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3 bedsNew constructionWith a pool
Homes Under $2M in Winter Park, FL — Page 9
294 listings

Homes Under $2M in Winter Park, FL

Homes Under $2M in Winter Park, FL

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22 of 294 Listings
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Homes Under $2M in Winter Park, FL

22 of 294 Listings

  1. 3006 Northwood Blvd — photoPrice Reduced46

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas
Active

$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

  • 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

  • 2712 Tortoise CV — photoPrice Reduced22Active

    $230,000

    2 bd · 1 ba · 924 sqft

    2712 Tortoise CV, Winter Park, FL

    Lisa Wright · CHARLES RUTENBERG REALTY ORLANDO

  • 512 W Swoope Ave — photo46Active

    $1,399,000

    3 bd · 3 ba · 2,585 sqft

    512 W Swoope Ave, Winter Park, FL

    Carmen Quintana · COLDWELL BANKER REALTY

  • 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

  • 151 North Orlando Avenue #142 — photo30Active

    $199,900

    1 bd · 1 ba · 582 sqft

    151 North Orlando Avenue #142, Winter Park, FL

    Chris Creegan · CREEGAN GROUP

  • 2015 Summerfield Rd — photoPrice ReducedOpen house Sat, Oct 10 · 12:00 PM31Active

    $1,250,000

    4 bd · 4 ba · 3,024 sqft

    2015 Summerfield Rd, Winter Park, FL

    Courtney Lindsay · UNITED REAL ESTATE PREFERRED

  • 101 S New York Ave #311 — photoPrice Reduced39Active

    $1,775,000

    3 bd · 4 ba · 3,112 sqft

    101 S New York Ave #311, Winter Park, FL

    Tiffany Grindstaff · KELLY PRICE & COMPANY LLC

  • 1605 Puritan Ave — photoPrice Reduced19Active

    $379,000

    3 bd · 2 ba · 1,285 sqft

    1605 Puritan Ave, Winter Park, FL

    Angelica Tomlinson LLC · CENTURY 21 CARIOTI

  • 437 N Capen Ave — photo36Active

    $849,000

    3 bd · 3 ba · 1,904 sqft

    437 N Capen Ave, Winter Park, FL

    Brandon Geers · COMPASS FLORIDA LLC

  • 2008 Houndslake Drive — photoPrice Reduced35Active

    $470,000

    4 bd · 2 ba · 2,250 sqft

    2008 Houndslake Drive, Winter Park, FL

    Kevin McCulty · Mark Spain Real Estate

  • 1840 Aster Dr — photoPrice Reduced20Active

    $379,900

    3 bd · 2 ba · 1,667 sqft

    1840 Aster Dr, Winter Park, FL

    Brendon Spalding · KONA REALTY SERVICES LLC

  • 1316 Blue Stem Ln — photo42Active

    $725,000

    4 bd · 3 ba · 2,196 sqft

    1316 Blue Stem Ln, Winter Park, FL

    Matthew Fong · AFFINITY REALTY LLC

  • 8433 Commander CV — photoPrice Reduced59Active

    $455,000

    4 bd · 3 ba · 1,903 sqft

    8433 Commander CV, Winter Park, FL

    Brandi Cepeda · CEPEDA REAL ESTATE LLC

  • 1265 Arlington Pl — photoPrice Reduced38Active

    $774,900

    3 bd · 4 ba · 2,030 sqft

    1265 Arlington Pl, Winter Park, FL

    Erika Beerbower · FANNIE HILLMAN & ASSOCIATES

  • 1535 Lawndale Cir — photoPrice Reduced15Active

    $420,000

    3 bd · 2 ba · 1,676 sqft

    1535 Lawndale Cir, Winter Park, FL

    Raul Pino · SOVEREIGN REAL ESTATE GROUP

  • 1473 Berkshire Ave — photoPrice Reduced38Active

    $1,369,000

    5 bd · 4 ba · 2,446 sqft

    1473 Berkshire Ave, Winter Park, FL

    Gilson Rodrigues · KARDOSH REALTY

  • 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

  • 2715 Prince John Rd — photoPrice Reduced29Active

    $494,900

    3 bd · 2 ba · 1,565 sqft

    2715 Prince John Rd, Winter Park, FL

    Donna Peebles · VIA PROPERTIES LLC

  • 1…8910…13

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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #BK3453168

    Call Thomas

    Listing data & MLS disclosures

    Space Coast MLS (Space Coast Association of REALTORS)
    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 Space Coast MLS, Inc®. All Rights Reserved. Last Updated: 2026-10-08 20:27:03 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 · 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.