Winter Oaks Homes with Two Story Property Description

Welcome to Winter Oaks, a charming subdivision nestled in the heart of Winter Garden, Florida. This vibrant community offers a perfect blend of suburban tranquility and modern convenience, making it an ideal place for families, professionals, and retirees alike. With its lush landscapes and friendly atmosphere, Winter Oaks is a hidden gem in Orange County.

The homes in Winter Oaks are predominantly two-story properties, designed to maximize both space and comfort. These thoughtfully crafted residences feature open floor plans, allowing for seamless flow between living areas, perfect for entertaining guests or enjoying quality family time. Spacious kitchens come equipped with modern appliances and ample storage, catering to the culinary enthusiast in your household.

Each two-story home boasts generously sized bedrooms, providing privacy and comfort for everyone. Many of these properties also include beautifully landscaped backyards, ideal for outdoor gatherings, gardening, or simply soaking up the Florida sunshine. The community is designed with families in mind, featuring nearby parks, playgrounds, and walking trails that encourage an active lifestyle.

Living in Winter Oaks means you’re just a stone’s throw away from Winter Garden’s charming downtown area, filled with quaint shops, delightful dining options, and vibrant community events. Plus, with easy access to major highways, you’re conveniently connected to Orlando’s attractions, making it easy to explore everything this beautiful region has to offer.

Discover the warmth and charm of Winter Oaks—where your dream home awaits!

Newest Winter Oaks Homes with Two Story Property Description

$680,000

4 Beds ⋅ 3 Baths ⋅ Winter Oaks SubDv. ⋅ 34787 Zip Code

Welcome to Winter Oaks, one of Winter Garden’s most desirable communities, just minutes from the charm, dining, shopping, and entertainment of historic Downtown Winter Garden. Tucked away at the end of a quiet cul-de-sac and situated on one of the community’s largest lots, this beautifully maintained 4-bedroom, 3-bath home offers an exceptional combination of space, character, and location. Step inside to an impressive 20-foot foyer that creates a dramatic first impression and opens to spacious living areas designed for both everyday comfort and entertaining. Thoughtful architectural details are found throughout the home, including 9'4" ceilings, hardwood flooring, Craftsman-style trim, tall baseboards, crown molding, wainscoting, oak stairs, custom built-ins, and detailed window trim. The inviting kitchen features 42-inch cabinetry, Quartz countertops, stainless steel appliances, generous prep and storage space, and a charming built-in banquette for casual dining. Sliding glass doors extend the living space to a screened patio overlooking the expansive backyard. A full laundry room with utility sink is conveniently located nearby. The first floor also features an elegant formal dining room accented with beautiful wainscoting, along with a bedroom that can easily serve as a private home office or guest suite and an adjacent full bathroom. Upstairs, the spacious Owner’s Suite provides a peaceful retreat with tray ceilings, crown molding, and a private balcony. The en-suite Fully Remodeled bathroom offers dual vanities, a beautiful super shower, and an impressive oversized walk-in closet. Two additional bedrooms and an upgraded full bathroom complete the second floor. Outside, enjoy the privacy and possibilities of the oversized fenced yard, offering plenty of room for outdoor entertaining, recreation, or creating your own backyard retreat. The home has been lovingly maintained and thoughtfully improved over the years, including a new roof in 2020, A/C Air Handler in 2023, energy efficient replacement windows throughout most of the home. With its generous homesite, cul-de-sac location, distinctive architectural details, and convenient access to Downtown Winter Garden by foot or bike, this home offers a wonderful opportunity to enjoy one of Central Florida’s most sought-after communities.

707 Chase Oaks Court, Winter Garden

$749,995

5 Beds ⋅ 3 Baths ⋅ Winter Oaks SubDv. ⋅ 34787 Zip Code

Reduced: Nestled in the sought-after golf cart district just minutes from Historic Downtown Winter Garden, this spacious 5-bedroom, 3-bath smart home in Winter Oaks offers the perfect blend of comfort, style, and convenience. A rear-entry garage enhances the home's exceptional curb appeal, while the thoughtfully designed floor plan is ideal for both everyday living and entertaining. The first floor features formal living and dining rooms, a bedroom that also makes an ideal home office, a full bath, a separate laundry room, and a beautifully appointed kitchen with 42-inch cabinetry, granite countertops, stainless steel appliances, and a sunny breakfast area. Upstairs, the private primary suite provides a peaceful retreat with tray ceilings, a private balcony, an oversized walk-in closet, dual vanities, a garden tub, and a separate walk-in shower. Three additional bedrooms complete the second floor. Step outside to enjoy the fenced backyard featuring an expansive screened outdoor living area and a private plunge pool/spa, creating your own backyard oasis. Additional highlights include a new roof, tankless water heater, 16-camera security system, landscape lighting, and optional furnishings, including a baby grand piano. Residents of Winter Oaks enjoy exceptional community amenities, including a resort-style pool, playground, scenic walking trail, tranquil ponds with fountains, and a charming entrance highlighted by a restored historic water tower. Just one mile from the award-winning Winter Garden Farmers Market, Plant Street's popular shops and restaurants, the West Orange Trail, and convenient SR-429 access, this home offers an exceptional opportunity to enjoy one of Central Florida's most desirable lifestyles.

644 Autumn Oaks Loop, Winter Garden

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