Highland, NY Homes

• 

  

  

  /12

  $279,000

  • 2 Beds
  • 1 Bath
  • 1,056 Sq Ft

  76 Sunny Brook Cir, Highland, NY 12528

  ATTENTION INVESTORS, CONTRACTORS, OR SOMEONE LOOKING FOR A RENOVATION PROJECT!!! This townhouse is ready for renovations, being sold as a shell, Freshly painted, New windows, New siding, recessed lightening, New electric switches and outlets with USB plugs. This unit is a legal 2 bedroom, with potential for a 3rd bedroom, office or guest room. This unit needs flooring, kitchen and bathroom. This

  Nancy Young BHHS Hudson Valley Properties

  76 Sunny Brook Cir, Highland, NY 12528
• 

  $386,000

  Sold Nov 07, 2025

  2 Cambridge Ct, Highland, NY 12528

  • 3 Beds
  • 2.5 Baths
  • 1,808 Sq Ft
  • Built 1989

  Last Sold Summary

  • 7% Above List Price
  • $213/SF
  • 25 Days On Market

  Current Estimated Value $419,687

  Last Listing Agent Christopher Baker River to Ridge Rlty Associates

  2 Cambridge Ct, Highland, NY 12528
• 

  

  

  /28

  Est $442,518

  Not Listed For Sale

  210 Plutarch Rd, Highland, NY 12528

  • 2 Beds
  • 1 Bath
  • 777 Sq Ft
  • Built 1940

  210 Plutarch Rd, Highland, NY 12528

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Meryl Fradin-Kalus BHHS HUDSON VALLEY PROP-NP
• 

  

  

  /7

  $180,000

  • Land
  • 6.29 Acres
  • $28,617 per Acre

  0 Split Rock Dr Unit KEY921280, Highland, NY 12719

  WATERFRONT!!!! Yes it is...with the views and sounds of the water and most of all serenity....Wooded, peaceful and awaiting you!! lots with mossy ground, sculptural boulders, and gentle contours create a magical setting for your future home site. Your house can sit perfectly tucked among the trees, offering a natural sense of utmost privacy. The subtle land contours are well suited for a walkout

  Debbie Jagel Cabins & Canoes Real Estate

  0 Split Rock Dr Unit KEY921280, Highland, NY 12719
• 

  $265,000

  Sold Aug 11, 2026

  128 Vineyard Ave Unit 106, Highland, NY 12528

  • 1 Bed
  • 1 Bath
  • 803 Sq Ft
  • Built 2019

  Last Sold Summary

  • 2% Below List Price
  • $330/SF
  • 77 Days On Market

  Last Listing Agent Andrea Babcock Onyx Property Management LLC

  128 Vineyard Ave Unit 106, Highland, NY 12528
• 

  Est $414,198

  Not Listed For Sale

  24 Amato Ln, Highland, NY 12528

  • 3 Beds
  • 3 Baths
  • 1,537 Sq Ft
  • Built 1942

  24 Amato Ln, Highland, NY 12528

  Last Sold Summary

  • 140 Days On Market

  Last Listing Agent Maria Murphy Keller Williams Realty
• 

  

  /23

  $1,250,000

  • Land
  • 4.7 Acres
  • $265,957 per Acre

  134 Bellevue Rd, Highland, NY 12528

  Spanning an expansive 4.7 acres, 134 Bellevue Road offers a rare opportunity to experience nature and simple indulgence high above the Hudson. This breathtaking, natural setting perfectly blends sweeping river vistas with immediate access to nearby rail lines and world-class outdoor adventure.Recently cleared to showcase its striking natural contours, the property offers a distinct "clean-site"

  Dominick Martorana Century 21 Alliance Rlty Group

  134 Bellevue Rd, Highland, NY 12528
• 

  $350,000

  Sold May 15, 2026

  29 Oakes Rd, Highland, NY 12528

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1840

  Last Sold Summary

  • 12% Below List Price
  • $331/SF
  • 191 Days On Market

  Current Estimated Value $358,132

  Last Listing Agent Anthony DeGelormo Century 21 Alliance Rlty Group

  29 Oakes Rd, Highland, NY 12528
• 

  Est $520,095

  Not Listed For Sale

  228 Plutarch Rd, Highland, NY 12528

  • 3 Beds
  • 2 Baths
  • 1,753 Sq Ft
  • Built 1946

  228 Plutarch Rd, Highland, NY 12528

  Last Sold Summary

  • 88 Days On Market

  Last Listing Agent Dawn Passante Coldwell Banker Village Green
• 

  /2

  $44,900

  Pending

  • Land
  • 5.7 Acres
  • $7,877 per Acre

  0 Split Rock Dr Unit PWBPW240517, Highland, NY 12719

  Escape to your own private oasis on 5+ acres of breathtaking woodland in the charming community of Barryville. This buildable lot presents the perfect opportunity to craft your dream home amidst a picturesque setting.This exceptional property is ideal for nature lovers, outdoor enthusiasts, and anyone seeking a peaceful escape from the ordinary. Start your next chapter surrounded by the majestic

  Diane Butler Diane C Butler Real Estate

  0 Split Rock Dr Unit PWBPW240517, Highland, NY 12719
• 

  $425,000

  Sold Nov 17, 2025

  59 South St, Highland, NY 12528

  • 2 Beds
  • 1 Bath
  • 1,365 Sq Ft
  • Built 1900

  Last Sold Summary

  • $311/SF
  • 105 Days On Market

  Current Estimated Value $463,906

  Last Listing Agent jeff farnell John J Lease REALTORS Inc

  59 South St, Highland, NY 12528
• 

  Est $671,881

  Not Listed For Sale

  353 Plutarch Rd, Highland, NY 12528

  • 3 Beds
  • 2.5 Baths
  • 2,277 Sq Ft
  • Built 1996

  353 Plutarch Rd, Highland, NY 12528

  Last Sold Summary

  • 26 Days On Market

  Last Listing Agent EILEEN FESKO BHHS Hudson Valley Properties
• 

  

  /50

  $649,900

  • 4 Beds
  • 3.5 Baths
  • 2,627 Sq Ft

  14 Lisa Dr, Highland, NY 12528

  Set on 1.6 picturesque acres in a quiet Highland cul-de-sac, this sprawling contemporary ranch offers an exceptional combination of space, privacy, and resort-style outdoor living. Surrounded by mature landscaping and natural beauty, the property features generous living spaces, multiple bedrooms, and an inviting backyard oasis designed for both relaxing and entertaining. The main level features

  Jennifer Gold RE/MAX Benchmark Realty Group

  14 Lisa Dr, Highland, NY 12528
• 

  $129,000

  Sold Jan 07, 2026

  69 North Rd, Highland, NY 12528

  • 2 Beds
  • 1 Bath
  • 1,225 Sq Ft
  • Built 1920

  Last Sold Summary

  • $105/SF
  • 74 Days On Market

  Current Estimated Value $180,655

  Last Listing Agent Kathy Dawson Howard Hanna Rand Realty

  69 North Rd, Highland, NY 12528
• 

  

  /23

  Est $704,202

  Not Listed For Sale

  368 Plutarch Rd, Highland, NY 12528

  • 3 Beds
  • 2.5 Baths
  • 1,754 Sq Ft
  • Built 1998

  368 Plutarch Rd, Highland, NY 12528

  Last Sold Summary

  • 25 Days On Market

  Last Listing Agent Helen Coyle Bergstein Past Member
• 

  

  /15

  $329,999

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

  107 Vista Dr, Highland, NY 12528

  Location, lifestyle, and effortless living come together in this beautifully reimagined, completely remodeled home. Ideally located just moments from the rail trail and within a short distance to town and its many amenities, this home offers the perfect blend of convenience and tranquility. Commuters will appreciate the easy access to Metro-North and New York City, while the quiet neighborhood

  Shelley Collins Hudson Dwellings Realty

  107 Vista Dr, Highland, NY 12528
• 

  $305,000

  Sold May 01, 2026

  791 Gregory Ct Unit 706, Highland, NY 12528

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

  Last Sold Summary

  • $322/SF
  • 16 Days On Market

  Current Estimated Value $303,431

  Last Listing Agent Barbara Carter Century 21 Alliance Rlty Group

  791 Gregory Ct Unit 706, Highland, NY 12528
• 

  

  /45

  Est $737,105

  Not Listed For Sale

  354 Plutarch Rd, Highland, NY 12528

  • 3 Beds
  • 2.5 Baths
  • 2,230 Sq Ft
  • Built 1997

  354 Plutarch Rd, Highland, NY 12528

  Last Sold Summary

  • 46 Days On Market

  Last Listing Agent Nicola Friedman Windsor Realty Services, Inc.
• 

  $510,900

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,800+ Sq Ft

  Adirondack Home Plan at Mountainside Woods, Highland, NY 12528

  Meadow Creek Development Builder

  2 Benjamin Dr Unit 42035422, Highland, NY 12528
• 

  $355,000

  Sold Oct 10, 2025

  785 South St, Highland, NY 12528

  • 3 Beds
  • 6 Baths
  • 2,444 Sq Ft
  • Built 2000

  Last Sold Summary

  • 3% Above List Price
  • $145/SF
  • 74 Days On Market

  Current Estimated Value $424,980

  Last Listing Agent Brenda Watington W Manor LLC

  785 South St, Highland, NY 12528
• 

  Est $448,328

  Not Listed For Sale

  465 Plutarch Rd, Highland, NY 12528

  • 4 Beds
  • 2 Baths
  • 1,588 Sq Ft
  • Built 1950

  465 Plutarch Rd, Highland, NY 12528

  Last Sold Summary

  • 16 Days On Market

  Last Listing Agent Rebecca Kaufman Q Home Sales
• 

  

  /45

  $299,999

  • 3 Beds
  • 1 Bath
  • 1,250 Sq Ft

  71 North Rd, Highland, NY 12528

  Vintage Hudson Valley charm, original character, and plenty of potential come together at 71 North Road in Highland. This inviting 3-bedroom, 1-bath home is filled with the details that give an older home its warmth and personality—from beautiful original woodwork and trim to hardwood floors, classic French doors, and original wood siding.A sweet covered front porch welcomes you home and

  Hilary Ryan Goldman Howard Hanna Rand Realty

  71 North Rd, Highland, NY 12528
• 

  $404,000

  Sold Sep 02, 2026

  60 Mayer Dr, Highland, NY 12528

  • 3 Beds
  • 2 Baths
  • 2,100 Sq Ft
  • Built 1964

  Last Sold Summary

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

  Current Estimated Value $412,784

  Last Listing Agent Nicholas Cuomo Keller Williams Realty

  60 Mayer Dr, Highland, NY 12528
• 

  

  /35

  Est $476,104

  Not Listed For Sale

  618 Plutarch Rd, Highland, NY 12528

  • 4 Beds
  • 2 Baths
  • 1,900 Sq Ft
  • Built 1980

  618 Plutarch Rd, Highland, NY 12528

  Last Sold Summary

  • 176 Days On Market

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

  

  /17

  $370,000

  Pending

  • 4 Beds
  • 2 Baths

  81 Kisor Rd, Highland, NY 12528

  Welcome to 81 Kisor Rd in the heart of Highland, NY — a strong investment opportunity featuring two occupied rental units with leases secured through April 2027, offering immediate and stable income for the next owner, while also presenting excellent future potential for an owner-occupier once the current leases expire.This two-family property consists of a spacious 3-bedroom apartment on the

  Dan Gilbert Brick and Mortar RE LLC

  81 Kisor Rd, Highland, NY 12528
• 

  

  /25

  $425,000

  Sold Aug 11, 2026

  3 Wilcox Ave, Highland, NY 12528

  • 3 Beds
  • 2 Baths
  • 1,582 Sq Ft
  • Built 1948

  Last Sold Summary

  • 2% Above List Price
  • $269/SF
  • 27 Days On Market

  Current Estimated Value $415,522

  Last Listing Agent Christopher Baker River To Ridge Realty Associat

  3 Wilcox Ave, Highland, NY 12528
• 

  

  /32

  Est $645,455

  Not Listed For Sale

  608 Plutarch Rd, Highland, NY 12528

  • 4 Beds
  • 2.5 Baths
  • 2,820 Sq Ft
  • Built 1972

  608 Plutarch Rd, Highland, NY 12528

  Last Sold Summary

  • 5 Days On Market

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

  

  /35

  $344,900

  Under Contract

  • Land
  • 58 Acres
  • $5,947 per Acre

  TBD Bellevue Rd, Highland, NY 12528

  Just shy of 60 acres of raw land only a stone's throw from the mighty Hudson River. Nearly 1,500' of road frontage with several building sites. This lot flows up onto a ridge with great views to the east. Endless acres to hike and explore with plenty of room for miles of trails. Rolling terrain with numerous rock outcroppings, some 40-50' tall. Mature hardwood forest worthy of a selective

  Bruce Stalnaker Coldwell Banker Village GreenN

  TBD Bellevue Rd, Highland, NY 12528
• 

  $319,000

  Sold Nov 12, 2025

  38 Sunny Brook Cir, Highland, NY 12528

  • 3 Beds
  • 1.5 Baths
  • 1,220 Sq Ft
  • Built 1976

  Last Sold Summary

  • $261/SF
  • 45 Days On Market

  Current Estimated Value $347,829

  Last Listing Agent Naomi Streicher Q Home Sales

  38 Sunny Brook Cir, Highland, NY 12528
• 

  

  /27

  Est $322,971

  Not Listed For Sale

  137 Baileys Gap Rd, Highland, NY 12528

  • 2 Beds
  • 1 Bath
  • 1,256 Sq Ft
  • Built 1954

  137 Baileys Gap Rd, Highland, NY 12528

  Last Sold Summary

  • 63 Days On Market

  Last Listing Agent Paige McClintock Howard Hanna Rand Realty
• 

  

  /22

  $199,000

  $50K PRICE DROP

  • Land
  • 6.38 Acres
  • $31,191 per Acre

  0 Browning Blvd Unit KEY997085, Highland, NY 12719

  Escape to this beauty lakefront property sitting on 6.38 gorgeous acres in the private gated community of York Lake Shores. Enjoy boating, sailing, swimming, and fishing on the pristine lake while surrounded by peace and nature. Ideally located just two hours from New York City and under 20 minutes to the Metro-North train, this property offers the perfect balance of seclusion and convenience.

  Dawn Payne Payne Team LLC

  0 Browning Blvd Unit KEY997085, Highland, NY 12719
• 

  $585,000

  Sold Jun 22, 2026

  410 Vineyard Ave, Highland, NY 12528

  • 4 Beds
  • 3 Baths
  • 2,268 Sq Ft
  • Built 1973

  Last Sold Summary

  • 5% Below List Price
  • $258/SF
  • 49 Days On Market

  Current Estimated Value $596,055

  Last Listing Agent Kassia Connors eXp Realty

  410 Vineyard Ave, Highland, NY 12528
• 

  /2

  Est $710,160

  Not Listed For Sale

  130 Macks Ln, Highland, NY 12528

  • 3 Beds
  • 3 Baths
  • 2,648 Sq Ft
  • Built 2003

  130 Macks Ln, Highland, NY 12528
• 

  

  /32

  $625,000

  $25K PRICE DROP Pending

  • 3 Beds
  • 2 Baths
  • 1,609 Sq Ft

  321 Orchard Rd, Highland, NY 12528

  Set back on nearly two acres, this architecturally inspired ranch captures the best of mid-century design with a dramatic wall of windows, soaring beamed ceilings, a floor-to-ceiling stone fireplace, and seamless indoor-outdoor living centered around a large in-ground pool.Natural light pours through the expansive windows, giving the main living space an open, airy feel while framing

  Craig Smith Compass Greater NY, LLC

  321 Orchard Rd, Highland, NY 12528
• 

  

  /39

  $535,000

  Sold Aug 11, 2026

  85 Bellevue Rd, Highland, NY 12528

  • 3 Beds
  • 2 Baths
  • 1,862 Sq Ft
  • Built 1986

  Last Sold Summary

  • 7% Above List Price
  • $287/SF
  • 27 Days On Market

  Current Estimated Value $496,305

  Last Listing Agent Joseph Pettinella Century 21 Alliance-NP

  85 Bellevue Rd, Highland, NY 12528
• 

  

  /33

  Est $571,527

  Not Listed For Sale

  12 Blue Point Rd, Highland, NY 12528

  • 3 Beds
  • 3 Baths
  • 2,244 Sq Ft
  • Built 2007

  12 Blue Point Rd, Highland, NY 12528

  Last Sold Summary

  • 34 Days On Market

  Last Listing Agent Savannah Miceli Century 21 Alliance-NP
• 

  

  /6

  $179,000

  $20K PRICE DROP

  • Land
  • 11 Acres
  • $16,273 per Acre

  TBD Hawleys Corners Rd, Highland, NY 12528

  11 acres offering privacy and potential. The land is ideal for building a secluded estate or your own nature retreat. Located on a country road, yet close to Route 299 leading to the NYS Thruway. The Mid-Hudson Bridge is only 5 miles away. The parcels break down as follows: Parcel 1: 3.5 acres, Parcel 2: 4 acres, and Parcel 3: 3.7 acres. Key features include a peaceful rural setting with minimal

  Dawn Passante Coldwell Banker Village Green

  TBD Hawleys Corners Rd, Highland, NY 12528
• 

  $520,000

  Sold Jul 31, 2026

  21 Jenkins Ln, Highland, NY 12528

  • 4 Beds
  • 2.5 Baths
  • 2,260 Sq Ft
  • Built 2004

  Last Sold Summary

  • 4% Above List Price
  • $230/SF
  • 28 Days On Market

  Current Estimated Value $631,146

  Last Listing Agent Virginia Corbett eXp Realty

  21 Jenkins Ln, Highland, NY 12528
• 

  Est $427,678

  Not Listed For Sale

  4 Blue Point Rd, Highland, NY 12528

  • 2 Beds
  • 1.5 Baths
  • 1,321 Sq Ft
  • Built 1968

  4 Blue Point Rd, Highland, NY 12528

  Last Sold Summary

  • 113 Days On Market

  Last Listing Agent JoAnn Ellis Summerset Realty
• 

  

  /43

  $995,000

  • 2 Beds
  • 2 Baths
  • 1,575 Sq Ft

  83 Cotter Rd, Highland, NY 12528

  Tucked away at the end of a 1,700+ foot private driveway, this one-of-a-kind custom-built retreat offers the peace, privacy, and natural beauty you’ve been searching for. Situated on an incredible 63-acre parcel in the Town of Plattekill (Wallkill School District), this property is a rare opportunity for outdoor enthusiasts, hunters, weekend escape seekers, or anyone looking to enjoy a secluded

  Gary MacEntee Keller Williams Realty

  83 Cotter Rd, Highland, NY 12528

Showing Results 161 - 200, Page 5 of 18