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Single-Family Homes in Highland, NY
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3 beds
46 listings
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Single-Family Homes in Highland, NY

Single-Family Homes in Highland, NY

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22 of 46 Listings
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Single-Family Homes in Highland, NY

22 of 46 Listings

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Thomas O'Leary

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  1. 53 Devlin Road — photo28Active

    $419,000

    3 bd · 2 ba · 1,344 sqft

    53 Devlin Road, Highland, NY

    Edward Rabon · Compass Greater NY, LLC

  2. 44 Airport Road — photo42Active

    $493,000

    3 bd · 3 ba · 1,456 sqft

    44 Airport Road, Highland, NY

    Caroline Akt · Caroline Akt Realty LLC

  3. 66 Highland Lake Road — photo42Active

    $449,000

    4 bd · 3 ba · 3,194 sqft

    66 Highland Lake Road, Highland, NY

    Michael Friedmann · eRealty Advisors, Inc

  4. 943 State Route 55 — photo36Active

    $389,000

    3 bd · 2 ba · 1,500 sqft

    943 State Route 55, Highland, NY

    Joy Romano · Joy Romano Realty

  5. 38 Devenoge Drive — photo46Active

    $715,000

    4 bd · 2 ba · 1,772 sqft

    38 Devenoge Drive, Highland, NY

    Dawn M. Payne · Payne Team LLC

  6. 3426 State Route 97 — photo7Active

    $145,600

    2 bd · 1 ba · 1,440 sqft

    3426 State Route 97, Highland, NY

    Jamarr C. Zellner · REALHome Services & Solutions

  7. 24 Frazier Road — photoPrice Reduced13Active

    $250,000

    3 bd · 2 ba · 960 sqft

    24 Frazier Road, Highland, NY

    Sean Walker · Keller Williams Realty

  8. 76 Timber Lake Drive — photoPrice Reduced41Active

    $694,000

    3 bd · 3 ba · 1,900 sqft

    76 Timber Lake Drive, Highland, NY

    Erik Freeland · Country House Realty Inc

  9. 3 Rennenberg Road — photo27Active

    $385,000

    2 bd · 1 ba · 1,092 sqft

    3 Rennenberg Road, Highland, NY

    Donna M Geba · Century 21 Geba Realty

  10. 220 Mail Road — photoPrice Reduced21Active

    $339,000

    3 bd · 2 ba · 1,252 sqft

    220 Mail Road, Highland, NY

    Loretta Wolff · NexLvl Real Estate Inc.

  11. 26 Summit Drive — photoPrice Reduced33Active

    $579,000

    3 bd · 3 ba · 2,380 sqft

    26 Summit Drive, Highland, NY

    Kristen Payne · Payne Team LLC

  12. 167 Timber Lake Drive — photoPrice Reduced47Active

    $1,050,000

    3 bd · 3 ba · 2,815 sqft

    167 Timber Lake Drive, Highland, NY

    Erica Keberle · Anatole House LLC

  13. 223 Yulan-Barryville Road — photoPrice Reduced37Active

    $180,000

    1 bd · 1 ba · 777 sqft

    223 Yulan-Barryville Road, Highland, NY

    Barry Becker · KW Hudson Valley United

  14. 91 Airport Road — photo50Active

    $399,900

    3 bd · 2 ba · 1,430 sqft

    91 Airport Road, Highland, NY

    Patti Martell · Payne Team LLC

  15. 171 Yulan Barryville Road — photo23Active

    $379,000

    3 bd · 2 ba · 1,384 sqft

    171 Yulan Barryville Road, Highland, NY

    Chris C. Somerville · Cabins & Canoes Real Estate

  16. 60 Highland Lake Road — photoPrice Reduced33Active

    $449,999

    3 bd · 2 ba · 1,560 sqft

    60 Highland Lake Road, Highland, NY

    Pedrina Martinez · Listing Pro Realty Services

  17. 142 Split Rock Drive — photoPrice Reduced45Active

    $425,000

    4 bd · 3 ba · 2,240 sqft

    142 Split Rock Drive, Highland, NY

    Alan R. Wieder · Catskills Home Services

  18. 5 Steges Road — photo19Active

    $249,000

    3 bd · 1 ba · 1,008 sqft

    5 Steges Road, Highland, NY

    Dali Levy · KW Hudson Valley United

  19. 80 Beaver Brook Road — photoPrice Reduced31Active

    $405,000

    2 bd · 1 ba · 1,300 sqft

    80 Beaver Brook Road, Highland, NY

    Dawn J. Curreri · Eagle Valley Realty

  20. 4 Tow Path Road — photo18Active

    $850,000

    2 bd · 1 ba · 2,948 sqft

    4 Tow Path Road, Highland, NY

    Caroline Akt · Caroline Akt Realty LLC

  21. 17 Collins Road — photo37Active

    $485,000

    0 bd · 2 ba · 5,600 sqft

    17 Collins Road, Highland, NY

    Donna M Geba · Century 21 Geba Realty

  22. 91 Crawford Road — photo50Active

    $8,500,000

    5 bd · 6 ba · 4,939 sqft

    91 Crawford Road, Highland, NY

    John C. Schmitt · Davis R Chant Real Estate Inc.

12

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Listing data & MLS disclosures

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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 construction
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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #10311208632

    Call Thomas

    Highland, NY community profile

    Area
    46.6 sq. mi.

    Source: HJN community data

    Highland housing market

    August 2026 · This period is still settling

    Highland 12-month median sale price trend

    Homes that sold · County records, as of Aug 25, 2026

    Median sale price
    $265,000$184,500–$431,250 typical range
    Sales
    11
    Paid in cash
    54.6%

    Homes on the market · MLS, as of Aug 24, 2026

    Median list price
    $547,500
    Homes for sale
    26

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

    Year-over-year
    -28.4%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Aug 20, 2026

    Median home size
    1,710 sq. ft.