Welcome to a rare opportunity in the heart of Windermere! Located at 116 Main Street, this property represents one of the most coveted locations in Central Florida's premier community. Situated on Main Street, this lot offers the perfect canvas for your dream home in a location that simply cannot be replicated. While the existing structure requires extensive updating, the true value lies in this premium . 38 acre lot. This property sits in the center of historic Windermere, mere steps from the town's charming downtown area, local parks, and the Butler Chain of Lakes. The location offers the perfect blend of small-town charm and luxury living that Windermere is famous for. This an ideal opportunity for buyers looking to build their custom dream home in one of Central Florida's most prestigious addresses. The property's proximity to top-rated Windermere schools, upscale dining and shopping, and easy access to Orlando's attractions adds significant value to this already exceptional location. Just minutes from Restaurant Row, Disney World, and the affluent Isleworth and Bay Hill communities. Whether you're envisioning a modern masterpiece or a traditional estate, this rare Main Street lot provides the perfect foundation for your vision. Properties of this caliber in Windermere's historic downtown rarely become available. Don't miss this opportunity to be a part of Windermere.
Single-familyProperty Type
1958Year Built
0.38 acresLot Size
$575Est. Price/Sq.Ft.
3 car garageParking
Listed by Adam Judd• METROPOLIS R.E. SOLUTIONS, LLC
Welcome to a rare opportunity in the heart of Windermere! Located at 116 Main Street, this property represents one of the most coveted locations in Central Florida's premier community. Situated on Main Street, this lot offers the perfect canvas for your dream home in a location that simply cannot be replicated. While the existing structure requires extensive updating, the true value lies in this premium . 38 acre lot. This property sits in the center of historic Windermere, mere steps from the town's charming downtown area, local parks, and the Butler Chain of Lakes. The location offers the perfect blend of small-town charm and luxury living that Windermere is famous for. This an ideal opportunity for buyers looking to build their custom dream home in one of Central Florida's most prestigious addresses. The property's proximity to top-rated Windermere schools, upscale dining and shopping, and easy access to Orlando's attractions adds significant value to this already exceptional location. Just minutes from Restaurant Row, Disney World, and the affluent Isleworth and Bay Hill communities. Whether you're envisioning a modern masterpiece or a traditional estate, this rare Main Street lot provides the perfect foundation for your vision. Properties of this caliber in Windermere's historic downtown rarely become available. Don't miss this opportunity to be a part of Windermere.
Stellar MLS as Distributed by MLS Grid #O6267443
Jun 13, 2025
Sold
$695,000
$548/sq ft
Apr 2, 2025
Pending
—
Feb 21, 2025
Relisted
—
Feb 20, 2025
Pending
—
Feb 12, 2025
Relisted
—
Dec 30, 2024
Listed
$695,000
$548/sq ft
Year
Property tax
Land + Additions
Assessment*
2025
$7,599 (+10.4%)
$320,000 + $108,570
$428,570
2024
$6,885 (+6.5%)
$320,000 + $108,570
$428,570
2023
$6,466 (+19.2%)
$320,000 + $103,461
$423,461
2022
$5,424 (+3.8%)
$220,100 + $79,461
$299,561
2021
$5,226 (+10.5%)
$220,100 + $79,461
$299,561
2020
$4,730 (−5.3%)
$220,100 + $63,335
$283,435
2019
$4,996 (+4.0%)
$200,100 + $63,335
$263,435
2018
$4,806 (+1.1%)
$200,100 + $63,335
$263,435
2017
$4,756 (+4.1%)
$175,100 + $77,051
$252,151
2016
$4,569 (+7.2%)
$175,100 + $77,051
$252,151
2015
$4,262 (+11.7%)
2014
$3,816 (+9.6%)
2013
$3,483 (−5.4%)
2012
$3,680
Tax history for 116 Main St
Year
Property tax
Land + Additions
Assessment*
2025
$7,599 (+10.4%)
$320,000 + $108,570
$428,570
2024
$6,885 (+6.5%)
$320,000 + $108,570
$428,570
2023
$6,466 (+19.2%)
$320,000 + $103,461
$423,461
2022
$5,424 (+3.8%)
$220,100 + $79,461
$299,561
2021
$5,226 (+10.5%)
$220,100 + $79,461
$299,561
2020
$4,730 (−5.3%)
$220,100 + $63,335
$283,435
2019
$4,996 (+4.0%)
$200,100 + $63,335
$263,435
2018
$4,806 (+1.1%)
$200,100 + $63,335
$263,435
2017
$4,756 (+4.1%)
$175,100 + $77,051
$252,151
2016
$4,569 (+7.2%)
$175,100 + $77,051
$252,151
2015
$4,262 (+11.7%)
2014
$3,816 (+9.6%)
2013
$3,483 (−5.4%)
2012
$3,680
*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.
Public record
Beds
3
Baths
2
Stories
2
Lot width
—
Lot depth
—
Lot size
0.38 Acres
Year renovated
1958
Sq. Ft.
2,236
Year built
1958
Style
Single Family Residential
County
Orange County
APN
282317933604340
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Aug 17, 2026.
Property details
Parking
Parking Information
Garage Spaces: 3
Has Attached Garage
Has Garage
Interior
Bedroom Information
# of Bedrooms: 3
Bathroom Information
# of Full Baths (Total): 2
Laundry Room Information
Laundry Features: Other
Other Rooms Information
Additional Rooms: Interior In-Law Suite w/Private Entry