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3 bedsNew constructionWith a pool
Townhomes in Winter Park, FL
33 listings

Townhomes in Winter Park, FL

Townhomes in Winter Park, FL

Show Map
24 of 33 Listings
Map

Townhomes in Winter Park, FL

24 of 33 Listings

  1. 1462 Siciliano Pt — photoNew14

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas
Active

$325,000

3 bd · 3 ba · 1,628 sqft

1462 Siciliano Pt, Winter Park, FL

Selena Rivera · NONA LEGACY POWERED BY LA ROSA

  • 3307 Amber Wood Way #106 — photo28Active

    $169,000

    2 bd · 3 ba · 1,031 sqft

    3307 Amber Wood Way #106, Winter Park, FL

    Bryan Burns · RE/MAX DOWNTOWN

  • 7560 Aloma Pines Ct — photoPrice Reduced23Active

    $355,000

    3 bd · 3 ba · 1,866 sqft

    7560 Aloma Pines Ct, Winter Park, FL

    Jessica Macias · KELLER WILLIAMS ADVANTAGE III

  • 7498 Aloma Pines Ct — photo39Active

    $364,900

    3 bd · 3 ba · 1,872 sqft

    7498 Aloma Pines Ct, Winter Park, FL

    Marian Coaxum · KELLER WILLIAMS REALTY AT THE PARKS

  • 1256 S Pennsylvania Ave #9 — photo46Active

    $950,000

    3 bd · 3 ba · 1,957 sqft

    1256 S Pennsylvania Ave #9, Winter Park, FL

    Drew Henner · PREMIER SOTHEBY'S INTL. REALTY

  • 504 W Swoope Ave — photo32Active

    $1,300,000

    3 bd · 3 ba · 2,563 sqft

    504 W Swoope Ave, Winter Park, FL

    Jennifer Sloan · COMPASS FLORIDA LLC

  • 2302 Barbados Dr — photoPrice ReducedOpen house Sun, Oct 11 · 12:00 PM35Active

    $275,000

    2 bd · 2 ba · 1,544 sqft

    2302 Barbados Dr, Winter Park, FL

    George Freelove · KELLER WILLIAMS REALTY AT THE PARKS

  • 2275 Island Run — photo29Active

    $299,990

    3 bd · 2 ba · 1,467 sqft

    2275 Island Run, Winter Park, FL

    Yukey Hoo · U KEY REALTY

  • 2349 Shadowland Loop — photo36Active

    $425,000

    3 bd · 3 ba · 1,755 sqft

    2349 Shadowland Loop, Winter Park, FL

    Lindsey Hudson · REAL BROKER, LLC

  • 7506 Cranes Creek Ct #30 — photo20Active

    $365,000

    3 bd · 3 ba · 1,861 sqft

    7506 Cranes Creek Ct #30, Winter Park, FL

    Sylvia Marchese · TRANSCONTINENTAL REALTY GROUP,

  • 7530 Cranes Creek Ct — photo24Active

    $309,900

    3 bd · 3 ba · 1,545 sqft

    7530 Cranes Creek Ct, Winter Park, FL

    Edward Hru · ROO REALTY LLC

  • 1259 Indiana Ave — photo67Active

    $575,000

    2 bd · 3 ba · 1,648 sqft

    1259 Indiana Ave, Winter Park, FL

    Karan Wienker · COLDWELL BANKER REALTY

  • 7605 Aloma Pines Ct — photoPrice Reduced28Active

    $349,000

    3 bd · 3 ba · 1,872 sqft

    7605 Aloma Pines Ct, Winter Park, FL

    Simon Colak · USCO CAPITAL GROUP

  • 2857 Clever Ln — photoPrice Reduced26Active

    $399,995

    3 bd · 3 ba · 1,782 sqft

    2857 Clever Ln, Winter Park, FL

    Justin Dalrymple, LLC · MAINFRAME REAL ESTATE

  • 1256 Melissa Ct — photo21Active

    $660,000

    3 bd · 3 ba · 1,690 sqft

    1256 Melissa Ct, Winter Park, FL

    Wesley Morales · KELLER WILLIAMS REALTY AT THE PARKS

  • 1071 Aragon Ave — photo34Active

    $575,000

    2 bd · 3 ba · 1,851 sqft

    1071 Aragon Ave, Winter Park, FL

    Greg Vazzana · FANNIE HILLMAN & ASSOCIATES

  • 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

  • 1927 S Lakemont Ave — photoPrice ReducedOpen house Sun, Oct 11 · 11:00 AM48Active

    $915,000

    3 bd · 4 ba · 2,093 sqft

    1927 S Lakemont Ave, Winter Park, FL

    Abby Green · IAD REAL ESTATE

  • 125 S Interlachen Ave #1 — photoPrice Reduced76Active

    $3,695,000

    3 bd · 5 ba · 3,878 sqft

    125 S Interlachen Ave #1, Winter Park, FL

    Skip Kirst · COLLADO REAL ESTATE

  • 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

  • 2487 Harbour Way — photoPrice Reduced13Active

    $270,000

    3 bd · 3 ba · 1,803 sqft

    2487 Harbour Way, Winter Park, FL

    Joel Garay · LOKATION

  • 1138 S Pennsylvania Ave — photoPrice Reduced41Active

    $925,000

    3 bd · 3 ba · 2,434 sqft

    1138 S Pennsylvania Ave, Winter Park, FL

    George Stringer · COLDWELL BANKER REALTY

  • 660 W Morse Blvd — photoPrice Reduced70Active

    $2,695,000

    3 bd · 4 ba · 3,286 sqft

    660 W Morse Blvd, Winter Park, FL

    Jennifer Sloan · COMPASS FLORIDA LLC

  • 512 W Swoope Ave — photo46Active

    $1,399,000

    3 bd · 3 ba · 2,585 sqft

    512 W Swoope Ave, Winter Park, FL

    Carmen Quintana · COLDWELL BANKER REALTY

  • 12

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    • New Construction Homes
    • Homes with a Pool
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    Listing data & MLS disclosures

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    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.