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3 bedsNew constructionWith a pool
116 listings

Homes with a Pool in Winter Park, FL

Homes with a Pool in Winter Park, FL

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24 of 116 Listings
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Homes with a Pool in Winter Park, FL

24 of 116 Listings

  1. 3409 Ferndell Dr — photoOpen house Sat, Oct 17 · 11:00 AM30
Active

$415,900

3 bd · 2 ba · 1,412 sqft

3409 Ferndell Dr, Winter Park, FL

Veronica Lewis · LPT REALTY, LLC

  • 1931 Aster Dr — photoOpen house Sat, Oct 17 · 12:00 PM30Active

    $575,000

    3 bd · 3 ba · 2,031 sqft

    1931 Aster Dr, Winter Park, FL

    Farah Bloom · KELLER WILLIAMS WINTER PARK

  • 1011 McKean Cir — photoNew70Active

    $6,000,000

    5 bd · 7 ba · 4,806 sqft

    1011 McKean Cir, Winter Park, FL

    Clay Wooten · UNITED REAL ESTATE PREFERRED

  • 346 Elkhorn Ct — photoNewOpen house Sun, Oct 18 · 12:00 PM37Active

    $575,000

    4 bd · 2 ba · 1,891 sqft

    346 Elkhorn Ct, Winter Park, FL

    Natalie Amento · FLORIDA REALTY INVESTMENTS

  • 1411 Devon Rd — photoOpen house Sat, Oct 17 · 11:00 AM47Active

    $950,000

    2 bd · 2 ba · 1,947 sqft

    1411 Devon Rd, Winter Park, FL

    Harif Hazera LLC · PREMIER SOTHEBY'S INTL. REALTY

  • 2174 Shadyhill Ter — photo41Active

    $529,900

    4 bd · 3 ba · 1,983 sqft

    2174 Shadyhill Ter, Winter Park, FL

    Ahmad Karain · SET HOMES REALTY LLC

  • 1751 Glencoe Rd — photoNewOpen house Sat, Oct 17 · 11:00 AM67Active

    $3,390,000

    5 bd · 7 ba · 4,520 sqft

    1751 Glencoe Rd, Winter Park, FL

    Christopher Christensen · ONE LUXURY INTERNATIONAL LLC

  • 2234 Howard Dr — photo17Active

    $2,295,000

    4 bd · 6 ba · 3,295 sqft

    2234 Howard Dr, Winter Park, FL

    Raquel Elliott · COLDWELL BANKER REALTY

  • 1737 Indiana Ave — photo38Active

    $1,399,900

    4 bd · 4 ba · 2,984 sqft

    1737 Indiana Ave, Winter Park, FL

    Tori Nguyen · LOKATION

  • 731 Bongart Rd — photo51Active

    $519,900

    4 bd · 3 ba · 1,842 sqft

    731 Bongart Rd, Winter Park, FL

    Steven Koleno · BEYCOME OF FLORIDA LLC

  • 1500 Gay Rd #26-C — photo25Active

    $255,000

    2 bd · 2 ba · 1,026 sqft

    1500 Gay Rd #26-C, Winter Park, FL

    Lianna Dangelo · SOTERA LIVING

  • 2823 Parkland Circle — photoOpen house Sat, Oct 17 · 12:00 PM46Active

    $3,250,000

    5 bd · 6 ba · 4,459 sqft

    2823 Parkland Circle, Winter Park, FL

    Sandra Cuba · PREMIER SOTHEBY'S INTL. REALTY

  • 2020 Leanne Ct — photo28Active

    $479,900

    4 bd · 3 ba · 2,088 sqft

    2020 Leanne Ct, Winter Park, FL

    Ileana Perez · HOUWZER INC

  • 518 Gilbert Rd — photo48Active

    $649,000

    3 bd · 2 ba · 1,573 sqft

    518 Gilbert Rd, Winter Park, FL

    Monika Kenney · PALMANO GROUP RE BROKERAGE LLC

  • 2613 Lafayette Ave — photo12Active

    $1,699,900

    4 bd · 4 ba · 2,661 sqft

    2613 Lafayette Ave, Winter Park, FL

    Matt Tomaszewski · CORCORAN PREMIER REALTY

  • 2322 Woodcrest Dr — photoOpen house Sun, Oct 18 · 12:00 PM28Active

    $675,000

    4 bd · 2 ba · 1,650 sqft

    2322 Woodcrest Dr, Winter Park, FL

    Jill Healey · KELLER WILLIAMS WINTER PARK

  • 918 Enclave Pl — photo8Active

    $2,125,000

    5 bd · 5 ba · 3,713 sqft

    918 Enclave Pl, Winter Park, FL

    Laura Earl · CORCORAN PREMIER REALTY

  • 2119 Howard Dr — photo11Active

    $3,195,000

    5 bd · 6 ba · 4,139 sqft

    2119 Howard Dr, Winter Park, FL

    Laura Earl · CORCORAN PREMIER REALTY

  • 2007 Edwin Blvd — photo4Active

    $1,995,000

    4 bd · 4 ba · 3,314 sqft

    2007 Edwin Blvd, Winter Park, FL

    Angela Rodriguez · DREAM FINDERS REALTY GROUP CORP

  • 513 Dunraven Dr — photo21Active

    $1,950,000

    5 bd · 5 ba · 3,560 sqft

    513 Dunraven Dr, Winter Park, FL

    Alison Mosley · PREMIER SOTHEBY'S INTL. REALTY

  • 1003 Golfside Dr — photo28Active

    $769,900

    3 bd · 3 ba · 2,145 sqft

    1003 Golfside Dr, Winter Park, FL

    Lina Paeres · QP HOMES REALTY LLC

  • 555 E Lake Sue Ave — photo96Active

    $2,095,000

    4 bd · 4 ba · 3,776 sqft

    555 E Lake Sue Ave, Winter Park, FL

    Claudia Davidson · KELLER WILLIAMS WINTER PARK

  • 698 N New York Ave — photo52Active

    $6,195,000

    5 bd · 6 ba · 5,096 sqft

    698 N New York Ave, Winter Park, FL

    Mick Night · PREMIER SOTHEBY'S INTL. REALTY

  • 2614 Parkland Dr — photo55Active

    $1,890,000

    4 bd · 4 ba · 3,307 sqft

    2614 Parkland Dr, Winter Park, FL

    Ryan Gaston · JW GASTON LLC

  • 12…5

    About Homes with a Pool in Winter Park, FL

    Homes with a Pool in Winter Park, FL: 116 active listings as of October 16, 2026, 20:08 UTC.

    Property types among these 116 listings, by the property type each listing’s MLS reports, spelled as the MLS spells it. Types with fewer than 5 listings, and listings whose MLS reports no type, are not shown, so the shares can total less than 100%.
    Property typeListingsShare
    Single Family Residence11094.8%
    Condominium65.2%

    Explore Winter Park homes

    By price

    • Homes Under $200K
    • Homes Under $300K
    • Homes Under $400K
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    The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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    Listing data & MLS disclosures

    Stellar MLS
    Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Listing information is provided for consumers? personal, non-commercial use, solely to identify prospective properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Information deemed reliable but not guaranteed. Copyright © 2026 MLS GRID. All Rights Reserved.

    Winter Park, FL community profile

    Population
    31,855
    Median income
    $98,252
    Housing units
    15,404
    People per sq. mi.
    1,409.5
    Area
    22.6 sq. mi.

    Source: HJN community data

    Winter Park housing market

    September 2026

    Winter Park 12-month median sale price trend

    Selling at 97.9% of asking price

    Buyers here are paying below asking. MLS · 84 sales · as of Sep 30, 2026

    Homes that sold · County records, as of Sep 28, 2026

    Median sale price
    $565,000$410,000–$952,600 typical range
    Price per sq. ft.
    $342
    Sales
    92
    Paid in cash
    44.6%

    Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

    Median list price
    $630,000
    Homes for sale
    383
    Median days on market
    18 days

    Price trend · Assessor repeat sales, as of Sep 30, 2026

    Year-over-year
    28.1%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 11, 2026

    Median home size
    1,731 sq. ft.
    Homes with a Pool in Winter Park, FL