Highland, NY Homes

• 

  

  

  /25

  Est $750,863

  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

  Last Listing Agent Jason Schobert eXp Realty, LLC
• 

  

  

  /45

  $695,000

  $30K PRICE DROP

  • 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
• 

  $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 $452,392

  Last Listing Agent Leigh Wagner-Quintana KW Hudson Valley North

  334 Pancake Hollow Rd, Highland, NY 12528
• 

  Est $369,288

  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

  Last Listing Agent Darlene Provino Century 21 E & M Williams Rlty
• 

  

  

  /49

  $697,000

  • 5 Beds
  • 6 Baths
  • 2,774 Sq Ft

  90 New Paltz Rd, Highland, NY 12528

  Grand Highland Home with Exceptional Living and Entertaining Spaces. Welcome to this stately Highland residence, proudly perched atop a beautiful knoll and offering that unmistakable feeling of coming home the moment you arrive. This grand 5-bedroom home combines spacious living, thoughtful updates, and an incredible setting designed for both everyday enjoyment and memorable entertaining. The

  Dawn Passante Coldwell Banker Village Green

  90 New Paltz Rd, Highland, NY 12528
• 

  

  /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 $477,277

  Last Listing Agent Leigh Wagner-Quintana Past Member

  41 New Paltz Rd, Highland, NY 12528
• 

  

  /49

  Est $559,842

  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

  Last Listing Agent Barbara Korabel Four Seasons Realty Group
• 

  

  /14

  $399,000

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

  0 York Lake Estates Rd Unit 11927216, 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 11927216, Highland, NY 12719
• 

  $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 $320,411

  Last Listing Agent John Durso Keller Williams Realty Partner

  660 Gregory Ct Unit 410, Highland, NY 12528
• 

  Est $445,654

  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

  Last Listing Agent Gary MacEntee Keller Williams Realty
• 

  

  /34

  $419,900

  $30K PRICE DROP Pending

  • 4 Beds
  • 2 Baths
  • 1,382 Sq Ft

  52 Phillips Ave, Highland, NY 12528

  This one checks all the boxes! Welcome to 52 Phillips Ave where you have the best a home can offer having been recently renovated, inside and out and with direct access to the Hudson Valley Rail Trial. It is close to downtown amenities and just two minutes to the Mid-Hudson Bridge. This home was lovingly renovated to include modern updates while maintaining charm throughout. The main level

  Amy Hawks Berardi Realty

  52 Phillips Ave, Highland, NY 12528
• 

  $650,000

  Sold Aug 15, 2026

  196 Vineyard Ave, Highland, NY 12528

  • 5 Beds
  • 4 Baths
  • 3,522 Sq Ft
  • Built 1986

  Last Sold Summary

  • 4% Below List Price
  • $185/SF
  • 35 Days On Market

  Current Estimated Value $672,583

  Last Listing Agent Angela Briante Briante Realty Group, LLC

  196 Vineyard Ave, Highland, NY 12528
• 

  Est $345,450

  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

  Last Listing Agent Alexandra Taylor KW Hudson Valley North
• 

  

  /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
• 

  

  /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 $326,577

  Last Listing Agent Nancy Senescu Bella NS Properties LLC

  329 Gregory Ct Unit 509, Highland, NY 12528
• 

  Est $436,597

  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

  Last Listing Agent Virginia Corbett eXp Realty
• 

  /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
• 

  

  /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 $341,865

  Last Listing Agent Dawn Passante Coldwell Banker Village GreenN

  39 Sunnybrook Cir, Highland, NY 12528
• 

  Est $566,020

  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

  Last Listing Agent Richard Baxter Keller Williams Realty
• 

  

  /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
• 

  $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 $413,116

  Last Listing Agent Megan Krusen eXp Realty

  16 Orchard Ln, Highland, NY 12528
• 

  

  /24

  Est $498,585

  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

  Last Listing Agent Barbara Carter Past Member
• 

  

  /16

  $200,000

  Pending

  • 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

  Siobhan Fahy eXp Realty

  TBD Loughran Ln, 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 $334,995

  Last Listing Agent Michele Marina Atlantica East Associates LLC

  578 South St, Highland, NY 12528
• 

  Est $485,806

  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

  Last Listing Agent Tristen Sierra Coldwell Banker Realty
• 

  

  /32

  $895,000

  • 4 Beds
  • 2.5 Baths
  • 2,961 Sq Ft

  3 Elbow Ln, Highland, NY 12528

  Experience the pinnacle of upscale country living in this stunning, newly constructed 2,961-square-foot masterpiece. Nestled on 5.4 partially wooded acres in the scenic Hudson Valley, this architectural gem offers the perfect blend of private sanctuary and modern luxury, all just moments from the historic Hudson River.As you approach, a magnificent covered front porch welcomes you, offering

  Adriane Werkema Easy Lifestyle Real Estate

  3 Elbow Ln, 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 $1,103,523

  Last Listing Agent Melissa Pettinella Century 21 Alliance Realty Grp

  243 Hawleys Corners Rd, Highland, NY 12528
• 

  Est $397,476

  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

  Last Listing Agent Dawn Gregg Curasi Realty, Inc.
• 

  

  /19

  $150,000

  Pending

  • 3 Beds
  • 3 Baths
  • 1,232 Sq Ft

  91 Pancake Hollow Rd, Highland, NY 12528

  With major capital improvements already completed, 91 Pancake Hollow Road presents an excellent opportunity for investors, builders, or buyers looking to customize a home with significant upside. Recent upgrades include a new roof, new front deck, new septic system, and new HVAC system. Inside, the home has been stripped to the studs, offering a blank canvas for a full renovation.Ideally

  Jeffery Dolfinger Century 21 Hudson Valley Rlty.

  91 Pancake Hollow Rd, Highland, NY 12528
• 

  $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 $394,307

  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

  Last Listing Agent Megan Rios Berardi Realty
• 

  

  /43

  $799,000

  Open Sat 11AM - 1PM

  • 4 Beds
  • 2.5 Baths
  • 2,458 Sq Ft

  125 Vineyard Ave, Highland, NY 12528

  Step into the character and craftsmanship of this beautiful historic Victorian in the heart of Highland, New York. A welcoming wrap-around porch sets the stage for a home filled with original details, thoughtful updates, and timeless Hudson Valley charm. Inside, beautiful hardwood floors, original woodwork, and classic pocket doors showcase the craftsmanship of a bygone era. The gracious

  Anthony D'Amato BHHS Hudson Valley Properties

  125 Vineyard Ave, Highland, NY 12528
• 

  

  /25

  $320,000

  Sold Sep 11, 2026

  7 River Rd, Highland, NY 12528

  • 3 Beds
  • 3 Baths
  • 1,661 Sq Ft
  • Built 1830

  Last Sold Summary

  • 19% Below List Price
  • $193/SF
  • 286 Days On Market

  Current Estimated Value $398,328

  Last Listing Agent Elizabeth Decker Hudson Dwellings Realty

  7 River Rd, 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

  Last Listing Agent IRENE MOODY BHHS Hudson Valley Properties
• 

  

  /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
• 

  

  /33

  $560,000

  Sold Feb 24, 2026

  38 Mayer Dr, Highland, NY 12528

  • 3 Beds
  • 3 Baths
  • 1,918 Sq Ft
  • Built 1989

  Last Sold Summary

  • 7% Below List Price
  • $292/SF
  • 24 Days On Market

  Current Estimated Value $578,298

  Last Listing Agent Kristabelle McDermott The Machree Group, LLC

  38 Mayer Dr, Highland, NY 12528
• 

  Est $484,925

  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

  Last Listing Agent Naomi Streicher Q Home Sales
• 

  

  /31

  $450,000

  • 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
• 

  $415,000

  Sold Apr 21, 2026

  18 Grove St, Highland, NY 12528

  • 3 Beds
  • 3 Baths
  • 1,892 Sq Ft
  • Built 1923

  Last Sold Summary

  • 2% Below List Price
  • $219/SF
  • 32 Days On Market

  Current Estimated Value $410,849

  Last Listing Agent John Durso Keller Williams Realty Partner

  18 Grove St, Highland, NY 12528
• 

  Est $251,278

  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

  Last Listing Agent Desiree Beecham River Realty Services, Inc.

Showing Results 121 - 160, Page 4 of 18