Winter Oaks Real Estate

Winter Oaks Real Estate

Welcome to Winter Oaks, a picturesque subdivision nestled in the heart of Winter Garden, Florida, where the charm of small-town living meets modern convenience. This vibrant community is located in Orange County, just a stone's throw away from the bustling attractions of Orlando, making it an ideal spot for families, retirees, and anyone looking to embrace the Florida lifestyle.

Winter Oaks is characterized by its beautifully designed homes, each showcasing unique architectural styles that blend seamlessly with the lush, tropical landscape. The tree-lined streets create a serene atmosphere, perfect for afternoon strolls or evening bike rides. Residents enjoy spacious yards and well-maintained common areas, fostering a sense of community and pride among neighbors.

One of the standout features of Winter Oaks is its proximity to a variety of amenities. Just minutes away, you’ll find an array of shopping options, from quaint boutiques to major retail centers. The area is also home to top-rated schools, parks, and recreational facilities, ensuring that families have everything they need right at their fingertips. For those who love the outdoors, the nearby West Orange Trail offers miles of scenic pathways for walking, jogging, and biking.

In addition to its fantastic location, Winter Oaks boasts a warm and welcoming community spirit. Residents often come together for neighborhood events, fostering friendships and creating lasting memories. Whether you’re looking to settle down or find a vacation home, Winter Oaks is a hidden gem that promises a fulfilling and vibrant lifestyle in the heart of Florida. Come discover your dream home in Winter Oaks today!

Newest Listings in Winter Oaks

$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
Start Your Search