Browse Windward Cay Homes for Sale in Winter Garden, FL. Discover community amenities, nearby attractions, schools, and the lifestyle this neighborhood offers.
Home » Windward Cay Homes for Sale
Browse Windward Cay Homes for Sale in Winter Garden, FL. Discover community amenities, nearby attractions, schools, and the lifestyle this neighborhood offers.
Windward Cay is a gated community of single-family homes located off Tilden Road, just west of Winter Garden Vineland Road, in the Central North area of Winter Garden. Built primarily between 2003 and 2004 by Engle Homes of Orlando, this neighborhood is known for its spacious floor plans, three-car garages, and quiet setting surrounded by conservation areas.
Residents enjoy close proximity to the West Orange Country Club and convenient access to the 429 Expressway, providing an easy commute to Walt Disney World, I-4, the Florida Turnpike, and Northwest Orlando in Lake County.
Windward Cay features a mandatory HOA that maintains:
• Sidewalks
• Gated community setting
Windward Cay is located in the 34787 zip code within the Central Winter Garden Village area.
Neighborhood Borders:
North: Wintermere Pointe
South: Conservation land
East: Sunset Lakes
West: Conservation land
Grocery & Dining: Cornerstone at Summerport
Shopping: Winter Garden Village
Hospital: AdventHealth Winter Garden
Schools: Orange County Find My School
Attractions: Walt Disney World & Universal Studios
Outdoor Recreation: West Orange Trail
Local Hangout: Downtown Winter Garden
Closest Beach: Cocoa Beach
Home features commonly found in Windward Cay (may vary by property):
Builder: Engle Homes of Orlando
Architectural Styles: Contemporary & Florida
Bedrooms: 4–6
Garage: 3-car
Living Area: Approx. 2,400–3,900 sq. ft.
Interior Rooms:
Separate breakfast room
Den / home office
Family room
Formal dining room
Formal living room
Inside utility
Average Lot Size: Quarter acre
Construction: Shingle
Roof: Shingle
Exterior Features:
Fenced yards
Irrigation system
Lighting
Rain gutters
Sidewalks
Sliding doors
Sprinkler metered
Select homes with garden or wooded views
Call or text the Jared Jones Real Estate Team at 407-706-5000 to learn more today!
Posted on Google![]()
Stephanie STrustindex verifies that the original source of the review is Google.
The team possesses extensive knowledge of the Orlando real estate market, which proved invaluable in helping us select the ideal home. I highly recommend their services to anyone seeking professional assistance.Posted on Google![]()
Gurj DTrustindex verifies that the original source of the review is Google.
We had such a great experience working with Connor and would absolutely recommend him. As we were buying a house in Florida while still living in Utah, we relied on Connor for so much throughout the process. He was always incredibly responsive and went out of his way to make things easier for us. When we couldn’t view houses ourselves, he would visit them and send us detailed video walkthroughs, which was a huge help when trying to make decisions from another state. He handled communication with the agents, put together our offers, arranged the inspection and, once we had the inspection results, gave us great advice on how to negotiate so we could get the best possible deal. What really stood out was how willing he was to help with things that went beyond simply buying the house. Because we were in Utah, Connor offered to go back to the property whenever something needed checking, helped arrange appointments such as getting an electrician out, and even offered to continue checking on the house and things like the lawn for us after closing until we’re able to be there. Throughout the whole process Connor was friendly, attentive, patient and extremely easy to work with. Buying a house from across the country could have been incredibly stressful, but having someone local who was so responsive and willing to help made the whole experience much easier. Thank you for everything, Connor! We couldn’t be happier with our new home and really appreciate everything you did for us.Posted on Google![]()
Jonathan TTrustindex verifies that the original source of the review is Google.
Jared Jones went above and beyond in every aspect of our home-buying experience. From the very beginning to closing, Jared was there for us every step of the way. Buying a new home can be overwhelming, with countless details, questions, decisions, and unexpected bumps along the road, but Jared made the entire process feel manageable because we always knew he had our back. What really stood out to us was how involved and proactive he was. He didn't just show up for the big moments — he was there throughout the entire process, staying on top of details, answering our questions, advocating for us, and making sure we understood what was happening. Whenever something came up, Jared was quick to jump in and help find a solution. We genuinely felt like he was looking out for our best interests from start to finish. He was incredibly responsive, knowledgeable, patient, and professional, but what we appreciated most was that he truly cared. We never felt like we were just another transaction or another set of clients. Jared treated the purchase of our home as if it were his own, and that made a huge difference. We honestly cannot say enough good things about Jared. He exceeded our expectations in every way and made what could have been a stressful experience so much easier. If you're looking for a realtor who will truly go to bat for you, be there when you need him, and genuinely care about getting you into the right home, we couldn't recommend Jared more highly. Five stars doesn't really feel like enough. Thank you, Jared, for everything you did for us!Posted on Google![]()
Geoffrey ZTrustindex verifies that the original source of the review is Google.
Jared Jones is an absolute main stay in the Orlando Real Estate world. I've now had the pleasure of working with him in Orlando as well as Las Vegas years ago, and while he shifted coasts, his skills, care, and diligence in this business have remained sharp and calculated. Jared knows his stuff. I would question whether anyone knew Orland Real Estate better than Jared and his team. Whether I'm working with him directly, or one of his hand picked, expertly trained team members, I know I'm getting the same level of sill and dedication to meet our very demanding needs. Thank you Jared, and your team, for being our absolute Go-To in Orlando Real Estate!Posted on Google![]()
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.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
Estates Lakeview Preserve
Cove At Hamlin
Del Webb Oasis (NEW)
Harvest at Ovation
Mezzano
Osprey Ranch
Westhaven Ovation
Hamlin Pointe
Hamlin Ridge
Horizon Isle
Lake Star at Ovation
Northlake at Ovation
Parkview at Hamlin
Serenade at Ovation
Silverleaf Oaks
Silverleaf Reserve
Tribute at Ovation
Johns Landing
Lake Apopka Sound (NEW)