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3 bedsNew constructionWith a pool
Homes Under $2M in Winter Park, FL — Page 7
292 listings

Homes Under $2M in Winter Park, FL

Homes Under $2M in Winter Park, FL

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24 of 292 Listings
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Homes Under $2M in Winter Park, FL

24 of 292 Listings

  1. 4026 Tenita Dr — photo26Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

$599,000

3 bd · 2 ba · 2,031 sqft

4026 Tenita Dr, Winter Park, FL

Ruby Davis · RUBY DAVIS, BROKER

  • 7413 Belle River Ct #3 — photoPrice Reduced11Active

    $214,900

    3 bd · 3 ba · 1,151 sqft

    7413 Belle River Ct #3, Winter Park, FL

    Ivan Tobon · OUTLET REALTY

  • 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

  • 2667 Cochise Trl — photoPrice Reduced92Active

    $985,000

    4 bd · 3 ba · 2,868 sqft

    2667 Cochise Trl, Winter Park, FL

    Beverley Kistler · COLDWELL BANKER REALTY

  • 1927 S Lakemont Ave — photoPrice ReducedOpen house Sat, Oct 10 · 1:00 PM48Active

    $915,000

    3 bd · 4 ba · 2,093 sqft

    1927 S Lakemont Ave, Winter Park, FL

    Abby Green · IAD REAL ESTATE

  • 1061 Aragon Ave #1061 — photo19Active

    $510,000

    3 bd · 3 ba · 1,669 sqft

    1061 Aragon Ave #1061, Winter Park, FL

    Lois Ann Cox, PA · WATSON REALTY CORP

  • 1000 S Semoran Blvd #302 — photoPrice Reduced15Active

    $105,000

    1 bd · 1 ba · 796 sqft

    1000 S Semoran Blvd #302, Winter Park, FL

    Amaal Barakat · KELLER WILLIAMS ADVANTAGE III

  • 433 Gilbert Rd — photoPrice ReducedOpen house Sun, Oct 11 · 12:00 PM36Active

    $669,900

    3 bd · 2 ba · 1,800 sqft

    433 Gilbert Rd, Winter Park, FL

    Amy Turner · KELLER WILLIAMS WINTER PARK

  • 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

  • 2475 Tahoe Cir — photoPrice Reduced29Active

    $268,000

    2 bd · 2 ba · 1,295 sqft

    2475 Tahoe Cir, Winter Park, FL

    Sarah Doyer · COLDWELL BANKER REALTY

  • 777 Halifax Ave — photoPrice Reduced48Active

    $1,449,000

    5 bd · 5 ba · 3,109 sqft

    777 Halifax Ave, Winter Park, FL

    Jared Smith · SAFFORD REAL ESTATE LLC

  • 1886 Clematis Ln — photo29Active

    $425,000

    3 bd · 2 ba · 1,238 sqft

    1886 Clematis Ln, Winter Park, FL

    Steven Greening · EXP REALTY LLC

  • 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

  • 3562 Bougainvillea Dr — photoPrice Reduced27Active

    $334,000

    3 bd · 2 ba · 1,149 sqft

    3562 Bougainvillea Dr, Winter Park, FL

    Tania Crandall · SHORESTONE PROPERTY GROUP

  • 724 Monmouth Way — photoPrice Reduced29Active

    $798,000

    5 bd · 4 ba · 2,832 sqft

    724 Monmouth Way, Winter Park, FL

    Cardiff Howell · CENTRAL TOWER PROPERTIES

  • 1000 S Semoran Blvd #305 — photoPrice Reduced22Active

    $115,000

    1 bd · 1 ba · 735 sqft

    1000 S Semoran Blvd #305, Winter Park, FL

    Melissa Vance · MAINFRAME REAL ESTATE

  • 2703 Tierra Cir — photoPrice ReducedOpen house Sat, Oct 10 · 11:00 AM54Active

    $464,000

    3 bd · 2 ba · 1,737 sqft

    2703 Tierra Cir, Winter Park, FL

    Tony Ubaldini · EXP REALTY LLC

  • 2033 Canny CV — photoPrice Reduced55Active

    $389,000

    3 bd · 3 ba · 1,907 sqft

    2033 Canny CV, Winter Park, FL

    Monica Puche · LPT REALTY, LLC

  • 281 Brewer Ave — photo49Active

    $1,800,000

    5 bd · 5 ba · 4,029 sqft

    281 Brewer Ave, Winter Park, FL

    John Henthorn · HENTHORN REAL ESTATE

  • 2568 Lotafun Ave — photoPrice Reduced25Active

    $395,000

    3 bd · 2 ba · 1,201 sqft

    2568 Lotafun Ave, Winter Park, FL

    Randall Wolber, Jr · SIMPLE FEE LISTINGS LLC

  • 230 Killarney Dr — photo13Active

    $1,250,000

    4 bd · 1 ba · 1,260 sqft

    230 Killarney Dr, Winter Park, FL

    Shandy Ortiz · PREMIER SOTHEBYS INT'L REALTY

  • 240 Killarney Dr — photo13Active

    $1,275,000

    3 bd · 3 ba · 1,329 sqft

    240 Killarney Dr, Winter Park, FL

    Shandy Ortiz · PREMIER SOTHEBYS INT'L REALTY

  • 1562 Arbor Park Dr — photo49Active

    $775,000

    4 bd · 3 ba · 1,899 sqft

    1562 Arbor Park Dr, Winter Park, FL

    Abby Greenberg · COMPASS FLORIDA LLC

  • 2526 Passamonte Dr #10F — photo10Active

    $335,000

    3 bd · 3 ba · 1,790 sqft

    2526 Passamonte Dr #10F, Winter Park, FL

    Kathi Thomas · LEGACY CORNERSTONE INC

  • 1…678…13

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    Your local brokerage

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    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.