Winter Garden Homes with Rain Gutters Exterior Features

Winter Garden Homes with Rain Gutters Exterior Features

Welcome to Winter Garden, Florida—a charming city that perfectly blends small-town warmth with modern conveniences. Nestled just a short drive from the bustling attractions of Orlando, Winter Garden boasts a rich history, vibrant community, and an array of outdoor activities that make it an ideal place to call home. With its picturesque downtown area, lined with quaint shops and delightful eateries, residents enjoy a lively atmosphere infused with Southern hospitality. The city's stunning parks and scenic trails invite you to explore the natural beauty of Florida, whether you're biking along the West Orange Trail or enjoying a leisurely stroll by Lake Apopka.

One of the many appealing aspects of homes in Winter Garden is their thoughtful design, particularly the inclusion of rain gutters. These exterior features not only enhance the aesthetic appeal of your property but also play a crucial role in protecting your investment. Rain gutters efficiently channel rainwater away from your home’s foundation, preventing potential water damage and erosion. This practical feature is especially important in Florida’s rainy season, ensuring that your home remains a safe haven for you and your family.

In Winter Garden, you’ll find a variety of homes equipped with these essential rain gutters, offering peace of mind alongside stylish living. Whether you’re searching for a cozy bungalow or a spacious family home, the real estate options here are diverse and inviting. Come experience the charm of Winter Garden, where community spirit thrives and every home tells a story!

Newest Winter Garden Homes with Rain Gutters Exterior Features

2139 Tillman Avenue, Winter Garden
$825,000
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
$2,300,000
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
$399,900
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

5513 New Independence Parkway, Winter Garden
$575,000
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

8943 Lakeshore Pointe Drive, Winter Garden
$639,900
3 Beds ⋅ 3 Baths ⋅ Lakeshore Preserve Phase I SubDv. ⋅ 34787 Zip Code
ONE OF THE PRETTIEST LOCATIONS AND VIEWS IN LAKESHORE!! SHOWS BETTER THAN A MODEL WITH TOO MANY UPGRADES TO LIST!!! LOCATION, LOCATION, LOCATION!!! FROM THE TIME YOU ARRIVE, YOU WILL IMMEDIATELY FALL IN LOVE WITH THE OVERSIZED FRONT PORCH, WATERVIEW OF THE COMMUNITY FOUNTAIN, AND MORE THAN ENOUGH ROOM TO ENJOY OUTDOOR LIVING! THIS LUXURIOUS TOLL BROTHERS DANTE ITALIANATE FLOORPLAN HAS IT ALL! THIS HOME HAS AN OPEN CONCEPT WITH HIGH CEILINGS, LOTS OF WINDOWS ALLOWING FOR NATURAL LIGHT, HUGE SLIDING DOORS WHICH LEAD TO A PRIVATE BRICK PAVERED COURTYARD AND A COVERED WALKWAY TO YOUR TWO CAR GARAGE. WALK INTO YOUR SPACIOUS KITCHEN WHICH INCLUDES A MASSIVE ISLAND AND AN ADDITIONAL BREAKFAST BAR, BOTH WITH UPGRADED QUARTZ COUNTERTOPS. YOU WILL LOVE YOUR NEW KITCHEN WHICH INCLUDES AN UPGRADED CABINET PACKAGE ADDING ADDITIONAL CABINETS FOR AMPLE SPACE, 42" CABINETS, CROWN MOLDING, STAINLESS APPLIANCES AND NATURAL GAS FOR COOKING. MANY ENERGY SAVING FEATURES INCLUDING TANKLESS WATER HEATER, FOAM INSULATION, SOLID CONCRETE BLOCK WALLS FROM THE FOUNDATION THROUGH THE ATTIC AND MORE. ENJOY RESORT STYLE AMENITIES WHICH INCLUDE A POOL, FITNESS CENTER, CLUBHOUSE WITH BREATHTAKING LAKE AND GOLF COURSE VIEWS, KAYAK AND PADDLE BOARD LAUNCH, TWO PLAYGROUNDS, FIREPIT, SUMMER KITCHEN, HAMMOCKS AND DOG PARK. LAKESHORE PRESERVE IS LOCATED IN THE HAMLIN AREA, ONLY TEN MINUTES FROM MAJOR TOURIST ATTRACTIONS. YOU WILL ALSO FIND NEW SCHOOLS, NEW RESTAURANTS, NEW HOSPITAL, PLENTY OF SHOPPING AND ENJOY THE NEW CINEPOLIS RECENTLY BUILT - EASY ACCESS TO ALL THAT CENTRAL FLORIDA HAS!! SCHEDULE YOUR APPOINTMENT TODAY, YOU WILL NOT BE DISAPPOINTED!!!

8943 Lakeshore Pointe Drive, Winter Garden

5522 New Independence Parkway, Winter Garden
$499,900
3 Beds ⋅ 2 Baths ⋅ Signature Lakes, Independence SubDv. ⋅ 34787 Zip Code
Independence ** Rare floor plan for Independence with 3 bedrooms and +/-17x12' DEN or living room space ** FRESHLY painted neutral soft white interior and BRAND NEW LAMINATE FLOORING in the 3 bedrooms ** 19x10' Florida Room with AC and heat ** Primary bedroom has 2 walk in closets with built in white shelving & ensuite primary bath with two sinks, granite counters, garden tub and separate shower ** The kitchen has a large cooking island with granite counters and includes the stainless steel stove, refrig and dishwasher ** Laundry room with built in white shelving and washer and dryer included ** Ceiling fans in every room ** Great completely fenced back yard with Florida room and brick paver patio area 2018 ** 2 car attached garage ** Lovely front porch with brick patio pavers ** Beautiful Florida Room Other upgrades include: NEW Trane A/C SYSTEM 10/2025, NEW white vinyl fence and gates 2/2024, NEW exterior brass whole house water shutoff valve 3/2026, NEW garage door system, SPRINGS 2/2021 and garage door opener 10/2024 ** LOW HOA fees $194.69 incl cable & internet which currently includes HBO and Max! Incredible amenities including 2 community pools, play areas, a lg community park plus other neighborhood green space and play areas thru-out the neighborhood, loads of sidewalks & conservation thru-out... All room measurements are approximate from the Builder floor plan. Buyer to verify measurements. Square footage is from Orange County Appraiser records ** Refrigerator ice maker is not working **

5522 New Independence Parkway, Winter Garden

8163 Red Stopper Lane, Winter Garden
$455,000
3 Beds ⋅ 3 Baths ⋅ Summerlake Pd Ph 2c 2d 2e SubDv. ⋅ 34787 Zip Code
Discover the best of Winter Garden living in the highly desirable Summerlake community, where resort style amenities, convenient access to Orlando attractions, and beautiful neighborhood surroundings come together. Located at 8163 Red Stopper Lane, this beautifully maintained 3 bedroom, 2.5 bathroom home offers an inviting open concept floor plan designed for comfortable everyday living and entertaining. Step inside to a spacious main living area featuring ceramic tile flooring, abundant natural light, and a thoughtfully designed layout. The kitchen features granite countertops, 42 inch cabinetry with crown molding, a decorative tile backsplash, stainless steel appliances, a breakfast bar, and a generous pantry. The adjoining dining area provides additional space for gathering with family and friends. Upstairs, the spacious primary suite offers a special Florida experience with views of the Walt Disney World fireworks illuminating the night sky! The primary bathroom features dual sinks, stone countertops, an upgraded tiled shower, and a large walk in closet. Two additional bedrooms and a full guest bathroom complete the upstairs living space. Outside, enjoy your own private fenced courtyard with attractive pavers and a covered lanai, perfect for morning coffee, outdoor dining, or relaxing in the Florida sunshine. An attached two car garage provides convenient parking and additional storage. Summerlake is known for its exceptional community amenities, including a resort style swimming pool, clubhouse, fitness center, tennis courts, basketball courts, playground, dog park, zip line, and scenic walking trails. Located in the sought after Horizon West area of Winter Garden, residents enjoy convenient access to Hamlin Town Center for shopping, dining, and entertainment, along with nearby golf courses, parks, and outdoor recreation. Historic Downtown Winter Garden offers charming boutiques, local restaurants, a popular farmers market, and access to the West Orange Trail. With Walt Disney World, major Orlando attractions, and important Central Florida roadways nearby, this location offers an exceptional combination of neighborhood charm and everyday convenience. Whether you are looking for a primary residence or a seasonal Florida retreat, this Summerlake property offers the lifestyle and location that make Winter Garden one of Central Florida's most desirable places to call home. Schedule your private showing and discover everything this home and community have to offer!

8163 Red Stopper Lane, Winter Garden

14230 Sunridge Boulevard, Winter Garden
$629,900
3 Beds ⋅ 2 Baths ⋅ Cypress Reserve Ph 1 SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully maintained home in desirable Winter Garden, where comfort, style, and functionality come together! From the spacious front porch to the impressive 8-foot glass front door, this inviting home offers thoughtful upgrades and generous living spaces throughout. The elegant formal dining room features a tray ceiling and beautiful wooden plantation shutters, creating the perfect setting for special gatherings. The open-concept kitchen is a standout, featuring quartz countertops, a stylish tile backsplash, a center island with a deep sink, chrome faucet, pendant lighting, stainless steel appliances, a convenient butler's pantry, and a cozy breakfast nook. The spacious living room is equally impressive, showcasing an electric fireplace with a decorative mantel, recessed lighting, and double sliding glass doors that seamlessly connect indoor and outdoor living. Step outside to the expansive, custom-built, covered and screened patio, overlooking a fully fenced backyard, an ideal setting for entertaining guests, outdoor dining, or simply relaxing in privacy. Additional highlights include brand-new carpeting in all bedrooms and a professionally cleaned interior, making this home move-in ready! Residents enjoy a community swimming pool and a playground. Conveniently located near the popular Tucker Ranch Recreation and Nature Complex, with easy access to shopping, dining, and outdoor recreation, this home offers an exceptional combination of location, comfort, and lifestyle. Don't miss this wonderful opportunity to make this Winter Garden home your own. Schedule your private showing today!

14230 Sunridge Boulevard, Winter Garden

8270 Topsail Place, Winter Garden
$849,900
4 Beds ⋅ 3 Baths ⋅ Lakeshore Preserve Ph 5 SubDv. ⋅ 34787 Zip Code
Luxury Single-Story Pool Home in Lakeshore Preserve | 4BR/3BA | Disney Fireworks Views Enjoy luxury living in this heavily upgraded Toll Brothers home in Lakeshore Preserve, featuring a private pool with a brand new pool heater, no rear neighbors, and views of Magic Kingdom fireworks. The light-filled, open floor plan features 12-foot ceilings, 8-foot doors, and upscale lighting throughout the kitchen, dining area, and great room. The gourmet kitchen offers upgraded cabinetry, a butler’s pantry, quartz countertops, stainless steel appliances, a built-in wall oven, and an impressive 12-foot center island. The owner’s suite overlooks the pool and includes two walk-in closets and a spa-style bathroom with dual vanities and a frameless glass shower. The flexible layout includes a dedicated office with a closet that can serve as the fourth bedroom, a private guest suite with an ensuite bathroom and walk-in closet, and a third full bathroom off the hall. Outside, your backyard retreat awaits with a private pool, extended screened lanai, and oversized covered patio pre-plumbed for a summer kitchen. Take in peaceful sunrise views and enjoy Magic Kingdom fireworks after dark. Lakeshore’s resort-style amenities include a lakefront clubhouse, event room, fitness and yoga rooms, meditation room, zero-entry community pool with splash features, summer kitchen, sand volleyball, dock, trails, playgrounds, parks, fire pit, dog park, and kayak launch. Dining, shopping, schools, golf, and area attractions are just minutes away. HOA includes Wi-Fi and lawn care. Minutes to dining, shopping, schools, golf, and area attractions. Available for immediate occupancy; contact for a private showing.

8270 Topsail Place, 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

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