Winter Garden Homes with Traditional Architectural style

Winter Garden Homes with Traditional Architectural style

Welcome to Winter Garden, Florida – a charming city that beautifully blends historic charm with modern conveniences. Nestled just 14 miles west of Orlando, Winter Garden is renowned for its picturesque downtown area, vibrant community events, and rich agricultural history. The city’s scenic landscapes and lush gardens create a serene backdrop for residents and visitors alike, making it a perfect place to call home.

One of the most appealing aspects of Winter Garden is its commitment to preserving its heritage, evident in the stunning traditional architectural styles that grace its neighborhoods. Homes here often feature classic designs that evoke a sense of warmth and nostalgia, with inviting front porches, gabled roofs, and intricate brickwork. These traditional homes not only reflect the city's history but also provide a cozy and welcoming atmosphere for families and individuals.

Living in Winter Garden means enjoying a tight-knit community with an array of amenities at your fingertips. From the bustling farmers' market to the scenic West Orange Trail, outdoor enthusiasts will find plenty of opportunities to explore the natural beauty of the area. Additionally, the city boasts top-rated schools, beautiful parks, and a variety of dining and shopping options, ensuring that residents have everything they need within reach.

Whether you're drawn to the charm of traditional architecture or the vibrant lifestyle that Winter Garden offers, this city is a hidden gem waiting to be discovered. Come experience the warmth and beauty of Winter Garden, where your dream home awaits amidst a community that feels just like family.

Newest Winter Garden Homes with Traditional Architectural style

9991 Schroeder Alley, Winter Garden
$378,000
3 Beds ⋅ 3 Baths ⋅ Waterleigh Phase 2d SubDv. ⋅ 34787 Zip Code
Welcome home to 9991 Schroeder Alley, tucked away in Winter Garden’s highly coveted, resort-style community of Waterleigh! From the moment you step inside, you will feel the perfect blend of modern comfort and effortless Florida living. This stunning townhome has been meticulously maintained and offers ultimate peace of mind with major structural upgrades already taken care of—featuring a brand-new HVAC system (2026) and a solid roof and water heater (both 2019). You won't have to spend a dime on the big-ticket items; you can simply move in, unpack, and start living your best life. New dishwasher (2026) and that the washer and dryer convey. What truly sets this home apart is the incredible lifestyle that comes with it. Living in Waterleigh feels like being on a permanent vacation. You are just steps away from world-class amenities, including multiple resort-style pools, dynamic fitness centers, a beautiful community clubhouse, beach volleyball, tennis and pickleball courts, dog parks, and scenic walking trails around clean, peaceful lakes. Located in the heartbeat of Horizon West, you are only minutes away from the charming shops and dining at the Horizon West Regional Center, Winter Garden schools, and local favorites like the Winter Garden Village. Best of all? You are so close to Disney World that you can end your evenings watching the nightly fireworks light up the sky right from your neighborhood. Whether you’re looking for a low-maintenance sanctuary or a vibrant, active community to call home, this Horizon West gem is the one you’ve been waiting for. Schedule your tour today and fall in love with the Waterleigh lifestyle!

9991 Schroeder Alley, Winter Garden
10732 Petrillo Way, Winter Garden
$899,990
5 Beds ⋅ 6 Baths ⋅ Winding Bay Ph 1b SubDv. ⋅ 34787 Zip Code
**Experience the Best of Florida Living in Horizon West!** Welcome to the (en)suite life, where luxury, space, and exceptional living come together in this beautifully appointed pool home. Nestled in a highly sought-after Horizon West community with low HOA fees, this impressive two-story residence offers the highly desirable Grayson floor plan, a rare three-car tandem garage, and an abundance of thoughtfully designed living space. Inside, elegant crown molding adds a touch of sophistication, while the gourmet kitchen, featuring beautiful stone countertops and an oversized island, serves as the perfect gathering place for family and friends. The thoughtfully designed first floor features a private owner's retreat overlooking the sparkling pool and tranquil pond, complete with an upgraded tray ceiling and a spa-inspired bathroom with an oversized shower. An additional ensuite bedroom on the main level provides the perfect accommodations for guests or multigenerational living, while a dedicated private office offers an ideal work-from-home environment. Upstairs, discover three additional generously sized bedrooms, including two more ensuite bedrooms, all with spacious walk-in closets. A versatile loft provides additional space for recreation or relaxation, while the private theater/media room creates the ultimate setting for movie nights and entertainment. Step outside to your screened-in pool and lanai, where peaceful pond views and breathtaking Florida sunsets create the perfect backdrop for morning coffee, evening relaxation, or entertaining guests. With five bedrooms, four ensuite bedrooms, multiple living and entertainment spaces, and a location in one of Horizon West's desirable communities, this exceptional home offers the space, flexibility, and lifestyle today's buyers are looking for. Thanks to the recent amendment passing, this is your chance to own this beautiful home with lower property taxes.**Don't miss the opportunity to make this extraordinary home yours! Schedule your private showing today!**

10732 Petrillo Way, Winter Garden
243 Zachary Wade Street, Winter Garden
$1,150,000
5 Beds ⋅ 4 Baths ⋅ Lakeview Reserve 46/149 SubDv. ⋅ 34787 Zip Code
RARE WATERFRONT OPPORTUNITY IN WINTER GARDEN | DIRECT LAKE APOPKA ACCESS | PRIVATE BOAT DOCK Welcome to Lakeview Reserve, one of Winter Garden's desirable gated communities, where waterfront living meets the charm and convenience of Historic Downtown Winter Garden. This impressive 5-bedroom, 3.5-bathroom home offers approximately 3,097 square feet of living space and a feature that is becoming increasingly hard to find: direct access to Lake Apopka with your own covered boat dock and boat lift. Inside, the home offers spacious living areas, a beautifully appointed gourmet kitchen with upgraded cabinetry, soft-close drawers, dual sinks, a large island with prep sink, and a pot filler. The home has been freshly painted throughout, and the bathrooms have been renovated, giving the interior a fresh, updated feel. Two ensuite bedrooms upstairs provide additional comfort and flexibility for family and guests. The outdoor space is just as special. Step into your backyard and enjoy the waterfront setting, complete with a covered private dock and boat lift, making it easy to enjoy boating, fishing, and everything Lake Apopka has to offer. The backyard also features an assortment of fruit-bearing trees, including mango, avocado, star fruit, and citrus, adding a special touch to this Florida retreat. Additional features include roof replaced in 2019, recently serviced HVAC system, an oversized three-car garage, tankless water heater, and whole-house water softener and purification system. Location is another highlight, with golf cart access to Historic Downtown Winter Garden, where you can enjoy local restaurants, boutique shopping, the popular farmers market, and year-round community events. A rare opportunity to enjoy the space, privacy, and convenience of a gated community with the added luxury of direct Lake Apopka access. Come experience what makes this Winter Garden property so special!

243 Zachary Wade Street, Winter Garden
15928 Citrus Knoll Drive, Winter Garden
$1,549,000
6 Beds ⋅ 6 Baths ⋅ Hickory Hammock Ph 1d SubDv. ⋅ 34787 Zip Code
Virtually Staged. LUXURY LAKEFRONT LIVING AT ITS FINEST! Welcome to 15928 Citrus Knoll Drive, Winter Garden, FL 34787, an exceptional lakefront residence offering an impressive combination of elegance, space, and an extraordinary natural setting. Situated along the shores of Lake Burnett, a private conservation lake surrounded by majestic old oak trees draped in beautiful Spanish moss, this remarkable property offers a peaceful and picturesque backdrop for luxury living. Featuring 6 spacious bedrooms, and 5 1/2 bathrooms, this expansive home is thoughtfully designed for entertaining and comfortable everyday living. The interior showcases ceramic tile flooring throughout the entire first floor, elegant crown molding, and freshly painted walls in a neutral palette. The chef-inspired kitchen is sure to impress, featuring GE stainless steel appliances, a double oven, vent hood, and expansive counter space and storage, ideal for preparing meals and entertaining. Formal living and dining spaces provide an elegant setting for special occasions, while an additional butler's bar offers even more room to entertain. The luxurious primary suite offers a private retreat, complete with a screened-in balcony overlooking the majestic oak trees and serene waters of Lake Burnett. Enjoy your morning coffee or unwind in the evening while taking in the beautiful natural surroundings. The spacious primary bath features dual vanities, a large walk-in shower, and a relaxing soaking tub. The thoughtfully designed bedroom layout offers exceptional flexibility, including a convenient first-floor guest bedroom with en-suite bathroom access, ideal for visitors or multigenerational living. Two additional bedrooms feature private en-suite bathrooms and walk-in closets, providing comfort and privacy for family members and guests alike. The expansive bonus room, complete with its own bar area, creates the ultimate entertainment destination and offers endless possibilities as a game or media room. Beyond the home, enjoy an exceptional gated community lifestyle which Hickory Hammock offers, with amenities including a community fishing dock, tennis courts, clubhouse, and fitness center. The crown jewel of this property is undoubtedly its setting on Lake Burnett, where mature oak trees, graceful Spanish moss, and the peaceful conservation lake create a truly special Florida lifestyle. A rare opportunity to experience elegant lakefront living, generous entertaining spaces, and exceptional community amenities in desirable Winter Garden. This is more than a home—it's a lifestyle! (Roof 2015, A/C 2015/2025, Water Heaters 2023).

15928 Citrus Knoll Drive, Winter Garden
17906 Hither Hills Circle, Winter Garden
$560,000
4 Beds ⋅ 4 Baths ⋅ Lake Apopka Sound SubDv. ⋅ 34787 Zip Code
3.99 ASSUMABLE MORTGAGE OPPORTUNITY! Built in 2022, this four-bedroom home in Lake Apopka Sound offers single-story living, a three-car garage, and an open layout perfect for entertaining. The spacious kitchen features an oversized island, granite countertops, stainless steel appliances, and ample storage overlooking the inviting great room. A split-bedroom design provides privacy, while the primary suite includes dual vanities, a soaking tub, separate shower, and walk-in closet. Enjoy nearby outdoor adventures at the West Orange Trail and Oakland Nature Preserve, plus dining, boutiques, Plant Street Market, and the Saturday farmers market in historic Downtown Winter Garden. Shopping at Winter Garden Village and access to Florida’s Turnpike, SR 429, and Highway 50 add everyday convenience. Schedule your private showing today! Mortgage assumption subject to lender approval, buyer qualification, and applicable loan terms.

17906 Hither Hills Circle, Winter Garden
2010 Boss Hewett Street, Oakland
$1,450,000
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
5705 New Independence Parkway, Winter Garden
$399,900
3 Beds ⋅ 3 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
11390 Bourbon Rose Circle, Winter Garden
$860,494
4 Beds ⋅ 3 Baths ⋅ Esplanade At Mckinnon Groves SubDv. ⋅ 34787 Zip Code
What's Special: No Rear Neighbors | Larger Lot | Convenient 1st Floor Living. New Construction - Ready Now! Welcome to the Bainbridge at 11390 Bourbon Rose Circle in Esplanade at McKinnon Groves! This spacious single-story home offers four bedrooms, three bathrooms, a versatile flex room, and a three-car garage. The open-concept layout features a bright great room that flows into the dining area and gourmet kitchen with walk-in pantry, creating the perfect space for gathering and entertaining. The private primary suite is tucked away at the rear of the home, while three secondary bedrooms provide comfort and flexibility. Enjoy outdoor living on the covered lanai. Additional Highlights Include: tray ceiling package, whole house 8' interior doors, outdoor kitchen rough-in, and prewired for future pool and spa. MLS#O6451559 Esplanade at McKinnon Groves offers resort-style living in a gated Winter Garden community surrounded by natural beauty. Planned amenities include a fitness center, movement studio, resort pool and spa, Bahama Bar, pickleball, tennis, and bocce courts. Residents will also enjoy yoga lawns, a Bark Park, rose garden, scenic trails, concierge services, and year-round events. Zoned for Lake County schools, it blends everyday convenience with an active lifestyle.

11390 Bourbon Rose Circle, Winter Garden
14204 Creekbed Circle, Winter Garden
$812,000
4 Beds ⋅ 4 Baths ⋅ Bradford Creek SubDv. ⋅ 34787 Zip Code
Virtually Staged. SUPER PREMIUM LOT • CONSERVATION VIEW • NO REAR NEIGHBORS • HUGE FULLY-FENCED YARD • 3-CAR GARAGE • GATED COMMUNITY! Welcome to 14204 Creekbed Circle, a beautiful 4-bedroom, 3.5-bathroom home located in the desirable Bradford Creek community of Winter Garden. Set on an exceptional premium lot, this home offers a peaceful conservation view with no rear neighbors and an expansive, fully fenced backyard, providing wonderful privacy and plenty of outdoor space. Inside, you'll find solid hardwood flooring and tile, creating an elegant and timeless feel throughout the home. The highly sought-after 3-car garage provides generous space for vehicles, storage, or hobbies. For added value and peace of mind, both A/C units were replaced in January 2025. Enjoy the privacy and exclusivity of a gated community while being located in one of Winter Garden's most desirable areas. This property is a standout opportunity. Schedule your private showing and experience everything this exceptional Winter Garden home has to offer!

14204 Creekbed Circle, Winter Garden
16742 Oakboro Street, Winter Garden
$519,000
4 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 3b 3c & 3d SubDv. ⋅ 34787 Zip Code
Welcome to this better-than-new 4-bedroom, 2.5-bathroom home in the highly desirable Waterleigh community of Horizon West! Built in 2020, this thoughtfully upgraded home offers 2,014 square feet of living space, an inviting open-concept layout ideal for entertaining, and the convenience of a first-floor primary suite featuring a custom closet. The kitchen boasts granite countertops, stainless steel appliances, a touch-activated pull-down faucet, and a spacious butler’s pantry offering abundant storage. Additional owner upgrades include matte black hardware and ceiling fans throughout, smart light switches and fans, and a Fisher & Paykel washer and dryer. Enjoy Florida living year-round on the screened-in lanai, with added peace of mind from the upgraded fenced yard featuring two gates and puppy pickets, a complete gutter system, and electrical wiring ready for a whole-house generator. The garage is equipped with overhead storage and is EV-ready with an installed Tesla charger. Waterleigh residents enjoy an exceptional array of amenities, including two resort-style clubhouses and pools, two fitness centers, putt-putt golf, beach volleyball, tennis, a lake-view picnic area, a dog park, and more. With its desirable location, modern conveniences, and extensive upgrades, this home offers a wonderful opportunity to enjoy the best of the Waterleigh lifestyle!

16742 Oakboro Street, Winter Garden
17600 Lake Star Road, Winter Garden
$1,350,000
5 Beds ⋅ 4 Baths ⋅ Northlake/Ovation Ph 1 SubDv. ⋅ 34787 Zip Code
Discover exceptional lakefront living in Northlake at Ovation, where this extensively upgraded Ashton Woods residence showcases more than $320,000 in builder design selections and owner-added enhancements. Thoughtfully curated interiors, distinctive architectural details, and inviting outdoor spaces create a home equally suited to elegant entertaining and everyday comfort. A soaring foyer, statement chandelier, and beautifully detailed staircase establish an impressive arrival. Natural light fills the living spaces, highlighting plantation shutters, upgraded tile and hardwood flooring, custom wall treatments, and designer lighting throughout. The separate dining room provides an elegant setting for gatherings, while the kitchen, breakfast area, and family room flow seamlessly together. At the heart of the home, the beautifully appointed kitchen pairs an expansive contrasting island with designer quartz countertops, stacked cabinetry, and illuminated display accents. A custom backsplash and mural extending to the ceiling create a striking focal point, complemented by stainless steel appliances, pendant lighting, and a custom-organized pantry. The primary suite creates a peaceful retreat with hardwood flooring, generous windows, and a custom walk-in closet. Its spa-inspired bathroom features a soaking tub, separate vanities, upgraded fixtures, and an expansive frameless glass shower framed by striking tilework. Additional bedrooms and bathrooms carry the home’s thoughtful design throughout, including custom closet systems in the downstairs bedroom and designer accent walls in the downstairs bathroom. A dedicated office and spacious upstairs loft provide versatile settings for work, leisure, and recreation. Outdoor living unfolds beneath a covered paver lanai with roll-up screens and a custom summer kitchen featuring a built-in grill, beverage chiller, sink, upgraded countertops, and integrated storage. Generous dining and lounging areas overlook the fenced backyard, mature greenery, and tranquil lakefront setting—an inviting backdrop for morning coffee or evening gatherings. Beyond its beautiful finishes, the home incorporates carefully considered functionality: a custom laundry room with cabinetry and a sink, a drop zone, custom storage, whole-house gutters, backyard French drains, and pre-plumbing for a water softener. A hardwired security system and cameras, along with hardwired internet and Ethernet connections at TVs, provide added convenience. The garage includes epoxy flooring, overhead smart storage racks, cabinetry, and a utility sink. Redesigned landscaping and architectural uplighting enhance the home’s presence after sunset. Northlake at Ovation amenities include a community pool, clubhouse, playground, and dog park. Nearby Hamlin Town Center and Winter Garden Village provide shopping, dining, and entertainment, while Historic Downtown Winter Garden invites exploration of its boutiques, restaurants, celebrated farmers market, and West Orange Trail. Walt Disney World and Central Florida’s renowned attractions are within reach, with SR 429 connecting you to the greater Orlando area. Experience beautifully appointed interiors, extensive upgrades, and inviting lakefront living in this exceptional Winter Garden residence. Schedule your private showing.

17600 Lake Star Road, Winter Garden
1210 Brandy Lake View Circle, Winter Garden
$425,000
3 Beds ⋅ 2 Baths ⋅ Brandy Creek SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to this charming 3-bedroom, 2-bath home nestled in the desirable gated community of Brandy Creek in Winter Garden! Step inside to discover an inviting, open layout where the living area flows seamlessly into the kitchen and dining space, creating a comfortable setting for everyday living and entertaining. The kitchen features granite countertops and ample cabinetry for storage. French doors open to an extended screened-in lanai, providing the perfect space to relax, entertain, or simply enjoy the Florida lifestyle. The fenced backyard offers additional room for outdoor activities, pets, or gatherings with family and friends. The primary suite features a walk-in closet and an en-suite bathroom with dual sinks, a garden tub, and a separate shower. The additional bedrooms provide comfortable, flexible spaces for family, guests, or a home office. With generous living spaces and the opportunity to add your own personal touches, this home offers wonderful potential to make it truly your own. Beyond the home, Brandy Creek offers a peaceful setting with tranquil ponds, a scenic lake, and a community fishing pier. Just minutes from Historic Downtown Winter Garden, you'll enjoy easy access to the popular West Orange Trail, Saturday Farmers Market, live music, boutique shopping, and an incredible variety of local restaurants. Convenient access to the Florida Turnpike and SR-429 makes commuting and exploring Central Florida a breeze. Whether you're enjoying a quiet evening on your screened lanai or exploring the charm of downtown Winter Garden, this home offers a wonderful combination of space, location, and lifestyle. Don't miss the opportunity to make it your own!

1210 Brandy Lake View Circle, Winter Garden
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