Browse Deer Island Homes for Sale in Winter Garden, FL. Discover community amenities, nearby attractions, schools, and the lifestyle this neighborhood offers.
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Browse Deer Island Homes for Sale in Winter Garden, FL. Discover community amenities, nearby attractions, schools, and the lifestyle this neighborhood offers.
Deer Island is an exclusive gated community of custom single-family homes located off Hwy 50 (Colonial Drive) just south of the Florida Turnpike in the Northwest section of Winter Garden. Homes in Deer Island were built between 1988 and 2010 by various custom home builders, resulting in a diverse mix of architectural styles and expansive estate properties.
The community is especially known for its lakefront lifestyle, with many homes offering direct access to Johns Lake. The nearby West Orange Trail and easy access to Hwy 50 make Deer Island ideal for both recreation and commuting east toward Orlando or west toward Clermont.
Deer Island has a mandatory HOA that includes:
• Community boat ramp
• Fishing
• Golf carts allowed
• Sidewalks
• Water access
• Waterfront common areas
• Basketball court
• Tennis courts
• Security
Zip Code: 34787
Area: Western Oakland area of Winter Garden
North: Hwy 50 / Colonial Drive
South: Johns Lake & vacant land
East: Johns Lake & wetland areas
West: Johns Lake & the Clermont community
Grocery & Restaurants: West Point Commons
Mall: Winter Garden Village
Hospital: AdventHealth Winter Garden
Schools: Orange County Find My School
Attractions: Walt Disney World & Universal Studios
Get Out & Play: West Orange Trail
Local Hangout: Downtown Winter Garden
Closest Beach: Cocoa Beach
Home features in Deer Island are common but may vary from property to property:
Builders: Various custom home builders
Architectural Styles: Custom, Victorian, Contemporary, Patio, Spanish/Mediterranean, Key West
Bedrooms: 3–7
Garage Spaces: 1–4
Living Area: Approx. 2,300–12,000 sq ft
Interior Rooms: Bonus room, breakfast room (separate), den/library/office, family room, Florida room, formal dining room, formal living room, inside utility, interior in-law apartment, storage rooms
Average Lot Size: 1–2 acres
Construction: Shingle and tile
Roof: Shingle and tile
Exterior Features: Fenced yards, irrigation system, lighting, outdoor grill, outdoor kitchen, rain gutters, sidewalks, sliding doors
Views: Some homes offer private pools, trees/woods, or Johns Lake water views
Call or text the Jared Jones Real Estate Team at 407-706-5000 to learn more today!
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Steven MTrustindex verifies that the original source of the review is Google.
⭐⭐⭐⭐⭐ When we found out we were moving across the country to the Orlando area, we started watching Jared Jones’ Orlando housing market videos on YouTube. His videos provided a ton of great information about the different communities, neighborhoods, and the Orlando housing market and really helped us get familiar with the area before making the move. As good as Jared’s videos are, his team is even better in person! We had the pleasure of working with Leonard O’Connor, and he was awesome from the very beginning. Communication was excellent throughout the entire process. Leonard took the time to show us several existing homes and really helped us narrow down exactly what we were looking for. Once we zeroed in on the right property, Leonard was there every step of the way. He helped us through the negotiations and, because we were still living across the country, went above and beyond to help with measurements and other things we needed taken care of before we could arrive in Orlando. Having someone local we could trust made a huge difference and took a lot of stress out of buying a home from thousands of miles away. The entire process went incredibly smoothly, and closing was a breeze. We couldn’t be happier with our experience. If you’re moving to the Orlando area—especially if you’re relocating from out of state—I highly recommend Jared Jones, Leonard O’Connor, and the eXp Realty team. Great communication, great service, and people who genuinely work hard for their clients. Five stars all the way!Posted on Google![]()
Peter MTrustindex verifies that the original source of the review is Google.
Jared and his team helped me and my family in purchasing a home in Orlando and I would highly recommend them to anyone. They are extremely knowledgeable about the greater Orlando area which was important to me moving from New Jersey. They kept us informed every step of the way and did a phenomenal job when it came time to present an offer and close the deal. This team is top notch!Posted on Google![]()
Dyan DTrustindex verifies that the original source of the review is Google.
Leonard O’Connor, with Jared Jones Realty team, did a fantastic job helping us find our new home in Clermont, Florida. He was very accommodating, often squeezing last minute home viewing into his schedule and doing virtual walkthroughs with us from Michigan. His communication throughout the process was exemplary and his vast experience shown through in his advice and negotiating skills. Leonard and the whole team at Jared Jones Realty worked together seamlessly to assist us every step of the way through the home buying process. We couldn’t be happier!Posted on Google![]()
Dan HTrustindex verifies that the original source of the review is Google.
Heidi was incredibly helpful and kind during the entire process. She negotiated effectively for us and was always reachable whenever we had a question and now we live in our dream home!Posted on Google![]()
Paul HTrustindex verifies that the original source of the review is Google.
Selling a home from overseas could have been stressful, but Jared and his team made the whole process feel incredibly straightforward. From the very beginning we felt we were in safe hands. Jared was always approachable, responsive and happy to answer any questions we had. His communication was excellent throughout, keeping us updated every step of the way, and his advice was always honest and reassuring. The professional photography and video marketing were first class and really showed our Davenport home at its very best. What impressed us most was how much Jared genuinely cared about achieving the best possible outcome for us. Even when unexpected issues arose during the sale, he remained calm, proactive and worked hard to keep everything moving towards a successful closing. We couldn’t have asked for a better Realtor and would wholeheartedly recommend Jared Jones and his team to anyone buying or selling a home in the Davenport and Central Florida area. Thank you, Jared, for all your hard work, professionalism and support—it has been a pleasure working with you.Posted on Google![]()
David RTrustindex verifies that the original source of the review is Google.
My wife and I purchased a home in Kissimmee, Florida and it was by far the best home buying experience we have ever had. This is our 7th home we have purchased. Stephany Cornelius was our Realtor from Jared Jones Real Estate Team and we couldn't have been more pleased. She made the process so easy, less stressful and guided us through every aspect including a very quick closing. I highly recommend Stephany if you're trying to navigate the home buying experience here in Florida.Posted on Google![]()
Gianfranco RTrustindex verifies that the original source of the review is Google.
Jared Jones was amazing at helping us pick and getting our dream home. He was very patient and always had an answer to any questions we had. Could not be more thankful for him and his team.Posted on Google![]()
David WTrustindex verifies that the original source of the review is Google.
Jared and his team were great to work with. Always professional and responsive to every situation that arose. Would love to work with them again on future deals.Posted on Google![]()
City TTrustindex verifies that the original source of the review is Google.
Jared and Kristen were a pleasure to deal with. Their professionalism and quick responses made the entire closing process smooth and stress-free. I look forward to working with them again on future transactionsPosted on Google![]()
Veronica RTrustindex verifies that the original source of the review is Google.
Jared was great! We were moving to FL from out of state and he made everything so much easier!Verified by TrustindexTrustindex verified badge is the Universal Symbol of Trust. Only the greatest companies can get the verified badge who has a review score above 4.5, based on customer reviews over the past 12 months. Read more
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