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  1. Subdivision Like Windsor Hill
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9621 Windy Ridge Road
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Details for 9621 Windy Ridge Road, WINDERMERE, FL 34786
Single Family
  1. Price: $6,750,000.00
  2. Price sqft: $246.06 / sqft
  3. Previous Price: $6,999,999
  4. Last Price Change: 11/03/26
  5. Days On Market: 18
  6. Bedrooms: 9
  7. Baths: 16
  8. Bldg sqft: 27432
  9. Acreage: 2.50 acres
  10. Pool: Yes
  11. Waterfront: No
  12. Year Built: 2025
MLS#: O6451612
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windsor Hill
  5. Provided by: CITARELLI REALTY GROUP LLC
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Under Construction. Cant beat the location and land in this area is scarce !!!AS IS ....Great piece of land with the best location with main exterior done !!!!
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9615 Windy Ridge Road
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Details for 9615 Windy Ridge Road, WINDERMERE, FL 34786
Single Family
  1. Price: $5,300,000.00
  2. Price sqft: $388.05 / sqft
  3. Days On Market: 25
  4. Bedrooms: 6
  5. Baths: 8
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 13658
  8. Acreage: 2.49 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2007
MLS#: O6449197
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windsor Hill
  5. Elementary School: Thornebrooke Elem
  6. Middle School: Gotha Middle
  7. High School: Olympia High
  8. Provided by: KELLER WILLIAMS CLASSIC
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Under contract accepting backup offers. A palm framed pool and spa, a balcony connected game room and a dedicated theater give this Mediterranean inspired estate a distinctive rhythm of outdoor relaxa
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9548 Crown Prince Lane
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Details for 9548 Crown Prince Lane, WINDERMERE, FL 34786
Single Family
  1. Price: $1,395,000.00
  2. Price sqft: $260.12 / sqft
  3. Previous Price: $1,450,000
  4. Last Price Change: 11/05/26
  5. Days On Market: 178
  6. Bedrooms: 4
  7. Baths: 4
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 5363
  10. Acreage: 0.48 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 1999
MLS#: O6407352
  1. County: ORANGE
  2. City: WINDERMERE
  3. Zipcode: 34786
  4. Subdivision: Windsor Hill
  5. Elementary School: Thornebrooke Elem
  6. Middle School: Gotha Middle
  7. High School: Olympia High
  8. Provided by: DOUGLAS ELLIMAN
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Under contract accepting backup offers. Virtually Staged. Nestled on a rare half acre lot in one of Windermeres most sought after communities, Windsor Hills, this FULLY RENOVATED luxury home delivers
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2624 Bowring Street
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Details for 2624 Bowring Street, KISSIMMEE, FL 34747
Single Family
  1. Price: $729,000.00
  2. Price sqft: $201.83 / sqft
  3. Previous Price: $719,000
  4. Last Price Change: 11/04/26
  5. Days On Market: 19
  6. Bedrooms: 6
  7. Baths: 4
  8. Bldg sqft: 3612
  9. Acreage: 0.23 acres
  10. Pool: Yes
  11. Spa/HotTub: Yes
  12. Waterfront: No
  13. Year Built: 2007
MLS#: O6451359
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34747
  4. Subdivision: Windsor Hills
  5. Provided by: HOLIDAY REALTY LLC
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Welcome to this exceptional 6 bedroom, 4 bathroom vacation home located in the highly sought after Windsor Hills Resort, one of the closest vacation rental communities to Walt Disney World! Being sold
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2536 Holtrock Street
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Details for 2536 Holtrock Street, KISSIMMEE, FL 34747
Single Family
  1. Price: $698,000.00
  2. Price sqft: $195.63 / sqft
  3. Days On Market: 88
  4. Bedrooms: 6
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3568
  8. Acreage: 0.20 acres
  9. Pool: Yes
  10. Community Pool: Yes
  11. Spa/HotTub: Yes
  12. Waterfront: No
  13. Year Built: 2008
MLS#: O6432734
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34747
  4. Subdivision: Windsor Hills Ph 7
  5. Provided by: RATIO REAL ESTATE, LLC
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Welcome to your ultimate vacation retreat, ideally located just 5 miles from Walt Disney World in the highly sought after Windsor Hills Resort! This beautifully maintained 6 bedroom, 4 bathroom pool h
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2564 Archfeld Boulevard
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Details for 2564 Archfeld Boulevard, KISSIMMEE, FL 34747
Single Family
  1. Price: $695,000.00
  2. Price sqft: $192.41 / sqft
  3. Days On Market: 8
  4. Bedrooms: 6
  5. Baths: 4
  6. Bldg sqft: 3612
  7. Acreage: 0.21 acres
  8. Pool: Yes
  9. Spa/HotTub: Yes
  10. Waterfront: No
  11. Year Built: 2008
MLS#: G5119211
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34747
  4. Subdivision: Windsor Hills Ph 7
  5. Provided by: OLYMPUS EXECUTIVE REALTY INC
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This is a tastefully furnished six bedroom 4 bathroom home with a South West facing pool and spa, it is also a turnkey short term rental property on Windsor Hills 4 miles from Disney Parks. Margaritav
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2669 Manesty Lane
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Details for 2669 Manesty Lane, KISSIMMEE, FL 34747
Single Family
  1. Price: $678,000.00
  2. Price sqft: $191.09 / sqft
  3. Days On Market: 16
  4. Bedrooms: 6
  5. Baths: 4
  6. Bldg sqft: 3548
  7. Acreage: 0.33 acres
  8. Pool: Yes
  9. Spa/HotTub: Yes
  10. Waterfront: No
  11. Year Built: 2006
MLS#: O6452471
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34747
  4. Subdivision: Windsor Hills Ph 3
  5. Provided by: RATIO REAL ESTATE, LLC
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Welcome to your ultimate vacation retreatideally situated just 5 miles from the world renowned Walt Disney World! This stunning 6 bedroom, 4 bathroom home sits on an elevated premium corner lot in the
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7743 Comrow Street
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Details for 7743 Comrow Street, KISSIMMEE, FL 34747
Single Family
  1. Price: $675,000.00
  2. Price sqft: $266.17 / sqft
  3. Previous Price: $615,000
  4. Last Price Change: 10/12/26
  5. Days On Market: 151
  6. Bedrooms: 4
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 2536
  10. Acreage: 0.14 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. Year Built: 2004
MLS#: S5151580
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34747
  4. Subdivision: Windsor Hills Ph 1
  5. High School: Celebration High
  6. Provided by: REAL BROKER, LLC
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Welcome to this exceptional turnkey vacation rental opportunity in the highly sought after Windsor Hills Resort! This fully furnished 4 bedroom, 4 bath home is designed to entertain guests of all ages
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7765 Tosteth Street
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Details for 7765 Tosteth Street, KISSIMMEE, FL 34747
Single Family
  1. Price: $659,000.00
  2. Price sqft: $182.45 / sqft
  3. Previous Price: $699,000
  4. Last Price Change: 10/13/26
  5. Days On Market: 119
  6. Bedrooms: 6
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 3612
  10. Acreage: 0.14 acres
  11. Pool: Yes
  12. Community Pool: Yes
  13. Spa/HotTub: Yes
  14. Waterfront: No
  15. Year Built: 2005
MLS#: O6423586
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34747
  4. Subdivision: Windsor Hills Ph 3
  5. Elementary School: Westside K 8
  6. Middle School: West Side
  7. High School: Celebration High
  8. Provided by: FLORIDA 360 REALTY LLC
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Welcome to 7765 Tosteth Street, a beautifully appointed vacation home in the heart of Windsor Hills Resort Orlando's premier gated short term rental community, just minutes from Walt Disney World. T
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2623 Pawnall Street
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Details for 2623 Pawnall Street, KISSIMMEE, FL 34747
Single Family
  1. Price: $655,000.00
  2. Price sqft: $181.34 / sqft
  3. Previous Price: $670,000
  4. Last Price Change: 10/29/26
  5. Days On Market: 136
  6. Bedrooms: 6
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 3612
  10. Acreage: 0.15 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. Year Built: 2007
MLS#: O6419768
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34747
  4. Subdivision: Windsor Hills Ph 6
  5. Provided by: EXP REALTY LLC
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Busy rental! Minutes to Animal Kingdom! Guest friendly, fun, and full of upgrades! This vacation home has been thoughtfully improved with themed spaces throughout, including a fully themed garage/ga
Listing Details and 25 Additional Pictures
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