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3 bedsNew constructionWith a pool
Homes Under $2M in Winter Park, FL — Page 8
292 listings

Homes Under $2M in Winter Park, FL

Homes Under $2M in Winter Park, FL

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24 of 292 Listings
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Homes Under $2M in Winter Park, FL

24 of 292 Listings

  1. 1500 Gay Rd #4D — photoPrice Reduced15

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas
Active

$159,900

1 bd · 1 ba · 732 sqft

1500 Gay Rd #4D, Winter Park, FL

Janice Erickson · REALCOM REAL ESTATE SERVICES INC

  • 1133 Bella Lago CV — photoPrice Reduced21Active

    $1,999,900

    3 bd · 2 ba · 1,765 sqft

    1133 Bella Lago CV, Winter Park, FL

    Hang Kendall · LPT REALTY, LLC

  • 2487 Harbour Way — photoPrice Reduced13Active

    $270,000

    3 bd · 3 ba · 1,803 sqft

    2487 Harbour Way, Winter Park, FL

    Joel Garay · LOKATION

  • 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

  • 922 N Pennsylvania Ave — photoPrice Reduced30Active

    $1,875,000

    4 bd · 4 ba · 3,440 sqft

    922 N Pennsylvania Ave, Winter Park, FL

    Mick Night · PREMIER SOTHEBY'S INTL. REALTY

  • 1418 Lone Feather Trl — photoPrice Reduced46Active

    $699,500

    4 bd · 3 ba · 2,197 sqft

    1418 Lone Feather Trl, Winter Park, FL

    Harif Hazera LLC · PREMIER SOTHEBY'S INTL. REALTY

  • 250 Killarney — photo10Active

    $1,600,000

    4 bd · 4 ba · 2,568 sqft

    250 Killarney, Winter Park, FL

    Nancy Rossman · FLORIDA PROPERTY SPECIALIST

  • 1401 Aster Ct — photoPrice Reduced26Active

    $399,999

    4 bd · 2 ba · 1,653 sqft

    1401 Aster Ct, Winter Park, FL

    Brian Dodd · SPARROW REALTY & RENTALS

  • 462 W Lyman Ave — photoPrice Reduced28Active

    $1,495,000

    3 bd · 3 ba · 1,944 sqft

    462 W Lyman Ave, Winter Park, FL

    Mick Night · PREMIER SOTHEBY'S INTL. REALTY

  • 885 Carnation Dr — photoPrice Reduced38Active

    $368,000

    4 bd · 2 ba · 1,240 sqft

    885 Carnation Dr, Winter Park, FL

    Tashania Brown · RADIUS REALTY GROUP LLC

  • 2450 Grand Teton Cir #2450 — photoPrice Reduced37Active

    $250,000

    3 bd · 2 ba · 1,311 sqft

    2450 Grand Teton Cir #2450, Winter Park, FL

    John Campese · CHARLES RUTENBERG REALTY ORLANDO

  • 2041 Jewell Ave — photoPrice Reduced30Active

    $439,900

    3 bd · 1 ba · 1,508 sqft

    2041 Jewell Ave, Winter Park, FL

    Martha Coronel · IAD REAL ESTATE

  • 1003 Lake Bell Dr — photoPrice Reduced30Active

    $549,900

    3 bd · 2 ba · 1,837 sqft

    1003 Lake Bell Dr, Winter Park, FL

    Bryan Douglas · KELLER WILLIAMS REALTY AT THE PARKS

  • 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

  • 1000 S Semoran Blvd #408 — photoPrice Reduced11Active

    $138,000

    1 bd · 1 ba · 776 sqft

    1000 S Semoran Blvd #408, Winter Park, FL

    Scott Butts · KIMBRIDGE REALTY, LLC

  • 1000 S Semoran Blvd #306 — photoPrice Reduced13Active

    $138,000

    1 bd · 1 ba · 796 sqft

    1000 S Semoran Blvd #306, Winter Park, FL

    Scott Butts · KIMBRIDGE REALTY, LLC

  • 1000 S Semoran Blvd #404 — photoPrice Reduced5Active

    $138,000

    1 bd · 1 ba · 776 sqft

    1000 S Semoran Blvd #404, Winter Park, FL

    Scott Butts · KIMBRIDGE REALTY, LLC

  • 1138 S Pennsylvania Ave — photoPrice Reduced41Active

    $925,000

    3 bd · 3 ba · 2,434 sqft

    1138 S Pennsylvania Ave, Winter Park, FL

    George Stringer · COLDWELL BANKER REALTY

  • 981 Aragon Ave — photoPrice Reduced31Active

    $494,999

    2 bd · 1 ba · 857 sqft

    981 Aragon Ave, Winter Park, FL

    Thomas Bonner · COLDWELL BANKER REALTY

  • 3006 Northwood Blvd — photoPrice Reduced46Active

    $925,000

    4 bd · 3 ba · 2,075 sqft

    3006 Northwood Blvd, Winter Park, FL

    Daren Ellington · ORLANDO HOMES GROUP LLC

  • 259 Orange Terrace Drive — photoPrice Reduced26Active

    $439,000

    3 bd · 2 ba · 1,248 sqft

    259 Orange Terrace Drive, Winter Park, FL

    Jo Ann Lamar · PREMIER SOTHEBY'S INTL. REALTY

  • 1564 Lawndale Cir — photo45Active

    $450,000

    4 bd · 3 ba · 1,980 sqft

    1564 Lawndale Cir, Winter Park, FL

    Yahya Chhotani LLC · SET HOMES REALTY LLC

  • 1…789…13

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    Realty.com

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    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 · This period is still settling

    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 23, 2026

    Median sale price
    $602,500$441,750–$1,016,350 typical range
    Price per sq. ft.
    $358
    Sales
    78
    Paid in cash
    46.2%

    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
    38.1%

    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.