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Middletown, NY Homes for Sale | Realty.com
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3 beds
203 listings
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New construction
With a pool

Homes for Sale in Middletown, NY

Homes for Sale in Middletown, NY

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21 of 203 Listings
Map

Homes for Sale in Middletown, NY

21 of 203 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas
  1. 220 Upper Kennedy — photoNew9Active

    $299,000

    2 bd · 1 ba · 560 sqft

    220 Upper Kennedy, Middletown, NY

    Debra Smith · Coldwell Banker Timberland Properties

  2. 50 Sycamore Drive 50 — photo35Active

    $329,900

    2 bd · 2 ba · 1,340 sqft

    50 Sycamore Drive 50, Middletown, NY

    Maliki Cottrell · Cottrell & Associates RE Corp.

  3. 3 Allerton Avenue — photo33Active

    $499,000

    3 bd · 3 ba · 1,328 sqft

    3 Allerton Avenue, Middletown, NY

    Erin K Connolly-Frontino · Artisan Realty

  4. 751 County Route 3 — photoNew29Active

    $225,000

    3 bd · 1 ba · 1,050 sqft

    751 County Route 3, Middletown, NY

    Susan Fairbairn · The Catskill Dream Team

  5. 608 Kirbytown Road — photo25Active

    $350,000

    2 bd · 1 ba · 1,007 sqft

    608 Kirbytown Road, Middletown, NY

    Carol M Buchanan · BHG Real Estate Green Team

  6. 34 Field Stone Drive — photo21Active

    $485,000

    3 bd · 3 ba · 1,781 sqft

    34 Field Stone Drive, Middletown, NY

    Naomi Streicher · Q Home Sales

  7. 18 Deer Ct Drive Building 19 Unit 18 — photo17Active

    $320,000

    2 bd · 2 ba · 1,291 sqft

    18 Deer Ct Drive Building 19 Unit 18, Middletown, NY

    David B Wilson · Hudson Premium Realty

  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. 35 Lexington Way — photo3Active

    $319,000

    2 bd · 3 ba · 1,348 sqft

    35 Lexington Way, Middletown, NY

    Zhiheng Tang · KW Hudson Valley United

  10. 473 Ingrassia Road — photo50Active

    $759,900

    4 bd · 3 ba · 2,572 sqft

    473 Ingrassia Road, Middletown, NY

    John N Biasi · Howard Hanna Rand Realty

  11. 43 Brick Pond Road — photo22Active

    $328,000

    3 bd · 3 ba · 1,460 sqft

    43 Brick Pond Road, Middletown, NY

    Hai Li · KW Hudson Valley United

  12. 41 Clinton Street — photo5Active

    $335,000

    3 bd · 1 ba · 1,224 sqft

    41 Clinton Street, Middletown, NY

    Ernest Acampora · River Realty Services, Inc.

  13. 63 Sycamore Drive 63 — photo25Active

    $289,000

    2 bd · 2 ba · 1,110 sqft

    63 Sycamore Drive 63, Middletown, NY

    Kyle Pierce · Patricia Schiller Real Est Co.

  14. 93 Meadow View Drive — photo46Active

    $489,999

    3 bd · 4 ba · 1,827 sqft

    93 Meadow View Drive, Middletown, NY

    Kevin Grier · Keller Williams Hudson Valley

  15. 901 Old Route 28 — photo28Active

    $299,000

    4 bd · 1 ba · 1,566 sqft

    901 Old Route 28, Middletown, NY

    Elizabeth A. McGuire · Keller Williams Upstate NY Properties

  16. 256 Cottage Street — photo31Active

    $299,900

    3 bd · 1 ba · 860 sqft

    256 Cottage Street, Middletown, NY

    Brian J Caplicki · KW Hudson Valley United

  17. 21 Black Stallion Court — photo31Active

    $359,000

    3 bd · 2 ba · 1,388 sqft

    21 Black Stallion Court, Middletown, NY

    Liene Kasparsons · Keller Williams Realty

  18. 23 W Conkling Avenue — photo43Active

    $415,000

    4 bd · 3 ba · 1,625 sqft

    23 W Conkling Avenue, Middletown, NY

    Sandra M. Arnez · KW Hudson Valley United

  19. 13 Birch Street — photo9Active

    $115,000

    2 bd · 1 ba · 432 sqft

    13 Birch Street, Middletown, NY

    Patricia Lucey · Picture It Sold, LLC

  20. 45 Randall Heights — photo35Active

    $549,000

    3 bd · 3 ba · 2,053 sqft

    45 Randall Heights, Middletown, NY

    Sandra M. Arnez · KW Hudson Valley United

  21. 43 Mayer Drive — photo43Active

    $385,000

    3 bd · 3 ba · 1,496 sqft

    43 Mayer Drive, Middletown, NY

    Wenpeng Guan · KW Hudson Valley United

12…9

Explore Middletown homes

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Listing data & MLS disclosures

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
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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

    Nearby areas

    ZIP codes

    • 10940 (123)
    • 12701 (78)
    • 12790 (57)
    • 12586 (49)
    • 12566 (43)
    • 12721 (37)
    • 12737 (36)
    • 12775 (36)

    Cities

    • Monticello (73)
    • Wurtsboro (55)
    • Walden (48)
    • Pine Bush (41)
    • Bloomingburg (36)
    • Glen Spey (36)
    • Rock Hill (36)
    • Montgomery (34)

    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.