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2661 Via Tuscany
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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: 09/16/25
  5. Days On Market: 437
  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: PV LUXURY GROUP PA
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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
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503 Interlachen Avenue
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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: 01/28/26
  4. Days On Market: 189
  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 Middle
  7. High School: Winter Park High
  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
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457 New England Avenue
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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: 133
  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 K8
  6. Middle School: Audubon Park K 8
  7. High School: Winter Park High
  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
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2412 Chantilly Avenue
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Details for 2412 Chantilly Avenue, WINTER PARK, FL 32789
Single Family
  1. Price: $2,295,000.00
  2. Price sqft: $441.69 / sqft
  3. Previous Price: $2,350,000
  4. Last Price Change: 01/22/26
  5. Days On Market: 85
  6. Bedrooms: 5
  7. Baths: 7
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 5196
  10. Acreage: 0.27 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 2024
MLS#: O6360088
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Winter Park Village
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park High
  8. Provided by: THE AGENCY FL
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Step into a world of modern elegance in this newly completed estate in the heart of Winter Park. Masterfully constructed, this five bedroom residence with six full and one half baths spans over 4,500
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2001 Lake Drive
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Details for 2001 Lake Drive, WINTER PARK, FL 32789
Single Family
  1. Price: $2,150,000.00
  2. Price sqft: $425.83 / sqft
  3. Previous Price: $2,165,000
  4. Last Price Change: 01/29/26
  5. Days On Market: 127
  6. Bedrooms: 5
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 5049
  10. Acreage: 0.41 acres
  11. Pool: Yes
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Canal - Freshwater
  15. Year Built: 1961
MLS#: O6336920
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Winter Park
  5. Elementary School: Killarney Elem
  6. Middle School: College Park Middle
  7. High School: Edgewater High
  8. Provided by: THE AGENCY FL
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Nestled on a quiet cul de sac in the heart of Winter Park, this canal front residence offers the perfect balance of elegance and lifestyle. With direct access to Lake Killarney, the home invites days
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1802 Arbor Park Drive
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Details for 1802 Arbor Park Drive, WINTER PARK, FL 32789
Single Family
  1. Price: $1,150,000.00
  2. Price sqft: $485.64 / sqft
  3. Days On Market: 23
  4. Bedrooms: 4
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 2368
  8. Acreage: 0.27 acres
  9. Pool: Yes
  10. Waterfront: No
  11. 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 Middle
  7. High School: Winter Park High
  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
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2607 Lafayette Avenue
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Details for 2607 Lafayette Avenue, WINTER PARK, FL 32789
Single Family
  1. Price: $1,095,000.00
  2. Price sqft: $281.93 / sqft
  3. Previous Price: $1,180,000
  4. Last Price Change: 07/16/25
  5. Days On Market: 248
  6. Bedrooms: 4
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 3884
  10. Acreage: 0.18 acres
  11. Pool: No
  12. Waterfront: No
  13. Year Built: 2018
MLS#: O6314734
  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: FORTUNE INTERNATIONAL REALTY
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Welcome to 2607 Lafayette Avenue a stunning custom built residence nestled in one of Winter Parks most desirable neighborhoods. This beautifully crafted home offers 4 spacious bedrooms, 3.5 bathrooms
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744 Cornwall Road
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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: 08/12/25
  5. Days On Market: 190
  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
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744 Cornwall Road
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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: 189
  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
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1134 Washington Avenue 13
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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: 01/11/26
  5. Days On Market: 74
  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 K8
  7. Middle School: Audubon Park K 8
  8. High School: Winter Park High
  9. Provided by: KELLY PRICE & COMPANY LLC
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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
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