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    269 Properties
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    269 Properties Available

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    • Newest Listings
    • Beds (Most)
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    • 708 BALMORAL RD, Winter Park, FL 32789
      4 Beds3 Baths2,786 SqFt
      New

      $1,690,000

      708 BALMORAL RD, Winter Park, FL 32789

      Listed by Caitlin De Oliveira EXP REALTY LLC

      Stellar MLS
    • 1546 MILLER AVE, Winter Park, FL 32789
      4 Beds4 Baths2,984 SqFt
      1/36 36
      New

      $1,419,900

      1546 MILLER AVE, Winter Park, FL 32789

      Listed by Kim Griffin RE/MAX EXCLUSIVE COLLECTION

      Stellar MLS
    • 1850 BRYAN AVE, Winter Park, FL 32789
      3 Beds2 Baths1,563 SqFt
      1/26 26
      New

      $795,000

      1850 BRYAN AVE, Winter Park, FL 32789

      Listed by Vanessa Winters CENTRAL FLORIDA REAL ESTATE CE

      Stellar MLS
    • 2323 DEVON CT, Winter Park, FL 32789
      4 Beds2 Baths2,403 SqFt
      3D
      New

      $429,000

      2323 DEVON CT, Winter Park, FL 32789

      Listed by Renee Taylor CREEGAN GROUP

      Stellar MLS
    • 1271 PALMER AVE, Winter Park, FL 32789
      4 Beds5 Baths2,835 SqFt
      3D
      New

      $2,275,000

      1271 PALMER AVE, Winter Park, FL 32789

      Listed by Sheri Malin REDFIN CORPORATION

      Stellar MLS
    • 2234 HOWARD DR, Winter Park, FL 32789
      4 Beds6 Baths3,295 SqFt
      1/25 25
      New

      $8,295

      2234 HOWARD DR, Winter Park, FL 32789

      Listed by Raquel Elliott COLDWELL BANKER REALTY

      Stellar MLS
    • 405 LAKEWOOD DR, Winter Park, FL 32789
      4 Beds3 Baths4,208 SqFt
      1/2 2
      Pending

      $6,700,000

      405 LAKEWOOD DR, Winter Park, FL 32789

      Listed by Kelly Price KELLY PRICE & COMPANY LLC

      Stellar MLS
    • 2824 WOODSIDE AVE, Winter Park, FL 32789
      2 Beds2 Baths912 SqFt
      1/17 17
      New

      $600,000

      2824 WOODSIDE AVE, Winter Park, FL 32789

      Listed by Kristin Haughwout-Osorio PARKSIDE PROPERTIES, LLC

      Stellar MLS
    • 901 HARMON AVE, Winter Park, FL 32789
      2 Beds2 Baths1,277 SqFt
      1/20 20
      New

      $650,000

      901 HARMON AVE, Winter Park, FL 32789

      Listed by Samuel Kingsford STOCKWORTH REALTY GROUP

      Stellar MLS
    • 2252 HOWARD DR, Winter Park, FL 32789
      3 Beds2 Baths1,406 SqFt
      1/29 29
      New

      $3,200

      2252 HOWARD DR, Winter Park, FL 32789

      Listed by Michelle Morrow REALTY PROS UNLIMITED INC

      Stellar MLS
    • 281 BREWER AVE, Winter Park, FL 32789
      5 Beds5 Baths4,029 SqFt
      1/54 54
      New

      $1,800,000

      281 BREWER AVE, Winter Park, FL 32789

      Listed by John Henthorn HENTHORN REAL ESTATE

      Stellar MLS
    • 216 BLOSSOM LN, Winter Park, FL 32789
      4 Beds2 Baths1,933 SqFt
      1/63 63
      Active Under Contract

      $624,900

      216 BLOSSOM LN, Winter Park, FL 32789

      Listed by Katie Tedesco COLDWELL BANKER REALTY

      Stellar MLS
    • 1261 RICHMOND RD, Winter Park, FL 32789
      2 Beds1 Bath954 SqFt
      1/16 16
      New

      $2,099

      1261 RICHMOND RD, Winter Park, FL 32789

      Listed by Steven Simpson 407 PROPERTIES

      Stellar MLS
    • 640 N PARK AVE #4, Winter Park, FL 32789
      1 Bed1 Bath673 SqFt
      1/33 33
      New

      $2,200

      640 N PARK AVE #4, Winter Park, FL 32789

      Listed by Flory Clark UNITED REAL ESTATE PREFERRED

      Stellar MLS
    • 240 KILLARNEY DR, Winter Park, FL 32789
      3 Beds3 Baths1,329 SqFt
      1/15 15
      Active

      $1,275,000

      240 KILLARNEY DR, Winter Park, FL 32789

      Listed by Shandy Ortiz PREMIER SOTHEBYS INT'L REALTY

      Stellar MLS
    • 230 KILLARNEY DR, Winter Park, FL 32789
      4 Beds1 Bath1,260 SqFt
      1/15 15
      Active

      $1,250,000

      230 KILLARNEY DR, Winter Park, FL 32789

      Listed by Shandy Ortiz PREMIER SOTHEBYS INT'L REALTY

      Stellar MLS
    • 2568 LOTAFUN AVE, Winter Park, FL 32789
      3 Beds2 Baths1,201 SqFt
      1/25 25
      Active

      $409,900

      2568 LOTAFUN AVE, Winter Park, FL 32789

      Listed by Randall Wolber, Jr SIMPLE FEE LISTINGS LLC

      Stellar MLS
    • 846 DRIVER AVE, Winter Park, FL 32789
      2 Beds1 Bath824 SqFt
      3D
      Active

      $310,000

      846 DRIVER AVE, Winter Park, FL 32789

      Listed by Donald Harkins, III DON HARKINS REALTY LLC

      Stellar MLS
    • 1627 ORANGE AVE, Winter Park, FL 32789
      3 Beds2 Baths1,302 SqFt
      1/36 36
      Coming Soon

      $2,750

      1627 ORANGE AVE, Winter Park, FL 32789

      Listed by Peter Dang ALLIANCE RENTAL HOMES

      Stellar MLS
    • 1351 ONECO AVE, Winter Park, FL 32789
      4 Beds3 Baths2,474 SqFt
      1/30 30
      Active

      $1,150,000

      1351 ONECO AVE, Winter Park, FL 32789

      Listed by Maria Van Warner FANNIE HILLMAN & ASSOCIATES

      Stellar MLS
    • 1871 BARKER DR, Winter Park, FL 32789
      3 Beds3 Baths2,231 SqFt
      1/36 36
      Active Under Contract

      $779,000

      1871 BARKER DR, Winter Park, FL 32789

      Listed by Rikhil Amin FANNIE HILLMAN & ASSOCIATES

      Stellar MLS
    • 1562 ARBOR PARK DR, Winter Park, FL 32789
      4 Beds3 Baths1,899 SqFt
      3D
      Active

      $775,000

      1562 ARBOR PARK DR, Winter Park, FL 32789

      Listed by Abby Greenberg COMPASS FLORIDA LLC

      Stellar MLS
    • 1134 WASHINGTON AVE #13C, Winter Park, FL 32789
      3 Beds4 Baths2,195 SqFt
      1/41 41
      Active

      $525,000

      1134 WASHINGTON AVE #13C, Winter Park, FL 32789

      Listed by Drew Henner PREMIER SOTHEBY'S INTL. REALTY

      Stellar MLS
    • 1500 GAY RD #4D, Winter Park, FL 32789
      1 Bed1 Bath732 SqFt
      1/15 15
      Active

      $175,000

      1500 GAY RD #4D, Winter Park, FL 32789

      Listed by Janice Erickson REALCOM REAL ESTATE SERVICES INC

      Stellar MLS
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    Black with Red
    Engel & Völkers
    Marisa Gillman Denton | License ID: BK 3335871

    +1(386) 682-9776

    marisa.gillmandenton@engelvoelkers.com

    Get My App

    IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.

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    Powered by Lofty Inc. Copyright 2026. All Rights Reserved.

    Black with Red
    Engel & Völkers
    Marisa Gillman Denton | License ID: BK 3335871

    +1(386) 682-9776

    marisa.gillmandenton@engelvoelkers.com

    Get My App

    IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.

    Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility

    Powered by Lofty Inc. Copyright 2026. All Rights Reserved.