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3 beds
2 Bedroom Homes in Middletown, NY
45 listings

2 Bedroom Homes in Middletown, NY

2 Bedroom Homes in Middletown, NY

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22 of 45 Listings
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2 Bedroom Homes in Middletown, NY

22 of 45 Listings

  1. 100 Hillside Drive Unit B10 — photoNew35

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas
Active

$289,000

2 bd · 1 ba · 917 sqft

100 Hillside Drive Unit B10, Middletown, NY

Stephen Ramundo · Keller Williams Valley Realty

  • 197 Deer Ct Drive — photoOpen house Sun, Oct 25 · 1:00 PM32Active

    $339,000

    2 bd · 3 ba · 1,473 sqft

    197 Deer Ct Drive, Middletown, NY

    David L. White · Owner Entry.com

  • 85 Foster Road — photo40Active

    $625,000

    2 bd · 1 ba · 1,605 sqft

    85 Foster Road, Middletown, NY

    John R. Ruggieri · BHHS Hudson Valley Properties

  • 495 Union School Rd — photo14Active

    $949,000

    2 bd · — ba · — sqft

    495 Union School Rd, Middletown, NY

  • 102 Sproat Street — photo43Active

    $309,900

    2 bd · 1 ba · 778 sqft

    102 Sproat Street, Middletown, NY

    Peter Stika · Curasi Realty, Inc.

  • 17 Grant Street — photoPrice Reduced22Active

    $265,000

    2 bd · 2 ba · 960 sqft

    17 Grant Street, Middletown, NY

    Naomi Streicher · Q Home Sales

  • 33 Roosevelt Avenue — photo13Active

    $234,900

    2 bd · 1 ba · 848 sqft

    33 Roosevelt Avenue, Middletown, NY

    Nicole McCormick · BHG Real Estate Green Team

  • 54 Western Avenue — photo39Active

    $330,000

    2 bd · 1 ba · 962 sqft

    54 Western Avenue, Middletown, NY

    Catia S. Leon · eXp Realty

  • 412 4th Avenue — photo18Active

    $174,900

    2 bd · 2 ba · 924 sqft

    412 4th Avenue, Middletown, NY

    Sandra Spector · Howard Hanna Rand Realty

  • 136 Sycamore Drive — photoPrice Reduced17Active

    $299,900

    2 bd · 2 ba · 1,110 sqft

    136 Sycamore Drive, Middletown, NY

    Stacy Brescia-Spreer · Curasi Realty, Inc.

  • 15 N Aspen Road — photo15Active

    $299,000

    2 bd · 2 ba · 1,144 sqft

    15 N Aspen Road, Middletown, NY

    Carmela Lopez Borrazas · Serhant LLC

  • 138 Prospect Avenue — photo46Active

    $374,999

    2 bd · 1 ba · 1,422 sqft

    138 Prospect Avenue, Middletown, NY

    Gina Dudgeon · Howard Hanna Rand Realty

  • 243 Howells Turnpike — photo31Active

    $399,000

    2 bd · 1 ba · 960 sqft

    243 Howells Turnpike, Middletown, NY

    Steven Esposito · HomeSmart Homes & Estates

  • 24 Lilac Street — photo46Active

    $499,900

    2 bd · 2 ba · 1,473 sqft

    24 Lilac Street, Middletown, NY

    Lynelle D Alessi · KW Hudson Valley United

  • 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

  • 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 — photoPrice ReducedOpen house Sat, Oct 24 · 1:00 PM38Active

    $289,000

    2 bd · — ba · 864 sqft

    27 Bonnell Pl, Middletown, NY

  • 49 Brewster Drive — photoPrice ReducedOpen house Sat, Oct 24 · 11:00 AM35Active

    $349,000

    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 — photoPrice Reduced22Active

    $269,000

    2 bd · 2 ba · 1,133 sqft

    65 Jimal Drive, Middletown, NY

    Rebecca Kane · KW Hudson Valley United

  • 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

  • 120 Shaw Road — photo50Active

    $1,885,000

    2 bd · 2 ba · 1,280 sqft

    120 Shaw Road, Middletown, NY

    Antoinette M. Caruso · Stonewall Realty Group LLC

  • 12

    Explore Middletown homes

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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.

    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

    September 2026 · This period is still settling

    Middletown 12-month median sale price trend

    Selling at 100.0% of asking price

    Sales here are closing essentially at asking. MLS · 42 sales · as of Sep 30, 2026

    Homes that sold · County records, as of Sep 24, 2026

    Median sale price
    $425,000$315,000–$489,000 typical range
    Price per sq. ft.
    $221
    Sales
    21
    Paid in cash
    38.1%

    Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

    Median list price
    $469,000
    Homes for sale
    161
    Median days on market
    26 days

    Price trend · Assessor repeat sales, as of Sep 30, 2026

    Year-over-year
    4.9%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 9, 2026

    Median home size
    1,694 sq. ft.