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

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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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

$850,621
5 Beds 4 Baths Waterleigh SubDv. 34787 Zip Code
Under Construction. Waterleigh presents the Cresswell. This two-story all concrete block construction 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 a flex room perfect for work or play and downstairs powder room. The well-appointed kitchen overlooking the great room, dining room, and oversized outdoor lanai. The kitchen features quartz 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 all four 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 and separate toilet area. Two additional bedrooms share a second upstairs bathroom and linen closet for extra storage. While a fourth bedroom is complete with ensuite bathroom. Your laundry room is located on the second floor for convenience. Customize the second floor of this home to create a space that meets your needs but transforming the loft area to a fifth bedroom with full bath or Guest Suite with ensuite bathroom. Like all homes in Waterleigh, the Cresswell includes Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

11863 Shine View Lane, Winter Garden

$534,990
3 Beds 3 Baths Waterleigh SubDv. 34787 Zip Code
Waterleigh presents the Cordale. This amazing all concrete block construction single-family home features 3 bedrooms and 2.5 bathrooms optimizing living space with an open concept feel. A beautiful porch welcomes you to this home, as you enter the home you’ll find a downstairs powder room and laundry room complete with doors for privacy. The well-appointed kitchen overlooks the family room, dining room, and oversized outdoor lanai. The kitchen features quartz countertops, stainless steel appliances, spacious walk-in pantry and an island with bar seating. Bedroom one is located off the living space in the back of the home for privacy. The bedroom one-bathroom impresses with double bowl vanities, toilet room with privacy door, shower/tub space, and spacious walk in closet. As we head up to the second floor, we are greeted with a loft area and two additional bedrooms. The upstairs bedrooms share a bathroom and linen closet for extra storage. This home features a two-car garage located at the rear of the home with drop zone as you enter the first floor. Like all homes in Waterleigh, the Cordale includes Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

16816 Hobe Sound Court, Winter Garden

$549,990
3 Beds 3 Baths Waterleigh SubDv. 34787 Zip Code
Waterleigh presents the Cordale. This amazing all concrete block construction single-family home features 3 bedrooms and 2.5 bathrooms optimizing living space with an open concept feel. A beautiful porch welcomes you to this home, as you enter the home you’ll find a downstairs powder room and laundry room complete with doors for privacy. The well-appointed kitchen overlooks the family room, dining room, and oversized outdoor lanai. The kitchen features quartz countertops, stainless steel appliances, spacious walk-in pantry and an island with bar seating. Bedroom one is located off the living space in the back of the home for privacy. The bedroom one-bathroom impresses with double bowl vanities, toilet room with privacy door, shower/tub space, and spacious walk in closet. As we head up to the second floor, we are greeted with a loft area and two additional bedrooms. The upstairs bedrooms share a bathroom and linen closet for extra storage. This home features a two-car garage located at the rear of the home with drop zone as you enter the first floor. Like all homes in Waterleigh, the Cordale includes Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

12014 Shine View Lane, Winter Garden

$1,099,000
4 Beds 5 Baths Estates At Lakeview Preserve SubDv. 34787 Zip Code
New Price! Welcome to this beautifully appointed residence in Estates at Lakeview Preserve. Situated on an oversized homesite within this gated Winter Garden community, this exceptional home showcases over $100,000 in owner-added custom upgrades in addition to premium builder selections. Thoughtfully designed and meticulously maintained, it offers an incredible combination of luxury finishes, modern convenience, and resort-style outdoor living that's ready to be enjoyed from day one. Designed with both everyday living and entertaining in mind, the spacious open floor plan features a first-floor owner's suite, generously sized secondary bedrooms, a private flex room ideal for a home office, an oversized upstairs loft with an additional guest suite and full bath, and a three-car garage with included electric vehicle chargers. The heart of the home is the beautifully designed kitchen, complete with quartz countertops, premium cabinetry, abundant workspace, and an open layout that flows seamlessly into the main living area and covered lanai. Throughout the home you'll find custom built-in cabinetry, professionally designed closet systems, and motorized window treatments that add both style and functionality. The backyard was designed to be enjoyed year-round. Relax by the heated pool, entertain from the fully equipped summer kitchen, enjoy your favorite music through the built-in surround sound system, or take advantage of the convenient cabana bath after a day outdoors. Every space was thoughtfully designed to make Florida living as enjoyable as possible. This home is equally impressive behind the walls, featuring an owned solar panel system, whole-home CAT6 networking, enhanced Wi-Fi, smart TV connections, integrated surround sound, security and camera prewiring, and numerous smart-home features that provide modern convenience and energy efficiency. Living in Estates at Lakeview Preserve means enjoying gated access and outstanding community amenities including a resort-style pool, clubhouse, fitness center, playground, scenic walking trails, and beautiful lake views. Conveniently located just minutes from SR-429, Winter Garden Village, Walt Disney World, shopping, dining, and highly rated schools, the location is just as impressive as the home itself. From the extensive custom upgrades to the exceptional attention to detail, this home has been lovingly maintained and thoughtfully improved throughout. Opportunities to own a property finished to this level are few and far between. Schedule your private showing today.

4708 Weatherbell Road, Winter Garden

$899,000
4 Beds 3 Baths Winter Grove SubDv. 34787 Zip Code
Under Construction. Welcome to Winter Grove in the charming city of Winter Garden. Located 1 mile from Winter Garden Village and 3 miles from historic downtown Winter Garden. This intimate gated new community features single-family homes on large homesites without a CDD. Residents enjoy all the proximity to shopping, dining, and entertainment this area is known for. The beautifully designed 4 bedroom with an enclosed flex room, 3 bathroom, 2 car garage Coral Grand home offers the perfect blend of luxury, comfort, and functionality. As you step inside, you are greeted by a grand foyer that opens to the second floor, creating an inviting and open atmosphere. To your one side, a spacious secondary bedroom and full bath provide ideal accommodations for guests. Adjacent, an enclosed flex room offers endless possibilities – whether it’s a private office, hobby room, or a cozy reading nook. Travel deeper into the heart of the home, and you’ll find an expansive open concept layout that seamlessly connects the gathering room, kitchen, and cafe. Large windows throughout the main living areas flood the space with natural light, creating a warm and welcoming ambiance. The chef’s dream kitchen is a showstopper, complete with a built-in cooktop, stainless steel appliances, quartz countertops, and soft-close cabinetry. Step outside to enjoy the covered lanai, complete with two sliding glass doors that create a seamless transition between indoor and outdoor living. The owner's suite, located conveniently on the first floor, provides a private retreat with ample space, and is complemented by a luxurious en-suite bathroom with a spa-like walk-in shower with rain shower head, a quartz-topped dual vanity, a private water closet, and an expansive walk-in closet. The laundry room is also thoughtfully located on the first floor, complete with built-in cabinetry and a quartz trimmed utility sink, adding to the home’s convenience and ease of living. Upstairs, you’ll find two additional bedrooms, a full bathroom, and a spacious loft, offering plenty of room for everyone. Shaw wood-look luxury vinyl plank spans the first floor living areas and owner’s suite, beautiful tile flooring adds durability in the bathrooms, and laundry room, and plush, stain-resistant carpet covers the upstairs loft and secondary bedrooms. For those who appreciate the convenience of technology, this home comes equipped with a smart thermostat, video doorbell, and LED downlights, ensuring your home is as connected as it is beautiful. Experience the luxury of modern living with timeless design – schedule a tour today and see all that this exceptional home has to offer!

346 Crystal Wood Drive, Winter Garden

$739,000
3 Beds 3 Baths Winding Bay Phase 1b SubDv. 34787 Zip Code
BEAUTIFULLY UPGRADED WITH PAID-OFF SOLAR! Plus $5,000 Seller Concessions towards closing costs. This impressive 2020-built Horizon West home offers 3 spacious bedrooms, 2.5 bathrooms, plus a versatile flex room that can easily be converted to a 4th bedroom (no closet), home office, playroom, or guest space. Extensive luxury tile flooring, upgraded in 2025, flows throughout the home for a beautiful, cohesive look that's stylish, durable, and easy to maintain. Even better, the solar panels installed in 2022 will be PAID OFF by the seller at closing, giving the new owner the benefits of solar with NO SOLAR LOAN OR MONTHLY SOLAR PAYMENT and the potential for thousands of dollars in annual electricity savings. Designed for both everyday living and entertaining, the thoughtfully planned layout features an expansive open-concept great room connecting the kitchen, dining, and family areas. At the heart of the home is the chef-inspired kitchen featuring an oversized island, custom range hood, upgraded cabinetry with crown molding, and abundant counter and storage space. Crown molding, oversized baseboards, decorative columns, and custom finishes add character and architectural detail throughout. The spacious owner's suite provides a private retreat with a beautifully renovated, spa-inspired bathroom with floor to ceiling tile, fully upgraded in 2026. The secondary bedrooms are connected by a convenient Jack-and-Jill bathroom. Step outside to the screened lanai with sun shades overlooking the fully fenced backyard with attractive iron fencing. Additional features include an extended driveway, whole-home security camera system, whole-home water softener, reverse osmosis filtration in the kitchen, and a dedicated garage outlet for an additional refrigerator or freezer. With NO CARPET, extensive upgraded tile flooring, flexible living space, PAID-OFF SOLAR, modern improvements, and thoughtful upgrades already completed, this home is truly move-in ready. Simply unpack, settle in, and start enjoying everything the Horizon West lifestyle has to offer!

10750 Petrillo Way, Winter Garden

$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

$565,000
3 Beds 3 Baths Lakeshore Preserve SubDv. 34787 Zip Code
Luxury Toll Brothers End-Unit Townhome in Lakeshore Preserve! This beautifully maintained CICERO Spanish Colonial floorplan offers an open-concept layout with 10' ceilings, 8' doors, wood-look tile flooring, and abundant natural light. The gourmet kitchen features a center island, 42" cabinets, Diamond white-quartz countertops, stainless steel appliances, natural gas cooking, a large pantry, and a new oversized single-basin sink. The first-floor owner's suite includes a spacious walk-in shower and dual vanities. Upstairs you'll find two generous bedrooms, a loft, and a charming wraparound balcony. A covered walkway connects the home to the attached two-car garage. Recent upgrades include new landscaping, French doors added to the kitchen, water-resistant laminate flooring throughout the upstairs, updated quartz countertops in the kitchen and guest bath, upgraded lighting and staircase chandelier, new refrigerator, washer and dryer, saltwater softener system, patio pavers, and added garage storage. The home has been meticulously maintained with annual HVAC servicing and regular tankless water heater maintenance. Enjoy resort-style living at Lakeshore Preserve with a lakefront clubhouse, fitness center, gathering room, catering kitchen, resort pool, kayaking, and paddleboarding. Ideally located in Horizon West, just minutes from Disney, Universal, shopping, dining, and major retail centers.

8873 Fountain Palm Alley, 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

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