectly positioned with the front of the home overlooking peaceful conservation views. The open-concept layout is ideal for both everyday living and entertaining. At the heart of the home, the gourmet kitchen showcases beautiful quartz countertops, elegant linen cabinetry, and abundant workspace while seamlessly connecting to the spacious dining and living areas. Stunning level-three natural wood-look plank tile flooring flows throughout the first floor, creating warmth, durability, and timeless appeal. Upstairs, the spacious primary suite serves as a private retreat featuring a large walk-in closet, dual-sink vanity, and oversized walk-in shower. Two additional bedrooms, a full bath, and a flexible loft provide plenty of space for a home office, media room, playroom, or additional gathering area. Modern finishes, energy-efficient construction, and thoughtful design details throughout make this home truly move-in ready. Residents of Serenade at Ovation enjoy an exceptional location in the heart of Winter Garden, one of Central Florida's fastest-growing and most sought-after communities. Just minutes away, Historic Downtown Winter Garden offers charming brick-lined streets, boutique shopping, farmers markets, live entertainment, and an impressive selection of local restaurants, cafés, breweries, and outdoor dining options. Nearby Winter Garden Village provides convenient access to popular retailers, grocery stores, fitness centers, and everyday conveniences. Outdoor enthusiasts will appreciate close proximity to the award-winning West Orange Trail, numerous parks, lakes, golf courses, and recreational opportunities throughout the area. Families and professionals alike will enjoy the community's convenient access to major roadways including State Road 429, Florida's Turnpike, State Road 535, and Interstate 4, providing quick connections to Downtown Orlando, Disney, Orlando International Airport, and the region's major employment centers, entertainment destinations, and attractions. Experience the perfect combination of contemporary living, natural surroundings, and unmatched convenience in this exceptional new home at Serenade at Ovation.
Listing is courtesy of: LPT REALTY LLC (386-388-7877)
Listing Agent: Peter Yates, Pa (407-417-3636)
13023 TRANQUIL WATER ALY, WINTER GARDEN, FL 34787
$524,99031 Days on yellowkey MLS ID: O6419366
REDUCED by $15,000 (2.8%) on 07/21/2026
15357 OAK APPLE CT #4C, WINTER GARDEN, FL 34787
$340,00092 Days on yellowkey MLS ID: O6401625
REDUCED by $4,900 (1.4%) on 07/20/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1699 Built: 2008Monthly Fee: $285 Tax: $4,779 (2025)Community: Tucker OaksCondo
Taxes:$4,779
High School: None
Remarks: Wow! Winter Garden Corner unit located in the gated community of Tucker Oaks in sought-after Winter Garden, this beautifully upgraded condo-townhome style offers a bright open-concept layout along with 3 bedrooms and 2.5 bathrooms. This stunning home offers the perfect blend of modern upgrades and serene privacy. As one of the few units backing directly onto a lush conservation lot, you’ll enjoy peaceful, wooded views and extra natural light that only a corner position can provide. Relax on your back patio with no rear neighbors and a private forest backdrop. The community offers a pool, walking paths, basketball courts, BBQ area, playground, not to mention, minutes from the West Orange Trail and downtown Winter Garden’s charm. You deserve this home.
Listing is courtesy of: THE SIMON SIMAAN GROUP (407-558-1396)
Listing Agent: Ali Mazahaem Flores (407-485-4177)
12033 ENCORE AT OVATION WAY, WINTER GARDEN, FL 34787
$749,99029 Days on yellowkey MLS ID: O6418908
REDUCED by $30,000 (3.8%) on 07/21/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2740 Built: 2026Monthly Fee: $169 Tax: $2,512 (2025)Community: Encore At OvationSpa: NoSingle Family
Taxes:$2,512
Elementary School: Water Spring Elementary
Remarks: Welcome to 12033 Encore At Ovation Way in Winter Garden, Florida! This new construction home built by M/I Homes offers 2,740 square foot of thoughtfully designed living space with 4 bedrooms and 3 full bathrooms. The functional floorplan offers versatility for a variety of lifestyles while maintaining a cohesive flow throughout the home. The home's design balances aesthetic appeal with practical functionality, creating spaces that are both beautiful and livable. This beautiful two-story home features an open-concept living space perfect for entertaining and family gatherings, a first-floor bedroom, a versatile loft space, a wrap-around front porch, an extended covered lanai, and a 2-car garage. Located upstairs off the loft, your owner's bedroom provides convenience and privacy with its en-suite bathroom and large walk-in closet. Experience the comfort and style of new construction without the wait. This move-in ready home offers the perfect opportunity to start fresh in a brand new space that hasn't been lived in before. Schedule a viewing today to experience firsthand what makes this Winter Garden home special!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)
Listing Agent: Stacie Brown Kelly (407-221-4954)
9561 WATERWAY PASSAGE DR, WINTER GARDEN, FL 34787
$729,0007 Days on yellowkey MLS ID: O6426027
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3267 Built: 2018Monthly Fee: $255 Tax: $6,570 (2025)Community: Waterleigh Ph 2BSingle Family
Taxes:$6,570
Elementary School: Atwater Bay Elementary
Remarks: Designed for comfortable everyday living and easy gatherings, this inviting Waterleigh home pairs a flexible two-story layout with fresh interior finishes and thoughtfully connected living spaces. Brand-new interior paint creates a bright, polished backdrop throughout, while decorative wainscoting and chair rail added in 2021 bring character to the main living areas. Just off the foyer, a versatile flex room can serve as a home office, formal dining room, playroom, hobby space, or additional sitting area based on your needs. Wood-look tile extends across the first floor, where wide archways create an easy flow between the kitchen, casual dining area, and family room. The kitchen is anchored by a large island with seating and features white cabinetry, stainless steel appliances, a blue glass-tile backsplash, generous counter space, a walk-in pantry, and a cabinet-lined serving area. The refrigerator was replaced in July 2024, and the microwave was replaced in November 2023. The first-floor primary suite offers a comfortable retreat with a tray ceiling, multiple windows, and an en suite bath featuring dual vanities, a soaking tub, separate shower, and an exceptionally large walk-in closet. Upstairs, one secondary bedroom includes its own full bath, while two additional bedrooms share another full bathroom with dual sinks. The oversized loft provides adaptable space for media, recreation, work, or hobbies. A dedicated laundry room, powder bath, built-in drop zone cabinetry, and attached two-car garage add everyday convenience. Wi-Fi-enabled features include the refrigerator, washer, dryer, microwave, thermostat, garage door openers, Ring device, and two smoke detectors. The exterior was painted in August 2025, and the covered front porch, covered rear lanai, and grassy backyard provide additional space to relax outdoors. Waterleigh residents have access to amenities throughout every phase of the community, including four resort-style pools, three fitness centers, tennis courts, sand volleyball, mini-golf, multiple playgrounds, pavilions, and walking paths. Lawn maintenance is included with the HOA, allowing more time to enjoy the neighborhood and its convenient Horizon West location near SR-429, shopping, dining, and Central Florida attractions.
Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)
Listing Agent: Christopher Bessette (407-292-5400)
1005 CHASE DR, WINTER GARDEN, FL 34787
$599,99957 Days on yellowkey MLS ID: O6411451
REDUCED by $1 (0.0%) on 07/09/2026
Bed: 4 Bath: 2.5 Gar: 3 Liv Area Sq Ft: 2319 Built: 2005Monthly Fee: $68 Tax: $7,087 (2025)Community: Island Pointe SubSingle Family
Taxes:$7,087
Elementary School: Dillard Street Elem
High School: Ocoee High
Middle School: Lakeview Middle
Remarks: One or more photo(s) has been virtually staged. This is the one in Winter Garden's Golf Cart District. SELLER BONUS: from now until July 31st, the seller will credit up to $5,000 toward a privacy fence on any full-price contract. A fully renovated 4-bed, 2.5-bath home on a corner lot in the golf cart community of Island Pointe, and it is move-in ready. The 2025 updates cover everything: new roof, new AC, updated electrical, updated plumbing, new tile downstairs, LVP upstairs, and a brand new kitchen with stone countertops and modern cabinetry. Double-height ceilings and natural light greet you at the entry, and the kitchen flows right into the living space so the home feels open and connected. The kitchen has stone countertops, soft-close cabinets, a farmhouse deep sink, and real counter space that works for everyday life. The primary suite is its own retreat, with two walk-in closets, a glass walk-in shower, and a soaking tub. Three additional bedrooms give you room to grow. Outside you get a 3-car garage, a corner lot, and a quiet cul-de-sac, all inside the Island Pointe golf cart community. HOA runs $68 a month. Hop on your golf cart and you are minutes from Plant Street, the Saturday farmers market, the West Orange Trail, and some of the best restaurants and coffee in downtown Winter Garden.
Listing Agent: Elizabeth Lofholm (906-221-4905)
1300 EASTERN PECAN PL #208, WINTER GARDEN, FL 34787
$287,00028 Days on yellowkey MLS ID: O6420493
REDUCED by $8,000 (2.7%) on 07/21/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1453 Built: 2005 Tax: $3,625 (2024)Community: Southern Pines CondoCondo
Taxes:$3,625
Tax Year: 2024
Remarks: Beautiful 3-bedroom, 2-bath condominium located in the highly desirable gated community of Southern Pines in Winter Garden. This spacious unit offers 1,453 square feet of living space with an open floor plan, abundant natural light, and a comfortable layout perfect for both homeowners and investors. Residents enjoy resort-style amenities including a community pool, heated spa, fully equipped fitness center, indoor basketball court, tennis and racquetball courts, sand volleyball court, movie theater, game room, business center, and playground. The community is conveniently located near major highways, shopping, dining, entertainment, and historic downtown Winter Garden. Experience maintenance-free living in one of Central Florida's most sought-after communities. Schedule your private showing today.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Paloma Eduar Andrade Froldi (407-360-5466)
17059 HARBOR OAK PKWY, WINTER GARDEN, FL 34787
$620,00025 Days on yellowkey MLS ID: G5114379
REDUCED by $10,000 (1.6%) on 07/05/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2692 Built: 2017Monthly Fee: $215Community: Waterside/Johns Lake Ph 2ASingle Family
Taxes:$0
Elementary School: Hamlin Elementary
Remarks: Motivated Seller! Don't miss your opportunity with this Winter Garden home - offering elegance, convenience and affordability. Situated inside the desirable Waterside community, you will find this beautifully designed residence, blending timeless sophistication with modern comfort, offering an open floor plan, designer finishes, and exceptional indoor-outdoor living. From the moment you arrive, the charming covered front porch, mature landscaping, and inviting curb appeal set the tone. Inside, you're greeted by wide-plank luxury vinyl flooring, soaring ceilings, crown molding, and sun-filled living spaces designed for both everyday living and effortless entertaining. The gourmet kitchen is a true showpiece featuring granite countertops, an oversized center island with seating, farmhouse sink, shaker cabinetry, stainless steel appliances, gas cooktop, double ovens, subway tile backsplash, a custom, handmade hood and designer pendant lighting. Flowing seamlessly into the spacious dining area and family room, this home is ideal for gathering with family and friends. Large sliding glass doors open to an expansive covered lanai with a stunning wood-finished ceiling, creating the perfect space to dine outdoors or just relax. The fully fenced backyard provides privacy, while maintaining a low-maintenance lifestyle. As you journey to the second level, you are greeting by a spacious loft, creating a retreat for unwinding and more closet space. Two large, additional bedrooms and a full bathroom are set off from the primary suite. Escape to your luxurious primary suite, offering a spacious walk-in closet and a beautifully upgraded spa-inspired bath, complete with a custom dual-sink vanity with quartz countertops, elegant gold fixtures, an oversized walk-in shower, and designer tile extending to the ceiling. Additional highlights include double-pane windows, custom window treatments, upgraded light fixtures, abundant storage, an oversized laundry room and pantry and thoughtful designer touches throughout. Residents enjoy outstanding resort-style amenities including a lakeside community pool, clubhouse, fitness center, playground, unfenced dog park and community dock. Ideally located in the heart of Winter Garden, this exceptional home is just minutes from shopping, dining, entertainment, theme parks, major highways, and top-rated schools. This isn't just a home; it's a lifestyle. Book your showing today!
Listing is courtesy of: ERA GRIZZARD REAL ESTATE (352-394-5900)
Listing Agent: Wendy Moore (678-575-5596)
304 ERON WAY #2, WINTER GARDEN, FL 34787
$175,90032 Days on yellowkey MLS ID: O6419000
REDUCED by $2,000 (1.1%) on 07/21/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 840 Built: 1984Monthly Fee: $450 Tax: $2,151 (2025)Community: Townhomes Winter GardenCondo
Taxes:$2,151
Remarks: Priced to sell!! Gorgeous 2 bedrooms-2 bathrooms Corner property condominium in Winter Garden. Open floorplan with a living/dining room combo. Nice size eat in kitchen with kitchen counters for additional seating. All appliances included Refrigerator, stove, dishwater, microwave, washer and dryer. Primary bedroom features private full bathroom 2 assigned parking spots, community swimming pool, exterior maintenance and landscaping are included in the monthly HOA fee. Close to Highway 50, parks, shopping, public transportation and much more.
Listing is courtesy of: LIBERTY HOME SALES INC (321-256-0500)
Listing Agent: Asif Kassim (321-256-0500)
14252 CREEKBED CIR, WINTER GARDEN, FL 34787
$779,90044 Days on yellowkey MLS ID: O6408908
REDUCED by $10,000 (1.3%) on 07/21/2026
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3572 Built: 2014Monthly Fee: $180Community: Bradford CreekSingle Family
Remarks: Welcome to 14252 Creekbed Circle, a spacious and beautifully designed home located in the heart of Winter Garden, in Bradford Creek, one of Central Florida's most sought-after communities. Perfectly situated near Downtown Winter Garden, you'll enjoy convenient access to popular restaurants, boutique shopping, farmers markets, community events, walking trails, and entertainment year-round. This expansive 4-bedroom, 3.5-bath residence offers plenty of room for everyone with a versatile floor plan designed for modern living. The oversized bonus room provides endless possibilities and can be used as a home office, game room, media room, playroom, fitness area, or additional living space to fit your needs. The spacious layout features generous living and dining areas, creating the perfect setting for entertaining guests or enjoying everyday life. The large kitchen with a center island for entertaining and an abundance of cabinets for all of your cooking needs. The private owner's suite offers a relaxing retreat, while the additional bedrooms provide comfort and flexibility for family and visitors. With abundant living space, a desirable location, and easy access to everything Winter Garden has to offer, this home combines convenience, functionality, and lifestyle in one exceptional package. Near Winter Garden Village, Disney and Advent Health in Winter Garden with easy access to 429/408 and the Turnpike. Don't miss the opportunity to make this your next home. Garage equipped with Tesla Charger, Upstairs HVAC replaced 8/2025, Downstairs HVAC replaced 1/2026, Dishwasher replaced 12/2024, Luxury Vinyl Plank flooring installed 12/2025 and new interior paint 5/2026.
Listing is courtesy of: WATSON REALTY CORP (407-323-3200)
Listing Agent: Carla Robles (407-462-2347)
706 CANOPY ESTATES DR, WINTER GARDEN, FL 34787
$1,225,000116 Days on yellowkey MLS ID: O6394059
REDUCED by $34,000 (2.7%) on 06/17/2026
Bed: 5 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 4019 Built: 2018Monthly Fee: $298 Tax: $17,895 (2025)Community: Canopy Oaks Ph 1Single Family
Taxes:$17,895
Elementary School: Lake Whitney Elem
Remarks: Discover luxury living in the gated community of Canopy Oaks, where this exceptional A.R. Bailey Homes Delray floor plan combines timeless design, modern comfort, and an ideal Winter Garden location. Situated within an intimate enclave of only 49 homesites, this meticulously maintained residence offers flexible multigenerational living, expansive entertaining spaces, and seamless indoor-outdoor Florida living just minutes from Historic Downtown Winter Garden, Winter Garden Village, top-rated schools, dining, shopping, recreation, and major roadways. A paver driveway, concrete tile roof, stone-accented exterior, wood-look garage doors, and grand solid wood double-entry doors create a striking first impression. Inside, thoughtfully designed living spaces feature architectural ceilings, abundant natural light, elegant finishes, and an open-concept layout designed for both everyday living and entertaining. At the heart of the home, the chef's kitchen showcases a natural gas cooktop with exterior vent, built-in wall oven, upgraded appliances, pot filler, oversized island, 42-inch cabinetry with crown molding, under-cabinet lighting, tile backsplash, and a spacious walk-in pantry overlooking the coffered-ceiling great room. A gated wine cellar provides a distinctive entertaining feature rarely found in this price range. The first-floor primary suite offers a private retreat with dual granite vanities, a soaking tub, oversized walk-in shower with dual shower heads and bench seating, and a custom walk-in closet. A separate first-floor en-suite bedroom offers flexibility for guests, extended family, or a private home office. Upstairs, a second primary suite is complemented by two additional en-suite bedrooms, a spacious loft, guest powder bath, and covered balcony, creating exceptional privacy and versatility for family and guests alike. Designed to embrace Florida's outdoor lifestyle, dramatic corner-opening glass doors and expansive stacking sliders connect the interior to the covered lanai, complete with a motorized retractable screen for year-round enjoyment. The oversized backyard, enclosed by a stucco privacy wall, provides ample space for a custom pool, outdoor kitchen, or personalized outdoor living area. Additional highlights include dual tankless water heaters, dual HVAC systems with zoned climate control, motorized roller shades, decorative iron stair railings, a mudroom, reading nook, and generous storage throughout. Canopy Oaks residents enjoy nature trails, a community playground, and convenient access to the Roper YMCA, Orlando Health, Historic Downtown Winter Garden, Winter Garden Village, the Florida Turnpike, SR 429, SR 408, and Interstate 4. Offering five en-suite bedrooms, dual primary suites, luxury finishes, and an exceptional Winter Garden location, this beautifully maintained residence presents an outstanding opportunity to enjoy refined Central Florida living. Also available for lease (MLS #O6416527).
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Lisa Rutkowski (407-793-2416)
14140 COUNTRY ESTATE DR, WINTER GARDEN, FL 34787
$996,975104 Days on yellowkey MLS ID: O6397262
REDUCED by $25 (0.0%) on 05/28/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2346 Built: 1984Monthly Fee: $71 Tax: $10,303 (2025)Community: Country LakesSingle Family
Taxes:$10,303
Remarks: Virtually Staged. Rarely does a property offer over an acre of land in the heart of Winter Garden. Tucked away in an intimate lake-access community, this beautifully refreshed pool home combines privacy, mature trees, and an unbeatable location just minutes from everything Central Florida has to offer. Set on a beautifully landscaped 1.1-acre lot with no rear neighbors, this stunning residence offers a rare opportunity to enjoy space, serenity, and flexibility in one of Winter Garden's most desirable locations. Designed for both everyday living and effortless entertaining, the home features fresh interior paint, new luxury vinyl plank flooring throughout the main living areas and bedrooms, a newer roof, new water heater, oven, range, custom woodwork, and a beautiful wood-burning brick fireplace that anchors the living space. The expansive covered lanai, refinished screened-in pool with a new pump, and spa create a true indoor-outdoor lifestyle, with multiple access points from the home and a kitchen pass-through window that opens directly to the entertaining area. Privately situated on the opposite side of the main 3 bedrooms, the light-filled bonus room features two closets, French doors, its own exterior entrance, and tranquil views of the mature landscaping. Paired with the adjacent full bath, it offers exceptional flexibility as a potential 4th bedroom, private guest suite, in-law suite, home office, or creative space. The 3rd full bath also serves as a convenient pool bath with direct outdoor access to the lanai. Outside, enjoy beautifully maintained gardens, mature trees, a fully fenced backyard, abundant outdoor living space, and a large detached storage building with electricity. Residents also enjoy private access to Black Lake and Lake Tilden, complete with a boat ramp, tennis court, pavilion, and the peaceful charm of one of Winter Garden's hidden-gem communities. Just minutes from Winter Garden Village, historic Downtown Winter Garden, major highways, area hospitals, and world-famous attractions including Disney World, Universal Orlando, and SeaWorld, this property delivers a combination of land, location, and lifestyle that is rare to find.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Erin Rison (407-844-8168)
455 WESTPOINT GARDEN CIR, WINTER GARDEN, FL 34787
$330,00014 Days on yellowkey MLS ID: O6423147
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1588 Built: 2006Monthly Fee: $123 Tax: $4,229 (2025)Community: Westpoint TownhomesTownhouse
Taxes:$4,229
Remarks: Beautiful End-Unit Townhome in the Heart of Winter Garden! Welcome to this beautifully maintained 3-bedroom, 2.5-bathroom end-unit townhome, offering the perfect combination of comfort, functionality, and location. The open-concept layout creates a bright and inviting living space, while the kitchen features solid wood cabinetry, a spacious countertop, and a full appliance package, making meal preparation and entertaining effortless. Upstairs, you'll find three generously sized bedrooms, including a comfortable primary suite with a private full bathroom, plus an additional full bath to serve the remaining bedrooms. A convenient half bath is located on the first floor for guests. This home also includes an attached one-car garage and a large screened-in rear lanai, perfect for enjoying Florida's outdoor lifestyle year-round. As shown in the photo, the covered and screened patio provides an ideal space for relaxing, dining outdoors, or entertaining while overlooking the backyard. Located in the Westpoint Townhomes community, the HOA helps maintain the neighborhood and offers a low-maintenance lifestyle. The property is just minutes from Historic Downtown Winter Garden, the West Orange Trail, Winter Garden Village at Fowler Groves, Publix, ALDI, restaurants, shopping, medical facilities, and provides easy access to SR-429, Florida's Turnpike, and Highway 50, making commuting throughout Central Florida convenient. The home is also zoned for Tildenville Elementary, Lakeview Middle, and West Orange High Schoo
Listing Agent: Elisa Seixas, Pa (321-663-0519)
8289 TOPSAIL PL, WINTER GARDEN, FL 34787
$890,00051 Days on yellowkey MLS ID: S5151179
2 Days Off yellowkey (back on 7/21/2026)
REDUCED by $30,000 (3.3%) on 06/16/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2755 Built: 2020Monthly Fee: $350 Tax: $11,564 (2024)Community: Lakeshore Preserve Ph 5Spa: NoSingle Family
Taxes:$11,564
Remarks: Stunning home 4 bedrooms all suites, located in the Lakeshore community. This beautiful residence offers a perfect blend of modern elegance and comfort. House just has been used from Original owner twice a year since built as a second home, looks brand new! Fully upgraded Kitchen with High end Jen Air appliances, Quartz Waterfall Island countertop, upgraded cabinets and quartz countertops thru out the house.. Extensive custom Carpentry work thru out the house. Deep Lot with plenty of space for a large pool with pre wired and pre plumbing for a future summer kitchen. Residents enjoy resort-style amenities, including clubhouse, fitness center, resort-style pool and proximity to top-rated schools, shopping, and major highways.
Listing is courtesy of: MIAMI BRAZIL INVESTMENTS, LLC (561-479-9047)
Listing Agent: Ricardo Oliveira (561-479-9047)
13822 JOMATT LOOP, WINTER GARDEN, FL 34787
$975,00056 Days on yellowkey MLS ID: O6411926
REDUCED by $25,000 (2.5%) on 06/24/2026
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3828 Built: 2016Monthly Fee: $75 Tax: $12,039 (2025)Community: Cypress Reserve Ph 1Spa: YesSingle Family
Taxes:$12,039
Remarks: Under contract-accepting backup offers. Welcome to 13822 Jomatt Loop! This stunning home offers 4 spacious bedrooms, 3 full bathrooms, a bonus loft space, private office and a 3 car garage off of an expansive driveway, all perfectly situated on an OVERSIZED FULLY FENCED LOT. Designed for both comfort and entertaining, the open-concept floor plan features generous living and dining spaces filled with natural light, and was just freshly painted throughout. The primary bedroom is located on the first floor and features his and hers walk in closets with CUSTOM BUILT INS, dual vanity spaces, a free-standing soaker tub, and spa like shower. Located on the second level is a large bonus room that's perfect for kids to play, a movie room, game room, and so much more. Step back outside to your personal backyard oasis where you can enjoy year-round Florida living with a heated sparkling pool and spa that's peacefully nestled between lush landscaping and a fully fenced yard. The expansive covered lanai is enhanced by a stunning outdoor kitchen by Paradise Grills, ideal for hosting gatherings, weekend barbecues, or simply unwinding at sunset. Additional upgrades include GAS APPLIANCES, custom living room built in entertainment center, automated pool pump, and various other thoughtful finishes throughout that elevate both style and function. This home is zoned for A-rated schools including Sunridge Elementary School and Sunridge Middle School, making it an exceptional choice for families seeking top-tier education options. Schedule your showing today! With its rare oversized conservation lot, luxury outdoor living, and prime location, this home truly checks every box. Schedule your private showing today and experience the lifestyle you’ve been waiting for.
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Jenna Palmero (407-697-8727)
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