Searching on:
  1. Subdivision Like Osceola
  2. Listing Status = Active
Details for 550 Palmer Avenue, WINTER PARK, FL 32789
Single Family
  1. Price: $6,895,000.00
  2. Price sqft: $861.66 / sqft
  3. Previous Price: $7,200,000
  4. Last Price Change: 01/07/26
  5. Days On Market: 145
  6. Bedrooms: 5
  7. Baths: 7
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 8002
  10. Acreage: 0.48 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. Year Built: 2025
MLS#: O6349188
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Osceola Place
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: FANNIE HILLMAN & ASSOCIATES
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Exquisite new construction in the Heart of Winter Park perfectly positioned on an oversized lot just steps from Park Avenues renowned shops, fine dining, and the iconic Winter Park 9 hole golf course,
Details for 234 Detmar Drive, WINTER PARK, FL 32789
Single Family
  1. Price: $1,695,000.00
  2. Price sqft: $395.94 / sqft
  3. Days On Market: 34
  4. Bedrooms: 5
  5. Baths: 6
  6. Garage / Parking Spaces: 1
  7. Bldg sqft: 4281
  8. Acreage: 0.42 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1935
MLS#: O6379927
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Osceola Shores Sec 1
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: FANNIE HILLMAN & ASSOCIATES
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Nestled behind gates in the heart of Winter park, this enchanting 1930's residence blends historic charm with many recent upgrades. The beautifully renovated kitchen anchors the home, while the downst
Details for 446 Alberta Drive, WINTER PARK, FL 32789
Single Family
  1. Price: $1,675,000.00
  2. Price sqft: $410.94 / sqft
  3. Previous Price: $1,750,000
  4. Last Price Change: 02/06/26
  5. Days On Market: 270
  6. Bedrooms: 4
  7. Baths: 3
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 4076
  10. Acreage: 0.35 acres
  11. Pool: No
  12. Waterfront: No
  13. Year Built: 1968
MLS#: O6319233
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Osceola Summit
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: CHARLES RUTENBERG REALTY ORLANDO
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Charming Opportunity in Prime Winter Park 446 Alberta Drive, Winter Park, FL! First time ever on the market and sits on a double lot that is .35 acres. Only a mile stroll to the famous Park Ave sho
Details for 340 Alberta Drive, WINTER PARK, FL 32789
Single Family
  1. Price: $1,545,000.00
  2. Price sqft: $377.57 / sqft
  3. Previous Price: $1,598,000
  4. Last Price Change: 12/23/25
  5. Days On Market: 178
  6. Bedrooms: 4
  7. Baths: 4
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 4092
  10. Acreage: 0.30 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. Year Built: 2000
MLS#: O6345231
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Osceola Summit
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: REAL ESTATE FIRM OF ORLANDO
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Welcome to 340 Alberta Drive, a beautifully maintained 4 bedroom, 4 bath residence with a new roof installed in 2020. Situated on a spacious .30 acre lot in the heart of Winter Park, this home feature
Details for 1870 Walker Avenue, WINTER PARK, FL 32789
Single Family
  1. Price: $1,425,000.00
  2. Price sqft: $570.00 / sqft
  3. Days On Market: 3
  4. Bedrooms: 3
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 2500
  8. Acreage: 0.15 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 1930
MLS#: O6390504
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Osceola Heights
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: PREMIER SOTHEBY'S INTL. REALTY
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This brand new residence, thoughtfully designed by Michael Wenrich, captures the timeless elegance and refined simplicity reminiscent of the iconic coastal architecture of Alys Beach. Clean architectu
Details for 6007 Central Avenue, TAMPA, FL 33604
Single Family
  1. Price: $675,000.00
  2. Price sqft: $524.88 / sqft
  3. Days On Market: 31
  4. Bedrooms: 2
  5. Baths: 2
  6. Garage / Parking Spaces: 1
  7. Bldg sqft: 1286
  8. Acreage: 0.16 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 1942
MLS#: TB8476266
  1. County: HILLSBOROUGH
  2. City: TAMPA
  3. Zipcode: 33604
  4. Subdivision: Osceola
  5. Provided by: JACK KELLER INC
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This is a must see, a top notch, workmanship home, located in historic Seminole Heights. Very close to schools, Churches, and shopping.
Details for 920 20th Street, GAINESVILLE, FL 32603
Single Family
  1. Price: $595,000.00
  2. Price sqft: $255.58 / sqft
  3. Days On Market: 46
  4. Bedrooms: 5
  5. Baths: 2
  6. Garage / Parking Spaces: 1
  7. Bldg sqft: 2328
  8. Acreage: 0.87 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 1948
MLS#: GC537023
  1. County: ALACHUA
  2. City: GAINESVILLE
  3. Zipcode: 32603
  4. Subdivision: Osceola Heights
  5. Provided by: CORNERSTONE REALTY & MANAGEMENT SERVICES LLC
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Prime UF Location | Flexible Layout | Creekfront Privacy Spacious 3 bedroom, 1 bath home just minutes from the University of Florida, offering exceptional flexibility and income potential. The main r
Details for 350 Osceola Avenue 5, ORLANDO, FL 32801
Condominium
  1. Price: $575,000.00
  2. Price sqft: $339.03 / sqft
  3. Days On Market: 24
  4. Bedrooms: 2
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 1696
  8. Acreage: 0.01 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 2005
MLS#: O6384416
  1. County: ORANGE
  2. City: ORLANDO
  3. Zipcode: 32801
  4. Subdivision: Osceola Brownstones
  5. Building: Osceola Brownstones
  6. Provided by: CHARLES RUTENBERG REALTY ORLANDO
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This gorgeous three story Osceola Brownstones condo offers 2 bedrooms, 2.5 baths, and a full 2 car attached garage, perfectly located in the heart of Thornton Park, just few blocks from Lake Eola Park
Details for 9741 Star Trail, NEW PORT RICHEY, FL 34654
Single Family
  1. Price: $499,000.00
  2. Price sqft: $100.61 / sqft
  3. Previous Price: $515,000
  4. Last Price Change: 02/19/26
  5. Days On Market: 167
  6. Bedrooms: 5
  7. Baths: 5
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 4960
  10. Acreage: 1.78 acres
  11. Pool: No
  12. Waterfront: No
  13. Year Built: 1997
MLS#: W7879215
  1. County: PASCO
  2. City: NEW PORT RICHEY
  3. Zipcode: 34654
  4. Subdivision: Osceola Heights
  5. Provided by: RE/MAX ALLIANCE GROUP
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One or more photo(s) has been virtually staged. Welcome home to Golden Acres!! NEW ROOF's going on before closing!! Two Homes on Nearly 2 Acres!This is the perfect In Law Suite. Discover a rare oppor
Details for 10909 Candy Lane, NEW PORT RICHEY, FL 34654
Single Family
  1. Price: $499,000.00
  2. Price sqft: $167.79 / sqft
  3. Days On Market: 13
  4. Bedrooms: 3
  5. Baths: 2
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 2974
  8. Acreage: 1.01 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1976
MLS#: W7882726
  1. County: PASCO
  2. City: NEW PORT RICHEY
  3. Zipcode: 34654
  4. Subdivision: Osceola Heights
  5. Provided by: RE/MAX ALLIANCE GROUP
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One or more photo(s) has been virtually staged. Welcome to Golden Acres, where privacy, space, and modern updates come together beautifully. This fully remodeled 3 bedroom, 2 bath pool home offers exc