Displaying: For Sale
Location: Winter Garden
Property Type(s): Single Family
Price: $1,000,000+
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Winter Garden - 114 properties found
16826 BROADWATER AVE, WINTER GARDEN, FL 34787
$1,449,000111 Days on yellowkey MLS ID: O6387379
0 Days Off yellowkey (back on 6/9/2026)
REDUCED by $50,000 (3.3%) on 05/29/2026
Bed: 6 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 4451 Built: 2019Monthly Fee: $218 Tax: $9,892 (2025)Community: Waterside/Johns Lk-Ph 1Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$9,892
Elementary School: Hamlin Elementary
High School: West Orange High
Tax Year: 2025
Middle School: Hamlin Middle
Remarks: Under contract-accepting backup offers. Meticulously updated and move-in ready, this stunning residence is located in the highly sought-after gated community of Waterside in Winter Garden. Designed with both luxury and functionality in mind, the home features a desirable first-floor primary suite boasting an expansive en-suite bath with dual sinks and two custom-organized walk-in closets. The main level also includes a guest bedroom with its own full bath, a private office/den, and a convenient powder room. The second floor is an entertainer's dream, offering a massive loft, a Jack-and-Jill suite, and an additional bedroom with a private full bath. Significant upgrades abound, including new dual AC units (2024), rich hardwood flooring (2019), and a modern electric fireplace. Premium features include plantation shutters, custom shelving in the pantry and primary closets, a whole-house water purification system, and noise-blocking insulation for ultimate serenity. Outdoor and tech upgrades feature an extended driveway and an installed Tesla charger. Residents enjoy resort-style amenities including a community pool, fitness center, and clubhouse. Perfectly situated on a prime lot, you are minutes from Winter Garden Village, major highways, and premier shopping and dining. This could be your perfect dream home—schedule your private tour today!
Listing is courtesy of: ONE STOP SERVICE REALTY INC (407-739-3196)
Listing Agent: Ye Kang (321-279-1059)
5526 TINY RD, WINTER GARDEN, FL 34787
$1,590,000320 Days on yellowkey MLS ID: O6334009
3 Days Off yellowkey (back on 6/8/2026)
REDUCED by $85,000 (5.1%) on 06/01/2026
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2474 Built: 2007 Tax: $10,165 (2024)Community: NoneSingle Family
Taxes:$10,165
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Under contract-accepting backup offers. A Rare Slice of Serenity in the Heart of Horizons West — 5526 Tiny Road Almost five acres in the middle of one of Central Florida's most sought-after communities isn't just rare — it's nearly impossible to find. While the rest of Horizons West builds closer together, 5526 Tiny Road sits on almost five rolling, private acres surrounded by open sky, a private pond, and natural Florida landscape — all within walking distance of community trails, top-rated schools, and the brand-new Orange County Library currently under construction just steps away. This is the property buyers spend years waiting for. The freedom of acreage. The convenience of community. No HOA. No compromise. The custom-built 2007 estate offers 2,400 square feet of thoughtfully designed living space — three bedrooms, a spacious loft, and 2.5 bathrooms inside, plus a half bath in the oversized 3.5-car garage built for the enthusiast, the workshop, the toys, or all three. The open-concept layout is filled with natural light, anchored by a gourmet kitchen and flowing living spaces designed for both everyday comfort and effortless entertaining. Step outside and the property truly comes alive. A front gazebo attached to the home frames sweeping views across the acreage. The screened rear lanai overlooks a nature preserve. Sunrises and sunsets paint the elevated ridge in a way that no subdivision lot can replicate. Wild turkeys, native birds, and open Florida sky are your neighbors. Just a short ride to Hamlin Town Center, Disney World, SR-429, and everything Horizons West continues to build around you — including planned road enhancements to Tiny Road itself, with landscaped medians and expanded sidewalks that will further elevate the entrance to this property. Properties like this don't come back to market. Once it's gone, it's gone — because there is nothing left to build like it here. 3 Bed | Loft | 2.5 Bath + Garage Half Bath | 3.5-Car Garage | Almost 5 Acres | No HOA | Custom 2007 Build | Private Pond | Horizons West / Independence-Summerport
Listing is courtesy of: BUYER REBATES REALTY (407-629-2300)
Listing Agent: Sean Popat (407-399-1669)
279 ZACHARY WADE ST, WINTER GARDEN, FL 34787
$1,675,00040 Days on yellowkey MLS ID: O6408014
Bed: 5 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4473 Built: 2003Monthly Fee: $67 Tax: $8,609 (2025)Community: Lakeview ReserveSpa: YesSingle Family
Taxes:$8,609
Elementary School: Tildenville Elem
Middle School: Lakeview Middle
Remarks: An unparalleled lakefront opportunity in Downtown Winter Garden **Seize the rare chance to own a premier waterfront estate where the true value lies in the spectacular lot, private dock, and an enviable golf-cart lifestyle ** Launch your boat from your private lift for a scenic 30-minute cruise to Mt. Dora or take your golf cart just minutes away to the historic downtown Farmers’ Market and restaurants **Positioned within a private, gated enclave directly across from the West Orange Trail, this property offers the ultimate Florida resort lifestyle outside, featuring a heated saltwater pool, raised spa, and a fully fenced, expansive lakeside yard ** Inside, the home boasts a massive primary suite +/16x26’ with tray ceiling, fireplace and a balcony with lovely lake views and massive +/-23x25 bonus room including a wet bar and fireplace** The kitchen has a large cooking island w/sink plus a separate breakfast bar, stone counters, under cabinet lighting, a Jenn-Air double convection oven and lovely dining area overlooking the lake ** There's even an open wine closet/alcove with wine refrigerator off the kitchen ** First floor bedroom with an oversized walk in closet as a 5th bedroom or den (currently being used as a dining room) ** Other home upgrades include a newer roof +/-2022, 3 newer A/C units, a whole-home Katolight 40KW generator that runs +/- 90% of the home, crown molding throughout the home, ADT security system with cameras, boat house with new roof 2025, resurfaced pool +/-5 yrs ago & Aqualink pool/spa automation system and a 10’ seawall ** Relax on the covered screened patio with the Bose speaker system and prime outdoor living space including additional yard space beyond the pool and patio ** 2 car garage plus a 1 car garage with easy access to the back yard perfect for bringing your boat or lawn equipment through ** LOW HOA fees $200 quarterly ** All room measurements in MLS and on 3d floorplan are approximate. Buyer to verify. Tax record is incorrect - property has 5 bedrooms. Dock measurement is estimated. Buyer to verify. Solar panel lease to be transferred to buyer at closing.
Listing is courtesy of: INDEPENDENCE REALTY GROUP LLC (407-408-6662)
Listing Agent: Andrew Philippone (407-408-6662)
16071 BARKLY RIDGE CT, WINTER GARDEN, FL 34787
$1,150,000102 Days on yellowkey MLS ID: O6390569
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2986 Built: 2024Monthly Fee: $225 Tax: $2,420 (2024)Community: Avalon RidgeSingle Family
Taxes:$2,420
Remarks: Enchanting newly built home in Avalon Ridge with a private pool, located in one of the most desirable areas of Winter Garden. This beautiful residence has been thoughtfully designed and features 4 bedrooms with carpet flooring, 3 full bathrooms, and a perfect blend of modern space, functionality, and elegant finishes. The living area features sliding glass doors that open to the outdoor space and private pool, creating the perfect setting for entertainment and relaxation. The spacious living room flows seamlessly into a large kitchen equipped with modern cabinetry, stainless steel appliances, elegant countertops, and a generous center island. The primary suite offers a spacious bathroom with dual sinks, a large walk-in closet, and a comfortable walk-in shower. The three additional bedrooms provide plenty of space for family members or guests. The three-car garage offers ample room for vehicles, storage, or even a workspace. Ideally located in a rapidly growing area, just minutes from major highways, shopping centers, restaurants, and top-rated schools. Don't miss this opportunity—schedule your showing today!
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Jennifer Olmeda (407-547-9242)
15058 SUNSTAR WAY, WINTER GARDEN, FL 34787
$1,900,00025 Days on yellowkey MLS ID: O6411520
0 Days Off yellowkey (back on 6/8/2026)
Bed: 5 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3607 Built: 2021Monthly Fee: $110 Tax: $645 (2025)Community: Highlands/Summerlake Grvs Ph 3Spa: YesSingle Family
Taxes:$645
Elementary School: Summerlake Elementary
High School: Horizon High School
Remarks: Experience LUXURY ~ WATERFRONT LIVING in this FULLY UPGRADED ~ POOL HOME in the sought-after Highlands at Summerlake Groves community of Horizon West! Built in 2021 and situated on a generous .40 ACRE LOT with a FENCED YARD, this exceptional home delivers breathtaking nightly views of DISNEY FIREWORKS reflecting across the water, creating a spectacular backdrop you can enjoy year-round from the comfort of your own home. Designed with both everyday living and unforgettable entertaining in mind, this home offers an OPEN CONCEPT layout filled with natural light, a dramatic two-story living room with a chic FIREPLACE feature wall, CUSTOM BUILT-INS, and WOOD LOOK TILE flooring throughout the main living areas. The spacious MAIN FLOOR PRIMARY SUITE delivers a private retreat, while a dedicated OFFICE with custom built-in cabinetry and desk space makes working from home effortless. Upstairs, you will find three additional bedrooms and one of the home's most impressive features – a PROFESSIONALLY DESIGNED THEATER ROOM with over $350,000 invested in premium finishes and technology, including a $12,000 projector, professional acoustic treatments, custom wall detailing, and seating for eight. No detail was overlooked when it comes to technology and convenience! Whole-home automation controls music, lighting, outdoor fans, LED lighting, water features, and more with the touch of a button. The WHOLE HOME & POOL SOUND SYSTEM further enhances the experience, while the two-car garage includes its own mini-split A/C system. Additional upgrades include a TILE ROOF, water softener, paver driveway, and separate 1-car and 2-car garages offering ample storage and flexibility. Step outside and discover a backyard designed to rival a private resort. The COVERED LANAI features a fully equipped OUTDOOR KITCHEN complete with a built-in grill, pizza oven, stone flat-top grill, vent hood, and oversized ISLAND for gathering. MOTORIZED SHADES provide privacy and comfort, while the CUSTOM POOL & SPA showcase three WATER FEATURES, dramatic FIRE ELEMENTS, and panoramic LAKE VIEWS. A perimeter mosquito misting system helps maintain a comfortable outdoor environment day and night, allowing you to fully enjoy Florida living year-round. Whether you are boating, skiing, entertaining guests, enjoying a movie night in the theater, or watching Disney fireworks dance across the lake each evening, this home offers a lifestyle few properties can match. Residents of the Highlands at Summerlake Groves also enjoy community amenities and a prime Winter Garden location just minutes from Orange County National Golf Center, the New Independence area, Disney parks, shopping, dining, Downtown Winter Garden, farmers markets, community events, and convenient access to SR 429. Waterfront luxury, state-of-the-art technology, unforgettable outdoor living, and one of the most impressive theater rooms you will find in a private residence – this is the opportunity you have been waiting for. Call today to schedule a private tour!
Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)
Listing Agent: Jenny Wemert (407-809-1193)
205 SURPRISE DR, WINTER GARDEN, FL 34787
$1,200,000201 Days on yellowkey MLS ID: O6365188
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2171 Built: 1950 Tax: $3,406 (2024)Community: Winter Garden Shores RepSingle Family
Taxes:$3,406
Elementary School: Dillard Street Elem
Remarks: PRICE ADJUSTED to reflect recent appraisal, this four-lot parcel presents immediate value- with two vacant lots ready for expansion, additional income potential, or future development. Discover an exceptional property in the heart of highly desirable GOLF CART DISTRICT of Winter Garden. Situated on an expansive four-lot parcel totaling 3/4 of an acre, this unique estate offers unmatched space, charm and potential with NO HOA- all within short distance to the 22 mile long West Orange Trail, Winter Garden Farms Market, Plant Street dining, shopping and breathtaking sunsets over Lake Apopka. This beautifully maintained three-bedroom, two-bath home features an office with custom wood built-ins and a light-filled breezeway framed in windows, perfect for a sunroom or additional living space. Gorgeous hardwood floors flow throughout, and the newly renovated bathroom showcases modern, floor-to-ceiling tile for a luxurious touch. Storage is abundant, including an oversized two-car garage with a half bath, ideal for hobbyist or future conversion opportunities. Outside, the property transforms into a private oasis featuring a sparkling heated saltwater pool, outdoor fireplace and lush mature landscaping complete with fruit trees - all fully fenced for privacy. Two of the four lots are currently vacant, offering potential to subdivide, expand, or build. A large shed, rated as a detached garage, on the property provides additional space for a workshop or equipment storage. There is ample room for all your recreational toys; golf-cart, boat, and more. The current owners also have plans for a kitchen renovation and poolside wraparound porch, which they are willing to share with the buyer - opening the door to greater customization. Whether you're seeking a serene retreat, developmental potential, or the charm of downtown Winter Garden living, this property is truly one of a kind. This private paradise location is a convenient commute to Downtown Orlando, Disney and other Orlando attractions. You're dream estate awaits.
Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)
Listing Agent: Alison Scorsone (321-689-3554)
8530 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787
$1,499,00018 Days on yellowkey MLS ID: O6413249
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4130 Built: 2018Monthly Fee: $266 Tax: $2,479 (2025)Community: Waterleigh Ph 1ASingle Family
Taxes:$2,479
Remarks: Rare opportunity to own an exceptional lakefront residence with a private dock and breathtaking panoramic water views in one of Winter Garden's premier resort-style communities. Offering approximately 4,663 square feet of living space, this impressive home features 4 bedrooms, 4 bathrooms, and a 3-car garage on a spectacular direct lakefront homesite. Designed to maximize the stunning waterfront setting, the home showcases soaring ceilings, elegant architectural details, expansive living spaces, and abundant natural light throughout. The gourmet kitchen features an oversized island, double ovens, walk-in pantry, and seamless flow into the main living areas, all positioned to capture beautiful lake views. The luxurious primary suite serves as a private retreat with direct access to a covered second-floor balcony overlooking the water. Additional indoor and outdoor living spaces, including a covered lanai, provide the perfect setting for entertaining or simply enjoying Florida's year-round lifestyle. Residents enjoy access to resort-style amenities including pools, clubhouse, fitness center, walking trails, and playgrounds. Conveniently located near shopping, dining, entertainment, and major roadways, this remarkable waterfront property offers luxury, privacy, and an unparalleled lakefront lifestyle.
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Katherine Perdomo (407-953-2272)
12241 ENCORE AT OVATION WAY, WINTER GARDEN, FL 34787
$1,190,00050 Days on yellowkey MLS ID: O6403198
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3693 Built: 2021Monthly Fee: $225 Tax: $12,882 (2025)Community: Encore/Ovation Ph 1Single Family
Taxes:$12,882
Elementary School: Water Spring Elementary
Middle School: Water Spring Middle
Remarks: Welcome to this stunning 2021-built residence in the highly sought-after Encore at Ovation community in Winter Garden, where modern elegance meets exceptional comfort and thoughtful design. This beautifully upgraded home showcases an open-concept floor plan filled with abundant natural light, soaring ceilings, and exquisite, professionally curated finishes throughout. rom the moment you arrive, you’re greeted by impressive curb appeal, lush landscaping, a charming front porch, and a grand, custom-designed entry hall that sets the tone for the home’s refined interior. Inside, you’ll find designer lighting, including high-end chandeliers and custom pendant fixtures, enhancing both the common and private living spaces. The gourmet kitchen is a true showstopper, featuring next-generation stainless steel appliances, premium cabinetry, stunning stone countertops, a spacious center island, and a large walk-in pantry, perfectly designed for both everyday living and entertaining. The seamless flow into the living and dining areas creates an inviting atmosphere for gatherings of any size. Retreat to the expansive primary suite, where the spa-inspired master bathroom offers a truly luxurious experience with oversized proportions and high-end finishes, complemented by custom-designed closets. Additional bedrooms are generously sized, offering flexibility for guests, a home office, or multi-generational living. This home also features a spacious loft, an oversized laundry room, and beautiful flooring throughout with no carpet, providing both style and easy maintenance. Step outside to your private backyard oasis, designed for unforgettable moments. Enjoy a covered summer kitchen complete with modern features and a cozy fireplace, perfect for barbecues and al fresco dining. The breathtaking pool and spa, enhanced by elegant landscaping and design, create a resort-style ambiance. A fire pit gathering area and outdoor shower complete this exceptional space, your guests may never want to leave. Additional highlights include a Tesla charger, solar panel system for significant energy savings, and a garage equipped with storage racks and ample space. Situated on a premium lot, this home truly offers it all. Ideally located near top-rated schools, shopping, dining, and major highways, and just minutes from Walt Disney World and Orlando’s world-class attractions, this move-in-ready masterpiece delivers the perfect combination of luxury, efficiency, and prime location.
Listing Agent: Any Alves (407-455-0618)
15326 JOHNS LAKE POINTE BLVD, WINTER GARDEN, FL 34787
$1,385,00025 Days on yellowkey MLS ID: S5150851
1 Days Off yellowkey (back on 6/5/2026)
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3495 Built: 2014Monthly Fee: $128 Tax: $7,670 (2025)Community: Johns Lake PointeSpa: YesSingle Family
Taxes:$7,670
Elementary School: SunRidge Elementary
Middle School: SunRidge Middle
Remarks: Under contract-accepting backup offers. Welcome to luxury lakefront living on the shores of sought-after Johns Lake. Perfectly positioned with breathtaking west-facing sunset views, this fully upgraded waterfront residence offers the ultimate blend of elegance, comfort, and resort-style outdoor living in one of Winter Garden’s most desirable communities. Featuring nearly 3,500 square feet on 1 floor of thoughtfully designed living space, this exceptional home showcases 4 bedrooms, 3.5 bathrooms, a 3-car garage, premium hardwood flooring, and a gourmet chef’s kitchen with high-end finishes, upgraded cabinetry, and expansive entertaining space. Designed to maximize the waterfront lifestyle, the home seamlessly transitions outdoors to a private backyard retreat complete with a sparkling pool, oversized spa, outdoor kitchen, and stunning panoramic lake views — the perfect setting for sunset entertaining year-round. Additional highlights include a newer roof and HVAC systems (approximately 3 and 5 years old), luxurious updated interiors, spacious living areas. This rare Johns Lake opportunity combines elevated style with effortless move-in-ready convenience. With premium designer furnishings negotiable. Making this a possible true turnkey opportunity. Located within the highly sought-after Johns Lake Pointe community, residents enjoy proximity to historic downtown Winter Garden, top-rated schools, shopping, dining, major highways, and Orlando’s world-class attractions. Experience the best of Central Florida lakefront living in a home where every evening ends with unforgettable sunsets over Johns Lake.
Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)
Listing Agent: Carlos Facchinat (407-433-8109)
16746 TURTLE HATCH DR, WINTER GARDEN, FL 34787
$1,265,00034 Days on yellowkey MLS ID: O6406556
1 Days Off yellowkey (back on 6/6/2026)
Bed: 6 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4451 Built: 2018Monthly Fee: $215 Tax: $9,540 (2025)Community: Waterside/Johns Lk-Ph 1Single Family
Taxes:$9,540
Remarks: Behind the gates of the Waterside community in Winter Garden, this exceptional residence offers a rare blend of luxury, thoughtful design, and modern functionality. Built in 2018, this beautifully upgraded 6 bedroom, 4.5 bathroom home spans 4,451 square feet and includes a spacious 3 car garage, all positioned within one of Winter Garden’s most desirable gated communities. From the moment you enter through the charming front courtyard entrance, the home showcases refined finishes, expansive living spaces, and an open concept layout designed for both everyday comfort and upscale entertaining. A dramatic two story entry and soaring two story great room create an impressive first impression, while abundant natural light pours throughout the home enhancing the warm yet elegant atmosphere. Additional architectural details including crown molding, tray ceilings, and elegant rod iron stair railings further elevate the design. The gourmet kitchen serves as the centerpiece of the home featuring quartz countertops, a designer tile backsplash, vent hood, gas range, double convection ovens, oversized island, abundant cabinetry, built-in desk area, and an expansive eat in kitchen area ideal for both casual dining and entertaining family and guests. The thoughtfully designed first floor features a spacious primary suite highlighted by tray ceilings, ceiling fan, dual walk in closets, and a spa inspired ensuite bathroom complete with dual sinks, granite countertops, garden tub, and a luxurious walk-through shower with dual shower heads. A private guest suite with its own ensuite bath and tile glass enclosed walk in shower offers the perfect setup for visitors or multi generational living. A dedicated office with double door entry, elegant formal dining room with tray ceiling, expansive great room, convenient half bath, and exceptional storage throughout further enhance both the functionality and sophistication of the home. Upstairs, the second floor features four additional bedrooms, two additional bathrooms, and a spacious bonus room with double door entry complete with a private balcony overlooking the backyard, creating the perfect retreat for entertaining, relaxing, or family gatherings. Outdoor living is equally impressive with a covered rear patio featuring pavers and ceiling fan, offering the perfect place to relax or entertain while enjoying the privacy of having no rear neighbors. The property also offers ample space to create your dream pool and outdoor entertaining area. Additional highlights include a tankless water heater, window blinds throughout, crown molding, and the home is prewired for a future outdoor kitchen. Neighborhood amenities include a community pool, recreational facilities, and playground. Located within gated Waterside, residents enjoy a private and exclusive atmosphere while remaining just minutes from top rated schools, shopping, dining, Disney, downtown Winter Garden, and major roadways including the 429, Turnpike, and 408. This is more than a home, it is a lifestyle defined by space, craftsmanship, privacy, and location in one of Central Florida’s premier communities
Listing is courtesy of: CLOCK TOWER REALTY (407-832-7332)
Listing Agent: Jennifer Mitchell (803-414-1133)
1651 AMSEL FALLS PARK TER, WINTER GARDEN, FL 34787
$1,080,00018 Days on yellowkey MLS ID: O6414027
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3881 Built: 2017Monthly Fee: $184 Tax: $6,540 (2025)Community: TwinwatersSingle Family
Taxes:$6,540
Remarks: Welcome home to this beautifully maintained 4-bedroom, 3 full bath, residence in sought-after Twinwaters. Featuring a designer kitchen with full-extension soft-close drawers and cabinets, 10-foot ceilings on the main level, 9-foot ceilings upstairs, crown molding, and central vacuum, this home offers both comfort and thoughtful upgrades throughout. Enjoy peaceful views of the expansive conservation area from your backyard with no rear neighbors, creating a private and relaxing setting. Professionally designed landscaping provides year-round color and fragrance, while local songbirds add to the natural charm. On clear evenings, catch a glimpse of Disney fireworks from home. Conveniently located just minutes from historic Downtown Winter Garden, shopping, dining, and premier golf destinations including Orange County National. Complete with a spacious 2-car garage, this warm and inviting home is ready for its next owner. Schedule your private showing today!
Listing is courtesy of: FOLIO REALTY LLC (407-917-0241)
Listing Agent: Jennifer Dollar (407-252-3762)
20 E DIVISION ST, WINTER GARDEN, FL 34787
$1,149,00018 Days on yellowkey MLS ID: O6413659
Bed: 4 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2729 Built: 1959 Tax: $7,197 (2025)Community: Winter Garden Shores First AddSpa: NoSingle Family
Taxes:$7,197
Remarks: Welcome to one of Winter Garden's most remarkable custom transformations. This wasn't a flip—it was the owner's forever dream home. Originally built in 1959 and completely reimagined in 2023 and 2026. This extraordinary residence has undergone an extensive renovation and expansion, creating a truly one-of-a-kind property just minutes from Historic Downtown Winter Garden and Plant Street. Offering 2,729 square feet of beautifully designed living space, this 4-bedroom, 3-bathroom home showcases exceptional craftsmanship, thoughtful design, and luxury finishes throughout. In 2026, the owners completed a stunning expansion that includes an ultra-luxury primary suite designed as a private retreat. The spa-inspired custom bathroom features premium finishes, a private sauna, and a level of comfort rarely found at this price point. The heart of the home features open-concept living spaces filled with natural light, designer finishes, and seamless flow for everyday living and entertaining. Step outside to your private backyard oasis featuring a brand-new custom pool completed in 2026, creating the perfect setting for relaxing weekends and unforgettable gatherings. Major improvements include a 2026 HVAC system, 2026 luxury primary suite addition, 2026 custom pool, 2022 plumbing, 2022 electrical, 2018 roof, and all new windows installed in 2018, providing peace of mind for years to come. Every inch of this home tells the story of a family who spared no expense creating their dream home. Now, that dream can become yours. Schedule your private showing today!!!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Liz Boyce (407-784-4919)
3208 SAILING PIER AVE, WINTER GARDEN, FL 34787
$1,049,90059 Days on yellowkey MLS ID: O6402332
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3998 Built: 2023Monthly Fee: $208 Tax: $12,135 (2024)Community: Ests/Lakeview PreserveSingle Family
Taxes:$12,135
Remarks: Welcome to 3208 Sailing Pier Ave, the original model home at The Estates at Lakeview Preserve. Built in 2023, this stunning residence offers 5 bedrooms, 4 bathrooms, and nearly 4,000 square feet of living space. It is being sold fully furnished with designer-selected pieces, representing turnkey luxury at its finest. The first level features an open-concept layout filled with natural light, a chef-style kitchen with quartz countertops and a walk-in pantry, a spacious living and dining area, a private flex room, and a serene and elegant primary suite. Two additional bedrooms are also located on the first floor. The second level offers a second living area, two more bedrooms, and a beautifully furnished family/game room, perfect for entertaining and relaxing. As a former model home, every detail was professionally designed, and all furnishings are included. The expansive backyard provides the perfect space to create your dream outdoor oasis. Located in the gated community of Estates at Lakeview Preserve, residents enjoy resort-style amenities including a pool, clubhouse, fitness center, playground, and scenic lakeside trails. The home is just minutes from SR-429, Disney, Winter Garden Village, and top-rated schools. Move-in ready and meticulously maintained, this home offers exceptional style, convenience, and value. Schedule your private showing today.
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Mireille Stewart (786-553-6246)
241 N DILLARD ST, WINTER GARDEN, FL 34787
$1,499,999246 Days on yellowkey MLS ID: O6353975
REDUCED by $100,001 (6.3%) on 04/13/2026
Bed: 4 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. Set on a lot boasting an expansive 214 feet of frontage, a rare and highly sought after feature that enhances both privacy and presence. 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)
16783 TURTLE HATCH DR, WINTER GARDEN, FL 34787
$1,199,99946 Days on yellowkey MLS ID: O6404708
0 Days Off yellowkey (back on 6/5/2026)
REDUCED by $1 (0.0%) on 05/20/2026
Bed: 5 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3513 Built: 2019Monthly Fee: $240 Tax: $13,161 (2025)Community: Waterside/Johns Lk-Ph 1Single Family
Taxes:$13,161
Elementary School: Whispering Oak Elem
Remarks: An exceptional expression of refined living, this luxury estate is nestled within the exclusive gated enclave of Waterside at Johns Lake in Winter Garden. Boasting 5 bedrooms and 5.5 baths, this impeccably designed residence showcases a seamless blend of sophistication and comfort. The expansive open-concept layout is enhanced by elegant wood plank tile flooring throughout the main level and anchored by a chef-inspired gourmet kitchen, thoughtfully appointed for both everyday living and upscale entertaining. The lavish primary suite serves as a private sanctuary, featuring a spa-caliber bath and an oversized walk-in closet designed to impress. Step outside to your own resort-style retreat, where a screened-in pool and spa create the perfect setting for relaxation, complete with a dedicated pool bath for added convenience. The upper level offers a versatile bonus room along with a private guest suite, providing ideal accommodations for visitors or multigenerational living. Distinguished features include a 3-car garage, stately slate tile roof, charming courtyard entry, and a fully integrated irrigation system—every detail curated for both elegance and ease. Residents enjoy access to an array of resort-style amenities, including a clubhouse, state-of-the-art fitness center, community pool, fishing dock, scenic walking paths, parks, and playgrounds. Perfectly positioned just minutes from the charm of Historic Downtown Winter Garden, Winter Garden Village, Hamlin, and Horizon West, with convenient access to major thoroughfares and Central Florida’s premier attractions
Listing is courtesy of: SIERRA REALTY GROUP LLC (407-557-3119)
Listing Agent: Sylvester Harding (407-557-3119)
12904 WESTHAVEN OAK DR, WINTER GARDEN, FL 34787
$1,032,000132 Days on yellowkey MLS ID: O6381734
0 Days Off yellowkey (back on 6/1/2026)
INCREASED by $10,000 (1.0%) on 06/01/2026
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3894 Built: 2026Monthly Fee: $77 Tax: $2,326 (2025)Community: Westhaven At OvationSingle Family
Taxes:$2,326
Remarks: Under Construction. Under Construction. Toll Brothers New Construction in Horizon West – Winter Garden | Estimated Completion Summer 2026 The wide and elongated foyer create an impressive entry into this home, with large formal dining room and spacious kitchen. The well-equipped kitchen features a walk-in pantry and an open view of the breakfast area and great room. The great room opens out to a covered lanai. The master bedroom/ on the second floor includes a large walk-in closet and a private bath with a free-standing tub, a separate shower with a seat, and a private toilet area. The second floor features a spacious loft, and large secondary bedrooms. The Griffin is well planned for a comfortable, luxurious lifestyle. Model home available for walkthrough.
Listing is courtesy of: ORLANDO TBI REALTY LLC (407-345-6000)
Listing Agent: Dayene Grubert (863-521-4474)
156 STANTON ESTATES CIR, WINTER GARDEN, FL 34787
$1,149,950110 Days on yellowkey MLS ID: O6384801
REDUCED by $50,050 (4.2%) on 06/03/2026
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3170 Built: 2018Monthly Fee: $188 Tax: $7,979 (2024)Community: Stanton EstatesSingle Family
Taxes:$7,979
Remarks: **We've just introduced a significant price reduction, creating an exceptional opportunity for new owners. ** **Welcome to Golf Cart Life in Historic Downtown Winter Garden** Nestled within Stanton Estates — an exclusive enclave of just 45 luxury homes — this contemporary masterpiece places you in the heart of **Winter Garden’s vibrant Golf Cart District**, where every day feels like a getaway. Built in 2018, this one-story multigenerational estate offers 3,170 sq ft of refined living on a nearly 1/3-acre lot, just a quick golf cart ride from **Plant Street’s award-winning restaurants, live music, boutique shops, the famous Saturday Farmer’s Market, the Crooked Can Brewery, and the scenic West Orange Trail**. Take a look at Virtual Tour Link 2 to see all the exciting and fun things available to you in the downtown and historic area of Winter Garden. Inside, soaring 12-ft ceilings and natural light flow through an open, flexible layout with four bedrooms, four full baths, and a private office. The gourmet kitchen anchors the home with solid wood cabinetry, quartz countertops, an oversized island, walk-in pantry, and a full suite of KitchenAid Professional appliances with natural gas. The primary suite features a recessed ceiling, expansive custom walk-in closet, and a spa-inspired bath. Fully retractable sliders open to a covered lanai surrounded by mature, professionally designed landscaping and privacy fencing — your own private Florida retreat after a day of exploring downtown. Premium upgrades include smart-home technology, motorized shades, whole-home water filtration, 8-ft solid core doors, custom cabinetry, a three-car tandem garage with brick paver driveway, and a brand-new tankless gas water heater (2025). Just minutes from Disney, Universal, and SeaWorld, with seamless access to SR-429, the Turnpike, and 408, this address blends luxury living with the unbeatable charm and excitement of Downtown Winter Garden. Opportunities like this in Stanton Estates are rare. **Welcome to the lifestyle everyone wants**
Listing is courtesy of: FATHOM REALTY FL LLC (888-455-6040)
Listing Agent: Joe Thomas, Jr (813-724-1922)
16161 BARKLY RIDGE CT, WINTER GARDEN, FL 34787
$1,690,00054 Days on yellowkey MLS ID: O6402785
REDUCED by $110,000 (6.1%) on 06/03/2026
Bed: 6 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 5284 Built: 2024Monthly Fee: $225 Tax: $2,826 (2025)Community: Avalon RdgSpa: NoSingle Family
Taxes:$2,826
Remarks: Sunset Lake Views | Luxury Upgrades | Move in Ready | Positioned on a Cul-de-Sac homesite with unobstructed views of Lake Avalon, this six-bedroom residence offers a functional two-level layout. Built in 2024 and enhanced with extensive owner improvements completed after purchase. The main floor supports single-level living with a primary suite, guest bedroom with en-suite bathroom, study, and an extensively upgraded kitchen and butler’s pantry featuring an oversized 10’ x 7’ island, quartz countertops, stacked cabinetry, dual Bosch dishwashers, Thermador microwave, and Samsung appliances. New luxury vinyl flooring extends throughout the first level, complemented by 12-foot ceilings. The primary suite features tray ceilings, automatic blinds, a large walk-in closet, and a remodeled bath with floor to ceiling tile and seamless glass shower. Upstairs includes a 33x22 loft, media room, four additional bedrooms, climate-controlled storage, and a balcony with elevated lake views. Other recent updates include interior paint, lighting, and gutters. Community amenities include a recreation area and walking trails, with convenient access to the 429, downtown Orlando, Walt Disney World, and top-rated schools.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Renee Funk (407-559-8596)
440 TIERRA VERDE LN, WINTER GARDEN, FL 34787
$1,200,00022 Days on yellowkey MLS ID: O6412260
Bed: 4 Bath: 3.0 Gar: 4 Liv Area Sq Ft: 3512 Built: 2004Monthly Fee: $94 Tax: $5,135 (2025)Community: Lake Cove Pointe 46/58Single Family
Taxes:$5,135
Remarks: LOCATION, Location, Location! This Custom-Built builder’s home of 4 bedrooms, flex room, and 3 bathrooms, is located in the beautiful, gated community of Lake Cove Pointe, Winter Garden, Florida. Just jump in your golf cart or simply walk to the forever growing and amazing downtown Winter Garden. The pavered driveway leads to a four-car tandem, oversized garage with (oversized) 18 and 10 feet garage doors. As you enter the 3512 living sq. ft. brick front home, you will be welcomed into a large foyer that overlooks the spacious, open-concept floor plan that is appealing for family and entertaining guests. The dining room is an eye catcher with its double-tray ceiling and surrounding, accented, large columns. Double French doors lead into the oversized living room. The open family room features a gas fireplace and triple sliding doors that lead to the large brick, enclosed patio. The breakfast nook area, which is open to your incorporated view, has an accented bay window. All windows throughout the house are new and have plantation shutters. The large, upgraded kitchen comes with a huge snack bar, center island, double ovens and granite counter tops. The primary bedroom has a tray ceiling and a sitting area. The bathroom features a built-in oval shaped bathtub, a separate shower and double sinks. The roof is 4 years old. Extra storage and closet space. Extra washer and dryer in guests’ side of house. Primary laundry room has wood cabinets, stainless steel sink, and built-in ironing board. The guest area of the house has pre-wiring and pre-plumbing to easily convert into a Mother-in- Law Suite. Don’t miss out seeing this one of a kind builders home today
Listing Agent: Jerry Osser (321-624-5133)
15047 GAULBERRY RUN, WINTER GARDEN, FL 34787
$1,525,00038 Days on yellowkey MLS ID: O6408283
1 Days Off yellowkey (back on 5/31/2026)
Bed: 5 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4964 Built: 2013Monthly Fee: $198 Tax: $10,739 (2026)Community: Signature Lks-Pcl 01D Ph 02Single Family
Taxes:$10,739
Elementary School: Independence Elementary
Tax Year: 2026
Middle School: Bridgewater Middle
Remarks: Under contract-accepting backup offers. This is the one you’ve been waiting for! Tucked away on a peaceful cul-de-sac and situated on an expansive half-acre corner lot, this stunning Horizon West home, in the highly sought-after community of Independence, offers exceptional curb appeal, privacy and luxury living at every turn. Inside, experience soaring, double-height ceilings and an abundance of natural light that fills the spacious, open-concept living area. The thoughtfully designed floor plan features a private office, a formal dining room and an oversized main living space with incredible two-story ceilings and breathtaking views of the resort-style pool and outdoor entertaining areas. At the heart of the home is the chef’s kitchen, complete with extensive cabinetry and storage, a large center island and top-of-the-line stainless steel appliances, perfectly designed for both everyday living and entertaining. The spacious owner’s suite is a true retreat, featuring custom walk-in closets and a spa-inspired bath designed for relaxation. An additional main-level living space offers incredible flexibility and can easily serve as a private guest retreat or multigenerational living suite. Upstairs, entertainment takes center stage with a spacious bonus and playroom, an included pool table and an impressive, dedicated private home theater, featuring luxury powered seating for eight with a built-in projector and amazing quality in-wall surround sound for the ultimate movie-night experience. Outside, enjoy your private backyard oasis. The inviting and refreshing oversized pool showcases a stone wall spillover water feature and Baja sun shelf, all surrounded by lush landscaping for added privacy. The expansive lanai offers two separate seating areas, plus a natural gas fire pit and outdoor kitchen, creating the perfect setting for family fun and entertaining. Beyond the pool area, you’ll find more than 2,000 square feet of private, fenced backyard space with lush grass, shaded by mature trees, ideal for play, pets or relaxing outdoors. Additional upgrades include an oversized, three-car garage plus workspace, a dependable, powerful 20-kilowatt-hour Kohler whole-house generator, two tankless water heaters, a newly-upgraded HVAC and pool equipment and newer pool solar panels, all offering added efficiency and peace of mind. In a community known for its beautiful lake views, incredible scenery and abundant natural wildlife, this home also offers nightly views of Disney fireworks, spectacular sunsets over Lake Hancock and unforgettable rocket launches, all from inside and around this beautiful home. Experience this incredible home in the ideal location for yourself, and discover luxury living at its finest.
Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-333-1900)
Listing Agent: Lynda Miller (407-620-2924)
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