Homes in ZIP Code 32789

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  Est $679,908 Not Listed For Sale

  1580 Chestnut Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,482 Sq Ft
  • Built 1971

  1580 Chestnut Ave, Winter Park, FL 32789

  Last Sold Summary

  • 12% Above List Price
  • $409/SF
  • 4 Days On Market

  Last Sold Price $606,000

  Last Listing Agent Nicole Howell FANNIE HILLMAN & ASSOCIATES
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  /9

  $1,595,000

  • 3 Beds
  • 2 Baths
  • 2,012 Sq Ft

  1113 Via Del Mar, Winter Park, FL 32789

  Exceptional opportunity in the heart of Winter Park — a truly premier and irreplaceablehomesite offering rare scale, privacy, and extraordinary future build potential. The primaryvalue is in the land, presenting an unparalleled canvas for a custom luxury residence, withvirtually no comparable vacant land available in the immediate vicinity. Set on a tranquil smalllake that

  David Barany BAY HILL REALTY LLC

  1113 Via Del Mar, Winter Park, FL 32789
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  /2

  $819,000 Sold Oct 31, 2025

  734 Maryland Ave, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,250 Sq Ft
  • Built 1926

  Last Sold Summary

  • 3% Below List Price
  • $655/SF
  • 44 Days On Market

  Current Estimated Value $814,465

  Last Listing Agent Michael Domi COMPASS FLORIDA LLC

  734 Maryland Ave, Winter Park, FL 32789
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  /2

  Est $910,200 Not Listed For Sale

  1762 Chestnut Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,760 Sq Ft
  • Built 1957

  1762 Chestnut Ave, Winter Park, FL 32789

  Last Sold Summary

  • 1% Above List Price
  • $511/SF
  • 37 Days On Market

  Last Sold Price $899,000

  Last Listing Agent Heather Frazee FANNIE HILLMAN & ASSOCIATES
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  /50

  $3,250,000 Pending

  • 5 Beds
  • 5.5 Baths
  • 4,296 Sq Ft

  473 Fletcher Place, Winter Park, FL 32789

  Welcome to the best of Winter Park living, where luxury meets lifestyle and every day feels like a getaway. This stunning custom home, built by Lundev, sits on a quiet, tree-lined street just a mile from Park Avenue and only steps from beautiful Lake Osceola. Imagine walking to brunch on Park Ave, then coming home to launch your paddleboard from the end of your street. From the moment you pull

  Brandon Geers COMPASS FLORIDA LLC

  473 Fletcher Place, Winter Park, FL 32789
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  /2

  $410,000 Sold Dec 02, 2025

  2464 Lotafun Ave, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 1,804 Sq Ft
  • Built 1951

  Last Sold Summary

  • 9% Below List Price
  • $227/SF
  • 112 Days On Market

  Current Estimated Value $412,927

  Last Listing Agent Irina Paul FUTURE HOME REALTY INC

  2464 Lotafun Ave, Winter Park, FL 32789
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  /2

  Est $1,817,121 Not Listed For Sale

  1530 Via Tuscany, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 3,341 Sq Ft
  • Built 1972

  1530 Via Tuscany, Winter Park, FL 32789

  Last Sold Summary

  • 14% Above List Price
  • $479/SF
  • 377 Days On Market

  Last Sold Price $1,600,000

  Last Listing Agent Dan Haber CORCORAN PREMIER REALTY
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  /7

  $899,000

  • Land
  • 0.19 Acre
  • $4,731,579 per Acre

  731 Midget Dr, Winter Park, FL 32789

  Rare corner lot with stunning views of Lake Midget, located in the heart of Winter Park within an area of modern new-construction homes. This build-ready property offers an exceptional opportunity to create a custom residence in one of the city’s most desirable neighborhoods. Just minutes from Park Avenue and Winter Park Village, with easy access to premier dining, shopping, and

  Juliana Usquiano EMPIRE NETWORK REALTY

  731 Midget Dr, Winter Park, FL 32789
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  /2

  $850,000 Sold Jun 20, 2025

  1919 S Lakemont Ave, Winter Park, FL 32792

  • 3 Beds
  • 3.5 Baths
  • 2,085 Sq Ft
  • Built 2024

  Last Sold Summary

  • 10% Below List Price
  • $408/SF
  • 282 Days On Market

  Current Estimated Value $856,630

  Last Listing Agent Nickolas McKee KELLER WILLIAMS WINTER PARK

  1919 S Lakemont Ave, Winter Park, FL 32792
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  /2

  Est $1,122,178 Not Listed For Sale

  363 N Phelps Ave, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,871 Sq Ft
  • Built 1950

  363 N Phelps Ave, Winter Park, FL 32789

  Last Sold Summary

  • 1% Above List Price
  • $388/SF
  • 144 Days On Market

  Last Sold Price $1,115,000

  Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC
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  /50

  $1,195,000

  • 2 Beds
  • 2 Baths
  • 1,402 Sq Ft

  1602 Alabama Dr Unit 403, Winter Park, FL 32789

  Perched on the top floor in the heart of Winter Park, this luxury, open-concept residence offers a rare blend of elevated design and everyday ease. Enjoy the peace of no neighbors above, plus the privacy, security, and lock-and-leave convenience that only condo living can provide without sacrificing space, light, or lifestyle. The Alabama delivers a rare Winter Park combo of modern living and

  Matthew Burks CORCORAN PREMIER REALTY

  1602 Alabama Dr Unit 403, Winter Park, FL 32789
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  /2

  $1,395,000 Sold Mar 26, 2025

  1771 Winchester Dr, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 2,516 Sq Ft
  • Built 1957

  Last Sold Summary

  • $554/SF
  • 0 Days On Market

  Current Estimated Value $1,407,714

  Last Listing Agent Michael Ford FANNIE HILLMAN & ASSOCIATES

  1771 Winchester Dr, Winter Park, FL 32789
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  /2

  Est $743,071 Not Listed For Sale

  678 Depugh St, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 1,940 Sq Ft
  • Built 1952

  678 Depugh St, Winter Park, FL 32789

  Last Sold Summary

  • 10% Above List Price
  • $348/SF
  • 89 Days On Market

  Last Sold Price $675,000

  Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK
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  /33

  $875,000 Open Sat 12PM - 3PM

  • 4 Beds
  • 3 Baths
  • 2,509 Sq Ft

  668 Overspin Dr, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. A contemporary, beautifully finished home offering standout value in one of Winter Park’s most coveted zip codes. With more than 2,500 square feet of bright, open living space, this property features a sleek fireplace, a large pantry area, a designer kitchen, and a massive two-car garage. The private primary suite sits upstairs along with additional

  Kris Kennedy COMPASS FLORIDA LLC

  668 Overspin Dr, Winter Park, FL 32789
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  /2

  $199,000 Sold Aug 01, 2025

  851 Miles Ave Unit 8, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 808 Sq Ft
  • Built 1984

  Last Sold Summary

  • 12% Below List Price
  • $246/SF
  • 16 Days On Market

  Current Estimated Value $193,592

  Last Listing Agent Bobby Christiano COLDWELL BANKER REALTY

  851 Miles Ave Unit 8, Winter Park, FL 32789
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  /2

  Est $987,988 Not Listed For Sale

  1875 Lake Spier Dr, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,366 Sq Ft
  • Built 1958

  1875 Lake Spier Dr, Winter Park, FL 32789

  Last Sold Summary

  • 1% Above List Price
  • $717/SF
  • 33 Days On Market

  Last Sold Price $980,000

  Last Listing Agent Angelina Cyprich FLORIDA REALTY INVESTMENTS
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  /19

  $450,000

  • 1 Bed
  • 1 Bath
  • 673 Sq Ft

  640 N Park Ave Unit 5, Winter Park, FL 32789

  Location, Location, Location!Charming first floor 1 bedroom, 1 bath condo ideally located on North Park Avenue in the retro-chic Park Aire complex. Beautifully overhauled in 2018 with quartz counters, new cabinetry, new appliances, custom mosaic kitchen detail, new flooring, new lighting, updated electrical, with picturesque views of the Winter Park Golf Course and Casa Feliz.Enjoy a

  David Auerbach PARK TOWN REAL ESTATE LLC

  640 N Park Ave Unit 5, Winter Park, FL 32789
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  /2

  $412,000 Sold Aug 22, 2025

  535 N Interlachen Ave Unit 107, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,088 Sq Ft
  • Built 1972

  Last Sold Summary

  • 18% Below List Price
  • $379/SF
  • 127 Days On Market

  Current Estimated Value $415,031

  Last Listing Agent Mary Colton FANNIE HILLMAN & ASSOCIATES

  535 N Interlachen Ave Unit 107, Winter Park, FL 32789
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  /2

  Est $449,653 Not Listed For Sale

  1501 Michigan Ave, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 853 Sq Ft
  • Built 1936

  1501 Michigan Ave, Winter Park, FL 32789

  Last Sold Summary

  • $528/SF
  • 5 Days On Market

  Last Sold Price $450,000

  Last Listing Agent Brad Corbitt CREEGAN GROUP
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  /11

  $1,800,000

  • Land
  • 0.3 Acre
  • $6,000,000 per Acre

  1181 Via Capri, Winter Park, FL 32789

  Build your dream home in one of Winter Park’s most desirable areas. This exceptional vacant lot at 1181 Via Capri offers a rare opportunity to create a custom residence in a well-established neighborhood known for its charm, convenience, and strong property values. Ideally located just minutes from Park Avenue, top-rated schools, dining, shopping, and major roadways, this homesite provides both

  Ana Semmel KARDOSH REALTY

  1181 Via Capri, Winter Park, FL 32789

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