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  1. Subdivision Like Chelsea Square 1
  2. Listing Status = Active
3227 Chesswood Avenue
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Details for 3227 Chesswood Avenue, KISSIMMEE, FL 34741
Townhome
  1. Price: $219,000.00
  2. Price sqft: $204.29 / sqft
  3. Previous Price: $210,000
  4. Last Price Change: 10/26/26
  5. Days On Market: 47
  6. Bedrooms: 3
  7. Baths: 2
  8. Bldg sqft: 1072
  9. Acreage: 0.03 acres
  10. Pool: No
  11. Community Pool: Yes
  12. Waterfront: No
  13. Year Built: 1986
MLS#: O6441475
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34741
  4. Subdivision: Chelsea Square 5b
  5. Elementary School: Kissimmee Elem
  6. Middle School: Kissimmee Middle
  7. High School: Osceola High School
  8. Provided by: RE/MAX PRIME PROPERTIES
  9. mfrmls
  10. DMCA Notice
WELCOME HOME! LOW HOA! Seller offering $10,000 to Buyer for closing costs or renovations. This beautifully positioned 3 bedroom, 2 full bath end unit townhome in Chelsea Square is READY NOW and offer
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1947 Bentley Boulevard
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Details for 1947 Bentley Boulevard, KISSIMMEE, FL 34741
Townhome
  1. Price: $215,901.00
  2. Price sqft: $201.40 / sqft
  3. Previous Price: $224,901
  4. Last Price Change: 10/09/26
  5. Days On Market: 185
  6. Bedrooms: 3
  7. Baths: 2
  8. Bldg sqft: 1072
  9. Acreage: 0.03 acres
  10. Pool: No
  11. Community Pool: Yes
  12. Waterfront: No
  13. Year Built: 1985
MLS#: S5148951
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34741
  4. Subdivision: Chelsea Square 4a
  5. Provided by: CENTURY 21 ALL HOMES & PROPERT
  6. mfrmls
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Virtually Staged. Step into this beautifully updated 3 bedroom, 2 bath corner unit, thoughtfully upgraded for comfort and style. The home features brand new luxury vinyl flooring throughout the living
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3220 Hempstead Avenue
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Details for 3220 Hempstead Avenue, KISSIMMEE, FL 34741
Townhome
  1. Price: $204,900.00
  2. Price sqft: $218.91 / sqft
  3. Days On Market: 9
  4. Bedrooms: 2
  5. Baths: 2
  6. Bldg sqft: 936
  7. Acreage: 0.03 acres
  8. Pool: No
  9. Waterfront: No
  10. Year Built: 1984
MLS#: S5160540
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34741
  4. Subdivision: Chelsea Square 3
  5. Provided by: LA CASA LUXE REALTY
  6. mfrmls
  7. DMCA Notice
Under contract accepting backup offers. Welcome to this charming 2 bedroom, 2 bathroom townhouse conveniently located in the heart of Kissimmee! Enjoy easy access to everyday essentials, including Pub
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Address Not Provided
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Townhome
  1. Price: $199,900.00
  2. Price sqft: $201.51 / sqft
  3. Previous Price: $204,900
  4. Last Price Change: 10/15/26
  5. Days On Market: 80
  6. Bedrooms: 2
  7. Baths: 2
  8. Bldg sqft: 992
  9. Acreage: 0.02 acres
  10. Pool: No
  11. Waterfront: No
  12. Year Built: 1983
MLS#: S5156039
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34741
  4. Subdivision: Chelsea Square 1
  5. Provided by: LA CASA LUXE REALTY
  6. mfrmls
  7. DMCA Notice
Welcome to this charming 2 bedroom, 1.5 bath townhome in the heart of just minutes close to shopping center like The Loop, gym, dining, and entertainment, with Disney, Universal and MCO Orlando airpor
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3117 Windover Avenue
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Details for 3117 Windover Avenue, KISSIMMEE, FL 34741
Rental
  1. Price: $1,790.00
  2. Price sqft: $1.80 / sqft
  3. Previous Price: $1,795
  4. Last Price Change: 11/03/26
  5. Days On Market: 45
  6. Bedrooms: 2
  7. Baths: 2
  8. Bldg sqft: 992
  9. Acreage: 0.02 acres
  10. Pool: No
  11. Waterfront: No
  12. Year Built: 1983
MLS#: O6444411
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34741
  4. Subdivision: Chelsea Square 1
  5. Elementary School: Kissimmee Elem
  6. Middle School: Kissimmee Middle
  7. High School: Osceola High School
  8. Provided by: VELOCITY
  9. mfrmls
  10. DMCA Notice
FULLY RENOVATED Townhouse near Shingle Creek!! Well located 2 bedroom, 1.5 bath townhome offering about 992 square feet of living space in the Chelsea Square community. The two story layout separates
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Address Not Provided
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Rental
  1. Price: $1,600.00
  2. Price sqft: $1.49 / sqft
  3. Previous Price: $1,650
  4. Last Price Change: 10/24/25
  5. Days On Market: 466
  6. Bedrooms: 3
  7. Baths: 2
  8. Bldg sqft: 1076
  9. Acreage: 0.03 acres
  10. Pool: No
  11. Community Pool: Yes
  12. Waterfront: No
  13. Year Built: 1985
MLS#: O6332145
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34741
  4. Subdivision: Chelsea Square 4a
  5. Provided by: ROVIRA PROPERTY MANAGEMENT LLC
  6. mfrmls
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NO SECURITY DEPOSIT REQUIRED FOR SELECTED QUALIFIED CANDIDATES Charming 3 bedroom, 2 bathroom villa located just minutes from Vine and John Young, with convenient access to public transportation. T
Listing Details and 14 Additional Pictures
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3120 E Tower Court
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Details for 3120 E Tower Court, KISSIMMEE, FL 34741
Rental
  1. Price: $1,575.00
  2. Price sqft: $1.35 / sqft
  3. Days On Market: 24
  4. Bedrooms: 2
  5. Baths: 2
  6. Bldg sqft: 1170
  7. Acreage: 0.03 acres
  8. Pool: No
  9. Waterfront: No
  10. Year Built: 1985
MLS#: S5159679
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34741
  4. Subdivision: Chelsea Square 04b
  5. Building: Chelsea Square 04b
  6. Elementary School: Kissimmee Elem
  7. Middle School: Kissimmee Middle
  8. High School: Osceola High School
  9. Provided by: GPS PROPERTY GROUP INC.
  10. mfrmls
  11. DMCA Notice
FOR RENT $1,575 PER MONTH! AVAILABLE NOVEMBER 1, 2026! Great rental opportunity in the heart of Kissimmee! This 2 bedroom, 2 bathroom property offers 864 square feet of living space with a comfortabl
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3254 Chesswood Avenue
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Details for 3254 Chesswood Avenue, KISSIMMEE, FL 34741
Rental
  1. Price: $1,450.00
  2. Price sqft: $1.68 / sqft
  3. Previous Price: $1,650
  4. Last Price Change: 10/13/26
  5. Days On Market: 63
  6. Bedrooms: 2
  7. Baths: 2
  8. Bldg sqft: 864
  9. Acreage: 0.03 acres
  10. Pool: No
  11. Waterfront: No
  12. Year Built: 1986
MLS#: S5157118
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34741
  4. Subdivision: Chelsea Square 5b
  5. Provided by: FLORIDA FANTASY REAL ESTATE INC
  6. mfrmls
  7. DMCA Notice
Welcome to this charming 2 bedroom, 2 bathroom villa located in the desirable Chelsea Square community in Kissimmee. This cozy one story home offers approximately 864 square feet of comfortable living
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