Downtown Winter Garden Homes for Sale
Explore Downtown Winter Garden homes for sale. Discover historic charm, modern living, top neighborhoods, attractions, and lifestyle in the heart of Winter Garden.
Find Your Dream Home in Downtown Winter Garden
The Downtown Winter Garden Area, often called the “original” Winter Garden, is where the community began. This section of town was once surrounded by citrus groves to the south—what is now the Winter Garden Village area and the rapidly expanding Horizon West.
Centered around the historic Plant Street corridor, Downtown Winter Garden is the town’s hub of activity. Here you’ll find Town Hall, cultural venues, dining, shopping, and many of the events that make Winter Garden one of Central Florida’s most vibrant communities.
Housing in this area ranges from historic homes built in the early 1900s to newly constructed properties with modern features. While single-family homes are most common, you’ll also find townhomes sprinkled throughout the area.
Where is the Downtown Area in Winter Garden?
The Downtown/Original Winter Garden area is located in the northern section of the city. It’s:
• North of the Florida Turnpike
• West of the 429 Expressway
• East of the Oakland area
• South of Lake Apopka
This section includes much of what was historically Winter Garden before new developments expanded southward toward Disney after the 429 opened.
Hwy 50 runs east-west through the southern edge of the area, while Plant Street (State Road 438) cuts diagonally through the heart of downtown. The popular West Orange Trail also winds through many of the neighborhoods here, connecting residents directly to downtown.
No Results Found.
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 Rh ITrustindex verifies that the original source of the review is Google. Heidi and Jared are amazing realtors. I would recommend them to anyone looking.Posted on Google Birgit HTrustindex verifies that the original source of the review is Google. Heidi was awesome! She always took the time to answer all my questions and went above and beyond to help us. We were a little more complicated because we moved from Alaska to Florida and she helped navigate the whole process and made it so much smoother.Posted on Google Davi PTrustindex verifies that the original source of the review is Google. Stephany Cornelius our realtor is AMAZING. We initially reached out to Jared Jones who is amazing as well by the way super professional, and he connected us with Stephany. She is such a star. She treated me and my family (kids) with so much love, care and professionalism that I am thoroughly impressed with her. She was there with us and for us every step of the way. She became family. We love her so much and we will deeply recommend using them for finding a 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 Roxanne GTrustindex verifies that the original source of the review is Google. My husband discovered Jared on social media while we were looking for homes in Florida. He reached out when we were ready to get serious and we are so thankful we did! He made finding our home and all that goes with buying and relocating so much smoother. He hooked us up with a great lender (Cross Country Mortgage) and anything else we needed. Highly recommend Jared Jones!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 transactionsVerified 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
Winter Garden Areas
Downtown Winter Garden Area Neighborhoods
Winter Garden Village Area Neighborhoods
Estates Lakeview Preserve
Horizon West Area Neighborhoods
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
Oakland Area Neighborhoods
Johns Landing
Lake Apopka Sound (NEW)