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    ZIP Code: 32789
    Map
    249 Properties Available

    249 Properties Available

    • Newest Listings
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    • Price-Low To High
    • Beds (Most)
    • Baths (Most)
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    1621 CHESTNUT AVE, Winter Park, FL 32789
    1/35
    New

    $899,000

    3 Beds3 Baths2,022 SqFt

    1621 CHESTNUT AVE, Winter Park, FL 32789

    Listed by Kelly Price KELLY PRICE & COMPANY LLC

    Stellar MLS
    565 HUNTINGTON AVE #565, Winter Park, FL 32789
    1/27
    Open Sat 12PM-2PM

    $635,000

    3 Beds3 Baths2,015 SqFt

    565 HUNTINGTON AVE #565, Winter Park, FL 32789

    Listed by Olivia Maxwell FANNIE HILLMAN & ASSOCIATES

    Stellar MLS
    720 PANSY AVE, Winter Park, FL 32789
    1/58
    Coming Soon

    $1,350,000

    3 Beds4 Baths2,191 SqFt

    720 PANSY AVE, Winter Park, FL 32789

    Listed by Nick McKee KELLER WILLIAMS WINTER PARK

    Stellar MLS
    1278 S PENNSYLVANIA AVE #13, Winter Park, FL 32789
    1/16
    New

    $799,000

    3 Beds3 Baths1,957 SqFt

    1278 S PENNSYLVANIA AVE #13, Winter Park, FL 32789

    Listed by Nancy Merriam PREMIER SOTHEBY'S INTL. REALTY

    Stellar MLS
    1417 WILLIAMS DR, Winter Park, FL 32789
    1/55
    Open Sat 12PM-3PM

    $3,999,000

    5 Beds6 Baths4,891 SqFt

    1417 WILLIAMS DR, Winter Park, FL 32789

    Listed by Christopher Christensen ONE LUXURY INTERNATIONAL LLC

    Stellar MLS
    1256 MELISSA CT, Winter Park, FL 32789
    1/20
    New

    $660,000

    3 Beds3 Baths1,690 SqFt

    1256 MELISSA CT, Winter Park, FL 32789

    Listed by Wesley Morales KELLER WILLIAMS REALTY AT THE PARKS

    Stellar MLS
    250 CAROLINA AVE #205, Winter Park, FL 32789
    1/86
    New
    3D

    $739,000

    2 Beds2 Baths1,311 SqFt

    250 CAROLINA AVE #205, Winter Park, FL 32789

    Listed by Troy Hensley BHHS FLORIDA REALTY

    Stellar MLS
    1409 SUNSET DR, Winter Park, FL 32789
    1/33
    New

    $669,000

    2 Beds2 Baths1,107 SqFt

    1409 SUNSET DR, Winter Park, FL 32789

    Listed by TJ Tuzzeo KONA REALTY SERVICES LLC

    Stellar MLS
    1871 BRYAN AVE, Winter Park, FL 32789
    1/28
    New

    $625,000

    3 Beds2 Baths1,232 SqFt

    1871 BRYAN AVE, Winter Park, FL 32789

    Listed by Nick McKee KELLER WILLIAMS WINTER PARK

    Stellar MLS
    2183 CRANDON AVE, Winter Park, FL 32789
    1/28
    New

    $499,000

    4 Beds2 Baths1,200 SqFt

    2183 CRANDON AVE, Winter Park, FL 32789

    Listed by Walkidia Reyes, PA REAL PROPERTY MANAGEMENT AND REALTY

    Stellar MLS
    609 S PHELPS AVE, Winter Park, FL 32789
    Active Under Contract

    $2,800,000

    5 Beds5 Baths4,018 SqFt

    609 S PHELPS AVE, Winter Park, FL 32789

    Listed by Christopher Christensen ONE LUXURY INTERNATIONAL LLC

    Stellar MLS
    648 WORTHINGTON DR, Winter Park, FL 32789
    1/8
    New

    $2,700,000

    5 Beds5 Baths3,588 SqFt

    648 WORTHINGTON DR, Winter Park, FL 32789

    Listed by Christopher Christensen ONE LUXURY INTERNATIONAL LLC

    Stellar MLS
    948 POINCIANA LN, Winter Park, FL 32789
    1/41
    New

    $2,750,000

    4 Beds5 Baths3,676 SqFt

    948 POINCIANA LN, Winter Park, FL 32789

    Listed by Mick Night PREMIER SOTHEBY'S INTL. REALTY

    Stellar MLS
    1250 S DENNING DR #Unit 233, Winter Park, FL 32789
    1/27
    Coming Soon

    $245,000

    2 Beds2 Baths913 SqFt

    1250 S DENNING DR #Unit 233, Winter Park, FL 32789

    Listed by Samuel Kingsford STOCKWORTH REALTY GROUP

    Stellar MLS
    1431 PALM AVE, Winter Park, FL 32789
    1/38
    New

    $850,000

    2 Beds2 Baths1,540 SqFt

    1431 PALM AVE, Winter Park, FL 32789

    Listed by Kelsey Payton ALL REAL ESTATE & INVESTMENTS

    Stellar MLS
    1652 BERKSHIRE AVE, Winter Park, FL 32789
    1/29
    Open Sun 2PM-4PM

    $549,900

    3 Beds2 Baths1,498 SqFt

    1652 BERKSHIRE AVE, Winter Park, FL 32789

    Listed by Brian Teach COLDWELL BANKER REALTY

    Stellar MLS
    1955 ELAND AVE, Winter Park, FL 32789
    1/19
    New

    $439,000

    3 Beds2 Baths1,494 SqFt

    1955 ELAND AVE, Winter Park, FL 32789

    Listed by Shelby Kirsch REAL PROPERTY MANAGEMENT AND REALTY

    Stellar MLS
    2343 VERSAILLES AVE, Winter Park, FL 32789
    1/43
    Open Sat 1PM-4PM

    $1,865,000

    4 Beds4 Baths3,307 SqFt

    2343 VERSAILLES AVE, Winter Park, FL 32789

    Listed by MaryStuart Day FANNIE HILLMAN & ASSOCIATES

    Stellar MLS
    620 VIRGINIA DR, Winter Park, FL 32789
    1/11
    New

    $3,890,000

    6 Beds5 Baths4,677 SqFt

    620 VIRGINIA DR, Winter Park, FL 32789

    Listed by Julie Christensen ONE LUXURY INTERNATIONAL LLC

    Stellar MLS
    950 S KENTUCKY AVE, Winter Park, FL 32789
    1/71
    New
    3D

    $799,000

    4 Beds3 Baths2,155 SqFt

    950 S KENTUCKY AVE, Winter Park, FL 32789

    Listed by Gwen Flynn COLDWELL BANKER REALTY

    Stellar MLS
    1333 S DENNING DR, Winter Park, FL 32789
    1/34
    Pending

    $299,000

    2 Beds1 Bath702 SqFt

    1333 S DENNING DR, Winter Park, FL 32789

    Listed by Steven Ritz KELLER WILLIAMS WINTER PARK

    Stellar MLS
    150 E READING WAY, Winter Park, FL 32789
    1/21
    New

    $1,495,000

    0.29 Acres

    150 E READING WAY, Winter Park, FL 32789

    Listed by Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

    Stellar MLS
    2308 MULBRY DR, Winter Park, FL 32789
    1/12
    New

    $1,699,000

    4 Beds4 Baths2,530 SqFt

    2308 MULBRY DR, Winter Park, FL 32789

    Listed by Brandon Geers COMPASS FLORIDA LLC

    Stellar MLS
    2407 LAFAYETTE AVE, Winter Park, FL 32789
    1/35
    New

    $1,625,000

    5 Beds5 Baths3,133 SqFt

    2407 LAFAYETTE AVE, Winter Park, FL 32789

    Listed by Lisa Fleming FANNIE HILLMAN & ASSOCIATES

    Stellar MLS
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    Round Table Realty License ID: CQ1036724

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    1637 Racetrack Rd, Jacksonville, FL 32259

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    RoundTableRealty_logoWhiteLetters
        Home
        Buy
        1. Neighborhoods
        2. Community and Area Guides
        3. New Construction
        4. Featured Listings
        5. Buyer Representation
        6. Relocation to Northeast Florida
        7. Mortgage Payment Calculator
        8. International Investors
        9. Submit an Escrow Deposit
        Sell
        1. Seller's Guide
        2. Sell My Home
        3. Rent versus Sell
        4. Home Valuation
        5. Sold Listings
        6. Market Snapshot
        7. Preferred Vendors
        About
        1. About RTR
        2. Round Table Realty Agents
        3. Contact
        4. Blogs
        5. Reviews
        Join RTR
        Jacksonville Property Management
        Partner Lenders
    Round Table Realty

    Round Table Realty License ID: CQ1036724

    +1(904) 469-7653 admin@roundtablerealty.com

    1637 Racetrack Rd, Jacksonville, FL 32259

    Mobile phone numbers, SMS opt-in data, and messaging consent are not shared, sold, rented, or provided to third parties or affiliates for marketing or promotional purposes. 

    Get My App

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

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

    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.