Searching on:
- Subdivision Like Windermere Town
Single Family
- Price: $4,899,000.00
- Price sqft: $504.53 / sqft
- Days On Market: 251
- Bedrooms: 7
- Baths: 11
- Garage / Parking Spaces: 3
- Bldg sqft: 9710
- Acreage: 1.09 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: Yes
- Wateraccess: Yes
- Waterfront Type: Beach Front,Lake Privileges
- Year Built: 2019
MLS#: O6292745
- County: ORANGE
- City: WINDERMERE
- Zipcode: 34786
- Subdivision: Windermere Town
- Elementary School: Windermere Elem
- Middle School: Gotha Middle
- High School: Olympia High
- Provided by: COMPASS FLORIDA LLC
- DMCA Notice
Description
- LAKEFRONT GRANDEUR IN WINDERMERE | A MASTERPIECE ON LAKE DOWN Unveiling a rare opportunity to own an architectural masterpiece on the famed Butler Chain of Lakesa residence that redefines lakefront l
Single Family
- Price: $2,375,000.00
- Price sqft: $379.88 / sqft
- Previous Price: $2,399,000
- Last Price Change: 11/24/25
- Days On Market: 258
- Bedrooms: 5
- Baths: 5
- Garage / Parking Spaces: 3
- Bldg sqft: 6252
- Acreage: 0.51 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: No
- Year Built: 1995
MLS#: O6290296
- County: ORANGE
- City: WINDERMERE
- Zipcode: 34786
- Subdivision: Windermere Town
- Elementary School: Windermere Elem
- Middle School: Gotha Middle
- High School: Olympia High
- Provided by: UPSIDE REAL ESTATE INC
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- DMCA Notice
Description
- Step inside this beautifully updated home where clean lines, soaring ceilings, and two story windows fill every corner with natural light. A floating staircase makes a stunning first impression, while
Single Family
- Price: $2,375,000.00
- Price sqft: $466.79 / sqft
- Previous Price: $2,425,000
- Last Price Change: 11/25/25
- Days On Market: 53
- Bedrooms: 4
- Baths: 5
- Garage / Parking Spaces: 3
- Bldg sqft: 5088
- Acreage: 0.74 acres
- Pool: No
- Waterfront: No
- Year Built: 2025
MLS#: O6350454
- County: ORANGE
- City: WINDERMERE
- Zipcode: 34786
- Subdivision: Windermere Town Rep
- Provided by: TALENT REALTY SOLUTIONS
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- DMCA Notice
Description
- Seller is Motivated and open to negotiate! Luxury new construction lakefront home in Windermere, newly completed. Situated on Lake Bessie, this modern custom residence delivers architectural elegance,
Single Family
- Price: $2,150,000.00
- Price sqft: $607.17 / sqft
- Previous Price: $2,269,500
- Last Price Change: 11/08/25
- Days On Market: 349
- Bedrooms: 3
- Baths: 3
- Garage / Parking Spaces: 2
- Bldg sqft: 3541
- Acreage: 1.43 acres
- Pool: No
- Waterfront: Yes
- Wateraccess: Yes
- Waterfront Type: Lake Privileges
- Year Built: 1974
MLS#: O6263552
- County: ORANGE
- City: WINDERMERE
- Zipcode: 34786
- Subdivision: Windermere Town Rep
- Elementary School: Windermere Elem
- Middle School: Gotha Middle
- High School: Olympia High
- Provided by: PREMIER SOTHEBYS INT'L REALTY
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- DMCA Notice
Description
- One or more photo(s) has been virtually staged. Back on market buyers home sale contingency did not clear. Inspection and appraisal were completed satisfactorily, no fault of the seller or property.
Single Family
- Price: $1,660,000.00
- Price sqft: $436.27 / sqft
- Previous Price: $1,750,000
- Last Price Change: 11/22/25
- Days On Market: 115
- Bedrooms: 5
- Baths: 4
- Garage / Parking Spaces: 2
- Bldg sqft: 3805
- Acreage: 0.23 acres
- Pool: No
- Waterfront: Yes
- Wateraccess: Yes
- Waterfront Type: Lake Front
- Year Built: 1913
MLS#: O6333319
- County: ORANGE
- City: WINDERMERE
- Zipcode: 34786
- Subdivision: Windermere Town
- Elementary School: Windermere Elem
- Middle School: Gotha Middle
- High School: Olympia High
- Provided by: COLDWELL BANKER RESIDENTIAL RE
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- DMCA Notice
Description
- Luxury Lakefront Living in Downtown Windermere | Fresh Opportunity on Lake Bessie. Welcome to your private slice of lakefront paradise on Lake Bessie, where luxury living meets laid back charm in the
Single Family
- Price: $1,550,000.00
- Price sqft: $267.66 / sqft
- Previous Price: $1,650,000
- Last Price Change: 11/24/25
- Days On Market: 68
- Bedrooms: 5
- Baths: 4
- Garage / Parking Spaces: 2
- Bldg sqft: 5791
- Acreage: 0.42 acres
- Pool: Yes
- Waterfront: No
- Year Built: 1978
MLS#: O6344558
- County: ORANGE
- City: WINDERMERE
- Zipcode: 34786
- Subdivision: Windermere Town Rep
- Elementary School: Windermere Elem
- Middle School: Gotha Middle
- High School: Windermere High School
- Provided by: ISLEWORTH REALTY LLC
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- DMCA Notice
Description
- A new long elegantly paved driveway leads up to this beautifully updated 5 bedroom, 4,200 sq. ft. home in the charming Town of Windermere. With lush views of established landscaping & surrounding tree
Single Family
- Price: $1,237,000.00
- Price sqft: $373.83 / sqft
- Previous Price: $1,244,000
- Last Price Change: 11/28/25
- Days On Market: 142
- Bedrooms: 4
- Baths: 4
- Garage / Parking Spaces: 2
- Bldg sqft: 3309
- Acreage: 0.29 acres
- Pool: Yes
- Waterfront: No
- Year Built: 1989
MLS#: O6326261
- County: ORANGE
- City: WINDERMERE
- Zipcode: 34786
- Subdivision: Windermere Town
- Elementary School: Windermere Elem
- Middle School: Gotha Middle
- High School: Olympia High
- Provided by: EXECUTIVE PROPERTIES
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- DMCA Notice
Description
- Modern upgrades meet timeless Windermere charm in this fully reimagined four bedroom, three and a half bath home, just steps from Lake Bessie. Set on a beautifully manicured corner lot with no HOA, th
Single Family
- Price: $895,000.00
- Price sqft: $227.39 / sqft
- Days On Market: 23
- Bedrooms: 4
- Baths: 3
- Garage / Parking Spaces: 3
- Bldg sqft: 3936
- Acreage: 0.38 acres
- Pool: No
- Waterfront: No
- Year Built: 1984
MLS#: O6357207
- County: ORANGE
- City: WINDERMERE
- Zipcode: 34786
- Subdivision: Windermere Town
- Elementary School: Windermere Elem
- Middle School: Gotha Middle
- High School: Olympia High
- Provided by: UPSIDE REAL ESTATE INC
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- DMCA Notice
Description
- This traditional farmhouse blends Old Florida charm with everyday comfort a rare opportunity in the heart of Windermere. Full of character inside and out, the home sits on an elevated corner lot, off
Single Family
- Price: $890,000.00
- Price sqft: $325.77 / sqft
- Previous Price: $949,000
- Last Price Change: 11/21/25
- Days On Market: 181
- Bedrooms: 3
- Baths: 2
- Garage / Parking Spaces: 2
- Bldg sqft: 2732
- Acreage: 0.39 acres
- Pool: No
- Waterfront: No
- Year Built: 1984
MLS#: O6313903
- County: ORANGE
- City: WINDERMERE
- Zipcode: 34786
- Subdivision: Windermere Town
- Provided by: SUNDIAL REAL ESTATE LLC
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- DMCA Notice
Description
- Prime Windermere Location! Fully Renovated and Move In Ready! Dont miss this beautifully updated 3 bedroom, 2 bath home nestled in the heart of Windermere. Situated on an oversized, fully fenced lot,
Single Family
- Price: $885,000.00
- Price sqft: $305.91 / sqft
- Days On Market: 8
- Bedrooms: 2
- Baths: 2
- Garage / Parking Spaces: 3
- Bldg sqft: 2893
- Acreage: 0.38 acres
- Pool: No
- Waterfront: No
- Year Built: 1915
MLS#: O6362356
- County: ORANGE
- City: WINDERMERE
- Zipcode: 34786
- Subdivision: Windermere Town
- Elementary School: Windermere Elem
- Middle School: Gotha Middle
- High School: Olympia High
- Provided by: UPSIDE REAL ESTATE INC
-
- DMCA Notice
Description
- Step into a storybook cottage tucked in the heart of Windermere, where history whispers through every room and morning light dances across original 1915 details. Part of the early homestead still rema
