Location: Winter Garden
Keyword(s): West Orange High
Keyword(s) High School: West Orange High
Do Not Show Listings
1711 AMSEL FALLS PARK TER, WINTER GARDEN, FL 34787
$1,000,000240 Days on yellowkey MLS ID: O6346377
0 Days Off yellowkey (back on 5/8/2026)
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3863 Built: 2017Monthly Fee: $180 Tax: $10,792 (2024)Community: TwinwatersSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$10,792
Elementary School: Hamlin Elementary
High School: West Orange High
Tax Year: 2024
Middle School: Bridgewater Middle
Remarks: Under contract-accepting backup offers. Welcome to this stunning architectural masterpiece nestled in the heart of Twinwaters, one of Winter Garden’s most sought-after communities. This elegant two-story home seamlessly blends sophistication and comfort, offering over 3,600 square feet of beautifully designed living space. Step through the grand entryway to find soaring ceilings, expansive windows that fill the home with natural light, and designer finishes that exude contemporary luxury. The gourmet chef’s kitchen is a true showpiece—featuring 42” custom cabinetry, gleaming quartz countertops, a massive entertainment island, stainless steel appliances, and a walk-in pantry, perfect for culinary enthusiasts and family gatherings alike. The open-concept great room flows effortlessly into a spacious dining area and covered lanai, ideal for both indoor and outdoor entertaining. Upstairs, the luxurious primary suite offers a serene retreat with a spacious walk-in closets, a spa-inspired bathroom with a deep soaking tub, frameless glass shower, and dual vanities. A versatile loft provides additional space for a home theater, gym, or play area, while the first-floor guest suite ensures comfort and privacy for visitors. The private backyard invites you to create your own oasis—whether adding a pool, summer kitchen, or lush garden escape. Enjoy resort-style amenities including a community pool, playground, and picturesque walking trails, all surrounded by pristine lakes and lush landscaping. Twinwaters is ideally situated near Horizon West, top-rated schools, fine dining, boutique shopping, and major highways for an easy commute to downtown Orlando and world-famous attractions. This home truly embodies the ultimate blend of luxury, location, and lifestyle—a rare opportunity to live beautifully in one of Central Florida’s premier communities.
Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)
Listing Agent: Jay Winston (407-497-1112)
15558 SANDFIELD LOOP, WINTER GARDEN, FL 34787
$765,00075 Days on yellowkey MLS ID: O6393987
REDUCED by $30,000 (3.8%) on 05/08/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 4307 Built: 2014Monthly Fee: $114 Tax: $5,670 (2025)Community: Reserve/Carriage Pointe Ph 1Single Family
Taxes:$5,670
Tax Year: 2025
Middle School: Hamlin Middle
Remarks: One or more photo(s) has been virtually staged. Welcome to 15558 Sandfield Loop, a refreshed residence offering a turn-key lifestyle within one of Winter Garden’s most exclusive and hard-to-find GATED community. This house has been freshly updated from top to bottom, including new interior and exterior paint that makes the whole place feel brand new. The first thing you'll notice when you walk in is the massive, two-story high ceiling in the living area—it brings in tons of natural light and gives the home a great, airy feel. The kitchen has been fully redone with modern two-tone cabinets and beautiful quartz countertops. Throughout the home, you will find fresh paint and new flooring that perfectly complement the contemporary aesthetic. Situated within a highly-rated school zone, this MOVE IN READY property combines the security of a premier gated community with grand architectural features and stylish updates.
Listing is courtesy of: ORLANDO HIGHLAND REALTY LLC (561-385-7610)
Listing Agent: Xiaoli Lin (561-385-7610)
13705 GOLDEN RUSSET DR, WINTER GARDEN, FL 34787
$359,90086 Days on yellowkey MLS ID: O6390740
0 Days Off yellowkey (back on 5/7/2026)
REDUCED by $10,000 (2.7%) on 04/16/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1590 Built: 2007Monthly Fee: $333 Tax: $4,756 (2025)Community: Orchard A1-A26 B1 B2 C D1-D4Townhouse
Taxes:$4,756
Elementary School: SunRidge Elementary
Middle School: SunRidge Middle
Remarks: Under contract-accepting backup offers. Welcome to The Orchard, a tidy gated community of townhomes in sought-after Winter Garden. This residence blends modern comfort with low-maintenance living, offering a bright, open layout that feels inviting from the moment you step inside. Thoughtful upgrades elevate every space—stylish flooring, fresh finishes, and a contemporary color palette create a clean, move-in-ready atmosphere. The kitchen serves as the heart of the home, featuring new appliances, fine cabinetry, sleek countertops, and a functional layout ideal for everyday living. The open-concept living and dining areas flow seamlessly to a private outdoor space, perfect for morning coffee or unwinding at the end of the day. Upstairs, spacious bedrooms provide comfort and flexibility, while the primary suite offers a peaceful retreat with generous closet space and an updated en-suite bath. A dedicated laundry area and attached garage add convenience to the home’s thoughtful design. Residents of The Orchard enjoy gated security, a tranquil pool area and playground, and a prime Winter Garden location just minutes from shopping, dining, top-rated schools, and the charm of downtown Winter Garden. Tastefully updated, well-maintained, and ideally located—this townhome is the perfect blend of style and convenience.
Listing is courtesy of: LAKEFIELD REALTY GROUP LLC (407-383-6497)
Listing Agent: Drew Ross (407-383-6497)
1164 PRADO LN, WINTER GARDEN, FL 34787
$2,210,00034 Days on yellowkey MLS ID: O6403024
0 Days Off yellowkey (back on 5/6/2026)
Bed: 5 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 4204 Built: 2026Monthly Fee: $150 Tax: $399 (2025)Community: Grove/OaklandSingle Family
Taxes:$399
Elementary School: Tildenville Elem
Middle School: Lakeview Middle
Remarks: Pre-Construction. To be built. Welcome to one of the most anticipated new builds at Grove at the Harvest District — the Sunburst Plan by Davila Homes, a luxury new construction masterpiece designed for those who prioritize space, style, and lifestyle. Spanning 4,204 livable square feet with 5,665 total square feet, this stunning 5-bedroom, 5.5-bath estate is thoughtfully designed from the ground up to blend elevated living with effortless entertaining. Every inch reflects Davila Homes' signature commitment to superior craftsmanship, custom finishes, and exceptional attention to detail. Step inside and discover a floor plan built for the way you actually live — an executive office for focused work, a versatile loft for flexible living, and a gracious layout that flows naturally from the heart of the home to the outdoors. The second-floor covered terrace invites year-round relaxation with a front-row view of your private retreat below, where a custom pool and fully equipped summer kitchen set the stage for unforgettable gatherings. The three-car garage rounds out a home that delivers on every level — from daily functionality to that rare feeling of arriving somewhere truly special. Located within the coveted Grove at the Harvest District, this is more than a home — it's a legacy address in one of Central Florida's new communities.
Listing is courtesy of: REGENCY REAL ESTATE LLC (407-469-5021)
Listing Agent: Alexis Anderson (561-670-5901)
17326 BAL HARBOUR DR, WINTER GARDEN, FL 34787
$769,00075 Days on yellowkey MLS ID: O6393857
1 Days Off yellowkey (back on 5/4/2026)
REDUCED by $5,000 (0.6%) on 04/24/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3196 Built: 2018Monthly Fee: $215 Tax: $11,210 (2025)Community: Waterside/Johns Lk-Ph 2BSingle Family
Taxes:$11,210
Remarks: Under contract-accepting backup offers. Stunning lake-view home in Waterside at Johns Lake, overlooking Lake Avalon in Winter Garden! This spacious 5-bedroom, 3-bath residence offers 3,196 sq ft of open-concept living with a desirable downstairs primary suite featuring a spacious, well-appointed bathroom along with a customized walk-in closet. A second downstairs bedroom is paired with a beautifully RECENTLY renovated full bath showcasing a newly upgraded walk-in shower—ideal for guests or multi-generational living. Step inside to a welcoming entry that opens to a versatile sitting area—perfect for a home office or library—leading into a large family room, dining area, and well-appointed kitchen with natural gas range—perfect for entertaining. Enjoy the clean, modern feel of a completely carpet-free interior with durable vinyl flooring throughout the main living areas. The highlight of this home is the oversized screened lanai, perfectly positioned to capture serene Lake Avalon views—an ideal space for morning coffee, outdoor dining, or relaxing sunset evenings. Upstairs features a versatile loft, three additional bedrooms, and a full bath. Residents of Waterside at Johns Lake enjoy resort-style amenities including a lakeside pool, clubhouse, fitness center, scenic walking trails, playground, and community dock. Conveniently located just minutes from Winter Garden Village with easy access to 429, Florida’s Turnpike, downtown Orlando, theme parks, and Orlando International Airport.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Rema Perras (802-233-5292)
15316 OAK APPLE CT #B, WINTER GARDEN, FL 34787
$339,99961 Days on yellowkey MLS ID: O6397688
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1544 Built: 2008 Tax: $4,738 (2025)Community: Tucker OaksCondo
Taxes:$4,738
Remarks: Welcome to your new dream home! Located in the gated community of Tucker Oaks, this 2-story townhome offers 3 bedrooms, 2.5 bathrooms, and 1,544 square feet of comfortable, thoughtfully designed living space. As a corner unit backing to a peaceful conservation area, you’ll enjoy added privacy and tranquil views with no rear neighbors! Step inside to an open-concept first floor where high ceilings, recessed lighting, and natural light create a warm and inviting atmosphere. The layout is ideal for both everyday living and entertaining, with a seamless flow between the living, dining, and kitchen spaces. A conveniently located half bath downstairs adds ease and privacy when hosting guests. The kitchen is designed for functionality and style, featuring stainless steel appliances, crown-molded cabinetry, ample counter space, and a breakfast bar that’s perfect for quick meals or morning coffee. Upstairs, all bedrooms and full bathrooms are tucked away for optimal privacy. The primary suite offers a spacious retreat with a large closet and a private en suite bath complete with a generous vanity and a roomy shower, making it perfect for starting your day or winding down in the evening. Additional bedrooms provide comfortable space for family, guests, or a home office setup. Beyond the home, Tucker Oaks offers amenities including a community pool, playground, dog park, and sidewalks for enjoying the outdoors. The location places you just minutes from major highways, making commuting simple, while also being close to downtown Winter Garden where you can explore local farmers markets, community events, and boutique shopping. The nearby West Orange Trail offers even more ways to stay active and enjoy the Florida sunshine. With theme parks like Walt Disney World and Universal Studios just 25 minutes away, this home combines convenience, comfort, and lifestyle all in one. Don't wait on this amazing opportunity, schedule your private showing TODAY!!!
Listing is courtesy of: DENIZ REALTY PARTNERS LLC (407-704-0780)
Listing Agent: Daniel Deluca (407-916-9780)
143 SOUTHERN PECAN CIR #206, WINTER GARDEN, FL 34787
$279,90042 Days on yellowkey MLS ID: S5148778
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1276 Built: 2005 Tax: $3,705 (2025)Community: Southern Pines CondoCondo
Taxes:$3,705
Remarks: Stunning 2-bedroom, 2-Bath condo on the second floor, 1276 sq ft, with new carpet in the bedrooms and stairs. All Appliances updated in the last few years, and the A/C is just a little over a year old. Walk to the pool, enjoy views of the retention pond, and be close to all the community amenities. Don't miss this gem?
Listing is courtesy of: HOMESMART (407-476-0451)
Listing Agent: Maria Lloret (407-929-1994)
4230 REX DR, WINTER GARDEN, FL 34787
$2,500,000495 Days on yellowkey MLS ID: O6274608
0 Days Off yellowkey (back on 3/26/2026)
Bed: 9 Bath: 6.0 Gar: 5 Liv Area Sq Ft: 7505 Built: 2003 Tax: $16,471 (2024)Community: Lake Avalon Grvs 2Nd RepSpa: YesSingle Family
Taxes:$16,471
Remarks: Under contract-accepting backup offers. **A RARE OPPORTUNITY YOU WON’T WANT TO MISS!!** 9.75 PRIME ACRES IN THE HEART OF WINTER GARDEN ~ MAIN HOME CUSTOM BUILT BY HANNIGAN HOMES 5BD/4BA/3-CAR- 5,423 SQFT, INCLUDING AN ABOVE GARAGE APARTMENT WITH 1/BD/1/BA/+KITCHENETTE ~ SECOND HOME ON PROPERTY INCLUDES 4BD/2BA/2-CAR - 2,082SQFT ~ 10-STALL + TACKROOM HORSE BARN - 2,592 SQFT, 3 PASTURES ~ FENCED IN RIDING RING AND MUCH MORE! This countryside estate is an exclusive opportunity to own two homes, a horse barn, an adorable chicken coop, Koi pond, paver fire pit, built-in playground and so much more in the heart of the sought-after Winter Garden! Bring your horses and enjoy all that this massive CORNER LOT has to offer and being just minutes from the 429 gives you easy access to every convenience including neighboring HORIZON WEST and DISNEY THEME PARKS. Being sold all as one gives you endless opportunities in the ADDITIONAL SINGLE FAMILY HOME with the main home ready with charm for a family to make it their own. The long covered front porch welcomes you home and gives you front row seats to the riding ring. Built by Hannigan Homes, the main home was modeled after Disney’s Grand Floridian, and the thoughtful and unique features throughout are the perfect blend of comfort and quiet luxury. The roof was updated in 2019, the office space can serve as an additional bedroom, light and bright with views of the property, there is a movie/media room currently being used as an indoor trampoline park, WALK-IN WINE CELLAR for the adults, a fun HIDDEN WALK-IN PANTRY for ample kitchen storage and an energy saving SOLAR WATER HEATER. The new owner will absolutely fall in love with the PRIVATE PRIMARY SUITE that takes up the entirety of the second floor with sweeping views overlooking your estate, large WALK-IN CLOSET and well appointed ensuite bath. The additional bedrooms on the main floor give room to grow, and the additional home and garage apartment graciously allow for multi-general living. This gorgeous property is best experienced in person (stunning sunsets included!) so it can speak for itself - call today to schedule your private tour today!
Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)
Listing Agent: Jenny Wemert (407-809-1193)
236 DONALD DR, WINTER GARDEN, FL 34787
$465,00046 Days on yellowkey MLS ID: O6401940
2 Days Off yellowkey (back on 4/30/2026)
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1080 Built: 1930 Tax: $410 (2025)Community: Showalter ParkSingle Family
Taxes:$410
Elementary School: Dillard Street Elem
Remarks: Under contract-accepting backup offers. Calling all buyers, builders, and investors, this is a rare opportunity to secure land with no HOA in the heart of Downtown Winter Garden. Located within the highly sought after Golf Cart District, just 0.5 miles from the iconic Plant Street Market, seconds from the West Orange Trail, and with convenient access to the Florida's Turnpike, this spacious quarter acre lot offers the ultimate combination of freedom, location, and connectivity. Set on a private street, this property is the perfect canvas to build your custom dream home without restrictive guidelines or additional monthly fees. With an existing structure already on site, electricity, water, and essential utilities are already in place, making the building process significantly easier, faster, and more cost effective. Whether you envision a modern custom estate, a charming bungalow, or an investment opportunity, the flexibility here is unmatched. Enjoy the ability to walk, bike, or golf cart to everything downtown has to offer, while being positioned in an area experiencing exciting growth with new dining, retail, and commercial development continuing to expand throughout Winter Garden. Opportunities like this, a no HOA quarter acre lot in the Golf Cart District with prime access and growth around it, rarely come available. This is your chance to build exactly what you have been dreaming of in one of Central Florida’s most desirable and rapidly evolving communities.
Listing is courtesy of: GLOBAL FLORIDA REALTY (407-380-3030)
Listing Agent: Lauren Bouchard (352-978-6837)
14372 SUNBRIDGE CIR, WINTER GARDEN, FL 34787
$745,000220 Days on yellowkey MLS ID: O6356579
REDUCED by $30,000 (3.9%) on 04/29/2026
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3468 Built: 2016Monthly Fee: $166 Tax: $5,745 (2023)Community: Bradford Crk Ph IiSingle Family
Taxes:$5,745
Tax Year: 2023
Remarks: This is a unique opportunity to live in the highly sought-after gated community of Bradford Creek in Winter Garden. Impeccably maintained and lightly lived in, this waterfront oasis with no rear neighbors is a masterpiece of luxury living. Every inch of this 4-bedroom, 4 1/2-bath home reflects thoughtful upgrades and meticulous attention to detail. The innovative 3-way split bedroom plan ensures both privacy and functionality. Step into the expansive great room, complemented by a kitchen that will well exceed your expectations. Boasting wood look plank tile flooring, soft-close cabinetry, and Bosch stainless steel appliances, this culinary haven includes a massive quartz island perfect for both meal preparation and dining. Indulge in the elegant dining room adorned with a coffered ceiling, welcoming family and friends for memorable festive gatherings. The primary suite is an oversized sanctuary with coffered ceilings, custom California Closets, a luxurious newly installed Jacuzzi tub, and a rejuvenating shower. The 2nd bedroom is an oversized private bedroom suite with a full bath which is ideal for second primary bedroom, fitness room or playroom. The strategically located middle 3rd bedroom, featuring French doors, is an ideal space for a home office. The private 4th bedroom is en-suite and completes the first floor. The upstairs bonus room, complete with a powder room, offers versatility for home theater entertainment, game room or relaxation. Just a few minutes' walk to Winter Garden Village for shopping, dining and numerous events throughout the year, major commuter routes close by, walking, biking, and jogging trails. Just under a mile from downtown Historic Winter Garden, where the ever-popular Farmer's Market takes place every Saturday and of course, the well-known West Orange Trail that runs down the middle of the town. Bring your most discerning buyer – this home is a true delight that surpasses expectations!
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: Julie Bettosini, Pa (321-689-9594)
17608 DEER ISLE CIR, WINTER GARDEN, FL 34787
$1,025,000243 Days on yellowkey MLS ID: O6350825
1 Days Off yellowkey (back on 4/27/2026)
REDUCED by $25,000 (2.4%) on 04/20/2026
Bed: 4 Bath: 2.5 Gar: 3 Liv Area Sq Ft: 3144 Built: 1997Monthly Fee: $207 Tax: $6,334 (2024)Community: Deer Island Ph 02Spa: YesSingle Family
Taxes:$6,334
Remarks: Under contract-accepting backup offers. Bring your ideas to a truly exceptional custom home, perfectly situated in a private, gated community on the shores of breathtaking John’s Lake. Set on over an acre of a beautifully updated landscaped property with panoramic water views throughout the island, this 4-bedroom estate offers the ultimate Florida lifestyle — complete with resort-style amenities and convenient access to Historic Downtown Winter Garden, as well as Downtown Orlando and major attractions just 30 minutes or less away. Your ideas await as charm and craftsmanship are evident in every detail. Step through the front door into an inviting floor plan that seamlessly blends elegance with functionality. The spacious living room is anchored by a cozy wood-burning fireplace, enhanced by warm canned lighting and plantation shutters that frame every window. Wood flooring flows throughout the main living areas, setting a tone of timeless sophistication. The kitchen features granite countertops, KraftMaid cabinetry, Sub-Zero refrigerator, cooktop, double ovens, and a large pantry. The open design keeps the heart of the home connected to the main living space — ideal for entertaining and family gatherings but separate enough to hide the meal prep! The primary suite is a peaceful retreat, with serene views of the pool, dual walk-in closets, garden tub, separate shower, and a cleverly designed storage area. The home's split-bedroom layout ensures privacy for guests and family alike and are all thoughtfully located on the first floor. Upstairs, two large bonus rooms offer endless possibilities — from a playroom to a home theater — and includes a hidden safe room / office with skylights and easy attic access for extra security and utility. The 3 car garage features extra width for additional storage and Gladiator garage organizational wall units. Step outside into your private backyard paradise, where a sparkling saltwater pool and attached hot tub await, surrounded by pavers and an outdoor grilling station. Whether hosting a summer barbecue or enjoying a quiet evening under the stars, this backyard fenced-in space delivers year-round relaxation. Eight outdoor security cameras offer peace of mind, while a three-car garage and spacious driveway provide ample storage and parking. An in-wall pest control system, central vacuum, built-in wine bar, hidden storage and closet organization are examples of many upgrades throughout the home. This home also boasts a well water system with a full purification setup, and a laundry room inside with washer, dryer and utility sink included. Beyond the home itself and its many additional upgrades, the Deer Island community offers unparalleled amenities, including a community boat ramp for direct access to John’s Lake — perfect for boating, fishing, and water sports — as well as two catch and release fishponds, basketball courts, tennis courts, pickleball facilities and easy access to the West Orange bike trails. With stunning lake views, lush surroundings, and a true sense of privacy, this is a place where families grow, memories are made, and every day feels like a getaway. Don’t miss the opportunity to own this fabulous home, where elegance meets comfort and lifestyle meets location.
Listing Agent: Karen Jacobs (407-579-0062)
1646 HOLCOMB CREEK ST, WINTER GARDEN, FL 34787
$929,00072 Days on yellowkey MLS ID: O6394506
REDUCED by $20,900 (2.2%) on 04/20/2026
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3841 Built: 2017Monthly Fee: $184 Tax: $12,543 (2025)Community: TwinwatersSingle Family
Taxes:$12,543
Remarks: Welcome to 1646 Holcomb Creek Street. Your beautifully appointed four bedroom, 4.5-bath Meritage home offers 3,824 sq ft of thoughtfully designed living space in one of Winter Garden’s most desirable communities. Built in 2017, this energy-efficient floorplan features spray foam insulation, whole house water filtration system, a spacious open layout, high-end finishes, and multiple flexible living areas. The gourmet kitchen impresses with 42" cabinetry, quartz countertops, stainless steel appliances, extended storage, walk in pantry and a large eat-in dining area. The family room includes an electric fireplace with a floor-to-ceiling stone accent wall and triple sliding glass doors leading to the screened lanai and fenced backyard. The first-floor primary suite offers a tray ceiling and a spa-inspired bath with direct access to the laundry room. A guest suite with private bath, third bedroom with an additional private bath, powder room, and a convenient pocket office completes the main level. Upstairs, a large bonus/game room, additional bedroom, full bath, and a flexible pass-through space provides endless possibilities for a media room, playroom, office or optional 5th bedroom. Your garage offers overhead storage and a Tesla-E/V charger. Exterior features include a tile roof, stone accents, extended front porch, in ground irrigation and lush landscaping. Located minutes from top-rated schools, shopping, dining, major highways and attractions. This exceptional home offers the perfect blend of luxury, comfort, and efficiency—move-in ready and meticulously maintained.
Listing is courtesy of: ERA GRIZZARD REAL ESTATE (407-203-5800)
Listing Agent: Jennifer Grimes (352-223-9588)
14766 ELLINGSWORTH LN, WINTER GARDEN, FL 34787
$1,099,00085 Days on yellowkey MLS ID: O6390518
0 Days Off yellowkey (back on 4/23/2026)
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4661 Built: 2018Monthly Fee: $210 Tax: $14,115 (2025)Community: Oxford ChaseSpa: YesSingle Family
Taxes:$14,115
Remarks: Welcome to this beautifully upgraded 5 bedroom, 4 and a half bath pool and spa home located in the highly desirable, fully gated community of Oxford Chase! Zoned for top-rated schools, this home offers the perfect combination of luxury, privacy, and energy efficiency. This spacious residence features a 3-car garage, paver driveway, and impressive curb appeal. Inside, you’ll find thoughtfully designed living spaces including a formal dining room with a custom built-in bar, perfect for entertaining guests or hosting special occasions, multiple office spaces, upgraded flooring throughout, a large laundry room, private gated doggie retreat, and so much more. The primary suite is located on the first level, secluded for optimal privacy with oversized his and hers closets. Upstairs you'll find guest bedrooms, a large open air loft space, and plush movie theatre room. Step outside to your own gorgeous backyard oasis featuring a fully enclosed heated pool and spa, ideal for year-round Florida living. The backyard overlooks a peaceful green space with no rear neighbors, providing extra privacy and relaxing views. Enjoy outdoor entertaining with the fully equipped summer kitchen featuring a custom vented hood, perfect for grilling and gatherings. The home is also equipped with PAID IN FULL SOLAR PANELS offering incredible energy efficiency and the benefit of little to no electric bill. Located in a secure gated neighborhood close to top schools, shopping, dining, and major highways, this home truly has it all — privacy, premium upgrades, and resort-style outdoor living. Schedule your showing today!
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Jenna Palmero (407-697-8727)
328 BAYSIDE AVE, WINTER GARDEN, FL 34787
$445,00053 Days on yellowkey MLS ID: O6396654
1 Days Off yellowkey (back on 4/23/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1235 Built: 1986Monthly Fee: $7 Tax: $5,354 (2025)Community: Kings BaySingle Family
Taxes:$5,354
Remarks: Under contract-accepting backup offers. Welcome to easy Florida living in this charming 3-bedroom, 2-bath ranch-style home, perfectly positioned on a spacious corner lot in one of Winter Garden’s most desirable areas. With its single-story layout and inviting curb appeal, this home offers both comfort and convenience in a relaxed, open setting. Step inside to discover a bright and functional floor plan designed for everyday living and effortless entertaining. The generous living spaces flow seamlessly, while ample natural light enhances the home’s warm and welcoming feel. The split-bedroom design provides privacy, with a well-appointed primary suite and comfortable secondary bedrooms. Outside, the oversized corner lot offers endless possibilities—plenty of room for outdoor gatherings, gardening, or simply enjoying the Florida sunshine. Located well within the golf cart district, you’re just a short ride from the charm and energy of historic downtown Winter Garden. Enjoy easy access to local shops, dining, community events, and the popular weekly farmers market, all just minutes from your doorstep. This is a rare opportunity to own a beautifully situated home that combines classic ranch-style living with an unbeatable location. Call Today!
Listing is courtesy of: SOUTHERN HERITAGE REALTY, INC (407-877-6928)
Listing Agent: Jim Kernohan (407-450-3861)
64 N PARK AVE, WINTER GARDEN, FL 34787
$1,095,000105 Days on yellowkey MLS ID: O6385285
REDUCED by $54,000 (4.7%) on 04/22/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2225 Built: 2023Monthly Fee: $325 Tax: $15,104 (2025)Community: 30 North ParkTownhouse
Taxes:$15,104
Remarks: Welcome to 30 North Park, an exceptional townhome located in the heart of Historic Downtown Winter Garden — directly on the West Orange Trail and just steps from Plant Street Market, Crooked Can Brewery, local dining, shopping, and the weekly Farmer’s Market. This modern farmhouse-style residence offers four spacious bedrooms, each with a private en-suite bathroom and custom-fitted closets, providing comfort, privacy, and flexibility for guests, multigenerational living, or work-from-home needs. A first-floor bedroom serves as an ideal guest retreat, office, or flex space. The second level features an open-concept living area anchored by a designer kitchen complete with Bosch natural gas appliances, a large island, quartz countertops, farmhouse sink, artisan tile backsplash, and floor-to-ceiling windows showcasing views toward downtown and the West Orange Trail. A secondary bedroom with dramatic custom windows adds abundant natural light. On the third floor, dual primary suites offer spacious layouts, oversized windows, powered blinds, spa-inspired walk-in showers, and quartz-finished baths. Thoughtful upgrades throughout include warm wood flooring, patterned tile accents, modern black lighting fixtures, and extensive storage. Built with an STC soundproofing rating of 69, the home provides a quiet interior environment while remaining in one of Central Florida’s most vibrant walkable districts. Enjoy balcony views overlooking the trail and experience low-maintenance living with unmatched proximity to Historic Winter Garden’s amenities. Experience refined, walkable living in the heart of Winter Garden — schedule your private showing today.
Listing Agent: Steve Healy (407-230-1441)
16669 VARONE COVE CT, WINTER GARDEN, FL 34787
$1,399,900127 Days on yellowkey MLS ID: O6375749
Bed: 7 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 5613 Built: 2016Monthly Fee: $185 Tax: $15,548 (2024)Community: TwinwatersSpa: NoSingle Family
Taxes:$15,548
Remarks: Discover Unmatched Elegance in the Coveted Twinwaters Subdivision! Welcome to your dream home, a breathtaking Winter Garden pool residence built in 2016, offering the perfect fusion of sophistication, luxury, and prime convenience. This property isn’t just a house – it’s your personal sanctuary. Grand Entrance That Stuns: Be greeted by an impressive 14-foot foyer adorned with a dazzling crystal chandelier. A beautifully crafted wooden staircase with iron balusters sets the tone for the home’s elevated style. From the moment you step inside, the open-concept layout invites you to explore spaces designed for both comfort and entertainment. Exquisite Interiors: Every detail exudes elegance. Stunning wood plank accent walls, gleaming 30-inch marble tiles, intricate tray ceilings, and granite countertops throughout create a refined yet warm atmosphere. Whether hosting friends or enjoying quiet family moments, this home is the ultimate setting. First Floor Features: Luxurious Master Suite: Tray ceiling, serene ambiance, and ample space for relaxation. Versatile Guest Suite: Ideal for guests or teens, offering privacy and comfort. Functional Spaces: A large and cozy family room, private office, formal living and dining areas, plus a service pantry with wine storage and a separate laundry room. Gourmet Kitchen: A chef’s paradise with a granite island and seating, deep basin sink, custom 50” solid wood cabinets with glass accents, glass tile backsplash, built-in oven and microwave, and a walk-in pantry. Second Floor Highlights: Expansive Upper Lounge: Large windows fill the space with natural light, making it perfect for relaxation. Bonus Room: Create your dream space—whether a music studio, movie theater, gym, or private office. Second Master Suite: Spacious and serene, with luxurious finishes. Four additional bedrooms, each offering comfort and versatility. Outdoor Oasis: Your backyard is a private paradise! A covered lanai overlooks lush landscaping, a pristine vinyl fence, and a sparkling pool. It’s the perfect retreat for relaxation or entertainment. Modern Conveniences: Solar-powered electricity for energy efficiency Whole-home water purification system Tankless water heater Crown molding throughout Tray ceilings and architectural enhancements that elevate the aesthetic Over 25k in Curtain Work Prime Location & Community Perks: Located in the sought-after Twinwaters community, enjoy access to a community pool and recreation area. Nearby, explore Winter Garden Village, Historic Downtown Winter Garden, Walt Disney World, and top-rated schools. Central Florida’s major highways, shopping, dining, and entertainment are all just minutes away. This home is truly one-of-a-kind.
Listing is courtesy of: FLORIDA CONNEXION PROPERTIES (407-574-2636)
Listing Agent: Tony Bardy Assis (407-796-7777)
2205 WINTERMERE POINTE DR, WINTER GARDEN, FL 34787
$819,000116 Days on yellowkey MLS ID: O6380281
REDUCED by $30,000 (3.5%) on 04/06/2026
Bed: 5 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3747 Built: 2000Monthly Fee: $90 Tax: $10,152 (2025)Community: Wintermere PointeSpa: NoSingle Family
Taxes:$10,152
Elementary School: Lake Whitney Elem
Remarks: Welcome to beautiful Winter Garden. Check out this exceptional 5-bedroom, 3-bathroom home is located in a gated community that blends comfort with a friendly neighborhood atmosphere. Thoughtfully designed, the home features four bedrooms upstairs and a flexible downstairs bedroom ideal for guests or a home office. The spacious primary suite serves as a private escape, complete with a soaking tub, separate shower, and ample room to relax. Upstairs, two expansive loft areas provide endless possibilities—perfect for a home gym, media room, play space, or additional living area. The main level boasts formal living and dining rooms, along with a large family room that opens through sliding doors to a private pool retreat with two paved seating areas, ideal for entertaining or unwinding. An open floor plan, elegant dual-entry wooden staircase, and stainless steel appliances add to the home’s appeal. Offering generous space, charming details, and a peaceful yet convenient location, this home captures the best of Florida living—schedule your showing before it’s gone.
Listing is courtesy of: HP GLOBAL REALTY LLC (407-925-6780)
Listing Agent: Heron Patel (407-925-6780)
14254 SUNRIDGE BLVD, WINTER GARDEN, FL 34787
$1,150,00073 Days on yellowkey MLS ID: TB8489171
Bed: 5 Bath: 3.5 Liv Area Sq Ft: 4004 Built: 2017Monthly Fee: $75 Tax: $11,716 (2025)Community: Cypress Reserve Ph 1Single Family
Taxes:$11,716
Remarks: Presenting this exquisite modern residence standing alone without neighbors in either side or rear in a neighborhood of almost 150 homes showcasing souring ceilings, designer finishes, and an open-concept living space bathed in natural light. A gourmet kitchen that anchors the home, while expansive glass doors reveal a resort-style screened pool and outdoor lounge. Architecture, luxurious details inside all bathrooms and kitchen, and seamless indoor-outdoor living create an exceptional retreat for refined entertaining. An amazingly fancy electric chimney gives the living room area warmth and elegance. AC units are of high efficiency with hotel fragrance throughout the entire home. COME AND SEE IT SOON! AC units is 3 years. New roof to be installed.
Listing is courtesy of: PAULINO GLOBAL REAL ESTATE (407-455-1981)
Listing Agent: Andrea Paulino (813-753-6110)
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