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3 bedsNew constructionWith a pool
Homes Under $600K in Winter Park, FL — Page 2
173 listings

Homes Under $600K in Winter Park, FL

Homes Under $600K in Winter Park, FL

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24 of 173 Listings
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Homes Under $600K in Winter Park, FL

24 of 173 Listings

  1. 1695 Lee Rd #C206 — photo24Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

$140,000

2 bd · 1 ba · 881 sqft

1695 Lee Rd #C206, Winter Park, FL

Ingrid Garcia Rodriguez · INVESTMENT REALTY

  • 7786 Fox Knoll Pl — photo55Active

    $410,500

    4 bd · 2 ba · 1,301 sqft

    7786 Fox Knoll Pl, Winter Park, FL

    Eric Senate · NIZZ REALTY INC

  • 173 Scottsdale Sq #173 — photo13Active

    $100,000

    1 bd · 1 ba · 785 sqft

    173 Scottsdale Sq #173, Winter Park, FL

    Paola Jimenez · AXEN REALTY, LLC

  • 1250 S Denning Dr #119 — photo31Active

    $265,000

    2 bd · 2 ba · 908 sqft

    1250 S Denning Dr #119, Winter Park, FL

    Justin McCarthy · FANNIE HILLMAN & ASSOCIATES

  • 1660 Orange Ave — photo61Active

    $479,900

    3 bd · 2 ba · 1,614 sqft

    1660 Orange Ave, Winter Park, FL

    Gaby Murillo · EXP REALTY LLC

  • 2818 Ambergate Rd — photo30Active

    $429,900

    3 bd · 2 ba · 1,398 sqft

    2818 Ambergate Rd, Winter Park, FL

    Noella Tinkler · MARK SPAIN REAL ESTATE

  • 3334 Young St — photo22Active

    $474,900

    3 bd · 2 ba · 1,706 sqft

    3334 Young St, Winter Park, FL

    Jason Alves · EQUITYPRO LLC

  • 3209 Heartwood Ave — photoPrice Reduced12Active

    $439,900

    4 bd · 2 ba · 1,627 sqft

    3209 Heartwood Ave, Winter Park, FL

    James Fitzgibbon · LEDGE REAL ESTATE SOLUTIONS LLC

  • 192 Balfour Dr #2 — photo52Active

    $319,000

    2 bd · 2 ba · 1,287 sqft

    192 Balfour Dr #2, Winter Park, FL

    Tricia Ramsby · BHHS FLORIDA REALTY

  • 7348 Grand Ave — photo16Active

    $285,000

    3 bd · 2 ba · 1,509 sqft

    7348 Grand Ave, Winter Park, FL

    Joseph Doher · BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY

  • 4260 Bear Gully Rd — photo52Active

    $599,000

    4 bd · 4 ba · 2,322 sqft

    4260 Bear Gully Rd, Winter Park, FL

    Alexandre Zapparoli LLC · WRA BUSINESS & REAL ESTATE

  • 7453 Daniel Webster Dr #a5 — photo20Active

    $150,000

    2 bd · 2 ba · 1,063 sqft

    7453 Daniel Webster Dr #a5, Winter Park, FL

    Laila Dkhissi · LA ROSA REALTY PREMIER LLC

  • 1306 S Pennsylvania Ave #5 — photo33Active

    $359,000

    2 bd · 1 ba · 830 sqft

    1306 S Pennsylvania Ave #5, Winter Park, FL

    Lisa Gould · KELLER WILLIAMS WINTER PARK

  • 2463 Grand Teton Cir #2463 — photo19Active

    $249,000

    3 bd · 3 ba · 1,720 sqft

    2463 Grand Teton Cir #2463, Winter Park, FL

    Jessica Polanco · MAINFRAME REAL ESTATE

  • 1386 Clematis Ln — photo2Active

    $427,000

    4 bd · 3 ba · 1,714 sqft

    1386 Clematis Ln, Winter Park, FL

    Michelle Torrente · ROBERT SLACK LLC

  • 4870 Seminole Ave — photo33Active

    $380,000

    3 bd · 2 ba · 1,277 sqft

    4870 Seminole Ave, Winter Park, FL

    Tamara Mazo Ferro · COLDWELL BANKER REALTY

  • 2301 Conifer Ave — photoPrice Reduced28Active

    $405,000

    4 bd · 2 ba · 2,189 sqft

    2301 Conifer Ave, Winter Park, FL

    Gregory Buckley · LOKATION

  • 2383 Sun Valley Cir #2383 — photo33Active

    $234,900

    2 bd · 2 ba · 1,295 sqft

    2383 Sun Valley Cir #2383, Winter Park, FL

    Carmen Aridas · RE/MAX PRIME PROPERTIES

  • 7476 Woodburn Ct #38 — photo28Active

    $170,000

    2 bd · 3 ba · 1,031 sqft

    7476 Woodburn Ct #38, Winter Park, FL

    Habib Fahs · COLDWELL BANKER REALTY

  • 2302 Barbados Dr — photoPrice Reduced35Active

    $275,000

    2 bd · 2 ba · 1,544 sqft

    2302 Barbados Dr, Winter Park, FL

    George Freelove · KELLER WILLIAMS REALTY AT THE PARKS

  • 2136 Linden Rd — photo13Active

    $365,000

    3 bd · 2 ba · 1,185 sqft

    2136 Linden Rd, Winter Park, FL

    Patty Hru · PAM REAL ESTATE

  • 2626 Ambergate Rd — photo20Active

    $380,000

    3 bd · 1 ba · 1,143 sqft

    2626 Ambergate Rd, Winter Park, FL

    Brett Winters · OLDE TOWN BROKERS INC

  • 3020 Nicholson Dr — photo55Active

    $495,000

    4 bd · 2 ba · 1,756 sqft

    3020 Nicholson Dr, Winter Park, FL

    Kristin Duncan · CHARLES RUTENBERG REALTY ORLANDO

  • 3651 N Goldenrod Rd #C109 — photo18Active

    $165,000

    2 bd · 2 ba · 840 sqft

    3651 N Goldenrod Rd #C109, Winter Park, FL

    Valerie Wanzer · REAL ESTATE PROFESSIONALS SE

  • 123…8

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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.