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Recently Sold Listings in Winter Garden, FL

Welcome to your dedicated resource for viewing Sold listings in Winter Garden, FL. As a local Winter Garden, FL agent, The Nest Group specializes in the unique market dynamics of this area, offering insights home values, selling strategies, and options like cash offers. Start exploring the most recent sold properties in Winter Garden, FL below, or if you are looking to sell a home in Winter Garden, FL contact a local agent to discuss the possibilities.

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All Sold Homes for Sale in Winter Garden, FL

$1,099,000
6 Beds 5 Baths Cypress Reserve Ph 2 SubDv. 34787 Zip Code
Experience luxury living in this exceptional 6-bedroom, 5-bathroom residence located in the highly sought-after Cypress Reserve community of Winter Garden. Perfectly positioned on a premium homesite with no rear neighbors, this impressive home offers exceptional privacy, tranquil conservation views, and a versatile floor plan designed for today’s lifestyle. The open-concept design showcases beautifully appointed living spaces throughout both floors, making it ideal for multigenerational living or hosting extended family and guests. A dramatic second-floor loft overlooks the main living area, creating an open and inviting atmosphere while providing additional living space. Upstairs also features a second primary suite, three additional spacious bedrooms, a dedicated theater/media room, and a flex room that serves perfectly as a home office, den, or playroom. At the heart of the home is a chef-inspired gourmet kitchen designed to impress, featuring stainless steel appliances, a gas cooktop, double wall ovens, quartz countertops, and an oversized center island with an undermount sink, generous seating, and double-sided cabinetry that provides exceptional storage for both everyday living and entertaining. Motorized shades throughout the main living area add a touch of sophistication and everyday convenience. The spacious family room opens effortlessly to the outdoor living space through triple pocket sliding glass doors, creating a seamless indoor-outdoor lifestyle. Relax year-round on the screened lanai overlooking peaceful conservation views or entertain with ease around the sparkling pool and fully equipped outdoor kitchen featuring a Paradise Grill, built-in sink, and refrigerator. Luxurious owner's suite is a private retreat featuring a spa-inspired bath with dual vanities, a relaxing garden tub, a zero-entry walk-in shower with seamless glass enclosure, and double-door entry to an expansive custom-designed walk-in closet that is sure to impress. A private hallway just off the main living area leads to a spacious guest suite with direct access to the pool, along with a generously sized laundry room for added convenience. Upstairs, you'll find a second primary suite, three additional bedrooms, an expansive loft, a dedicated theater/media room, and a versatile flex room—offering abundant space for family, guests, a home office, fitness room, or additional living area. Additional highlights include a three-car tandem garage offering abundant storage and ample room for a home gym, workshop, or hobby space. LOCATED just minutes from Downtown Winter Garden, the award-winning Winter Garden Farmers Market, Winter Garden Village, shopping, dining, top-rated schools, and major roadways including State Road 429 and Florida’s Turnpike, this exceptional home offers the perfect blend of luxury, comfort, convenience, and location *** This is a rare opportunity to own one of Cypress Reserve’s premier residences and experience the very best of the Winter Garden and true Florida lifestyle. ***

14067 Jomatt Loop, Winter Garden

$1,500,000
5 Beds 4 Baths Hull Island/Oakland Ph 2 SubDv. 34787 Zip Code
Welcome to this stunning, like-new home that perfectly blends luxury, comfort, and modern design in the highly desirable community of Hull Island. Boasting five spacious bedrooms and four full bathrooms, this thoughtfully designed residence offers an ideal layout for both everyday living and entertaining. This home offers two spacious owner’s suites, one conveniently located on the first floor and another upstairs, making it ideal for multigenerational living, extended guests, or added privacy. Step inside to soaring high ceilings and an open-concept floor plan filled with natural light. The heart of the home is the gourmet gas kitchen, featuring 42-inch cabinetry, elegant quartz countertops, a large center island, built-in convection oven, stainless steel appliances and premium finishes throughout. A dedicated beverage station with a separate bar refrigerator provides the perfect space for entertaining guests. Upstairs, you'll find an expansive loft that offers endless possibilities as a media room, game room, home office, or additional living space. Outside, enjoy your own private backyard retreat complete with a sparkling pool, ideal for relaxing or hosting family and friends year-round. The garage is equipped with overhead storage shelving, providing ample space to keep seasonal items and equipment neatly organized. With its spacious layout, upscale finishes, abundant storage, and exceptional amenities, this beautifully maintained home is truly move-in ready and offers the perfect combination of elegance, functionality, and Florida living at its finest. This community features a pool pool, nature trails, playground, dog park, and private dock. Conveniently located near shopping, dining, main highway and more.

2010 Boss Hewett Street, Winter Garden

$569,900
3 Beds 3 Baths Waterleigh SubDv. 34787 Zip Code
Better than new! Move-in ready with premium upgrades and resort-style living in the highly sought-after Waterleigh community! This beautiful all-concrete block construction home offers 3 bedrooms, 2.5 bathrooms, and a thoughtfully designed open-concept floor plan that perfectly blends comfort, style, and functionality. The spacious kitchen overlooks the dining and great room while offering views of the covered lanai, creating the perfect setting for everyday living and entertaining. Featuring a large center island with bar seating, abundant cabinetry, generous counter space, and stainless steel appliances, the kitchen is truly the heart of the home. The first floor also includes a versatile FLEX ROOM, ideal for a home office, playroom, or fitness space, along with a convenient half bath. A custom WINE CELLAR built beneath the staircase adds a unique touch for wine enthusiasts. Upstairs, the spacious primary suite features a large walk-in closet and an ensuite bathroom with dual vanities. Two additional bedrooms share a full bathroom, while the upstairs laundry room adds everyday convenience. A rear-entry TWO-CAR GARAGE with a practical drop zone completes the home. This property has been thoughtfully upgraded with premium features that truly set it apart, including LAMINATE FLOORING throughout the entire second floor, a built-in SAUNA in the primary bathroom, a SCREEN-ENCLOSED LANAI with an above-ground HOT TUB, and ENERGY-SAVING SOLAR PANELS. Located in the award-winning Waterleigh community, residents enjoy resort-style amenities including multiple pools, clubhouses, fitness centers, tennis and pickleball courts, playgrounds, scenic walking trails, dog parks, community gardens, and beautiful lakes throughout the neighborhood. Waterleigh is also known for its outstanding educational opportunities, with TWO A-RATED SCHOOLS inside the community, including an A-rated middle school ranked among the top-performing schools in Orange County. Conveniently located just minutes from Walt Disney World, Hamlin Town Center, Horizon West, shopping, dining, medical facilities, and major highways, this home offers the perfect combination of luxury, convenience, energy efficiency, and one of Central Florida's most desirable communities.

16625 Point Rock Drive, Winter Garden

$555,000
3 Beds 3 Baths Serenade/Ovation Ph 1 SubDv. 34787 Zip Code
Exquisite Model Home Investment Opportunity | Just Minutes from Disney Experience the perfect blend of luxury, elegance, and investment potential with this exceptional Dream Finders Homes Model Residence, located in one of Central Florida's newest and most desirable communities. Situated on a premium corner homesite, this beautifully appointed 3-bedroom, 2.5-bath home showcases every detail today's discerning buyer is looking for. Professionally designed and loaded with the builder's finest upgrades. From the moment you enter, you'll appreciate the bright open-concept floor plan, soaring ceilings, abundant natural light, and designer finishes throughout. The spectacular gourmet chef's kitchen is the centerpiece of the home, featuring: • Elegant quartz countertops • Premium cabinetry • Stainless steel appliances • Spacious center island perfect for entertaining • Designer lighting package • Luxury finishes throughout The expansive owner's suite offers a spa-inspired retreat complete with dual vanities, quartz countertops, a large walk-in shower, and generous walk-in closet space. Additional features include: 3 Bedrooms 2.5 Bathrooms Premium Corner Lot All Kitchen Appliances Included Luxury Upgrades Throughout Covered Outdoor Living Space Energy-Efficient Construction Outstanding Investment Opportunity One of the most unique features of this property is that it is currently being utilized by Dream Finders Homes as their professionally decorated Model Home. The builder is presently paying $4,486 monthly to lease the property back from the owner, allowing the new purchaser to assume an attractive income-producing opportunity while the builder continues operating the home as its sales model, subject to the terms of the existing lease. Whether you're looking for a luxury primary residence or an exceptional investment with immediate rental income, this property offers a truly rare opportunity. Community Highlights • Low HOA • No CDD • Brand-new community • Minutes from Walt Disney World Resort • Convenient access to shopping, dining, entertainment, and major highways This is far more than a home—it's a luxury lifestyle combined with an exceptional investment opportunity. Schedule your private showing today and discover why this extraordinary Model Home stands above the rest.

13006 Serene Glade Road, Winter Garden

$559,000
3 Beds 2 Baths Hull Island/Oakland SubDv. 34787 Zip Code
JUST REDUCED $30,000! EXCEPTIONAL VALUE in the Sought-After Hull Island Community! If you’ve been waiting for the right home at the right price, this is your opportunity! Make your move before the new school year begins and enjoy everything this wonderful family-friendly community has to offer. This beautifully maintained 3-bedroom, 2-bath home offers over 1,800 square feet of thoughtfully designed living space in the highly sought-after Hull Island community of Oakland. Tasteful décor and stylish finishes create a warm, inviting atmosphere, while the open-concept floor plan features a spacious kitchen with stainless steel appliances, a large center island with counter seating, and seamless flow into the living and dining areas—perfect for everyday living and entertaining. Step outside to your private backyard with maintenance-free turf, providing a lush, green outdoor space you can enjoy year-round without the upkeep. Residents enjoy a community pool, scenic walking trails, direct access to the West Orange Trail, and beautiful Lake Apopka just a couple of blocks away. Best of all, you’ll enjoy these amenities with a LOW HOA fee! Whether you’re purchasing your first home, growing your family, or right-sizing after the kids have moved out, this home offers the perfect combination of comfort, convenience, and low-maintenance living. Hull Island is a welcoming community for all ages, conveniently located just minutes from charming downtown Winter Garden, shopping, dining, parks, and major roadways. Now offered at just $559,000—don’t miss this exceptional opportunity to own one of the best values in the area. Schedule your private showing today!

1808 Western Trailway Drive, Oakland

$1,450,000
4 Beds 4 Baths Lakeshore Preserve Ph 4 SubDv. 34787 Zip Code
Captivating water and golf course views set the stage for a chic and distinguished single-story residence in Lakeshore Preserve. This better-than-new home boasts a great room floorplan with split bedroom layout, sliding pocket doors, an exceptional screened pool patio area with hybrid saltwater and chlorine pool with sun shelf and water features, plus tranquil lake beyond. Elegant white on white kitchen with stainless appliances, gas cooktop with hood, waterfall quartz island, and an abundance of cabinetry including a few lighted glass showplace cubicles with doors. Graced with wood-look tile flooring and transitional neutral grays and whites throughout this home offers a clean-look elegant canvas. Landscape lighting creates an elegant ambiance at night. Enjoy a nearly carefree lifestyle with exterior yard maintenance included in your monthly HOA fee. 1-gig high-speed internet is also included. Community features resort-style amenities including a waterfront community pool, cabanas, walking trails, and access to Lake Panther via a community ramp for canoes, kayaks, and other non-motorized watercraft. There’s also a community clubhouse with fitness center and activity spaces. Top-rated Panther Lake Elementary is located within the neighborhood and Horizon High School is across the street. Orange County National Golf Center is just minutes away. Enjoy nightly fireworks from the Magic Kingdom at Walt Disney World and easy access to the SR-429 to connect to downtown Orlando. Welcome to Horizon West’s best address for lifestyle, luxury, and livability.

15619 Giant Foxtail Court, Winter Garden

$905,000
5 Beds 5 Baths Watermark Ph 4a SubDv. 34787 Zip Code
Built by Meritage Homes, this beautifully designed two story home offers the perfect blend of style, functionality, and energy efficiency with solar panels. Step inside and you’re welcomed by a versatile flex room just off the foyer, currently serving as a home office but easily adaptable to fit your lifestyle. The first floor also features a full bedroom and full bathroom, providing added flexibility for guests, multi-generational living, or a private workspace. Continue into the heart of the home where the open concept floor plan features tile flooring throughout the main living areas, a spacious kitchen with a large center island overlooking the living room, and a custom stone entertainment wall with built in shelving that creates a striking focal point. Upstairs, you’ll find a generous loft offering additional living space, along with a spacious primary suite featuring a custom designed walk in closet. The thoughtfully upgraded laundry room includes built in cabinetry and countertop workspace for added convenience. The remaining bedrooms are also located on the second floor, two of the secondary bedrooms are connected by a convenient Jack and Jill bathroom, offering a functional layout that provides privacy while maintaining easy access for family or guests. Step outside to a screened lanai overlooking an expansive backyard that provides exceptional space for future enhancements, including a custom pool, outdoor kitchen, or extended entertaining area. Residents enjoy exceptional community amenities, including a resort style pool with water slides and splash features, a clubhouse, fitness center, playground, tennis courts, and pickleball courts offering something for everyone to enjoy.

15031 Guava Bay Drive, Winter Garden

$499,900
3 Beds 3 Baths Waterleigh Ph 3b 3c &3d SubDv. 34787 Zip Code
Welcome to 16161 Mangrove Road, where modern elegance meets resort-style living in the award-winning Waterleigh community! This beautifully maintained 3-bedroom, 2.5-bath home offers the perfect combination of timeless design, spacious living, and an unbeatable location in the heart of Winter Garden. Step inside to discover an inviting open-concept floor plan filled with natural light, soaring ceilings, and stylish tile flooring throughout the main level. The spacious living and dining areas seamlessly flow into the stunning gourmet kitchen, featuring quartz countertops, an oversized center island, stainless steel appliances, abundant shaker cabinetry, a walk-in pantry, and plenty of prep space perfect for entertaining or everyday living. Upstairs, the master bedroom offers plenty of space and includes an oversized walk-in closet, and a spa-inspired ensuite with dual vanities and quartz countertops. Two generously sized secondary bedrooms share a full bath, while the upstairs loft provides the perfect flex space for a playroom, home office, or media area. Step outside to your covered brick-paver lanai, creating the ideal space for morning coffee, weekend barbecues, or relaxing with friends year-round. Living in Waterleigh means enjoying one of Central Florida's most sought-after master-planned communities. Residents enjoy resort-style pools, an elegant clubhouse, tennis courts, playgrounds, fitness centers, scenic walking trails, dog parks, picnic areas, and beautifully maintained green spaces. Community pool, mailbox, and playground is just a few steps away from the house making life even more enjoyable and convenient. You will also love the ability to walk to top-rated A+ schools located right within the neighborhood the elementary school is just a few blocks away and the middle school is the highest ranking middle school in the district for Orange County. Ideally located in Horizon West, you'll also be just minutes from Hamlin Town Center, Flamingo Crossings, Walt Disney World, shopping, dining, major highways, and everything Central Florida has to offer. Whether you're looking for your first home, your forever home, or simply a place where every day feels like a vacation, this home and community delivers the lifestyle you've been waiting for. Schedule your private showing today and experience all that Waterleigh has to offer!

16161 Mangrove Road, Winter Garden

$1,025,000
6 Beds 6 Baths Latham Park South SubDv. 34787 Zip Code
Welcome to this exceptional home in the highly sought-after Latham Park community, where luxury, space, and privacy come together. Situated on a premium conservation lot with no rear or front neighbors, this beautifully upgraded residence offers the perfect blend of elegance, comfort, and functionality. Featuring 6 bedrooms, 5 full bathrooms, and 1 half bathroom, this thoughtfully designed floor plan is ideal for multigenerational living and effortless entertaining. The first floor offers two private bedroom suites, perfect for guests or extended family, along with a convenient half bath. Upstairs, you'll find four additional bedrooms, including a spacious owner's suite and a newly added sixth bedroom with its own private en-suite bath. The remaining bedrooms are served by one full bath and a Jack-and-Jill bathroom, providing comfort and convenience for everyone. Designed with premium finishes throughout, this home features genuine hardwood flooring in the main living areas, adding timeless elegance that sets it apart from standard vinyl flooring. The gourmet kitchen and all bathrooms showcase beautiful granite countertops, enhancing both style and durability. The open-concept layout seamlessly connects the kitchen, dining, and living areas, while the expanded family room provides even more space for gathering and entertaining. An enlarged secondary bedroom offers additional flexibility for guests, a home office, or a private retreat. Additional highlights include a 3-car garage, generous living spaces, and breathtaking conservation views that provide exceptional privacy and a peaceful natural backdrop. Ideally located just minutes from top-rated schools, shopping, dining, major highways, and Walt Disney World, this move-in-ready home presents a rare opportunity to own one of the finest properties in one of Winter Garden's most desirable communities. Don't miss your chance to own this exceptional conservation-lot home featuring six bedrooms, premium upgrades, expanded living spaces, and an unbeatable location!

9240 Bradleigh Drive, Winter Garden

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