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.
Posted on Vanessa RichTrustindex verifies that the original source of the review is Google. Jared and his team did an amazing job helping us find our perfect home in our dream neighborhood near downtown Winter Garden. We were worried about buying a house remotely, however Jared was so easy to work with and guided us through the process smoothly. Also, a shoutout to Heidi for being amazing and showing us all the houses until we found the perfect one. I'm so glad we decided to choose Jared Jones Real Estate Team!Posted on K PearsonTrustindex verifies that the original source of the review is Google. Jared is the best, truly "value added" realtor we have had (with 8 homes purchased & 7 sold) the privilege of working with... He combined his regional knowledge, professional insights, and personal, servant-leadership to EVERY aspect of our relocation to Clermont. From offering early vision-trip help to the best of the best professional services support teams after the sale, Jared has truly blessed us in our relocation as a Christian professional. It's really refreshing to meet, work with, & befriend a guy who sets the standard for excellence in real estate, while simultaneously walking his talk as a God-honoring disciple of Christ. Thank you Jared!Posted on Tova BrodyTrustindex verifies that the original source of the review is Google. Jared was our realtor for our home search in the Orlando area (we chose Saint Cloud). If you are moving or buying or selling real estate in central Florida, call Jared Jones today! We just moved from out of state and we absolutely could not have gotten it done without Jared and his team. We were beyond impressed with his knowledge and he was there with us every step of the way making sure it all went well. I cannot imagine having made this move without Jared’s help and guidance. 1000% recommend. ⭐️⭐️⭐️⭐️Posted on Donna McDonaldTrustindex verifies that the original source of the review is Google. Jared was wonderful to work with! He really helped us with fulfilling our dreams to purchase a home in Florida, we will definitely work with him again!Posted on Xitong LiTrustindex verifies that the original source of the review is Google. From out of the state just bought a house by working with Jared and his team mostly remotely. It was a long complex process, and Jared and his team took care of every nuances and helped us bid the house with very favorable price. Jared's knowledge of Orlando neighborhoods, their histories and prospects is very deep and helpful.Posted on S BrodyTrustindex verifies that the original source of the review is Google. Jared helped my wife and I find the right home in Saint Cloud FL. Jared and his team are truly "one call does it all " highly recommend and encourage folks to let his knowledge and experience help you. Relocating can be difficult make it easier with the right real estate agent. Simon & T. BrodyPosted on w mTrustindex verifies that the original source of the review is Google. Wish I could have 10 stars. I found Jared on You tube. I know a bit about real estate investing. I also know about building a team. .Jared is real deal!! He is who he says he is. Understands the Orlando market, We Jared Jones on You tube. Watched for Months. He is on top of the Orlando market! Made my call to Jared on July 4th closed on a great deal Oct 31st after touring investment props for 2 weeks end of September. Our transactions happened within a month of getting under 10/31/25. Jared helping us find our investment property and we just closed as of today Halloween October 31 Thank you and so happy we made that one call back in July! Scott and DonnaPosted on David AinsworthTrustindex verifies that the original source of the review is Google. My wife and I relocated from the Northeast where we lived our entire lives, to the Orlando area. In my search of videos about florida on YouTube I came across Jared's many video's. My perception was that he was highly knowledgeable and highly engaged in the real estate industry. When I contacted him and we spoke for the first time he quickly turned perception to reality. As we worked through the process it just got better and better. Excellent advice, consistent communication and support over the months we went through the process. When we found a house he advocated for us to the highest level to be sure everything transacted in our best interest. The owners even left an item I was adamant I did not want left, he drove his truck over after we closed, carried it out and disposed of it for us! Ladies and gents with the utmost seriousness look no further this guy knows his business from top to bottom. One of if not the best decisions we made in this entire process was to work with Jared. This guy is an absolute rock star. Don't think twice about it, you found your man.Posted on ishtiaque ahmedTrustindex verifies that the original source of the review is Google. This guy is THE BEST !!!! Very helpful and a great guide… he just got us a great place within very short time. And we love it. A great negotiator and a great Realtor.I wish him all the best in life 👍🙌🫡Posted on Lot LamTrustindex verifies that the original source of the review is Google. I would recommended to anyone who wants to buy and sell investment homes or retirement homes in central Florida . Jared Jones the broker who I trusted the most .Last month , we spent 3 days in central searching for investment homes . A month late , we got our investment home in central Florida. He was very knowledgeable in dealing sellers agents. He was trying his best to get good deal for us . I was very please the ways he was working with seller agent. We got what we wanted. So thank you Jared for assisting us found a nice investment home . Lam,
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)




















