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  1. Subdivision Like Windermere Town
  2. Listing Status = Active
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: 25
  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 Front
  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 and walkability to town. The Town of W
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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: 185
  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,
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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: 2
  3. Acreage: 0.32 acres
  4. Pool: No
  5. Waterfront: Yes
  6. Wateraccess: Yes
  7. Waterfront Type: Lake
  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. Provided through
  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
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106 Palm Street
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Details for 106 Palm Street, WINDERMERE, FL 34786
Single Family
  1. Price: $1,399,000.00
  2. Price sqft: $383.60 / sqft
  3. Days On Market: 17
  4. Bedrooms: 5
  5. Baths: 5
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3647
  8. Acreage: 0.37 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1960
MLS#: O6391350
  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: KELLER WILLIAMS WINTER PARK
  9. mfrmls
  10. DMCA Notice
Set on a large, tree lined lot just moments from historic downtown Windermere, this fully reimagined residence blends modern luxury with timeless charmdelivering a level of craftsmanship and detail th
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4 Chase Road
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Details for 4 Chase Road, WINDERMERE, FL 34786
Single Family
  1. Price: $900,000.00
  2. Price sqft: $377.20 / sqft
  3. Days On Market: 50
  4. Bedrooms: 3
  5. Baths: 2
  6. Garage / Parking Spaces: 1
  7. Bldg sqft: 2386
  8. Acreage: 0.29 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 1971
MLS#: O6384257
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere Town
  5. Provided by: REAL BROKER, LLC
  6. mfrmls
  7. DMCA Notice
FULLY RENOVATED DREAM HOME. This home is located right in the heart of the Town of Windermere. Welcome to 4 Chase Rd, Windermere a refined expression of luxury living where elevated design, privacy,
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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: 4
  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. Provided through
  10. DMCA Notice
The 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 now features thoughtful exterior enh
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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: 4
  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 Middle
  7. High School: Olympia
  8. Provided by: EXP REALTY LLC
  9. mfrmls
  10. DMCA Notice
The 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 now features thoughtful exterior enh
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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: 130
  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
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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: 438
  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
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721 Magnolia Street
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Details for 721 Magnolia Street, WINDERMERE, FL 34786
Rental
  1. Price: $2,250.00
  2. Price sqft: $2.53 / sqft
  3. Days On Market: 42
  4. Bedrooms: 2
  5. Baths: 1
  6. Bldg sqft: 891
  7. Acreage: 0.38 acres
  8. Pool: No
  9. Waterfront: No
  10. Year Built: 1913
MLS#: S5144805
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere Town
  5. Provided by: EXP REALTY LLC
  6. mfrmls
  7. DMCA Notice
This Charming Fully Renovated Home is available for rent in the Heart of Downtown Windermere Welcome to this beautifully remodeled 2 bedroom, 1 bathroom gem, ideally located within short distance to t
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Tropic Shores Realty - Crystal River
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Listings provided courtesy of The Hernando County Association of Realtors MLS.
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Datafeed Last updated on April 11, 2026 @ 12:00 am
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