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Windward Square Townhomes Winter Park FL

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Windward Square Townhomes Winter Park FL

Windward Square Winter Park FL

Windward Square townhomes for sale are normally available. Windward Square in Winter Park FL has approximately 325 townhomes in the community. Normally over 20 townhomes will sell here each year.

Click Below to See Homes For Sale In This City

Townhomes For Sale In Winter Park FL

Windward Square is located near the Villas of Casselberry. There are a few similar neighborhoods here and a couple of them are gated. Windward Square is a gated community and also has some amenities. There are 2 community pools, tennis courts and a children's play area near the center of the community.

Shopping is all around the area. Since the homes for sale here are practically on the corner of Howell Branch Road and Semoran Blvd which are both great local roads. If you leave Windward Square out of the northern side onto Howell Branch Road then there is a Publix Super Market, LA Fitness and much more practically right outside of the entrance.

The community was built between 1975 and 1980. You will see townhomes, condos and traditional single family homes advertised for sale here. The smallest home in the community is a 854 square foot 2 bedroom and 1 bath home. The largest home for sale you may see here is a 1,969 square foot 3 bedroom and 2 bath home. Best of all this is one of the most affordable places to live in the area and it just happens to be in a great location.

Moving Forward

Before viewing homes for sale in Windward Square it is always best to get pre-approved for your loan unless paying cash. We can assist with that and we also provide the best payment estimator online. Your on the right track and we are excited about assisting you. Normally this page will have homes for sale in Windward Square shown below. 




All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independent verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. The source of the listing data is as follows: Stellar MLS (updated 8/23/26 6:20 PM) |

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Wendy Morris LLC

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BK 3146762
16797 Broadwater Avenue
Winter Garden, Florida 34787

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