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    1. Subdivision Like Windermere Town
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    325 Magnolia Street
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    Details for 325 Magnolia Street, WINDERMERE, FL 34786
    Single Family
    1. Price: $2,475,000.00
    2. Price sqft: $509.36 / sqft
    3. Days On Market: 52
    4. Bedrooms: 4
    5. Baths: 3
    6. Garage / Parking Spaces: 2
    7. Bldg sqft: 4859
    8. Acreage: 2.97 acres
    9. Pool: Yes
    10. Waterfront: Yes
    11. Wateraccess: Yes
    12. Waterfront Type: Lake Privileges
    13. Year Built: 1954
    MLS#: O6391047
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Subdivision: Windermere Town
    5. Elementary School: Windermere Elem
    6. Middle School: Gotha
    7. High School: Olympia
    8. Provided by: REVEL REALTY LLC
    9. mfrmls
    10. DMCA Notice
    Location Location Location. Set along the shores of Lake Down, part of the Butler Chain of Lakes, this Windermere home offers a rare mix of laid back lake living with walkability to town, and a bike r
    Listing Details and 51 Additional Pictures
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    436 7th Avenue
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    New Construction
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    Details for 436 7th Avenue, WINDERMERE, FL 34786
    Single Family
    1. Price: $2,175,000.00
    2. Price sqft: $427.48 / sqft
    3. Previous Price: $2,275,000
    4. Last Price Change: 01/13/26
    5. Days On Market: 212
    6. Bedrooms: 4
    7. Baths: 5
    8. Garage / Parking Spaces: 3
    9. Bldg sqft: 5088
    10. Acreage: 0.74 acres
    11. Pool: No
    12. Waterfront: No
    13. Year Built: 2025
    MLS#: O6350454
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Subdivision: Windermere Town Rep
    5. Provided by: TALENT REALTY SOLUTIONS
    6. mfrmls
    7. DMCA Notice
    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,
    Listing Details and 29 Additional Pictures
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    212 1st Avenue
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    Details for 212 1st Avenue, WINDERMERE, FL 34786
    Land
    1. Price: $1,600,000.00
    2. Days On Market: 29
    3. Acreage: 0.32 acres
    4. Pool: No
    5. Waterfront: Yes
    6. Wateraccess: Yes
    7. Waterfront Type: Lake Privileges
    8. Year Built: Not Available
    MLS#: S5147532
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Subdivision: Windermere Town
    5. Elementary School: Windermere Elem
    6. Middle School: Gotha
    7. High School: Olympia
    8. Provided by: HOME WISE REALTY GROUP, INC.
    9. mfrmls
    10. DMCA Notice
    Positioned along the coveted Butler Chain of Lakes, this waterfront residence offers an exceptional opportunity in the Town of Windermere. Boasting approximately 65 feet of private frontage and a dedi
    Listing Details and 20 Additional Pictures
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    212 1st Avenue
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    Details for 212 1st Avenue, WINDERMERE, FL 34786
    Single Family
    1. Price: $1,600,000.00
    2. Price sqft: $411.10 / sqft
    3. Days On Market: 11
    4. Bedrooms: 4
    5. Baths: 2
    6. Garage / Parking Spaces: 2
    7. Bldg sqft: 3892
    8. Acreage: 0.32 acres
    9. Pool: No
    10. Waterfront: Yes
    11. Wateraccess: Yes
    12. Waterfront Type: Lake Privileges
    13. Year Built: 1959
    MLS#: S5148430
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Subdivision: Windermere Town
    5. Elementary School: Windermere Elem
    6. Middle School: Gotha
    7. High School: Olympia
    8. Provided by: HOME WISE REALTY GROUP, INC.
    9. mfrmls
    10. DMCA Notice
    Positioned along the coveted Butler Chain of Lakes, this waterfront residence offers an exceptional opportunity to live in the Town of Windermere. Boasting approximately 85 feet of private frontage an
    Listing Details and 19 Additional Pictures
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    109 12th Avenue
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    Details for 109 12th Avenue, WINDERMERE, FL 34786
    Single Family
    1. Price: $1,225,000.00
    2. Price sqft: $370.20 / sqft
    3. Days On Market: 23
    4. Bedrooms: 4
    5. Baths: 4
    6. Garage / Parking Spaces: 2
    7. Bldg sqft: 3309
    8. Acreage: 0.29 acres
    9. Pool: Yes
    10. Spa/HotTub: Yes
    11. Waterfront: No
    12. Year Built: 1989
    MLS#: O6394569
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Subdivision: Windermere Town
    5. Elementary School: Windermere Elem
    6. Middle School: Gotha
    7. High School: Olympia
    8. Provided by: UPSIDE REAL ESTATE INC
    9. mfrmls
    10. DMCA Notice
    Modern style blends with Windermere charm. This totally renovated home is located just steps from Lake Bessie in the Town of Windermere. Set on a beautifully landscaped corner lot with no HOA, this h
    Listing Details and 42 Additional Pictures
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    715 Magnolia Street
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    Details for 715 Magnolia Street, WINDERMERE, FL 34786
    Single Family
    1. Price: $1,175,000.00
    2. Price sqft: $277.45 / sqft
    3. Previous Price: $1,250,000
    4. Last Price Change: 04/28/26
    5. Days On Market: 27
    6. Bedrooms: 5
    7. Baths: 4
    8. Garage / Parking Spaces: 3
    9. Bldg sqft: 4235
    10. Acreage: 0.38 acres
    11. Pool: No
    12. Waterfront: No
    13. Year Built: 1999
    MLS#: S5147648
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Subdivision: Windermere Town
    5. Elementary School: Windermere Elem
    6. Middle School: Gotha
    7. High School: Olympia
    8. Provided by: IRIS INTERNATIONAL
    9. mfrmls
    10. DMCA Notice
    ADU A beautiful home located in the heart of downtown Windermere offering 4 bedrooms, 3 bathrooms, with a perfect blend of comfort and convenience. The house features hardwood floors throughout, and l
    Listing Details and 43 Additional Pictures
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    825 Oakdale Street
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    Details for 825 Oakdale Street, WINDERMERE, FL 34786
    Single Family
    1. Price: $792,500.00
    2. Price sqft: $278.27 / sqft
    3. Days On Market: 31
    4. Bedrooms: 3
    5. Baths: 2
    6. Garage / Parking Spaces: 1
    7. Bldg sqft: 2848
    8. Acreage: 0.38 acres
    9. Pool: No
    10. Waterfront: No
    11. Year Built: 1935
    MLS#: O6396351
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Subdivision: Windermere Town
    5. Elementary School: Windermere Elem
    6. Middle School: Gotha
    7. High School: Olympia
    8. Provided by: EXP REALTY LLC
    9. mfrmls
    10. DMCA Notice
    Back on the market no fault of the home! Only home on windermeres iconic sandy streets under $800,000 dont miss your chance. Back on the market and better than ever, this charming traditional cottage
    Listing Details and 49 Additional Pictures
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    311 8th Avenue
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    Details for 311 8th Avenue, WINDERMERE, FL 34786
    Rental
    1. Price: $6,000.00
    2. Price sqft: $1.22 / sqft
    3. Previous Price: $6,500
    4. Last Price Change: 03/18/26
    5. Days On Market: 158
    6. Bedrooms: 5
    7. Baths: 4
    8. Garage / Parking Spaces: 2
    9. Bldg sqft: 4928
    10. Acreage: 0.23 acres
    11. Pool: No
    12. Waterfront: No
    13. Year Built: 1913
    MLS#: O6364016
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Subdivision: Windermere Town
    5. Elementary School: Windermere Elem
    6. Middle School: Gotha
    7. High School: Olympia
    8. Provided by: COLDWELL BANKER RESIDENTIAL RE
    9. mfrmls
    10. DMCA Notice
    One or more photo(s) has been virtually staged. Luxury Lakefront Executive Rental in Downtown Windermere on Lake Bessie. Now offered at a newly adjusted price, this rare 5 bedroom lakefront home prese
    Listing Details and 53 Additional Pictures
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    307 4th Avenue
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    Details for 307 4th Avenue, WINDERMERE, FL 34786
    Rental
    1. Price: $5,475.00
    2. Price sqft: $1.72 / sqft
    3. Previous Price: $5,900
    4. Last Price Change: 02/28/26
    5. Days On Market: 465
    6. Bedrooms: 4
    7. Baths: 3
    8. Garage / Parking Spaces: 2
    9. Bldg sqft: 3190
    10. Acreage: 0.38 acres
    11. Pool: Yes
    12. Waterfront: No
    13. Year Built: 1968
    MLS#: O6275058
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Subdivision: Windermere Town
    5. Provided by: MAINFRAME REAL ESTATE
    6. mfrmls
    7. DMCA Notice
    One or more photo(s) has been virtually staged. Available for lease, this refined single story pool residence is located in the Town of Windermere, just moments from Main Street and the downtown distr
    Listing Details and 55 Additional Pictures
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    Listings provided courtesy of The Hernando County Association of Realtors MLS.
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    Datafeed Last updated on May 9, 2026 @ 12:00 am
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