Winter Garden, Florida listings for sale

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$1,575,000 - Winter Garden, FL
9019 Tower Pine Drive Winter Garden, FL - *Video and 3D Tour Available! * Bring the horses! This 5-acre lot has not only a beautiful home, but room for the horses to run and live comfortably in your back yard. The home is situated at the end of quiet Tower Pine Dr. and is FULLY FENCED. The fresh landscaping and circle driveway greet you when you pull through the gate. This home has formal living and dining rooms as well as an open concept between the kitchen and the family room. You’ll find tile floors throughout and new carpet in the secondary bedrooms. CROWN MOLDING, a stone accented WOOD-BURNING FIREPLACE and French doors to the pool make this living space warm and inviting! Make your favorite dishes in the eat-in GOURMET KITCHEN with a double built-in oven, induction cooktop, granite countertops, large island, and walk-in pantry. Movie night is calling from the MEDIA ROOM with the BOSE SURROUND SOUND, screen and projector. The spacious primary bedroom has FRENCH DOORS to the patio, 2 walk-in closets, dual vanities and dual shower heads. The front bedroom has a PRIVATE BATH while the 3rd and 4th bedrooms share a hall bath. There is a large laundry room with utility sink and EXTENDED 3-CAR GARAGE. Enjoy the sunsets from the SCREENED PATIO and cool off in the SALT-WATER POOL. The HEATED SPA and rock feature also have WATERFALLS. Outside you’ll find a 3-STALL BARN with a 30x30 turnout, an 18x12 FEED & TACK ROOM, and a 12x12 WASH STALL with rubber mats. There are 2 fenced and cross-fenced PASTURES attached to the 80x120 ARENA with a clay footing and sand topper. The SCREEN ROOM is just waiting for you with a hot tub and room for a tiki bar! There’s a TRACTOR/STORAGE BARN and an 18x24 SHED to keep you organized! Additional upgrades in the home include a NEWER ROOF (2021), blown-in insulation (2024), gutters, irrigation and landscape lighting plus there are ceiling fans throughout the property. Don’t miss your chance to make this one your own!
2002 | 4 | 3 | 4,910 sqft.
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$1,565,000 - Winter Garden, FL
108 Stanton Estates Circle Winter Garden, FL - Welcome to 108 Stanton Estates Circle, a beautifully crafted 4-bedroom, 4-bath pool home offering over 4,200 square feet of refined living in the heart of one of Winter Garden’s most charming communities. Located in Stanton Estates, a quiet neighborhood of fewer than 50 homes, this property sits just one block from the West Orange Trail and within Winter Garden’s golf cart district, offering effortless access to Plant Street Market, Crooked Can Brewery, local events, and the award-winning downtown scene. Step through the grand two-story foyer and be welcomed by a striking wrought iron staircase, wood-look tile flooring, and warm, timeless finishes. The open-concept kitchen boasts a massive quartz island, stainless steel appliances, a walk-in pantry, and flows seamlessly into the main living area, perfect for entertaining or relaxing at home. Off the living room, a flex space with modern farmhouse doors offers versatility as a home office, playroom, or formal dining room. The first-floor primary suite includes a frameless glass shower, dual vanities, and an expansive walk-in closet. Upstairs, a spacious loft opens to a private balcony overlooking the backyard and pool, the perfect spot for morning coffee or unwinding in the evening. One of the three upstairs bedrooms functions as a secondary primary suite, complete with its own en-suite bath, offering an ideal setup for multi-generational living or long-term guests. The backyard is your personal oasis, featuring a pool with sun shelf, low-maintenance turf, and a covered lanai ready for year-round enjoyment. An oversized paver driveway and 3-car garage complete this exceptional home. This is the rare opportunity to own a thoughtfully designed, move-in ready home in one of Central Florida’s most walkable, vibrant, and community-focused neighborhoods.
2019 | 4 | 4 | 4,212 sqft.
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$1,550,000 - Winter Garden, FL
7833 Freestyle Lane Winter Garden, FL - Sellers are motivated and will consider ALL offers! Pool designs available! - A sprawling single story, meticulously maintained home nestled within the highly sought after Isles of Lake Hancock. This gated, waterfront community sits just minutes from Disney, holding a masterful open floor plan that greets all with an colorful artistic atmosphere, modern home tech features, flawless appliances, and upgrades fit for the ideal Florida lifestyle. The home is tailored with an abundant inspiration of imported contemporary Art, Metals, Glass, and upscale lighting design while sitting in a premier Horizon West gated community. Step foot into an opulent main foyer space and feel the interior sophistication in every direction, which extends into the formal dining room, office, kitchen and main living room. Complimenting Luxury Tile, and Engineered Hardwood floors accompany the Dark Custom Cabinetry, Glass Metallic Backsplash, and flawless Stainless Steel Appliances throughout the kitchen. Lofty 14-foot Double tray ceilings surround the entirety of the home, and 10ft ceilings with remote controlled invisible/retractable blade ceiling fans can be found in each secondary bedroom. The Primary bedroom is perfectly separated from all secondary bedrooms is comfortably designed around the Oversized Spa Bath and Walk in Shower, and a moody Custom designer Closet and storage. A spacious extended den area which also provides access to the exterior outdoor deck, acts perfectly as a reading room or lounge space in the morning. Enjoy masterful Interior and Exterior Entertainment choices such as two massive Theatre/Streaming Projectors, Overhead Outdoor Heating Unit, Electric Fireplace, Luxury LED Lighting Fixtures, Designer Home Entertainment Cabinetry, and Electric Screen Door Enclosure. Flawless Smoke Grey Epoxy floors lines the garage, and along with custom ceiling storage overhead cabinetry, and spacious room car lift capability. With direct access into two man-made lakes, this prestigiously known neighborhood acts as one of central Florida’s Premeir Water Skiing destinations, holding world class ski tournaments annually. The artistic, detailed, and meticulously maintained features of this home fill it with warmth and good energy. This statement piece home and its affluent upgrades and details are felt in every space, making this a must see Winter Gardens single story residence!
2018 | 4 | 3 | 3,364 sqft.
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$1,499,000 - Winter Garden, FL
16669 Varone Cove Court Winter Garden, FL - 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 and won’t stay on the market long. Schedule your private tour today and experience the unparalleled lifestyle that awaits!
2016 | 7 | 5 | 5,613 sqft.
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$1,495,000 - Winter Garden, FL
10139 Austrina Oak Loop Winter Garden, FL - Welcome to 10139 Austrina Oak Loop! Featuring SIX BEDROOMS PLUS OFFICE and FIVE FULL BATHS, on a premium one-third acre lot overlooking the Disney preserve with a HEATED SALTWATER POOL AND SPA under a screen enclosure, this beautifully upgraded home is 4,500 square feet of understated elegance. With no front neighbor, step back to take in the impressive façade, paver drive and custom landscaping. Across the foyer from the formal dining room, French doors lead to the private office / seventh bedroom with an adjoining full bath. The gourmet kitchen and butler’s pantry feature quartz countertops, stainless appliances including double ovens, 42-inch cabinets with bonus overhead cabinets, an oversized island, and a walk-in pantry, all under the glow of custom light fixtures. A triple-pane sliding door with motorized blinds overlooks the pool and illuminates the family room, with ten-foot ceilings and luxury vinyl plank floor. Around the corner is the first floor Owner’s Suite, with tray ceiling and separate pool access, plus a large Owner’s Bath with two quartz vanities, soaking tub with separate shower and a huge walk-in closet. Upstairs, a wet bar with granite counter opens into a spacious loft with separate bonus room, adjacent to an en suite bedroom with full bath and walk-in closet. A tour of the large secondary bedrooms reveals plentiful natural light, walk-in closets, and views of the pool and wooded area beyond. Outside, a paver deck surrounds the heated saltwater pool and spa – all enclosed in an oversized screen enclosure offering uninterrupted views of nature by day and Disney fireworks by night. This immaculately maintained is completely move-in ready with custom window treatments, fully fenced lot, rain gutters and much more. This home is walking distance to top rated schools, retail, and dining at The Mark, and offers easy access to area attractions and the FL-429 corridor. Contact us now to schedule a private showing of this beautiful home!
2019 | 6 | 5 | 4,493 sqft.
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$1,495,000 - Winter Garden, FL
9574 Meadow Hunt Way Winter Garden, FL - NEW PRICE | Experience luxury living in this immaculate, semi-custom home within Watermark at Horizon West. Built by Meritage Homes, the Lafayette sits on over a quarter acre combining breathtaking water and preserve views with modern elegance. Nestled in tranquility, this 5-bedroom, 3 full and 3 half-bath masterpiece is designed for those who love to entertain and enjoy life's finest comforts. Step inside to discover a seamless blend of style and functionality. Wander through the sweeping foyer to a gourmet kitchen, complete with a stunning granite island and stainless-steel appliances, perfect for culinary adventures. The 2-story family room, bathed in natural light, opens to a resort-style oasis featuring a heated, automated saltwater pool and a full outdoor kitchen with a BBQ grill, all set against serene water and conservation views. Retreat to the first-floor primary suite, a sanctuary offering soaking tub, separate walk-in shower, dual vanities, and a custom closet. The spacious upstairs loft and bonus media room cater to work and play, while every bedroom promises privacy with walk-in closets and Jack-and-Jill baths. Outside, enjoy evenings by the gas firepit or entertain under the stars with an upgraded sound system. The newly enhanced garage features a workshop and ample storage, perfect for the modern homeowner. This home, freshly painted in 2020, offers an unparalleled lifestyle, blending comfort and sophistication. Why wait to build, when your dream home awaits? Embrace the extraordinary today.
2017 | 5 | 4 | 4,340 sqft.
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$1,449,999 - Winter Garden, FL
7515 John Hancock Drive Winter Garden, FL - Perfectly situated within Winter Garden’s premier community - Overlook at Hamlin - this exceptional home offers stunning WATER VIEWS from almost every room, exquisite HARDWOOD FLOORS in a fresh modern tone, a chef’s dream GOURMET KITCHEN, dedicated HOME THEATER complete with SURROUND SOUND, DUAL PRIMARY SUITES (one up/one down!), a 75 YEAR CLAY TILE ROOF for peace of mind for years to come - plus formal, family and flex spaces, RESORT STYLE AMENITIES and access to beautiful LAKE HANCOCK! No detail was overlooked and you will notice that in the many thoughtful UPGRADES and you tour this dream floor plan of 6 SPACIOUS BEDROOMS, 5 FULL LUXURIOUS BATHS and 1 convenient half bathroom. The main floor delivers must-see formal spaces flanking the foyer; a two story living room perfect for hosting guests and across the way a formal dining space adorned in crown molding and finished with a wood slat ceiling. Follow the natural flow into a light and bright family room courtesy of the TRIPLE SLIDING GLASS DOORS that open up to the large screened lanai for ideal indoor/outdoor living and sweeping views of the pond. The family room is open to a kitchen that feels like its been ripped out of the pages of a home magazine with stylish floor to ceiling shaker style cabinetry, sleek stone countertops, DUAL ISLANDS for prep and casual bar seating, desirable STAINLESS STEEL APPLIANCES that include a GAS STOVE, and a WALK-IN PANTRY for ample storage. There are two bedrooms on the main floor; a guest bedroom with a private en-suite bath and your MAIN PRIMARY SUITE. A tranquil escape from the day this space seamlessly blends style and luxury with the upgraded finishes, DUAL WALK-IN CLOSETS and a spa-like en-suite bath that includes a dual sink vanity under decorative mirrors, SOAKING TUB and large separate glass enclosed shower. Upstairs you will find flexible spaces for room to grow in the BONUS/LOFT and theater room, plus three more guest bedrooms and a second primary suite giving you options for overnight guests or visiting in-laws. For the car and hobby enthusiast there is an expansive 3-CAR GARAGE, side facing and paired with immaculate landscaping for unparalleled curb appeal. Owning a home in this vibrant and active community means living the lake life with a resident only COMMUNITY BOAT RAMP and dock on Lake Hancock, swimming in the RESORT-STYLE POOL and enjoying an array of other amenities that include a splash pad, clubhouse, fitness center, community events and so much more! Enjoy views of Disney fireworks nightly from home or spend the day exploring the parks. Zoned for A-RATED SCHOOLS, and you are also just minutes from Hamlin Town Center, shopping, dining, attractions and major roadways like the 429 for anywhere you need to go. Built in 2019 and decked out in tons of upgrades, this home FEELS LIKE NEW and is ready for you to move right in. Call today to schedule a tour and fall in love with your new HOME SWEET HOME in one of the most sought-after areas of Winter Garden!
2019 | 6 | 6 | 4,816 sqft.
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$1,449,000 - Winter Garden, FL
682 Canopy Estates Drive Winter Garden, FL - Welcome to this exceptional estate in **Canopy Oaks**, a prestigious **gated and virtual guarded community** recognized as one of *Orlando’s Top Ten Communities*. This **4-bedroom, 4.5-bath, 3-car garage** home features the acclaimed *Sanibel floorplan*, blending Mediterranean elegance with modern functionality. Step through the grand 8’ arched double doors into a spacious open layout with soaring ceilings, a gourmet kitchen with KitchenAid appliances, gas cooktop, granite countertops, walk-in pantry, and expansive living and dining areas—all with views of the **resort-style private pool**. The first floor offers a second owner’s suite, office, and guest bath. Upstairs, the primary suite is a true retreat with a rotunda entry, spa-style bath, massive walk-in closet, and balcony access, along with a bonus room and two additional en-suite bedrooms. Upgrades include a **whole-home water filtration system**, barrel tile roof, Trex balconies, coffered ceilings, crown molding, hand-forged iron staircase, **solar panel system**, and **two Tesla EV chargers**. Enjoy scenic views from this premium corner lot, ideally located near major highways and world-famous attractions. With only 58 homes, this exclusive community offers peaceful luxury living at its finest. Schedule your private tour today!
2018 | 4 | 4 | 3,665 sqft.
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$1,400,000 - Winter Garden, FL
10219 Atwater Bay Drive Winter Garden, FL - Welcome to this stunning lakefront pool home in the highly sought after Waterleigh community of Winter Garden. Overlooking Hickorynut Lake, this home is designed for both comfort and luxury. Boasting five bedrooms and three and a half baths, it offers an exceptional blend of modern elegance and functional living space. With an open concept layout, high ceilings, and plantation shutters throughout, this home provides a bright and airy atmosphere, perfect for both everyday living and entertaining. As you step inside, you’ll be greeted by a spacious foyer leading into the main living area, where expansive windows frame breathtaking views of the backyard. The gourmet kitchen is truly the heart of the home, featuring a large island with seating, quartz countertops, stacked ovens, a custom backsplash, and ample cabinet space. Overlooking the dining and living areas, this kitchen is perfect for entertaining guests or enjoying family meals with a view. The first floor primary suite offers a private retreat with serene water views, a spa like ensuite bath with dual vanities, a large zero threshold double shower, and a spacious walk in closet. Upstairs, you’ll find a generous loft area that is ideal for a second living space, playroom, or home office. Four spacious guest bedrooms and a Jack-and-Jill bath complete the second floor, providing plenty of room for family and visitors. Stepping outside, you’ll find a covered front porch that welcomes you home, while the screened back porch provides the perfect space to relax and take in the tranquil views. The highlight of the backyard is the heated saltwater pool, creating your own private oasis for year round enjoyment. The three-car tandem garage offers ample storage, including overhead storage racks and two electric car chargers, ensuring both convenience and efficiency. To maintain the home's impeccable condition, the driveway and pool pavers were cleaned and sealed, and the exterior was freshly painted in 2025. Beyond the home itself, the Waterleigh community offers an unparalleled resort-style living experience. Residents enjoy access to three community pools, two fitness clubhouses, tennis and pickleball courts, mini golf, scenic parks, multiple playgrounds, and a community fishing dock. With meticulously maintained landscaping included in the HOA, you’ll have more time to relax and enjoy all the amenities this vibrant community has to offer. Located in Winter Garden, this home is just minutes from Disney/Universal Parks, world-class shopping and dining, major highways, and top rated schools. Whether you’re heading to work, enjoying a day at the theme parks, or exploring nearby attractions, this home provides the perfect combination of luxury, convenience, and community. This spectacular lakefront home is a rare find. Schedule your private showing today.
2019 | 5 | 4 | 3,911 sqft.
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$1,395,000 - Winter Garden, FL
7536 Green Mountain Way Winter Garden, FL - Discover elegance and comfort in this expansive 4,800 sq. ft. home at 7536 Green Mountain Way, nestled in the prestigious Highlands at Overlook at Hamlin of Winter Garden. This beautifully updated 6-bedroom, 5-bathroom residence, freshly repainted inside and out, offers a perfect blend of modern luxury and family-friendly functionality. Enter into a grand, light-filled interior with an open-concept design, featuring high ceilings and stylish finishes. The state-of-the-art kitchen is a culinary haven, equipped with granite countertops, stainless steel appliances, a spacious island, and abundant storage, ideal for hosting or everyday meals. The adjacent living and dining areas create a seamless flow, perfect for entertaining or cozy family nights. The luxurious primary suite is a private oasis, boasting a generous walk-in closet and a spa-like en-suite with dual sinks, a soaking tub, and a walk-in shower. Five additional well-appointed bedrooms provide ample space for family, guests, or home offices, complemented by multiple bathrooms for ultimate convenience. The home’s north-facing front exposure ensures a shaded front yard, while the sunny backyard offers a serene space for outdoor activities or relaxation. Enjoy a meticulously landscaped lot, perfect for gatherings, plus a three-car garage for storage and convenience. Residents also benefit from community perks like parks, a pool, and scenic trails. Ideally located near top schools, shopping, dining, and Orlando’s renowned attractions, this move-in-ready home delivers the best of Winter Garden living. Schedule your showing today to experience this exceptional property firsthand!
2014 | 6 | 4 | 4,806 sqft.