Highland, NY Homes

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  /65

  $1,100,000

  • 3 Beds
  • 3.5 Baths
  • 4,572 Sq Ft

  74 Bellevue Rd, Highland, NY 12528

  Hudson River Views! This inviting home combines comfort, character, and convenience with a dramatic two-story foyer and open floor plan. Enjoy a cozy living room with a gas fireplace, formal dining area overlooking the river, and a kitchen with custom cherry cabinets, granite counters, and Jenn Air cooktop. A flexible room with French doors makes a great office or fourth bedroom. Bathroom and

  Hollis Dukler Coldwell Banker Village GreenN

  74 Bellevue Rd, Highland, NY 12528
• 

  

  

  /15

  $2,250 Per Month

  • 2 Beds
  • 1 Bath
  • 936 Sq Ft
  • House for Rent

  230 Hawleys Corners Rd, Highland, NY 12528

  Virtually staged for inspiration- Escape to a renovated, immaculate cottage tucked into a serene, natural wooded setting. Perfect for nature lovers, this peaceful retreat offers total privacy while remaining just minutes from mass transit and a short 80-mile drive to New York City. Bright, spotless interiors, a washer and dryer in the basement, and beautiful forest views make this the ideal blend

  Nancy Senescu Bella NS Properties LLC

  230 Hawleys Corners Rd, Highland, NY 12528
• 

  $499,000

  Sold Feb 03, 2026

  123 Vineyard Ave, Highland, NY 12528

  • 4 Beds
  • 3 Baths
  • 2,400 Sq Ft
  • Built 1900

  Last Sold Summary

  • 17% Below List Price
  • $208/SF
  • 68 Days On Market

  Current Estimated Value $504,979

  Last Listing Agent Dawn Passante Coldwell Banker Village Green

  123 Vineyard Ave, Highland, NY 12528
• 

  

  

  /35

  Est $501,989

  Not Listed For Sale

  27 Ose Rd, Highland, NY 12528

  • 3 Beds
  • 2 Baths
  • 1,972 Sq Ft
  • Built 1998

  27 Ose Rd, Highland, NY 12528

  Last Sold Summary

  • 5 Days On Market
• 

  

  

  /17

  $27,500

  $7K PRICE DROP

  • Land
  • 1.09 Acres
  • $25,229 per Acre

  0 Eldred-Yulan Rd Unit KEY979887, Highland, NY 12792

  Cleared 1.09 acre building lot atop a hill with a view of Bodine Lake. Lot has been cleared for home site and has a drilled well in place. Septic plans and survey on file.

  Cara Rieber Rieber Realty Inc

  0 Eldred-Yulan Rd Unit KEY979887, Highland, NY 12792
• 

  $51,000

  Sold Oct 31, 2025

  0 Summit Dr Unit KEYH6318306, Highland, NY 12732

  • Land
  • 5.04 Acres
  • $10,119 per Acre

  Last Sold Summary

  • 14% Below List Price
  • 361 Days On Market

  Last Listing Agent Dawn Payne Payne Team LLC

  0 Summit Dr Unit KEYH6318306, Highland, NY 12732
• 

  Est $749,552

  Not Listed For Sale

  131 Baileys Gap Rd, Highland, NY 12528

  • 4 Beds
  • 3.5 Baths
  • 2,713 Sq Ft
  • Built 2002

  131 Baileys Gap Rd, Highland, NY 12528

  Last Sold Summary

  • 20 Days On Market
• 

  

  /7

  $175,000

  • Land
  • 6.01 Acres
  • $29,118 per Acre

  0 Split Rock Dr Unit KEY921291, Highland, NY 12719

  Waterfront...NOT Kidding! Rare wooded waterfront parcel..privacy in nature with towering trees and tucked away within this secluded setting overlooking the water.. the perfect ingredients for your harmonious getaway upstate in the Catskills. Begin dreaming about your custom design home and everything you will be able to finally create. Minutes from Eldred, Barryville, the Delaware river and

  Debbie Jagel Cabins & Canoes Real Estate

  0 Split Rock Dr Unit KEY921291, Highland, NY 12719
• 

  $564,000

  Sold Jun 16, 2026

  4 Cusa Dr, Highland, NY 12528

  • 3 Beds
  • 3 Baths
  • 2,040 Sq Ft
  • Built 1984

  Last Sold Summary

  • 7% Above List Price
  • $276/SF
  • 64 Days On Market

  Current Estimated Value $526,716

  Last Listing Agent Sandra Spector Howard Hanna Rand Realty

  4 Cusa Dr, Highland, NY 12528
• 

  Est $843,012

  Not Listed For Sale

  326 Perkinsville Rd, Highland, NY 12528

  • 3 Beds
  • 4 Baths
  • 3,275 Sq Ft
  • Built 2004

  326 Perkinsville Rd, Highland, NY 12528

  Last Sold Summary

  • 340 Days On Market
• 

  

  /13

  $49,999

  Pending

  • Land
  • 5 Acres
  • $10,000 per Acre

  0 Summit Dr Unit KEY842137, Highland, NY 12732

  Located in the exclusive gated community of Timber Lake Estates, this stunning 5-acre corner lot offers the perfect blend of privacy and natural beauty. Well-wooded and serene, the property boasts frontage on both Summit Drive and a quiet cul-de-sac on Deer Brook Drive, providing multiple access points and endless possibilities for a dream home or weekend retreat. Residents enjoy private access

  Kevin Fortuna K. Fortuna Realty, Inc.

  0 Summit Dr Unit KEY842137, Highland, NY 12732
• 

  $340,000

  Sold May 28, 2026

  396 Crescent Ave, Highland, NY 12528

  • 2 Beds
  • 1 Bath
  • 1,073 Sq Ft
  • Built 1962

  Last Sold Summary

  • 14% Above List Price
  • $317/SF
  • 47 Days On Market

  Current Estimated Value $314,870

  Last Listing Agent Patricia Sassi RE/MAX Benchmark Realty Group

  396 Crescent Ave, Highland, NY 12528
• 

  

  /49

  Est $624,211

  Not Listed For Sale

  30 Grand St, Highland, NY 12528

  • 3 Beds
  • 3.5 Baths
  • 2,658 Sq Ft
  • Built 1900

  30 Grand St, Highland, NY 12528

  Last Sold Summary

  • 18 Days On Market
• 

  

  /37

  $539,900

  $60K PRICE DROP Pending

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

  194 Vineyard Ave, Highland, NY 12528

  Custom built by the original owner. Featuring a bright and functional layout, the home is filled with abundant natural light and gleaming hardwood floors. Radiant heat throughout. The eat-in kitchen boasts warm cherry wood cabinets and granite countertops. The primary bedroom features cathedral ceilings, adding an airy and spacious feel. The attached oversized garage also provides ample storage.

  Angela Briante Briante Realty Group, LLC

  194 Vineyard Ave, Highland, NY 12528
• 

  

  /20

  $350,000

  Sold Apr 30, 2026

  15 Troy Ln, Highland, NY 12528

  • 2 Beds
  • 1.5 Baths
  • 1,302 Sq Ft
  • Built 1997

  Last Sold Summary

  • $269/SF
  • 28 Days On Market

  Current Estimated Value $349,227

  Last Listing Agent Dawn Passante Coldwell Banker Village GreenN

  15 Troy Ln, Highland, NY 12528
• 

  

  /36

  Est $378,111

  Not Listed For Sale

  10 Lauretta Dr, Highland, NY 12528

  • 3 Beds
  • 2 Baths
  • 1,125 Sq Ft
  • Built 1966

  10 Lauretta Dr, Highland, NY 12528

  Last Sold Summary

  • 29 Days On Market
• 

  

  /14

  $399,000

  • Land
  • 7.47 Acres
  • $53,414 per Acre

  0 York Lake Estates Rd Unit KEY987214, Highland, NY 12719

  Gorgeous lakefront property with possible owner financing! Build your dream waterfront retreat. This rare, southern-exposure lakefront property offers the ultimate canvas for your dream home, tucked within a private gated community. Spanning over 7.47 extraordinary acres along the shores of a pristine glacial lake, this secluded retreat is designed for those who value privacy, nature, and

  Dawn Payne Payne Team LLC

  0 York Lake Estates Rd Unit KEY987214, Highland, NY 12719
• 

  $325,000

  Sold Oct 30, 2025

  422 Gregory Ct Unit 307, Highland, NY 12528

  • 2 Beds
  • 2 Baths
  • 1,027 Sq Ft
  • Built 1991

  Last Sold Summary

  • 3% Above List Price
  • $316/SF
  • 21 Days On Market

  Current Estimated Value $333,657

  Last Listing Agent Nancy Diehl Rita Levine Real Estate

  422 Gregory Ct Unit 307, Highland, NY 12528
• 

  Est $565,039

  Not Listed For Sale

  25 Lauretta Dr, Highland, NY 12528

  • 4 Beds
  • 2.5 Baths
  • 2,470 Sq Ft
  • Built 1968

  25 Lauretta Dr, Highland, NY 12528

  Last Sold Summary

  • 33 Days On Market
• 

  

  /21

  $355,000

  Pending

  • 2 Beds
  • 1 Bath
  • 1,234 Sq Ft

  128 Vineyard Ave Unit 110, Highland, NY 12528

  Welcome to Highbridge Crossing, a modern river-town condominium building with direct access to the Hudson Valley Rail Trail in the heart of Highland, N.Y. This 1,234-square-foot first-floor residence blends smart design, comfort and easy outdoor living--ideal for low-maintenance living without sacrificing style. The open-concept layout features large windows and seamless flow throughout. The

  Andrea Babcock Onyx Property Management LLC

  128 Vineyard Ave Unit 110, Highland, NY 12528
• 

  $580,000

  Sold Jan 15, 2026

  5 Willow Dock Rd, Highland, NY 12528

  • 2 Beds
  • 2.5 Baths
  • 1,364 Sq Ft
  • Built 1860

  Last Sold Summary

  • 3% Below List Price
  • $425/SF
  • 28 Days On Market

  Current Estimated Value $590,261

  Last Listing Agent Lindsay Rothman Compass Greater NY LLC

  5 Willow Dock Rd, Highland, NY 12528
• 

  

  /26

  Est $630,332

  Not Listed For Sale

  21 Spring Meadow Ct, Highland, NY 12528

  • 4 Beds
  • 2.5 Baths
  • 2,400 Sq Ft
  • Built 2007

  21 Spring Meadow Ct, Highland, NY 12528

  Last Sold Summary

  • 30 Days On Market
• 

  

  /10

  $300,000

  • 4 Beds
  • 2 Baths
  • 1,450 Sq Ft

  87 Vineyard Ave, Highland, NY 12528

  Village of Highland two family w/two bedroom units. Hardwood floors throughout. Separate utilities with natural gas for heat & hot water. Centrally located with easy access to village amenities, commuter routes & Mid-Hudson Bridge. Attractively low taxes. Ideal for investor or owner occupant.

  Dan Axtmann BHHS Hudson Valley Properties

  87 Vineyard Ave, Highland, NY 12528
• 

  

  /35

  $510,000

  Sold Sep 16, 2025

  20-22 Milton Ave, Highland, NY 12528

  • 5 Beds
  • 5 Baths
  • 2,382 Sq Ft
  • Built 1890

  Last Sold Summary

  • 7% Below List Price
  • $214/SF
  • 69 Days On Market

  Last Listing Agent Hayes Clement Compass Greater New York, LLC

  20-22 Milton Ave, Highland, NY 12528
• 

  Est $487,715

  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
• 

  

  /13

  $254,999

  $10K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 730 Sq Ft

  128 Vineyard Ave Unit 207, Highland, NY 12528

  Welcome to Highbridge Crossing, a modern river-town condominium building with direct access to the Hudson Valley Rail Trail in the heart of Highland, N.Y. This 730-square-foot second-floor residence blends smart design, comfort and easy outdoor living--ideal for low-maintenance living without sacrificing style. The open-concept layout features large windows and seamless flow throughout. The

  Andrea Babcock Onyx Property Management LLC

  128 Vineyard Ave Unit 207, Highland, NY 12528
• 

  $450,000

  Sold Oct 16, 2025

  224 Martin Ave, Highland, NY 12528

  • 3 Beds
  • 1.5 Baths
  • 1,633 Sq Ft
  • Built 1940

  Last Sold Summary

  • 5% Below List Price
  • $276/SF
  • 87 Days On Market

  Current Estimated Value $473,479

  Last Listing Agent Dawn Passante Coldwell Banker Village Green

  224 Martin Ave, Highland, NY 12528
• 

  

  /11

  Est $445,483

  Not Listed For Sale

  269 Tuckers Corners Rd, Highland, NY 12528

  • 3 Beds
  • 1 Bath
  • 1,420 Sq Ft
  • Built 1973

  269 Tuckers Corners Rd, Highland, NY 12528

  Last Sold Summary

  • 12 Days On Market
• 

  

  /3

  $4,400,000

  • Land
  • 73.7 Acres
  • $59,701 per Acre

  00 Vineyard Ave, Highland, NY 12528

  Multi family property consisting of R-1/4, R-1/2 and R-1 zoning. Totaling 73 plus acres with two access points along Rte 44, Vineyard Avenue, in the Town of Lloyd, Ulster County, NY. One on the South end of the property with 150 feet of frontage along Vineyard Avenue and one on the North end of the property with 50 feet of frontage along Vineyard Avenue. Property slopes gently upward from road

  Robert Vitanza Rand Commercial

  00 Vineyard Ave, Highland, NY 12528
• 

  

  /6

  $105,000

  Sold Mar 16, 2026

  Tbd Smith Terrace, Highland, NY 12528

  • Land
  • 29,620 Sq Ft
  • $154,412 per Acre

  Last Sold Summary

  • 6% Above List Price
  • 21 Days On Market

  Last Listing Agent Dawn Passante Coldwell Banker Village GreenN

  Tbd Smith Terrace, Highland, NY 12528
• 

  Est $549,297

  Not Listed For Sale

  41 Jenkins Ln, Highland, NY 12528

  • 3 Beds
  • 3 Baths
  • 1,928 Sq Ft
  • Built 2003

  41 Jenkins Ln, Highland, NY 12528

  Last Sold Summary

  • 53 Days On Market
• 

  

  /24

  $179,000

  Pending Pre-Foreclosure

  • 4 Beds
  • 1.5 Baths
  • 1,404 Sq Ft

  687 Whitley Ln, Highland, NY 12528

  Investor opportunity in the Town of Lloyd! Situated on 1.4 private acres, this 4-bedroom home offers tremendous potential for renovation, customization, or resale. The property is in need of significant rehabilitation and is ready for its next owner to bring it back to life. Features include a full basement, attached garage, and a desirable location just minutes from New Paltz, the Mid-Hudson

  Philip Szumlaski Keller Williams Realty

  687 Whitley Ln, Highland, NY 12528
• 

  

  /32

  $450,000

  Sold May 04, 2026

  668 U S 44, Highland, NY 12528

  • 4 Beds
  • 1.5 Baths
  • 3,140 Sq Ft
  • Built 1920

  Last Sold Summary

  • $143/SF
  • 67 Days On Market

  Last Listing Agent Heather Hughes Hudson Dwellings Realty

  668 U S 44, Highland, NY 12528
• 

  

  /28

  Est $288,138

  Not Listed For Sale

  355 Crescent Ave, Highland, NY 12528

  • 2 Beds
  • 1 Bath
  • 895 Sq Ft
  • Built 1875

  355 Crescent Ave, Highland, NY 12528

  Last Sold Summary

  • 7 Days On Market
• 

  

  /13

  $254,999

  $10K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 730 Sq Ft

  128 Vineyard Ave Unit 208, Highland, NY 12528

  Welcome to Highbridge Crossing, a modern river-town condominium building with direct access to the Hudson Valley Rail Trail in the heart of Highland, N.Y. This 730-square-foot second-floor residence blends smart design, comfort and easy outdoor living--ideal for low-maintenance living without sacrificing style. The open-concept layout features large windows and seamless flow throughout. The

  Andrea Babcock Onyx Property Management LLC

  128 Vineyard Ave Unit 208, Highland, NY 12528
• 

  $299,000

  Sold Mar 24, 2026

  8 Sunny Brook Cir, Highland, NY 12528

  • 2 Beds
  • 1.5 Baths
  • 1,120 Sq Ft
  • Built 1974

  Last Sold Summary

  • $267/SF
  • 128 Days On Market

  Current Estimated Value $300,342

  Last Listing Agent Dan Axtmann BHHS Hudson Valley Properties

  8 Sunny Brook Cir, Highland, NY 12528
• 

  

  /25

  Est $743,851

  Not Listed For Sale

  11 Palazzo Ln, Highland, NY 12528

  • 5 Beds
  • 3.5 Baths
  • 2,880 Sq Ft
  • Built 1991

  11 Palazzo Ln, Highland, NY 12528

  Last Sold Summary

  • 11 Days On Market
• 

  

  /45

  $725,000

  • 4 Beds
  • 2.5 Baths
  • 3,100 Sq Ft

  14 Glen Rock Cir, Highland, NY 12528

  Elegant Contemporary Colonial tucked away on 5 beautifully landscaped private acres offers the perfect blend of comfort, space, and privacy. A dramatic two-story entry welcomes you into a thoughtfully designed home, perfect for both everyday living and entertaining. The formal dining room flows into a spacious kitchen featuring granite countertops, a center island, and an open layout to the

  Toni Petfield Century 21 Alliance Rlty Group

  14 Glen Rock Cir, Highland, NY 12528
• 

  

  /10

  $135,000

  Sold Dec 09, 2025

  251 Fosler Rd, Highland, NY 12528

  • Land
  • 12.9 Acres
  • $10,465 per Acre

  Last Sold Summary

  • 10% Below List Price
  • 24 Days On Market

  Current Estimated Value $135,347

  Last Listing Agent Michelle England Howard Hanna Rand Realty

  251 Fosler Rd, Highland, NY 12528
• 

  Est $445,144

  Not Listed For Sale

  683 State Route 44 55, Highland, NY 12528

  • 3 Beds
  • 2 Baths
  • 1,982 Sq Ft
  • Built 1966

  683 State Route 44 55, Highland, NY 12528

  Last Sold Summary

  • 73 Days On Market

Showing Results 81 - 120, Page 3 of 18