Explore Homes for Sale in Winter Garden, FL
Map Search for Winter Garden, FL Homes for Sale

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

  Advanced Search   Market Reports   Home Value   Connect

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.

Search Winter Garden, FL by Lifestyle
Search Winter Garden, FL by Price
Search Winter Garden, FL by Bedrooms
Search Winter Garden, FL by Bathrooms
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

$275,000
2 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
This first-floor condo in the gated Southern Pines community offers 1,216 square feet of well-designed living space with an open floor plan, private outdoor area, and two full bathrooms. Making it a strong fit for first-time buyers, down-sizers, or investors. The layout connects the living area directly to the outdoor space, and both bedrooms provide solid closet storage. The kitchen offers ample counter space and cabinetry for everyday living. Southern Pines residents enjoy access to a pool and spa, fitness center, indoor basketball and racquetball courts, tennis and pickleball courts, a media room, billiards lounge, business center, BBQ area, car wash station, and playground. All within a secure, gated community. Located minutes from the West Orange Trail, Johns Lake, SR 408, and the Florida Turnpike, with top-rated Orange County schools nearby and Orlando International Airport 23 miles away. Winter Garden’s dining and retail corridors are within easy reach. Low-maintenance living with resort-style amenities in a location that works. Schedule your showing today.

1300 Eastern Pecan Place Unit 102, Winter Garden
$471,000
3 Beds ⋅ 3 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Toll Brothers New Construction at Winter Garden Horizonwest. Our Crowley Townhome features a covered entry that leads to an open and expansive living space, kitchen, and dining. The home features a spacious courtyard with access to the detached 2 cars garage. The Primary Bedroom is highlighted by a large walk-in closet and a private bath with dual vanities and separate shower. There's still time to personalize this home with your preferred design upgrades.

12830 Sunset Walk Drive, Winter Garden
$890,000
4 Beds ⋅ 4 Baths ⋅ Oakland Parka SubDv. ⋅ 34787 Zip Code
Virtually Staged. Imagine 1338 Union Club Dr, a residence recently updated with partial flooring replacement. Its kitchen includes all stainless steel appliances, an accent backsplash, and an island, while the primary bedroom features a walk in closet and the primary bathroom provides double sinks. Beyond, a covered patio overlooks an in ground pool within a fully fenced in backyard. This updated residence provides modern comfort and an inviting outdoor space.. Included 100-Day Home Warranty with buyer activation

1338 Union Club Drive, Winter Garden
$799,900
5 Beds ⋅ 4 Baths ⋅ Ravenna Ph 1 SubDv. ⋅ 34787 Zip Code
BUYER INCENTIVES: Offering $10,000 in "Cash Flex" incentives to be used toward a price reduction, buyer closing costs, or an interest rate buy-down with a full-price offer! PLUS, get an additional $5,000 lender contribution toward a rate buy-down when using the seller’s preferred lender—that’s up to $15,000 in total savings! Welcome to the pinnacle of luxury at 7687 Bowery Dr, located within the highly desirable, master-planned Ravenna community of Horizon West. This single-story masterpiece offers a rare combination of upscale lifestyle flexibility and long-term value, situated on an expansive 0.48-acre premium lot—one of the largest in the entire community! With NO REAR NEIGHBORS, a serene conservation backdrop, and nightly views of spectacular theme park fireworks right from your own property, this home is a true sanctuary. Grand 8-foot double front doors welcome you into a masterfully crafted, light-filled layout boasting 5 bedrooms, 4 full bathrooms, and over 3,170 square feet of high-end living space. INTERIOR HIGHLIGHTS: Designed for both grand entertaining and comfortable everyday living, the main areas showcase stunning 8"x36" designer tile flooring. NO CARPET: The home features durable tile and waterproof luxury vinyl plank flooring throughout for ultimate ease of maintenance. At the heart of the residence is a chef’s dream kitchen, anchored by a massive 11-foot center island with seating for five. It comes fully equipped with 42" light gray cabinetry with crown molding, gleaming white quartz countertops, premium stainless steel appliances, double wall ovens, and a drop-in cooktop. THOUGHTFUL FLOOR PLAN FLEXIBILITY: The luxurious primary suite serves as a true retreat, featuring elegant tray ceilings, dual walk-in closets, and a spa-like 5’x8’ frameless glass shower with dual shower heads. For maximum functionality, the layout features a Jack-and-Jill bathroom between bedrooms 2 and 3, plus a private en-suite bathroom for bedroom 5—making it perfectly optimized as a multi-generational retreat or a private guest wing. OUTDOOR OASIS & PEACE OF MIND: Step outside to your massive backyard looking out directly over a protected conservation area, providing unparalleled privacy and beautiful natural views. The neighborhood offers premium community amenities including a pool and playground, all with low HOA fees and NO CDD! PRIME LOCATION: Perfectly positioned in Winter Garden, you are zoned for top-rated public schools and sit just minutes from Hamlin Town Center shopping, dining, and major transport corridors (429, 408, and Florida’s Turnpike). Enjoy a swift, seamless commute to downtown Orlando, Disney World, and Universal Studios. Schedule your private showing today and discover the ultimate Central Florida lifestyle!

7687 Bowery Drive, Winter Garden
$375,000
3 Beds ⋅ 3 Baths ⋅ Signature Lakes Ph 3b-6 SubDv. ⋅ 34787 Zip Code
Well keep and move in ready corner unit townhouse at the beautiful signature lake at winter garden ,brand new vinyl plank floor at the first floor this 3 bedroom and 2.5 bath room townhouse have 1750 sqft and feature big court yard between the garage you can enjoy the outdoors living on the big courtyard , the oversize front porch is welcome to their new owner , the first floor feature all ceramic title ,have living room and the work space at the front the house and the the kitchen offer gorgeous granite counter tops , wood cabinet and pendant lighting , open up the family room , also have powder room at the first floor , upstair you have 3 bedroom big walk in closet at the master bedroom and dual sink at the master bathroom and one more full bath to share for the other bedroom , signature lake is sought after community at winter garden , feature resort style pool and state of the art gym and club house many event for the residence for the community , grade A school . it is close located next to the Hamlin shopping center and the winter garden village close to 429 and 535 , the HOA fee include cable include HBO and high speed internet from sepcturm . , this is turn key townhouse is ideal for who enjoy low maintenance lifestyle .

14903 Driftwater Drive, Winter Garden
$480,000
2 Beds ⋅ 2 Baths ⋅ Grova Residence & Spa Hotel Condo 3 SubDv. ⋅ 34787 Zip Code
Welcome to The Grove Resort & Water Park, a luxury vacation condo-hotel community offers owner privacy and convenience. Located 5 minutes from Walt Disney World, ownership of the largest 2-bedroom provides a family friendly place to vacation and relax. Let's discuss more about this 2B When you step through the door, you enter directly into the living space. The unit features in-unit laundry, with full-size washer and dryer. The kitchen is well-equipped with all major appliances, so you can certainly cook here if desired. The living space is spacious, and also includes a dining area. You can be making $ on the day of closing! Financial statements are available! Please note that this is a condo-hotel, so you could not live here full time due to zoning restrictions

14501 Grove Resort Avenue Unit 3425, Winter Garden
$789,900
4 Beds ⋅ 4 Baths ⋅ Orchard Hills Ph 3 SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully upgraded home in the heart of Winter Garden. Featuring luxury vinyl flooring throughout with no carpet, this home offers a clean, modern feel and a functional layout designed for everyday living and entertaining. The main living area showcases custom millwork and built-in details, while the elegant powder room adds a touch of sophistication. With over $150,000 in improvements, this home showcases a level of quality rarely found at this price point. Designed and improved by an owner who planned to live in the home long-term, no expense was spared in creating a space that is both beautiful and highly functional. The gourmet kitchen serves as the heart of the home, offering ample space for cooking and gathering. Step outside to a fully equipped outdoor living area featuring a complete summer kitchen with sink, cooktop, refrigerator, built-in grill, and a traditional parrilla grill. With no rear neighbors, the backyard provides added privacy and the perfect setting for relaxing or entertaining guests. Additional improvements include a whole-home water softener system and numerous thoughtful enhancements throughout the property. Located just steps from the community clubhouse, residents enjoy access to resort-style amenities including a swimming pool, fitness center, social hall with event kitchen, playground, sports courts, walking and biking trails, dog park, community green spaces, and parks. Conveniently located near shopping, dining, and major roadways, and zoned for highly rated A-rated schools, this home offers an exceptional opportunity to enjoy the best of Winter Garden living. PROPERTY FEATURES LEASED SOLAR PANELS. THE SOLAR LEASE MUST BE ASSUMED BY THE NEW BUYER PRIOR TO CLOSING. THE CURRENT OWNER’S MONTHLY SOLAR PAYMENT IS $145, PROVIDING SOLAR ENERGY THAT HELPS OFFSET ELECTRICITY USAGE AND REDUCE TRADITIONAL UTILITY COSTS.

5024 Palmetto Park Drive, Winter Garden
$1,495,000
6 Beds ⋅ 6 Baths ⋅ Waterside/Johns Lake Ph 1 SubDv. ⋅ 34787 Zip Code
An Irreplaceable Gated Estate: Unmatched Scale, Double-Lot Privacy, & Private Oasis Behind the gates of the highly coveted Waterside community, 16614 Harbor Sail Way breaks the mold of standard luxury builds. This is not a high-density, cookie-cutter residence; it is an established, substantial family estate defined by an extraordinary sense of space, meticulous craftsmanship, and structural authority. Positioned beautifully on an expansive, premium lot that nearly doubles the community average, this rare property offers a refined lifestyle designed for those who value space to breathe, long-term permanence, and effortless entertaining. While typical Mansfield floor plans in the neighborhood occupy a standard lot, this home’s visionary owners secured the adjacent parcel, resulting in a commanding 14,973-square-foot footprint. This unique layout introduces a majestic private turning circle with dedicated parking for an additional six vehicles (bringing total driveway capacity to ten)—ideal for hosting executive gatherings or multi-generational families. Beyond the striking courtyard entry, the residence spans an impressive 4,882 square feet of meticulously maintained living space, delivering structural scale that effortlessly handles the demands of modern family life. The heart of the home centers on a dramatic great room bathed in natural light, seamlessly connecting to a gourmet kitchen equipped with premium finishes and gas cooking. Every corner of the main level emphasizes functional luxury, including a private home office, formal dining room, a secluded guest suite, and a magnificent primary sanctuary. Ascending to the second level reveals a sprawling, open flex room suspended over the main living area that opens to a fully enclosed, private balcony, creating an incredible architectural anchor. This level features four additional large bedrooms and media room, offering families the chance to spend time together, or unwind in complete peace. For ultimate daily convenience, a built-in central vacuum system services the ground floor of the home. While neighboring homes may provide "room for a future pool," this estate delivers the ultimate outdoor lifestyle immediately. The west-facing backyard is a private, sun-drenched sanctuary featuring a spectacular custom salt-water pool and integrated spa. Surrounded by extended paver decking and lush, manicured grassed areas made possible by the expanded double-lot footprint, this outdoor space offers complete privacy with no direct rear neighbors—perfect for enjoying vibrant Central Florida sunsets. Living in Waterside means enjoying a resort-style lifestyle with access to a premier clubhouse, fitness center and community pool. You are uniquely positioned just minutes from Horizon West’s top-rated schools (Hamlin Elementary/Middle), West Orange (High), the charm of downtown Winter Garden, major executive corridors (SR-429, Turnpike), and premier dining and shopping. This is more than a home; it is a strategic asset of scarcity, privacy, and generational quality. Schedule your private tour to experience it firsthand.

16614 Harbor Sail Way, Winter Garden
$489,990
4 Beds ⋅ 2 Baths ⋅ Stoneybrook West 47/78 SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully maintained 4-bedroom, 2-bath home located in the highly desirable gated golf community of Stoneybrook West in Winter Garden. This move-in-ready residence features an open and spacious floor plan with separate living and dining areas, high ceilings, abundant natural light, and ceramic tile throughout. The upgraded kitchen offers granite countertops, ample cabinet space, and all appliances are included. The spacious primary suite features a large walk-in closet and an updated bathroom with skylights, dual vanities, a garden tub, and a separate shower. Enjoy outdoor living in the fully fenced backyard with a large patio, perfect for entertaining or relaxing. Recent updates and meticulous care make this home a true standout. Roof replaced in 2022. Property comes with solar panels. Residents enjoy resort-style amenities including a community pool, fitness center, tennis and basketball courts, playgrounds, lake access, fishing pier, boating, and 24-hour guarded gate security. Conveniently located near top-rated schools, shopping, dining, major highways, downtown Winter Garden, and Orlando's world-famous attractions. Don't miss this exceptional opportunity—schedule your private showing today!

2227 Oakington Street, Winter Garden
$289,000
2 Beds ⋅ 2 Baths ⋅ Joe Louis Park First Add SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully renovated 2-bedroom, 2-bath home in the heart of Winter Garden. Blending modern updates with timeless charm, this move-in-ready residence offers stylish finishes, functional living spaces, and a convenient location just minutes from Historic Downtown Winter Garden. Step inside to discover a bright, refreshed interior featuring contemporary flooring, recessed lighting, updated fixtures, and an open, inviting atmosphere. The fully remodeled kitchen showcases elegant white shaker cabinetry, sleek countertops, stainless steel appliances, and modern hardware, creating a clean and sophisticated space for everyday living and entertaining. The renovated bathrooms feature designer-inspired finishes, including a spacious walk-in shower with stunning marble-look tile, upgraded fixtures, and a modern vanity. Thoughtful updates throughout the home provide a fresh, cohesive look while maintaining comfort and functionality. Outside, enjoy a spacious lot shaded by mature trees, offering room for outdoor entertaining, gardening, pets, or future expansion. Fresh exterior improvements and landscaping enhance the home's curb appeal, while the absence of HOA restrictions provides added flexibility and freedom. Conveniently located near shopping, dining, parks, the West Orange Trail, major highways, and all that Downtown Winter Garden has to offer, this turnkey property presents an exceptional opportunity for homeowners and investors alike. Don't miss your chance to own a beautifully updated home in one of Central Florida's most sought-after communities.

1701 E Bay Street, Winter Garden
$890,000
5 Beds ⋅ 5 Baths ⋅ Waterleigh SubDv. ⋅ 34787 Zip Code
UNBEATABLE OPPORTUNITY IN WATERLEIGH! This stunning move-in ready home offers the perfect combination of luxury, privacy, and Florida lifestyle. Enjoy a premium lot, spacious open floor plan, designer finishes, and access to resort-style amenities including pools, fitness center, walking trails, and parks. Ideally located near top-rated schools, shopping, dining, major highways, and Disney. Homes like this at this value don't last! Priced to sell and ready for a quick closing—schedule your private showing today before this incredible opportunity is gone!

8768 Sonoma Coast Drive, Winter Garden
$1,375,000
4 Beds ⋅ 4 Baths ⋅ Waterleigh Ph 1a SubDv. ⋅ 34787 Zip Code
Now offered at $1,375,000 following a $124,000 price adjustment. This luxury residence presents an exceptional opportunity to own a beautifully designed home at its newly adjusted price. 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.

8530 Bayview Crossing Drive, Winter Garden
Start Your Search