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3 bedsNew constructionWith a pool
Homes Under $2M in Winter Park, FL — Page 6
291 listings

Homes Under $2M in Winter Park, FL

Homes Under $2M in Winter Park, FL

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24 of 291 Listings
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Homes Under $2M in Winter Park, FL

24 of 291 Listings

  1. 1256 Melissa Ct — photo21Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

$660,000

3 bd · 3 ba · 1,690 sqft

1256 Melissa Ct, Winter Park, FL

Wesley Morales · KELLER WILLIAMS REALTY AT THE PARKS

  • 120 Longbranch Rd — photo40Active

    $860,000

    5 bd · 4 ba · 3,284 sqft

    120 Longbranch Rd, Winter Park, FL

    Karen Albright · OPENDOOR BROKERAGE LLC

  • 1842 Puritan Ave — photo28Active

    $419,000

    4 bd · 2 ba · 1,836 sqft

    1842 Puritan Ave, Winter Park, FL

    Karan Jodha · MOBED REALTY, P.A.

  • 2641 Carvell Ct — photoPrice Reduced37Active

    $525,000

    4 bd · 2 ba · 2,126 sqft

    2641 Carvell Ct, Winter Park, FL

    Christina Perez · CHAMBERLAIN REALTY LLC

  • 250 Carolina Ave #205 — photo86Active

    $739,000

    2 bd · 2 ba · 1,311 sqft

    250 Carolina Ave #205, Winter Park, FL

    Troy Hensley · BHHS FLORIDA REALTY

  • 1905 Bonanza Ct — photo26Active

    $520,000

    4 bd · 2 ba · 1,774 sqft

    1905 Bonanza Ct, Winter Park, FL

    Bailey Briscoe · ORCHARD BROKERAGE, LLC

  • 1871 Bryan Ave — photoPrice Reduced28Active

    $599,000

    3 bd · 2 ba · 1,232 sqft

    1871 Bryan Ave, Winter Park, FL

    Nick McKee · KELLER WILLIAMS WINTER PARK

  • 1431 Palm Ave — photoPrice Reduced38Active

    $799,999

    2 bd · 2 ba · 1,540 sqft

    1431 Palm Ave, Winter Park, FL

    Kelsey Payton · ALL REAL ESTATE & INVESTMENTS

  • 7384 Grand Ave — photoPrice Reduced25Active

    $415,000

    3 bd · 2 ba · 1,162 sqft

    7384 Grand Ave, Winter Park, FL

    Joseph Sipp · KELLER WILLIAMS WINTER PARK

  • 2627 Ambergate Rd — photo16Active

    $575,000

    4 bd · 3 ba · 1,745 sqft

    2627 Ambergate Rd, Winter Park, FL

    Steven Thetford · KELLER WILLIAMS WINTER PARK

  • 1955 Eland Ave — photoPrice Reduced19Active

    $410,000

    3 bd · 2 ba · 1,494 sqft

    1955 Eland Ave, Winter Park, FL

    Shelby Kirsch · REAL PROPERTY MANAGEMENT AND REALTY

  • 1652 Berkshire Ave — photoPrice ReducedOpen house Sun, Oct 11 · 2:00 PM29Active

    $449,000

    3 bd · 2 ba · 1,498 sqft

    1652 Berkshire Ave, Winter Park, FL

    Brian Teach · COLDWELL BANKER REALTY

  • 2343 Versailles Ave — photoPrice ReducedOpen house Sat, Oct 10 · 2:00 PM41Active

    $1,699,000

    4 bd · 4 ba · 3,307 sqft

    2343 Versailles Ave, Winter Park, FL

    MaryStuart Day · FANNIE HILLMAN & ASSOCIATES

  • 2477 Tahoe Cir #2477 — photoPrice Reduced24Active

    $247,000

    2 bd · 2 ba · 1,316 sqft

    2477 Tahoe Cir #2477, Winter Park, FL

    Kyle Clark · RE/MAX TOWN & COUNTRY REALTY

  • 5588 Garden Grove Cir — photoPrice Reduced18Active

    $395,000

    3 bd · 2 ba · 1,310 sqft

    5588 Garden Grove Cir, Winter Park, FL

    Victor Nguyen · CHARLES RUTENBERG REALTY ORLANDO

  • 2308 Mulbry Dr — photo12Active

    $1,699,000

    4 bd · 4 ba · 2,530 sqft

    2308 Mulbry Dr, Winter Park, FL

    Brandon Geers · COMPASS FLORIDA LLC

  • 2407 Lafayette Ave — photo35Active

    $1,625,000

    5 bd · 5 ba · 3,133 sqft

    2407 Lafayette Ave, Winter Park, FL

    Lisa Fleming · FANNIE HILLMAN & ASSOCIATES

  • 1071 Aragon Ave — photo34Active

    $575,000

    2 bd · 3 ba · 1,851 sqft

    1071 Aragon Ave, Winter Park, FL

    Greg Vazzana · FANNIE HILLMAN & ASSOCIATES

  • 1840 Bryan Ave — photo53Active

    $1,725,000

    4 bd · 4 ba · 3,727 sqft

    1840 Bryan Ave, Winter Park, FL

    Jennifer Draper · REAL BROKER, LLC

  • 1695 Lee Rd #D107 — photo1Active

    $180,000

    1 bd · 1 ba · 638 sqft

    1695 Lee Rd #D107, Winter Park, FL

    Hoover Yap · PRIMESTATE REALTY, INC.

  • 1122 Wildmeadow Run — photoPrice Reduced37Active

    $660,000

    4 bd · 3 ba · 1,770 sqft

    1122 Wildmeadow Run, Winter Park, FL

    Ken Pozek · REAL BROKER, LLC

  • 5210 Lazy Oaks Dr — photoPrice Reduced37Active

    $279,900

    2 bd · 3 ba · 1,236 sqft

    5210 Lazy Oaks Dr, Winter Park, FL

    Karen Sweat · IHOME REALTY FL LLC

  • 4026 Tenita Dr — photo26Active

    $599,000

    3 bd · 2 ba · 2,031 sqft

    4026 Tenita Dr, Winter Park, FL

    Ruby Davis · RUBY DAVIS, BROKER

  • 2017 Canny CV — photoPrice Reduced27Active

    $379,999

    3 bd · 3 ba · 1,907 sqft

    2017 Canny CV, Winter Park, FL

    Janice Goulder · KELLER WILLIAMS WINTER PARK

  • 1…567…13

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    Thomas O'Leary

    Realty.com

    Lic. #BK3453168

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    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.