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3 bedsNew constructionWith a pool
2 Bedroom Homes in Winter Park, FL
58 listings

2 Bedroom Homes in Winter Park, FL

2 Bedroom Homes in Winter Park, FL

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23 of 58 Listings
Map

2 Bedroom Homes in Winter Park, FL

23 of 58 Listings

  1. 1411 Devon Rd — photo47Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

$950,000

2 bd · 2 ba · 1,947 sqft

1411 Devon Rd, Winter Park, FL

Harif Hazera LLC · PREMIER SOTHEBY'S INTL. REALTY

  • 4882 Tangerine Ave #4882 — photo28Active

    $185,000

    2 bd · 2 ba · 1,281 sqft

    4882 Tangerine Ave #4882, Winter Park, FL

    Greg Sibley · SIMPLYSOLD REAL ESTATE PREMIER

  • 700 Melrose Ave #M23 — photo29Active

    $354,000

    2 bd · 2 ba · 1,074 sqft

    700 Melrose Ave #M23, Winter Park, FL

    Linda Jokbengboon · COMPASS FLORIDA LLC

  • 1500 Gay Rd #26-C — photo25Active

    $255,000

    2 bd · 2 ba · 1,026 sqft

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

    Lianna Dangelo · SOTERA LIVING

  • 1602 Alabama Dr #107 — photo33Active

    $1,150,000

    2 bd · 2 ba · 993 sqft

    1602 Alabama Dr #107, Winter Park, FL

    Valerie Leary · CORCORAN PREMIER REALTY

  • 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

  • 188 Sandlewood #1 — photo25Active

    $290,000

    2 bd · 3 ba · 1,133 sqft

    188 Sandlewood #1, Winter Park, FL

    Tom Noelke · NOELKE REALTY

  • 1695 Lee Rd #C206 — photo24Active

    $140,000

    2 bd · 1 ba · 881 sqft

    1695 Lee Rd #C206, Winter Park, FL

    Ingrid Garcia Rodriguez · INVESTMENT REALTY

  • 1250 S Denning Dr #119 — photo31Active

    $265,000

    2 bd · 2 ba · 908 sqft

    1250 S Denning Dr #119, Winter Park, FL

    Justin McCarthy · FANNIE HILLMAN & ASSOCIATES

  • 192 Balfour Dr #2 — photo52Active

    $319,000

    2 bd · 2 ba · 1,287 sqft

    192 Balfour Dr #2, Winter Park, FL

    Tricia Ramsby · BHHS FLORIDA REALTY

  • 7453 Daniel Webster Dr #a5 — photo20Active

    $150,000

    2 bd · 2 ba · 1,063 sqft

    7453 Daniel Webster Dr #a5, Winter Park, FL

    Laila Dkhissi · LA ROSA REALTY PREMIER LLC

  • 1306 S Pennsylvania Ave #5 — photoPrice Reduced33Active

    $349,000

    2 bd · 1 ba · 830 sqft

    1306 S Pennsylvania Ave #5, Winter Park, FL

    Lisa Gould · KELLER WILLIAMS WINTER PARK

  • 2383 Sun Valley Cir #2383 — photo33Active

    $234,900

    2 bd · 2 ba · 1,295 sqft

    2383 Sun Valley Cir #2383, Winter Park, FL

    Carmen Aridas · RE/MAX PRIME PROPERTIES

  • 7476 Woodburn Ct #38 — photo28Active

    $170,000

    2 bd · 3 ba · 1,031 sqft

    7476 Woodburn Ct #38, Winter Park, FL

    Habib Fahs · COLDWELL BANKER REALTY

  • 2302 Barbados Dr — photoPrice Reduced35Active

    $275,000

    2 bd · 2 ba · 1,544 sqft

    2302 Barbados Dr, Winter Park, FL

    George Freelove · KELLER WILLIAMS REALTY AT THE PARKS

  • 3651 N Goldenrod Rd #C109 — photo18Active

    $165,000

    2 bd · 2 ba · 840 sqft

    3651 N Goldenrod Rd #C109, Winter Park, FL

    Valerie Wanzer · REAL ESTATE PROFESSIONALS SE

  • 1250 S Denning Dr #127 — photo28Active

    $245,000

    2 bd · 2 ba · 908 sqft

    1250 S Denning Dr #127, Winter Park, FL

    Drew Henner · PREMIER SOTHEBY'S INTL. REALTY

  • 5108 Lazy Oaks Dr #5108 — photoPrice Reduced30Active

    $255,000

    2 bd · 2 ba · 1,008 sqft

    5108 Lazy Oaks Dr #5108, Winter Park, FL

    Steven Koleno · BEYCOME OF FLORIDA 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

  • 151 N Orlando Ave #242 — photo25Active

    $269,000

    2 bd · 1 ba · 710 sqft

    151 N Orlando Ave #242, Winter Park, FL

    Alexander Scures · COLONIALTOWN REALTY

  • 4027 Northlight Dr Unit 4 — photo31Active

    $259,900

    2 bd · 2 ba · 1,234 sqft

    4027 Northlight Dr Unit 4, Winter Park, FL

    Kathleen Leavesley · Coffey Real Estate Agency LLC

  • 1250 S Denning Dr Unit 233 — photoPrice Reduced31Active

    $242,500

    2 bd · 2 ba · 913 sqft

    1250 S Denning Dr Unit 233, Winter Park, FL

    Samuel Kingsford · STOCKWORTH REALTY GROUP

  • 222 Lewfield Cir — photo47Active

    $189,900

    2 bd · 2 ba · 953 sqft

    222 Lewfield Cir, Winter Park, FL

    Joshua Neudigate · MARKET CONNECT REALTY LLC

  • 123

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    Listing data & MLS disclosures

    Florida Gulf Coast MLS/Royal Palm Coast Realtor Association(SWFLMLS)
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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

    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 30, 2026

    Median sale price
    $566,750$404,625–$1,046,250 typical range
    Price per sq. ft.
    $342
    Sales
    108
    Paid in cash
    43.5%

    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
    27.8%

    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.