Winter Oaks Homes with Block Exterior Construction

Welcome to Winter Oaks, a charming subdivision nestled in the heart of Winter Garden, Florida, where the warmth of community meets the beauty of suburban living. This picturesque neighborhood, located in Orange County, offers an inviting atmosphere that is perfect for families, retirees, and everyone in between.

Winter Oaks is renowned for its beautifully designed homes, many of which feature durable block exterior construction. This not only enhances the aesthetic appeal of the residences but also provides added security and energy efficiency. Homeowners can enjoy peace of mind knowing their investment is built to last, while also benefiting from lower energy costs thanks to the superior insulation properties of block construction.

As you stroll through the tree-lined streets of Winter Oaks, you’ll discover a vibrant community filled with friendly neighbors and a strong sense of togetherness. The subdivision is conveniently located near top-rated schools, lush parks, and a variety of shopping and dining options, making it an ideal place for families to thrive.

Outdoor enthusiasts will appreciate the nearby recreational opportunities, including scenic trails and beautiful lakes perfect for fishing or kayaking. Additionally, the charming downtown Winter Garden, with its historic feel and lively farmers market, is just a short drive away, offering a delightful mix of local shops and eateries.

Whether you’re looking for a peaceful retreat or an active lifestyle, Winter Oaks has something to offer everyone. Come and experience the charm of this wonderful community, where your dream home awaits!

Newest Winter Oaks Homes with Block Exterior Construction

$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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