Searching on:
  1. Subdivision Like Winter Park
  2. Listing Status = Active
Details for 2412 Chantilly Avenue, WINTER PARK, FL 32789
Multi-Family
  1. Price: $7,150,000.00
  2. Days On Market: 10
  3. Garage / Parking Spaces: 8
  4. Acreage: 0.27 acres
  5. Pool: Yes
  6. Waterfront: No
  7. Year Built: 2026
MLS#: O6383456
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Winter Park Village
  5. Provided by: REAL BROKER, LLC
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This exclusive trifecta investment opportunity combines luxury real estate, dual lane income potential, and powerful tax advantagesall in one of the fastest growing markets in the country. Investors c
Details for 2661 Via Tuscany, WINTER PARK, FL 32789
Single Family
  1. Price: $6,600,000.00
  2. Price sqft: $1,261.71 / sqft
  3. Previous Price: $8,500,000
  4. Last Price Change: 09/08/25
  5. Days On Market: 460
  6. Bedrooms: 4
  7. Baths: 5
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 5231
  10. Acreage: 0.36 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 2024
MLS#: O6260493
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Winter Park
  5. Provided by: COMPASS FLORIDA LLC
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Calling highest and best by 09/26/2025!! Seller financing available with very attractive terms introducing a unique, stunning modern home a groundbreaking architectural masterpiece, this one of
Details for 503 Interlachen Avenue, WINTER PARK, FL 32789
Land
  1. Price: $4,500,000.00
  2. Previous Price: $4,999,000
  3. Last Price Change: 01/29/26
  4. Days On Market: 211
  5. Acreage: 0.48 acres
  6. Pool: No
  7. Waterfront: No
  8. Year Built: Not Available
MLS#: O6331207
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Winter Park
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: KELLY PRICE & COMPANY LLC
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JUST LISTED RARE 0.48 ACRE VACANT LOT IN DOWNTOWN WINTER PARK OFFERED AT $4,999,000!!! Zoned R 3, this multi family, prime piece of land is ready for development. Luxury townhomes or condos, nothi
Details for 457 New England Avenue, WINTER PARK, FL 32789
Single Family
  1. Price: $3,100,000.00
  2. Price sqft: $795.69 / sqft
  3. Days On Market: 156
  4. Bedrooms: 5
  5. Baths: 5
  6. Bldg sqft: 3896
  7. Acreage: 0.41 acres
  8. Pool: No
  9. Waterfront: No
  10. Year Built: 1920
MLS#: O6345511
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Winter Park
  5. Elementary School: Audubon Park K
  6. Middle School: Audubon Park K
  7. High School: Winter Park
  8. Provided by: PREMIER SOTHEBY'S INTL. REALTY
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Nestled in the heart of downtown Winter Park, this beautifully maintained 1920s traditional residence captures the essence of Old Florida charm while offering the comfort of modern amenities. From the
Details for 2412 Chantilly Avenue, WINTER PARK, FL 32789
Single Family
  1. Price: $2,395,000.00
  2. Price sqft: $460.93 / sqft
  3. Days On Market: 18
  4. Bedrooms: 5
  5. Baths: 7
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 5196
  8. Acreage: 0.27 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2024
MLS#: O6381552
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Winter Park Village
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: REAL BROKER, LLC
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Exceptional design meets refined luxury in this brand new architectural masterpiece by DaVinci. This 5 bedroom, 6.5 bath home offers over 4,500 square feet of bright, open living space designed for bo
Details for 2501 Lafayette Avenue, WINTER PARK, FL 32789
Single Family
  1. Price: $1,950,000.00
  2. Price sqft: $554.61 / sqft
  3. Days On Market: 17
  4. Bedrooms: 4
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3516
  8. Acreage: 0.18 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2026
MLS#: O6381988
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Winter Park Village
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: REAL BROKER, LLC
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Under Construction. Exceptional design meets refined luxury in this brand new architectural masterpiece by DaVinci. This 4 bedroom, 4 bath home offers over 2,800 square feet of bright, open living spa
Details for 1802 Arbor Park Drive, WINTER PARK, FL 32789
Single Family
  1. Price: $1,125,000.00
  2. Price sqft: $475.08 / sqft
  3. Previous Price: $1,150,000
  4. Last Price Change: 02/21/26
  5. Days On Market: 46
  6. Bedrooms: 4
  7. Baths: 3
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 2368
  10. Acreage: 0.27 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 1968
MLS#: O6372857
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Winter Park Heights
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: TBRO REALTY LLC
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Welcome home, perfectly positioned in one of Winter Parks most desirable communities, The Tree Streetswhere mature canopies, pride of ownership, and limited inventory make opportunities like this exce
Details for 456 Carolina Avenue, WINTER PARK, FL 32789
Single Family
  1. Price: $1,010,000.00
  2. Price sqft: $349.72 / sqft
  3. Days On Market: 1
  4. Bedrooms: 3
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 2888
  8. Acreage: 0.13 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 2004
MLS#: O6385625
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Winter Park
  5. Provided by: FANNIE HILLMAN & ASSOCIATES
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One or more photo(s) has been virtually staged. Experience the flagship lifestyle of winter park, where coastal inspiration meets timeless charm. This beautiful 3 bedroom, 3 bath residence offers a th
Details for 744 Cornwall Road, WINTER PARK, FL 32792
Single Family
  1. Price: $730,000.00
  2. Price sqft: $295.91 / sqft
  3. Previous Price: $750,000
  4. Last Price Change: 10/28/25
  5. Days On Market: 212
  6. Bedrooms: 4
  7. Baths: 2
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 2467
  10. Acreage: 0.23 acres
  11. Pool: No
  12. Waterfront: No
  13. Year Built: 1968
MLS#: O6332168
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32792
  4. Subdivision: Winter Park Pines
  5. Elementary School: Brookshire Elem
  6. Middle School: Glenridge
  7. High School: Winter Park
  8. Provided by: VERSALIS REALTY POWERED BY SELLSTATE
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Charming 4 Bedroom Home in Desirable Winter Park Pines Welcome to your new home in the heart of Winter Park Pines! This beautifully maintained 4 bedroom, 2 bath residence offers a perfect blend of cl
Details for 1134 Washington Avenue 13, WINTER PARK, FL 32789
Condominium
  1. Price: $645,000.00
  2. Price sqft: $309.65 / sqft
  3. Previous Price: $675,000
  4. Last Price Change: 01/10/26
  5. Days On Market: 97
  6. Bedrooms: 3
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 2083
  10. Acreage: 0.54 acres
  11. Pool: No
  12. Waterfront: No
  13. Year Built: 1981
MLS#: O6362206
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Quarters At Winter Park Condo
  5. Building: Quarters At Winter Park Condo
  6. Elementary School: Audubon Park K
  7. Middle School: Audubon Park K
  8. High School: Winter Park
  9. Provided by: KELLY PRICE & COMPANY LLC
  10. mfrmls
  11. DMCA Notice
Discover this generously sized 3 bedroom, 3.5 bath townhome offering 2,083 square feet of flexible living space in one of Winter Park's most coveted locations. This two story residence features a semi