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Homes with a Pool in Middletown, NY
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3 bedsWith a pool

Homes with a Pool in Middletown, NY

Homes with a Pool in Middletown, NY

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22 Listings
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Homes with a Pool in Middletown, NY

22 Listings

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Thomas O'Leary

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  1. 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

  2. 4 Francis Drive — photo44Active

    $499,999

    4 bd · 2 ba · 2,188 sqft

    4 Francis Drive, Middletown, NY

    Chativa Bowen · Keller Williams Realty

  3. 311 Howells Road — photo37Active

    $399,999

    3 bd · 1 ba · 1,188 sqft

    311 Howells Road, Middletown, NY

    Tehillah Deslandes · Howard Hanna Rand Realty

  4. 6 Beverly Road — photo31Active

    $549,900

    4 bd · 3 ba · 2,520 sqft

    6 Beverly Road, Middletown, NY

    Antoinette M Gundersen · HomeSmart Homes & Estates

  5. 51 Overhill Road — photo32Active

    $540,000

    3 bd · 2 ba · 1,850 sqft

    51 Overhill Road, Middletown, NY

    Dever Bruno · Four Points Realty Inc.

  6. 228 Thornapple Road — photo42Active

    $995,000

    3 bd · 3 ba · 2,726 sqft

    228 Thornapple Road, Middletown, NY

    Hillary Kolos · COMPASS Greater NY LLC

  7. 19 Putters Way Unit 9 — photo18Active

    $394,900

    2 bd · 3 ba · 1,337 sqft

    19 Putters Way Unit 9, Middletown, NY

    Christina Wilger · RE/MAX Benchmark Realty Group

  8. 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

  9. 487 Greenville Turnpike — photo19Active

    $470,000

    3 bd · 3 ba · 1,408 sqft

    487 Greenville Turnpike, Middletown, NY

    Antonette Theresa Vogel · BHG Real Estate Green Team

  10. 65 Maureen Drive — photo29Active

    $499,900

    3 bd · 2 ba · 2,200 sqft

    65 Maureen Drive, Middletown, NY

    Frank Muccari · Cronin & Company Real Estate

  11. 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

  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. 4 Woodrose Court — photoPrice Reduced34Active

    $435,000

    3 bd · 3 ba · 2,257 sqft

    4 Woodrose Court, Middletown, NY

    Alyssa Scancarello · Howard Hanna Rand Realty

  14. 34 Field Stone Drive — photoPrice Reduced21Active

    $449,000

    3 bd · 3 ba · 1,781 sqft

    34 Field Stone Drive, Middletown, NY

    Naomi Streicher · Q Home Sales

  15. 45 Brola Road — photo45Active

    $464,999

    3 bd · 3 ba · 1,966 sqft

    45 Brola Road, Middletown, NY

    Chativa Bowen · Keller Williams Realty

  16. 678 Prosperous Valley Road — photoPrice Reduced33Active

    $485,000

    4 bd · 2 ba · 1,861 sqft

    678 Prosperous Valley Road, Middletown, NY

    Yonauris E. Gonzalez Then · eXp Realty

  17. 202 Concord Lane — photoPrice Reduced41Active

    $349,000

    3 bd · 3 ba · 1,200 sqft

    202 Concord Lane, Middletown, NY

    Soleil Jackman · Howard Hanna Rand Realty

  18. 270 Kristens Ridge Road — photoPrice Reduced50Active

    $1,475,000

    4 bd · 5 ba · 4,199 sqft

    270 Kristens Ridge Road, Middletown, NY

    Jeffrey Ashton · Coldwell Banker Timberland Properties

  19. 238 S Centerville Road — photoPrice Reduced30Active

    $799,999

    5 bd · 3 ba · 3,764 sqft

    238 S Centerville Road, Middletown, NY

    Linda VanDeWeert · BHG Real Estate Green Team

  20. 352 Galli Curci Road — photo50Active

    $3,250,000

    9 bd · 7 ba · 2,700,000 sqft

    352 Galli Curci Road, Middletown, NY

    Sherret E. Chase · Four Seasons Sotheby's International Realty

  21. 352 Galli Curci — photo50Active

    $3,250,000

    7 bd · 7 ba · 8,276 sqft

    352 Galli Curci, Middletown, NY

    Sherret E. Chase · Four Seasons Sothebys Intl

  22. 390 Erpf Road — photoPrice Reduced50Active

    $8,500,000

    8 bd · 8 ba · 5,266 sqft

    390 Erpf Road, Middletown, NY

    Kathryn M. Johnson · William Pitt Sothebys Int Rlty

About Homes with a Pool in Middletown, NY

Homes with a Pool in Middletown, NY: 22 active listings as of October 23, 2026, 20:40 UTC.

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Listing information ©2026 New York State Alliance, Inc®. All Rights Reserved. Last Updated: 2026-10-01 19:23:23 UTC
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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

    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.