Winter Oaks Homes for Sale

Welcome to Winter Oaks, a charming subdivision nestled in the heart of Winter Garden, Florida, within Orange County. This picturesque community perfectly combines suburban tranquility with the vibrancy of city life, making it an ideal place for families, professionals, and retirees alike.

Winter Oaks is characterized by its beautifully landscaped streets, lined with stunning homes that boast a variety of architectural styles. From modern designs to classic Florida charm, there's a home for every taste and preference. The community is known for its spacious lots and well-maintained properties, offering residents ample outdoor space to enjoy the sunny Florida weather.

One of the standout features of Winter Oaks is its proximity to some of the best amenities Winter Garden has to offer. Residents can take advantage of nearby parks, recreational facilities, and shopping centers, ensuring that everything you need is just a short drive away. The vibrant historic downtown area is also nearby, where you can explore delightful boutiques, enjoy dining at local eateries, and partake in various seasonal events that foster a strong sense of community.

For those interested in homes for sale in Winter Oaks, you’ll find an array of options that cater to diverse lifestyles and budgets. Whether you're looking for a cozy starter home or a spacious family residence, the real estate market in Winter Oaks is thriving. With its friendly atmosphere and convenient location, Winter Oaks is not just a place to live; it’s a place to call home. Discover the magic of Winter Oaks today and see why so many are choosing to make this community their own!

Newest Winter Oaks Homes for Sale

$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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