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3 bedsNew constructionWith a pool
4 Bedroom Homes in Winter Park, FL
102 listings

4 Bedroom Homes in Winter Park, FL

4 Bedroom Homes in Winter Park, FL

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24 of 102 Listings
Map

4 Bedroom Homes in Winter Park, FL

24 of 102 Listings

  1. 1458 Lone Feather Trl — photo39Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

$650,000

4 bd · 3 ba · 1,770 sqft

1458 Lone Feather Trl, Winter Park, FL

Harif Hazera LLC · PREMIER SOTHEBY'S INTL. REALTY

  • Active

    $450,000

    4 bd · 3 ba · 1,866 sqft

    239 Orange Terrace Dr, Winter Park, FL

    Chris Creegan · CREEGAN GROUP

  • 1939 Woodcrest Dr — photo58Active

    $1,349,000

    4 bd · 4 ba · 2,575 sqft

    1939 Woodcrest Dr, Winter Park, FL

    Jose Martinez Rivera LLC · LA ROSA REALTY PREMIER LLC

  • 2174 Shadyhill Ter — photo41Active

    $529,900

    4 bd · 2 ba · 1,983 sqft

    2174 Shadyhill Ter, Winter Park, FL

    Ahmad Karain · SET HOMES REALTY LLC

  • 1611 Chestnut Ave — photo55Active

    $985,000

    4 bd · 4 ba · 2,916 sqft

    1611 Chestnut Ave, Winter Park, FL

    Gunel Aydamirli · OLYMPUS EXECUTIVE REALTY INC

  • 2234 Howard Dr — photo17Active

    $2,295,000

    4 bd · 6 ba · 3,295 sqft

    2234 Howard Dr, Winter Park, FL

    Raquel Elliott · COLDWELL BANKER REALTY

  • 1737 Indiana Ave — photo38Active

    $1,399,900

    4 bd · 4 ba · 2,984 sqft

    1737 Indiana Ave, Winter Park, FL

    Tori Nguyen · LOKATION

  • 731 Bongart Rd — photo51Active

    $519,900

    4 bd · 3 ba · 1,842 sqft

    731 Bongart Rd, Winter Park, FL

    Steven Koleno · BEYCOME OF FLORIDA LLC

  • 2228 King Charles Ct — photoOpen house Sat, Oct 24 · 11:00 AM35Active

    $575,000

    4 bd · 3 ba · 2,551 sqft

    2228 King Charles Ct, Winter Park, FL

    Heather Pryor · KELLER WILLIAMS ADVANTAGE REALTY

  • 3416 Arbutus Ln — photoPrice Reduced20Active

    $379,900

    4 bd · 3 ba · 1,421 sqft

    3416 Arbutus Ln, Winter Park, FL

    Jorge Schlaefli · GPS REALTY GROUP

  • 2067 Poinciana Rd — photoOpen house Sat, Oct 24 · 11:00 AM90Active

    $560,000

    4 bd · 2 ba · 2,352 sqft

    2067 Poinciana Rd, Winter Park, FL

    Brandon Williams · WATSON REALTY CORP

  • 2020 Leanne Ct — photo28Active

    $479,900

    4 bd · 3 ba · 2,088 sqft

    2020 Leanne Ct, Winter Park, FL

    Ileana Perez · HOUWZER INC

  • 2613 Lafayette Ave — photo12Active

    $1,699,900

    4 bd · 4 ba · 2,661 sqft

    2613 Lafayette Ave, Winter Park, FL

    Matt Tomaszewski · CORCORAN PREMIER REALTY

  • 2322 Woodcrest Dr — photo28Active

    $675,000

    4 bd · 2 ba · 1,650 sqft

    2322 Woodcrest Dr, Winter Park, FL

    Jill Healey · KELLER WILLIAMS WINTER PARK

  • 2052 Wood Thrush Ln — photo54Active

    $900,000

    4 bd · 3 ba · 2,807 sqft

    2052 Wood Thrush Ln, Winter Park, FL

    Ron Verzaro, II · KELLER WILLIAMS ADVANTAGE REALTY

  • 2007 Edwin Blvd — photo4Active

    $1,995,000

    4 bd · 4 ba · 3,314 sqft

    2007 Edwin Blvd, Winter Park, FL

    Angela Rodriguez · DREAM FINDERS REALTY GROUP CORP

  • 266 N Ranger Blvd — photo33Active

    $724,900

    4 bd · 3 ba · 1,692 sqft

    266 N Ranger Blvd, Winter Park, FL

    Moises Rivera · ELITE PROPERTY REAL ESTATE LLC

  • 7786 Fox Knoll Pl — photoPrice Reduced55Active

    $398,000

    4 bd · 2 ba · 1,301 sqft

    7786 Fox Knoll Pl, Winter Park, FL

    Eric Senate · NIZZ REALTY INC

  • 555 E Lake Sue Ave — photo96Active

    $2,095,000

    4 bd · 4 ba · 3,776 sqft

    555 E Lake Sue Ave, Winter Park, FL

    Claudia Davidson · KELLER WILLIAMS WINTER PARK

  • 2614 Parkland Dr — photo54Active

    $1,890,000

    4 bd · 4 ba · 3,307 sqft

    2614 Parkland Dr, Winter Park, FL

    Ryan Gaston · JW GASTON LLC

  • 3209 Heartwood Ave — photoPrice Reduced12Active

    $439,900

    4 bd · 2 ba · 1,627 sqft

    3209 Heartwood Ave, Winter Park, FL

    James Fitzgibbon · LEDGE REAL ESTATE SOLUTIONS LLC

  • 1951 Winter Park Rd — photo73Active

    $2,089,000

    4 bd · 4 ba · 3,479 sqft

    1951 Winter Park Rd, Winter Park, FL

    Holly Wilton · KELLER WILLIAMS WINTER PARK

  • 533 Country Club Dr — photo31Active

    $1,599,000

    4 bd · 4 ba · 2,942 sqft

    533 Country Club Dr, Winter Park, FL

    Jill Healey · KELLER WILLIAMS WINTER PARK

  • 4260 Bear Gully Rd — photo52Active

    $599,000

    4 bd · 4 ba · 2,322 sqft

    4260 Bear Gully Rd, Winter Park, FL

    Alexandre Zapparoli LLC · WRA BUSINESS & REAL ESTATE

  • 12…5

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    • Homes Under $1M
    • Homes Under $1.25M
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    • Luxury Homes

    By bedrooms

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    • New Construction Homes
    • Homes with a Pool
    • Open Houses
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    Thomas O'Leary

    Realty.com

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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 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.