David Shippey
863.521.4517

Windermere Town Real Estate

Market Snapshot of Listings in Windermere Town - Windermere, FL 34786
The current prices for all Real Estate Listings in Windermere Town - Windermere, FL are reflected in the the table below.
Averages based on current search criteria as of 07/30/2025 3:08 AM
Class Total Number Price Beds Baths Age
Residential7$2,094,5714.64.126.3
Rental2$6,6004.53.584.5
Displaying results 1-9 of 9
86 Photos 225 Magnolia Street Windermere, FL 34786

225 Magnolia Street
Windermere, FL 34786
Windermere Town
Residential

MLS# O6292745 / Active
7 Beds, 11.00 Total Baths, 10 Full Bath, 1 Half Bath, 5935 Sqft
Area: 34786 - Windermere, Subdivision: Windermere Town

LAKEFRONT GRANDEUR IN WINDERMERE | A MASTERPIECE ON LAKE DOWNUnveiling a rare opportunity to own an architectural masterpiece on the famed Butler C... 

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$4,899,000
Provided courtesy of COMPASS FLORIDA LLC
55 Photos 409 W 2nd Avenue Windermere, FL 34786

409 W 2nd Avenue
Windermere, FL 34786
Windermere Town
Residential

MLS# O6290296 / Active
5 Beds, 5.00 Total Baths, 4 Full Bath, 1 Half Bath, 4688 Sqft
Area: 34786 - Windermere, Subdivision: Windermere Town

Surrounded by glistening lakes and shaded by towering oaks, Windermere offers an unbeatable blend of natural beauty and small-town charm. Friendly ... 

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$2,499,000
Reduced -$100,000
Provided courtesy of UPSIDE REAL ESTATE INC
13 Photos 1020 Oakdale Street Windermere, FL 34786

1020 Oakdale Street
Windermere, FL 34786
Windermere Town
Residential

MLS# O6322270 / Active
5 Beds, 5.00 Total Baths, 4 Full Bath, 1 Half Bath, 3994 Sqft
Area: 34786 - Windermere, Subdivision: Windermere Town

Under Construction. Extraordinary new construction estate by renowned builder Davila Homes, nestled in the heart of Downtown Windermere. Meticulous... 

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$2,200,000
Provided courtesy of COMPASS FLORIDA LLC
54 Photos 830 Oakdale Street Windermere, FL 34786

830 Oakdale Street
Windermere, FL 34786
Windermere Town
Residential

MLS# O6250631 / Active
4 Beds, 5.00 Total Baths, 4 Full Bath, 1 Half Bath, 3670 Sqft
Area: 34786 - Windermere, Subdivision: Windermere Town

RARE FIND IN DOWNTOWN WINDERMERE!! This immaculate home defines where luxury meets contemporary, nestled in the heart of downtown Windermere. Pull ... 

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$1,875,000
Reduced -$20,000
Provided courtesy of CORCORAN PREMIER REALTY
64 Photos 109 E 12th Avenue Windermere, FL 34786

109 E 12th Avenue
Windermere, FL 34786
Windermere Town
Residential

MLS# O6326261 / Active
4 Beds, 4.00 Total Baths, 3 Full Bath, 1 Half Bath, 2791 Sqft
Area: 34786 - Windermere, Subdivision: Windermere Town

Modern upgrades meet timeless Windermere charm in this fully reimagined four-bedroom, three-and-a-half-bath home, just steps from Lake Bessie. Set ... 

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$1,300,000
Provided courtesy of EXECUTIVE PROPERTIES
45 Photos 111 Main Street Windermere, FL 34786

111 Main Street
Windermere, FL 34786
Windermere Town
Residential

MLS# O6313903 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2272 Sqft
Area: 34786 - Windermere, Subdivision: Windermere Town

Prime Windermere Location! Fully Renovated and Move-In Ready!Dont miss this beautifully updated 3-bedroom, 2-bath home nestled in the heart of Wind... 

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$999,000
Reduced -$90,000
Provided courtesy of SUNDIAL REAL ESTATE LLC
44 Photos 616 Magnolia Street Windermere, FL 34786

616 Magnolia Street
Windermere, FL 34786
Windermere Town
Residential

MLS# O6315742 / Active
4 Beds, 2.00 Total Baths, 2 Full Bath, 2582 Sqft
Area: 34786 - Windermere, Subdivision: Windermere Town

Great Open Floorplan - 1 Story Ranch - Large Covered Rear Screened Porch - 4 bedrooms - 2 baths - Vaulted Ceilings - Large Fenced Lot - Located on ... 

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$890,000
Provided courtesy of VINTAGE REALTY GROUP LLC
47 Photos 311 E 8th Avenue Windermere, FL 34786

311 E 8th Avenue
Windermere, FL 34786
Windermere Town
Rental

MLS# O6302814 / Active
5 Beds, 4.00 Total Baths, 4 Full Bath, 3502 Sqft
Type: SingleFamilyResidence, Area: 34786 - Windermere

Price Reduced! Lakefront Living in the Heart of Windermere Don't miss this rare opportunity to lease a beautifully renovated lakefront home on the ... 

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$6,750
Reduced -$750
Provided courtesy of COLDWELL BANKER RESIDENTIAL RE
49 Photos 307 W 4th Avenue Windermere, FL 34786

307 W 4th Avenue
Windermere, FL 34786
Windermere Town
Rental

MLS# O6275058 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 3190 Sqft
Type: SingleFamilyResidence, Area: 34786 - Windermere

Executive rental pool home located in the charming town of Windermere! The location is just two block from Main st and all that downtown Windermere... 

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$6,450
Provided courtesy of MAINFRAME REAL ESTATE

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