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  1. Michelle Hill, ABR,AHWD,PA,PSA,REALTOR ®,SFR
  2. Tropic Shores Realty
  3. Mobile: 352.247.2177
  4. 229.834.4988
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  1. Subdivision Like Windermere
  2. Listing Status = Active
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: 175
  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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505 Jennifer Lane
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Details for 505 Jennifer Lane, Windermere, FL 34786
Single Family
  1. Price: $2,250,000.00
  2. Price sqft: $421.03 / sqft
  3. Days On Market: 12
  4. Bedrooms: 4
  5. Baths: 4
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 5344
  8. Acreage: 1.00 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1989
MLS#: O6384643
  1. County: ORANGE
  2. City: Windermere
  3. Zipcode: 34786
  4. Subdivision: Windermere Oaks
  5. Elementary School: Windermere Elem
  6. Middle School: Chain of Lakes
  7. High School: Olympia
  8. Provided by: COMPASS FLORIDA LLC
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Villa Casablanca | Luxury Windermere Estate on 1 Acre. Some homes are built. Villa Casablanca was transformed. Set on a rare private acre within one of Windermeres most privately held enclaves this
Listing Details and 94 Additional Pictures
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505 Jennifer Lane
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Details for 505 Jennifer Lane, WINDERMERE, FL 34786
Single Family
  1. Price: $2,250,000.00
  2. Price sqft: $421.03 / sqft
  3. Days On Market: 12
  4. Bedrooms: 4
  5. Baths: 4
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 5344
  8. Acreage: 1.00 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 1989
MLS#: O6384643
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere Oaks
  5. Elementary School: Windermere Elem
  6. Middle School: Chain of Lakes
  7. High School: Olympia
  8. Provided by: COMPASS FLORIDA LLC
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  10. DMCA Notice
Villa Casablanca | Luxury Windermere Estate on 1 Acre. Some homes are built. Villa Casablanca was transformed. Set on a rare private acre within one of Windermeres most privately held enclaves this
Listing Details and 94 Additional Pictures
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713 Main Street
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Details for 713 Main Street, WINDERMERE, FL 34786
Single Family
  1. Price: $2,235,000.00
  2. Price sqft: $329.65 / sqft
  3. Previous Price: $2,285,000
  4. Last Price Change: 02/28/26
  5. Days On Market: 83
  6. Bedrooms: 6
  7. Baths: 6
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 6780
  10. Acreage: 0.37 acres
  11. Pool: No
  12. Waterfront: No
  13. 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: $2,175,000.00
  2. Price sqft: $427.48 / sqft
  3. Previous Price: $2,275,000
  4. Last Price Change: 01/13/26
  5. Days On Market: 154
  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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13048 Lake Roper Ct.
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Details for 13048 Lake Roper Ct., WINDERMERE, FL 34786
Single Family
  1. Price: $1,950,000.00
  2. Price sqft: $347.10 / sqft
  3. Previous Price: $1,999,000
  4. Last Price Change: 02/08/26
  5. Days On Market: 180
  6. Bedrooms: 5
  7. Baths: 4
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 5618
  10. Acreage: 1.63 acres
  11. Pool: Yes
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Lake Front
  15. Year Built: 2002
MLS#: O6342354
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere Pointe
  5. Provided by: WOODSTONE INVESTMENTS LLC
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Back on the market. Unmatched Value! The only Windermere lakefront home with boat access available under $2M. Don't miss this opportunity. Enjoy the e evenings to a breathtaking sunset at your own pri
Listing Details and 79 Additional Pictures
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311 8th Avenue
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Details for 311 8th Avenue, WINDERMERE, FL 34786
Single Family
  1. Price: $1,549,000.00
  2. Price sqft: $407.10 / sqft
  3. Previous Price: $1,660,000
  4. Last Price Change: 02/24/26
  5. Days On Market: 216
  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 Home in Downtown Windermere. New Price No HOA Private Lake Bessie. Now offered at a newly adjusted price, this exceptional luxury lakefront home in Windermere, Florida presents o
Listing Details and 58 Additional Pictures
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8133 Oakland Place
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Details for 8133 Oakland Place, ORLANDO, FL 32819
Single Family
  1. Price: $1,500,000.00
  2. Price sqft: $237.19 / sqft
  3. Days On Market: 16
  4. Bedrooms: 5
  5. Baths: 4
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 6324
  8. Acreage: 1.00 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1991
MLS#: O6384690
  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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One or more photo(s) has been virtually staged. Welcome home to your 1 of a kind charming Neo Classical Colonial solid brick home located on a spacious 1 acre lot in the heart of Dr. Phillips with no
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13596 Gorgona Isle Drive
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Reduced
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Details for 13596 Gorgona Isle Drive, WINDERMERE, FL 34786
Single Family
  1. Price: $1,396,000.00
  2. Price sqft: $344.01 / sqft
  3. Previous Price: $1,452,000
  4. Last Price Change: 03/07/26
  5. Days On Market: 54
  6. Bedrooms: 6
  7. Baths: 5
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 4058
  10. Acreage: 0.20 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 2017
MLS#: O6374555
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere Isle
  5. Elementary School: Castleview
  6. Middle School: Horizon West
  7. High School: Horizon
  8. Provided by: WRA BUSINESS & REAL ESTATE
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Stunning Two Story Pool Home in Prime Windermere Location Welcome to this exceptional two story residence located in the highly desirable Windermere area, offering the perfect blend of luxury, space,
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8236 Procida Isle Lane
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Details for 8236 Procida Isle Lane, WINDERMERE, FL 34786
Single Family
  1. Price: $1,250,000.00
  2. Price sqft: $243.62 / sqft
  3. Days On Market: 19
  4. Bedrooms: 6
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 5131
  8. Acreage: 0.16 acres
  9. Pool: Yes
  10. Community Pool: Yes
  11. Waterfront: No
  12. Year Built: 2018
MLS#: O6383546
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windermere Isle Ph 2
  5. Elementary School: Castleview
  6. Middle School: Horizon West
  7. High School: Horizon
  8. Provided by: WRA BUSINESS & REAL ESTATE
  9. mfrmls
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This house is the perfect blend of luxury, comfort and modern convenience. From the moment you arrive, you're welcomed by a charming brick paver front porch that leads into a light filled foyer with a
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