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    501 Properties
    Map

    501 Properties Available In Winter Park

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    • Price-High To Low
    • Price-Low To High
    • Beds (Most)
    • Baths (Most)
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    FL >Winter Park >
    Market Insights
    • 1564 CAVENDISH RD, Winter Park, FL 32789
      3 Beds1 Bath1,140 SqFt
      1/17 17
      Active

      $450,000

      1564 CAVENDISH RD, Winter Park, FL 32789

      Listed by Julie Wright CHARLES RUTENBERG REALTY ORLANDO

      Stellar MLS
    • 2829 ALOMA AVE, Winter Park, FL 32792
      4 Beds2 Baths1,821 SqFt
      3D
      Pending

      $390,000

      2829 ALOMA AVE, Winter Park, FL 32792

      Listed by Cassie Lamoureux KELLER WILLIAMS CLASSIC

      Stellar MLS
    • 250 CORTLAND AVE, Winter Park, FL 32789
      3 Beds2 Baths2,114 SqFt
      1/68 68
      Active

      $950,000

      250 CORTLAND AVE, Winter Park, FL 32789

      Listed by Alexandra Nordine EXP REALTY LLC

      Stellar MLS
    • 3071 GEORGE MASON AVE #5, Winter Park, FL 32792
      1 Bath549 SqFt
      1/19 19
      Active

      $89,900

      3071 GEORGE MASON AVE #5, Winter Park, FL 32792

      Listed by Katherine Bordelon CASTLE & COTTAGE REALTY LLC

      Stellar MLS
    • 607 DUNBLANE DR, Winter Park, FL 32792
      4 Beds3 Baths2,046 SqFt
      1/44 44
      Active

      $675,000

      607 DUNBLANE DR, Winter Park, FL 32792

      Listed by Khozaif Merali CHARLES RUTENBERG REALTY ORLANDO

      Stellar MLS
    • 1921 TAYLOR AVE, Winter Park, FL 32792
      3 Beds2 Baths1,322 SqFt
      1/14 14
      Pending

      $410,000

      1921 TAYLOR AVE, Winter Park, FL 32792

      Listed by Brianna Perez Montalvo EXP REALTY LLC

      Stellar MLS
    • 1444 PELICAN BAY TRL, Winter Park, FL 32792
      4 Beds3 Baths3,121 SqFt
      1/57 57
      Active

      $999,950

      1444 PELICAN BAY TRL, Winter Park, FL 32792

      Listed by Jacob Hara TRANSCEND REALTY

      Stellar MLS
    • 2418 WHITEHALL CIR, Winter Park, FL 32792
      3 Beds2 Baths2,134 SqFt
      1/42 42
      Pending

      $715,000

      2418 WHITEHALL CIR, Winter Park, FL 32792

      Listed by Alice Anne Jackson CORCORAN PREMIER REALTY

      Stellar MLS
    • 1695 LEE RD #C202, Winter Park, FL 32789
      3 Beds2 Baths1,149 SqFt
      Active

      $210,000

      1695 LEE RD #C202, Winter Park, FL 32789

      Listed by Hoover Yap PRIMESTATE REALTY, INC.

      Stellar MLS
    • 7706 COUNTRY PL #7706, Winter Park, FL 32792
      3 Beds2 Baths1,230 SqFt
      1/19 19
      Active

      $245,000

      7706 COUNTRY PL #7706, Winter Park, FL 32792

      Listed by Carmen Vazquez REALTY TECH INC

      Stellar MLS
    • 1400 ALABAMA DR, Winter Park, FL 32789
      5 Beds9 Baths7,916 SqFt
      1/84 84
      Active

      $5,895,000

      1400 ALABAMA DR, Winter Park, FL 32789

      Listed by Rachel Peters, LLC THE AGENCY ORLANDO

      Stellar MLS
    • 1660 PALMER AVE, Winter Park, FL 32789
      5 Beds7 Baths6,406 SqFt
      1/48 48
      Active

      $4,950,000

      1660 PALMER AVE, Winter Park, FL 32789

      Listed by Mick Night PREMIER SOTHEBY'S INTL. REALTY

      Stellar MLS
    • 2923 ANTIQUE OAKS CIR #39, Winter Park, FL 32792
      2 Beds2 Baths1,105 SqFt
      1/22 22
      Active

      $200,000

      2923 ANTIQUE OAKS CIR #39, Winter Park, FL 32792

      Listed by Michell Carrasquero GLOBALWIDE REALTY LLC

      Stellar MLS
    • 726 and 720 N PENNSYLVANIA AVE, Winter Park, FL 32789
      6 Beds4 Baths2,284 SqFt
      1/49 49
      Active

      $1,215,000

      726 and 720 N PENNSYLVANIA AVE, Winter Park, FL 32789

      Listed by Dominick Florio RE/MAX TOWN & COUNTRY REALTY

      Stellar MLS
    • 726/720 N PENNSYLVANIA AVE, Winter Park, FL 32789
      6 Beds4 Baths2,284 SqFt
      1/49 49
      Active

      $1,215,000

      726/720 N PENNSYLVANIA AVE, Winter Park, FL 32789

      Listed by Dominick Florio RE/MAX TOWN & COUNTRY REALTY

      Stellar MLS
    • 726 N PENNSYLVANIA AVE, Winter Park, FL 32789
      3 Beds2 Baths1,167 SqFt
      1/30 30
      Active

      $695,000

      726 N PENNSYLVANIA AVE, Winter Park, FL 32789

      Listed by Dominick Florio RE/MAX TOWN & COUNTRY REALTY

      Stellar MLS
    • 720 N PENNSYLVANIA AVE, Winter Park, FL 32789
      3 Beds2 Baths1,115 SqFt
      1/26 26
      Active

      $550,000

      720 N PENNSYLVANIA AVE, Winter Park, FL 32789

      Listed by Dominick Florio RE/MAX TOWN & COUNTRY REALTY

      Stellar MLS
    • 625 BRECHIN DR, Winter Park, FL 32792
      3 Beds2 Baths1,827 SqFt
      1/42 42
      Active

      $765,000

      625 BRECHIN DR, Winter Park, FL 32792

      Listed by Kelly Price KELLY PRICE & COMPANY LLC

      Stellar MLS
    • 2500 LEE RD #202, Winter Park, FL 32789
      2 Beds2 Baths956 SqFt
      1/39 39
      Active

      $239,990

      2500 LEE RD #202, Winter Park, FL 32789

      Listed by Alison Maltby THE ANDERSON GROUP & CO PL

      Stellar MLS
    • 1400 S PENNSYLVANIA AVE, Winter Park, FL 32789
      4 Beds3 Baths2,310 SqFt
      1/50 50
      Active

      $1,250,000

      1400 S PENNSYLVANIA AVE, Winter Park, FL 32789

      Listed by John Keller JACK KELLER INC

      Stellar MLS
    • 1417 MILLER AVE, Winter Park, FL 32789
      5 Beds4 Baths3,312 SqFt
      1/6 6
      Pending

      $1,599,900

      1417 MILLER AVE, Winter Park, FL 32789

      Listed by Laura Earl CORCORAN PREMIER REALTY

      Stellar MLS
    • 334 SCOTTSDALE SQ #334, Winter Park, FL 32792
      3 Beds2 Baths1,250 SqFt
      1/11 11
      Active

      $130,000

      334 SCOTTSDALE SQ #334, Winter Park, FL 32792

      Listed by John Sheynkman CHARLES RUTENBERG REALTY ORLANDO

      Stellar MLS
    • 1116 FAIRWAY DR, Winter Park, FL 32792
      3 Beds2 Baths1,738 SqFt
      1/38 38
      Pending

      $499,900

      1116 FAIRWAY DR, Winter Park, FL 32792

      Listed by Mathew Kelly TURN-KEY MOVES REALTY

      Stellar MLS
    • 7403 GLEN OAKS WAY #82, Winter Park, FL 32792
      3 Beds3 Baths1,161 SqFt
      1/20 20
      Pending

      $199,900

      7403 GLEN OAKS WAY #82, Winter Park, FL 32792

      Listed by Efrain Feliz OUTLET REALTY

      Stellar MLS
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    sg lpt white transparent
    LPT Realty

    Katherine Sakkis License ID: SL580806

    +1(813) 309-1073 ksakkis@sakkisgroup.com

      • Home
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      • Buy
        1. New Construction Homes
        2. All Listings
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        4. Sold Listings
        5. Mortgage Calculator
        6. Things To Consider When Buying A Home
        Market Snapshot
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    Powered by Lofty Inc. Copyright 2025. All Rights Reserved.

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

    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.