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  1. School = Osceola High School
Details for 1886 Pleasant Hill Road, KISSIMMEE, FL 34746
Single Family
  1. Price: $2,500,000.00
  2. Price sqft: $2,136.75 / sqft
  3. Days On Market: 173
  4. Bedrooms: 3
  5. Baths: 2
  6. Bldg sqft: 1170
  7. Acreage: 10.87 acres
  8. Pool: No
  9. Waterfront: No
  10. Year Built: 1957
MLS#: S5128052
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34746
  4. Elementary School: Pleasant Hill Elem
  5. Middle School: Bellalago Charter Academy (K 8
  6. High School: Osceola High School
  7. Provided by: HOLISTIC REALTY FLORIDA, LLC
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  9. DMCA Notice
Description
  1. Prime Development Opportunity at 1886 Pleasant Hill Road, Kissimmee, FL 34746! The best time to secure an exceptional vacant land located in a rapidly growing area of Kissimmee. This expansive parcel
Details for 1501 Sunset Pointe Place, KISSIMMEE, FL 34744
Single Family
  1. Price: $1,599,000.00
  2. Price sqft: $266.06 / sqft
  3. Previous Price: $1,650,000
  4. Last Price Change: 11/06/25
  5. Days On Market: 321
  6. Bedrooms: 5
  7. Baths: 4
  8. Garage / Parking Spaces: 4
  9. Bldg sqft: 6010
  10. Acreage: 0.66 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Lake Privileges
  16. Year Built: 2000
MLS#: S5117808
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34744
  4. Subdivision: Sunset Pointe
  5. Elementary School: Partin Settlement Elem
  6. Middle School: Neptune Middle (6 8)
  7. High School: Osceola High School
  8. Provided by: PORTFOLIO REAL ESTATE GROUP
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Description
  1. Experience breathtaking florida lakefront sunsets from this stunning and unique custom home in the beautiful gated community of sunset pointe. Situated near shopping, disney/universal/sea world, major
Details for 1632 Regal Cove Court, KISSIMMEE, FL 34744
Single Family
  1. Price: $1,099,900.00
  2. Price sqft: $157.42 / sqft
  3. Previous Price: $1,144,900
  4. Last Price Change: 11/09/25
  5. Days On Market: 71
  6. Bedrooms: 6
  7. Baths: 6
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 6987
  10. Acreage: 0.49 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. Year Built: 1993
MLS#: S5134100
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34744
  4. Subdivision: Regal Cove
  5. Elementary School: Partin Settlement Elem
  6. Middle School: Neptune Middle (6 8)
  7. High School: Osceola High School
  8. Provided by: FIERCE REALTY
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Description
  1. Welcome to Regal Cove Modern Luxury Meets Country Charm! Imagine living in the exclusive, gated community of Regal Cove, where this fully renovated custom home offers both elegance and privacy. Set
Details for 111 Monument Avenue 801, KISSIMMEE, FL 34741
Condominium
  1. Price: $869,990.00
  2. Price sqft: $188.07 / sqft
  3. Previous Price: $924,990
  4. Last Price Change: 11/08/25
  5. Days On Market: 147
  6. Bedrooms: 4
  7. Baths: 3
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 4626
  10. Acreage: 0.00 acres
  11. Pool: No
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Lake Front
  15. Year Built: 2012
MLS#: O6320369
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34741
  4. Subdivision: Park View At City Centre Kiss
  5. Building: Park View At City Centre Kiss Residence Condo
  6. Elementary School: Central Avenue Elem
  7. Middle School: Denn John Middle
  8. High School: Osceola High School
  9. Provided by: KELLER WILLIAMS CLASSIC
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Description
  1. Penthouse perfection meets downtown renaissance discover the crown jewel of historic downtown kissimmee an architect designed penthouse that redefines luxury living in central florida's fastest grow
Details for 1395 Grandview Boulevard, KISSIMMEE, FL 34744
Single Family
  1. Price: $795,000.00
  2. Price sqft: $159.16 / sqft
  3. Days On Market: 23
  4. Bedrooms: 4
  5. Baths: 3
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 4995
  8. Acreage: 0.91 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 2003
MLS#: O6355952
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34744
  4. Subdivision: Regal Point
  5. Elementary School: Partin Settlement Elem
  6. Middle School: Neptune Middle (6 8)
  7. High School: Osceola High School
  8. Provided by: COLDWELL BANKER REALTY
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Description
  1. Tucked within the gates of Regal Point, one of Kissimmees most enchanting enclaves along the shores of Lake Toho, this custom built residence blends timeless craftsmanship with modern comfort. Set on
Details for 3020 Cardillino Way, KISSIMMEE, FL 34741
Single Family
  1. Price: $739,000.00
  2. Price sqft: $106.03 / sqft
  3. Days On Market: 41
  4. Bedrooms: 3
  5. Baths: 4
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 6970
  8. Acreage: 0.16 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2017
MLS#: S5136081
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34741
  4. Subdivision: Tapestry Ph 2
  5. Elementary School: Floral Ridge Elementary
  6. Middle School: Kissimmee Middle
  7. High School: Osceola High School
  8. Provided by: THE VALENZUELA REAL ESTATE GRO
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Description
  1. SELLER MOTIVATED! Stunning 3 bedroom, 3 bath fully furnished home located in the desirable gated community of Tapestry. This spacious two story corner home features a 3 car garage, a newly renovated E
Details for 2805 Carter Grove Lane, KISSIMMEE, FL 34741
Single Family
  1. Price: $710,000.00
  2. Price sqft: $174.32 / sqft
  3. Previous Price: $740,000
  4. Last Price Change: 11/15/25
  5. Days On Market: 42
  6. Bedrooms: 5
  7. Baths: 4
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 4073
  10. Acreage: 0.20 acres
  11. Pool: No
  12. Waterfront: No
  13. Year Built: 2014
MLS#: O6350502
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34741
  4. Subdivision: Preserve At Tapestry Ph 1
  5. Elementary School: Floral Ridge Elementary
  6. Middle School: Kissimmee Middle
  7. High School: Osceola High School
  8. Provided by: FLORIDA REALTY INVESTMENTS
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Description
  1. Welcome to this stunning move in ready home where thoughtful design, premium upgrades, and energy efficiency come together in perfect harmony. This beautifully maintained home offers the perfect balan
Details for 2518 Fontaine Drive, KISSIMMEE, FL 34741
Single Family
  1. Price: $693,900.00
  2. Price sqft: $170.32 / sqft
  3. Previous Price: $749,900
  4. Last Price Change: 11/04/25
  5. Days On Market: 544
  6. Bedrooms: 5
  7. Baths: 4
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 4074
  10. Acreage: 0.15 acres
  11. Pool: No
  12. Waterfront: No
  13. Year Built: 2017
MLS#: S5105586
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34741
  4. Subdivision: Tapestry
  5. Elementary School: Kissimmee Elem
  6. Middle School: Kissimmee Middle
  7. High School: Osceola High School
  8. Provided by: JAVI REALTY LLC
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  10. DMCA Notice
Description
  1. Welcome to my home in Tapestry, one of Kissimmees most desirable gated communities. This home was designed for families who love space, comfort, and privacy. The fully fenced backyard is ideal to safe
Details for 1455 Olympic Club Boulevard, CHAMPIONS GATE, FL 33896
Single Family
  1. Price: $680,000.00
  2. Price sqft: $140.64 / sqft
  3. Days On Market: 14
  4. Bedrooms: 5
  5. Baths: 5
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 4835
  8. Acreage: 0.28 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 2020
MLS#: O6357929
  1. County: POLK
  2. City: CHAMPIONS GATE
  3. Zipcode: 33896
  4. Subdivision: Stoneybrook South Tr K
  5. Elementary School: Four Corner Elem
  6. Middle School: West Side
  7. High School: Osceola High School
  8. Provided by: ROBERT SLACK LLC
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Description
  1. Motivated Seller! Only 20 minutes from Disney's iconic theme parks and all your favorite "Mickey approved" restaurants and shops! This immaculate 2020 build features a spacious 5 Bedroom layout with T
Details for 2321 Hinsdale Drive, KISSIMMEE, FL 34741
Single Family
  1. Price: $669,900.00
  2. Price sqft: $156.81 / sqft
  3. Days On Market: 402
  4. Bedrooms: 5
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4272
  8. Acreage: 0.21 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 2005
MLS#: S5113864
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34741
  4. Subdivision: Cypress Reserve Ph 02
  5. Elementary School: Kissimmee Elem
  6. Middle School: Kissimmee Middle
  7. High School: Osceola High School
  8. Provided by: DEAL MAKERS REALTY TEAM CORP
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Description
  1. This impressive 5 bedroom, 3.5 bathroom property is located in a prime location, offering both comfort and style. Upon entering, you are greeted by a spacious and bright layout with an open concept de
Wade M. Berlin