Winter Garden Shores First Add Real Estate

Welcome to Winter Garden Shores First Add, a charming subdivision nestled in the heart of Winter Garden, Florida. This delightful community is situated within Orange County, just a stone’s throw away from the picturesque downtown area, where historic charm meets modern convenience.

Winter Garden Shores First Add is characterized by its tranquil atmosphere, lush landscapes, and friendly neighbors. The subdivision features a variety of well-maintained homes, each with its unique character and style, making it an appealing choice for families, retirees, and anyone seeking a serene lifestyle. The community is known for its spacious lots, allowing for ample outdoor space for gardening, play, or simply enjoying the Florida sunshine.

One of the highlights of living in Winter Garden Shores is the proximity to a wealth of recreational activities. Residents can enjoy nearby parks, scenic walking trails, and the stunning West Orange Trail, perfect for biking or jogging. The vibrant downtown Winter Garden offers a plethora of dining options, boutique shopping, and local farmers markets, ensuring that you have everything you need right at your fingertips.

For those who appreciate the arts, the area boasts cultural attractions such as the Garden Theatre and various community events throughout the year. Additionally, with easy access to major highways, commuting to Orlando and other surrounding areas is a breeze.

If you’re looking for a community that combines the beauty of nature with the convenience of urban living, Winter Garden Shores First Add is the perfect place to call home. Come discover the charm of this inviting subdivision and experience the best of Winter Garden living!

Newest Listings in Winter Garden Shores First Add

$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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