Winter Garden Shores First Add Homes for Sale

Welcome to Winter Garden Shores First Add, a hidden gem nestled in the heart of Winter Garden, Florida. This charming subdivision is more than just a community; it's a lifestyle choice for those seeking a perfect blend of suburban tranquility and urban convenience. With its picturesque tree-lined streets and friendly atmosphere, Winter Garden Shores First Add is ideal for families, retirees, and everyone in between.

Located in Orange County, this vibrant neighborhood is just minutes away from the bustling downtown Winter Garden, where you can enjoy a variety of shops, restaurants, and entertainment options. The nearby West Orange Trail offers endless opportunities for outdoor enthusiasts, providing a scenic route for walking, jogging, or biking. Plus, with easy access to major highways, commuting to Orlando and other surrounding areas is a breeze.

Homes for sale in Winter Garden Shores First Add showcase a delightful mix of architectural styles, from charming single-family homes to modern designs, catering to diverse tastes and preferences. Many properties feature spacious yards, perfect for family gatherings or quiet evenings under the stars. Inside, you'll find well-appointed interiors with open floor plans, updated kitchens, and cozy living spaces that make for comfortable living.

Whether you're a first-time homebuyer or looking to downsize, Winter Garden Shores First Add offers a welcoming community and a range of options to suit your needs. Don’t miss the opportunity to discover your dream home in this enchanting neighborhood. Explore our listings today and experience the charm of Winter Garden Shores First Add!

Newest Winter Garden Shores First Add Homes for Sale

$1,080,000

4 Beds ⋅ 3 Baths ⋅ Winter Garden Shores First Add SubDv. ⋅ 34787 Zip Code

Appraisal in hand! Welcome to one of Winter Garden's most remarkable custom transformations. This wasn't a flip—it was the owner's forever dream home. Originally built in 1959 and completely reimagined in 2023 and 2026. This extraordinary residence has undergone an extensive renovation and expansion, creating a truly one-of-a-kind property just minutes from Historic Downtown Winter Garden and Plant Street. Offering 2,729 square feet of beautifully designed living space, this 4-bedroom, 3-bathroom home showcases exceptional craftsmanship, thoughtful design, and luxury finishes throughout. In 2026, the owners completed a stunning expansion that includes an ultra-luxury primary suite designed as a private retreat. The spa-inspired custom bathroom features premium finishes, a private sauna, and a level of comfort rarely found at this price point. The heart of the home features open-concept living spaces filled with natural light, designer finishes, and seamless flow for everyday living and entertaining. Step outside to your private backyard oasis featuring a brand-new custom pool completed in 2026, creating the perfect setting for relaxing weekends and unforgettable gatherings. Major improvements include a 2026 HVAC system, 2026 luxury primary suite addition, 2026 custom pool, 2022 plumbing, 2022 electrical, 2018 roof, and all new windows installed in 2018, providing peace of mind for years to come. Every inch of this home tells the story of a family who spared no expense creating their dream home. Now, that dream can become yours. Schedule your private showing today!!!

20 E Division Street, Winter Garden

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