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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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22 of 44 Listings
Map

4 Bedroom Homes in Middletown, NY

22 of 44 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas
  1. 4 Harding Street — photoNew13Active

    $299,900

    4 bd · 2 ba · 1,416 sqft

    4 Harding Street, Middletown, NY

    Hai Li · KW Hudson Valley United

  2. 12 Westminister Drive — photo41Active

    $499,000

    4 bd · 3 ba · 1,848 sqft

    12 Westminister Drive, Middletown, NY

    Farzana Mian · Century 21 Full Service Realty

  3. 438 Dry Brook Road — photo38Active

    $415,000

    4 bd · 3 ba · 2,030 sqft

    438 Dry Brook Road, Middletown, NY

    Dara Barr · Keller Williams Upstate NY Properties

  4. 191 Wickham Avenue — photo32Active

    $245,000

    4 bd · 2 ba · 1,613 sqft

    191 Wickham Avenue, Middletown, NY

    Virginia Corbett · eXp Realty

  5. 907 Scotchtown Collabar Road — photo7Active

    $685,000

    4 bd · 3 ba · 2,887 sqft

    907 Scotchtown Collabar Road, Middletown, NY

    Brian T. Smith · River Realty Services, Inc.

  6. 1270 Roaring Brook Lane — photo33Active

    $725,000

    4 bd · 3 ba · 2,100 sqft

    1270 Roaring Brook Lane, Middletown, NY

    Sabrina L. Puppolo · Corcoran Country Living

  7. 44-50 Ingalls Street — photo5Active

    $550,000

    4 bd · 3 ba · 2,540 sqft

    44-50 Ingalls Street, Middletown, NY

    Sandra M. Arnez · KW Hudson Valley United

  8. 1413 Goshen Turnpike — photo18Active

    $469,000

    4 bd · 3 ba · 1,796 sqft

    1413 Goshen Turnpike, Middletown, NY

    Giulianna R. Rojas · Curasi Realty, Inc.

  9. 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

  10. 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

  11. 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.

  12. 151 Bowser Road — photo50Active

    $688,000

    4 bd · 3 ba · 2,646 sqft

    151 Bowser Road, Middletown, NY

    Zhiheng Tang · KW Hudson Valley United

  13. 8 Pine Street — photoPrice Reduced33Active

    $450,000

    4 bd · 2 ba · 2,152 sqft

    8 Pine Street, Middletown, NY

    Robin A White · KW Hudson Valley United

  14. 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

  15. 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

  16. 282 Derby Road — photo33Active

    $620,000

    4 bd · 3 ba · 2,354 sqft

    282 Derby Road, Middletown, NY

    Thomas E. Grazier · I Realty LLC

  17. 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

  18. 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

  19. 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.

  20. 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

  21. 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

  22. 19 Davidge Road — photo50Active

    $549,999

    4 bd · 4 ba · 2,298 sqft

    19 Davidge Road, Middletown, NY

    Kevin Grier · KW Hudson Valley United

12

Explore Middletown homes

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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #10311208632

    Call Thomas

    Middletown housing market

    August 2026 · This period is still settling

    Middletown 12-month median sale price trend

    Selling at 100.4% of asking price

    Sales here are closing essentially at asking. MLS · 48 sales · as of Aug 31, 2026

    Homes that sold · County records, as of Aug 28, 2026

    Median sale price
    $439,900$327,500–$595,000 typical range
    Price per sq. ft.
    $273
    Sales
    43
    Paid in cash
    32.6%

    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
    22 days

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

    Year-over-year
    10.4%

    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.

    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