Winter Garden Real Estate

Winter Garden Real Estate

Welcome to Winter Garden, Florida – a charming city nestled in the heart of Orange County that perfectly blends small-town charm with modern amenities. Known for its picturesque downtown area, Winter Garden boasts a vibrant community atmosphere, making it an ideal place to call home.

As you stroll along Plant Street, you'll be captivated by the historic buildings that house an array of delightful shops, restaurants, and cafes. The bustling weekly farmers market is a local favorite, offering fresh produce, artisanal goods, and a chance to connect with neighbors. For those who appreciate the outdoors, Winter Garden is graced with beautiful parks and scenic trails, including the West Orange Trail, which invites biking, jogging, and leisurely walks amid nature’s beauty.

Winter Garden is not just about its inviting atmosphere; it also offers excellent educational opportunities with top-rated schools and a strong sense of community. Families will appreciate the safe neighborhoods and numerous recreational activities available, from youth sports leagues to community events that foster togetherness.

Additionally, Winter Garden's strategic location provides easy access to major highways, making it a convenient hub for commuting to nearby Orlando and its world-renowned attractions. Whether you’re exploring the magic of theme parks or enjoying a day at Lake Apopka, adventure is just around the corner.

With its rich history, friendly residents, and a wealth of amenities, Winter Garden is a hidden gem in Central Florida. Come and discover why so many people are proud to call this vibrant city home!

Newest Listings in Winter Garden

14026 Frasier Street, Winter Garden

14026 Frasier Street, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Highland Ridge SubDv. ⋅ 34787 Zip Code

SELLER OFFERING $10,000 TOWARDS BUYER CLOSING COST WITH AN ACCEPTABLE OFFER!! Welcome to this beautiful 2023-built home in the desirable Highland Ridge community of Winter Garden! Featuring 3 bedrooms, 2.5 bathrooms, and 1,985 square feet of thoughtfully designed living space, this home offers the perfect combination of modern comfort, functionality, and energy efficiency. Step inside and discover a bright, spacious open-concept main floor, ideal for everyday living and entertaining. The inviting covered front porch adds charm and provides a wonderful place to relax and enjoy the Florida lifestyle. Upstairs, you’ll find a versatile loft perfect for gathering and relaxation, along with a private primary suite offering comfort and privacy. The additional bedrooms provide flexibility for family members or guests. Built by Meritage Homes, known for its innovative energy-efficient features, this property is designed with comfort and potential energy savings in mind. Additional highlights include a two-car garage and access to the community pool. Location is another outstanding feature! Just a short walk from the new Ovation Elementary School and the Flamingo Crossings shopping center, offering a variety of restaurants, fast-casual dining options, grocery stores, a fitness center, and convenience stores, making everyday living exceptionally convenient. The property also provides easy access to major roadways and Orlando’s world-famous attractions. Don’t miss your chance to own a nearly new home in one of the Orlando area’s most desirable locations. Schedule your private showing today!

14026 Frasier Street, Winter Garden

2010 Boss Hewett Street, Oakland

2010 Boss Hewett Street, Oakland

5 Beds ⋅ 4 Baths ⋅ Hull Island/Oakland Ph 2 SubDv. ⋅ 34787 Zip Code

Beautiful 2022-built home in Hull Island featuring 5 bedrooms, 4 full bathrooms, approximately 3,781 heated square feet, a private pool, and a two-car garage. Open-concept living with a gourmet kitchen, quartz countertops, a spacious loft, and two primary suites, including one on the first floor. Community amenities include a pool, trails, playground, dog park, and private dock. Buyer to verify all measurements, HOA terms, and property details.

2010 Boss Hewett Street, Oakland

9380 Bolshoi Alley, Winter Garden

9380 Bolshoi Alley, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Tribute/Ovation SubDv. ⋅ 34787 Zip Code

SELLER PROVIDING UP TO $10,000 TOWARD BUYER CLOSING COSTS! Welcome to this nearly NEW townhome in the heart of highly desirable Horizon West! Built in 2025, this 3-bedroom, 2-and-a-half-bathroom residence offers the appeal of newer construction in one of Central Florida’s fastest-growing communities. Enjoy the convenience of having Publix and an expanding selection of shopping, dining, and everyday essentials just across the street! The unit is equipped with upgraded QUARTZ countertops, tile throughout the first floor & a cozy private courtyard. The home’s prime location also provides easy access to State Road 429, making commuting throughout Central Florida a breeze. Just minutes away, the popular Hamlin area offers an exciting mix of restaurants, retail, entertainment, and recreational opportunities. Whether you’re searching for a primary residence or a low-maintenance lifestyle, this townhome offers an excellent combination of location, convenience, and modern living. With construction completed in 2025, buyers can enjoy the benefits of a newer home without the wait of building from the ground up. Don’t miss your opportunity to own a nearly new townhome in the heart of Horizon West!

9380 Bolshoi Alley, Winter Garden

13537 Splashing Isla Drive, Winter Garden

13537 Splashing Isla Drive, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Del Webb Oasis Ph 2 SubDv. ⋅ 34787 Zip Code

Virtually Staged. Welcome home to carefree villa living in the beautiful 55+ community of Del Webb Oasis. Follow a delightful pavered walkway past lush landscaping to reach the covered front porch. Stepping inside reveals a generous foyer with plank tile flooring that extends throughout all living/wet areas right up to carpeted bedrooms. Inside the spectacular kitchen you will find 42" uppers, gorgeous quartz countertops, subway tile backsplash, tall crown cabinet molding, waste-basket pull out, soft close drawers, double roll-out trays, whirlpool appliances, an island with storage and electric, excellent lighting and attractive matte black hardware. Just off the kitchen is the cafe or dining area which then flows into the gathering room or living room. Three clerestory windows provide natural light into the living room which also has a floor outlet and LED downlights illuminating well the ebb and flow of life lived to the fullest. The split floor plan places the primary suite at one end of the home with two guest bedrooms and a guest bath at the other end. With a window view into the peaceful backyard, the spacious primary bedroom adjoins an en suite bathroom complete with a shower (note the built-in seat and glass shower door), dual sinks, water closet, linen closet and enormous walk-in closet. Two guest bedrooms can serve as office, den, library, craft room or hobby space in addition to providing a comfortable space for visiting guests. An attractive tile-surround for the tub/shower in the guest bathroom complements the single vanity and finishes perfectly. Near the door leading to the 2-car garage is the laundry room with pocket door, washer/dryer, ventilated shelves, CAT6 Telecom Data Port and a transom-style window. Triple sliders open to the covered and extended pavered lanai. Keyless entry for the garage. 2" faux wood blinds at all functional windows. A 5" Carbon Clean MERV 16 filter with Cabinet enhances the HVAC system. Adjacent to the home is a paved walking trail. Community amenities include an active, sprawling Clubhouse, resort-style pool as well as pickle ball and tennis courts. HOA fees also include exterior maintenance, landscaping, irrigation repairs, exterior painting and roof replacement. Schedule your visit to see all that this home has to offer today!

13537 Splashing Isla Drive, Winter Garden

730 Magnolia Street, Winter Garden

730 Magnolia Street, Winter Garden

5 Beds ⋅ 3 Baths ⋅ Winter Gdn Manor SubDv. ⋅ 34787 Zip Code

Under Construction. Virtually Staged. Under Construction. ***NEW CONSTRUCTION LUXURY HOME*** 5 bedrooms / 2.5 bathrooms ***Two-car garage ***Two-story home ***Luxurious glass entry doors ***Grand foyer featuring a beautiful, elegant chandelier ***Staircase with a wrought-iron railing ***Foyer accented with custom decorative wall paneling ***Open-concept layout: integrated living room, dining area, and kitchen ***Large quartz kitchen island ***High-end KitchenAid appliances ***Custom kitchen range hood ***Walk-in pantry ***Indoor laundry room ***Primary suite located on the ground floor ***Bedrooms 2, 3, 4, and 5 located upstairs, alongside a spacious loft area—perfect as a family living space ***Elegant 8- panel doors with detailed trim ***8-inch baseboards and crown molding ***Foam insulation for enhanced energy efficiency ***Large covered rear patio ***No Homeowners Association (HOA) fees ***Generous lot size (50x150 feet), VINYL FENCED for privacy with ample space to add a private pool or a detached workshop ***Located in a non-flood zone ***North-facing orientation*** Prime location: just minutes from downtown Winter Garden, Winter Garden Village, the Winter Garden Trail, and Disney World. Easy access to the Florida Turnpike and toll roads 408 and 429, offering a convenient commute to the airport and downtown Orlando.

730 Magnolia Street, Winter Garden

740 Magnolia Street, Winter Garden

740 Magnolia Street, Winter Garden

5 Beds ⋅ 3 Baths ⋅ Winter Garden Manor SubDv. ⋅ 34787 Zip Code

Virtually Staged. Under Construction. ***NEW CONSTRUCTION LUXURY HOME*** 5 bedrooms / 2.5 bathrooms ***Two-car garage ***Two-story home ***Luxurious glass entry doors ***Grand foyer featuring a beautiful, elegant chandelier ***Staircase with a wrought-iron railing ***Foyer accented with custom decorative wall paneling ***Open-concept layout: integrated living room, dining area, and kitchen ***Large quartz kitchen island ***High-end KitchenAid appliances ***Custom kitchen range hood ***Walk-in pantry ***Indoor laundry room ***Primary suite located on the ground floor ***Bedrooms 2, 3, 4, and 5 located upstairs, alongside a spacious loft area—perfect as a family living space ***Elegant 8-panel doors with detailed trim ***8-inch baseboards and crown molding ***Foam insulation for enhanced energy efficiency ***Large covered rear patio ***No Homeowners Association (HOA) fees ***Generous lot size (50x150 feet), VINYL FENCED for privacy with ample space to add a private pool or a detached workshop ***Located in a non-flood zone ***North-facing orientation*** Prime location: just minutes from downtown Winter Garden, Winter Garden Village, the Winter Garden Trail, and Disney World. Easy access to the Florida Turnpike and toll roads 408 and 429, offering a convenient commute to the airport and downtown Orlando.

740 Magnolia Street, Winter Garden

2139 Tillman Avenue, Winter Garden

2139 Tillman Avenue, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Bronsons Landing SubDv. ⋅ 34787 Zip Code

STOP YOUR SCROLL!!! It's not everyday a GORGEOUS home inside the beautiful gated community of Bronson's Landing is available but this Pool Home offers SO MUCH! This 4 bedroom PLUS OFFICE and POSSIBLE 5th BEDROOM home has 4 FULL bathrooms with multiple living spaces, multiple dining areas as well as an extra large 3 car garage. At the heart of the home is the spacious kitchen with an island, perfectly positioned between the main living areas and designed for both everyday life and entertaining. You’ll find granite counter tops, a large center island, double ovens, plenty of cabinetry, and a pantry. One of the best features is that the primary suite and three additional bedrooms are all located on the main floor. The primary bedroom feels like its own private retreat on it's own side of the house with two walk-in closets, dual vanities, a soaking tub, and separate shower. Being a split floor plan, 2 bedrooms share a Jack-and-Jill bathroom that makes this home super functional. This home can easily handle generational living. Upstairs, the over-sized bonus room with its own full bathroom gives you even more possibilities. Use it as a game room, movie room, guest suite, home gym, second office, or even a possible 5th bedroom. There is plenty of flexibility to make the space work for your lifestyle. The backyard is where the Florida lifestyle really shines! Step outside to your own private oasis with a screened saltwater pool, covered lanai, paver deck, and convenient pool bath. The home backs to a beautiful tree-lined green space, giving you extra privacy and a peaceful setting with no home directly behind you. Imagine starting the morning with coffee by the pool, spending the afternoon soaking up the Florida sunshine, and ending the evening relaxing under the lanai. And YES! Location matters! Bronson’s Landing is a sought-after gated community in one of Winter Garden’s most desirable areas, with access to highly regarded schools and an amazing Central Florida location. You’re close to Winter Garden Village, shopping, dining, 429, and all the charm of Historic Downtown Winter Garden. ALSO! Walt Disney World is just a short drive away, making spontaneous trips to the parks, dinner at Disney Springs, or a night watching fireworks that much easier! This home gives you the space of a true family home, the privacy of a beautiful gated community, your own Florida pool, and easy access to everything that makes Winter Garden and the Disney area such a MAGICAL place to live. If you’ve been waiting for a home that offers space, flexibility, privacy with a pool, and a fantastic location, THIS IS THE ONE!

2139 Tillman Avenue, Winter Garden

14656 Pylon Court, Winter Garden

14656 Pylon Court, Winter Garden

7 Beds ⋅ 7 Baths ⋅ Isles/Lk Hancock Ph Iii SubDv. ⋅ 34787 Zip Code

Welcome to this beautiful lake-view home in the desirable, gated Isles of Lake Hancock community in Horizon West / Winter Garden! This spacious 7-bedroom, 6.5-bathroom home offers approximately 4,634 square feet of living space on an oversized 0.43-acre lot, with beautiful lake views from both the front and back of the property. The first floor features a spacious primary suite with a sitting area and his-and-hers walk-in closets, three additional bedrooms with bathrooms, and a separate office perfect for working from home, and a formal dining area for family meals and entertaining.The split-bedroom floor plan offers added privacy and flexibility. Upstairs, you'll find three more bedrooms, two bathrooms, and a den, providing plenty of space for family and guests. The home also offers two separate garage spaces, with one currently enclosed and used as a gym that can be converted back into a garage if desired. Enjoy Florida living with a screened-in pool, summer kitchen, solar panels, and beautiful sunset views over the lake. Residents of this gated community enjoy tennis courts, playground and a private boat ramp. Lake Hancock is a nationally recognized water-skiing destination that hosts world-class tournaments. Located in the sought-after Horizon West / Winter Garden area, the community offers convenient access to Walt Disney World, shopping, dining, upscale golf courses, top-rated schools, and SR-429. With plenty of space, beautiful lake views, and a great location, this home has so much to enjoy. Schedule your private showing today!

14656 Pylon Court, Winter Garden

5705 New Independence Parkway, Winter Garden

5705 New Independence Parkway, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Signature Lakes - Phase 2 SubDv. ⋅ 34787 Zip Code

WELCOME HOME TO 5705 NEW INDEPENDENCE PARKWAY! Discover the perfect blend of COMFORT, CHARM, and RESORT-STYLE LIVING in the highly desirable INDEPENDENCE / SIGNATURE LAKES COMMUNITY of WINTER GARDEN, FLORIDA! This inviting 3-BEDROOM, 2.5-BATH TOWNHOME offers 1,751 SQ. FT. OF LIVING SPACE, a PRIVATE REAR-ENTRY 2-CAR GARAGE, and a wonderful opportunity to enjoy everything that makes Central Florida living so special. From the moment you arrive, the CHARMING FRONT PORCH welcomes you home. Step inside to discover a bright, OPEN-CONCEPT FLOOR PLAN filled with NATURAL LIGHT, creating a comfortable setting for everyday living, entertaining friends, or simply unwinding after a long day. The SPACIOUS KITCHEN features GRANITE COUNTERTOPS, generous cabinet storage, and plenty of room to gather, while UPDATED LAMINATE FLOORING adds warmth throughout the main living areas. A NEWER HVAC SYSTEM INSTALLED IN 2025 provides an added touch of comfort and peace of mind. Upstairs, the PRIMARY SUITE offers a relaxing retreat with a PRIVATE ENSUITE BATHROOM and WALK-IN CLOSET. Two additional bedrooms provide flexible space for guests, hobbies, or a HOME OFFICE. Whether you're enjoying your morning coffee on the FRONT PORCH, hosting dinner with loved ones, or relaxing on the PRIVATE PATIO, this home offers room to create lasting memories. Life in INDEPENDENCE is about so much more than the home itself! Residents enjoy an exceptional collection of RESORT-STYLE AMENITIES, including TWO COMMUNITY POOLS, FITNESS CENTERS, a CLUBHOUSE, PARKS, PLAYGROUNDS, DOG PARKS, TENNIS AND BASKETBALL COURTS, SCENIC WALKING TRAILS, and COMMUNITY LAKE ACCESS. Neighborhood gatherings and community events create opportunities to connect, unwind, and truly feel at home. And the LOCATION is equally impressive! Nestled in the heart of HORIZON WEST, you're conveniently located near HAMLIN TOWN CENTER, HISTORIC DOWNTOWN WINTER GARDEN, the WEST ORANGE TRAIL, and WALT DISNEY WORLD, with easy access to shopping, dining, entertainment, major roadways, and area schools. LOCATION, COMFORT, COMMUNITY, AND RESORT-STYLE LIVING — ALL IN ONE PLACE! With 3 BEDROOMS, 2.5 BATHROOMS, 1,751 SQ. FT., A PRIVATE 2-CAR GARAGE, and an incredible array of NEIGHBORHOOD AMENITIES, 5705 NEW INDEPENDENCE PARKWAY is more than just a place to live — it's a place to feel at HOME. WELCOME HOME TO INDEPENDENCE, WINTER GARDEN!

5705 New Independence Parkway, Winter Garden

17361 Bal Harbour Drive, Winter Garden

17361 Bal Harbour Drive, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Waterside/Johns Lk-Ph 2b SubDv. ⋅ 34787 Zip Code

Welcome to this spacious 4-bedroom, 2.5-bath home offering approximately 2,931 square feet in the desirable Waterside at Johns Lake community. The open floor plan features a versatile front room ideal for a home office, formal dining room, or additional living space. The kitchen offers granite countertops, stainless-steel appliances, abundant cabinetry, and an open connection to the family room. An additional flex room provides even more space for entertaining, relaxing, or creating a game room. All four bedrooms are located upstairs, including a generous primary suite with a walk-in closet, dual-sink vanity, and walk-in shower. Additional features include an interior laundry room, attached two-car garage, and a covered paver lanai for enjoying the Florida lifestyle. Community amenities include a pool, clubhouse, fitness center, playground, sidewalks, and access to Johns Lake. Conveniently located near shopping, dining, Downtown Winter Garden, Hamlin, and FL-429. New photos coming soon!!!

17361 Bal Harbour Drive, Winter Garden

15311 Calming Balsam Alley, Winter Garden

15311 Calming Balsam Alley, Winter Garden

5 Beds ⋅ 5 Baths ⋅ Enclave/Hamlin SubDv. ⋅ 34787 Zip Code

Shows like a model home! This immaculate 5-bedroom, 4.5-bath home with nearly 3,000 sq ft in Enclave at Hamlin is extensively upgraded with luxury finishes throughout! Rare, completely separate Guest/Mother-in-Law Suite above the detached garage, featuring a private entrance, full bath, kitchenette, and spacious living area! The stunning main home features soaring 24-foot ceilings, a gourmet kitchen with quartz countertops, 42" cabinetry, natural gas cooking, designer lighting, 8-foot doors, brand-new premium carpeting, fresh paint, custom closet built-ins, and an upgraded primary shower. First-floor en suite, beautiful hardwood staircase, and abundant natural light! Enjoy Disney fireworks views, a spacious screened lanai, fenced yard, and greenbelt views. Steps from the community pool, playground, Hamlin shopping, Horizon West Regional Park, and library. Truly exceptional condition with upgrades that set this home apart! Available fully furnished!

15311 Calming Balsam Alley, Winter Garden

5513 New Independence Parkway, Winter Garden

5513 New Independence Parkway, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Independence / Signature Lakes Ph 02 SubDv. ⋅ 34787 Zip Code

Nestled in the heart of the desirable Winter Garden, this beautifully updated 3-bedroom, 2-bathroom SALTWATER POOL HOME offers 1,920 square feet of thoughtfully designed living space, modern elegance, and an exceptional resort-style lifestyle! From the moment you arrive, you’ll fall in love with the picturesque curb appeal, lush landscaping, charming brick-paver walkway, and inviting covered front porch. Step inside to discover a bright, open-concept floor plan featuring beautiful bamboo flooring, abundant natural light, and inviting living spaces perfect for everyday comfort and entertaining. The heart of the home is the stunning kitchen, completely remodeled in 2019! Featuring gorgeous quartz countertops, rich cabinetry, stainless steel appliances, stylish pendant lighting, and an expansive island with seating, this space is designed for gathering and making memories. A charming, sun-filled dining nook completes the picture! Your own private backyard oasis awaits! Step through beautiful French doors to your sparkling SALTWATER POOL, surrounded by an expansive screened enclosure and spacious covered lanai. Whether you're enjoying a refreshing afternoon swim, hosting weekend gatherings, or relaxing in the shade, this outdoor retreat makes every day feel like a vacation! Additional highlights include a convenient rear-entry garage with a beautifully finished epoxy floor. The lifestyle doesn't stop at your front door! Enjoy RESORT-STYLE COMMUNITY AMENITIES and a vibrant calendar of year-round events, including themed movie nights, ice cream socials, fireworks, and seasonal celebrations. Even better, the HOA includes internet and cable. Ideally located in the beautiful Winter Garden, walkable to schools, shopping, dining, entertainment, and conveniently located to Central Florida attractions, this home offers the perfect blend of modern comfort, neighborhood charm, and Florida living. More than a home....it's a lifestyle! Schedule your private showing today! *Wine fridge and weather station on the lanai screen does not convey.

5513 New Independence Parkway, Winter Garden

Start Your Search

How much is your home worth?

Get instant property value now!