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Highland, NY Homes for Sale — Page 2 | Realty.com
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43 listings
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Homes for Sale in Highland, NY

Homes for Sale in Highland, NY

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19 of 43 Listings
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Homes for Sale in Highland, NY

19 of 43 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas
  1. 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

  2. 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

  3. 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.

  4. 3 Perry Road — photoPrice Reduced20Active

    $409,000

    2 bd · 1 ba · 828 sqft

    3 Perry Road, Highland, NY

    Jonathan Sunshine · The Sunshine Group Real Estate

  5. 113 Airport Road — photoPrice Reduced46Active

    $1,395,000

    4 bd · 5 ba · 4,852 sqft

    113 Airport Road, Highland, NY

    Edward Rabon · Compass Greater NY, LLC

  6. 16 Fairway Drive — photo40Active

    $499,000

    3 bd · 2 ba · 1,632 sqft

    16 Fairway Drive, Highland, NY

    Dawn M. Payne · Payne Team LLC

  7. 55 Woods Road — photoPrice Reduced50Active

    $2,325,000

    4 bd · 3 ba · 2,965 sqft

    55 Woods Road, Highland, NY

    Edward Rabon · Compass Greater NY, LLC

  8. 35 Washington Lake Road — photo41Active

    $2,700,000

    16 bd · 11 ba · 11,160 sqft

    35 Washington Lake Road, Highland, NY

    Loretta Wolff · NexLvl Real Estate Inc.

  9. 87 Airport Road — photoPrice Reduced31Active

    $329,000

    3 bd · 3 ba · 2,000 sqft

    87 Airport Road, Highland, NY

    Donna M Geba · Century 21 Geba Realty

  10. 238 Lakeview Drive Road — photoPrice Reduced23Active

    $900,000

    11 bd · 7 ba · 4,762 sqft

    238 Lakeview Drive Road, Highland, NY

    Joseph A. LaBarbera · KW Hudson Valley United

  11. 110 Eldred Yulan Road — photoPrice Reduced23Active

    $799,000

    4 bd · 2 ba · 2,400 sqft

    110 Eldred Yulan Road, Highland, NY

    Caroline Akt · Caroline Akt Realty LLC

  12. 21 Crawford Road — photoPrice Reduced48Active

    $699,000

    3 bd · 2 ba · 1,605 sqft

    21 Crawford Road, Highland, NY

    Dawn M. Payne · Payne Team LLC

  13. 86 Beaver Brook Road — photoPrice Reduced50Active

    $649,000

    4 bd · 5 ba · 3,940 sqft

    86 Beaver Brook Road, Highland, NY

    Barry Becker · KW Hudson Valley United

  14. 18 York Avenue — photoPrice Reduced48Active

    $241,777

    3 bd · 2 ba · 1,396 sqft

    18 York Avenue, Highland, NY

    Jose A. Portillo · Portillo Realty Corp

  15. 609 State Route 55 — photoPrice Reduced12Active

    $189,000

    2 bd · 1 ba · 860 sqft

    609 State Route 55, Highland, NY

    Natalie Rajsz Steimle · Century 21 Geba Realty

  16. 125 Mapes Road — photoPrice Reduced46Active

    $1,470,000

    5 bd · 4 ba · 3,463 sqft

    125 Mapes Road, Highland, NY

    Donna M Geba · Century 21 Geba Realty

  17. 50 Park Road — photoPrice Reduced14Active

    $299,700

    3 bd · 2 ba · 1,164 sqft

    50 Park Road, Highland, NY

    Nicholas Ralph · Nestquest Direct LLC

  18. 140 Highland Lake Road — photoPrice Reduced34Active

    $239,000

    2 bd · 2 ba · 1,020 sqft

    140 Highland Lake Road, Highland, NY

    Lorraine K Smith · Century 21 Geba Realty

  19. 180 Yulan Barryville Road — photoPrice Reduced50Active

    $989,000

    4 bd · 3 ba · 2,643 sqft

    180 Yulan Barryville Road, Highland, NY

    Caroline Akt · Caroline Akt Realty LLC

12
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The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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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
  • Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #10311208632

    Call Thomas

    Nearby areas

    ZIP codes

    • 12771 (66)
    • 12701 (58)
    • 12775 (33)
    • 12726 (28)
    • 12737 (27)
    • 12754 (26)
    • 12764 (25)
    • 12790 (25)

    Cities

    • Port Jervis (46)
    • Liberty (41)
    • Middletown (10)

    Highland, NY community profile

    Area
    46.6 sq. mi.

    Source: HJN community data

    Highland housing market

    October 2026 · This period is still settling

    Selling at 100.1% of asking price

    Sales here are closing essentially at asking. MLS · 10 sales · as of Oct 23, 2026

    Homes on the market · MLS, as of Oct 18, 2026–Oct 23, 2026

    Median list price
    $489,000
    Homes for sale
    44
    Median days on market
    32 days

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 30, 2026

    Median home size
    1,711 sq. ft.