Winter Garden/Oakland Homes with Rain Gutters Exterior Features

Winter Garden/Oakland Homes with Rain Gutters Exterior Features

Welcome to the enchanting community of Winter Garden and Oakland, Florida, where charming small-town vibes meet the allure of modern living. Nestled just west of Orlando, this picturesque area is known for its lush landscapes, vibrant downtown, and rich history. With its scenic parks, delightful shops, and a thriving farmers' market, Winter Garden offers a delightful blend of outdoor recreation and community spirit.

As you explore the neighborhoods of Winter Garden and Oakland, you'll discover a variety of homes that cater to different lifestyles. One standout feature that many of these homes boast is their rain gutters. These exterior features are not just practical; they are essential for maintaining the integrity of your property. Rain gutters effectively direct water away from your home’s foundation, protecting it from potential damage and erosion. This thoughtful addition enhances the longevity of your home, allowing you to enjoy your beautiful residence worry-free.

Moreover, the homes in this region often reflect a harmonious blend of traditional charm and contemporary design. Whether you prefer a cozy bungalow or a spacious family home, you’ll find that many properties are equipped with rain gutters, ensuring that your investment remains in pristine condition throughout Florida’s diverse weather patterns.

Living in Winter Garden and Oakland means embracing a lifestyle filled with community events, outdoor adventures, and a strong sense of belonging. With its rich offerings and beautiful homes, your dream residence awaits in this charming corner of Florida. Come and discover the perfect blend of comfort and convenience in Winter Garden and Oakland today!

Newest Winter Garden/Oakland Homes with Rain Gutters Exterior Features

5 Beds ⋅ 5 Baths ⋅ Twinwaters SubDv. ⋅ 34787 Zip Code

Experience refined living in this exceptional 5-bedroom, 3-full and 2-half bath residence nestled in one of Winter Garden's most desirable communities. Thoughtfully designed with an open-concept floor plan, the expansive great room seamlessly connects to the gourmet kitchen, creating an inviting space for both everyday living and elegant entertaining. The first-floor primary suite offers a private retreat, complete with a spacious layout and spa-inspired bathroom. The primary bath connects to your California style closet and laundry room. Throughout the home, you'll appreciate upscale finishes, including designer lighting, elegant flooring, stone countertops, stainless steel appliances, and architectural details that elevate every space. New carpets and a new Kitchen Aid refrigerator installed in July 2026. Large windows fill the home with natural light, enhancing the bright and airy atmosphere. Four additional bedrooms located upstairs with jack and jill style bathrooms. This home has two bonus areas for maximum entertaining potential, comfort and functionality. This home is also equipped with a whole house water softener, Tesla charger and Govee lights. The backyard is set for entertainment with your summer kitchen, firepit and turf grass. Ideally located near premier shopping, dining, entertainment, parks, and top-rated schools, this home combines luxury, convenience, and timeless style in the heart of Winter Garden. A rare opportunity to own a beautifully appointed turn-key ready home in an exceptional location.

1664 Holcomb Creek St., Winter Garden

3 Beds ⋅ 3 Baths ⋅ Encore/Ovation Ph 3 SubDv. ⋅ 34787 Zip Code

A Rare Opportunity in Encore at Ovation! This beautifully upgraded Jensen model is back on the market! Located just off Disney's Western Way, this exceptional home offers timeless designer finishes, an open-concept floor plan, and an unbeatable location just minutes from Walt Disney World. The stunning kitchen features 42-inch shaker cabinets, quartz countertops, an oversized island, dovetail drawers, and upgraded lighting. Waterproof wood-look flooring flows throughout the main level, while extra-height baseboards add a custom touch. The spacious primary suite includes a tray ceiling and a luxurious bath with a designer-tiled walk-in shower and semi-frameless glass enclosure. Bathrooms feature granite countertops and slate-look porcelain tile, with plush carpeting upstairs. A standout feature is the private backyard exclusive to this floor plan creating the perfect space to relax or entertain. Walt Disney World and Margaritaville Resort Orlando are both nearby, as well as premier shopping, dining, and entertainment. Don't miss this opportunity to own one of Encore at Ovation's most desirable homes. Schedule your private showing today!

13879 Lanyard Way, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Chapin Station A SubDv. ⋅ 34787 Zip Code

Welcome home to this beautifully maintained pool home in the desirable Chapin Station community of Winter Garden, where location truly sets it apart. Just outside the neighborhood, you'll enjoy direct access to the West Orange Trail at the Chapin Station Trailhead, making it easy to bike, walk, run, or explore miles of scenic trails connecting Winter Garden, Clermont, Oakland, and beyond. Situated on an oversized homesite, this property offers the perfect blend of indoor comfort and outdoor Florida living with a private screened pool and spacious backyard ideal for entertaining and relaxing. Inside, you'll find a thoughtfully designed floor plan with generous living spaces, abundant natural light, and plenty of room for everyday living and hosting family and friends. Conveniently located just minutes from Historic Downtown Winter Garden, residents can enjoy the award winning Farmers Market, Plant Street, Crooked Can Brewing Company, boutique shopping, restaurants, live entertainment, and community events throughout the year. Downtown Clermont, Winter Garden Village, major highways including SR 429 and the Florida Turnpike, Walt Disney World Resorts, Disney Springs, world class sports training facilities, championship golf, and state of the art hospitals and medical centers are all within easy reach. This exceptional home combines an unbeatable location, outdoor recreation, convenient access to Central Florida's top attractions and amenities, and the vibrant lifestyle buyers are searching for.

1339 Hunterman Lane, Winter Garden

4 Beds ⋅ 5 Baths ⋅ Winter Garden Shores 2nd Add SubDv. ⋅ 34787 Zip Code

Discover elevated living and the Winter Garden lifestyle in downtown's newest custom residence! Ideally positioned off the shores of Lake Apopka and within the beloved golf cart district, this exceptional home offers effortless access to Plant Street’s charming shops, restaurants, Farmers Market, Brewery and West Orange Trail. Thoughtfully designed by locals with a deep appreciation for the character of this historic city, this exquisite 4 bedroom, 4.5-bath home blends timeless charm with refined modern finishes throughout. Majestic oaks beautifully frame the home’s craftsman-inspired architecture, while the expansive front porch invites relaxation. Inside, an open-concept design and modern kitchen are curated for both everyday comfort and endless entertaining. Inviting living spaces are complemented by elevated finishes, a wine bar, custom built-ins, a butler’s pantry & outdoor kitchen. Creatively designed to include a drop zone with a one-of-a-kind dog wash station. All bedrooms feature ensuites and custom closets. Don't miss this one-of-a-kind opportunity. Schedule your private showing today!

412 N Boyd Street, Winter Garden

2 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code

Welcome to this beautifully maintained 2-bedroom, 2-bath first-floor unit with a 1-car garage, located in the highly desirable gated community of Southern Pines in the heart of Winter Garden. Offering the perfect combination of comfort, convenience, and resort-style living, this home is ideal for first-time buyers, downsizers, investors, or anyone seeking a low-maintenance lifestyle. The thoughtfully designed floor plan features spacious living areas, two generously sized bedrooms, and two full bathrooms, all conveniently situated on the first floor for easy access. Enjoy the added value of water, internet, and cable included in the monthly Condo fee, making everyday living both simple and budget-friendly. Southern Pines is known for its outstanding amenities, offering residents a true resort-style experience. Spend your days relaxing by the sparkling pool and hot tub, entertain friends at the BBQ grills and outdoor kitchen, or enjoy the beautifully appointed clubhouse featuring a movie theater, business center, and billiards room. Stay active with the fully equipped fitness center, indoor basketball and racquetball courts, tennis courts, beach volleyball court, and a covered outdoor playground. Additional conveniences include a car wash station and beautifully maintained grounds throughout the community. Ideally located just minutes from Historic Downtown Winter Garden, Winter Garden Village, major highways including SR-429 and the Florida Turnpike, shopping, dining, entertainment, and world-renowned theme parks, this condo offers an unbeatable location with exceptional amenities. Don't miss your opportunity to own a piece of one of Central Florida's most sought-after communities!

405 Southern Pecan Circle Unit 108, Winter Garden

5 Beds ⋅ 4 Baths ⋅ Westfield Lakes SubDv. ⋅ 34787 Zip Code

Welcome Home! Meticulously maintained home boasting with upgrades on an oversized conservation lot with peaceful pond views. Designed for both everyday living and entertaining, features a completely remodeled kitchen with quartz countertops, premium Café appliances, designer backsplash, a massive island with sitting space, upgraded lighting and a custom walk-in pantry. The first floor includes a private office, spacious family room, guest suite with a full bath, laundry room, formal living, and dining room. Porcelain tile flows throughout the main living areas, French doors lead to your private backyard retreat with a fully screened lanai overlooking the saltwater pool and spa, complete with new tile. Upstairs you'll find a stunning media room complete with theater seating and a granite wet bar, 4 bedrooms and a full bath. The primary suite features tray ceiling, plantation shutters, dual walk-in closets, and remodel ensuite bath. Updates include dual vanities, walk-in glass shower, clawfoot tub, and stunning upgraded tile throughout. Two car garage with an upgraded paver driveway. Located in a highly sought-after community of Westfield Lakes. Excellent public schools and convenient access to shopping, dining, and major highways, this exceptional home offers the perfect combination of luxury, comfort, and location. Schedule a private showing today!

626 English Lake Drive, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Lakeview Preserve Rep SubDv. ⋅ 34787 Zip Code

Space, style, and a true lake-community lifestyle come together in this thoughtfully designed home in the gated community of Lakeview Preserve. With a flexible floor plan, generous living spaces, and room to grow both inside and out, this home offers the perfect blend of comfort, functionality, and Florida living. The open-concept layout is designed for both entertaining and everyday living. At the heart of the home, the kitchen features white shaker cabinetry, quartz countertops, stainless steel appliances, a walk-in pantry, and an oversized island with seating for four. It flows seamlessly into the dining area and spacious living room, creating a welcoming space for everything from weeknight dinners to holiday gatherings. French doors off the foyer lead to a dedicated office, providing flexibility for working from home, a playroom, hobby space, or a quiet retreat. Tucked away on the first floor, the private primary suite features dual vanities, a soaking tub, glass-enclosed shower, and a generous walk-in closet. Upstairs, the expansive bonus room offers endless possibilities as a media room, game room, playroom, or second living area. The additional bedrooms provide comfortable accommodations for family and guests, giving everyone space to spread out. Step outside to the covered brick-paver lanai overlooking the fully fenced backyard, where there's plenty of room for outdoor entertaining, pets, play, gardening, or even a future pool. Whether you're enjoying a quiet morning or hosting friends for a weekend barbecue, the outdoor space is ready to fit your lifestyle. Life in Lakeview Preserve is about more than just the home. Set along the shores of Johns Lake, this gated community embraces an active Florida lifestyle with amenities designed for all ages. Residents enjoy a resort-style pool, splash pad, fitness center, clubhouse and community cabana, playground, community dock, and kayak launch with direct access to Johns Lake for boating, fishing, and paddling. Conservation areas woven throughout the neighborhood enhance the natural beauty, creating a peaceful setting while keeping you close to everything Winter Garden has to offer. Conveniently located just minutes from SR 429, Winter Garden Village, historic Downtown Winter Garden, shopping, dining, parks, and everyday conveniences, this home offers the ideal balance of space, convenience, and community. Whether you're looking for room to grow, space to entertain, or a neighborhood built around an active Florida lifestyle, this home offers the flexibility to fit your lifestyle while creating lasting memories.

3247 Buoy Circle, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Lakeshore Preserve Ph 1 SubDv. ⋅ 34787 Zip Code

Luxurious upgraded TOLL BROTHERS Townhome located in coveted Lakeshore Preserve! As you enter this Immaculate 3-bedroom, 2.5-bathroom townhouse the living area offers a bright spacious open floor plan with 10' ceilings and upgraded kitchen area perfect for entertaining or simply bringing out your inner chef! The large center island provides plenty of space for multiple people to enjoy and an additional generous sized counter invites guests to join all activities centered in the kitchen. Featuring 42" upgraded cabinets, stainless steel appliances and a natural gas range, the area has sliding glass doors that open up to the private patio so that enjoying the outdoors becomes effortless. Outside, a covered walkway leads to the 2-car garage located across the beautifully paved patio. Moving upstairs, the primary bedroom is a tranquil retreat with a generous sized walk-in closet and an ensuite bathroom with dual sinks and at private water closet. From the relaxing bedroom you can enjoy beautiful sunsets in the evening without leaving the comfort of your home. Located on the other side of the second floor are two comfortable bedrooms that share a spacious bathroom across the hall. In addition, the home offers a whole house water filtration system, tankless water heater and above head storage racks in the garage. If you are ready to enjoy resort style living, Lakeshore Preserve also offers plenty of activities with a beautiful clubhouse with fitness center, outdoor community pool and playgrounds nestled along the shores of Panther Lake. Whether you enjoy going for a stroll along one of the walkways or grabbing a seat in one of the beautifully landscaped park areas, you are sure to find a quiet place with views. Best of all, your HOA dues cover not only all the amenities, but also exterior maintenance of your townhome, exterior painting, roof cleaning, and basic cable and internet. This well-maintained townhome in Horizon West is close to top rated schools, Disney attractions, shopping, dining, and has easy access to HWY 429.

8932 Bismarck Palm Drive, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 1b SubDv. ⋅ 34787 Zip Code

Welcome to your beautiful water-view home in the highly sought-after Waterleigh community! This stunning property offers the convenience of single-story living with 4 bedrooms, 3 full bathrooms and picturesque water views. Perfectly positioned with a large green space in front and stunning pond and lake views in the back, this home features a gated backyard offering added privacy and convenient outdoor access. End your evenings by enjoying a glimpse of Disney's nightly fireworks right from your own backyard. Inside, you'll find numerous recent updates, including a new HVAC system, brand-new carpet, a new refrigerator, new dishwasher, new garbage disposal, and a new washer and dryer, making this home truly move-in ready! One of the many perks of living in Waterleigh is that lawn care is included in the HOA, allowing you to spend more time enjoying the exceptional resort-style amenities. Residents have access to resort-style pools, state-of-the-art fitness centers, beautiful clubhouses, mini golf, a dog park, expansive sports fields, multiple playgrounds, beach volleyball, tennis courts, a community dock, and scenic walking trails and picnic areas, creating the perfect setting for an active and relaxing lifestyle. Ideally located in the heart of Horizon West, just minutes from Walt Disney World with quick access to SR-429, this home offers easy commuting throughout Central Florida while being zoned for highly rated schools. This is a rare opportunity to own a beautifully updated home with exceptional views in one of Horizon West's most desirable communities. Schedule your private showing today!

16130 Wind View Lane, Winter Garden

5 Beds ⋅ 4 Baths ⋅ Lakeview Pointe At Horizon West SubDv. ⋅ 34787 Zip Code

WELCOME TO LAKEVIEW POINTE AT HORIZON WEST! This 5-bedroom, 4-full-bath Pulte Creekview floorplan offers a flexible two-story layout with a downstairs primary suite, upstairs loft, flex room, 3-car garage, and a fully fenced corner-lot backyard. Hardwood flooring extends throughout the first floor, complemented by tray ceilings in the foyer and primary suite, plantation shutters, neutral interior paint, and updated lighting in the flex space and breakfast nook. The open kitchen, café, and family room create a central gathering space, featuring 42-inch maple cabinetry with crown molding and hardware, granite countertops, an oversized island with breakfast bar seating, built-in wall oven and microwave, corner walk-in pantry, and extended cabinetry along the breakfast nook for additional storage. Glass sliders with a remote-controlled window treatment open to the covered, extended screened brick-paver patio overlooking the private fenced yard. The downstairs primary suite includes a tray ceiling, oversized walk-in closet, dual-sink granite vanity, glass-enclosed tiled walk-in shower, and private water closet. Three additional bedrooms are located downstairs, including one adjacent to a full bath with dual-sink granite vanity, while two bedrooms share another full bath. Upstairs, a loft, storage room, fifth bedroom with extensive closet space, and a fourth full bath provide versatile space for guests, work, hobbies, or media use. Recent improvements include interior and exterior paint, two new AC systems installed in 2025, ceiling fans, bathroom mirrors, front door hardware, epoxy-finished garage floor, and overhead garage storage racks. Kitchen appliances, washer, and dryer convey. A transferable Choice Home Warranty is included through May 2027, subject to warranty terms. Lakeview Pointe HOA includes lawn care, irrigation, community pool, fitness center, playground, and additional community amenities. Convenient Horizon West location near Hamlin shopping and dining, SR-429, Winter Garden Village, Walt Disney World Resort, and major Central Florida attractions.

7052 Enchanted Lake Drive, Winter Garden

5 Beds ⋅ 5 Baths ⋅ Hickory Hammock Ph 1d SubDv. ⋅ 34787 Zip Code

Commanding stunning views of Johns Lake, 16038 Johns Lake Overlook Dr rests in the desirable Hickory Hammock community of Winter Garden a lakefront enclave where natural beauty meets elevated, everyday luxury. This is more than a home; it's a lifestyle designed for those who appreciate space, comfort, and the calming presence of water just beyond their windows. Inside, 4,139 square feet unfold across a thoughtful, flexible layout with five bedrooms and five bathrooms. The main level anchors the home with two generous suites, including a refined primary and an oversized guest suite. Each offers serene water views, spa-inspired bathrooms, and a true sense of privacy that makes hosting effortless. Venture upstairs to discover a second secluded primary suite your personal sanctuary. Here, you can wake to panoramic lake views, relax in the garden bath, or step onto your private balcony to take in unforgettable sunsets over the water. The heart of the home is an open concept living area that flows seamlessly into a chef's dream kitchen. Premium appliances, gleaming granite countertops, and custom cabinetry create a space equally suited for quiet mornings and lively gatherings. When it's time to unwind, a dedicated theatre loft provides the perfect setting for movie nights and lazy weekend afternoons. Step outside, and the entertaining possibilities feel endless. The expansive outdoor living area boasts a full outdoor kitchen finished in Brazilian granite, a sparkling pool with an infinity edge hot tub, and multiple spaces for lounging and dining beneath the Florida sky. Just steps away, your covered private boat dock complete with boat and jet ski lifts opens the door to endless days of boating, fishing, and watersports on Johns Lake. For those who love to play, the backyard even includes a 5-hole putting green and a 2-hole chipping green, ideal for sharpening your short game without ever leaving home. Every detail here reflects a rare blend of craftsmanship, comfort, and connection to the water. Surrounded by natural beauty and premium amenities, this property delivers the kind of tranquil lakefront living that so many search for and so few ever find. Opportunities to own a home like this, in one of Winter Garden's most sought after communities, simply don't come along often. Come experience it for yourself, and imagine the life waiting here. Schedule your private showing today before this exceptional retreat is gone!

16038 Johns Lake Overlook Drive, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Waterleigh Ph 3b 3c & 3d SubDv. ⋅ 34787 Zip Code

Welcome to this beautifully maintained Laurel floor plan, featuring fresh professional exterior paint (2026), 3 bedrooms, 2 bathrooms, and an open-concept layout thoughtfully designed for comfortable everyday living and effortless entertaining. The spacious kitchen serves as the heart of the home, featuring stainless steel appliances, a breakfast bar, a walk-in pantry, and an adjoining dining area that flows seamlessly into the living room. Elegant ceramic tile extends throughout the main living areas, while the abundant natural light create a bright, inviting atmosphere. The private primary suite offers a generous walk-in closet and an ensuite bath with dual vanities and a large walk-in shower. Two additional bedrooms are thoughtfully positioned toward the front of the home, providing flexibility for guests, a home office, or hobbies. Enjoy Florida living year-round on the private brick-paver patio, with additional upgrades including an epoxy-coated garage floor, overhead storage racks, seamless gutters, upgraded front elevation with brick accents, and a rear-entry garage for enhanced curb appeal. Located in the Waterleigh master-planned community, residents enjoy resort-style amenities including multiple pools, fitness centers, walking trails, parks, playgrounds, sports courts, community gardens, and scenic lakes. Conveniently located near Horizon West, Hamlin Town Center, New Publix, shopping, dining, major roadways, Walt Disney World, and everything Winter Garden has to offer. Don't miss the opportunity to own this move-in-ready home in one of Central Florida's most desirable communities.

16802 Oakboro Street, Winter Garden

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