$5,600,000Price reduced by $399,000 on Oct 9, 2026
800 W 2nd AvenueWindermere, FL, 34786
- 5 beds
- 5 baths
- 5,511 sqft
Windermere, Florida
Downtown Windermere Homes for Sale
Get to know Main Street, everyday facilities and the surrounding lakes as you consider a full-time or second home near Windermere's town center.
Windermere, Florida
Downtown Windermere brings Main Street, local gathering places and the surrounding lakes into focus for buyers looking for a full-time residence or second home. Town Square Park hosts the Friday farmers market, while the nearby Windermere Branch Library and town recreation facilities offer practical points of reference for everyday life. As you browse homes for sale, consider each property's location in relation to the town center, and check recreation access and lakefront features individually, rather than relying on a Windermere mailing address.
Listings for sale
19 listings
Downtown Windermere at a glance
- For sale now
- 19
- Median asking price
- $1,572,000
- Community area
- 2.4 sq mi
Browse by price
19 listings for sale
A Closer Look at the Town Center
Downtown Windermere centers on Main Street and the immediately surrounding residential streets in Windermere, Orange County, Florida. This is a more focused location than the broader area carrying a Windermere mailing address: the incorporated town and the postal area are not interchangeable. For buyers, that distinction helps put a home's setting into perspective. Start with its actual position relative to the town center, then consider how the library, Town Square Park and recreation facilities would fit your routine. Whether you want a full-time residence or a second home, the street location tells you more than the postal name alone.
Downtown Windermere Map and Location
Main Street provides the starting point for understanding downtown's geography. The town's official Future Land Use Map 2035 shows a Town Center Overlay District, with an inset covering the vicinity of 4th through 7th Avenues, Forest Street and Oakdale Street. Lake Butler lies west of the central street grid, Lake Down lies east, and Lake Bessie sits southeast of the center. Main Street connects north toward Maguire Road, while East 6th Avenue connects east toward Conroy Windermere Road. These streets and lakes are useful reference points when comparing property locations. Treat the planning map as an orientation guide, rather than a precise property locator or a fixed boundary for a downtown residential home search.
Everyday Places Along Main Street
These Main Street destinations help you compare a home's location with the community facilities you expect to use.
Town Square Park
At 520 Main Street, the park hosts the Friday farmers market, a recurring town-center activity to consider when picturing your routine.
Windermere Branch Library
At 530 Main Street, the library offers borrowing, public computers, Wi-Fi, printing and children's programming for everyday use.
Town Administration
Town administration is at 614 Main Street, separate from the park and library, a useful civic reference point for prospective residents.
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Community Life at the Friday Market
The Friday farmers market brings a recurring community activity to Town Square Park, giving prospective owners a concrete picture of life around Main Street. Normally held from 9 a.m. to 1:30 p.m., it features produce, seafood, bread, flowers and handmade goods. For full-time residents, it can become part of the week's food shopping; for second-home owners, it offers a way to spend a Friday morning in the town center. The published schedule includes closures when town offices are closed, so check the town's current event details before heading over. Consider how those daytime hours would fit your own routine.
Lakes, Tennis and Recreation Access
The surrounding lakes and town recreation facilities offer different ways to enjoy time outdoors, with access depending on the facility. Windermere maintains six secured, lighted tennis courts: three at Park Among the Lakes on Main Street and three at the recreation center on Park Avenue. Players need a resident tennis pass/key. For boating, Fernwood Park's Lake Butler ramp and the Lake Bessie ramp are resident-only, while Orange County provides a public Lake Down ramp along East 6th Avenue. When comparing homes, distinguish these shared facilities from property-specific features. A Windermere mailing address alone does not establish resident eligibility, and proximity to a lake does not mean a home includes waterfront, a dock or private boating rights.
Where Downtown Windermere is located
2.4 sq mi
Downtown Windermere Buyer Questions
Gaby Sadler
Property Specialist, Serhant
Talk to Gaby before you buy
I can arrange viewings, answer your questions and prepare a personalized rental projection for any home you're considering.
Find Your Place Near Downtown Windermere
As you explore Downtown Windermere homes for sale, consider how each property's actual location fits the life you want to build here. Main Street facilities, the Friday market and access to recreation may matter differently for a full-time home than for a second home. Use the town center as a reference point, then look closely at the home's street, its relationship to the lakes and the amenities available to you. Browse properties with those priorities in mind to shape your next steps.