Winter Garden Homes with Rain Gutters Exterior Features

Winter Garden Homes with Rain Gutters Exterior Features

Winter Garden, located in Orange County, Florida, is a vibrant city with a rich history and a promising future. Known for its charming small-town atmosphere and close-knit community, Winter Garden offers residents a high quality of life and a range of amenities.

One notable feature of homes in Winter Garden is the inclusion of rain gutters as an exterior feature. These rain gutters serve a crucial role in protecting the homes from water damage by directing rainwater away from the foundation. This feature ensures that the homes remain in excellent condition and reduces the risk of issues such as flooding or erosion.

The presence of rain gutters in Winter Garden homes is a testament to the city's commitment to maintaining the integrity of its properties. It reflects the attention to detail and the focus on long-term durability that homeowners and builders in Winter Garden prioritize.

With its picturesque streets, well-maintained homes, and lush landscapes, Winter Garden is a haven for those seeking a peaceful and picturesque place to call home. Whether you're looking for a cozy single-family home or a spacious estate, Winter Garden offers a variety of housing options to suit different preferences and budgets.

In addition to its beautiful homes, Winter Garden boasts a vibrant downtown area, with charming shops, restaurants, and entertainment venues. Residents can enjoy leisurely strolls along the West Orange Trail, explore local parks, or take part in community events and festivals.

For those seeking a city that combines small-town charm with modern amenities, Winter Garden is an ideal choice. Its commitment to preserving the beauty of its homes through features like rain gutters is just one example of the city's dedication to providing a high standard of living for its residents.

Newest Winter Garden Homes with Rain Gutters Exterior Features

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
12822 Sunset Walk Drive, Winter Garden
$528,396
3 Beds ⋅ 3 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Welcome to the Crowley townhome by Toll Brothers in the desirable Winter Garden/Horizon West area. This beautifully designed home features an open-concept layout connecting the great room, kitchen, and dining area. Enjoy outdoor living in the private courtyard with direct access to the detached 2-car garage. The spacious primary suite offers a large walk-in closet and a well-appointed bathroom with dual vanities and a separate shower. Experience stylish, low-maintenance living in one of Central Florida’s most desirable locations.

12822 Sunset Walk Drive, Winter Garden
12826 Sunset Walk Drive, Winter Garden
$539,239
4 Beds ⋅ 3 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Toll Brothers New Construction in Horizon West with estimated completion in early 2027! This beautiful townhome features 4 bedrooms and 3 full bathrooms, including a first-floor bedroom and full bath, plus 3 bedrooms and 2 bathrooms on the second level. Enjoy an open-concept kitchen, dining area, and spacious great room with access to a private courtyard. The primary suite offers a large walk-in closet and a private bath with dual vanities and a separate shower. Conveniently located near shopping, dining, top-rated schools, and major roadways. Don't miss this opportunity!

12826 Sunset Walk Drive, Winter Garden
1076 Sadler Oaks Way, Oakland
$1,570,000
4 Beds ⋅ 4 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code
*** A RARE Offering in Oakland Park | Custom-Built Luxury | ONE-STORY Living *** An exceptional opportunity to own a custom-built residence in the highly sought-after community of Oakland Park, where timeless architectural details, refined finishes, and an extraordinary setting come together. This beautifully appointed 4 bedroom, 3.5 bath home with mudroom and OVERSIZED garage (2.5), with more than 700 square feet of space, offers a highly desirable feature rarely found in Oakland Park: a thoughtfully designed, single-story floor plan with TWO spacious PRIMARY suites. Situated on a premium corner lot, nearly a QUARTER acre, the property enjoys an exceptional sense of privacy, with mature oak trees, no rear neighbors, and a neighboring park, providing additional open space and lasting privacy. Inside, soaring vaulted ceilings, stunning WOOD flooring, elegant crown molding, a cozy FIREPLACE, and an impressive collection of custom millwork, including shiplap accents and exposed timber details, establish a warm yet sophisticated aesthetic appearance. The heart of the home is an expansive, open-concept kitchen and great room designed for both everyday living and effortless entertaining. The beautifully appointed kitchen features custom-panel THERMADOR appliances, including a 6 burner GAS cooktop, built-in oven and microwave, a walk-in pantry, and a coffee bar conveniently connected to the formal dining room. A charming breakfast nook completes this exceptional gathering space. One of the home’s most distinctive features is the expansive screened-in courtyard, creating a seamless extension of the indoor living areas. Finished with elegant travertine pavers, this private outdoor retreat features a kitchen complete with a grill and sink, making it ideal for entertaining or simply enjoying the Florida lifestyle. The generous courtyard also presents an exciting opportunity for a future swimming POOL, allowing the next owner to further customize the space. A separate covered rear porch and welcoming front porch provide additional opportunities to enjoy the home’s beautiful surroundings. The primary suite toward the back of the home includes a comfortable sitting area and an oversized eight-foot sliding glass door opening directly to the courtyard. The luxurious en-suite bath offers a quartz-topped vanity, walk-in shower, and garden tub. The second primary suite features an adjacent full bath and its own courtyard access, ideal for multigenerational living, visiting guests, or an extended-stay retreat. Two additional bedrooms with walk-in closets are towards the back of the home along with a full bath. A conveniently located half bath serves the main living areas and has access to the courtyard. The home is a short GOLF-CART ride to Historic Downtown Winter Garden's award-winning restaurants, shopping, farmers market, and events. This golf-cart-friendly waterfront community offers two pools (one resort styled pool), a clubhouse, parks, playgrounds, dog park, lake-side walking trails, and access to the 22-mile West Orange Trail, with easy reach to interstate travels, golf, and world-renowned theme parks. More than a home, it is the Winter Garden lifestyle. A rare combination of one story custom craftsmanship, privacy, exceptional outdoor living, and an irreplaceable location along the West Orange Trail, this remarkable Oakland Park residence offers a lifestyle that is increasingly hard to find.

1076 Sadler Oaks Way, Oakland
12818 Sunset Walk Drive, Winter Garden
$659,008
4 Beds ⋅ 4 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Toll Brothers New Construction in Horizon West with estimated completion in early 2027! This unique townhome features 4 bedrooms and 3 full bathrooms, including a first-floor bedroom and full bath, plus 3 bedrooms and 2 bathrooms on the second level. A private loft and full bathroom above the detached garage provide additional flexible living space, perfect for guests, multigenerational living, or a home office. Enjoy an open-concept kitchen, dining area, and great room with access to a private courtyard. Conveniently located near shopping, dining, top-rated schools, and major roadways. Don't miss this unique opportunity!

12818 Sunset Walk Drive, Winter Garden
12834 Sunset Walk Drive, Winter Garden
$636,947
4 Beds ⋅ 4 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Under Construction – Estimated Completion Early 2027! Welcome to the beautiful Autumn townhome, offering 2,447 square feet, 4 bedrooms, 4 bathrooms, and a versatile flex room and loft. The open concept main living area features a spacious kitchen with designer backsplash, modern cabinetry, and upgraded countertops, flowing seamlessly into the great room and casual dining area. Upstairs, the private primary suite includes a spacious walk-in closet, along with two additional bedrooms. A fourth bedroom and full bathroom are located on the first floor along with a loft and bathroom above the detached two-car garage. This provides additional flexibility and privacy. Enjoy a private rear courtyard and future resort-style community amenities. Closing cost assistance available! Schedule your appointment today!

12834 Sunset Walk Drive, Winter Garden
17152 Arrowhead Boulevard, Winter Garden
$449,000
4 Beds ⋅ 2 Baths ⋅ Arrowhead Lakes SubDv. ⋅ 34787 Zip Code
Spectacular fully renovated Mother-in-Law suite in 2026, with lake views! 4 bedrooms, 2 bathrooms total, completely independent from each other. Full renovation: brand new walls, floors, ceilings and bathrooms. All plans completed by a certified engineer and all inspections approved by Orange County, including the final inspection, move-in ready with zero worries! The property is divided into two units: each with 2 bedrooms, 1 bathroom, its own kitchen, laundry, A/C and individual water heater. Both units feature a private entrance, independent access to the backyard and their own driveway. No HOA, no restrictions, total freedom. Park your trailer, boat or work vehicle without asking anyone for permission. Perfect for a large or extended family, multi-generational living, or investors looking for a turnkey property with flexible use potential. Located in Winter Garden, just 11 minutes from Walt Disney World and with easy access to SR-429 and I-4, the best of peaceful lakeside living, with everything nearby. An opportunity that won't come around again!

17152 Arrowhead Boulevard, Winter Garden
12922 Canopy Woods Way, Winter Garden
$1,525,000
5 Beds ⋅ 5 Baths ⋅ Canopy Oaks Ph 1 SubDv. ⋅ 34787 Zip Code
EXQUISITE MODEL SHOW HOME | 5 BEDROOMS | 4.5 BATHROOMS | TWO PRIMARY SUITES | POOL | 3-CAR GARAGE | GATED COMMUNITY Welcome to an exceptional residence where timeless Mediterranean architecture meets refined Florida living. Located within the exclusive gated community of Canopy Oaks, an intimate enclave of only 49 residences, this stunning former model show home represents the finest in architectural design, craftsmanship, and luxurious indoor-outdoor living. From the impressive grand entrance, this residence immediately makes a statement. The thoughtfully designed floor plan features 5 bedrooms, 4.5 full bathrooms, a private first-floor primary suite with wet bar, and a spectacular second-floor primary retreat, offering an unparalleled level of flexibility and privacy. The heart of the home is an impressive chef's kitchen, beautifully appointed with premium KitchenAid appliances, a 5-burner natural gas cooktop, abundant cabinetry, generous workspace, and an oversized walk-in pantry. The kitchen opens seamlessly to the expansive living, dining and custom wine cellar, creating an ideal setting for intimate dinners or entertaining. The first floor also features a dedicated den/office, elegant dining area, wine cellar, laundry room, and convenient half-bath powder room. A beautiful wood staircase leads to the second level, where luxury and entertainment continue. The expansive gathering room provides an inviting space for family and guests, while the fully equipped theater room creates an exceptional private cinema experience, complete with its own private beverage station. The upstairs primary suite is a private sanctuary, featuring a beautiful garden tub, private balcony, and its own refreshment bar—an indulgent retreat designed for comfort and relaxation. Three additional upstairs bedrooms provide generous accommodations, including one bedroom with its own adjacent full bathroom and two bedrooms connected by a convenient Jack-and-Jill bath. The home's extraordinary outdoor living spaces are equally impressive. The expansive screened-in lanai features custom wood ceilings, creating a beautiful extension of the interior living space. Beyond the lanai, a sparkling private pool is surrounded by elegant travertine decking and complemented by a spectacular custom summer kitchen, creating the ultimate setting for Florida entertaining, dining, and relaxation. Additional features include a Rampart security system, Generac Generator, Central vacuum, exceptional storage, and the quality and attention to detail expected of a showcase model residence. The Canopy Oaks models were recognized with three awards in the Parade of Homes, highlighting the exceptional design and craftsmanship found throughout this exclusive community. Perfectly positioned just minutes from Winter Garden Village and Historic Downtown Winter Garden, this home also offers convenient access to the Florida Turnpike, SR 429, and SR 408, providing an easy connection throughout Central Florida. 12922 Canopy Woods Way is more than a home—it is a statement of refined living. With its timeless Mediterranean architecture, two extraordinary primary suites, resort-style pool and outdoor living, premium entertaining spaces, and exclusive gated setting, this is a truly remarkable opportunity to own one of Winter Garden's exceptional residences. Call today to schedule your showing and experience its distinctive luxury and elegance firsthand.

12922 Canopy Woods Way, Winter Garden
17316 Melogold Way, Winter Garden
$530,047
3 Beds ⋅ 3 Baths ⋅ Northlake At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Enjoy convenient, low-maintenance living in this two-story townhome featuring a two-car garage, perfectly located in the heart of Winter Garden. Designed for both comfort and functionality, this home offers a smart layout ideal for everyday living and entertaining. This popular Walden plans features finishes from the AW Collection Milan with clean, modern touches. The kitchen boards 42" cabinets, quartz countertops and tiled backsplash. Additional highlights include a detached two-car garage with private fenced courtyard space and upgraded 8' doors. Ideally situated, you’re just 37 minutes from Orlando International Airport, 20 minutes from world-famous Disney theme parks, and 30 minutes from Celebration. The community is also zoned for great schools and is minutes from downtown Winter Garden, where charming streets, local history, shopping, dining, and community events create a vibrant lifestyle. With its prime location and practical design, this townhome delivers the perfect blend of convenience, comfort, and Central Florida living. *Representation images and renderings are for illustrative purposes. Actual options and design finishes of home may vary.

17316 Melogold Way, Winter Garden
215 S Woodland Street, Winter Garden
$425,000
4 Beds ⋅ 2 Baths ⋅ Fries Survey Of Winter Garden SubDv. ⋅ 34787 Zip Code
Virtually Staged. LOCATION, LOCATION, LOCATION! Just ONE BLOCK SOUTH OF PLANT STREET in the heart of historic Downtown Winter Garden, this is the kind of opportunity that doesn’t come around every day! With a 6,933-square-foot lot, an existing four-bedroom, two-bathroom home, and a mother-in-law suite, this property offers something increasingly difficult to find: a prime downtown address with incredible possibilities for the future. In real estate, you can change almost anything about a property, but you can never change its location. And this one is exceptional! Situated just steps from the charm, character, and energy of Downtown Winter Garden, you’ll find yourself surrounded by some of Central Florida’s most beloved restaurants, coffee shops, boutiques, breweries, and community gathering spots. Spend your Saturday mornings exploring the award-winning Winter Garden Farmers Market, enjoy an afternoon along the West Orange Trail, or take an evening stroll down Plant Street for dinner and live entertainment. This is the walkable, golf-cart-friendly downtown lifestyle so many buyers dream about! The existing residence offers 1,685 square feet of living space with four bedrooms, two bathrooms, and the added flexibility of a mother-in-law suite. Whether you’re looking for a home with room for extended family, a property to personalize, or a place to establish your roots in one of Central Florida’s most desirable communities, there’s plenty of opportunity to make this address your own. But perhaps the most exciting feature isn’t just what’s standing on the property today. It’s the LAND and the LOCATION! With approximately 6,933 square feet just one block from Plant Street, this parcel presents a compelling opportunity for buyers who recognize the long-term appeal of owning property in the heart of Downtown Winter Garden. Bring your creativity, explore renovation possibilities, or investigate future improvements and redevelopment options, subject to city zoning and approval requirements. As Downtown Winter Garden continues to attract buyers seeking character, convenience, and a true sense of community, opportunities to secure property this close to the center of it all are especially appealing. Whether you’re a homeowner with a vision, an investor seeking a desirable location, or someone who’s always dreamed of living steps from Plant Street, this property deserves your attention. THE LOCATION IS ALREADY PERFECT. THE POSSIBILITIES ARE YOURS TO EXPLORE. Don’t miss your opportunity to own a piece of Downtown Winter Garden!

215 S Woodland Street, Winter Garden
1414 Portmoor Way, Winter Garden
$640,000
4 Beds ⋅ 3 Baths ⋅ Stoneybrook West 44/134 SubDv. ⋅ 34787 Zip Code
Video is virtually staged. Enjoy the best of both worlds in this beautiful pool home overlooking the Stoneybrook West Golf Course, where peaceful surroundings, beautiful views, and an abundance of community amenities create the perfect lifestyle. With NO REAR NEIGHBORS and a location OVERLOOKING THE GOLF COURSE on quiet Portmoor Way, you can relax while having plenty of opportunities to stay active, socialize, and connect with neighbors. The curb appeal is welcoming as is the spacious foyer, tall ceilings, and WOOD FLOORS. The well-appointed kitchen features QUARTZ countertops, tile backsplash, stainless steel appliances, and a WALK-IN PANTRY. Enjoy the breakfast nook that opens to the family room, creating a comfortable gathering space with beautiful views of the SCREENED-IN POOL and golf course. The spacious primary suite is conveniently located downstairs and offers a large walk-in closet, an updated vanity with double sinks, a garden tub, separate shower, and linen closet. Upstairs, you'll find AIRY LOFT, laundry room with cabinet storage, three additional bedrooms, and a hall bathroom with double sinks. Additional interior highlights include a formal dining room, a PRIVATE OFFICE with stylish barn doors, and an attractive staircase with iron railing and an accent wall. The home also offers valuable updates, including a NEW ROOF (2022), AC (2019), upgraded light fixtures, tile flooring in the garage, and rain gutters. One of the greatest benefits of living in Stoneybrook West is the incredible lifestyle included with your HOA! SPECTRUM CABLE AND INTERET ARE INCLUDED IN THE HOA DUES. Spend sunny afternoons at the Olympic-sized COMMUNITY POOL and splash pad, meet neighbors at the clubhouse and FITNESS CENTER, or enjoy friendly competition on the BASKETBALL, PICKELBALL, VOLLEYBALL and TENNIS courts. For those who love the water and outdoors, the community also offers a BOAT RAMP, limited BOAT STORAGE, and a FISHING pier. Stoneybrook West is conveniently located near highly regarded schools, restaurants, shopping, major roadways including the 429, Turnpike and 408, historic downtown Winter Garden, and Central Florida's world-famous theme parks.

1414 Portmoor Way, Winter Garden
239 Largovista Drive, Oakland
$670,000
4 Beds ⋅ 3 Baths ⋅ Johns Landing SubDv. ⋅ 34787 Zip Code
Welcome to this well-maintained home in the gated community of John's Landing! With 4 bedrooms, 2.5 baths, a spacious bonus broom, and a separate office that could be converted back to a bedroom, there's plenty of room to make this home fit your needs. The Kitchen features a cozy nook for everyday meals, while the enclosed patio- with its built-in bar and entertaining area- is ready for relaxing or gathering with family and friends.The roof and water heater are approximately 3 years old. Enjoy the space, flexibility, and community amenities John's Landing has to offer. Come see if this homies the right fit for you!

239 Largovista Drive, Oakland
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