Highland, NY Homes

• 

  $450,000

  Sold Sep 04, 2026

  11 Sharon Dr, Highland, NY 12528

  • 3 Beds
  • 1.5 Baths
  • 1,092 Sq Ft
  • Built 1982

  Last Sold Summary

  • $412/SF
  • 22 Days On Market

  Current Estimated Value $439,946

  Last Listing Agent Neeta Gupta Redfin Real Estate

  11 Sharon Dr, Highland, NY 12528
• 

  Est $515,050

  Not Listed For Sale

  876 South St, Highland, NY 12528

  • 3 Beds
  • 1.5 Baths
  • 1,923 Sq Ft
  • Built 1780

  876 South St, Highland, NY 12528

  Last Sold Summary

  • 76 Days On Market

  Last Listing Agent Bethany Wager-Mckee Agnes I Wager Realty Inc.
• 

  

  

  /23

  $355,000

  Pending

  • 2 Beds
  • 1 Bath
  • 1,230 Sq Ft

  128 Vineyard Ave Unit 102, 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 1,230-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 102, Highland, NY 12528
• 

  $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 $557,686

  Last Listing Agent Sandra Spector Howard Hanna Rand Realty

  4 Cusa Dr, Highland, NY 12528
• 

  Est $317,036

  Not Listed For Sale

  117 Half Moon Rd, Highland, NY 12528

  • 4 Beds
  • 1 Bath
  • 1,414 Sq Ft
  • Built 1900

  117 Half Moon Rd, Highland, NY 12528

  Last Sold Summary

  • 69 Days On Market

  Last Listing Agent Nancy Senescu Bella NS Properties LLC
• 

  

  /65

  $998,500

  Open House 9/26 $102K PRICE DROP

  • 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
• 

  $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 $334,827

  Last Listing Agent Patricia Sassi RE/MAX Benchmark Realty Group

  396 Crescent Ave, Highland, NY 12528
• 

  Not Listed For Sale

  27 Vineyard Ave, Highland, NY 12528

  • 6 Beds
  • 4 Baths
  • 2,916 Sq Ft
  • Built 1900

  27 Vineyard Ave, Highland, NY 12528

  Last Sold Summary

  • 50 Days On Market

  Last Listing Agent Hamar Clarke Clarke Realty & Associates LLC
• 

  

  /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
• 

  

  /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 $354,042

  Last Listing Agent Dawn Passante Coldwell Banker Village GreenN

  15 Troy Ln, Highland, NY 12528
• 

  Not Listed For Sale

  50 John White Rd, Highland, NY 12528

  • 9 Beds
  • 5 Baths
  • 1,000 Sq Ft
  • Built 1992

  50 John White Rd, Highland, NY 12528

  Last Sold Summary

  • 144 Days On Market

  Last Listing Agent Anesha Nesbitt eXp Realty
• 

  

  /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
• 

  $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 $341,151

  Last Listing Agent Nancy Diehl Rita Levine Real Estate

  422 Gregory Ct Unit 307, Highland, NY 12528
• 

  

  /35

  Est $514,900

  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

  Last Listing Agent Stephanie Way Past Member
• 

  

  /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
• 

  $775,000

  Sold Aug 19, 2026

  241 Chapel Hill Rd, Highland, NY 12528

  • 4 Beds
  • 2 Baths
  • 2,506 Sq Ft
  • Built 1974

  Last Sold Summary

  • 19% Above List Price
  • $309/SF
  • 50 Days On Market

  Current Estimated Value $739,596

  Last Listing Agent Patricia Breen Compass Greater NY, LLC

  241 Chapel Hill Rd, Highland, NY 12528
• 

  

  /49

  Est $651,404

  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

  Last Listing Agent Donna Brooks Compass Greater New York, LLC
• 

  

  /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 and 150’ frontage.along the shores of a pristine glacial lake, this secluded retreat is designed for those who value privacy,

  Dawn Payne Payne Team LLC

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

  $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 $600,639

  Last Listing Agent Lindsay Rothman Compass Greater NY LLC

  5 Willow Dock Rd, Highland, NY 12528
• 

  

  /36

  Est $371,999

  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

  Last Listing Agent Frank Tangredi Frank Tangredi Realty Company
• 

  

  /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
• 

  

  /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 $590,893

  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

  Last Listing Agent Leigh Wagner-Quintana KW Hudson Valley North
• 

  

  /35

  $375,000

  Open Sun 12PM - 3PM

  • 2 Beds
  • 2 Baths
  • 1,760 Sq Ft

  198 S Riverside Rd, Highland, NY 12528

  CASH ONLY! Brick Ranch! 1,760 sq. ft. 2 Bedroom, 2 Full Bath, Gleaming Hardwood Floors, Updated kitchen with Jenn Air Downdraft stove, European Cabinets, SS Appliances, Kitchen with Corian counter with stools & dinette eating area with ceramic tile floors and sliding door to 6 yr old huge cedar deck, large living room with hardwood floors & large Triple picture window. Full bath on 1st floor,

  Joanne Timperio RE/MAX Benchmark Realty Group

  198 S Riverside Rd, 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 $488,857

  Last Listing Agent Dawn Passante Coldwell Banker Village Green

  224 Martin Ave, Highland, NY 12528
• 

  

  /26

  Est $657,106

  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

  Last Listing Agent Jason Nadeau Compass Greater NY, LLC
• 

  

  /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
• 

  

  /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
• 

  

  /11

  Est $467,286

  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

  Last Listing Agent Jason Schobert eXp Realty
• 

  

  /46

  $525,000

  • 3 Beds
  • 3 Baths
  • 2,000 Sq Ft

  133 Bedell Ave, Highland, NY 12528

  Gorgeous 3 bedroom, 3 bath, Raised Ranch nestled away on nearly 2 acres of beautiful property found a quiet neighborhood. Large living room fills with natural light from the bay windows that highlights the new flooring throughout the main living areas. Eat-in kitchen is loaded with plenty of heavy duty cabinets and counterspace, center island with breakfast nook, and a cooktop capped with an

  Tremaine Selby Weichert Realtors

  133 Bedell Ave, 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
• 

  Est $557,918

  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

  Last Listing Agent William Bergin RE/MAX Benchmark Realty Group
• 

  

  /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
• 

  $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 $307,545

  Last Listing Agent Dan Axtmann BHHS Hudson Valley Properties

  8 Sunny Brook Cir, Highland, NY 12528
• 

  Est $933,976

  Not Listed For Sale

  740 State Route 44 55, Highland, NY 12528

  • 4 Beds
  • 2.5 Baths
  • 4,000 Sq Ft
  • Built 2004

  740 State Route 44 55, Highland, NY 12528

  Last Sold Summary

  • 51 Days On Market

  Last Listing Agent Steve Moreau Tactical Realty LLC
• 

  

  /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
• 

  

  /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 $137,380

  Last Listing Agent Michelle England Howard Hanna Rand Realty

  251 Fosler Rd, Highland, NY 12528
• 

  

  /28

  Est $273,264

  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

  Last Listing Agent Dylan Taft Taft Street Realty, Inc.
• 

  

  /24

  $500,000

  • 3 Beds
  • 2 Baths
  • 2,086 Sq Ft

  269 Orchard Rd, Highland, NY 12528

  Nestled among scenic orchards is this beautiful, updated nineteenth century farm house situated on almost 20 acres of beautiful pasture land and woods. This charming 3 bedroom home has a lovely full bath and plenty of living space for both humans and horses alike. The current owner keeps her horses on the property which is equipped with 2 run-in sheds and 7 shed row stalls which all have power

  Daniel Balassone VYLLA Home

  269 Orchard Rd, Highland, NY 12528
• 

  

  /23

  $337,000

  Sold Nov 04, 2025

  365 Crescent Ave Unit 367, Highland, NY 12528

  • 3 Beds
  • 1 Bath
  • 1,372 Sq Ft
  • Built 1940

  Last Sold Summary

  • 2% Above List Price
  • $246/SF
  • 52 Days On Market

  Current Estimated Value $419,044

  Last Listing Agent Ronnie Rebis Grist Mill Real Estate

  365 Crescent Ave Unit 367, Highland, NY 12528

Showing Results 81 - 120, Page 3 of 18