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4 Bedroom Homes in Middletown, NY
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3 bedsNew constructionWith a pool

4 Bedroom Homes in Middletown, NY

4 Bedroom Homes in Middletown, NY

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23 of 54 Listings
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4 Bedroom Homes in Middletown, NY

23 of 54 Listings

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TO

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas
  1. 106 Freezer Road — photo50Active

    $549,900

    4 bd · 3 ba · 2,916 sqft

    106 Freezer Road, Middletown, NY

    Christine Koenig · Keller Williams Realty

  2. 1270 Roaring Brook Lane — photoNew32Active

    $725,000

    4 bd · 3 ba · 2,100 sqft

    1270 Roaring Brook Lane, Middletown, NY

    Sabrina L. Puppolo · Corcoran Country Living

  3. 44-50 Ingalls Street — photoNew5Active

    $550,000

    4 bd · 3 ba · 2,540 sqft

    44-50 Ingalls Street, Middletown, NY

    Sandra M. Arnez · KW Hudson Valley United

  4. 1413 Goshen Turnpike — photo18Active

    $469,000

    4 bd · 3 ba · 1,796 sqft

    1413 Goshen Turnpike, Middletown, NY

    Giulianna R. Rojas · Curasi Realty, Inc.

  5. 326 North Street — photo22Active

    $510,000

    4 bd · 3 ba · 2,308 sqft

    326 North Street, Middletown, NY

    Ahida L. Mercado · Real Broker NY LLC

  6. 19-21 Lincoln Terrace 19 — photo48Active

    $899,900

    4 bd · 4 ba · 3,699 sqft

    19-21 Lincoln Terrace 19, Middletown, NY

    Patricia M Sassi · RE/MAX Benchmark Realty Group

  7. 289 Pine Grove Road — photo50Active

    $1,150,000

    4 bd · 4 ba · 5,360 sqft

    289 Pine Grove Road, Middletown, NY

    Pedro Garcia · Curasi Realty, Inc.

  8. 8 Pine Street — photo33Active

    $475,000

    4 bd · 3 ba · 2,152 sqft

    8 Pine Street, Middletown, NY

    Robin A White · KW Hudson Valley United

  9. 473 Ingrassia Road — photoPrice Reduced50Active

    $699,900

    4 bd · 3 ba · 2,572 sqft

    473 Ingrassia Road, Middletown, NY

    John N Biasi · Howard Hanna Rand Realty

  10. 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

  11. 282 Derby Road — photo33Active

    $599,900

    4 bd · 3 ba · 2,354 sqft

    282 Derby Road, Middletown, NY

    Thomas E. Grazier · I Realty LLC

  12. 34 Hawthorne Drive — photo49Active

    $579,000

    4 bd · 3 ba · 2,368 sqft

    34 Hawthorne Drive, Middletown, NY

    Linda A Clark · Hudson Valley Griffith

  13. 130 Apple Lane Drive — photo33Active

    $730,000

    4 bd · 3 ba · 2,646 sqft

    130 Apple Lane Drive, Middletown, NY

    Kichka Pascaru · Douglas Elliman Real Estate

  14. 50 Scott Drive — photo45Active

    $489,000

    4 bd · 2 ba · 1,796 sqft

    50 Scott Drive, Middletown, NY

    Dulce M Ferrera · KW Hudson Valley United

  15. 1215 Route 211 W — photoPrice Reduced47Active

    $579,000

    4 bd · 3 ba · 2,832 sqft

    1215 Route 211 W, Middletown, NY

    Matthew W. Gibbs · KW Hudson Valley United

  16. 21 Harrison Street — photoPrice Reduced50Active

    $419,900

    4 bd · 2 ba · 1,560 sqft

    21 Harrison Street, Middletown, NY

    Jie Liu · KW Hudson Valley United

  17. 1 Hulse Street — photo46Active

    $499,000

    4 bd · 3 ba · 2,388 sqft

    1 Hulse Street, Middletown, NY

    Anita S. Cristiano · HomeSmart Homes & Estates

  18. 977 Mt Hope Road — photo50Active

    $599,000

    4 bd · 3 ba · 2,428 sqft

    977 Mt Hope Road, Middletown, NY

    Georgina T. Maynard · Charles Rutenberg Realty, Inc.

  19. 276 Spruce Road — photo38Active

    $499,000

    4 bd · 3 ba · 2,688 sqft

    276 Spruce Road, Middletown, NY

    Christine Torres · Keller Williams Hudson Valley

  20. 158 Reiss Road — photoPrice Reduced46Active

    $789,900

    4 bd · 3 ba · 3,958 sqft

    158 Reiss Road, Middletown, NY

    Danielle Bartula · Howard Hanna Rand Realty

  21. 118 Ridge Drive — photo49Active

    $765,000

    4 bd · 3 ba · 3,064 sqft

    118 Ridge Drive, Middletown, NY

    Patricia M Sassi · RE/MAX Benchmark Realty Group

  22. 241 Midland Lake Road — photo7Active

    $849,999

    4 bd · 3 ba · 2,862 sqft

    241 Midland Lake Road, Middletown, NY

    Hilary R. Goldman · Howard Hanna Rand Realty

  23. 19 Davidge Road — photo50Active

    $549,999

    4 bd · 4 ba · 2,298 sqft

    19 Davidge Road, Middletown, NY

    Kevin Grier · KW Hudson Valley United

123

Explore Middletown homes

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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.
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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #10311208632

    Call Thomas

    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

    July 2026 · This period is still settling

    Middletown 12-month median sale price trend

    Selling at 101.7% of asking price

    Buyers here are paying above asking. MLS · 43 sales · as of Jul 31, 2026

    Homes that sold · County records, as of Jul 31, 2026

    Median sale price
    $400,000$250,750–$513,500 typical range
    Price per sq. ft.
    $229
    Sales
    39
    Paid in cash
    59.0%

    Homes on the market · MLS, as of Jul 21, 2026–Jul 31, 2026

    Median list price
    $444,500
    Homes for sale
    132
    Median days on market
    27 days

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

    Year-over-year
    -5.3%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 15, 2026

    Median home size
    1,692 sq. ft.