Highland, NY Homes

• 

  $35,000

  Sold Dec 11, 2025

  0 Split Rock Dr Unit ONEH6305826, Highland, NY 12719

  • Land
  • 6.06 Acres
  • $5,776 per Acre

  Last Sold Summary

  • 27% Below List Price
  • 547 Days On Market

  Last Listing Agent Gibson McKean Payne Team LLC

  0 Split Rock Dr Unit ONEH6305826, Highland, NY 12719
• 

  Est $636,176

  Not Listed For Sale

  17 Mayer Dr, Highland, NY 12528

  • 4 Beds
  • 2.5 Baths
  • 2,342 Sq Ft
  • Built 2004

  17 Mayer Dr, Highland, NY 12528

  Last Sold Summary

  • 41 Days On Market

  Last Listing Agent Dani Dorman Real Broker NY LLC
• 

  

  

  /19

  $175,000

  Pending

  • 4 Beds
  • 4 Baths
  • 2,962 Sq Ft

  25 Phillips Ave, Highland, NY 12528

  Opportunity awaits at 25 Phillips Avenue in the heart of Highland! Situated on a spacious and private lot surrounded by mature trees, this 3-family property offers endless potential for investors, contractors, or buyers looking to restore and customize a large multi-unit home in a desirable Ulster County location. Offering approximately 2,962 square feet, the property features expansive living

  Ronald Green KW Mid-Hudson

  25 Phillips Ave, Highland, NY 12528
• 

  

  

  /25

  $214,000

  Sold Jul 29, 2026

  109 Hawleys Corners Rd, Highland, NY 12528

  • 4 Beds
  • 1 Bath
  • 1,530 Sq Ft
  • Built 1900

  Last Sold Summary

  • 19% Above List Price
  • $140/SF
  • 21 Days On Market

  Current Estimated Value $297,215

  Last Listing Agent Megan forziati Coldwell Banker Village GreenN

  109 Hawleys Corners Rd, Highland, NY 12528
• 

  Est $460,241

  Not Listed For Sale

  39 Mayer Dr, Highland, NY 12528

  • 3 Beds
  • 2 Baths
  • 1,844 Sq Ft
  • Built 1968

  39 Mayer Dr, Highland, NY 12528

  Last Sold Summary

  • 40 Days On Market

  Last Listing Agent Michele Spignardo KW Hudson Valley United
• 

  

  /8

  $450,000

  • Land
  • 2.04 Acres
  • $220,588 per Acre

  0 Lake View Dr Unit KEY857198, Highland, NY 12743

  Discover your dream retreat on this stunning lakefront vacant land located on Highland Lake, one of Sullivan County's premier motorboat lakes. With an established driveway and dock already in place, this property offers easy access to endless recreational opportunities, from fishing to boating to everything in between. Imagine building your perfect getaway, surrounded by breathtaking views and

  Dawn Payne Payne Team LLC

  0 Lake View Dr Unit KEY857198, Highland, NY 12743
• 

  $465,000

  Sold Sep 04, 2026

  11 Cuomo Dr, Highland, NY 12528

  • 3 Beds
  • 2 Baths
  • 1,820 Sq Ft
  • Built 1985

  Last Sold Summary

  • $255/SF
  • 39 Days On Market

  Current Estimated Value $472,620

  Last Listing Agent JoAnn Ellis Summerset Realty

  11 Cuomo Dr, Highland, NY 12528
• 

  Est $306,633

  Not Listed For Sale

  411 Vineyard Ave, Highland, NY 12528

  • 3 Beds
  • 1 Bath
  • 1,040 Sq Ft
  • Built 1963

  411 Vineyard Ave, Highland, NY 12528

  Last Sold Summary

  • 141 Days On Market

  Last Listing Agent Brian Smith River Realty Services, Inc.
• 

  

  /6

  $299,000

  Pre-Foreclosure

  • 3 Beds
  • 2 Baths
  • 1,425 Sq Ft

  933 South St, Highland, NY 12528

  Opportunity awaits on this private 4.52-acre property in the Town of Plattekill. Nestled among mature trees, this property features a 3-bedroom, 2-bath Cape Cod home with approximately 1,425 square feet of living space, a detached garage, and additional outbuildings. The home is being sold strictly as-is and presents an excellent opportunity for investors, contractors, or buyers looking to

  Zak Abdullah Weichert New Homes Co

  933 South St, Highland, NY 12528
• 

  $375,000

  Sold Nov 18, 2025

  27 Amato Ln, Highland, NY 12528

  • 2 Beds
  • 1 Bath
  • 1,050 Sq Ft
  • Built 1930

  Last Sold Summary

  • $357/SF
  • 22 Days On Market

  Current Estimated Value $386,707

  Last Listing Agent Jacob Cohen eXp Realty

  27 Amato Ln, Highland, NY 12528
• 

  Est $452,375

  Not Listed For Sale

  12 Van Wagner Rd, Highland, NY 12528

  • 3 Beds
  • 2 Baths
  • 1,582 Sq Ft
  • Built 1985

  12 Van Wagner Rd, Highland, NY 12528

  Last Sold Summary

  • 44 Days On Market

  Last Listing Agent Danielle Siltz RE/MAX Prime Properties
• 

  

  /31

  $479,000

  $21K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,844 Sq Ft

  41 Penny Ln, Highland, NY 12528

  Welcome to 41 Penny Lane, a beautifully maintained, move-in ready 3-bedroom, 2.5-bath ranch that has been lovingly cared for nearly 40 years. Tucked away on a quiet, private, dead-end road and set on a picturesque 0.52-acre lot, this 1,844-square-foot home offers easy, single-level living with a wonderful connection to the outdoors. Walk in and you're greeted by an open, light-filled living

  Jacob Cohen eXp Realty

  41 Penny Ln, Highland, NY 12528
• 

  $758,000

  Sold Oct 17, 2025

  2 Fieldstone Ct, Highland, NY 12528

  • 4 Beds
  • 2.5 Baths
  • 3,253 Sq Ft
  • Built 2005

  Last Sold Summary

  • 1% Below List Price
  • $233/SF
  • 107 Days On Market

  Current Estimated Value $853,565

  Last Listing Agent Joseph Brown RE/MAX Real Property Group

  2 Fieldstone Ct, Highland, NY 12528
• 

  

  /27

  Est $422,245

  Not Listed For Sale

  4 Van Wagner Rd, Highland, NY 12528

  • 3 Beds
  • 3 Baths
  • 1,812 Sq Ft
  • Built 1946

  4 Van Wagner Rd, Highland, NY 12528

  Last Sold Summary

  • 32 Days On Market

  Last Listing Agent Danielle Carlson-Murphy Start Home Smart, Inc.
• 

  

  /24

  $429,900

  Pending

  • 4 Beds
  • 2.5 Baths
  • 2,191 Sq Ft

  26 Lauretta Dr, Highland, NY 12528

  Tucked away on a quiet dead-end road and set high with scenic mountain views, this well-maintained split ranch is ready for its next chapter in the Hudson Valley. Freshly painted and move-in ready, the home features 4 bedrooms and 2.5 bathrooms, along with a wood-burning fireplace and newly finished wood floors that add warmth and character throughout. A beautiful sunroom with three walls of

  Syndi Acampora eXp Realty

  26 Lauretta Dr, Highland, NY 12528
• 

  $335,000

  Sold Nov 13, 2025

  87 Sterling Place, Highland, NY 12528

  • 2 Beds
  • 2.5 Baths
  • 1,396 Sq Ft
  • Built 1988

  Last Sold Summary

  • $240/SF
  • 90 Days On Market

  Current Estimated Value $369,744

  Last Listing Agent Mark Snyder eXp Realty

  87 Sterling Place, Highland, NY 12528
• 

  Est $346,296

  Not Listed For Sale

  16 Fair St, Highland, NY 12528

  • 4 Beds
  • 2 Baths
  • 1,408 Sq Ft
  • Built 1923

  16 Fair St, Highland, NY 12528

  Last Sold Summary

  • 161 Days On Market

  Last Listing Agent Lynne Riccoboni BHHS Hudson Valley Properties
• 

  

  /55

  $1,425,000

  $75K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,520 Sq Ft

  60 Palazzo Ln, Highland, NY 12528

  This bold custom built home sits atop a hill like a postcard extolling the beauty of the Hudson Valley. Built to exacting specifications and with an understanding of how people live best by a master craftsman, this is a post and beam masterpiece in an inspiring setting. Uniquely, it offers all the bells and whistles you expect in a new luxury home while also feeling like an heirloom. Set on 4

  Dawn Passante Coldwell Banker Village GreenN

  60 Palazzo Ln, Highland, NY 12528
• 

  

  /40

  $359,900

  Sold Dec 30, 2025

  466 New Paltz Rd, Highland, NY 12528

  • 2 Beds
  • 2 Baths
  • 1,438 Sq Ft
  • Built 1954

  Last Sold Summary

  • $250/SF
  • 35 Days On Market

  Current Estimated Value $393,895

  Last Listing Agent Justin Phillips United Real Estate HV Edge

  466 New Paltz Rd, Highland, NY 12528
• 

  Est $352,186

  Not Listed For Sale

  21 Maple Ave, Highland, NY 12528

  • 3 Beds
  • 1 Bath
  • 1,477 Sq Ft
  • Built 1943

  21 Maple Ave, Highland, NY 12528

  Last Sold Summary

  • 41 Days On Market

  Last Listing Agent Margaret Thorne KW MidHudson
• 

  

  /33

  $480,000

  Under Contract

  • 4 Beds
  • 2 Baths
  • 2,640 Sq Ft

  98 North Rd, Highland, NY 12528

  This charming 1900 farmhouse in Highland offers a comfortable and spacious living space with original wide custom moldings and beautiful oak hardwood flooring. Enjoy the beautiful sunlight in the fully finished sunroom. The kitchen is open with plenty of counter space and new appliances. There's a large dining area for large gatherings or intimate dinners. The primary bedroom is on the first

  Dawn Passante Coldwell Banker Village GreenN

  98 North Rd, Highland, NY 12528
• 

  $225,000

  Sold Sep 03, 2026

  33 Mile Hill Rd, Highland, NY 12528

  • 2 Beds
  • 1 Bath
  • 964 Sq Ft
  • Built 1900

  Last Sold Summary

  • $233/SF
  • 45 Days On Market

  Current Estimated Value $244,806

  Last Listing Agent Martin Krakower eXp Realty

  33 Mile Hill Rd, Highland, NY 12528
• 

  

  /22

  Est $372,576

  Not Listed For Sale

  33 Grand St, Highland, NY 12528

  • 3 Beds
  • 2 Baths
  • 1,340 Sq Ft
  • Built 1865

  33 Grand St, Highland, NY 12528

  Last Sold Summary

  • 19 Days On Market

  Last Listing Agent Gabrielle Edwards Past Member
• 

  

  /50

  $529,000

  Pending

  • 7 Beds
  • 4 Baths

  53 Main St, Highland, NY 12528

  Some properties ask you to be patient. This one puts money in your pocket from closing day.Fully occupied and cash flowing, this commercial-residential multi-family sits on Main Street in the heart of Highland, steps from the Walkway Over the Hudson, one of the most visited destinations in the entire Hudson Valley. Two tenanted units. Month-to-month leases. Current rents below market

  Amy McArdle eXp Realty

  53 Main St, Highland, NY 12528
• 

  $205,000

  Sold Sep 22, 2025

  614 Plutarch Rd, Highland, NY 12528

  • 3 Beds
  • 1 Bath
  • 1,434 Sq Ft
  • Built 1870

  Last Sold Summary

  • 17% Above List Price
  • $143/SF
  • 18 Days On Market

  Current Estimated Value $373,936

  Last Listing Agent Bonnie Christman BHHS Hudson Valley Properties

  614 Plutarch Rd, Highland, NY 12528
• 

  Est $359,863

  Not Listed For Sale

  43 Grand St, Highland, NY 12528

  • 3 Beds
  • 1.5 Baths
  • 1,317 Sq Ft
  • Built 1929

  43 Grand St, Highland, NY 12528

  Last Sold Summary

  • 68 Days On Market

  Last Listing Agent Ginalea Healy K. Fortuna Realty, Inc.
• 

  

  /30

  $545,000

  • 3 Beds
  • 2.5 Baths
  • 1,682 Sq Ft

  9 Emerson Terrace, Lloyd, NY 12528

  Welcome to Mountainside Woods, where luxury, comfort, and convenience come together.Why wait for new construction when you can move right into this stunning former model home in the highly sought-after Mountainside Woods community? Thoughtfully designed with both style and functionality in mind, this beautifully appointed home is loaded with premium upgrades.The gourmet kitchen serves as

  Megan Krusen eXp Realty

  9 Emerson Terrace, Lloyd, NY 12528
• 

  

  /33

  $422,300

  Sold Jan 02, 2026

  6 Smith Terrace, Highland, NY 12528

  • 4 Beds
  • 3 Baths
  • 1,728 Sq Ft
  • Built 1956

  Last Sold Summary

  • 6% Below List Price
  • $244/SF
  • 58 Days On Market

  Current Estimated Value $455,144

  Last Listing Agent Virginia Corbett Past Member

  6 Smith Terrace, Highland, NY 12528
• 

  Est $386,810

  Not Listed For Sale

  18 Woodside Place, Highland, NY 12528

  • 3 Beds
  • 1 Bath
  • 1,312 Sq Ft
  • Built 1957

  18 Woodside Place, Highland, NY 12528

  Last Sold Summary

  • 22 Days On Market

  Last Listing Agent Alejandra Fermin Empire Fine Homes
• 

  

  /28

  $558,000

  • 3 Beds
  • 2 Baths
  • 1,580 Sq Ft

  7 Tina Dr, Highland, NY 12528

  Tucked along a quiet dead-end street in Highland, this inviting three-bedroom, two-bath home offers nearly 1,600 square feet of thoughtfully updated living space, along with the kind of backyard that makes summer feel like a vacation at home.The bright main level has an easy, comfortable flow, with hardwood floors, a spacious living room and a beautifully renovated kitchen featuring

  Donna Brooks Compass Greater New York, LLC

  7 Tina Dr, Highland, NY 12528
• 

  $465,000

  Sold Sep 25, 2025

  155 Tuckers Corners Rd, Highland, NY 12528

  • 5 Beds
  • 4 Baths
  • 1,890 Sq Ft
  • Built 1928

  Last Sold Summary

  • 3% Above List Price
  • $246/SF
  • 36 Days On Market

  Current Estimated Value $489,046

  Last Listing Agent Anais O'Connor Compass Greater NY, LLC

  155 Tuckers Corners Rd, Highland, NY 12528
• 

  /2

  Est $386,600

  Not Listed For Sale

  20 Woodside Place, Highland, NY 12528

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Built 1953

  20 Woodside Place, Highland, NY 12528
• 

  

  /19

  $429,000

  • 4 Beds
  • 2 Baths
  • 1,443 Sq Ft

  1 Jackman St, Highland, NY 12528

  Discover the charm of this quaint four-bedroom craftsman style home, nestled on a quiet private road in the Village of Highland. Filled with character, the home features beautiful original woodwork and hardwood floors that showcase its timeless appeal. Outside, the inviting yard provides a peaceful setting to relax, entertain, or simply enjoy the tranquility of home.What truly makes this

  Dawn Passante Coldwell Banker Village Green

  1 Jackman St, Highland, NY 12528
• 

  $432,000

  Sold Jun 15, 2026

  491 Floyd Ackert Rd, Highland, NY 12528

  • 3 Beds
  • 1 Bath
  • 1,500 Sq Ft
  • Built 1982

  Last Sold Summary

  • 13% Below List Price
  • $288/SF
  • 78 Days On Market

  Current Estimated Value $447,628

  Last Listing Agent Dawn Passante Coldwell Banker Village Green

  491 Floyd Ackert Rd, Highland, NY 12528
• 

  

  /35

  Est $393,042

  Not Listed For Sale

  6 Meadow St, Highland, NY 12528

  • 3 Beds
  • 2 Baths
  • 1,570 Sq Ft
  • Built 1920

  6 Meadow St, Highland, NY 12528

  Last Sold Summary

  • 67 Days On Market

  Last Listing Agent Angela Paul Past Member
• 

  

  /13

  $500,000

  $195K PRICE DROP

  • Land
  • 11.5 Acres
  • $43,478 per Acre

  TBD Route 9w, Highland, NY 12528

  Attention Investors! 11.5 acres located just minutes from the Mid-Hudson Bridge in desirable Highland, NY ready for developing. Ideally located on a high traffic state highway with over 1,000 feet of road frontage and tons of visibility. This lot sits directly across the highway from the future river front development named "The Hudson Valley Wine Village" which is proposed to have 800 new

  John Quinn Quinn Realty Group Inc

  TBD Route 9w, Highland, NY 12528
• 

  $434,000

  Sold Nov 26, 2025

  4 Salk Dr, Highland, NY 12528

  • 3 Beds
  • 1.5 Baths
  • 1,934 Sq Ft
  • Built 1959

  Last Sold Summary

  • 9% Above List Price
  • $224/SF
  • 29 Days On Market

  Current Estimated Value $453,003

  Last Listing Agent Barbara Korabel Four Seasons Realty Group

  4 Salk Dr, Highland, NY 12528
• 

  

  /22

  Est $309,411

  Not Listed For Sale

  23 Grove St, Highland, NY 12528

  • 2 Beds
  • 1 Bath
  • 772 Sq Ft
  • Built 1942

  23 Grove St, Highland, NY 12528

  Last Sold Summary

  • 36 Days On Market

  Last Listing Agent Laurel Sweeney BHHS Nutshell Realty
• 

  

  /15

  $169,900

  $5K PRICE DROP

  • Land
  • 5.84 Acres
  • $29,092 per Acre

  0 Crawford Rd Unit KEY983986, Highland, NY 12528

  Escape to the peace and beauty of the Sullivan County Catskills with this lovely 5.8-acre parcel on Crawford Rd in the Town of Highland. Partially cleared and very private, this property offers the perfect setting to build your dream home in the country. Imagine relaxing on your future front porch or back deck while watching eagles soar overhead, enjoying star-filled skies, and taking in the

  Dominick Tufano RE/MAX Benchmark Realty Group

  0 Crawford Rd Unit KEY983986, Highland, NY 12528
• 

  $90,000

  Sold Aug 11, 2026

  10 Thorns Ln, Highland, NY 12528

  • Land
  • 39,639 Sq Ft
  • $98,901 per Acre

  Last Sold Summary

  • 1% Above List Price
  • 32 Days On Market

  Last Listing Agent Virginia Corbett eXp Realty

  10 Thorns Ln, Highland, NY 12528

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