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3 beds
Homes Under $400K in Middletown, NY
97 listings

Homes Under $400K in Middletown, NY

Homes Under $400K in Middletown, NY

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20 of 97 Listings
Map

Homes Under $400K in Middletown, NY

20 of 97 Listings

  1. 122 Sycamore Drive — photo1Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas

$199,000

1 bd · 1 ba · 830 sqft

122 Sycamore Drive, Middletown, NY

Christina Wilger · RE/MAX Benchmark Realty Group

  • 8 Keystone Park — photoNew28Active

    $399,000

    3 bd · 1 ba · 912 sqft

    8 Keystone Park, Middletown, NY

    Frank Muccari · Cronin & Company Real Estate

  • 19 Putters Way 9 — photo18Active

    $394,900

    2 bd · 3 ba · 1,337 sqft

    19 Putters Way 9, Middletown, NY

    Christina Wilger · RE/MAX Benchmark Realty Group

  • 4 Harding Street — photo13Active

    $299,900

    4 bd · 2 ba · 1,416 sqft

    4 Harding Street, Middletown, NY

    Hai Li · KW Hudson Valley United

  • 55 Orange Terrace — photo39Active

    $325,000

    3 bd · 1 ba · 1,092 sqft

    55 Orange Terrace, Middletown, NY

    Virginia Corbett · eXp Realty

  • 143 Deer Ct Drive — photo35Active

    $299,000

    2 bd · 2 ba · 1,291 sqft

    143 Deer Ct Drive, Middletown, NY

    Martha Randazzo · Howard Hanna Rand Realty

  • 27 Bonnell Pl — photo38Active

    $299,000

    2 bd · — ba · 864 sqft

    27 Bonnell Pl, Middletown, NY

  • 132 Sycamore Drive — photo18Active

    $284,900

    2 bd · 2 ba · 1,342 sqft

    132 Sycamore Drive, Middletown, NY

    Stacy Brescia-Spreer · Curasi Realty, Inc.

  • 191 Wickham Avenue — photo32Active

    $245,000

    4 bd · 2 ba · 1,613 sqft

    191 Wickham Avenue, Middletown, NY

    Virginia Corbett · eXp Realty

  • 3 Moriah Lane — photo50Active

    $369,000

    2 bd · 2 ba · 1,922 sqft

    3 Moriah Lane, Middletown, NY

    Anita S. Cristiano · HomeSmart Homes & Estates

  • 49 Brewster Drive — photo35Active

    $369,000

    2 bd · 2 ba · 1,136 sqft

    49 Brewster Drive, Middletown, NY

    Kismet L. Johnson · 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 — photo17Active

    $224,000

    1 bd · 1 ba · 980 sqft

    7 Harding Street, Middletown, NY

    Jonathon Z. Lee · KW Hudson Valley United

  • 13 Old Anvil Lane — photo32Active

    $380,000

    3 bd · 3 ba · 1,692 sqft

    13 Old Anvil Lane, Middletown, NY

    Hilary R. Goldman · Howard Hanna Rand Realty

  • 125 Deer Lane — photoPrice Reduced36Active

    $265,888

    2 bd · 1 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

  • 580 Route 17M — photo40Active

    $350,000

    5 bd · 2 ba · 1,914 sqft

    580 Route 17M, Middletown, NY

    Matthew W. Gibbs · KW Hudson Valley United

  • 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

  • 12…5

    Explore Middletown homes

    By price

    • Homes Under $300K
    • Homes Under $400K
    • Homes Under $500K
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    • Homes Under $700K

    By bedrooms

    • 2 Bedroom Homes
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    • 4 Bedroom Homes

    By type

    • Single-Family Homes
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    The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #10311208632

    Call Thomas

    Listing data & MLS disclosures

    NY State MLS
    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.
    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 100.7% 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 28, 2026

    Median sale price
    $432,450$321,250–$547,500 typical range
    Price per sq. ft.
    $269
    Sales
    50
    Paid in cash
    34.0%

    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
    22 days

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

    Year-over-year
    9.7%

    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.