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3 bedsNew constructionWith a pool
Homes Under $500K in Winter Park, FL
21 listings

Homes Under $500K in Winter Park, FL

Homes Under $500K in Winter Park, FL

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21 Listings
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Homes Under $500K in Winter Park, FL

21 Listings

  1. 1500 Gay Rd #26-C — photo25Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

$255,000

2 bd · 2 ba · 1,026 sqft

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

Lianna Dangelo · SOTERA LIVING

  • 2020 Leanne Ct — photo28Active

    $479,900

    4 bd · 3 ba · 2,088 sqft

    2020 Leanne Ct, Winter Park, FL

    Ileana Perez · HOUWZER INC

  • 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

  • 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

    $440,000

    4 bd · 2 ba · 2,189 sqft

    2301 Conifer Ave, Winter Park, FL

    Gregory Buckley · LOKATION

  • 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

  • 1250 S Denning Dr #Unit 233 — photo31Active

    $245,000

    2 bd · 2 ba · 913 sqft

    1250 S Denning Dr #Unit 233, Winter Park, FL

    Samuel Kingsford · STOCKWORTH REALTY GROUP

  • 5316 Halyard Ct — photo28Active

    $495,000

    3 bd · 2 ba · 1,380 sqft

    5316 Halyard Ct, Winter Park, FL

    Neil Chetram · LA ROSA REALTY CW PROPERTIES L

  • 3740 Hawthorne Ln — photoPrice Reduced35Active

    $430,000

    3 bd · 2 ba · 1,645 sqft

    3740 Hawthorne Ln, Winter Park, FL

    John Crea · FLORIDA REALTY INVESTMENTS

  • 5409 Albert Dr — photoPrice Reduced15Active

    $405,000

    3 bd · 2 ba · 1,483 sqft

    5409 Albert Dr, Winter Park, FL

    Raul Pino · SOVEREIGN REAL ESTATE GROUP

  • 2703 Tierra Cir — photoPrice Reduced54Active

    $464,000

    3 bd · 2 ba · 1,737 sqft

    2703 Tierra Cir, Winter Park, FL

    Tony Ubaldini · EXP REALTY LLC

  • 885 Carnation Dr — photoPrice Reduced38Active

    $368,000

    4 bd · 2 ba · 1,240 sqft

    885 Carnation Dr, Winter Park, FL

    Tashania Brown · RADIUS REALTY GROUP LLC

  • 151 North Orlando Avenue #142 — photo30Active

    $199,900

    1 bd · 1 ba · 582 sqft

    151 North Orlando Avenue #142, Winter Park, FL

    Chris Creegan · CREEGAN GROUP

  • 1535 Lawndale Cir — photoPrice Reduced15Active

    $420,000

    3 bd · 2 ba · 1,676 sqft

    1535 Lawndale Cir, Winter Park, FL

    Raul Pino · SOVEREIGN REAL ESTATE GROUP

  • 2054 Eastbrook Blvd — photo5Active

    $500,000

    4 bd · 3 ba · 2,031 sqft

    2054 Eastbrook Blvd, Winter Park, FL

    Melissa Stalzer · LPT REALTY, LLC

  • 1092 Eastbrook Blvd — photoPrice Reduced23Active

    $388,000

    3 bd · 2 ba · 1,122 sqft

    1092 Eastbrook Blvd, Winter Park, FL

    Eva Firios · JC FLORIDA REALTY LLC

  • 501 Heritage Blvd — photoPrice Reduced20Active

    $419,000

    4 bd · 2 ba · 1,376 sqft

    501 Heritage Blvd, Winter Park, FL

    Bernardo Carrasquel · EXP REALTY LLC

  • 151 N Orlando Ave #118 — photo20Active

    $299,999

    2 bd · 1 ba · 710 sqft

    151 N Orlando Ave #118, Winter Park, FL

    Adriana Montes · FLORIDA DREAMS REALTY GRP INC

  • 205 Lewfield Cir #205 — photoPrice Reduced37Active

    $182,900

    2 bd · 2 ba · 927 sqft

    205 Lewfield Cir #205, Winter Park, FL

    Eimi Moreno Carrera · LPT REALTY, LLC

  • 2217 Sussex Rd — photoPrice Reduced34Active

    $485,000

    4 bd · 2 ba · 2,092 sqft

    2217 Sussex Rd, Winter Park, FL

    Justin Hilton · PREFERRED REAL ESTATE BROKERS

  • 5331 Oak Ct — photo41Active

    $460,000

    3 bd · 2 ba · 1,263 sqft

    5331 Oak Ct, Winter Park, FL

    Nataliya Voroshylo Hylton · CHARLES RUTENBERG REALTY ORLANDO

  • Explore Winter Park homes

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    • Homes Under $200K
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    • Homes Under $800K
    • Homes Under $900K
    • Homes Under $1M
    • Homes Under $1.25M
    • Homes Under $1.5M
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    • Luxury Homes

    By bedrooms

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    By type

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    By feature

    • New Construction Homes
    • Homes with a Pool
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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 · This period is still settling

    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 23, 2026

    Median sale price
    $602,500$441,750–$1,016,350 typical range
    Price per sq. ft.
    $358
    Sales
    78
    Paid in cash
    46.2%

    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
    38.1%

    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.