Explore Homes for Sale in Winter Garden, FL
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Discover Your Dream Home: Explore Winter Garden, FL Homes For Sale with The Nest Group

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Winter Garden, FL, offers a vibrant real estate market with diverse homes for sale, perfect for every lifestyle. From charming historic bungalows in the downtown area to modern family residences in master-planned communities like Hamlin and Horizon West, prospective buyers will discover unparalleled opportunities. The Nest Group specializes in helping you navigate the unique offerings of Winter Garden, ensuring you find a property that perfectly matches your dreams. Explore the latest listings, experience the welcoming community spirit, and imagine life amidst beautiful natural surroundings and convenient access to Central Florida's best attractions. Your ideal Winter Garden home awaits.

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Winter Garden, FL Communities

Exploring Winter Garden's Diverse Real Estate Landscape

A Spectrum of Homes for Sale in Winter Garden, FL

Winter Garden, Florida, consistently ranks as one of Central Florida's most sought-after locations for new residents. Consequently, the inventory of homes for sale here is remarkably varied, appealing to a wide array of preferences and budgets. Whether you're seeking a quaint starter home or an expansive luxury estate, the Winter Garden real estate market presents a compelling selection.

Historic Charm Meets Modern Living: Downtown Winter Garden Homes

For those enchanted by character and community, downtown Winter Garden homes offer a unique appeal. Nestled around the iconic Plant Street, you'll find beautifully preserved and meticulously renovated bungalows and historic properties for sale. These residences provide direct access to the vibrant Plant Street Market, local eateries, boutiques, and the scenic West Orange Trail, embodying a truly walkable lifestyle.

New Construction Homes in Horizon West & Beyond

On the flip side, the sprawling Horizon West area, a significant part of Winter Garden, is a hub for new construction homes. Neighborhoods like Hamlin, Lakeside Village, Summerport, Independence, and Storey Grove feature an abundance of newly built homes for sale, often within master-planned communities. These areas are renowned for their state-of-the-art amenities, top-rated schools, and family-friendly environments, offering modern designs and energy-efficient features perfect for contemporary living.

Lifestyle & Community: What Makes Winter Garden Homes So Desirable?

Embrace the Winter Garden Lifestyle

Beyond the impressive selection of homes for sale, Winter Garden boasts a lifestyle that truly sets it apart. Residents enjoy a harmonious blend of small-town charm and big-city conveniences. Weekends can be spent cycling the West Orange Trail, exploring the Farmers Market, or enjoying live music and events on Plant Street. The close-knit community actively participates in local festivals and gatherings, fostering a genuine sense of belonging.

Family-Friendly Amenities and Top-Rated Schools

Families consistently choose Winter Garden for its exceptional quality of life. The community is home to numerous parks, recreational facilities, and highly-rated public and private schools, making it an ideal place to raise children. When considering homes for sale, the proximity to these essential family amenities often plays a crucial role in the decision-making process for many prospective buyers.

Finding Your Perfect Match: Types of Homes for Sale in Winter Garden

Single-Family Homes: Space and Serenity

The majority of homes for sale in Winter Garden are single-family residences, offering diverse architectural styles and lot sizes. From spacious suburban homes with private yards to elegant properties in gated communities like Oakland Park, there's a single-family home to suit every family's needs, providing ample space for growth and personalization.

Townhomes & Villas: Convenient Winter Garden Living

For those seeking a lower-maintenance lifestyle without compromising on location or amenities, Winter Garden also offers an excellent selection of townhomes and villas for sale. These properties are often found in communities with shared amenities like pools and clubhouses, presenting an attractive option for first-time buyers, downsizers, or those seeking a convenient lock-and-leave lifestyle near all local conveniences.

Luxury & Waterfront Homes for Sale in Winter Garden

Winter Garden's real estate market also caters to the luxury segment, featuring exquisite estates and waterfront homes for sale. Properties overlooking Lake Apopka or situated in exclusive enclaves offer premium finishes, expansive living spaces, and often private docks or stunning natural views. These luxury homes represent the pinnacle of Winter Garden living, combining elegance with a coveted Central Florida address.

Navigating the Winter Garden Real Estate Market

The Nest Group: Your Local Winter Garden Real Estate Experts

Successfully navigating the dynamic Winter Garden real estate market requires local expertise and insight. As your dedicated real estate partners, The Nest Group brings unparalleled knowledge of Winter Garden's neighborhoods, market trends, and hidden gems. We are committed to helping you discover the ideal homes for sale that align with your vision and lifestyle in this beautiful Central Florida community.

Newest Homes for Sale in Winter Garden, FL

$699,000
4 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 3b 3c & 3d SubDv. ⋅ 34787 Zip Code
Short Sale. ***SHORT SALE. ***ALL OFFERS MUST GO THROUGH SHORT SALE PROCESS WITH SELLERS LENDER FOR APPROVAL/DENIAL.** The Bellmore in Waterleigh! This elegant single-story four-bedroom, two-bath residence offers 2,984 total square feet of refined living on a premier corner lot with wooded privacy and pond access. Blending timeless design with modern upgrades, this home showcases luxury finishes inside and out. The gourmet kitchen is a centerpiece, featuring stainless steel appliances, a walk-in pantry, and an oversized island with abundant prep and seating space. It opens seamlessly to the spacious family room, creating a setting for gatherings. Designer touches include recessed wood-insert ceilings in the foyer and primary suite, a dramatic brick accent wall in the living room, upgraded lighting throughout and a striking chandelier in the foyer. The primary suite offers a custom closet organization system, while ceiling fans are thoughtfully placed in almost every room. Outdoor living rivals a private resort with a screened, heated saltwater pool and cascading waterfalls, surrounded by lush tropical landscaping. The covered lanai features a 10-foot drop-down projection screen for outdoor cinema nights, while brick pavers enhance the driveway, walkways, and patio. A 13.67-kilowatt solar system with net metering ensures energy efficiency. From the backyard, enjoy nightly views of the spectacular Disney fireworks—an unforgettable backdrop unique to Central Florida living. Optional luxury additions for additional purchase include a four-seat electric golf cart with charger, professional-grade garage storage racks and a complete home gym with free weights. Waterleigh is Winter Garden’s flagship planned community, offering two expansive clubhouses with resort-style pools, state-of-the-art fitness centers, tennis courts, miniature golf, walking trails, dog parks, community gardens and scenic lakes with fishing piers. Ideally near Disney, major highways, shopping and dining, Waterleigh combines convenience with unmatched amenities. Ranked as one of the top communities in the United States, Winter Garden is celebrated for its vibrant downtown, lifestyle amenities and exceptional quality of life—making this home a rare opportunity to own in one of the nation’s desirable areas. This one is a must-see. By appointment only. BUYER MUST ASSUME 50K SOLAR PANEL LOAN- BANK WILL NOT CONSIDER ANY OFFERS ASKING FOR BANK TO PAY OFF SOLAR PANELS. OCCUPIED- BY APPOINTMENT ONLY.

9605 Lost Creek Drive, Winter Garden
$289,500
3 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condominium 2 SubDv. ⋅ 34787 Zip Code
Escape to your own luxurious, fully furnished condo-hotel residence at the prestigious Grove Resort & Water Park—just minutes from Walt Disney World. Designed for both personal enjoyment and investment, this exceptional unit offers the perfect combination of a turnkey vacation retreat and high-performing income asset. Located on the third floor of Condominium II, the sought-after Jasmine floor plan boasts an open-concept living area filled with natural light, a modern kitchen with stainless steel appliances, sleek countertops, and the convenience of in-unit laundry. Step out onto the extended screened balcony to enjoy tranquil resort and conservation views—an ideal space for morning coffee or evening relaxation. As an owner, you and your guests will experience resort living at its finest. The Surfari Water Park features a thrilling lazy river, water slides, and the FlowRider surf simulator. Multiple heated pools, hot tubs, and private cabanas create endless opportunities for relaxation, while children will love the splash zones, game arcade, and dedicated play areas. Beyond the water attractions, the resort offers on-site restaurants and bars, a grocery café, full-service spa, fitness center, mini-golf, boat rentals, and 24-hour concierge services—all within a secure, award-winning community. This unit is part of the professionally managed hotel rental program, offering truly hands-free ownership. With full-service management covering marketing, bookings, housekeeping, and maintenance, owners can enjoy strong cash-flow potential while eliminating the stress of day-to-day operations. Whether you’re looking for a private getaway near Orlando’s top attractions or a proven income-producing property, this Grove Resort condo presents an unmatched opportunity. Experience luxury, convenience, and investment potential in one of Central Florida’s premier resort communities. Schedule your private tour today!

14501 Grove Resort Avenue Unit 2334, Winter Garden
$791,000
4 Beds ⋅ 4 Baths ⋅ Hawksmoor-Ph 1 SubDv. ⋅ 34787 Zip Code
This stunning 4-bedroom, 3.5-bath residence sits proudly in the highly sought-after Hawksmoor community of Winter Garden. Designed with a modern open-concept layout and upgraded with premium finishes, this home blends elegance, functionality, and comfort. Perfectly positioned near the Orange County National Golf Center and Lodge—home to the nation’s largest driving range—this property also offers quick access to Orlando Health Hospital, brand-new top-rated schools, shopping, fine dining, and entertainment. With Highway 429 just minutes away, world-famous Orlando theme parks are practically at your doorstep. House is leased until Nov/2026 and buyer must honor the contract. Step inside and be welcomed by soaring ceilings and a bright, spacious floor plan. The luxurious primary suite with a spa-inspired ensuite is conveniently located on the main level, while the second floor offers three beautifully designed bedrooms, a bonus living/play area, and ample space for family or guests. A flex room on the first floor can serve as a home office, library, or formal dining area. At the heart of the home, you’ll find a chef’s kitchen featuring stainless steel appliances, custom 42" cabinetry, oversized granite island seating up to six, walk-in pantry, and butler’s bar connecting to the dining/flex space. Perfect for both everyday living and entertaining. Outside your door, Hawksmoor provides resort-style amenities, including a zero-entry pool with splash area, clubhouse with private rental options, fitness center, yoga lawn, Zen garden, and community walking trails around picturesque lakes and ponds. This is more than just a house—it’s a lifestyle. Don’t miss the chance to make this exceptional property your new home in one of Winter Garden’s most desirable communities.

16555 Wingspread Loop, Winter Garden
$575,000
4 Beds ⋅ 4 Baths ⋅ Waterleigh Ph 4a SubDv. ⋅ 34787 Zip Code
Discover 11045 BOSTWICK ALY in Winter Garden—where you’ll live in one of the most sought-after neighborhoods with top-rated A+ schools just steps away. Imagine your mornings: a quick walk to school, serene landscaping views from your porch, and all the best resort-style amenities at your fingertips—playgrounds, fitness centers, nature trails, and more! This gorgeous 4-bedroom, 3.5-bath home is built for modern living with smart home features, energy-saving solar panels (paid by the seller!), and easy access to everything Winter Garden offers—charming shops, amazing restaurants, and vibrant downtown. All concrete block construction on both first and second floor single-family home features 4 bedrooms and 3.5 bathrooms optimizing living space with an open concept feel. A beautiful porch welcomes you to this home, as you enter the foyer, you’ll find the first bedroom complete with ensuite bathroom and a powder room across the hall. The well-appointed kitchen overlooking the great room, dining room, and oversized outdoor lanai. The kitchen features granite countertops, stainless steel appliances, spacious walk-in pantry and an island with bar seating. As we head up to the second floor, we are greeted with a loft area and additional three bedrooms. Bedroom one is located just off the loft space and includes a spacious walk-in closet as well as ensuite bathroom with double vanity sinks and separate toilet area. Two additional bedrooms share a second upstairs bathroom and linen closet for extra storage. Your laundry room is located on the second floor for convenience. This home features a two car garage located at the rear of the home with drop zone as you enter the first floor. Waterleigh community is well know for prime location with a lot of lifestyles amenities such Playgrounds & Sports Fields, Indoor Fitness Centers, Scenic Lakes and Ponds, Community Garden Mini-Golf, Walking & Nature Trails, Beach Volleyball & Hammock Beach This prime location with this particular meticulous home is great spot that leads you to enjoy easy access to a vibrant array of shops, restaurants, and entertainment options. The historic downtown area offers charming boutiques and family-owned eateries, while the nearby Winter Garden Village provides a more modern shopping experience with over 100 retailers.

11045 Bostwick Alley, Winter Garden
$414,000
34787 Zip Code
Established boba tea business with high gross sales. Cash buyers only! NDA and proof of funds are required!

Winter Garden
$350,000
3 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo 3 SubDv. ⋅ 34787 Zip Code
Welcome to Your Perfect Orlando Investment & Vacation Escape! This beautifully appointed condo-hotel unit offers the ideal combination of investment potential and vacation paradise. Featuring 3 spacious bedrooms, 2 modern bathrooms, and 1,396 sq. ft. of living space, this residence provides plenty of room for relaxation and entertainment—all with a picturesque fountain view. Enjoy gourmet meals at the Valencia Restaurant or satisfy your sweet tooth at the on-site coffee shop and ice cream parlor. Stay active in the state-of-the-art fitness center or unwind with rejuvenating spa treatments. Challenge friends in the game room, enjoy mini-golf, or dive into hours of arcade fun. Make the most of two sparkling pools complete with a waterpark, lazy river, splash zone, and poolside bar & grill. Perfectly located near Orlando’s world-famous attractions, this property is designed for both vacation enjoyment and lucrative investment returns. Whether you’re relaxing by the fountain, exploring the city, or maximizing rental income, this condo-hotel offers the best of both worlds. Own your slice of Orlando paradise today!

14501 Grove Resort Avenue Unit 3202, Winter Garden
$989,900
4 Beds ⋅ 4 Baths ⋅ Waterleigh Ph 2b SubDv. ⋅ 34787 Zip Code
Stunning Emerald serie house, Selden model built in 2018 well maintained, featuring 4 bedrooms, 3.5 bathrooms, and approximately 2,920 sq ft of living space. Situated on a premium corner lot of about 10,585 sq ft, this home offers a 3-car tandem garage, spacious backyard, private wooded views, and a screen-enclosed private pool—perfect for year-round Florida living. The open-concept design includes a formal dining room, elegant foyer with wrought-iron staircase, and a gourmet kitchen with a large island, 42” cabinets with crown molding, granite countertops, stainless steel appliances, and a convenient drop zone from the garage. The owner’s suite boasts a tray ceiling, a spa-like en-suite bathroom with dual sinks, a garden tub, and a spacious walk-in closet. Additional features include a durable concrete tile roof, dual A/C units, and numerous upgrades: exterior lighting, sealed paver driveway and porch, landscape lighting, decorative stonework, epoxy-finished garage floor, and professional landscaping. Lawn care is included with HOA fee. Located in the highly sought-after Waterleigh community in Winter Garden, residents enjoy resort-style amenities: two community clubhouses, 4 resort-style pools, 2 fitness center, beach volleyball, 2 tennis courts, mini-golf, community garden, dog park, fishing pier, and scenic walking/biking trails. The neighborhood is beautifully landscaped with lakes, green spaces, and planned community events. Conveniently located just minutes from Historic Downtown Winter Garden, Winter Garden Village, and easy access to SR-429 for a quick commute to Orlando and Walt Disney World. Zoned for top-rated schools: Atwater bay Elementary, Water Spring Middle, and Horizon High School.

10007 Little Alcove Loop, Winter Garden
$799,900
Acreage & Unrec SubDv. ⋅ 34787 Zip Code
Serene 5 acre property! Zoned for residential and agricultural use. Whether you envision building your dream home, farming or simply enjoying the peaceful landscape, this land offers country living without sacrificing city amenities. For those looking for a turnkey solution, the property is also available as a to-be-built custom home opportunity with Lionshead Homes, allowing buyers to design and build a luxury residence tailored to their lifestyle. Conveniently located just 7 minutes to Publix at Hamlin or Publix at Stoneybrook. Shopping, dining, medical offices, hospitals, movie theater are all close by! Disney World 20 minutes. Orlando International Airport 35 min. Contact us for additional information and take the first step towards owning your slice of rural paradise!

9940 Black Bear Lane, Winter Garden
$575,000
Briley Farm SubDv. ⋅ 34787 Zip Code
Briley Farm, Central Florida’s newest custom home community, sits on 111 acres of lush landscape in Oakland, Florida. Here, you’ll have the opportunity to build your dream custom home with Pioneer Builders on a .45-acre corner lot. Pioneer Builders is renowned for their commitment to craftsmanship, attention to detail, and creating homes that reflect each client’s unique style. Every residence is meticulously designed to complement its natural surroundings, with spacious floor plans that flow from room to room—airy yet cozy and ready for your personal touch. Enjoy the perfect balance of indoor and outdoor living, set against serene scenery while remaining close to shopping, restaurants, and major highways. Briley Farm offers comfortable countryside living under a canopy of welcoming trees, crafted to embody the lifestyle you’ve been searching for. Stop by our sales office today to start building your dream home with Pioneer Builders!

514 N Pollard Street, Oakland
$599,000
4 Beds ⋅ 4 Baths ⋅ Waterleigh Ph 4b & 4c SubDv. ⋅ 34787 Zip Code
A home full of charm, comfort, and practicality. It features four bedrooms, including a spacious master suite, three full bathrooms, and a powder room, distributed in a clever layout that enhances each room. Right at the entrance, the balcony invites you to slow down and enjoy the home's cozy atmosphere. The kitchen is modern and functional, equipped with all essential appliances and a central island perfect for quick meals or family time. The laundry room is also fully equipped and ready for everyday use. Upstairs, a spacious loft opens up to new possibilities—it could be a TV room, office, or leisure space—in addition to three bright and comfortable bedrooms. Sliding doors connect the interior area with the private backyard, where the covered balcony offers stunning views. With no neighbors in the back, the environment is quiet, private, and ideal for relaxation. The condominium offers a complete infrastructure, with swimming pools, gyms, and leisure areas for the whole family. The location is strategic, with supermarkets, schools, and various amenities nearby, as well as easy access to the region's main attractions. The house is currently occupied, but you can schedule a viewing. A rare opportunity to live well, with tranquility and quality of life.

17865 Adrift Road, Winter Garden
$5,995,000
5 Beds ⋅ 6 Baths ⋅ 34787 Zip Code
Pre-Construction. To be built. To be Built, Rendering provided by master custom home builder, David Konkol of Konkol Custom Homes. However, buyer can work with builder to build any design buyer prefers (pricing to adjust accordingly). The property is spectacular waterfront acreage with boat dock on boatable, skiable Lake Roper. Acreage is 12.4 +/- with some conservation. Zoned A-1 (agricultural zoning designation). Very quiet. Very private. No HOA and close to Winter Garden and Windermere amenities as well as all theme parks.

13377 Lake Butler Boulevard, Winter Garden
$655,000
5 Beds ⋅ 3 Baths ⋅ Lake Hancock Preserve SubDv. ⋅ 34787 Zip Code
Welcome to 8018 Bowery Drive, a spacious 5-bedroom, 3-bathroom home perfectly positioned in Winter Garden right on the edge of Windermere. This layout offers flexibility and comfort for everyday living while also providing the space to entertain. Upstairs, you’ll find the private primary suite, a generous loft, a full bathroom, and three additional bedrooms, two of which offer nightly views of Disney fireworks right from the window. Downstairs features two separate living spaces, plus a conveniently located bedroom and full bathroom ideal for guests or in-laws. Step outside through the telescoping sliding glass door to enjoy a large covered porch and private backyard with no rear or side neighbors. Curb appeal shines with a paver driveway and charming wrap-around front porch. Just minutes from the 429, Disney, and all that Windermere has to offer, this home blends location, privacy, and everyday convenience. Don’t miss the chance to make this beautiful home yours!

8018 Bowery Drive, Winter Garden
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