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    1. Subdivision Like Davis Shores
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    43 Main Street
    New Construction
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    Listing Details for 43 Main Street, WINDERMERE, FL 34786
    Single Family
    1. Price: $3,500,000.00
    2. Price sqft: $817.76 / sqft
    3. Days On Market: 66
    4. Bedrooms: 4
    5. Baths: 4
    6. Garage / Parking Spaces: 2
    7. Bldg sqft: 4280
    8. Acreage: 0.37 acres
    9. Pool: No
    10. Waterfront: Yes
    11. Wateraccess: Yes
    12. Waterfront Type: Canal - Freshwater
    13. Year Built: 2026
    MLS#: O6387626
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Subdivision: Davis Shores
    5. Elementary School: Windermere Elem
    6. Middle School: Gotha Middle
    7. High School: Olympia High
    8. Provided by: GOLDEN GROUP REALTY LLC
    9. mfrmls
    10. DMCA Notice
    Under Construction. Modern New Construction on the Butler Chain Canal Downtown Windermere Experience bright, modern waterfront living in the heart of the Town of Windermere. This brand new construct
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    19 Main Street
    New Construction
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    Listing Details for 19 Main Street, WINDERMERE, FL 34786
    Single Family
    1. Price: $3,000,000.00
    2. Price sqft: $721.15 / sqft
    3. Days On Market: 80
    4. Bedrooms: 5
    5. Baths: 5
    6. Garage / Parking Spaces: 2
    7. Bldg sqft: 4160
    8. Acreage: 0.40 acres
    9. Pool: No
    10. Waterfront: Yes
    11. Wateraccess: Yes
    12. Waterfront Type: Canal - Freshwater
    13. Year Built: 2026
    MLS#: O6383837
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Subdivision: Davis Shores
    5. Elementary School: Windermere Elem
    6. Middle School: Gotha Middle
    7. High School: Olympia High
    8. Provided by: GOLDEN GROUP REALTY LLC
    9. mfrmls
    10. DMCA Notice
    Under Construction. New Construction in Downtown Windermere Waterfront on the Butler Chain of Lakes! Experience modern lakefront living in the heart of the golf cartfriendly Town of Windermere. This
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    81 Oakdale Street
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    Details for 81 Oakdale Street, WINDERMERE, FL 34786
    Single Family
    1. Price: $2,300,000.00
    2. Price sqft: $411.89 / sqft
    3. Previous Price: $2,500,000
    4. Last Price Change: 04/21/26
    5. Days On Market: 173
    6. Bedrooms: 5
    7. Baths: 5
    8. Garage / Parking Spaces: 3
    9. Bldg sqft: 5584
    10. Acreage: 0.42 acres
    11. Pool: No
    12. Waterfront: Yes
    13. Wateraccess: Yes
    14. Waterfront Type: Canal Front
    15. Year Built: 2001
    MLS#: S5138567
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Subdivision: Davis Shores
    5. Elementary School: Windermere Elem
    6. Middle School: Gotha Middle
    7. High School: Olympia High
    8. Provided by: COLDWELL BANKER RESIDENTIAL RE
    9. mfrmls
    10. DMCA Notice
    Gorgeous canal front home with direct access to the Butler Chain of Lakes and just four blocks from the heart of downtown Windermere, this 2024 luxury remodel offers the perfect blend of modern living
    Listing Details and 86 Additional Pictures
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    84 Oakdale St
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    Details for 84 Oakdale St, WINDERMERE, FL 34786
    Single Family
    1. Price: $1,875,000.00
    2. Price sqft: $412.81 / sqft
    3. Previous Price: $1,995,000
    4. Last Price Change: 04/18/26
    5. Days On Market: 117
    6. Bedrooms: 4
    7. Baths: 6
    8. Garage / Parking Spaces: 2
    9. Bldg sqft: 4542
    10. Acreage: 0.27 acres
    11. Pool: Yes
    12. Spa/HotTub: Yes
    13. Waterfront: No
    14. Year Built: 2020
    MLS#: O6372842
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Subdivision: Davis Shores
    5. Elementary School: Windermere Elem
    6. Middle School: Gotha Middle
    7. High School: Olympia High
    8. Provided by: CORCORAN PREMIER REALTY
    9. mfrmls
    10. DMCA Notice
    Welcome to 84 Oakdale Street, an exceptional luxury residence in the heart of Windermere, Florida, crafted by the renowned Element Home Buildersa rare opportunity to own one of their highly sought aft
    Listing Details and 51 Additional Pictures
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    119 Menendez Road
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    Details for 119 Menendez Road, ST AUGUSTINE, FL 32080
    Single Family
    1. Price: $649,000.00
    2. Price sqft: $354.65 / sqft
    3. Days On Market: 43
    4. Bedrooms: 4
    5. Baths: 2
    6. Garage / Parking Spaces: 1
    7. Bldg sqft: 1830
    8. Acreage: 0.20 acres
    9. Pool: Yes
    10. Spa/HotTub: Yes
    11. Waterfront: No
    12. Year Built: 1956
    MLS#: FC317277
    1. County: SAINT JOHNS
    2. City: ST AUGUSTINE
    3. Zipcode: 32080
    4. Subdivision: Davis Shores
    5. Elementary School: R. B. HUNT ELEMENTARY SCHOOL
    6. Middle School: SEBASTIAN MIDDLE SCHOOL
    7. High School: St. Augustine High School
    8. Provided by: ENDLESS SUMMER REALTY
    9. mfrmls
    10. DMCA Notice
    Turnkey, fully furnished island retreat in the heart of Davis Shores on Anastasia Islandjust under two miles to both Historic Downtown St. Augustine and the beach. Whether you're looking for a second
    Listing Details and 39 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.
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    Datafeed Last updated on May 10, 2026 @ 12:00 am
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