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3 bedsNew constructionWith a pool
2 Bedroom Homes in Winter Park, FL — Page 2
49 listings

2 Bedroom Homes in Winter Park, FL

2 Bedroom Homes in Winter Park, FL

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24 of 49 Listings
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2 Bedroom Homes in Winter Park, FL

24 of 49 Listings

  1. 2477 Tahoe Cir #2477 — photoPrice Reduced24

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas
Active

$247,000

2 bd · 2 ba · 1,316 sqft

2477 Tahoe Cir #2477, Winter Park, FL

Kyle Clark · RE/MAX TOWN & COUNTRY REALTY

  • 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

  • 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

  • 7450 Wynnewood Sq #189 — photoPrice Reduced45Active

    $170,000

    2 bd · 3 ba · 1,031 sqft

    7450 Wynnewood Sq #189, Winter Park, FL

    Kim King · REAL ESTATE PROFESSIONALS SE

  • 5184 Lazy Oaks Dr — photoPrice Reduced31Active

    $275,000

    2 bd · 2 ba · 1,008 sqft

    5184 Lazy Oaks Dr, Winter Park, FL

    Joyce Gary · PAINE-ANDERSON PROPERTIES, INC

  • 2305 Sun Valley Cir — photo42Active

    $279,900

    2 bd · 2 ba · 1,295 sqft

    2305 Sun Valley Cir, Winter Park, FL

    Ryan Barnett · MARKET CONNECT REALTY LLC

  • 2372 Sun Valley Cir #2372 — photo42Active

    $285,000

    2 bd · 2 ba · 1,495 sqft

    2372 Sun Valley Cir #2372, Winter Park, FL

    Sheila Mathews · COLDWELL BANKER REALTY

  • 7488 Whisperwood Dr #28 — photoPrice Reduced36Active

    $199,000

    2 bd · 3 ba · 1,578 sqft

    7488 Whisperwood Dr #28, Winter Park, FL

    Miranda Azer · PARKVIEW REAL ESTATE

  • 1500 Gay Rd #3C — photoPrice Reduced26Active

    $235,000

    2 bd · 2 ba · 1,026 sqft

    1500 Gay Rd #3C, Winter Park, FL

    Heather Frazee · FANNIE HILLMAN & ASSOCIATES

  • 2500 Lee Rd #220 — photo28Active

    $199,900

    2 bd · 1 ba · 851 sqft

    2500 Lee Rd #220, Winter Park, FL

    Thomas Nickley, Jr · KELLER WILLIAMS REALTY AT THE PARKS

  • 2500 Lee Rd #104 — photoPrice Reduced23Active

    $242,400

    2 bd · 2 ba · 956 sqft

    2500 Lee Rd #104, Winter Park, FL

    Stephen Hachey · FLAT FEE MLS REALTY

  • 193 Lewfield Cir — photo41Active

    $248,900

    2 bd · 3 ba · 1,300 sqft

    193 Lewfield Cir, Winter Park, FL

    Efrain Reyes · COLDWELL BANKER REALTY

  • 2923 Antique Oaks Cir #34 — photoPrice Reduced22Active

    $180,000

    2 bd · 2 ba · 1,105 sqft

    2923 Antique Oaks Cir #34, Winter Park, FL

    Steve Pugh · EXP REALTY LLC

  • 3243 Forest Oaks Court #117 — photoPrice Reduced20Active

    $172,000

    2 bd · 2 ba · 990 sqft

    3243 Forest Oaks Court #117, Winter Park, FL

    Jessie Lin, LLC · SOGO REAL ESTATE SERVICES LLC

  • 7327 Forest Hill Ct #223 — photoPrice Reduced24Active

    $175,000

    2 bd · 3 ba · 1,031 sqft

    7327 Forest Hill Ct #223, Winter Park, FL

    Leda Vaz · M L VAZ REALTY INC

  • 5143 Lazy Oaks Dr #5143 — photoPrice Reduced41Active

    $275,000

    2 bd · 2 ba · 1,008 sqft

    5143 Lazy Oaks Dr #5143, Winter Park, FL

    Mindy Machock · KELLER WILLIAMS REALTY AT THE PARKS

  • 3021 Aaron Burr Ave #3 — photo21Active

    $140,000

    2 bd · 3 ba · 1,090 sqft

    3021 Aaron Burr Ave #3, Winter Park, FL

    Daiana Garcia Medrano · NAIM REAL ESTATE LLC

  • 7300 Daniel Webster Dr #M7 — photoPrice Reduced34Active

    $159,000

    2 bd · 3 ba · 1,108 sqft

    7300 Daniel Webster Dr #M7, Winter Park, FL

    Rosa Rodriguez · STIRLING INTERNATIONAL REAL ES

  • 3027 Aaron Burr Ave #L1 — photoPrice Reduced35Active

    $159,000

    2 bd · 3 ba · 1,090 sqft

    3027 Aaron Burr Ave #L1, Winter Park, FL

    Rosa Rodriguez · STIRLING INTERNATIONAL REAL ES

  • 630 Killarney Bay Ct #3 — photoPrice Reduced55Active

    $459,900

    2 bd · 3 ba · 1,428 sqft

    630 Killarney Bay Ct #3, Winter Park, FL

    Anthony Consalvo · FLORIDA ONE REAL ESTATE LLC

  • 151 N Orlando Ave #118 — photo20Active

    $299,999

    2 bd · 1 ba · 710 sqft

    151 N Orlando Ave #118, Winter Park, FL

    Adriana Montes · FLORIDA DREAMS REALTY GRP INC

  • 205 Lewfield Cir #205 — photoPrice Reduced37Active

    $182,900

    2 bd · 2 ba · 927 sqft

    205 Lewfield Cir #205, Winter Park, FL

    Eimi Moreno Carrera · LPT REALTY, LLC

  • 151 N Orlando Ave ##115 — photoPrice Reduced23Active

    $285,000

    2 bd · 1 ba · 710 sqft

    151 N Orlando Ave ##115, Winter Park, FL

    Chris Creegan · CREEGAN GROUP

  • 2336 Sun Valley Cir #Bldg 20 — photoPrice Reduced12Active

    $285,000

    2 bd · 2 ba · 1,669 sqft

    2336 Sun Valley Cir #Bldg 20, Winter Park, FL

    Lizzie Beaudoin · PR REAL ESTATE SERVICES

  • 123

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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

    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 28, 2026

    Median sale price
    $565,000$410,000–$952,600 typical range
    Price per sq. ft.
    $342
    Sales
    92
    Paid in cash
    44.6%

    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
    28.1%

    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.