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3 bedsNew constructionWith a pool
Homes Under $1.5M in Winter Park, FL
263 listings

Homes Under $1.5M in Winter Park, FL

Homes Under $1.5M in Winter Park, FL

Show Map
24 of 263 Listings
Map

Homes Under $1.5M in Winter Park, FL

24 of 263 Listings

  1. 3409 Ferndell Dr — photo31Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

$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

  • 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

  • 216 Lewfield Cir #216 — photoNew25Active

    $230,000

    3 bd · 2 ba · 1,268 sqft

    216 Lewfield Cir #216, Winter Park, FL

    Vicki Bray-Fagan, LLC · WATSON REALTY CORP

  • 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

  • 2356 Shadowland Loop — photoNewOpen house Sun, Oct 18 · 2:00 PM42Active

    $460,000

    3 bd · 3 ba · 2,076 sqft

    2356 Shadowland Loop, Winter Park, FL

    Lisa Gould · KELLER WILLIAMS WINTER PARK

  • 2219 Winter Woods Blvd — photoNew23Active

    $479,999

    3 bd · 3 ba · 1,776 sqft

    2219 Winter Woods Blvd, Winter Park, FL

    Bryan Rhoads · LKV REALTY, LLC

  • 1399 Aloma Ave — photoNew30Active

    $575,000

    3 bd · 2 ba · 1,804 sqft

    1399 Aloma Ave, Winter Park, FL

    Nancy Bagby · FANNIE HILLMAN & ASSOCIATES

  • 1611 Chestnut Ave — photo55Active

    $985,000

    4 bd · 4 ba · 2,916 sqft

    1611 Chestnut Ave, Winter Park, FL

    Gunel Aydamirli · OLYMPUS EXECUTIVE REALTY INC

  • 1320 Buckingham Rd — photo20Active

    $449,000

    3 bd · 2 ba · 1,388 sqft

    1320 Buckingham Rd, Winter Park, FL

    Matthew Brown · PALLADIUM INVESTMENTS INC

  • 1407 Broad Wing Ln — photo41Active

    $491,000

    3 bd · 3 ba · 2,308 sqft

    1407 Broad Wing Ln, Winter Park, FL

    Roger Michaels · R MICHAELS REALTY LLC

  • 1462 Siciliano Pt — photo14Active

    $325,000

    3 bd · 3 ba · 1,628 sqft

    1462 Siciliano Pt, Winter Park, FL

    Selena Rivera · NONA LEGACY POWERED BY LA ROSA

  • 1737 Indiana Ave — photo38Active

    $1,399,900

    4 bd · 4 ba · 2,984 sqft

    1737 Indiana Ave, Winter Park, FL

    Tori Nguyen · LOKATION

  • 4882 Tangerine Ave #4882 — photo28Active

    $185,000

    2 bd · 2 ba · 1,281 sqft

    4882 Tangerine Ave #4882, Winter Park, FL

    Greg Sibley · SIMPLYSOLD REAL ESTATE PREMIER

  • 700 Melrose Ave #M23 — photo29Active

    $354,000

    2 bd · 2 ba · 1,074 sqft

    700 Melrose Ave #M23, Winter Park, FL

    Linda Jokbengboon · COMPASS FLORIDA LLC

  • 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

  • 2228 King Charles Ct — photoOpen house Sat, Oct 17 · 11:00 AM35Active

    $575,000

    4 bd · 3 ba · 2,551 sqft

    2228 King Charles Ct, Winter Park, FL

    Heather Pryor · KELLER WILLIAMS ADVANTAGE REALTY

  • 640 N Park Ave #3 — photo42Active

    $745,000

    2 bd · 2 ba · 897 sqft

    640 N Park Ave #3, Winter Park, FL

    Erika Beerbower · FANNIE HILLMAN & ASSOCIATES

  • 3416 Arbutus Ln — photoPrice Reduced20Active

    $379,900

    4 bd · 3 ba · 1,421 sqft

    3416 Arbutus Ln, Winter Park, FL

    Jorge Schlaefli · GPS REALTY GROUP

  • 2067 Poinciana Rd — photoOpen house Sat, Oct 17 · 11:00 AM90Active

    $560,000

    4 bd · 2 ba · 2,352 sqft

    2067 Poinciana Rd, Winter Park, FL

    Brandon Williams · WATSON REALTY CORP

  • 1602 Alabama Dr #107 — photo33Active

    $1,150,000

    2 bd · 2 ba · 993 sqft

    1602 Alabama Dr #107, Winter Park, FL

    Valerie Leary · CORCORAN PREMIER REALTY

  • 2020 Leanne Ct — photo28Active

    $479,900

    4 bd · 3 ba · 2,088 sqft

    2020 Leanne Ct, Winter Park, FL

    Ileana Perez · HOUWZER INC

  • 3307 Amber Wood Way #106 — photo28Active

    $169,000

    2 bd · 3 ba · 1,031 sqft

    3307 Amber Wood Way #106, Winter Park, FL

    Bryan Burns · RE/MAX DOWNTOWN

  • 12…11

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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #BK3453168

    Call Thomas

    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.