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  1. Subdivision Like Windermere
2 Chase Road
New Construction
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Details for 2 Chase Road, WINDERMERE, FL 34786
Single Family
  1. Price: $3,200,000.00
  2. Price sqft: $822.83 / sqft
  3. Days On Market: 117
  4. Bedrooms: 4
  5. Baths: 5
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3889
  8. Acreage: 0.44 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2026
MLS#: O6345197
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere
  5. Elementary School: Windermere Elem
  6. Middle School: Chain of Lakes
  7. High School: Olympia
  8. Provided by: REAL BROKER, LLC
  9. mfrmls
  10. DMCA Notice
Pre construction. To be built. Pre construction. To be built. Pre construction | to be built | designed for unparalleled luxury discover an extraordinary opportunity to own a masterfully designed luxu
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713 Main Street
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Details for 713 Main Street, WINDERMERE, FL 34786
Single Family
  1. Price: $2,285,000.00
  2. Price sqft: $337.02 / sqft
  3. Days On Market: 25
  4. Bedrooms: 6
  5. Baths: 6
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 6780
  8. Acreage: 0.37 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 2013
MLS#: O6368185
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere
  5. Elementary School: Windermere Elem
  6. Middle School: Gotha
  7. High School: Olympia
  8. Provided by: THE REAL ESTATE COLLECTION LLC
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Architecturally refined and thoughtfully designed, this custom built Transitional Craftsman residence blends timeless craftsmanship with modern luxury in the heart of Historic Olde Windermere. Rich wo
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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: $2,275,000.00
  2. Price sqft: $447.13 / sqft
  3. Previous Price: $2,375,000
  4. Last Price Change: 12/15/25
  5. Days On Market: 96
  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
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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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311 8th Avenue
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Details for 311 8th Avenue, WINDERMERE, FL 34786
Single Family
  1. Price: $1,660,000.00
  2. Price sqft: $436.27 / sqft
  3. Previous Price: $1,750,000
  4. Last Price Change: 10/21/25
  5. Days On Market: 158
  6. Bedrooms: 5
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 3805
  10. Acreage: 0.23 acres
  11. Pool: No
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Lake Front
  15. Year Built: 1913
MLS#: O6333319
  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
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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
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2509 Ridgewind Way
Green Listing
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Details for 2509 Ridgewind Way, WINDERMERE, FL 34786
Single Family
  1. Price: $1,545,000.00
  2. Price sqft: $284.95 / sqft
  3. Previous Price: $1,585,000
  4. Last Price Change: 12/02/25
  5. Days On Market: 70
  6. Bedrooms: 4
  7. Baths: 4
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 5422
  10. Acreage: 0.75 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 1998
MLS#: O6354737
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Estates At Windermere
  5. Elementary School: Lake Whitney Elem
  6. Middle School: SunRidge
  7. High School: West Orange
  8. Provided by: COMPASS FLORIDA LLC
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If youve dreamed of a home that feels both timeless and tailor made for modern living, welcome to 2509 Ridgewind Way in the gated Estates at Windermere. Set on .75 acre this updated Southern estate co
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101 Lee Street
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Details for 101 Lee Street, WINDERMERE, FL 34786
Single Family
  1. Price: $1,485,000.00
  2. Price sqft: $256.43 / sqft
  3. Previous Price: $1,550,000
  4. Last Price Change: 12/08/25
  5. Days On Market: 111
  6. Bedrooms: 5
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 5791
  10. Acreage: 0.42 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 1978
MLS#: O6344558
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere Town Rep
  5. Elementary School: Windermere Elem
  6. Middle School: Gotha
  7. High School: Windermere
  8. Provided by: ISLEWORTH REALTY LLC
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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
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7135 Horizon Circle
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Reduced
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Details for 7135 Horizon Circle, WINDERMERE, FL 34786
Single Family
  1. Price: $1,399,000.00
  2. Price sqft: $312.70 / sqft
  3. Previous Price: $1,449,000
  4. Last Price Change: 01/08/26
  5. Days On Market: 181
  6. Bedrooms: 4
  7. Baths: 4
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 4474
  10. Acreage: 0.74 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 1993
MLS#: O6327225
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere Reserve
  5. Elementary School: Windermere Elem
  6. Middle School: Chain of Lakes
  7. High School: Olympia
  8. Provided by: THE BOSCH GROUP
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New price, new year! Nestled in the true town of windermere is this absolutely stunning, meticulously maintained pool home with tall ceilings and lots of land surrounding on both sides! This hidden ge
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8162 Oak Park Road
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Details for 8162 Oak Park Road, ORLANDO, FL 32819
Single Family
  1. Price: $1,249,000.00
  2. Price sqft: $166.78 / sqft
  3. Days On Market: 35
  4. Bedrooms: 4
  5. Baths: 4
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 7489
  8. Acreage: 1.00 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1986
MLS#: O6365197
  1. County: ORANGE
  2. City: ORLANDO
  3. Zipcode: 32819
  4. Subdivision: Windermere Heights Sec 03
  5. Elementary School: Palm Lake Elem
  6. Middle School: Chain of Lakes
  7. High School: Olympia
  8. Provided by: COLDWELL BANKER REALTY
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Looking for land and no hoa, but want to be close to everything and have excellent schools and easy access to all major highways? This one is for you!! Set on 1 acre of prime property in coveted dr. P
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10442 Birch Tree Lane
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Details for 10442 Birch Tree Lane, WINDERMERE, FL 34786
Single Family
  1. Price: $1,249,000.00
  2. Price sqft: $251.46 / sqft
  3. Previous Price: $1,275,000
  4. Last Price Change: 01/03/26
  5. Days On Market: 25
  6. Bedrooms: 4
  7. Baths: 3
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 4967
  10. Acreage: 1.02 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. Year Built: 1998
MLS#: O6367335
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere Downs Ph 03
  5. Elementary School: Thornebrooke Elem
  6. Middle School: Gotha
  7. High School: Olympia
  8. Provided by: CHARLES RUTENBERG REALTY ORLANDO
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Set at the end of a cul de sac on a sprawling acre+ lot, this 4 bedroom, 3 bath pool home in Windermere Downs, offers over 3,500 sq ft and sits well back from the road with a long private driveway and
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6146 Golden Dewdrop Trail
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Details for 6146 Golden Dewdrop Trail, WINDERMERE, FL 34786
Single Family
  1. Price: $1,225,000.00
  2. Price sqft: $228.08 / sqft
  3. Days On Market: 23
  4. Bedrooms: 7
  5. Baths: 5
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 5371
  8. Acreage: 0.20 acres
  9. Pool: Yes
  10. Community Pool: Yes
  11. Spa/HotTub: Yes
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Pond
  15. Year Built: 2012
MLS#: O6368142
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere Lndgs Fd1
  5. Elementary School: SunRidge
  6. Middle School: Horizon West
  7. High School: Windermere
  8. Provided by: KELLER WILLIAMS CLASSIC
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Move in ready and thoughtfully upgraded, this spacious residence is located in the established windermere landing community and offers serene pond views, energy efficient construction, and a flexible
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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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Listing Data ©2026 Royal Palm Coast Realtor® Association
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Datafeed Last updated on January 13, 2026 @ 12:00 am
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