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1886 Pleasant Hill Road
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Details for 1886 Pleasant Hill Road, KISSIMMEE, FL 34746
Single Family
  1. Price: $1,650,000.00
  2. Price sqft: $1,410.26 / sqft
  3. Previous Price: $2,500,000
  4. Last Price Change: 03/30/26
  5. Days On Market: 527
  6. Bedrooms: 3
  7. Baths: 2
  8. Bldg sqft: 1170
  9. Acreage: 10.87 acres
  10. Pool: No
  11. Waterfront: No
  12. 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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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
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304 Lakeshore Boulevard
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Details for 304 Lakeshore Boulevard, KISSIMMEE, FL 34741
Multi-Family
  1. Price: $1,650,000.00
  2. Price sqft: $483.73 / sqft
  3. Days On Market: 174
  4. Bldg sqft: 3411
  5. Acreage: 0.18 acres
  6. Pool: No
  7. Waterfront: No
  8. Year Built: 1930
MLS#: O6408922
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34741
  4. Subdivision: Toliga Lake View
  5. Elementary School: Central Avenue Elem
  6. Middle School: Denn John Middle
  7. High School: Osceola High School
  8. Provided by: ROMAN'S PRO REALTY LLC
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Positioned along the storied shoreline of Lakeshore Boulevard, this rare income producing property and location captures the timeless character of Historic Downtown Kissimmee with an address that plac
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2260 John Anderson Drive
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Details for 2260 John Anderson Drive, ORMOND BEACH, FL 32176
Single Family
  1. Price: $999,000.00
  2. Price sqft: $319.88 / sqft
  3. Previous Price: $1,025,000
  4. Last Price Change: 09/27/26
  5. Days On Market: 588
  6. Bedrooms: 2
  7. Baths: 4
  8. Garage / Parking Spaces: 4
  9. Bldg sqft: 3123
  10. Acreage: 0.31 acres
  11. Pool: No
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Intracoastal Waterway,Riparian Rights,River Front
  15. Year Built: 1954
MLS#: FC308526
  1. County: VOLUSIA
  2. City: ORMOND BEACH
  3. Zipcode: 32176
  4. Elementary School: Osceola Elem
  5. Middle School: Ormond Beach Middle
  6. High School: Seabreeze High School
  7. Provided by: ONE SOTHEBYS INTERNATIONAL
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This charming retro ranch style home is perfectly situated on a prime waterfront lot along highly sought after John Anderson Drive, offering 125 feet of direct Intracoastal Waterway frontage with brea
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9014 Sunshine Ridge Loop
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Details for 9014 Sunshine Ridge Loop, KISSIMMEE, FL 34747
Single Family
  1. Price: $849,000.00
  2. Price sqft: $163.08 / sqft
  3. Previous Price: $889,000
  4. Last Price Change: 08/11/26
  5. Days On Market: 333
  6. Bedrooms: 9
  7. Baths: 7
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 5206
  10. Acreage: 0.16 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. Year Built: 2018
MLS#: O6366538
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34747
  4. Subdivision: Solara Residence
  5. Elementary School: Westside K 8
  6. Middle School: West Side
  7. High School: Osceola High School
  8. Provided by: LPT REALTY, LLC
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PRICE IMPROVEMENT!!! Stunning 9 Bedroom Vacation Home in Solara Resort Fully Upgraded & Turnkey Welcome to this exceptional 9 bedroom, 6.5 bathroom vacation retreat located in the highly desired S
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111 E Monument Avenue 801
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Details for 111 E Monument Avenue 801, KISSIMMEE, FL 34741
Condominium
  1. Price: $797,500.00
  2. Price sqft: $172.40 / sqft
  3. Previous Price: $925,000
  4. Last Price Change: 10/23/26
  5. Days On Market: 67
  6. Bedrooms: 4
  7. Baths: 3
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 4626
  10. Acreage: 0.17 acres
  11. Pool: No
  12. Waterfront: No
  13. Year Built: 2012
MLS#: S5156778
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34741
  4. Subdivision: City Centre Kissimmee Resident
  5. Building: City Centre Kissimmee Residential Condo Cb 12 Pg 1
  6. Elementary School: Central Avenue Elem
  7. Middle School: Denn John Middle
  8. High School: Osceola High School
  9. Provided by: ROYAL REALTY REAL ESTATE, LLC
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Experience one of a kind penthouse living in the heart of Downtown Kissimmee. This architect designed top floor residence offers 4 bedrooms, 3 full baths, 3,577 square feet under air, soaring 10 foot
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2518 Empress Drive
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Details for 2518 Empress Drive, KISSIMMEE, FL 34741
Single Family
  1. Price: $795,000.00
  2. Price sqft: $250.16 / sqft
  3. Previous Price: $850,000
  4. Last Price Change: 10/13/26
  5. Days On Market: 144
  6. Bedrooms: 4
  7. Baths: 3
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 3178
  10. Acreage: 0.19 acres
  11. Pool: Yes
  12. Community Pool: Yes
  13. Waterfront: No
  14. Year Built: 2020
MLS#: O6418213
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34741
  4. Subdivision: Tapestry Ph 5
  5. Elementary School: Floral Ridge Elementary
  6. Middle School: Kissimmee Middle
  7. High School: Osceola High School
  8. Provided by: CENTURY 21 BE3
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NEW PRICENOW OFFERED AT $795,000, A $55,000 REDUCTION. Exceptional outdoor living, contemporary style, and a resort inspired backyard define this extensively upgraded home in the gated community of Ta
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501 Sumner Street
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Details for 501 Sumner Street, KISSIMMEE, FL 34741
Single Family
  1. Price: $765,999.00
  2. Price sqft: $166.23 / sqft
  3. Days On Market: 131
  4. Bedrooms: 5
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4608
  8. Acreage: 0.20 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1926
MLS#: S5152826
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34741
  4. Subdivision: Oneal Osborns Add
  5. Elementary School: Central Avenue Elem
  6. Middle School: Denn John Middle
  7. High School: Osceola High School
  8. Provided by: KELLER WILLIAMS LEGACY REALTY
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FULLY REMODELED | NO HOA | PRIVATE IN LAW SUITE | IN GROUND POOL | PRIME IN CITY LOCATION Welcome to 501 W. Sumner St., a rare opportunity to own a beautifully remodeled, move in ready residence th
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2813 Bookmark Drive
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Details for 2813 Bookmark Drive, KISSIMMEE, FL 34746
Single Family
  1. Price: $700,000.00
  2. Price sqft: $206.61 / sqft
  3. Days On Market: 66
  4. Bedrooms: 5
  5. Baths: 5
  6. Garage / Parking Spaces: 1
  7. Bldg sqft: 3388
  8. Acreage: 0.11 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2020
MLS#: O6439221
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34746
  4. Subdivision: Cove At Storey Lake Ii
  5. Elementary School: Kissimmee Elem
  6. Middle School: Kissimmee Middle
  7. High School: Osceola High School
  8. Provided by: AXEN REALTY, LLC
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Welcome to this stunning 5 bedroom, 5 bathroom home, where comfort, style, and adventure come together in one exceptional property. Designed with both relaxation and entertaining in mind, this spaciou
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1559 Skyline Drive
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Details for 1559 Skyline Drive, KISSIMMEE, FL 34744
Single Family
  1. Price: $650,000.00
  2. Price sqft: $192.94 / sqft
  3. Days On Market: 44
  4. Bedrooms: 4
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3369
  8. Acreage: 0.34 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1989
MLS#: O6442242
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34744
  4. Subdivision: Harbour Oaks
  5. Elementary School: Partin Settlement Elem
  6. Middle School: Neptune Middle (6 8)
  7. High School: Osceola High School
  8. Provided by: NORKIS & CO REALTY
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RARE FINANCING OPPORTUNITY EXISTING FHA MORTGAGE AT 2.75% MAY BE ASSUMABLE! Welcome to 1559 Skyline Drive, located in the desirable Harbour Oaks community of Kissimmee! This spacious 4 bedroom, 3 bat
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1714 Cheryl Lane
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Details for 1714 Cheryl Lane, KISSIMMEE, FL 34744
Single Family
  1. Price: $650,000.00
  2. Price sqft: $128.94 / sqft
  3. Previous Price: $674,900
  4. Last Price Change: 09/29/26
  5. Days On Market: 219
  6. Bedrooms: 4
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 5041
  10. Acreage: 0.45 acres
  11. Pool: No
  12. Waterfront: No
  13. Year Built: 1989
MLS#: O6395426
  1. County: OSCEOLA
  2. City: KISSIMMEE
  3. Zipcode: 34744
  4. Subdivision: Regal Oak Shores
  5. Elementary School: Partin Settlement Elem
  6. Middle School: Neptune Middle (6 8)
  7. High School: Osceola High School
  8. Provided by: EXP REALTY LLC
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Virtually Staged. Positioned on an expansive 0.45 acre lot with no HOA in Kissimmee, this custom built residence delivers space, privacy, and elevated finishes rarely found at this price point. Inside
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