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  1. Subdivision Like Windsor Oaks
Details for 51 Mac Ewen Drive 14, OSPREY, FL 34229
Condominium
  1. Price: $350,000.00
  2. Price sqft: $588.24 / sqft
  3. Days On Market: 11
  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#: A4662898
  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 Elementary
  7. Middle School: Sarasota Middle
  8. High School: Venice Senior High
  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, all brand new, and is accessible by both
Details for 1661 Windsor Oak Court, KISSIMMEE, FL 34744
Townhome
  1. Price: $299,900.00
  2. Price sqft: $197.30 / sqft
  3. Previous Price: $307,000
  4. Last Price Change: 08/08/25
  5. Days On Market: 53
  6. Bedrooms: 3
  7. Baths: 3
  8. Bldg sqft: 1520
  9. Acreage: 0.02 acres
  10. Pool: No
  11. Community Pool: Yes
  12. Waterfront: No
  13. Year Built: 2000
MLS#: O6327343
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34744
  4. Subdivision: Windsor Oaks
  5. Elementary School: Mill Creek Elem (K 5)
  6. Middle School: Denn John Middle
  7. High School: Gateway High School (9 12)
  8. Provided by: BETTER HOMES AND GARDENS REAL ESTATE MANN GLOBAL P
  9. mfrmls
  10. DMCA Notice
Cozy well kept in gated community. Community pool. It is convenient to educational facilities and Valencia College. Double doors open the first floor bedroom or household office. Elegant pedestal sink
Details for 1645 Windsor Oak Court, Kissimmee, FL 34744
Townhome
  1. Price: $280,000.00
  2. Price sqft: $202.90 / sqft
  3. Previous Price: $289,000
  4. Last Price Change: 07/29/25
  5. Days On Market: 65
  6. Bedrooms: 3
  7. Baths: 3
  8. Bldg sqft: 1380
  9. Acreage: 0.02 acres
  10. Pool: Yes
  11. Community Pool: Yes
  12. Waterfront: No
  13. Year Built: 1999
MLS#: S5130196
  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: LPT REALTY, LLC
  9. Provided through
  10. DMCA Notice
Welcome to this beautifully maintained townhome in the heart of Kissimmee, located in the quiet, gated community of Windsor Oaks. This spacious 3 bedroom, 2.5 bath home features a rare and flexible la
Details for 1645 Windsor Oak Court, KISSIMMEE, FL 34744
Townhome
  1. Price: $280,000.00
  2. Price sqft: $202.90 / sqft
  3. Previous Price: $289,000
  4. Last Price Change: 09/04/25
  5. Days On Market: 65
  6. Bedrooms: 3
  7. Baths: 3
  8. Bldg sqft: 1380
  9. Acreage: 0.02 acres
  10. Pool: No
  11. Waterfront: No
  12. Year Built: 1999
MLS#: S5130196
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34744
  4. Subdivision: Windsor Oaks
  5. Elementary School: Mill Creek Elem (K 5)
  6. Middle School: Denn John Middle
  7. High School: Gateway High School (9 12)
  8. Provided by: LPT REALTY, LLC
  9. mfrmls
  10. DMCA Notice
Welcome to this beautifully maintained townhome in the heart of Kissimmee, located in the quiet, gated community of Windsor Oaks. This spacious 3 bedroom, 2.5 bath home features a rare and flexible la
Details for 1621 Emily Court, KISSIMMEE, FL 34744
Townhome
  1. Price: $278,900.00
  2. Price sqft: $212.41 / sqft
  3. Previous Price: $279,900
  4. Last Price Change: 09/03/25
  5. Days On Market: 126
  6. Bedrooms: 3
  7. Baths: 2
  8. Bldg sqft: 1313
  9. Acreage: 0.06 acres
  10. Pool: No
  11. Community Pool: Yes
  12. Waterfront: No
  13. Year Built: 1994
MLS#: O6305187
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34744
  4. Subdivision: Windsor Oaks
  5. Elementary School: Mill Creek Elem (K 5)
  6. Middle School: Denn John Middle
  7. High School: Gateway High School (9 12)
  8. Provided by: COLDWELL BANKER REALTY
  9. mfrmls
  10. DMCA Notice
Welcome Home! Stylish 3 Bedroom Villa Move In Ready with Investment Potential. seller motivated and will be doing a closing cost contribution of $8000, don't miss this opportunity, schedule the appoi
Details for 1603 Emily Court, KISSIMMEE, FL 34744
Townhome
  1. Price: $270,000.00
  2. Price sqft: $147.54 / sqft
  3. Previous Price: $278,000
  4. Last Price Change: 09/03/25
  5. Days On Market: 121
  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 Elem (K 5)
  6. Middle School: Denn John Middle
  7. High School: Gateway High School (9 12)
  8. Provided by: COLDWELL BANKER REALTY
  9. mfrmls
  10. DMCA Notice
Charming 3 bedroom, 2 bath home located in Kissimmee, near Hunters Creek and Buenaventura Lakes, across the street from Valencia Community College This well kept property features a bright living and
Details for 51 Mac Ewen Drive 1, OSPREY, FL 34229
Rental
  1. Price: $2,500.00
  2. Price sqft: $4.01 / sqft
  3. Previous Price: $3,200
  4. Last Price Change: 06/09/25
  5. Days On Market: 649
  6. Bedrooms: 1
  7. Baths: 1
  8. Bldg sqft: 623
  9. Acreage: 0.00 acres
  10. Pool: No
  11. Waterfront: No
  12. 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 NOVEMBER 2025 THRU JANUARY 2026*** Welcome to THE OAK community, it's gated 24/7. private as private can be. Drenched in value and a fantastic community located in South Sarasota. Open
Details for 1645 Windsor Oak Court, KISSIMMEE, FL 34744
Rental
  1. Price: $1,900.00
  2. Price sqft: $1.38 / sqft
  3. Previous Price: $2,000
  4. Last Price Change: 09/03/25
  5. Days On Market: 65
  6. Bedrooms: 3
  7. Baths: 3
  8. Bldg sqft: 1380
  9. Acreage: 0.02 acres
  10. Pool: No
  11. Waterfront: No
  12. Year Built: 1999
MLS#: S5130199
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34744
  4. Subdivision: Windsor Oaks
  5. Elementary School: Mill Creek Elem (K 5)
  6. Middle School: Denn John Middle
  7. High School: Gateway High School (9 12)
  8. Provided by: LPT REALTY, LLC
  9. mfrmls
  10. DMCA Notice
Looking for space, comfort, and convenience? Welcome to this charming 3 bedroom, 2.5 bath townhome in the gated community of Windsor Oaks. This home offers a spacious layout with two master suites, pe
Details for 1659 Windsor Oak Court, KISSIMMEE, FL 34744
Rental
  1. Price: $1,850.00
  2. Price sqft: $1.21 / sqft
  3. Previous Price: $1,900
  4. Last Price Change: 09/02/25
  5. Days On Market: 88
  6. Bedrooms: 3
  7. Baths: 3
  8. Bldg sqft: 1535
  9. Acreage: 0.02 acres
  10. Pool: No
  11. Community Pool: Yes
  12. Waterfront: No
  13. Year Built: 2000
MLS#: S5128804
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34744
  4. Subdivision: Windsor Oaks
  5. Elementary School: Mill Creek Elem (K 5)
  6. Middle School: Denn John Middle
  7. High School: Gateway High School (9 12)
  8. Provided by: LA ROSA REALTY LLC
  9. mfrmls
  10. DMCA Notice
FOR RENT: Spacious 3 Bedrooms, 2 Bathrooms Townhome centrally located in the gated Windsor Oaks community in Kissimmee. Kitchen is well equipped with all appliances and a breakfast bar located on the