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3 bedsNew constructionWith a pool
Homes Under $2M in Winter Park, FL — Page 12
290 listings

Homes Under $2M in Winter Park, FL

Homes Under $2M in Winter Park, FL

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24 of 290 Listings
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Homes Under $2M in Winter Park, FL

24 of 290 Listings

  1. 1521 Heron Wood Pl — photoPrice Reduced74

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas
Active

$829,500

4 bd · 2 ba · 3,950 sqft

1521 Heron Wood Pl, Winter Park, FL

Ronald Trotter · RE/MAX INNOVATION

  • 630 Killarney Bay Ct #3 — photoPrice Reduced55Active

    $459,900

    2 bd · 3 ba · 1,428 sqft

    630 Killarney Bay Ct #3, Winter Park, FL

    Anthony Consalvo · FLORIDA ONE REAL ESTATE LLC

  • 1751 Goodrich Ave — photoPrice Reduced50Active

    $1,380,000

    4 bd · 4 ba · 2,170 sqft

    1751 Goodrich Ave, Winter Park, FL

    Stephanie Baldner · EXP REALTY LLC

  • 330 Elkhorn Ct — photoPrice Reduced30Active

    $534,900

    3 bd · 2 ba · 1,570 sqft

    330 Elkhorn Ct, Winter Park, FL

    Neil Chetram · LA ROSA REALTY CW PROPERTIES L

  • 432 W Swoope Ave — photoPrice Reduced20Active

    $680,000

    4 bd · 4 ba · 2,664 sqft

    432 W Swoope Ave, Winter Park, FL

    Thomas Bonner · COLDWELL BANKER RESIDENTIAL RE

  • 3220 Netherwood Dr — photoPrice Reduced18Active

    $268,950

    2 bd · 2 ba · 1,036 sqft

    3220 Netherwood Dr, Winter Park, FL

    Nimrah Ashraf · THE FIRM RE

  • 1840 Anzle Ave — photo12Active

    $1,750,000

    4 bd · 3 ba · 2,350 sqft

    1840 Anzle Ave, Winter Park, FL

    Oscar Rodriguez · B LIVE COMMERCIAL AND RESIDENTIAL REAL ESTATE

  • 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

  • 2231 Nairn Dr — photo19Active

    $499,000

    3 bd · 2 ba · 1,088 sqft

    2231 Nairn Dr, Winter Park, FL

    David Auerbach · PARK TOWN REAL ESTATE LLC

  • 230 Strathy Ln — photo12Active

    $499,000

    2 bd · 1 ba · 920 sqft

    230 Strathy Ln, Winter Park, FL

    David Auerbach · PARK TOWN REAL ESTATE LLC

  • 2500 Lee Rd. #222 — photoPrice Reduced26Active

    $184,400

    1 bd · 1 ba · 645 sqft

    2500 Lee Rd. #222, Winter Park, FL

    Christine Bouchard · HOMESMART

  • 560 Ololu Dr — photoPrice Reduced29Active

    $899,000

    2 bd · 2 ba · 1,086 sqft

    560 Ololu Dr, Winter Park, FL

    Tiffany Yates · COMPASS FLORIDA LLC

  • 151 N Orlando Ave ##115 — photoPrice Reduced23Active

    $285,000

    2 bd · 1 ba · 710 sqft

    151 N Orlando Ave ##115, Winter Park, FL

    Chris Creegan · CREEGAN GROUP

  • 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

  • 2612 Roxbury Rd — photoPrice Reduced40Active

    $605,000

    5 bd · 3 ba · 2,472 sqft

    2612 Roxbury Rd, Winter Park, FL

    Laura Mcadams · EXP REALTY LLC

  • 311 Scottsdale Sq #311 — photoPrice Reduced8Active

    $109,400

    1 bd · 1 ba · 785 sqft

    311 Scottsdale Sq #311, Winter Park, FL

    Omar Rodriguez · EMPIRE NETWORK REALTY

  • 2336 Sun Valley Cir #Bldg 20 — photoPrice Reduced12Active

    $285,000

    2 bd · 2 ba · 1,669 sqft

    2336 Sun Valley Cir #Bldg 20, Winter Park, FL

    Lizzie Beaudoin · PR REAL ESTATE SERVICES

  • 2948 Antique Oaks Cir #94 — photo33Active

    $150,000

    1 bd · 1 ba · 749 sqft

    2948 Antique Oaks Cir #94, Winter Park, FL

    Santiago Silva · THE PAMPAS REAL ESTATE GROUP, LLC.

  • 311 E Morse Blvd #7-11 — photoPrice Reduced25Active

    $279,000

    1 bd · 1 ba · 570 sqft

    311 E Morse Blvd #7-11, Winter Park, FL

    Mary Colton · FANNIE HILLMAN & ASSOCIATES

  • 1849 Viburnum Ln — photoPrice Reduced27Active

    $389,900

    4 bd · 2 ba · 1,627 sqft

    1849 Viburnum Ln, Winter Park, FL

    Lesly Hijar · REAL BROKER, LLC

  • 2758 Banchory Rd — photoPrice Reduced38Active

    $619,500

    3 bd · 3 ba · 1,539 sqft

    2758 Banchory Rd, Winter Park, FL

    Erwin Vargas · MR VARGAS PROPERTY MANAGEMENT LLC

  • 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

  • 3370 Cedar Springs Pl #156 — photoPrice Reduced26Active

    $179,990

    2 bd · 3 ba · 1,031 sqft

    3370 Cedar Springs Pl #156, Winter Park, FL

    Wendy Lin · SPRINGHILL PROPERTIES LLC

  • 1…111213

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    Lic. #BK3453168

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    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.