Highland, NY Homes

• 

  

  

  /13

  $500,000

  $195K PRICE DROP

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

  TBD Rt 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 Rt 9w, 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 $403,709

  Last Listing Agent Ronnie Rebis Grist Mill Real Estate

  365 Crescent Ave Unit 367, Highland, NY 12528
• 

  

  

  /49

  Est $532,845

  Not Listed For Sale

  23 Blossom Grove Ct, Highland, NY 12528

  • 4 Beds
  • 2.5 Baths
  • 1,872 Sq Ft
  • Built 2001

  23 Blossom Grove Ct, Highland, NY 12528

  Last Sold Summary

  • 81 Days On Market
• 

  

  /2

  $29,000

  $4K PRICE DROP

  • Land
  • 34,412 Sq Ft
  • $36,709 per Acre

  0 Hartung Rd Unit H6242040, Highland, NY 12732

  Fantastic level lot. Minutes walk to Sand Beach. Close to lots of great local restaurants, Bethel Woods performing arts center and the Delaware river.

  Dawn Payne Payne Team LLC

  0 Hartung Rd Unit H6242040, Highland, NY 12732
• 

  $448,000

  Sold Mar 19, 2026

  334 Pancake Hollow Rd, Highland, NY 12528

  • 3 Beds
  • 2 Baths
  • 2,715 Sq Ft
  • Built 1880

  Last Sold Summary

  • 6% Below List Price
  • $165/SF
  • 130 Days On Market

  Current Estimated Value $443,914

  Last Listing Agent Leigh Wagner-Quintana KW Hudson Valley North

  334 Pancake Hollow Rd, Highland, NY 12528
• 

  Est $424,391

  Not Listed For Sale

  11 Blossom Grove Ct, Highland, NY 12528

  • 2 Beds
  • 2 Baths
  • 1,092 Sq Ft
  • Built 1994

  11 Blossom Grove Ct, Highland, NY 12528

  Last Sold Summary

  • 23 Days On Market
• 

  

  /5

  $59,000

  • Land
  • 6.06 Acres
  • $9,736 per Acre

  Lot 45 Split Rock Dr, Highland, NY 12719

  Escape to total privacy on this peaceful 6.06-acre parcel in a desirable private community. Surrounded by nature, with pond views, this secluded lot offers the perfect setting for your dream getaway or year-round retreat. Tucked away in the heart of the Catskills, you’ll enjoy unmatched tranquility with easy access to local hiking, lakes, and charming towns. Build your vision where serenity meets

  Dawn Payne Payne Team LLC

  Lot 45 Split Rock Dr, Highland, NY 12719
• 

  

  /42

  $451,000

  Sold Dec 30, 2025

  41 New Paltz Rd, Highland, NY 12528

  • 3 Beds
  • 2 Baths
  • 1,547 Sq Ft
  • Built 1949

  Last Sold Summary

  • 9% Above List Price
  • $292/SF
  • 26 Days On Market

  Current Estimated Value $462,249

  Last Listing Agent Leigh Wagner-Quintana Past Member

  41 New Paltz Rd, Highland, NY 12528
• 

  Est $340,199

  Not Listed For Sale

  835 South St, Highland, NY 12528

  • 2 Beds
  • 1 Bath
  • 918 Sq Ft
  • Built 1880

  835 South St, Highland, NY 12528

  Last Sold Summary

  • 100 Days On Market
• 

  

  /16

  $200,000

  • Land
  • 3.13 Acres
  • $63,837 per Acre

  TBD Loughran Ln, Highland, NY 12528

  Build your dream home in one of the Hudson Valley's most peaceful and scenic settings. This 3-acre parcel is Board of Health for a 4-bedroom residence and offers a rare combination of privacy, natural beauty, and convenience. Surrounded by mature trees and rolling mountain views, the property features a gently cleared building area nestled within a picturesque woodland landscape. Located on a

  Siobhan Fahy eXp Realty

  TBD Loughran Ln, Highland, NY 12528
• 

  

  /30

  $340,000

  Sold Aug 06, 2025

  26 Toc Dr, Highland, NY 12528

  • 4 Beds
  • 2 Baths
  • 1,368 Sq Ft
  • Built 1995

  Last Sold Summary

  • 23% Below List Price
  • $249/SF
  • 321 Days On Market

  Current Estimated Value $366,699

  Last Listing Agent Dawn Passante Coldwell Banker Village GreenN

  26 Toc Dr, Highland, NY 12528
• 

  Est $405,178

  Not Listed For Sale

  45 Cotter Rd, Highland, NY 12528

  • 3 Beds
  • 2.5 Baths
  • 1,956 Sq Ft
  • Built 1987

  45 Cotter Rd, Highland, NY 12528

  Last Sold Summary

  • 108 Days On Market
• 

  

  /34

  $485,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,635 Sq Ft

  284 Tuckers Corners Rd, Highland, NY 12528

  Welcome to comfortable country living in the heart of the Hudson Valley! Set on 3.6 picturesque acres in Highland, this inviting ranch-style home offers the perfect blend of space, comfort, and convenience.Inside, you'll find a spacious family room that serves as the heart of the home, providing plenty of room for gatherings, relaxation, and everyday living. A beautiful fireplace creates a

  Dawn Passante Coldwell Banker Village GreenN

  284 Tuckers Corners Rd, Highland, NY 12528
• 

  $300,000

  Sold Oct 21, 2025

  660 Gregory Ct Unit 410, Highland, NY 12528

  • 2 Beds
  • 1 Bath
  • 946 Sq Ft
  • Built 2003

  Last Sold Summary

  • 9% Above List Price
  • $317/SF
  • 62 Days On Market

  Current Estimated Value $311,891

  Last Listing Agent John Durso Keller Williams Realty Partner

  660 Gregory Ct Unit 410, Highland, NY 12528
• 

  Est $558,269

  Not Listed For Sale

  272 Fosler Rd, Highland, NY 12528

  • 4 Beds
  • 3 Baths
  • 2,197 Sq Ft
  • Built 2023

  272 Fosler Rd, Highland, NY 12528

  Last Sold Summary

  • 106 Days On Market
• 

  

  /27

  $450,000

  Pending

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

  11 Sharon Dr, Highland, NY 12528

  Welcome to 11 Sharon Drive, a beautifully maintained 3-bedroom, 1.5-bath home in the highly sought-after Heritage Estates neighborhood of Highland. Ideally located just minutes from schools, shopping, dining, major commuter routes, and approximately 5 miles from the train station, this home offers the perfect blend of comfort, convenience, and lifestyle.The spacious open-concept layout is

  Neeta Gupta Redfin Real Estate

  11 Sharon Dr, Highland, NY 12528
• 

  $460,000

  Sold Sep 09, 2025

  723 New Paltz Rd, Highland, NY 12528

  • 4 Beds
  • 2 Baths
  • 2,121 Sq Ft
  • Built 1970

  Last Sold Summary

  • 2% Above List Price
  • $217/SF
  • 31 Days On Market

  Current Estimated Value $477,534

  Last Listing Agent Christopher Baker River to Ridge Rlty Associates

  723 New Paltz Rd, Highland, NY 12528
• 

  

  /24

  Est $480,929

  Not Listed For Sale

  647 South St, Highland, NY 12528

  • 3 Beds
  • 1.5 Baths
  • 1,648 Sq Ft
  • Built 1973

  647 South St, Highland, NY 12528

  Last Sold Summary

  • 170 Days On Market
• 

  

  /38

  $825,000

  • 4 Beds
  • 2.5 Baths
  • 2,420 Sq Ft

  39 Loughran Ln, Highland, NY 12528

  Tucked away on 4.5 private acres along a quiet country road, this beautifully maintained ranch home offers the ease of single-level living surrounded by nature, gardens, and mature woodlands. Designed to maximize natural light, the home welcomes you with an airy, open floor plan, expansive windows, skylights, and warm hardwood floors throughout much of the living space. At the heart of the home

  Siobhan Fahy eXp Realty

  39 Loughran Ln, Highland, NY 12528
• 

  

  /14

  $308,500

  Sold Sep 30, 2025

  329 Gregory Ct Unit 509, Highland, NY 12528

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

  Last Sold Summary

  • $326/SF
  • 27 Days On Market

  Current Estimated Value $313,551

  Last Listing Agent Nancy Senescu Bella NS Properties LLC

  329 Gregory Ct Unit 509, Highland, NY 12528
• 

  Est $480,279

  Not Listed For Sale

  613 South St, Highland, NY 12528

  • 4 Beds
  • 2 Baths
  • 2,368 Sq Ft
  • Built 1968

  613 South St, Highland, NY 12528

  Last Sold Summary

  • 84 Days On Market
• 

  

  /35

  $650,000

  Pending

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

  241 Chapel Hill Rd, Highland, NY 12528

  AO, Five acres, a variety of fruit trees, a pool and scenery that genuinely makes you catch your breath. And it is yours every single day, not just when you manage to get away. Built in 1974 and recently renovated, this Colonial property offers a blend of classic charm and modern touches. The interior showcases a thoughtfully designed layout suited for everyday living. To the right of the

  Patricia Breen Compass Greater NY, LLC

  241 Chapel Hill Rd, Highland, NY 12528
• 

  

  /28

  $315,000

  Sold Dec 01, 2025

  39 Sunnybrook Cir, Highland, NY 12528

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

  Last Sold Summary

  • $258/SF
  • 22 Days On Market

  Current Estimated Value $328,207

  Last Listing Agent Dawn Passante Coldwell Banker Village GreenN

  39 Sunnybrook Cir, Highland, NY 12528
• 

  Est $384,796

  Not Listed For Sale

  596 Milton Turnpike, Highland, NY 12528

  • 4 Beds
  • 2 Baths
  • 1,944 Sq Ft
  • Built 1930

  596 Milton Turnpike, Highland, NY 12528

  Last Sold Summary

  • 41 Days On Market
• 

  

  /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
• 

  $388,000

  Sold Sep 19, 2025

  16 Orchard Ln, Highland, NY 12528

  • 2 Beds
  • 1 Bath
  • 1,090 Sq Ft
  • Built 1988

  Last Sold Summary

  • 3% Above List Price
  • $356/SF
  • 42 Days On Market

  Current Estimated Value $396,792

  Last Listing Agent Megan Krusen eXp Realty

  16 Orchard Ln, Highland, NY 12528
• 

  Est $379,511

  Not Listed For Sale

  721 Milton Turnpike, Highland, NY 12528

  • 4 Beds
  • 2 Baths
  • 2,535 Sq Ft
  • Built 1930

  721 Milton Turnpike, Highland, NY 12528

  Last Sold Summary

  • 8 Days On Market
• 

  

  /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
• 

  $320,000

  Sold Mar 03, 2026

  578 South St, Highland, NY 12528

  • 2 Beds
  • 1 Bath
  • 1,723 Sq Ft
  • Built 1930

  Last Sold Summary

  • 3% Below List Price
  • $186/SF
  • 166 Days On Market

  Current Estimated Value $325,520

  Last Listing Agent Michele Marina Atlantica East Associates LLC

  578 South St, Highland, NY 12528
• 

  Not Listed For Sale

  727 Milton Turnpike, Highland, NY 12528

  • 2 Beds
  • 1 Bath
  • 880 Sq Ft
  • Built 1945

  727 Milton Turnpike, Highland, NY 12528

  Last Sold Summary

  • 22 Days On Market
• 

  

  /31

  $475,000

  $24K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,352 Sq Ft

  517 Crescent Ave, Highland, NY 12528

  Welcome to easy, one-level living in this beautifully maintained ranch home, built in 2020 and set on 1.2 peaceful acres. Offering 2 bedrooms, 2 full bathrooms, and a dedicated home office, this property combines modern comfort with the tranquility of country living. Start your mornings on the inviting front porch, the perfect spot to enjoy a cup of coffee while taking in the serene surroundings.

  Anthony DeGelormo Century 21 Alliance Rlty Group

  517 Crescent Ave, Highland, NY 12528
• 

  $1,091,125

  Sold Mar 02, 2026

  243 Hawleys Corners Rd, Highland, NY 12528

  • 3 Beds
  • 2.5 Baths
  • 3,068 Sq Ft
  • Built 1999

  Last Sold Summary

  • 16% Below List Price
  • $356/SF
  • 107 Days On Market

  Current Estimated Value $1,096,260

  Last Listing Agent Melissa Pettinella Century 21 Alliance Realty Grp

  243 Hawleys Corners Rd, Highland, NY 12528
• 

  Est $480,482

  Not Listed For Sale

  120 Camp Sunset Rd, Highland, NY 12528

  • 3 Beds
  • 3 Baths
  • 1,960 Sq Ft
  • Built 2006

  120 Camp Sunset Rd, Highland, NY 12528

  Last Sold Summary

  • 54 Days On Market
• 

  

  /50

  $680,000

  Pending

  • 5 Beds
  • 4 Baths
  • 3,522 Sq Ft

  196 Vineyard Ave, Highland, NY 12528

  Spacious side-by-side DUPLEX at 196 Vineyard Avenue in Highland, NY, offering a rare combination of comfort, versatility, and a truly picturesque setting. One Unit is THREE bedrooms with 2 Baths and the other Unit is TWO bedrooms and 2 Baths. Huge Primary Bedroom in Unit A with a wall of closets! Each unit has a GARAGE, and a walkout basement, providing ample living space and flexibility for both

  Angela Briante Briante Realty Group, LLC

  196 Vineyard Ave, Highland, NY 12528
• 

  $156,750

  Sold Aug 29, 2025

  854 New Paltz Rd, Highland, NY 12528

  • 1 Bed
  • 1 Bath
  • 1,596 Sq Ft
  • Built 1900

  Last Sold Summary

  • 32% Below List Price
  • $98/SF
  • 167 Days On Market

  Current Estimated Value $301,500

  Last Listing Agent Brian Smith River Realty Services, Inc.

  854 New Paltz Rd, Highland, NY 12528
• 

  Est $239,864

  Not Listed For Sale

  30 Cotter Rd, Highland, NY 12528

  • 3 Beds
  • 2 Baths
  • 1,080 Sq Ft
  • Built 1940

  30 Cotter Rd, Highland, NY 12528

  Last Sold Summary

  • 223 Days On Market
• 

  /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
• 

  $100,000

  Sold Jun 01, 2026

  3550 Route 9w, Highland, NY 12528

  • Land
  • 16,117 Sq Ft
  • $270,270 per Acre

  Last Sold Summary

  • 43 Days On Market

  Last Listing Agent Liudmila Lobeeva eXp Realty

  3550 Route 9w, Highland, NY 12528
• 

  Est $548,530

  Not Listed For Sale

  206 Plutarch Rd, Highland, NY 12528

  • 3 Beds
  • 3 Baths
  • 1,946 Sq Ft
  • Built 2006

  206 Plutarch Rd, Highland, NY 12528

  Last Sold Summary

  • 18 Days On Market
• 

  

  /31

  $500,000

  Under Contract

  • Land
  • 97.1 Acres
  • $5,149 per Acre

  TBD Lily Lake Rd, Highland, NY 12528

  A rare opportunity to own a breathtaking 97-acre property featuring the very lake that gives Lily Lake Road its name. Tucked away in the beautiful countryside of Highland, New York, this one-of-a-kind parcel offers unmatched privacy, natural beauty, and endless potential for your dream retreat or legacy estate. At the heart of the property lies Lily Lake — a serene, private body of water

  John Quinn Quinn Realty Group Inc.

  TBD Lily Lake Rd, Highland, NY 12528

Showing Results 121 - 160, Page 4 of 18