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    1. Subdivision Like Windermere
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    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: 234
    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 Middle
    7. High School: Olympia High
    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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    105 Pine Street
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    Details for 105 Pine Street, WINDERMERE, FL 34786
    Single Family
    1. Price: $2,500,000.00
    2. Price sqft: $342.65 / sqft
    3. Days On Market: 2
    4. Bedrooms: 5
    5. Baths: 6
    6. Garage / Parking Spaces: 3
    7. Bldg sqft: 7296
    8. Acreage: 0.57 acres
    9. Pool: Yes
    10. Spa/HotTub: Yes
    11. Waterfront: No
    12. Year Built: 2015
    MLS#: O6405163
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Subdivision: Windermere
    5. Elementary School: Windermere Elem
    6. Middle School: Gotha Middle
    7. High School: Olympia High
    8. Provided by: ALIGN REAL ESTATE LLC
    9. mfrmls
    10. DMCA Notice
    Extraordinary multigenerational living opportunity in the Town of Windermere, where mature oak trees and a quiet, established setting create a true sense of place just moments from the Butler Chain of
    Listing Details and 72 Additional Pictures
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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: 53
    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 Middle
    7. High School: Olympia High
    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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    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: 04/20/26
    5. Days On Market: 142
    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 Middle
    7. High School: Olympia High
    8. Provided by: THE REAL ESTATE COLLECTION LLC
    9. mfrmls
    10. DMCA Notice
    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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    505 Jennifer Lane
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    Details for 505 Jennifer Lane, WINDERMERE, FL 34786
    Single Family
    1. Price: $2,199,000.00
    2. Price sqft: $411.49 / sqft
    3. Days On Market: 71
    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 Middle
    7. High School: Olympia High
    8. Provided by: COMPASS FLORIDA LLC
    9. mfrmls
    10. DMCA Notice
    Villa Casablanca | Luxury Windermere Estate on 1 Acre. Some homes are built. this was transformed. Set on a rare private acre within one of Windermeres most privately held enclaves this estate makes
    Listing Details and 94 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: 05/05/26
    5. Days On Market: 213
    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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    12699 Hawkstone Drive
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    Details for 12699 Hawkstone Drive, WINDERMERE, FL 34786
    Single Family
    1. Price: $2,125,000.00
    2. Price sqft: $430.51 / sqft
    3. Days On Market: 16
    4. Bedrooms: 4
    5. Baths: 5
    6. Garage / Parking Spaces: 2
    7. Bldg sqft: 4936
    8. Acreage: 1.07 acres
    9. Pool: Yes
    10. Spa/HotTub: Yes
    11. Waterfront: Yes
    12. Wateraccess: Yes
    13. Waterfront Type: Lake Privileges
    14. Year Built: 2006
    MLS#: O6401293
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Subdivision: Lakes Windermere Ph 01 49 108
    5. Elementary School: Sunset Park Elem
    6. Middle School: Horizon West Middle School
    7. High School: Windermere High School
    8. Provided by: LAKEFIELD REALTY GROUP LLC
    9. mfrmls
    10. DMCA Notice
    Welcome to Chalet du Lac, set on the exclusive and private Lake Sawyer chain of lakes in Windermerewhere mornings are welcomed by sunrise over glistening waters dancing through a veil of Cypress trees
    Listing Details and 80 Additional Pictures
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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: $1,890,000.00
    2. Price sqft: $336.42 / sqft
    3. Previous Price: $1,950,000
    4. Last Price Change: 04/23/26
    5. Days On Market: 239
    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
    6. mfrmls
    7. DMCA Notice
    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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    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: 12
    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 Middle
    7. High School: Olympia High
    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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    212 1st Avenue
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    Details for 212 1st Avenue, WINDERMERE, FL 34786
    Land
    1. Price: $1,600,000.00
    2. Previous Price: $1,500,000
    3. Last Price Change: 04/10/26
    4. Days On Market: 30
    5. Acreage: 0.32 acres
    6. Pool: No
    7. Waterfront: Yes
    8. Wateraccess: Yes
    9. Waterfront Type: Lake Privileges
    10. 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 Middle
    7. High School: Olympia High
    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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    Equal Housing Opportunity
    Listings provided courtesy of The Hernando County Association of Realtors MLS.
    Listing Data ©2026 REALTOR® Association of Citrus County
    The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
    Display of MLS data is usually deemed reliable but is NOT guaranteed accurate.
    Datafeed Last updated on May 10, 2026 @ 12:00 am
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