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3 bedsNew constructionWith a pool
Homes Under $300K in Middletown, NY
47 listings

Homes Under $300K in Middletown, NY

Homes Under $300K in Middletown, NY

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20 of 47 Listings
Map

Homes Under $300K in Middletown, NY

20 of 47 Listings

  1. 191 Wickham Avenue — photo32

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas
Active

$245,000

4 bd · 2 ba · 1,613 sqft

191 Wickham Avenue, Middletown, NY

Virginia Corbett · eXp Realty

  • 91 Jimal Drive — photo35Active

    $259,000

    2 bd · 2 ba · 1,133 sqft

    91 Jimal Drive, Middletown, NY

    Darlene Brennan · Howard Hanna Rand Realty

  • 65 Jimal Drive — photo22Active

    $285,000

    2 bd · 2 ba · 1,133 sqft

    65 Jimal Drive, Middletown, NY

    Rebecca Kane · KW Hudson Valley United

  • 7 Harding Street — photo16Active

    $220,000

    1 bd · 1 ba · 980 sqft

    7 Harding Street, Middletown, NY

    Jonathon Z. Lee · KW Hudson Valley United

  • 41 Wallkill Avenue — photo19Active

    $265,000

    3 bd · 2 ba · 1,288 sqft

    41 Wallkill Avenue, Middletown, NY

    Frank Muccari · Cronin & Company Real Estate

  • 125 Deer Lane — photoPrice Reduced36Active

    $269,888

    3 bd · 2 ba · 1,021 sqft

    125 Deer Lane, Middletown, NY

    Joseph V. Lombardo · Lombardo Homes & Estates

  • 14 Brick Pond Road — photo25Active

    $220,000

    1 bd · 2 ba · 785 sqft

    14 Brick Pond Road, Middletown, NY

    Guy Cusumano · Howard Hanna Rand Realty

  • 629 New Kingston Road — photo26Active

    $295,000

    3 bd · 2 ba · 1,072 sqft

    629 New Kingston Road, Middletown, NY

    Derek Greene · The Greene Realty Group

  • 40 Academy Avenue — photoPrice Reduced16Active

    $295,000

    2 bd · 1 ba · 1,248 sqft

    40 Academy Avenue, Middletown, NY

    Jonathon Z. Lee · KW Hudson Valley United

  • 41 Irwin Avenue — photo27Active

    $299,000

    3 bd · 1 ba · 1,248 sqft

    41 Irwin Avenue, Middletown, NY

    Joshua Papka · KW Hudson Valley North

  • 538 Wagner Avenue — photo23Active

    $270,000

    3 bd · 2 ba · 1,312 sqft

    538 Wagner Avenue, Middletown, NY

    Joshua Slater · The Catskill Dream Team

  • 11 Brittany Drive — photoPrice Reduced42Active

    $199,000

    1 bd · 1 ba · 879 sqft

    11 Brittany Drive, Middletown, NY

    Amanda Ferrantello · Hudson Valley Griffith

  • 220 Upper Kennedy — photo42Active

    $299,000

    2 bd · 1 ba · 560 sqft

    220 Upper Kennedy, Middletown, NY

    Debra Smith · Coldwell Banker Timberland Properties

  • 63 Sycamore Drive 63 — photo25Active

    $289,000

    2 bd · 2 ba · 1,110 sqft

    63 Sycamore Drive 63, Middletown, NY

    Kyle Pierce · Patricia Schiller Real Est Co.

  • 901 Old Route 28 — photo30Active

    $299,000

    4 bd · 1 ba · 1,566 sqft

    901 Old Route 28, Middletown, NY

    Elizabeth A. McGuire · Keller Williams Upstate NY Properties

  • 256 Cottage Street — photo31Active

    $299,900

    3 bd · 1 ba · 860 sqft

    256 Cottage Street, Middletown, NY

    Brian J Caplicki · KW Hudson Valley United

  • 13 Birch Street — photoPrice Reduced9Active

    $105,000

    2 bd · 1 ba · 432 sqft

    13 Birch Street, Middletown, NY

    Patricia Lucey · Picture It Sold, LLC

  • 13 Ogden Street — photo27Active

    $260,000

    3 bd · 1 ba · 1,342 sqft

    13 Ogden Street, Middletown, NY

    Ronald Garafalo · Hudson Premium Realty

  • 141 Ruth Court — photo37Active

    $289,900

    2 bd · 2 ba · 1,049 sqft

    141 Ruth Court, Middletown, NY

    Dawn E. Gregg · Curasi Realty, Inc.

  • 16 Earle Street 14 1/2 — photo3Active

    $285,000

    2 bd · 1 ba · 1,019 sqft

    16 Earle Street 14 1/2, Middletown, NY

    Joao M Rodrigues · Preferred Properties Real Esta

  • 12

    Explore Middletown homes

    By price

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    By bedrooms

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    By type

    • Single family
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    By feature

    • New construction
    • With a pool
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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #10311208632

    Call Thomas

    Listing data & MLS disclosures

    OneKey MLS
    The data relating to real estate for sale on this website comes in part from the Internet Data exchange of OneKey MLS. IDX information is provided exclusively for consumers' 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 deemed reliable but not guaranteed. Copyright © 2026 OneKey MLS. All Rights Reserved
    New York State Alliance of MLSs
    The data relating to real estate for sale on this website comes in part from the Internet Data exchange (IDX) program of the New York State Alliance MLS. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Real estate listings held by brokerage firms other than Realty.com, are indicated by detailed information about them such as the name of the listing firms. All information deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change or withdrawal. Neither the listing broker(s) nor Realty.com shall be responsible for any typographical errors, misinformation, misprints, and shall be held totally harmless. Copyright ©2026 New York State Alliance and participating MLS's - CNYIS, UNYREIS and WNYREIS. All Rights Reserved.
    New York State Alliance of MLSs
    The data relating to real estate for sale on this website comes in part from the Internet Data exchange (IDX) program of the New York State Alliance MLS. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Real estate listings held by brokerage firms other than Realty.com, are indicated by detailed information about them such as the name of the listing firms. All information deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change or withdrawal. Neither the listing broker(s) nor Realty.com shall be responsible for any typographical errors, misinformation, misprints, and shall be held totally harmless. Copyright ©2026 New York State Alliance and participating MLS's - CNYIS, UNYREIS and WNYREIS. All Rights Reserved.

    Middletown, NY community profile

    Population
    31,152
    Median income
    $70,005
    Housing units
    12,399
    People per sq. mi.
    318.9
    Area
    97.7 sq. mi.

    Source: HJN community data

    Middletown housing market

    August 2026 · This period is still settling

    Middletown 12-month median sale price trend

    Selling at 101.4% of asking price

    Buyers here are paying above asking. MLS · 49 sales · as of Aug 31, 2026

    Homes that sold · County records, as of Aug 25, 2026

    Median sale price
    $448,500$367,500–$595,000 typical range
    Price per sq. ft.
    $263
    Sales
    35
    Paid in cash
    28.6%

    Homes on the market · MLS, as of Aug 24, 2026–Aug 31, 2026

    Median list price
    $450,000
    Homes for sale
    146
    Median days on market
    23 days

    Price trend · Assessor repeat sales, as of Aug 31, 2026

    Year-over-year
    15.6%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Aug 19, 2026

    Median home size
    1,694 sq. ft.