Highland, NY Homes

• 

  Est $376,948

  Not Listed For Sale

  70 Argent Dr, Highland, NY 12528

  • 2 Beds
  • 1.5 Baths
  • 1,470 Sq Ft
  • Built 2003

  70 Argent Dr, Highland, NY 12528

  Last Sold Summary

  • 27 Days On Market
• 

  

  

  /40

  $499,000

  Pending

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

  21 Jenkins Ln, Highland, NY 12528

  Set on a one acre lot in Ulster County within the Highland School District, this 4-bedroom, 2.5-bath raised ranch offers approximately 2,260 square feet of living space designed for buyers looking for open layout flow, flexible interior rooms, and usable outdoor space. Built in 2004, the home brings together vaulted ceilings, a fireplace-centered living area, and a connected main level where the

  Virginia Corbett eXp Realty

  21 Jenkins Ln, Highland, NY 12528
• 

  $370,000

  Sold Mar 20, 2026

  22 Washington Ave, Highland, NY 12528

  • 4 Beds
  • 1.5 Baths
  • 1,458 Sq Ft
  • Built 1840

  Last Sold Summary

  • 7% Below List Price
  • $254/SF
  • 120 Days On Market

  Current Estimated Value $377,038

  Last Listing Agent CAROL MC RITCHIE Thomas Zengen

  22 Washington Ave, Highland, NY 12528
• 

  Est $375,325

  Not Listed For Sale

  9 Argent Dr, Highland, NY 12528

  • 2 Beds
  • 1.5 Baths
  • 1,464 Sq Ft
  • Built 2002

  9 Argent Dr, Highland, NY 12528

  Last Sold Summary

  • 17 Days On Market
• 

  

  

  /48

  $799,000

  • 4 Beds
  • 2.5 Baths
  • 2,502 Sq Ft

  27 Hawleys Corners Rd, Highland, NY 12528

  EXQUISITE HOME WITH AN OUTDOOR PRIVATE RETREAT-LIKE OASIS FEATURING A FREEFORM HEATED POOL! NEW PALTZ SCHOOLS! Set on 2.6 wooded acres, this stunning colonial is updated, freshly painted and truly move-in ready. Enjoy all the benefits of newer construction with the added advantage of a fully established backyard designed for effortless outdoor living. A charming TREX front deck overlooks a serene

  Maryann Pillitteri Rita Levine Real Estate

  27 Hawleys Corners Rd, Highland, NY 12528
• 

  

  /41

  $638,600

  Sold Jun 25, 2026

  31 Hawleys Corners Rd, Highland, NY 12528

  • 4 Beds
  • 1.5 Baths
  • 2,088 Sq Ft
  • Built 1965

  Last Sold Summary

  • 7% Above List Price
  • $306/SF
  • 28 Days On Market

  Current Estimated Value $602,572

  Last Listing Agent Jason Schobert eXp Realty

  31 Hawleys Corners Rd, Highland, NY 12528
• 

  Est $367,241

  Not Listed For Sale

  11 Argent Dr, Highland, NY 12528

  • 2 Beds
  • 1.5 Baths
  • 1,440 Sq Ft
  • Built 2002

  11 Argent Dr, Highland, NY 12528

  Last Sold Summary

  • 29 Days On Market
• 

  

  /28

  $625,000

  • 4 Beds
  • 3.5 Baths
  • 3,348 Sq Ft

  138 Half Moon Rd, Highland, NY 12528

  Welcome to 138 Half Moon Drive! Tucked away at the end of a long private driveway, this beautiful center hall Colonial is set on 8 acres of wooded privacy, offering space, comfort, and seclusion. This updated 4-bedroom home features 9-foot ceilings throughout the main level, a spacious kitchen, a warm and inviting family room with a fireplace, formal dining room, and a large great room that's

  Naomi Streicher Q Home Sales

  138 Half Moon Rd, Highland, NY 12528
• 

  $439,900

  Sold May 06, 2026

  13 Sharon Dr, Highland, NY 12528

  • 3 Beds
  • 1.5 Baths
  • 1,092 Sq Ft
  • Built 1983

  Last Sold Summary

  • 20% Below List Price
  • $403/SF
  • 308 Days On Market

  Current Estimated Value $424,042

  Last Listing Agent Drita Shala Howard Hanna Rand Realty

  13 Sharon Dr, Highland, NY 12528
• 

  

  /7

  Est $298,193

  Not Listed For Sale

  777 Gregory Ct, Highland, NY 12528

  • 2 Beds
  • 1 Bath
  • 946 Sq Ft
  • Built 2004

  777 Gregory Ct, Highland, NY 12528

  Last Sold Summary

  • 31 Days On Market
• 

  

  /31

  $279,900

  Pending Pre-Foreclosure

  • 3 Beds
  • 1 Bath
  • 1,288 Sq Ft

  7 Christopher Ave, Highland, NY 12528

  Nestled on a quiet side street in the historic hamlet of Highland, this cozy ranch offers comfortable single-level living in a prime Hudson Valley location. The home features three bedrooms and a spacious living room highlighted by a brick wood-burning fireplace with direct access to the backyard for easy indoor-outdoor flow. An oversized sun porch filled with natural light, creating a

  Melinda White Keller Williams Realty

  7 Christopher Ave, Highland, NY 12528
• 

  

  /42

  $460,000

  Sold May 21, 2026

  38 Roxanne Blvd, Highland, NY 12528

  • 3 Beds
  • 2.5 Baths
  • 1,707 Sq Ft
  • Built 1986

  Last Sold Summary

  • 2% Below List Price
  • $269/SF
  • 52 Days On Market

  Current Estimated Value $471,032

  Last Listing Agent Amy Hawks Berardi Realty

  38 Roxanne Blvd, Highland, NY 12528
• 

  Est $291,876

  Not Listed For Sale

  769 Gregory Ct, Highland, NY 12528

  • 2 Beds
  • 1 Bath
  • 946 Sq Ft
  • Built 2004

  769 Gregory Ct, Highland, NY 12528

  Last Sold Summary

  • 33 Days On Market
• 

  

  /24

  $530,900

  • 3 Beds
  • 3 Baths
  • 2,050 Sq Ft

  452 Vineyard Ave, Highland, NY 12528

  This home is completely remodeled. New roof, new siding new windows new Insulation all new electrical all new plumbing. All new flooring throughout the home. Brand new kitchen with quartz countertops, completely remodeled bathrooms. Brand new central air unit brand new furnace ,brand new hot water heater. This Home is just minutes away from the mid Hudson Bridge and the Minnewaska mountains.

  Derek Greene Greene Realty Group

  452 Vineyard Ave, Highland, NY 12528
• 

  $222,000

  Sold Nov 24, 2025

  534 New Paltz Rd, Highland, NY 12528

  • 1 Bed
  • 1 Bath
  • 762 Sq Ft
  • Built 1960

  Last Sold Summary

  • 1% Below List Price
  • $291/SF
  • 56 Days On Market

  Current Estimated Value $236,019

  Last Listing Agent Jonathan Minerick HomeCoin.com

  534 New Paltz Rd, Highland, NY 12528
• 

  Est $297,992

  Not Listed For Sale

  555 Gregory Ct Unit 603, Highland, NY 12528

  • 2 Beds
  • 1 Bath
  • 946 Sq Ft
  • Built 2004

  555 Gregory Ct Unit 603, Highland, NY 12528

  Last Sold Summary

  • 29 Days On Market
• 

  

  /13

  $254,999

  $10K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 730 Sq Ft

  128 Vineyard Ave Unit 205, 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 205, Highland, NY 12528
• 

  $960,000

  Sold Mar 26, 2026

  10-32 S Roberts Rd, Highland, NY 12528

  • 10 Baths
  • 8,985 Sq Ft
  • Built 1900

  Last Sold Summary

  • 1% Above List Price
  • $107/SF
  • 60 Days On Market

  Last Listing Agent Diane Mi Ryoung Chong HANMI REALTY

  10-32 S Roberts Rd, Highland, NY 12528
• 

  

  /16

  Est $306,404

  Not Listed For Sale

  337 Gregory Ct, Highland, NY 12528

  • 2 Beds
  • 1 Bath
  • 949 Sq Ft
  • Built 2004

  337 Gregory Ct, Highland, NY 12528

  Last Sold Summary

  • 7 Days On Market
• 

  

  /42

  $499,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,862 Sq Ft

  85 Bellevue Rd, Highland, NY 12528

  Nestled on a quiet road in the heart of the Hudson Valley, this well maintained raised ranch at 85 Bellevue Road in Highland offers comfortable living with a spacious layout and peaceful surroundings. Built in 1987, the home features approximately 1,800+ square feet of living space with 3 bedrooms and 2 full bathrooms on over a half acre of property. The main level offers a bright and inviting

  Geraldine Gaudioso Century 21 Alliance Rlty Group

  85 Bellevue Rd, Highland, NY 12528
• 

  

  /44

  $900,000

  Sold Feb 17, 2026

  1 Janine Place, Highland, NY 12528

  • 4 Beds
  • 3 Baths
  • 2,600 Sq Ft
  • Built 2000

  Last Sold Summary

  • 6% Above List Price
  • $346/SF
  • 33 Days On Market

  Current Estimated Value $902,009

  Last Listing Agent Lindsay Stevens eXp Realty

  1 Janine Place, Highland, NY 12528
• 

  

  /27

  Est $304,963

  Not Listed For Sale

  434 Gregory Ct, Highland, NY 12528

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

  434 Gregory Ct, Highland, NY 12528

  Last Sold Summary

  • 38 Days On Market
• 

  

  /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

  Kristen Zigouras eXp Realty

  407 Swartekill Rd, Highland, NY 12528
• 

  $580,000

  Sold Sep 18, 2025

  17 Dogwood Knolls, Highland, NY 12528

  • 3 Beds
  • 2.5 Baths
  • 2,284 Sq Ft
  • Built 1989

  Last Sold Summary

  • 1% Above List Price
  • $254/SF
  • 58 Days On Market

  Current Estimated Value $580,672

  Last Listing Agent Gzim Hakanjin Coldwell Banker Realty

  17 Dogwood Knolls, Highland, NY 12528
• 

  Est $303,720

  Not Listed For Sale

  444 Gregory Ct, Highland, NY 12528

  • 2 Beds
  • 2 Baths
  • 1,027 Sq Ft
  • Built 1990

  444 Gregory Ct, Highland, NY 12528

  Last Sold Summary

  • 28 Days On Market
• 

  

  /32

  $485,000

  $114K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,510 Sq Ft

  340 Vineyard Ave, Highland, NY 12528

  Step back in time with this spacious Victorian home full of original charm and character. Nestled on 41.10 acres of scenic land with mountain views. This property features a detached barn, 2 car garage and a classic summer kitchen. This property offers endless potential for restoration or creative retreat spaces. Inside you will find hardwood floors, birch cabinets with amazing stainless retro

  Ronnie Rebis Grist Mill Real Estate

  340 Vineyard Ave, Highland, NY 12528
• 

  

  /43

  $510,000

  Sold Jul 13, 2026

  104 New Paltz Rd, Highland, NY 12528

  • 3 Beds
  • 2.5 Baths
  • 2,520 Sq Ft
  • Built 1967

  Last Sold Summary

  • 2% Above List Price
  • $202/SF
  • 29 Days On Market

  Current Estimated Value $500,752

  Last Listing Agent Dawn Passante Coldwell Banker Village GreenN

  104 New Paltz Rd, Highland, NY 12528
• 

  

  /16

  Est $302,039

  Not Listed For Sale

  428 Gregory Ct, Highland, NY 12528

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

  428 Gregory Ct, Highland, NY 12528

  Last Sold Summary

  • 28 Days On Market
• 

  

  /23

  $340,000

  Pending

  • 2 Beds
  • 1 Bath
  • 1,116 Sq Ft

  128 Vineyard Ave Unit 209, 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 1116-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 209, Highland, NY 12528
• 

  

  /60

  $550,000

  Sold May 06, 2026

  122 Vineyard Ave, Highland, NY 12528

  • 4 Beds
  • 2 Baths
  • 2,110 Sq Ft
  • Built 1900

  Last Sold Summary

  • 8% Below List Price
  • $261/SF
  • 30 Days On Market

  Current Estimated Value $557,214

  Last Listing Agent Maria Ferguson Hudson River Valley Properties

  122 Vineyard Ave, Highland, NY 12528
• 

  

  /22

  Est $265,552

  Not Listed For Sale

  204 Gregory Ct, Highland, NY 12528

  • 2 Beds
  • 1 Bath
  • 946 Sq Ft
  • Built 1990

  204 Gregory Ct, Highland, NY 12528

  Last Sold Summary

  • 29 Days On Market
• 

  

  /5

  $25,000

  • Land
  • 1.03 Acres
  • $24,272 per Acre

  0 Park Ln Unit KEY984771, Highland, NY 12792

  BUILDING LOT IN YULAN, NY - This is a cleared one acre parcel with the driveway and parking area installed. Electric is at the road and can easily be brought into the site. This little neighborhood is tucked away in the country with a ball field just down the road, makes this a special location for a new home. Approximately 2.5 hrs from NYC, makes this special property a very easy commute. Close

  Caroline Akt Caroline Akt Realty LLC

  0 Park Ln Unit KEY984771, Highland, NY 12792
• 

  $554,900

  Sold Aug 07, 2025

  9 Lisa Dr, Highland, NY 12528

  • 3 Beds
  • 2.5 Baths
  • 2,681 Sq Ft
  • Built 1973

  Last Sold Summary

  • 1% Below List Price
  • $207/SF
  • 47 Days On Market

  Current Estimated Value $584,369

  Last Listing Agent Salvatore Trapani Summerset Realty

  9 Lisa Dr, Highland, NY 12528
• 

  

  /8

  Est $265,997

  Not Listed For Sale

  202 Gregory Ct, Highland, NY 12528

  • 2 Beds
  • 1 Bath
  • 964 Sq Ft
  • Built 1990

  202 Gregory Ct, Highland, NY 12528

  Last Sold Summary

  • 10 Days On Market
• 

  

  /50

  $1,250,000

  • 14 Beds
  • 9 Baths
  • 6,406 Sq Ft

  346 Crescent Ave, Highland, NY 12528

  The Historic “Clintondale Elixir Spring House” A timeless treasure, the historic Clintondale Elixir Spring House—originally built in 1790—is a rare and remarkable offering to the market. Encompassing over 6,400 square feet of living space, this distinguished residence invites you to create your forever home amid rich character and architectural beauty. Step through the welcoming rocking-chair

  Artur Galustyan Century 21 Alliance Rlty Group

  346 Crescent Ave, Highland, NY 12528
• 

  $537,500

  Sold Sep 22, 2025

  27 Salk Dr, Highland, NY 12528

  • 4 Beds
  • 2.5 Baths
  • 2,342 Sq Ft
  • Built 2005

  Last Sold Summary

  • 7% Below List Price
  • $230/SF
  • 81 Days On Market

  Current Estimated Value $567,564

  Last Listing Agent Margaret Thorne KW MidHudson

  27 Salk Dr, Highland, NY 12528
• 

  Est $361,397

  Not Listed For Sale

  186 Sterling Place, Highland, NY 12528

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

  186 Sterling Place, Highland, NY 12528

  Last Sold Summary

  • 17 Days On Market
• 

  

  /40

  $450,000

  Under Contract

  • 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

  Kristen Zigouras eXp Realty

  573 Plutarch Rd, Highland, NY 12528
• 

  

  /24

  $350,000

  Sold Nov 20, 2025

  153 Upper Grand St, Highland, NY 12528

  • 4 Beds
  • 1 Bath
  • 1,524 Sq Ft
  • Built 1950

  Last Sold Summary

  • $230/SF
  • 93 Days On Market

  Current Estimated Value $375,917

  Last Listing Agent John Quinn Quinn Realty Group Inc.

  153 Upper Grand St, Highland, NY 12528
• 

  

  /32

  Est $336,465

  Not Listed For Sale

  162 Sterling Place, Highland, NY 12528

  • 2 Beds
  • 1.5 Baths
  • 1,175 Sq Ft
  • Built 1991

  162 Sterling Place, Highland, NY 12528

  Last Sold Summary

  • 171 Days On Market

Showing Results 201 - 240, Page 6 of 18