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    1. Subdivision Like Windsor Oaks
    2. Listing Status = Active
    51 Macewen Drive 5
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    Details for 51 Macewen Drive 5, OSPREY, FL 34229
    Condominium
    1. Price: $300,000.00
    2. Price sqft: $444.44 / sqft
    3. Days On Market: 19
    4. Bedrooms: 1
    5. Baths: 1
    6. Bldg sqft: 675
    7. Acreage: 4.53 acres
    8. Pool: No
    9. Waterfront: Yes
    10. Wateraccess: Yes
    11. Waterfront Type: Lake Front
    12. Year Built: 1990
    MLS#: A4689838
    1. County: SARASOTA
    2. City: OSPREY
    3. Zipcode: 34229
    4. Subdivision: Windsor Lodge At The Oaks
    5. Building: Windsor Lodge At The Oaks
    6. Elementary School: Laurel Nokomis
    7. Middle School: Sarasota
    8. High School: Pine View
    9. Provided by: 342 REAL ESTATE
    10. mfrmls
    11. DMCA Notice
    Discover a rare opportunity to own a serene retreat in The Oaks, one of Sarasotas most sought after private golf and country club communities. This bright, beautifully updated ground floor studio is o
    Listing Details and 43 Additional Pictures
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    51 Mac Ewen Drive 14
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    Details for 51 Mac Ewen Drive 14, OSPREY, FL 34229
    Condominium
    1. Price: $285,000.00
    2. Price sqft: $478.99 / sqft
    3. Days On Market: 19
    4. Bedrooms: 1
    5. Baths: 1
    6. Bldg sqft: 595
    7. Acreage: 0.00 acres
    8. Pool: No
    9. Community Pool: Yes
    10. Waterfront: No
    11. Year Built: 1990
    MLS#: A4690371
    1. County: SARASOTA
    2. City: OSPREY
    3. Zipcode: 34229
    4. Subdivision: Windsor Lodge At The Oaks
    5. Building: Windsor Lodge At The Oaks
    6. Elementary School: Laurel Nokomis
    7. Middle School: Sarasota
    8. High School: Venice Senior
    9. Provided by: COLDWELL BANKER REALTY
    10. mfrmls
    11. DMCA Notice
    This completely updated 595 sq ft second floor condominium is located in the Windsor Lodge behind the gates of The Oaks. It features top of the line finishes and is accessible by both elevator and sta
    Listing Details and 18 Additional Pictures
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    1624 Windsor Oak Court
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    Details for 1624 Windsor Oak Court, KISSIMMEE, FL 34744
    Townhome
    1. Price: $264,900.00
    2. Price sqft: $177.79 / sqft
    3. Days On Market: 12
    4. Bedrooms: 3
    5. Baths: 3
    6. Bldg sqft: 1490
    7. Acreage: 0.02 acres
    8. Pool: No
    9. Community Pool: Yes
    10. Waterfront: No
    11. Year Built: 1998
    MLS#: O6402513
    1. County: OSCEOLA
    2. City: KISSIMMEE
    3. Zipcode: 34744
    4. Subdivision: Windsor Oaks
    5. Provided by: CHARLES RUTENBERG REALTY ORLANDO
    6. mfrmls
    7. DMCA Notice
    Welcome to your new home! This fantastic 2 story townhome is located in a conveniently situated gated community in Kissimmee. Featuring 2 spacious bedrooms upstairs with 2.5 baths, den on the 1st flo
    Listing Details and 52 Additional Pictures
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    1603 Emily Court
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    Details for 1603 Emily Court, KISSIMMEE, FL 34744
    Townhome
    1. Price: $259,900.00
    2. Price sqft: $142.02 / sqft
    3. Previous Price: $269,900
    4. Last Price Change: 01/05/26
    5. Days On Market: 366
    6. Bedrooms: 3
    7. Baths: 2
    8. Bldg sqft: 1830
    9. Acreage: 0.04 acres
    10. Pool: No
    11. Waterfront: No
    12. Year Built: 1997
    MLS#: O6307235
    1. County: OSCEOLA
    2. City: KISSIMMEE
    3. Zipcode: 34744
    4. Subdivision: Windsor Oaks
    5. Elementary School: Mill Creek
    6. Middle School: Denn John
    7. High School: Gateway
    8. Provided by: COLDWELL BANKER REALTY
    9. mfrmls
    10. DMCA Notice
    The property is back on the market after the previous buyers financing did not move forward. All inspections were completed and the home is ready for a new qualified buyer. We welcome showings and new
    Listing Details and 23 Additional Pictures
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    1647 Windsor Oak Court
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    Details for 1647 Windsor Oak Court, KISSIMMEE, FL 34744
    Townhome
    1. Price: $245,000.00
    2. Price sqft: $164.43 / sqft
    3. Previous Price: $247,000
    4. Last Price Change: 03/27/26
    5. Days On Market: 222
    6. Bedrooms: 3
    7. Baths: 3
    8. Bldg sqft: 1490
    9. Acreage: 0.02 acres
    10. Pool: No
    11. Community Pool: Yes
    12. Waterfront: No
    13. Year Built: 1999
    MLS#: S5134784
    1. County: OSCEOLA
    2. City: KISSIMMEE
    3. Zipcode: 34744
    4. Subdivision: Windsor Oaks
    5. Elementary School: Mill Creek
    6. Middle School: Denn John
    7. High School: Gateway
    8. Provided by: ADVISERS REALTY & MANAGEMENT
    9. mfrmls
    10. DMCA Notice
    This townhome is located in a gated community with a community pool. The open kitchen connects seamlessly to the spacious living room, complemented by a rear screened porch. Upon entering, you'll find
    Listing Details and 23 Additional Pictures
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    51 Macewen Drive 11
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    Details for 51 Macewen Drive 11, OSPREY, FL 34229
    Condominium
    1. Price: $235,000.00
    2. Price sqft: $347.12 / sqft
    3. Previous Price: $275,000
    4. Last Price Change: 05/01/26
    5. Days On Market: 106
    6. Bedrooms: 1
    7. Baths: 1
    8. Bldg sqft: 677
    9. Acreage: 0.00 acres
    10. Pool: No
    11. Waterfront: Yes
    12. Wateraccess: Yes
    13. Waterfront Type: Lake Front
    14. Year Built: 1990
    MLS#: A4679180
    1. County: SARASOTA
    2. City: OSPREY
    3. Zipcode: 34229
    4. Subdivision: Windsor Lodge At The Oaks
    5. Building: Windsor Lodge At The Oaks
    6. Elementary School: Laurel Nokomis
    7. Middle School: Sarasota
    8. High School: Venice Senior
    9. Provided by: 342 REAL ESTATE
    10. mfrmls
    11. DMCA Notice
    Withing the prestigious The Oaks Golf and Country Club, at the Windsor Lodge, this second floor, maintenance free, lakeside efficiency features a covered balcony with views of the lake, pool, and golf
    Listing Details and 41 Additional Pictures
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    51 Mac Ewen Drive 1
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    Details for 51 Mac Ewen Drive 1, OSPREY, FL 34229
    Rental
    1. Price: $2,500.00
    2. Price sqft: $4.01 / sqft
    3. Days On Market: 894
    4. Bedrooms: 1
    5. Baths: 1
    6. Bldg sqft: 623
    7. Acreage: 0.00 acres
    8. Pool: No
    9. Waterfront: No
    10. Year Built: 1990
    MLS#: A4589608
    1. County: SARASOTA
    2. City: OSPREY
    3. Zipcode: 34229
    4. Subdivision: Windsor Lodge At The Oaks
    5. Building: Windsor Lodge At The Oaks
    6. Provided by: AUDREY RAIN RENTALS, INC
    7. mfrmls
    8. DMCA Notice
    ***AVAILABLE MAY 2026 THRU JULY 2026 AND THEN AGAIN IN NOVEMBER 2026*** Welcome to THE OAK community, it's gated 24/7. private as private can be. Drenched in value and a fantastic community located i
    Listing Details and 9 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 9, 2026 @ 12:00 am
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