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  1. Subdivision Like Winter Park
  2. Listing Status = Active
2412 Chantilly Avenue
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Details for 2412 Chantilly Avenue, WINTER PARK, FL 32789
Multi-Family
  1. Price: $7,150,000.00
  2. Days On Market: 13
  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
  6. mfrmls
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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
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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: 09/08/25
  5. Days On Market: 463
  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
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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: 01/29/26
  4. Days On Market: 215
  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
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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: 159
  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
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2412 Chantilly Avenue
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Details for 2412 Chantilly Avenue, WINTER PARK, FL 32789
Single Family
  1. Price: $2,395,000.00
  2. Price sqft: $460.93 / sqft
  3. Days On Market: 21
  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: 2026
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
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2501 Lafayette Avenue
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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: 20
  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
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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: $1,125,000.00
  2. Price sqft: $475.08 / sqft
  3. Previous Price: $1,150,000
  4. Last Price Change: 02/21/26
  5. Days On Market: 49
  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
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456 Carolina Avenue
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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: 4
  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
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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: 215
  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: 01/10/26
  5. Days On Market: 100
  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
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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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Tropic Shores Realty - Crystal River
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Listing Data ©2026 Greater Fort Lauderdale REALTORS®
Listings provided courtesy of The Hernando County Association of Realtors MLS.
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Listing Data ©2026 Royal Palm Coast Realtor® Association
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Datafeed Last updated on March 5, 2026 @ 12:00 am
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