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Details for 1638 Windsor Oak Court, KISSIMMEE, FL 34744
Townhome
  1. Price: $284,900.00
  2. Price sqft: $191.21 / sqft
  3. Previous Price: $295,000
  4. Last Price Change: 12/15/25
  5. Days On Market: 130
  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#: S5133782
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34744
  4. Subdivision: Windsor Oaks
  5. Provided by: PREFERRED REAL ESTATE BROKERS
  6. mfrmls
  7. DMCA Notice
Seller is motivated and open to reasonable offers on this upgraded 3 bedroom townhome.Whether you live here year round or use it as your Florida escape, this property offers the best of both worlds, p
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: 251
  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
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 1647 Windsor Oak Court, KISSIMMEE, FL 34744
Townhome
  1. Price: $255,000.00
  2. Price sqft: $171.14 / sqft
  3. Previous Price: $260,000
  4. Last Price Change: 12/12/25
  5. Days On Market: 107
  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
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: 779
  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 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 1657 Windsor Oak Court, KISSIMMEE, FL 34744
Rental
  1. Price: $1,875.00
  2. Price sqft: $1.24 / sqft
  3. Previous Price: $1,900
  4. Last Price Change: 11/19/25
  5. Days On Market: 77
  6. Bedrooms: 3
  7. Baths: 3
  8. Bldg sqft: 1516
  9. Acreage: 0.02 acres
  10. Pool: No
  11. Community Pool: Yes
  12. Waterfront: No
  13. Year Built: 2000
MLS#: S5137580
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34744
  4. Subdivision: Windsor Oaks
  5. Provided by: ACKLEY FLORIDA PROPERTY MANAGEMENT INC
  6. mfrmls
  7. DMCA Notice
Lovely townhome for rent in the heart of Kissimmee! Features three bedrooms, two and a half baths in gated Windsor Oaks. Open floor plan, one bedroom on 1st floor, two main suites on 2nd floor. Open k
Details for 1645 Windsor Oak Court, KISSIMMEE, FL 34744
Rental
  1. Price: $1,850.00
  2. Price sqft: $1.34 / sqft
  3. Previous Price: $1,900
  4. Last Price Change: 12/23/25
  5. Days On Market: 195
  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
  6. Middle School: Denn John
  7. High School: Gateway
  8. Provided by: LPT REALTY, LLC
  9. mfrmls
  10. DMCA Notice
BRAND NEW FLOORING CABLE & INTERNET INCLUDED!! 3 bedroom, 2.5 bath townhome located in the gated community of Windsor Oaks, featuring brand new flooring and cable and internet included in the rent. T
Details for 1659 Windsor Oak Court, KISSIMMEE, FL 34744
Rental
  1. Price: $1,750.00
  2. Price sqft: $1.14 / sqft
  3. Previous Price: $1,800
  4. Last Price Change: 12/13/25
  5. Days On Market: 217
  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
  6. Middle School: Denn John
  7. High School: Gateway
  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