Winter Garden/Oakland Homes with Dog Run Exterior Features

Winter Garden/Oakland Homes with Dog Run Exterior Features

Welcome to the charming community of Winter Garden and Oakland, nestled in the heart of Orange County, Florida. This picturesque region is renowned for its vibrant downtown, lush parks, and family-friendly atmosphere. With its rich history and modern amenities, Winter Garden offers the perfect blend of old-world charm and contemporary living. The scenic West Orange Trail, perfect for walking, biking, and jogging, winds through the area, providing residents with endless opportunities to enjoy the beautiful Florida weather.

One of the standout features of homes in this delightful region is the inclusion of dog run exterior features. For pet lovers, having a dedicated space for your furry friends to roam and play is a dream come true. These thoughtfully designed dog runs not only provide a safe environment for your pets but also enhance your outdoor living experience. Imagine watching your dog frolic in the sun while you relax on your patio, or hosting a weekend barbecue with friends while your canine companions enjoy their own space to play.

Winter Garden and Oakland are not just about beautiful homes; they offer a strong sense of community with various events, farmers' markets, and local festivals throughout the year. With top-rated schools, abundant recreational options, and a welcoming atmosphere, it’s no wonder that families and individuals alike are drawn to this enchanting area.

Whether you’re looking for a cozy bungalow or a spacious family home, Winter Garden and Oakland have something for everyone. Discover your dream home today, where both you and your four-legged friends can thrive in this idyllic Florida setting!

Newest Winter Garden/Oakland Homes with Dog Run Exterior Features

$1,020,000
3 Beds ⋅ 2 Baths ⋅ Lake Avalon Groves Rep SubDv. ⋅ 34787 Zip Code
Rare opportunity to own nearly 5 acres in the coveted Lake Avalon Rural Settlement—where horses, heritage oaks, and peaceful country living meet the convenience of Winter Garden. Escape the hustle and discover one of Winter Garden's last remaining rural neighborhoods. Set on 4.85 fully fenced acres, this picturesque property offers expansive green pastures, majestic oak and heritage trees, and the quiet, open spaces that have become increasingly difficult to find. Bring your horses, livestock, and four-legged companions. The property features a barn with tack room, two stalls with run-outs, multiple pasture areas, and plenty of room to enjoy the outdoor lifestyle Lake Avalon Rural is known for. A long driveway leads to a comfortable 3-bedroom, 2-bath home, perfectly positioned to take advantage of the property's natural beauty and peaceful surroundings. Located within the highly desirable Lake Avalon Rural Settlement, residents enjoy a unique blend of country charm and modern convenience. This close-knit community is known for its' equestrian lifestyle, small farms, wide-open spaces, and commitment to preserving the area agricultural heritage and country character. Despite its tranquil setting, you're only minutes from Historic Downtown Winter Garden, Fowler Grove, Hamlin Town Center, major highways, area attractions, shopping, dining, and top-rated schools. Whether you're dreaming of a horse property, hobby farm, or simply a private retreat beneath the shade of towering oaks, this exceptional property offers the space, freedom, and lifestyle you've been searching for. Experience the peace of country living without sacrificing the convenience of city amenities.

16104 Sandhill Road, Winter Garden
$575,000
4 Beds ⋅ 4 Baths ⋅ Waterleigh SubDv. ⋅ 34787 Zip Code
**SELLER MOTIVATED - NEW PRICE*** Welcome to this beautifully appointed, move-in-ready home located in the highly desirable, resort-style master-planned community of Waterleigh in Winter Garden. This home offers the perfect blend of modern sophistication and everyday functionality across a bright, open-concept design. From the moment you enter through the front door, the airy foyer welcomes you with elegant, durable ceramic tile in a natural wood-grain finish. This flooring flows seamlessly through the main living areas, which are accented by striking arched doorways and a beautifully crafted staircase. The heart of the home is the stylish chef's kitchen, which shines with pristine shaker-style cabinetry, expansive granite countertops, a classic tiled backsplash and a generous center island with an undermount double sink and an extended breakfast bar perfect for casual dining. Fully equipped with sleek stainless-steel appliances and a dedicated built-in beverage cooler station, this culinary space overlooks a main living zone flooded with natural Florida sunshine through large windows with custom blinds. The primary bedroom ensuite features dual vanity sinks, stone countertops and a massive walk-in closet. Upstairs, the second-floor balcony is the place to unwind after a long day or start your morning with sun salutations. A brick-paved backyard patio, double pane hurricane resistent windows and a rear-entry garage provide ultimate privacy and includes electric vehicle charger. Living in Waterleigh means enjoying a vacation-style lifestyle every day. With HOA-included lawn and ground maintenance, you have nothing left to do but relax and enjoy the community's premier amenities, including multiple resort-style pools, fitness centers and tennis and pickleball courts. Plus, you are just minutes from Disney's Magic Kingdom, upscale shopping at Winter Garden Village, historic downtown Winter Garden and Orlando International Airport.

9360 Mclaren Alley, Winter Garden
$340,000
3 Beds ⋅ 3 Baths ⋅ Tucker Oaks Ph 8 SubDv. ⋅ 34787 Zip Code
Beautifully maintained 3-bedroom, 2.5-bath townhome located in the gated Tucker Oaks community in Winter Garden. This home features an open-concept floor plan with abundant natural light, a functional layout, and an attached garage for added convenience. The kitchen offers ample cabinet and counter space and overlooks the living and dining areas. Upstairs, the primary suite includes a private bath and walk-in closet, while the additional bedrooms provide flexibility for guests, work-from-home space, or other uses. Recent updates include a new roof, dishwasher, and garbage disposal installed in August 2024, along with an HVAC system replaced in 2022. Community amenities include a pool, playground, basketball courts, scenic areas, and dog parks — including one conveniently located on the same cul-de-sac as the condo. Conveniently located near Downtown Winter Garden, Winter Garden Village, SR-429, Florida’s Turnpike, shopping, dining, hospitals, and area attractions. This property offers low-maintenance living with convenient access to major commuter routes and Central Florida destinations.

15625 Boggy Oak Circle Unit 108B, Winter Garden
$538,000
3 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 1b SubDv. ⋅ 34787 Zip Code
Welcome to the highly desirable Horizon West community of Waterleigh – Marina Bay, where lifestyle, convenience, and a true sense of community come together in one of Central Florida’s most sought-after neighborhoods. This beautifully upgraded south-facing Cordale model is move-in ready and thoughtfully designed, offering a perfect blend of style, comfort, and functionality for modern living. From the moment you arrive, you’ll appreciate the effortless curb appeal with HOA-included landscaping, allowing you to enjoy a pristine exterior year-round without the maintenance. Inside, the home immediately impresses with a clean, modern aesthetic and ZERO carpet throughout. Ceramic tile spans the main living areas, laundry room, and bathrooms, while matching hardboard vinyl plank flooring flows seamlessly through all bedrooms, the upstairs loft, and even the staircase, creating a cohesive and elevated look. Designed with both everyday living and entertaining in mind, the open-concept layout creates a warm and inviting atmosphere. The living room features a stunning modern accent wall that serves as a stylish focal point, while the primary suite offers its own beautifully designed accent wall, creating a private retreat with a touch of luxury. The kitchen is both functional and upgraded, complete with an enhanced stove and custom pantry shelving, while additional custom closet shelving throughout the home provides exceptional organization and storage. Step outside to your screened-in lanai and fully fenced backyard, perfect for relaxing evenings, entertaining guests, or creating a safe and enjoyable space for family and pets. Just outside your front door, a charming park offers a peaceful setting to unwind and even catch nightly fireworks from Walt Disney World, adding a little extra magic to your everyday life. Waterleigh offers an unmatched resort-style lifestyle, with amenities including a community pool, fitness center, scenic trails, clubhouse, dock, volleyball court, community garden, dog park, playground, and more. Residents also enjoy access to additional amenities throughout the greater Waterleigh community, along with a full calendar of events that bring neighbors together year-round. Location is everything, and this home delivers with quick access to FL-429, making commuting a breeze while keeping you close to top-rated dining, shopping, and everyday conveniences. Zoned for highly sought-after A-rated schools, this home is an exceptional opportunity for families looking to combine comfort, style, and community in one perfect place. This is more than just a home, it’s a lifestyle opportunity in one of Horizon West’s most vibrant communities. Don’t miss your chance to own this beautifully upgraded, move-in ready home in Waterleigh. Schedule your private tour today!

16197 Wind View Lane, Winter Garden
$347,500
3 Beds ⋅ 3 Baths ⋅ Tucker Oaks Bldg 5 SubDv. ⋅ 34787 Zip Code
Welcome to this spacious 3 bedroom 2.5 bath home situated on a quiet cul-de-sac with no rear neighbors and low HOA in the highly desirable Winter Garden area! This well maintained property features an open and functional floor plan with generous living spaces and abundant natural light, ideal for both everyday living and entertaining. The kitchen offers ample cabinet and counter space, flowing seamlessly into the main living areas. The primary suite provides a comfortable retreat with a private bath, while two additional bedrooms offer flexibility for family, guests, or a home office. Enjoy a private screened patio perfect for relaxing or hosting gatherings. Prime location, just minutes from everything Winter Garden has to offer! Conveniently located near shopping, dining, and entertainment with easy access to Highway 50 and the Florida Turnpike. Don’t miss this opportunity, schedule your private showing today!

15353 Oak Apple Court, Winter Garden
$625,000
4 Beds ⋅ 2 Baths ⋅ Island Pointe Sub SubDv. ⋅ 34787 Zip Code
Welcome to 1075 Chase Drive-located in downtown Winter Garden, just minutes from the charm and energy of Plant Street. This rare, newer-construction single-story home offers a blend of modern comfort and timeless style that’s sure to impress. As you enter, custom tile in the foyer sets the tone, with a versatile flex room to the right—perfect for a home office, formal dining room, playroom, or whatever suits your lifestyle.The open-concept design seamlessly connects the kitchen, dining, and family areas, creating an ideal space for entertaining. The large kitchen island is perfect for cooking, casual meals, or hosting friends and family. Sliding glass doors open to create an effortless indoor-outdoor living experience—perfect for those quintessential Florida days. The split floor plan offers privacy, with the primary suite serving as a true retreat, complete with high ceilings, a double vanity, and a spa-like shower. On the opposite side of the home, you’ll find three additional spacious bedrooms, each with plantation shutters and high end laminate flooring. After a long day, unwind on your fully screened back porch with space for multiple seating areas, or head to the side yard to tend your garden. The thoughtfully designed outdoor living space offers plenty of room for grilling, dining, and relaxing—an entertainer’s dream. Just minutes from your front door, Winter Garden’s vibrant Plant Street awaits, offering an award-winning farmer’s market, local dining, boutique shopping, art galleries, Crooked Can Brewery, the West Orange Trail, and year-round festivals.This is a rare opportunity to own a beautifully crafted home in one of Winter Garden’s most desirable neighborhoods—where modern living meets small-town charm. Call for your private showing today.

1075 Chase Drive, Winter Garden
$696,000
5 Beds ⋅ 5 Baths ⋅ Harvest At Ovation SubDv. ⋅ 34787 Zip Code
Amazing corner lot home with a detached private in-law suite, gourmet kitchen, and no rear neighbors, located in Horizon West Harvest at Ovation, just minutes from Walt Disney World and Flamingo Crossings, and Hamlin Town Center. Situated on one of the best corner homesites in the bungalow section of Harvest at Ovation, this 2024 Elevation B home offers privacy, wooded views, and natural light that interior lots simply do not have. With no rear neighbors and windows on multiple sides, the home feels open and well positioned from the moment you arrive. There is approximately 2,860 square feet under roof, including 2,393 square feet of main living space plus a fully permitted 530-square-foot in-law suite above the garage. The suite includes its own living area, kitchenette with wet bar, and full bath, making it ideal for extended family, long-term guests, or a private home office setup. The kitchen was built with the full gourmet option and is the only bungalow in the neighborhood configured this way. It includes three ovens, quartz countertops throughout, 42-inch cabinetry, soft-close drawers, stainless steel appliances, and a large walk-in pantry — designed for someone who actually cooks and entertains. Additional features include luxury vinyl plank flooring, a tray ceiling in the primary bedroom, wood stair treads, tile showers, quartz bath counters, recessed lighting, audio pre-wire, built-in garage storage, laundry room built-ins, zoned HVAC, and tankless water heaters. The first-floor block walls were upgraded with core-fill foam insulation, providing improved energy efficiency and a noticeably quieter interior. The fully paved lanai and corner placement create a more open and private outdoor setting than most homes in the community. Harvest at Ovation offers a pool, park, and playground, and the location places you minutes from Hamlin Town Center, top-rated schools, SR-429, Walt Disney World, and Flamingo Crossings. A rare opportunity to own one of the best-positioned and most thoughtfully upgraded bungalows in Harvest at Ovation.

16271 Honey Harvest Street, Winter Garden
$225,000
2 Beds ⋅ 2 Baths ⋅ The Grove Resort SubDv. ⋅ 34787 Zip Code
Welcome to The Grove Resort & Water Park in Winter Garden, FL. This fully furnished 2-bedroom, 2-bathroom condo-hotel unit offers an open floor plan designed for functionality and comfort. The kitchen features modern appliances, solid surface countertops, and ample cabinet space. The living and dining areas provide direct access to a private screened balcony. The primary suite includes an en-suite bathroom with a soaking tub, separate glass-enclosed shower, and dual vanities. The second bedroom is well-sized and located near a full bathroom, providing additional accommodation flexibility. The Grove Resort amenities include multiple pools, water park with slides and lazy river, surf simulator, fitness center, full-service spa, on-site dining, and 24-hour front desk service. The property participates in a rental program, offering short-term rental capability. Conveniently located near Walt Disney World and major Orlando attractions, with access to shopping, dining, and highways. Schedule a showing to learn more.

14501 Grove Resort Avenue Unit 1343, Winter Garden
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