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367 Properties
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367 Featured Properties Available

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  • Newest Listings
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  • Beds (Most)
  • Baths (Most)
  • Year Built (Newest)
  • 1008 N PENNSYLVANIA AVE, Winter Park, FL 32789
    4 Beds5 Baths3,530 SqFt
    1/48 48
    New

    $2,500,000

    1008 N PENNSYLVANIA AVE, Winter Park, FL 32789

    Listed by Joseph Sipp KELLER WILLIAMS WINTER PARK

    Stellar MLS
  • 1250 S DENNING DR #203, Winter Park, FL 32789
    2 Beds2 Baths908 SqFt
    New

    $260,000

    1250 S DENNING DR #203, Winter Park, FL 32789

    Listed by Fadi Bohlok NOVANEST REALTY LLC

    Stellar MLS
  • 1351 MAYFIELD AVE, Winter Park, FL 32789
    5 Beds5 Baths3,677 SqFt
    1/13 13
    New

    $3,050,000

    1351 MAYFIELD AVE, Winter Park, FL 32789

    Listed by Christopher Christensen ONE LUXURY INTERNATIONAL LLC

    Stellar MLS
  • 470 W COMSTOCK AVE, Winter Park, FL 32789
    6 Beds7 Baths6,134 SqFt
    1/46 46
    New

    $5,480,000

    470 W COMSTOCK AVE, Winter Park, FL 32789

    Listed by Vera Rosado EQUITY PARTNERS REAL EST LLC

    Stellar MLS
  • 610 PENN PL, Winter Park, FL 32789
    4 Beds4 Baths3,174 SqFt
    1/54 54
    New

    $1,895,000

    610 PENN PL, Winter Park, FL 32789

    Listed by Skip Kirst COLLADO REAL ESTATE

    Stellar MLS
  • 2531 PASSAMONTE DR #4H, Winter Park, FL 32792
    3 Beds3 Baths1,790 SqFt
    3D
    New

    $369,000

    2531 PASSAMONTE DR #4H, Winter Park, FL 32792

    Listed by Andre Asselin REDFIN CORPORATION

    Stellar MLS
  • 2718 EASTERN Pkwy, Winter Park, FL 32789
    4 Beds5 Baths3,308 SqFt
    1/41 41
    Open Sun 1PM-4PM

    $2,450,000

    2718 EASTERN Pkwy, Winter Park, FL 32789

    Listed by Nick McKee KELLER WILLIAMS WINTER PARK

    Stellar MLS
  • 2821 CHANTILLY AVE, Winter Park, FL 32789
    3 Beds2 Baths1,440 SqFt
    1/35 35
    New

    $415,000

    2821 CHANTILLY AVE, Winter Park, FL 32789

    Listed by April Mycz RISE REALTY OF FLORIDA LLC

    Stellar MLS
  • 2821 RIDDLE DR, Winter Park, FL 32789
    4 Beds4 Baths2,445 SqFt
    1/28 28
    New

    $299,900

    2821 RIDDLE DR, Winter Park, FL 32789

    Listed by Linda Mardegan ORLANDO REGIONAL REALTY

    Stellar MLS
  • 647 RANDY LN, Winter Park, FL 32789
    4 Beds4 Baths2,923 SqFt
    1/56 56
    New

    $1,699,999

    647 RANDY LN, Winter Park, FL 32789

    Listed by Carrie Sue Shawfield SHAWFIELD REALTY GROUP

    Stellar MLS
  • 2507 LAFAYETTE AVE, Winter Park, FL 32789
    4 Beds6 Baths2,675 SqFt
    1/54 54
    Open Sat 12PM-2PM

    $1,850,000

    2507 LAFAYETTE AVE, Winter Park, FL 32789

    Listed by Christopher Christensen ONE LUXURY INTERNATIONAL LLC

    Stellar MLS
  • 3148 NICHOLSON DR, Winter Park, FL 32792
    3 Beds2 Baths1,577 SqFt
    3D
    New

    $449,000

    3148 NICHOLSON DR, Winter Park, FL 32792

    Listed by Erica Diaz HOMEVEST REALTY

    Stellar MLS
  • Winter Park, FL 32789
    4 Beds5 Baths2,830 SqFt
    1/56 56
    New

    $2,100,000

    Winter Park, FL 32789

    Listed by Stephanie Moore PLATINUM REALTY GROUP FLORIDA INC

    Stellar MLS
  • 1934 TAYLOR AVE, Winter Park, FL 32792
    4 Beds2 Baths1,470 SqFt
    3D
    New

    $499,000

    1934 TAYLOR AVE, Winter Park, FL 32792

    Listed by Thomas Nickley, Jr KELLER WILLIAMS REALTY AT THE PARKS

    Stellar MLS
  • 2885 ROXBURY RD, Winter Park, FL 32789
    3 Beds2 Baths1,511 SqFt
    1/20 20
    New

    $450,000

    2885 ROXBURY RD, Winter Park, FL 32789

    Listed by Jason Ricks COLDWELL BANKER REALTY

    Stellar MLS
  • 531 WORTHINGTON DR, Winter Park, FL 32789
    3 Beds3 Baths2,626 SqFt
    1/32 32
    Open Sun 12PM-2PM

    $1,100,000

    531 WORTHINGTON DR, Winter Park, FL 32789

    Listed by Catherine D'Amico FANNIE HILLMAN & ASSOCIATES

    Stellar MLS
  • 535 N INTERLACHEN AVE #302, Winter Park, FL 32789
    2 Beds2 Baths970 SqFt
    1/33 33
    New

    $485,000

    535 N INTERLACHEN AVE #302, Winter Park, FL 32789

    Listed by Mary Colton FANNIE HILLMAN & ASSOCIATES

    Stellar MLS
  • 640 N PARK AVE #26, Winter Park, FL 32790
    2 Beds2 Baths858 SqFt
    1/19 19
    New

    $629,500

    640 N PARK AVE #26, Winter Park, FL 32790

    Listed by Michael O'Shaughnessy MICHAEL O'SHAUGHNESSY, INC.

    Stellar MLS
  • 1140 WASHINGTON AVE #16C, Winter Park, FL 32789
    3 Beds3 Baths2,069 SqFt
    1/10 10
    Open Sat 2PM-5PM

    $739,000

    1140 WASHINGTON AVE #16C, Winter Park, FL 32789

    Listed by Chevon Eaton CHEVON EATON

    Stellar MLS
  • 1386 CLEMATIS LN, Winter Park, FL 32792
    4 Beds3 Baths1,714 SqFt
    1/25 25
    New

    $417,000

    1386 CLEMATIS LN, Winter Park, FL 32792

    Listed by Daisy Villanueva EMPIRE REALTY & MANAGEMENT SERVICES

    Stellar MLS
  • 1400 PELICAN BAY TRL, Winter Park, FL 32792
    5 Beds4 Baths3,600 SqFt
    1/69 69
    New

    $968,000

    1400 PELICAN BAY TRL, Winter Park, FL 32792

    Listed by Courtney Davis ABSOLUTE REALTY GROUP, LLC

    Stellar MLS
  • 1507 GOLFSIDE DR, Winter Park, FL 32792
    3 Beds2 Baths2,003 SqFt
    1/34 34
    New

    $849,000

    1507 GOLFSIDE DR, Winter Park, FL 32792

    Listed by Cameron Matoska LPT REALTY, LLC

    Stellar MLS
  • 2176 CRANDON AVE, Winter Park, FL 32789
    2 Beds1 Bath959 SqFt
    1/19 19
    New

    $399,000

    2176 CRANDON AVE, Winter Park, FL 32789

    Listed by Dan Haber CORCORAN PREMIER REALTY

    Stellar MLS
  • 3157 SHADY PINE AVE, Winter Park, FL 32792
    3 Beds2 Baths1,495 SqFt
    1/31 31
    New

    $425,000

    3157 SHADY PINE AVE, Winter Park, FL 32792

    Listed by Stacy Morano MID-STATE PROPERTIES PSL LLC

    Stellar MLS
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GPG Team
Tyler Gibson
License ID: 3454664
+1(407) 934-0320
tyler@gpghome.com
Lake Mary, FL, 32746

  • Home
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    2. Disney Short Term Rentals
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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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GPG Team
Tyler Gibson
License ID: 3454664
+1(407) 934-0320
tyler@gpghome.com
Lake Mary, FL, 32746

  • Home
  • House Hacking
  • Buy
    1. All Listings
    2. Featured Listings
    3. Calculator
  • Sell
    1. Sell My Home
    2. Home Valuation
    3. Market Snapshot
  • Invest
    1. Central Florida Multifamily Listings
    2. Disney Short Term Rentals
  • About
    1. About Us
    2. Contact Us
  • Blogs
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.

Powered by CRM HQ

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

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