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

2 Bedroom Homes in Winter Park, FL

2 Bedroom Homes in Winter Park, FL

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23 of 58 Listings
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2 Bedroom Homes in Winter Park, FL

23 of 58 Listings

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TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas
  1. 1411 Devon Rd — photo47Active

    $950,000

    2 bd · 2 ba · 1,947 sqft

    1411 Devon Rd, Winter Park, FL

    Harif Hazera LLC · PREMIER SOTHEBY'S INTL. REALTY

  2. 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

  3. 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

  4. 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

  5. 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

  6. 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

  7. 188 Sandlewood #1 — photo25Active

    $290,000

    2 bd · 3 ba · 1,133 sqft

    188 Sandlewood #1, Winter Park, FL

    Tom Noelke · NOELKE REALTY

  8. 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

  9. 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

  10. 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

  11. 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

  12. 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

  13. 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

  14. 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

  15. 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

  16. 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

  17. 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

  18. 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

  19. 1259 Indiana Ave — photo67Active

    $575,000

    2 bd · 3 ba · 1,648 sqft

    1259 Indiana Ave, Winter Park, FL

    Karan Wienker · COLDWELL BANKER REALTY

  20. 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

  21. 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

  22. 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

  23. 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

About 2 Bedroom Homes in Winter Park, FL

2 Bedroom Homes in Winter Park, FL: 58 active listings as of October 19, 2026, 18:25 UTC.

Property types among these 58 listings, by the property type each listing’s MLS reports, spelled as the MLS spells it. Types with fewer than 5 listings, and listings whose MLS reports no type, are not shown, so the shares can total less than 100%.
Property typeListingsShare
Condominium4679.3%
Single Family Residence610.3%

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The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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Listing data & MLS disclosures

Florida Gulf Coast MLS/Royal Palm Coast Realtor Association(SWFLMLS)
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.
Listing information ©2026 Florida Gulf Coast MLS®, Inc®. All Rights Reserved. Last Updated: 2026-10-09 17:26:53 UTC
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.
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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #BK3453168

    Call Thomas

    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.