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Homes Under $300K in Middletown, NY
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3 beds

Homes Under $300K in Middletown, NY

Homes Under $300K in Middletown, NY

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20 of 60 Listings
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Homes Under $300K in Middletown, NY

20 of 60 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas
  1. 17 Grant Street — photo22Active

    $289,000

    2 bd · 2 ba · 960 sqft

    17 Grant Street, Middletown, NY

    Naomi Streicher · Q Home Sales

  2. 4 Harding Street — photo17Active

    $299,900

    4 bd · 2 ba · 1,416 sqft

    4 Harding Street, Middletown, NY

    Wenpeng Guan · KW Hudson Valley United

  3. 33 Roosevelt Avenue — photo13Active

    $234,900

    2 bd · 1 ba · 848 sqft

    33 Roosevelt Avenue, Middletown, NY

    Nicole McCormick · BHG Real Estate Green Team

  4. 32 Abraham Joseph Circle 32 — photo12Active

    $99,000

    3 bd · — ba · 1,232 sqft

    32 Abraham Joseph Circle 32, Middletown, NY

  5. 412 4th Avenue — photo18Active

    $174,900

    2 bd · 2 ba · 924 sqft

    412 4th Avenue, Middletown, NY

    Sandra Spector · Howard Hanna Rand Realty

  6. 13 Jimal Drive — photo23Active

    $289,900

    3 bd · 3 ba · 1,245 sqft

    13 Jimal Drive, Middletown, NY

    Ronald Garafalo · Hudson Premium Realty

  7. 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.

  8. 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

  9. 122 Sycamore Drive — photo35Active

    $199,000

    1 bd · 1 ba · 830 sqft

    122 Sycamore Drive, Middletown, NY

    Christina Wilger · RE/MAX Benchmark Realty Group

  10. 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

  11. 27 Bonnell Pl — photoPrice Reduced38Active

    $289,000

    2 bd · — ba · 864 sqft

    27 Bonnell Pl, Middletown, NY

  12. 132 Sycamore Drive — photo18Active

    $284,900

    2 bd · 2 ba · 1,342 sqft

    132 Sycamore Drive, Middletown, NY

    Stacy Brescia-Spreer · Curasi Realty, Inc.

  13. 91 Jimal Drive — photo35Active

    $259,000

    2 bd · 2 ba · 1,133 sqft

    91 Jimal Drive, Middletown, NY

    Darlene Brennan · Howard Hanna Rand Realty

  14. 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

  15. 7 Harding Street — photoPrice Reduced18Active

    $209,000

    1 bd · 1 ba · 980 sqft

    7 Harding Street, Middletown, NY

    Jonathon Z. Lee · KW Hudson Valley United

  16. 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

  17. 14 Brick Pond Road — photo25Active

    $220,000

    1 bd · 2 ba · 785 sqft

    14 Brick Pond Road, Middletown, NY

    Christina Rowan · Howard Hanna Rand Realty

  18. 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

  19. 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

  20. 538 Wagner Avenue — photo23Active

    $270,000

    3 bd · 2 ba · 1,312 sqft

    538 Wagner Avenue, Middletown, NY

    Joshua Slater · The Catskill Dream Team

123

About Homes Under $300K in Middletown, NY

Homes Under $300K in Middletown, NY: 60 active listings as of October 18, 2026, 22:42 UTC.

Property types among these 60 listings, by the property type each listing’s MLS reports, spelled as the MLS spells it. Types with fewer than 5 listings, and listings whose MLS reports no type, are not shown, so the shares can total less than 100%.
Property typeListingsShare
Single Family Residence3761.7%
Condominium1626.7%

Explore Middletown homes

By price

  • Homes Under $300K
  • Homes Under $400K
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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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Listing data & MLS disclosures

NYSShare
Listing information provided by NYSShare.
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

  • Homes Under $700K

    By bedrooms

    • 2 Bedroom Homes
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    • 4 Bedroom Homes

    By type

    • Single-Family Homes
    • Condos

    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #10311208632

    Call Thomas

    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.