Winter Garden Homes with Florida Architectural style

Winter Garden Homes with Florida Architectural style

Welcome to Winter Garden, Florida – a picturesque city nestled in the heart of Orange County, where charm meets modern living. Known for its vibrant downtown area, Winter Garden boasts a rich history that dates back to the 1800s, making it a delightful blend of old-world charm and contemporary conveniences. With its lush landscapes, beautiful lakes, and an array of outdoor activities, it’s no wonder that Winter Garden has become a sought-after destination for families and professionals alike.

One of the standout features of Winter Garden is its stunning homes that reflect the quintessential Florida architectural style. From cozy bungalows to sprawling estates, the homes here are designed to embrace the natural beauty of the Sunshine State. Picture yourself in a charming Craftsman-style home with a wrap-around porch, or perhaps a Mediterranean villa adorned with terracotta tiles and lush gardens. The architectural diversity offers something for everyone, with many properties featuring open floor plans, large windows, and outdoor living spaces that seamlessly blend indoor and outdoor lifestyles.

Winter Garden is not just about beautiful homes; it’s also a community that thrives on connection and engagement. With farmer’s markets, seasonal festivals, and a vibrant arts scene, residents enjoy a lifestyle that is both active and enriching. The nearby West Orange Trail offers miles of scenic pathways for walking, biking, and exploring the great outdoors.

If you’re looking to settle in a place that combines Florida’s architectural flair with a warm community spirit, Winter Garden is the perfect choice. Explore the possibilities and discover your dream home in this enchanting city!

Newest Winter Garden Homes with Florida Architectural style

5 Beds ⋅ 4 Baths ⋅ Winter Grove SubDv. ⋅ 34787 Zip Code

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. Discover the perfect blend of luxury, comfort, and convenience in this stunning Mahogany Grand home. Thoughtfully designed for both everyday living and entertaining, this exceptional two-story residence offers 5 bedrooms, 4 full bathrooms, a loft, and a spacious 3-car garage. The open-concept living area seamlessly connects the gourmet kitchen, café, and gathering room, creating an expansive and inviting space. Soaring ceilings and an elegant tray ceiling enhance the sense of openness, while a large pocket sliding glass door extends the living space onto the covered lanai, filling the home with natural light and creating the perfect blend of indoor and outdoor living. At the heart of the home, the gourmet kitchen showcases stacked soft-close cabinetry, quartz countertops, and built-in Whirlpool stainless steel appliances, including a natural gas cooktop, range hood, and a refrigerator. Whether preparing everyday meals or hosting special gatherings, this kitchen is designed to impress. Privately situated in the back corner of the home, the spacious owner's suite offers a peaceful retreat and features an owner's suite extension, providing additional space for a sitting area, fitness nook, workspace, or whatever best suits your lifestyle. The spa-inspired en suite bath includes a walk-in closet, linen closet, walk-in shower with a rain shower head, and a private enclosed water closet. Three additional first-floor bedrooms and two bathrooms provide comfort and privacy for everyone. Upstairs, enjoy an additional 709 square feet of flexible living space, complete with a generous loft, private fifth bedroom, and full bathroom, making it ideal for a media room, guest suite, home office, or multigenerational living. Completing the home is a spacious 3-car garage with ample room for vehicles, storage, and hobbies. Don't miss the opportunity to tour this exceptional home and experience everything it has to offer.

285 Crystal Wood Drive, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Stone Creek 48 140 SubDv. ⋅ 34787 Zip Code

Welcome to this beautifully updated 3 bedroom, 2.5 bath home in the heart of Winter Garden, perfectly positioned for convenience, comfort, and everyday living. Enjoy being just 5 minutes from Winter Garden Village, 10 minutes from Downtown Winter Garden and Plant Street Market, and walking distance to top-rated Whispering Oak Elementary. Thoughtfully updated and move-in ready, this home offers a turnkey experience with major upgrades including a Brand New Water Heater (2026), New HVAC (2022 serviced bi-annually, most recent service in August 2026), New Roof (2019), New Vinyl Fence (2022), New Kitchen Appliances (2022), Upgraded Bathrooms (2022), and an Updated Kitchen (2022). Inside, the open concept floor plan is enhanced by high ceilings and a spacious living area that overlooks the remodeled kitchen. The kitchen features a large island, quartz countertops, subway tile backsplash, ample storage, and stainless steel appliances. The adjacent dining area seamlessly opens to a screened-in patio creating an inviting space for relaxing and enjoying indoor/outdoor living. The fully fenced backyard provides shade and plenty of room for outdoor activities. Upstairs, the spacious owner’s suite features a walk-in closet and a fully remodeled ensuite bath with double vanities, tiled floors, and a glass-enclosed shower. Two additional bedrooms share an updated bathroom featuring new tile, a new vanity, and a tub. Residents also enjoy neighborhood amenities including a newer playground with sunshades and turf, along with a nearby path leading to open green space with basketball courts, baseball and soccer fields—all en route to Whispering Oak Elementary. With thoughtful updates, desirable community amenities, and an exceptional Winter Garden location, this home is ready to welcome its next owner. Schedule your tour today!

1415 Sherbourne Street, Winter Garden

5 Beds ⋅ 5 Baths ⋅ Ests/Lakeview Preserve SubDv. ⋅ 34787 Zip Code

This is a rare opportunity to find a popular Roseland floorplan loaded with upgrades, perfectly located on a quiet cul-de-sac on a private lot with no rear neighbors and extra space on this oversized lot! Best of all, you can enjoy picturesque views of Johns Lake right from the front yard! Inside, you are greeted with a beautiful double glass door entry, soaring dramatic ceilings, and elevated light fixtures that create an immediate sense of openness and grandeur. Luxury vinyl plank floors throughout bring warmth to the home. To the right, you have an oversized flex room with French doors, making a perfect home office, play area, or home gym. The formal dining room provides a great space to gather around meals for family nights or holiday hosting. The butler's pantry features a wine fridge and added cabinets, while the walk-in pantry is truly impressive with built-in shelving. The kitchen is truly the heart of the home, featuring stunning quartz countertops, cream cabinets, upgraded lighting, and a beautiful tile backsplash. Transom windows in the backsplash pour natural light into the kitchen. The open breakfast area is perfect for enjoying quick meals with the family and overlooks the great room, which has custom accent walls and an elevated light fixture to enhance the space. Triple windows above brighten the room, & the 12ft slider door overlooks the extended lanai and huge flat yard—with plenty of space to add a pool and outdoor kitchen! Downstairs features a massive guest suite that can serve as a second master bedroom, complete with its own ensuite bath, upgraded shower, and large walk-in closet—perfect for in-laws or guests to have their own retreat! There is also another full-sized bath downstairs with a shower and a door leading out to the lanai for quick access from the future pool area. Heading upstairs, there are 4 additional bedrooms, 3 full baths, and the laundry room. Elegant open railings bring added character across the catwalk over the living room. Directly at the top of the stairs, French doors lead to your primary retreat. You are greeted by a sitting area with a large window and a massive primary suite with a tray ceiling and picturesque windows looking over the yard and trees beyond. To the left is your stunning ensuite bathroom with split vanities, lots of natural light, a soaking tub, a large walk-in shower with a bench, and dual closets (one with built-ins). The other three oversized bedrooms add similar quality, each with direct ensuite access to a bathroom (including two sharing a Jack-and-Jill bath). The laundry room features built-in cabinets and two washer/dryer sets side by side, allowing you to handle two loads at a time—perfect for large or busy families! Over in the garage, vehicle enthusiasts and storage seekers will marvel at the pristine three-car garage, complete with sleek epoxy flooring, heavy-duty overhead storage racks, and a private car wash station for ultimate convenience. The exclusive gated community offers resort-style amenities including a clubhouse, swimming pool, splash pad, and playground—all with a low HOA fee and no CDD. The community is perfectly located on the border of Clermont and Winter Garden, offering access to all both cities have to offer! You are just 15 minutes from Winter Garden Village for shopping, dining, and SR-429 access into Orlando, and within 20 minutes from both downtown Clermont and downtown Winter Garden. Come tour this stunning property today!

4817 Fair Winds Court, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 2d SubDv. ⋅ 34787 Zip Code

Virtually Staged. The appeal isn’t just the house—it’s the lifestyle that comes with the community. Welcome to 10625 Atwater Bay Drive, Winter Garden, FL 34787, where comfort, convenience, and resort-style living come together in the highly desirable Waterleigh community. The first floor features a private bedroom and full bathroom with a bathtub, ideal for guests, extended family, or convenient first-floor living. The kitchen offers a large center island, granite countertops, ample cabinetry, and a walk-in pantry, opening seamlessly to the living and dining areas. A rear lanai provides a relaxing outdoor space, while the alley-access garage helps maintain the home’s attractive streetscape. Upstairs, a spacious loft offers flexible space for a home office, media room, or playroom. The primary suite features an en-suite bath with dual sinks and a walk-in shower, while two additional bedrooms share another full bath. What truly sets this home apart is the Waterleigh lifestyle. Residents enjoy multiple resort-style pools, fitness centers, clubhouses, playgrounds, sports fields, tennis and pickleball courts, mini-golf, dog parks, walking trails, fishing areas, lakes, green spaces, and community activities. Conveniently located near SR 429, Waterleigh offers easy access to Disney, Orlando, shopping, dining, and entertainment—with Publix located right within the community. 10625 Atwater Bay Drive offers more than a home—it’s an opportunity to enjoy the resort-style lifestyle that makes Waterleigh such a desirable place to live.

10625 Atwater Bay Drive, Winter Garden

1 Beds ⋅ 1 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code

Resort style living in Winter Garden close to everything. Enjoy an impressive array of resort-style community amenities, including a state-of-the-art fitness center, indoor basketball and racquetball courts, tennis courts, and a beautifully appointed clubhouse featuring a private movie theater and dedicated workspace. Relax by the resort-style swimming pool and spa, or entertain outdoors with a fully equipped kitchen and grilling area. The community also offers a park and playground, providing something for everyone to enjoy. This 1bed/1 bathroom with a flex room boast commercial grade luxury vinyl plank flooring, crown molding throughout, granite counter tops throughout the kitchen and bathroom, dedicated dining room, indoor laundry room with washer and dryer included, neutral interior wall paint, excellent natural light, ensuite bathroom, ample size primary suite walk-in closet, and more. Conveniences to be noted in the association fees are: Water, Cable, Trash, Pest Control, Roof, Exterior Building Maintenance, and Pool. Live just minutes from Winter Garden Village, Historic Downtown Winter Garden, and the West Orange Trail. Getting around Central Florida is easy with quick access to SR-429, the Florida Turnpike, SR-408, and SR-50. Everyday shopping is also close by, with Publix and Costco Just minutes away. Low maintenance living at it's finest. Come see this condo today.

1315 Eastern Pecan Place Unit 202, Winter Garden

5 Beds ⋅ 4 Baths ⋅ Horizon Isle SubDv. ⋅ 34787 Zip Code

Welcome to luxury living in the heart of Horizon West! This stunning Santa Fe floorplan by K. Hovnanian Homes perfectly blends rustic charm with modern elegance, offering space, privacy, and an unbeatable location. Step inside to a bright, airy main living space featuring dramatic vaulted ceilings accented by rich wooden beams and seamless, carpet-free flooring—sleek tile flows throughout the main level, while high-end Luxury Vinyl Plank (LVP) spans the second floor. A designer farmhouse aesthetic carries through the gourmet kitchen and bathrooms, blending timeless style with everyday functionality. The main floor features a peaceful primary suite with a spa-like ensuite bath complete with a standalone soaker tub and separate shower, as well as a massive second guest bedroom with a stylish barn door entrance that works perfectly as a private suite or home office. Upstairs, a spacious loft offers a flexible secondary living area alongside three generously sized bedrooms and two full bathrooms. Outside, the covered lanai overlooks a peaceful, open grassy field, delivering ultimate backyard privacy with no rear neighbors. Positioned just down the street from the shopping, dining, and entertainment of Flamingo Crossings, minutes from Walt Disney World, and within walking distance to the brand-new Ovation Elementary School right outside the neighborhood, this home offers the ideal combination of high-end design, privacy, and everyday convenience. Schedule your private tour today!

13112 Dendy Way, Winter Garden

3 Beds ⋅ 4 Baths ⋅ Del Webb Oasis SubDv. ⋅ 34787 Zip Code

Step into the Renown, a new construction, single-story home situated on a corner homesite near a cul de sac offering 3 spacious bedrooms, 3 beautifully appointed full bathrooms, a powder room, and an open flex room. The open-concept layout seamlessly connects the gourmet kitchen, café, and gathering room, creating an airy atmosphere. The many windows and zero corner sliding glass door leading to the covered lanai bathe the entire space in natural light, elevating the overall feeling of openness. The heart of the home is the chef-inspired kitchen, where white cabinetry with wood uppers meets luxurious quartz countertops. Thoughtfully designed features like soft-close drawers, easy-reach corner cabinets, double roll-out trays, and a waste basket drawer make the kitchen as functional as it is beautiful. Whirlpool stainless steel appliances—including a built-in natural gas cooktop—ensure you have everything you need for both everyday meals and special occasions. The kitchen flows effortlessly into the café and gathering room, where a zero-corner sliding glass door leads to the covered lanai, making this home ideal for seamless indoor-outdoor living. Retreat to the luxurious owner’s suite, a serene sanctuary with two spacious walk-in closets and a spa-like en suite bathroom. Dual vanity sinks, a frameless glass enclosed shower, garden tub, an enclosed toilet, and a linen closet complete the tranquil space. For added convenience, one of the walk-in closets connects to the laundry room which is outfitted with built-in cabinetry, a utility sink trimmed in quartz, and a storage closet. The two additional spare bedrooms, each with their own attached bathroom and walk-in closets, along with the open flex room and powder room, provide ample space for family and guests. Designer-curated finishes elevate every corner of this home, including pendant pre-wire and under cabinet lighting in the kitchen, brushed nickel hardware and plumbing fixtures, and 8’ Cheyenne style interior doors. Enjoy the convenience of modern living with a smart thermostat and doorbell, and LED downlighting. Schedule a tour today!

15000 Canopy Cover Drive, Winter Garden

4 Beds ⋅ 4 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. Discover the perfect blend of luxury, comfort, and convenience in this stunning Mahogany Grand home. Thoughtfully designed for both everyday living and entertaining, this exceptional two-story residence offers 4 bedrooms, 3 full bathrooms, a convenient first-floor powder room, an enclosed flex room, and a spacious 3-car garage. The open-concept living area seamlessly connects the gourmet kitchen, café, and gathering room, creating an expansive and inviting space. Soaring ceilings and an elegant tray ceiling enhance the sense of openness, while a large pocket sliding glass door extends the living space onto the covered lanai, filling the home with natural light and creating the perfect blend of indoor and outdoor living. At the heart of the home, the gourmet kitchen showcases stacked soft-close cabinetry, quartz countertops, a decorative tile backsplash, farmhouse sink, and built-in Whirlpool stainless steel appliances, including a natural gas cooktop, range hood, and 48-inch side-by-side refrigerator. Whether preparing everyday meals or hosting special gatherings, this kitchen is designed to impress. Privately situated in the back corner of the home, the spacious owner's suite offers a peaceful retreat and features an owner's suite extension, providing additional space for a sitting area, fitness nook, workspace, or whatever best suits your lifestyle. The spa-inspired en suite bath includes a walk-in closet, linen closet, walk-in shower with a rain shower head, and a private enclosed water closet. The enclosed flex room at the front of the home adds valuable versatility and can easily function as a home office, fitness room, playroom, or creative studio. Two additional first-floor bedrooms located in the opposite back corner of the owner’s suite provide comfort and privacy for everyone. A conveniently located powder room further enhances the home's thoughtful design. Upstairs, enjoy an additional 884 square feet of flexible living space, complete with a generous loft, private fourth bedroom, and full bathroom, making it ideal for a media room, guest suite, home office, or multigenerational living. Completing the home is a spacious 3-car garage with ample room for vehicles, storage, and hobbies. Don't miss the opportunity to tour this exceptional home and experience everything it has to offer.

289 Crystal Wood Drive, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Lakeview Pointe/Horizon West P SubDv. ⋅ 34787 Zip Code

Virtually Staged. One or more photo(s) was virtually staged. Newly remodeled in 2026 and presented in like-new condition, this exceptional single-story lakefront home blends an elevated luxe coastal feel with relaxed Florida waterfront living. Set on a rare oversized lot along skiable Huckleberry Lake, the property offers exceptional privacy and space, with approximately 40 feet of separation between neighboring homes. The light and inviting interior features (4) four bedrooms, (3) three full baths, and a spacious open-concept floor plan. The beautifully updated kitchen showcases quartz countertops and flows seamlessly into the main living and entertaining areas. A generously sized open flex room offers additional versatility as a formal dining room, home office, formal living room, or sitting room and can easily be enclosed for additional privacy. Step outside to a large fenced backyard with a private pool and spa, all overlooking Huckleberry Lake. Enjoy direct lake frontage and water access, with the opportunity for a private dock, subject to applicable HOA approval and permitting. The (3) three-car garage includes a Tesla EV charger, and the expansive driveway accommodates up to (6) six additional vehicles. Lakeview Pointe offers a community dock on Huckleberry Lake, resort-style pool with splash area, and fully equipped fitness center. The HOA also takes care of the home's exterior lawn maintenance, giving you more time to enjoy the lake, pool, and Florida lifestyle. Ideally located in Winter Garden's Horizon West area, with easy access to SR 429 and minutes from shopping, dining, entertainment, and everyday conveniences. The property is currently zoned for A-rated Summerlake Elementary, Hamlin Middle School, and Horizon High School. Nearby early-learning options include Primrose School of Horizon West, The Learning Experience - Horizon West, and KLA Schools of Horizon West. Walt Disney World is approximately 20 minutes away. Buyers should independently verify current school assignments and grades. A rare opportunity to own a beautifully remodeled single-story pool home on skiable Huckleberry Lake, combining privacy, flexible living spaces, an oversized lakefront lot, and true Florida waterfront living.

14048 Larkspur Lake Drive, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Hamlin Meadows SubDv. ⋅ 34787 Zip Code

Virtually Staged. Under Construction. The Porter floor plan offers a smartly designed two-story townhome that caters to both convenience and space. With three bedrooms and two and a half bathrooms, this home ensures comfort on every level. All three bedrooms are located upstairs, providing privacy and quiet from the main living areas. The second floor also features a spacious primary suite with a walk-in closet and private bath, alongside two additional bedrooms. Downstairs, the open-concept layout connects the great room to the dining area, making it perfect for entertaining or gatherings. The covered lanai offers a cozy outdoor retreat, ideal for relaxing at the end of the day. Completing the home is a detached two-car garage, ensuring ample parking and storage. The Porter floor plan offers modern living tailored to meet everyday needs with style and functionality.

7276 Windy Willow Street, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Hamlin Meadows SubDv. ⋅ 34787 Zip Code

Virtually Staged. Under Construction. The Harbor floor plan offers a smartly designed two-story townhome that caters to both convenience and space. With three bedrooms and two and a half bathrooms, this home ensures comfort on every level. All three bedrooms are located upstairs, providing privacy and quiet from the main living areas. The second floor also features a spacious primary suite with a walk-in closet and private bath, alongside two additional bedrooms. Downstairs, the open-concept layout connects the great room to the dining area, making it perfect for entertaining or family gatherings. The covered lanai offers a cozy outdoor retreat, ideal for relaxing at the end of the day. Completing the home is a detached two-car garage, ensuring ample parking and storage. The Harbor floor plan offers modern living tailored to meet everyday needs with style and functionality.

7272 Windy Willow Street, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Serenade At Ovation SubDv. ⋅ 34787 Zip Code

Virtually Staged. DON'T wait for the builder for your Newbury model home! This Dream Finders Home is a 4-bedroom, 3-bathroom, and 2,083 square feet! This PREMIUM CORNER LOT next to conservation area and Lake View from primary suite. This home has a beautifully upgraded living space in a desirable area of Winter Garden. The neighborhood of Serenade at Ovation offers Elevation C which is the upgraded elevation with a more desirable curb appeal that includes stone veneer. The heart of the home features a modern kitchen with upgraded cabinets, backsplash tile and stylish light fixtures extending into the breakfast nook. This lot is near the conservation area and lake view from primary suite window. Throughout the house, you'll find upgraded light fixtures and enhanced lighting in the living room, creating a warm and inviting atmosphere. Tile throughout the 1st floor was a BUILDER UPGRADE! This primary bathroom boasts upgraded faucets, tile, and cabinets! The wood grain adorns the staircase instead of traditional carpet for an elegant touch. Every window is dressed in upgraded wood blinds as a BUILDER UPGRADE, and fresh upgraded paint brightens all interior rooms. Practical upgrades include an enhanced sink and cabinet in the laundry room; plus, extra light sockets strategically placed in the living room and additional prewiring in the upstairs bonus room for your convenience. Upgraded utility sink and cabinets in the laundry room on the 2nd floor. This thoughtfully upgraded home combines comfort, style, and functionality in a prime location. The attention to detail in every room, from the kitchen upgrades to the enhanced lighting throughout, creates a move-in ready property that's perfect for modern living. This neighborhood offers excellent connectivity, with nearby transportation options and convenient shopping. The proximity to quality educational facilities, including Horizon High School just minutes away, adds to the home's appeal. The area provides easy access to recreational opportunities, with Disney Theme parks and entertainment venues within a short drive. Brand New Publix, Miller's Alehouse in shopping plaza nearby. Enjoy Winter Garden's local history and charm! Bonus: includes high-speed fiber optic internet!.

13043 Serene Glade Road, Winter Garden

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