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3 bedsNew constructionWith a pool
Homes Under $800K in Winter Park, FL — Page 2
204 listings

Homes Under $800K in Winter Park, FL

Homes Under $800K in Winter Park, FL

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24 of 204 Listings
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Homes Under $800K in Winter Park, FL

24 of 204 Listings

  1. 2887 Temple Trl — photo86Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

$695,000

2 bd · 3 ba · 1,801 sqft

2887 Temple Trl, Winter Park, FL

Michael Rains, PA · ADAIR REALTY INC

  • 7641 Village Green Drive — photoPrice Reduced33Active

    $515,000

    3 bd · 3 ba · 1,602 sqft

    7641 Village Green Drive, Winter Park, FL

    Jannett Jhasmin Marten · Compass Florida, LLC

  • 5468 Bracken Ct — photoPrice Reduced24Active

    $299,000

    3 bd · 3 ba · 1,602 sqft

    5468 Bracken Ct, Winter Park, FL

    James Hogan · EXP REALTY LLC

  • 2913 Clever Lane — photo37Active

    $425,000

    3 bd · 3 ba · 1,907 sqft

    2913 Clever Lane, Winter Park, FL

    HELEN WELLS · MAXREV, LLC

  • 2640 Beverly Ave — photo29Active

    $305,000

    3 bd · 1 ba · 1,216 sqft

    2640 Beverly Ave, Winter Park, FL

    Celeste Martinez · REAL BROKER, LLC

  • 1740 Puritan Ave — photoPrice Reduced16Active

    $314,000

    3 bd · 2 ba · 1,229 sqft

    1740 Puritan Ave, Winter Park, FL

    Brenda Brooks · KELLER WILLIAMS REALTY SMART 1

  • 8061 Pleasant Pine Cir — photo43Active

    $750,000

    5 bd · 4 ba · 3,496 sqft

    8061 Pleasant Pine Cir, Winter Park, FL

    Mark Humphreys · RE/MAX ASSURED

  • 216 Lewfield Cir #216 — photo25Active

    $230,000

    3 bd · 2 ba · 1,268 sqft

    216 Lewfield Cir #216, Winter Park, FL

    Vicki Bray-Fagan, LLC · WATSON REALTY CORP

  • 2219 Winter Woods Blvd — photo23Active

    $479,999

    3 bd · 3 ba · 1,776 sqft

    2219 Winter Woods Blvd, Winter Park, FL

    Bryan Rhoads · LKV REALTY, LLC

  • 1399 Aloma Ave — photo30Active

    $575,000

    3 bd · 2 ba · 1,804 sqft

    1399 Aloma Ave, Winter Park, FL

    Nancy Bagby · FANNIE HILLMAN & ASSOCIATES

  • 1407 Broad Wing Ln — photoPrice Reduced41Active

    $482,000

    3 bd · 3 ba · 2,308 sqft

    1407 Broad Wing Ln, Winter Park, FL

    Roger Michaels · R MICHAELS REALTY LLC

  • 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

  • 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

  • 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

  • 2228 King Charles Ct — photo36Active

    $575,000

    4 bd · 3 ba · 2,551 sqft

    2228 King Charles Ct, Winter Park, FL

    Heather Pryor · KELLER WILLIAMS ADVANTAGE REALTY

  • 2067 Poinciana Rd — photoPrice Reduced90Active

    $548,000

    4 bd · 2 ba · 2,352 sqft

    2067 Poinciana Rd, Winter Park, FL

    Brandon Williams · WATSON REALTY CORP

  • 2020 Leanne Ct — photoPrice Reduced28Active

    $469,900

    4 bd · 3 ba · 2,088 sqft

    2020 Leanne Ct, Winter Park, FL

    Ileana Perez · HOUWZER INC

  • 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

  • 518 Gilbert Rd — photo48Active

    $649,000

    3 bd · 2 ba · 1,573 sqft

    518 Gilbert Rd, Winter Park, FL

    Monika Kenney · PALMANO GROUP RE BROKERAGE LLC

  • 112 Bell Pl — photo31Active

    $575,000

    3 bd · 2 ba · 2,253 sqft

    112 Bell Pl, Winter Park, FL

    Cara Edwards · ALL REAL ESTATE & INVESTMENTS

  • 3032 Antique Oaks Cir #145 — photoPrice Reduced15Active

    $134,999

    1 bd · 1 ba · 749 sqft

    3032 Antique Oaks Cir #145, Winter Park, FL

    Parker Blanchard · OLDE TOWN BROKERS INC

  • 310 Granada Dr — photoPrice Reduced27Active

    $325,000

    3 bd · 2 ba · 1,344 sqft

    310 Granada Dr, Winter Park, FL

    Milton James · COLDWELL BANKER REALTY

  • 2322 Woodcrest Dr — photoPrice Reduced28Active

    $650,000

    4 bd · 2 ba · 1,650 sqft

    2322 Woodcrest Dr, Winter Park, FL

    Jill Healey · KELLER WILLIAMS WINTER PARK

  • 123…9

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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #BK3453168

    Call Thomas

    Listing data & MLS disclosures

    MiamiSouthFlorida
    Listing information provided by MiamiSouthFlorida.
    realMLS (Northeast Florida Multiple Listing Service)
    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. Data is deemed reliable but is not guaranteed accurate by NEFMLS.
    Listing information ©2026 Northeast Florida Association of Realtors, Inc®. All Rights Reserved. Last Updated: 2026-10-29 18:48:05 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.

    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.