Winter Garden Homes with Florida Architectural style

Winter Garden Homes with Florida Architectural style

Welcome to Winter Garden, Florida, a vibrant city nestled in the heart of Orange County, where charm meets modern living! Known for its picturesque landscapes and friendly community, Winter Garden is a delightful blend of small-town warmth and urban convenience. With its rich history dating back to the late 1800s, the city has evolved into a thriving hub filled with lush parks, scenic lakes, and a bustling downtown area that showcases a variety of shops, restaurants, and cultural events.

One of the standout features of Winter Garden is its stunning array of homes that embody the timeless elegance of Florida architectural styles. From classic Mediterranean villas to contemporary coastal designs, the homes here reflect the beauty of the Sunshine State. Each property is thoughtfully crafted to embrace natural light and outdoor living, allowing residents to enjoy the year-round warm climate. Picture yourself sipping coffee on a spacious patio or hosting gatherings in your beautifully landscaped backyard—this is the lifestyle that Winter Garden offers.

Whether you’re a first-time homebuyer or looking for a luxurious retreat, Winter Garden’s real estate market has something for everyone. With its family-friendly atmosphere, top-rated schools, and access to recreational activities like hiking and biking along the West Orange Trail, it’s no wonder that families and retirees alike choose to call this enchanting city home.

Discover the charm of Winter Garden and explore the diverse housing options that await you in this idyllic Florida community. Your dream home is just around the corner!

Newest Winter Garden Homes with Florida Architectural style

13618 Larsen Lane, Winter Garden
$888,000
4 Beds ⋅ 4 Baths ⋅ Glynwood Ii SubDv. ⋅ 34787 Zip Code
Virtually Staged. A true pride-of-ownership home showcasing architectural elegance, extensive upgrades, and the ultimate Florida lifestyle! Welcome to this stunning Winter Garden residence featuring a freshly painted exterior, tropical landscaping, paver driveway, and spacious three-car garage. Inside, soaring 13.5-foot ceilings, architectural arches, double-tiered tray ceilings, and a custom coffered family room ceiling create an impressive atmosphere. The gourmet kitchen features a sprawling granite island with prep sink, 42-inch solid wood cabinetry custom-painted in November 2025, premium GE Profile stainless steel appliances, a cooktop, double ovens, and a separate butler’s pantry ideal for entertaining or a coffee station. Enjoy seamless indoor-outdoor living through 16-foot, four-panel sliding pocket doors opening to a spacious brick-paver, screened lanai. Relax beneath the covered patio with flush-mounted speakers or beside the oversized saltwater pool with a new variable-speed pump installed in October 2025. The private quarter-acre backyard features mature privacy hedging and a convenient pool-access bathroom with a glass-enclosed walk-in shower. The main-level primary suite offers an elegant tray ceiling, a custom walk-in closet system installed in February 2026, and luxury linen and blackout window treatments. More than $100,000 in reported premium upgrades enhance comfort, efficiency, and peace of mind. Improvements include a 2-ton Daikin 15.6 SEER2 HVAC system (September 2025), upgraded R-38 attic insulation (September 2025), zoned 5-ton variable-speed Trane HVAC. Whole house hot water hybrid system: Tankless water heater fed by propane tank as a main source (electric tank can be used as a back-up). Aquasure Harmony whole-house water softener (August 2024), and a roof replaced in August 2016. Smart-home features include pre-wired 7.1 family room surround sound, multi-zone audio, window-tint film, security cameras with hybrid DVR, motion-activated lighting, smart front-door and garage locks, smart thermostats, and a Rachio irrigation controller. The gated subdivision adds another layer of appeal. Located in desirable Glynwood II at StoneCrest, residents enjoy a clubhouse, resort-style pool, playground, tennis courts, and scenic walking trails with pond views, a fountain, and green spaces. Conveniently close to Winter Garden Village, shopping, dining, parks, and the West Orange Trail, the community also offers access to major roadways, Orlando’s employment and entertainment centers, world-famous theme parks, Orlando International Airport, and Florida’s beautiful beaches. Experience exceptional architecture, modern technology, privacy, and effortless entertaining in this remarkable Winter Garden home! Note: The last four photos have been virtually staged.

13618 Larsen Lane, Winter Garden

728 Garden West Terrace, Winter Garden
$1,749,000
5 Beds ⋅ 5 Baths ⋅ Garden West SubDv. ⋅ 34787 Zip Code
Welcome to this stunning custom home crafted by the renowned Pioneer Builders in 2022, nestled in one of Winter Garden's most coveted locations. Just steps from the beloved West Orange Trail and the charming Golf Cart District of Historic Downtown Winter Garden, this home offers the best of the Winter Garden lifestyle right at your doorstep. Whether you're pedaling the trail at sunrise or cruising downtown in your golf cart for dinner and live music, this location makes it easy to enjoy everything this vibrant community has to offer. From the moment you step inside, the quality and craftsmanship are undeniable. Engineered hardwood floors flow seamlessly throughout the home, while custom cabinetry adds timeless elegance to every space. The open living areas feature top-of-the-line Fisher & Paykel appliances, blending elevated design with everyday functionality. Plantation shutters throughout the main house add a classic, refined touch, while an automatic gate provides an added layer of privacy and convenience. The main level features a private ensuite bedroom and full bath, ideal for guests or multigenerational living, along with a convenient powder bath for visitors. Upstairs, the primary suite serves as a true retreat, complete with two oversized walk-in closets and a luxurious ensuite bath. Two additional bedrooms share a well-appointed Jack-and-Jill bathroom, while an upstairs laundry room adds everyday convenience. Added in 2024, the private apartment above the garage is a rare and exceptional bonus, complete with a kitchenette, dedicated office space, full bath, and in-unit laundry. Whether envisioned as a private guest suite, in-law quarters, a dedicated work-from-home retreat, or an income-producing rental, the possibilities are endless. Winter Garden's Golf Cart District is more than a novelty—it's a way of life. Residents enjoy cruising to the award-winning Farmers Market, exploring boutique shops and local restaurants, visiting breweries, and taking part in the community events that make Historic Downtown Winter Garden one of Central Florida's most vibrant destinations. The West Orange Trail, spanning more than 22 miles of scenic, paved pathways, is a paradise for cyclists, joggers, and walkers. With this home's prime proximity, outdoor recreation is always within easy reach. This is more than a home—it's a lifestyle. Don't miss the opportunity to own a distinctive property offering timeless finishes, versatile living spaces, added privacy, and an exceptional location in one of Central Florida's most sought-after communities.

728 Garden West Terrace, Winter Garden

1210 Brandy Lake View Circle, Winter Garden
$450,000
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

1300 Eastern Pecan Place Unit 208, Winter Garden
$298,500
3 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
BUYER INCENTIVE! Seller offering $5,000 toward buyer closing costs PLUS an additional $1,000 through the preferred lender—for up to $6,000 in buyer benefits with accepted contract, at closing Plus, enjoy a 2-year warranty on NEW kitchen appliances(refrigerator,microwave and dishwasher). Priced under $299,000! Discover this beautifully updated, move-in-ready condo in the GATED Southern Pines community, just 7 minutes from Historic Downtown Winter Garden! This second-floor residence offers convenient first-floor entry with private keyless access and a welcoming coat closet. Upstairs, the bright, open-concept feature newer luxury plank vinyl flooring, abundant natural light, updated lighting and ceiling fans, and a dedicated office alcove with custom built-in shelving. Fresh paint throughout—including walls, ceilings, doors, baseboards, and trim—creates a clean, contemporary feel. The upgraded galley kitchen features neutral cabinetry, granite countertops, a pantry, and BRAND-NEW, NEVER-USED stainless-steel refrigerator, microwave, and dishwasher! Its efficient layout keeps cooking connected to the living areas, while the conveniently located laundry room makes everyday tasks easier. The desirable split-bedroom floor plan continues with luxury plank vinyl flooring and offers privacy for the spacious primary suite, complete with a walk-in closet, ceiling fan and en-suite bath featuring a large walk-in shower and granite-topped vanity. Two additional bedrooms on the opposite side of the common area both with generous walk-in closets and ceiling fans. The second full bath features an extended granite vanity with abundant storage and a tub/shower combination. Both bathrooms showcase BRAND-NEW MOEN faucets and shower/tub fixtures, updated lighting, framed/finished mirrors, and new cabinet hardware. All interior door hardware has also been replaced with lever handles and hinges in updated finish to match all the new fixtures and hardware throughout. Extra storage is a plus in the laundry-room (Washer and dryer are negotiable) and linen closet near the HVAC system, which has received seasonal servicing. Drapes do not convey. Resort-style amenities abound! Southern Pines residents enjoy a pool and spa, fitness center, tennis courts, indoor basketball court, volleyball court, playground, pet park, clubhouse with theater room, billiards room, computer center, BBQ area, and resident car wash station. Gated entry and on-site management add convenience. Enjoy easy access to Publix, Winter Garden Village, the West Orange Trail, Historic Downtown Winter Garden, shopping, dining, entertainment and medical facilities. The Florida Turnpike, SR 429, and I-4 provide convenient connections throughout Central Florida, including Orlando attractions and major employment centers. HOA dues include internet, basic cable, trash service, recreational amenities, and exterior lawn care and exterior maintenance. Enjoy the convenience of condo living, with exterior maintenance and roof replacement handled through the association in accordance with its governing documents and budget. EXTENSIVELY UPDATED. MOVE-IN READY. EXCEPTIONAL VALUE! Brand-new kitchen appliances, a 2-year appliance warranty, resort-style amenities managed professionally and up to $6,000 in buyer benefits make this a fantastic Winter Garden opportunity. Schedule your private showing today!

1300 Eastern Pecan Place Unit 208, Winter Garden

10048 Beach Port Drive, Winter Garden
$1,199,000
5 Beds ⋅ 4 Baths ⋅ Waterleigh Ph 2b SubDv. ⋅ 34787 Zip Code
PREMIUM LAKE LOT WITH POOL! Enjoy serene LAKE VIEWS and captivating SUNSETS! Most POPULAR Floor Plan – North Haven – has 5 Bedrooms, 3.5 Baths, Gourmet Kitchen, First Floor Primary Suite, TONS OF STORAGE, Tile Roof and 3 Car Garage just minutes from DISNEY! The OUTDOOR LIVING Space is a Showstopper! Generous COVERED Patio – perfect space for Dining and Relaxing! DELUXE SCREENED POOL with Sun Shelf, SALT SYSTEM, LED Lights and DECK JETS! This METICULOUSLY Maintained Home has a GOURMET KITCHEN with 42” Cabinets, Large Island, Upgraded Tile Backsplash, NEW PENDANT LIGHTS, Large FARM SINK, Under Cabinet Lighting, SS APPLIANCES including Built-In CONVECTION OVEN and COOK TOP with CABINETRY VENT HOOD! Large Pantry with CUSTOM SHELVING!! OPEN FLOOR PLAN with Views of the Patio, Pool and LAKE from Family Room and Casual Dining! First Floor Primary Suite with French Door to Patio and CUSTOM CLOSET! Bath Features DOUBLE Vanities and OVERSIZED Walk-In DOUBLE SHOWER. FLEX Space can be Dining Room, Office or Living Room. Convenient Remodeled Powder Bath with NEW Vanity, Counter and Mirror and Laundry Room with Cabinetry, Included WASHER and DRYER and Utility Sink complete the First Floor. Main Living Space has Upgraded Rectangular Tile, 8’ Doors and 5 ¼ Molding. Two Story Foyer features Stairs with Wood Railings and Wrought Iron Spindles. The HUGE LOFT separates the Upstairs. ALL 4 Bedrooms have WALK-IN Closets! Bedrooms 2 and 3 share Full Bath 2 with Upgraded SHOWER instead of a tub and Bedrooms 4 and 5 share a Jack-and-Jill Bathroom. Numerous Upgrades: GUTTERS, EV NEWER Dishwasher, NEW LED Pool Lights, NEW Solonoid for Pool Salt System, Dedicated GENERATOR Hook Up, Garage with EV Charger, EPOXY FLOOR and Overhead STORAGE RACKS ! ENERGY EFFICIENT Home with LoE Double Pane Windows, 15 Seer AC & Reclaimed Water for Irrigation Saves $$ on Utilities. Waterleigh is the PREMIER LIFESTYLE COMMUNITY with 4 Resort Style Pools, 3 Clubhouses with Fitness Centers, Walking Trails, Sand Volleyball, Dog Park, Fishing and Observation Pier, Tennis, Pickleball, Playgrounds and more! HOA Does all Yard Maintenance. All this zoned for NEW Atwater Bay Elementary, Water Spring Middle School and Horizon High School! Close to Disney, Shopping, Dining, 429, I-4, 417 and a NEW PUBLIX

10048 Beach Port Drive, Winter Garden

14501 Grove Resort Unit 2304, Winter Garden
$165,000
2 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condo 2 SubDv. ⋅ 34787 Zip Code
Short Sale. Experience the Ultimate Orlando Resort Lifestyle & Investment Opportunity! Welcome to The Grove Resort & Water Park, one of Central Florida’s premier vacation destinations, ideally located just minutes from Walt Disney World and close to Universal Studios, SeaWorld, Margaritaville Resort, shopping, dining, and Orlando International Airport. Enjoy a fully furnished, turnkey 2-bedroom, 2-bath condominium that offers the perfect blend of comfort, style, and investment flexibility. The spacious open-concept floor plan features a beautifully appointed kitchen, bright great room, oversized windows, and a private balcony overlooking the peaceful courtyard. The split-bedroom layout provides privacy, while two spa-inspired bathrooms feature garden tubs, tiled showers, and dual vanities. With a sleeper sofa in the living room, the residence comfortably accommodates up to six guests. Step outside your front door and discover an extraordinary resort experience. The spectacular Surfari Water Park features a FlowRider® surf simulator, dueling water slides, lazy river, splash park, activity pool, zero-entry pool, and private cabanas with food and beverage service. Additional amenities include multiple pools and hot tubs, a 20-acre activity lake with private dock, fishing, fitness center, full-service spa, arcade, game room, and an array of on-site dining options including Longboard Bar & Grill, Valencia Restaurant, Element Bar & Lounge, Alfresco Market, and Byte. Convenient shuttle transportation to Disney World, Universal Studios, and SeaWorld adds even more appeal for vacation guests. As a short-term rental property, owners may enjoy personal use, while professional on-site management can handle bookings, housekeeping, maintenance, and guest services. Whether you're looking for a personal Orlando getaway, a vacation home, or a hands-off investment opportunity, this property offers an exceptional combination of resort amenities, flexibility, convenience, and income potential. Experience the magic of Orlando while owning your own piece of the vacation lifestyle at The Grove Resort & Water Park!

14501 Grove Resort Unit 2304, Winter Garden

4780 Terrace Bluff Street, Winter Garden
$559,900
4 Beds ⋅ 4 Baths ⋅ Enclave/Hamlin SubDv. ⋅ 34787 Zip Code
Welcome to 4780 Terrace Bluff, a 4-bedroom home in **Enclave at Hamlin** offering an appealing combination of space, flexibility and value in the heart of Horizon West. The seller is also offering **$5,000 toward buyer closing costs**, giving buyers added flexibility as they plan their move. The open-concept floor plan creates an easy flow between the kitchen, dining and living spaces, making the home equally comfortable for everyday living and entertaining. A full bedroom and bath on the first floor adds valuable flexibility for guests, multigenerational living or a private home office. Upstairs, the oversized primary suite offers a spacious retreat with a generous bath, while the additional bedrooms are comfortably sized with plenty of room to grow, work or play. One of the standout benefits of this home is how much convenience is built into everyday living. The HOA includes **lawn care and access to the community pool**, adding real value while giving you more time to enjoy the neighborhood and everything nearby. Restaurants, coffee shops, shopping, entertainment and everyday conveniences are just minutes away, with the new library and Horizon West Regional Park right around the corner. Disney is nearby, and quick access to the 429 makes getting around Central Florida easy. The home is also zoned for Independence Elementary, Bridgewater Middle School and Horizon High School. With a flexible layout, generous living spaces, community amenities, lawn care included and a location that puts so much of Horizon West within easy reach, **4780 Terrace Bluff offers a compelling combination of comfort, convenience and value**. Add the seller’s $5,000 closing-cost contribution, and it becomes an even stronger opportunity for buyers looking to make a move before the holidays.

4780 Terrace Bluff Street, Winter Garden

15515 Campden Street, Winter Garden
$359,900
3 Beds ⋅ 3 Baths ⋅ Stoneybrook West I SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to this Gorgeous Home, where CONVENIENCE, and LOW-MAINTENANCE LIVING come together in a fantastic Winter Garden location making it easy to enjoy the vibrant Winter Garden lifestyle!! Step inside this to FRESHLY PAINTED 3 bedroom, 2.5 bath home. Featuring highly desirable WOOD-LOOK CERAMIC TILE throughout the main living areas, including the spacious living room, dining area, and kitchen.The kitchen features a NEW REFRIGERATOR, while a convenient downstairs half bath and large storage closet add to the home’s functionality. Upstairs, the VERSATILE LOFT adds valuable additional living space and is perfect for a home office, media room, playroom, fitness area, or cozy second family room. Plus the convenience of an UPSTAIRS LAUNDRY ROOM. The SPACIOUS Primary suite has 2 WALK-INCLOSETS and an ensuite bathroom with DUAL SINKS. The secondary bedrooms are also spacious and the 2nd bedroom also has a WALK-IN CLOSET as well. Enjoy added peace of mind with a NEW A/C installed in 2022, ROOF approximately 3 years NEW, gutters, and fresh exterior paint completed in 2025. Enjoy Florida living with access to the COMMUNITY POOL, perfect for cooling off, relaxing, and enjoying sunny Central Florida days without the maintenance of a private pool. The HOA provides exceptional value and low-maintenance living, including pest control, lawn, exterior maintenance, roof replacement approximately every 10 years, exterior painting, community pool, and tot lot. And then there's the LOCATION! Enjoy convenient access to the charm and energy of HISTORIC DOWNTOWN Winter Garden, where brick-lined streets are filled with locally loved restaurants, cafés, boutique shops, entertainment, and the popular Farmers Market. Grab a coffee, meet friends for dinner, spend an afternoon browsing the shops, or simply enjoy the welcoming small-town atmosphere. Outdoor enthusiasts will love the 22-mile West Orange Trail, which travels directly through the heart of Downtown Winter Garden. Whether you enjoy biking, running, walking, or simply getting outside, the trail offers miles of recreation and is one of the area's signature lifestyle amenities. This is more than just a home, it’s a lifestyle!

15515 Campden Street, Winter Garden

15562 Waterleigh Cove Drive, Winter Garden
$799,900
4 Beds ⋅ 4 Baths ⋅ Waterleigh Phase 1a SubDv. ⋅ 34787 Zip Code
LAKEFRONT GEM! Enjoy LAKE VIEWS and over 3 Acres of wide open GREEN SPACE behind this nearly 3,000 sq ft Upgraded SELDEN Floor Plan with 4 Bedrooms PLUS LOFT and FLEX SPACE, 3.5 Baths and a 3 CAR GARAGE with an OVERSIZED SCREEN ENCLOSURE with NO REAR NEIGHBORS just minutes from DISNEY! This special property is a PRIVATE OASIS with a Tranquil Screened LANAI with Party Lights and Water Fountain, Composite Deck with GRILL AREA, and delightful Bench Swing to enjoy the peaceful Garden with Lush Landscaping and Picturesque LAKE VIEWS! Best Features Include an OPEN FLOOR PLAN with GOURMET Kitchen, Upgraded Glazed Cabinets, GRANITE Counters, Pendant Lights, LARGE ISLAND, Cabinet Underlighting, Tile Backsplash, SS APPLIANCES including NEWER Stove, Microwave & Dishwasher and SUPER SIZED Pantry! PLUS, a custom BUTLER PANTRY with Cabinetry, WINE Fridge and BEVERAGE Fridge! Spacious Family Room has Triple Windows and Dining Area with DOUBLE SLIDERS opens to the OUTSTANDING OUTDOOR LIVING SPACE! First Floor Bedroom 4 is Located NEXT to FULL Bath 3 and nearby FLEX SPACE can be Office or Formal Dining. Upstairs, the Primary Suite features LAKE Views, Tray Ceiling and a Luxurious Bath with DOUBLE Sinks, Glazed Cabinets, LARGE SHOWER with Upgraded Wall Tile and a Generous Walk-In Closet. LOFT is a great space for Office, Study or PLAY ROOM! Home Features: 8’ Doors on 1st Floor, Convenient POWDER BATH near Patio, Upgraded Light Fixtures & Fans, Wrought Iron Railings, VIDEO Doorbell, Tandem 3 Car Garage with 7 Storage Racks, NEW AC upstairs in 2023, SOLAR Tinted Windows, Gutters, Exterior Painted (2023) & more! Beds 2 & 3 share Bath 2 & a Large Laundry Room with INCLUDED WASHER & DRYER & Storage Cabinets is pre-plumbed for a Laundry Tub. This Home is ENERGY EFFICIENT with Double Pane “Lo E” Windows, R-30 Insulation and Reclaimed Water for Irrigation. Located in WATERLEIGH – the PREMIER LIFESTYLE COMMUNITY in the area with 4 Community Pools, 3 Clubhouses and 3 Fitness Centers, Fishing Pier, Playgrounds, Parks, Sand Volleyball, Tennis and MUCH MORE! RELAX and enjoy your home – HOA does all Yard Work! All this close to DISNEY, DINING, SHOPPING plus Panther Lake Elementary, Water Spring Middle and NEW Horizon High School! Easy Access to 429, 417 and 408!

15562 Waterleigh Cove Drive, Winter Garden

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