6,490

Highland, NY Homes

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  • /2

    $350,000

    • Land
    • 14.5 Acres
    • $24,138 per Acre

    (Lot 3) 111 South St, Highland, NY 12528

    Build your custom dream home on this shovel-ready 13-acre homesite in a newly approved and recorded 4-lot subdivision totaling nearly 49 acres. All the hard work is done: perc test completed, well & septic approved by the Ulster County Board of Health, and electric & fiber already run to the shared driveway. Accessed via a common driveway, the lot offers privacy and a natural Hudson Valley

    Agent Photo

    Mark Friedman

    McGrath Realty Inc

    (Lot 3) 111 South St, Highland, NY 12528
  • /9

    Starting at $2,350 Per Month

    • 2 Beds

    42 Toc Dr, Highland, NY 12528

    Welcome to your new home in the heart of Highland, NY! This apartment community offers comfort and convenience in a prime location. Situated just steps away from the scenic rail trail and the iconic Mid-Hudson Bridge, outdoor enthusiasts will love the easy access to biking, walking, and breathtaking views. If you're a commuter, the nearby train station provides a stress-free option for travel.

    Trailview Place

    42 Toc Dr, Highland, NY 12528
  • /39

    $415,000

    Sold Jun 03, 2026

    3 Commercial Ave, Highland, NY 12528

    • 3 Beds
    • 1.5 Baths
    • 1,176 Sq Ft
    • Built 1920

    Last Sold Summary

    • 4% Above List Price
    • $353/SF
    • 32 Days On Market

    Current Estimated Value $412,325

    Last Listing Agent Savannah Miceli Century 21 Alliance-NP

    3 Commercial Ave, Highland, NY 12528
    • 32 Timber Lake Dr, Highland, NY 12792

      Not Listed For Sale

      32 Timber Lake Dr, Highland, NY 12792

      • 3 Beds
      • 2 Baths
      • 1,768 Sq Ft
      • Built 2007
      32 Timber Lake Dr, Highland, NY 12792

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Erik Freeland Country House Realty Inc

  • /2

    $185,000

    • Land
    • 10,454 Sq Ft
    • $770,833 per Acre

    224 Vineyard Ave, Highland, NY 12528

    Recent home demolished and removed. .24 acre lot with town water and sewer (Natural gas on the street but not to the lot). 1.5 miles to the Hamlet of Highland. Ask us about our custom home affordability program.

    Agent Photo

    Danielle Carlson-Murphy

    Start Home Smart, Inc.

    224 Vineyard Ave, Highland, NY 12528
  • /2

    Starting at $1,595 Per Month

    • 1 - 2 Beds

    210 Vineyard Ave, Highland, NY 12528

    Located minutes from the Mid-Hudson Bridge, 4 miles from Vassar Hospital. Quiet brookside location. One mile from the quaint shops in the town of Highland.

    Brookside Apartments

    210 Vineyard Ave, Highland, NY 12528
  • 25 Mile Hill Rd, Highland, NY 12528

    $450,000

    Sold Mar 23, 2026

    25 Mile Hill Rd, Highland, NY 12528

    • 4 Beds
    • 2 Baths
    • 1,516 Sq Ft
    • Built 1995

    Last Sold Summary

    • 6% Above List Price
    • $297/SF
    • 29 Days On Market

    Current Estimated Value $457,628

    Last Listing Agent Dan Axtmann BHHS Hudson Valley Properties

    25 Mile Hill Rd, Highland, NY 12528
    • 274 Fosler Rd, Highland, NY 12528

      Est $614,717

      Not Listed For Sale

      274 Fosler Rd, Highland, NY 12528

      • 4 Beds
      • 3 Baths
      • 2,197 Sq Ft
      • Built 2023
      274 Fosler Rd, Highland, NY 12528

      Last Sold Summary

      • 78 Days On Market

      Last Listing Agent Richard Baxter Keller Williams Realty

  • /12

    $135,000

    $15K PRICE DROP Pending
    • 2 Beds
    • 1 Bath
    • 552 Sq Ft

    407 Swartekill Rd, Highland, NY 12528

    Charming 2-Bedroom Mobile Home on 1.29 Acres in Swartekill Neighborhood Discover the potential of this cozy 2-bedroom, 1-bathroom mobile home nestled on a spacious 1.29-acre lot in the desirable Swartekill neighborhood, located in the Town of Esopus and within the sought-after New Paltz School District. This property offers a unique opportunity for those looking to invest, renovate, or create

    Agent Photo

    Kristen Zigouras

    eXp Realty

    407 Swartekill Rd, Highland, NY 12528
  • /34

    Starting at $3,655 Per Month

    • 2 - 3 Beds

    6142 Merlot Dr, Highland, NY 12528

    Vineyard Commons offers a fresh approach to active adult living, combining comfort, convenience and style. Our spacious two and three bedroom apartments feature vaulted ceilings, abundant closet space and gourmet kitchens with granite countertops and stainless steel appliances, all on a single level for effortless living. Enjoy the freedom to do as much or as little as you like with amenities

    Vineyard Commons

    6142 Merlot Dr, Highland, NY 12528
  • 56 Beaver Brook Rd, Highland, NY 12792

    $550,000

    Sold May 19, 2026

    56 Beaver Brook Rd, Highland, NY 12792

    • 2 Beds
    • 2 Baths
    • 960 Sq Ft
    • Built 1935

    Last Sold Summary

    • $573/SF
    • 21 Days On Market

    Current Estimated Value $532,741

    Last Listing Agent Caroline Akt Caroline Akt Realty LLC

    56 Beaver Brook Rd, Highland, NY 12792
    • 321 Perkinsville Rd, Highland, NY 12528

      Est $660,474

      Not Listed For Sale

      321 Perkinsville Rd, Highland, NY 12528

      • 3 Beds
      • 2.5 Baths
      • 2,214 Sq Ft
      • Built 2010
      321 Perkinsville Rd, Highland, NY 12528

      Last Sold Summary

      • 32 Days On Market

      Last Listing Agent Pamela Kandel Houlihan Lawrence Inc.

  • /2

    $200,000

    • Land
    • 6.2 Acres
    • $32,258 per Acre

    0 Vineyard Ave Unit 20256184, Highland, NY 12528

    Rare find. 6.2 acres with town water, sewer and gas. 1/2 zoning can have single family, multi family and multiple units.

    Agent Photo

    Danielle Carlson-Murphy

    Start Home Smart, Inc.

    0 Vineyard Ave Unit 20256184, Highland, NY 12528
  • /15

    Starting at $2,250 Per Month

    • 2 Beds

    Orchard Hill Cir, Highland, NY 12528

    Explore the ideal sanctuary in Highland, New York! This vibrant community boasts a mix of 2 and 3 bedroom townhouses and 1 bedroom studios. Revel in the convenient proximity to local boutiques, dining establishments, and the full spectrum of Highland's amenities. Furthermore, the nearby rail trail beckons outdoor enthusiasts and nature admirers, creating an exceptional refuge for strolls, jogs,

    Orchard Hills

    Orchard Hill Cir, Highland, NY 12528
  • 18 Hillside Place, Highland, NY 12528

    $210,000

    Sold Mar 17, 2026

    18 Hillside Place, Highland, NY 12528

    • 2 Beds
    • 1 Bath
    • 1,096 Sq Ft
    • Built 1950

    Last Sold Summary

    • 5% Below List Price
    • $192/SF
    • 130 Days On Market

    Current Estimated Value $218,984

    Last Listing Agent Brian Smith River Realty Services, Inc.

    18 Hillside Place, Highland, NY 12528
    • 799 State Route 44 55, Highland, NY 12528

      Est $483,158

      Not Listed For Sale

      799 State Route 44 55, Highland, NY 12528

      • 4 Beds
      • 3 Baths
      • 1,750 Sq Ft
      • Built 1949
      799 State Route 44 55, Highland, NY 12528

      Last Sold Summary

      • 23 Days On Market

      Last Listing Agent Andre Aivazians HomeSmart Homes & Estates

  • /8

    $195,000

    • Land
    • 22.3 Acres
    • $8,744 per Acre

    0 Crawford Rd Unit KEY821449, Highland, NY 12528

    Beautiful wooded 22.3 acre parcel along quaint Crawford Road just outside of the charming Delaware river hamlet of Barryville. Close to Eldred, Yulan, Barryville, Narrowsburg and the Delaware River.

    Agent Photo

    Rosemarie DeCristofaro

    Callicoon Real Estate LLC

    0 Crawford Rd Unit KEY821449, Highland, NY 12528
  • /15

    Starting at $1,550 Per Month

    • 1 Bed

    3501 9w Route, Highland, NY 12528

    Welcome to Highland Crossing Community in Highland, New York! Our newly renovated one-bedroom apartments, nestled near the charming village of Highland, provide cozy living for those who love small-town life. Each unit is modern and comfortable, offering a touch of rustic charm. Located near the village, you'll have easy access to local shops, restaurants, and community events, while enjoying the

    Highland Crossing

    3501 9w Route, Highland, NY 12528
  • /64

    $700,000

    Sold Apr 03, 2026

    11 Tricia Blvd, Highland, NY 12528

    • 4 Beds
    • 2.5 Baths
    • 3,526 Sq Ft
    • Built 1999

    Last Sold Summary

    • 103,604% Above List Price
    • $199/SF
    • 23 Days On Market

    Current Estimated Value $692,976

    Last Listing Agent Dawn Passante Coldwell Banker Village GreenN

    11 Tricia Blvd, Highland, NY 12528
    • 94 Glen Rock Cir, Highland, NY 12528

      Est $609,769

      Not Listed For Sale

      94 Glen Rock Cir, Highland, NY 12528

      • 3 Beds
      • 3 Baths
      • 2,100 Sq Ft
      • Built 2012
      94 Glen Rock Cir, Highland, NY 12528

      Last Sold Summary

      • 21 Days On Market

      Last Listing Agent JOHN SCARANO Keller Williams Realty

  • /40

    $450,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 2,260 Sq Ft

    573 Plutarch Rd, Highland, NY 12528

    *Multiple offers - highest and best by 6/3 at 5pm* A rare opportunity awaits at this striking contemporary estate, nestled on over 11 acres of absolute privacy within the highly desirable New Paltz School District. Situated on a quiet country road, this four-bedroom, two and a half bathroom home is a true diamond in the rough, offering the perfect canvas for a buyer with the vision and means to

    Agent Photo

    Kristen Zigouras

    eXp Realty

    573 Plutarch Rd, Highland, NY 12528
  • /4

    $1,825

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 850 Sq Ft
    • Condo for Rent

    109 Grand St Unit Grand Street, Highland, NY 12528

    Two bedroom upstairs apartment. Unique layout with heat included.Private setting.

    109 Grand St Unit Grand Street, Highland, NY 12528
  • 194 Vineyard Ave, Highland, NY 12528

    $540,000

    Sold Aug 04, 2026

    194 Vineyard Ave, Highland, NY 12528

    • 3 Beds
    • 3 Baths
    • 2,329 Sq Ft
    • Built 2004

    Last Sold Summary

    • 10% Below List Price
    • $232/SF
    • 81 Days On Market

    Current Estimated Value $536,455

    Last Listing Agent Angela Briante Briante Realty Group, LLC

    194 Vineyard Ave, Highland, NY 12528
    • /14

      Est $374,246

      Not Listed For Sale

      8 Marie, Highland, NY 12528

      • 3 Beds
      • 2 Baths
      • 1,720 Sq Ft
      • Built 1900
      8 Marie, Highland, NY 12528

      Last Sold Summary

      • 119 Days On Market

      Last Listing Agent Angela Paul Past Member

  • /2

    $325,000

    • Land
    • 9.7 Acres
    • $33,505 per Acre

    (Lot 1) 111 South St, Highland, NY 12528

    Build your custom dream home on this shovel-ready 9,7-acre homesite in a newly approved and recorded 4-lot subdivision totaling nearly 49 acres. All the hard work is done: perc test completed, well & septic approved by the Ulster County Board of Health, and electric & fiber already run to the shared driveway. Accessed via a common driveway, the lot offers privacy and a natural Hudson Valley

    Agent Photo

    Mark Friedman

    McGrath Realty Inc

    (Lot 1) 111 South St, Highland, NY 12528
  • /12

    $2,500

    Total Monthly Price

    • 2 Beds
    • 2.5 Baths
    • 1,396 Sq Ft
    • Townhouse for Rent

    101 Sterling Place, Highland, NY 12528

    Two bedroom with a loft townhouse style unit. Home features two and half baths, laundry in the unit and a garage. Lovely deck off living room. Updated kitchen with nice nook for the kitchen table. Tenant pays all utilities including water and sewer. Close to bridge, walkway and shopping.

    101 Sterling Place, Highland, NY 12528
  • 16 Trout Brook Ln, Highland, NY 12528

    $185,000

    Sold Jan 21, 2026

    16 Trout Brook Ln, Highland, NY 12528

    • 2 Beds
    • 2 Baths
    • 1,456 Sq Ft
    • Built 2017

    Last Sold Summary

    • 24% Below List Price
    • $127/SF
    • 58 Days On Market

    Last Listing Agent Lisa Cozzolino Cronin & Company Real Estate

    16 Trout Brook Ln, Highland, NY 12528
    • /35

      Est $641,816

      Not Listed For Sale

      135 Chapel Hill Rd, Highland, NY 12528

      • 3 Beds
      • 2.5 Baths
      • 2,650 Sq Ft
      • Built 2018
      135 Chapel Hill Rd, Highland, NY 12528

      Last Sold Summary

      • 31 Days On Market

      Last Listing Agent Lindsay Stevens eXp Realty

  • /3

    $150,000

    • Land
    • 6.7 Acres
    • $22,388 per Acre

    0 Highland Lake Rd Unit KEY868497, Highland, NY 12732

    Located just outside of the charming hamlet of Eldred, this wooded parcel provides access to the spectacular Halfway Brook with rushing waters and waterfall along the rear property line. This area of the Hudson Valley provides easy access to the Delaware River for fishing, rafting & canoeing. It also provides plenty of opportunities for outdoor recreation, camping and hunting. It's a hop, skip

    Theresa Powers

    Keller Williams Realty

    0 Highland Lake Rd Unit KEY868497, Highland, NY 12732
  • /27

    $1,650 - $2,150

    Total Monthly Price

    • 1 - 2 Beds
    • 1 Bath
    • 500 Sq Ft
    • Condo for Rent

    3 White St, Highland, NY 12528

    Live in the heart of Highland just steps from local shops, restaurants, cafes, parks, and the center of town while still enjoying the comfort of a quiet residential setting.This well maintained property offers a rare combination of convenience, character, and Hudson Valley charm. Located minutes from the Mid Hudson Bridge, Walkway Over the Hudson, New Paltz, the Poughkeepsie waterfront,

    3 White St, Highland, NY 12528
  • 283 Hawleys Corners Rd, Highland, NY 12528

    $327,000

    Sold Nov 20, 2025

    283 Hawleys Corners Rd, Highland, NY 12528

    • 3 Beds
    • 1 Bath
    • 1,816 Sq Ft
    • Built 1900

    Last Sold Summary

    • 9% Below List Price
    • $180/SF
    • 74 Days On Market

    Current Estimated Value $367,951

    Last Listing Agent Dawn Passante Coldwell Banker Village Green

    283 Hawleys Corners Rd, Highland, NY 12528
    • 10 Sollazzo Ln, Highland, NY 12528

      Est $145,560

      Not Listed For Sale

      10 Sollazzo Ln, Highland, NY 12528

      10 Sollazzo Ln, Highland, NY 12528

      Last Sold Summary

      • 234 Days On Market

      Last Listing Agent Margareta Schmoll Curasi Realty, Inc.

  • /20

    $649,999

    • 4 Beds
    • 3 Baths
    • 2,241 Sq Ft

    217 Tuckers Corners Rd, Highland, NY 12528

    NEW CONSTRUCTION!!! Estimated to be completed by beginning of August. This stunning new construction ranch-style home offers 2,241 square feet of refined, single-level living space featuring four spacious bedrooms, three full bathrooms, and an attached two-car garage, all set on a sprawling and private 8.90-acre estate within the Marlboro School District. While the foundation for luxury is set,

    Agent Photo

    Richard Baxter

    Keller Williams Realty

    217 Tuckers Corners Rd, Highland, NY 12528
  • /28

    $2,300 Per Month

    • 2 Beds
    • 1 Bath
    • 2,802 Sq Ft
    • Apartment for Rent

    3 White St, Highland, NY 12528

    Welcome to 3 White Street in Highland, NY! This well-maintained 2-bedroom apartment offers comfortable living in a convenient location close to local shops, restaurants, and commuter routes. The apartment features a spacious layout with access to an on-site washer and dryer located in the basement for added convenience. Water and garbage removal are included in the monthly rent, helping to

    Genevieve Rolleri eXp Realty

    3 White St, Highland, NY 12528
    • 9 Elbow Ln, Highland, NY 12528

      Est $1,514,607

      Not Listed For Sale

      9 Elbow Ln, Highland, NY 12528

      • 4 Beds
      • Built 2024
      9 Elbow Ln, Highland, NY 12528

      Last Sold Summary

      • 229 Days On Market

      Last Listing Agent Christopher Acuti RE/MAX Town & Country

  • /28

    $449,900

    Pending
    • 3 Beds
    • 3 Baths
    • 1,664 Sq Ft

    3 Lauretta Dr, Highland, NY 12528

    Completely renovated and move-in ready, this stylish raised ranch offers three bedrooms, a finished lower level, and a spacious backyard designed for entertaining. The main level features hardwood flooring throughout, a vaulted living room with a decorative fireplace, an updated kitchen with brand-new cabinetry, countertops, and stainless steel appliances, and fully renovated bathrooms. The

    Agent Photo

    Patrycja Warda

    Corcoran Country Living

    3 Lauretta Dr, Highland, NY 12528
  • /31

    $6,128

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,496 Sq Ft
    • Condo for Rent

    62 Mackey Rd Unit SI ID1621787P, Highland, NY 12528

    The advertised rate of $6,129/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 29, 2026. Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

    62 Mackey Rd Unit SI ID1621787P, Highland, NY 12528
  • 616 N Elting Corners Rd, Highland, NY 12528

    $420,000

    Sold Jun 03, 2026

    616 N Elting Corners Rd, Highland, NY 12528

    • 3 Beds
    • 1 Bath
    • 1,556 Sq Ft
    • Built 1996

    Last Sold Summary

    • 5% Above List Price
    • $270/SF
    • 13 Days On Market

    Current Estimated Value $418,148

    Last Listing Agent Carla DeMarsh DeMarsh Properties Inc.

    616 N Elting Corners Rd, Highland, NY 12528

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