Highland, NY Homes

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  /9

  $39,900

  • Land
  • 2.82 Acres
  • $14,149 per Acre

  Lot 57.1 Yulan-Barryville Rd, Highland, NY 12791

  Looking for a spot to build your dream home, look no further! This nice mostly level property is wooded with some open space. There is 288' of road frontage and the property is approximately 400' deep. Located close to the towns of Barryville and Yulan. Close to the Delaware River. Land is selling quickly, so schedule your appointment today!

  

  Dawn Curreri

  EAGLE VALLEY REALTY

  Lot 57.1 Yulan-Barryville Rd, Highland, NY 12791
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  $2,400 Per Month

  • 2 Beds
  • 2.5 Baths
  • 1,300 Sq Ft
  • Townhouse for Rent

  794 South St Unit 1, Highland, NY 12528

  Beautiful townhouse style apartment ready for immediate lease. Renovated, clean, and newer construction, 794 South St Unit 1 is ready for its next lessee to settle in and get comfortable. This end unit features 1300 sq ft of living space sprawling over two floors. The modern floor plan boasts walk-in closets, full bathrooms off each bedroom, open kitchen, spacious living room, first floor

  DANIEL DICKINSON Dickinson Properties LLC

  794 South St Unit 1, Highland, NY 12528
• 

  $559,000

  Sold Dec 09, 2025

  19 Emerson Terrace, Highland, NY 12528

  • 3 Beds
  • 3 Baths
  • 2,668 Sq Ft
  • Built 2021

  Last Sold Summary

  • $210/SF
  • 87 Days On Market

  Current Estimated Value $597,371

  Last Listing Agent Susan Todd BHHS Hudson Valley Properties

  19 Emerson Terrace, Highland, NY 12528
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  Not Listed For Sale

  330 Station Rd, Highland, NY 12528

  • 3 Beds
  • 3.5 Baths
  • 3,491 Sq Ft
  • Built 2025

  330 Station Rd, Highland, NY 12528

  Last Sold Summary

  • 84 Days On Market

  Last Listing Agent Danielle Bartula Howard Hanna Rand Realty
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  /2

  $300,000

  • Land
  • 11.57 Acres
  • $25,929 per Acre

  (Lot 2) 111 South St, Highland, NY 12528

  Build your custom dream home on this shovel-ready 11.57-acre homesite in a newly approved and recorded 4-lot subdivision totaling nearly 49 acres. All the hard work is done: perc test completed, well & septic approved by the Ulster County Board of Health, and electric & fiber already run to the shared driveway. Accessed via a common driveway, the lot offers privacy and a natural Hudson Valley

  

  Mark Friedman

  McGrath Realty Inc

  (Lot 2) 111 South St, Highland, NY 12528
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  /19

  $2,600 Per Month

  • 2 Beds
  • 1 Bath
  • 946 Sq Ft
  • Condo for Rent

  561 Gregory Ct, Highland, NY 12528

  Newly renovated 2 BR/ 1bath + den condominium ideally located minutes from the Mid-Hudson Bridge available for rent September 1, 2026. Minutes from major shopping and restaurants as well as the Walkway Over the Hudson State Park, major roadways and businesses in the Highland Central School District.

  John Quinn Quinn Realty Group Inc.

  561 Gregory Ct, Highland, NY 12528
• 

  $620,000

  Sold Jan 05, 2026

  93 Glen Rock Cir, Highland, NY 12528

  • 4 Beds
  • 2.5 Baths
  • 2,270 Sq Ft
  • Built 2008

  Last Sold Summary

  • 9% Above List Price
  • $273/SF
  • 26 Days On Market

  Current Estimated Value $656,785

  Last Listing Agent Randy Spiesman Weichert REALTORS

  93 Glen Rock Cir, Highland, NY 12528
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  /26

  Not Listed For Sale

  7 Sunnybrook Cir, Highland, NY 12528

  • 3 Beds
  • 1.5 Baths
  • 1,160 Sq Ft
  • Built 1974

  7 Sunnybrook Cir, Highland, NY 12528

  Last Sold Summary

  • 25 Days On Market

  Last Listing Agent Michele Rios BHHS Hudson Valley Properties
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  /48

  $1,200,000

  $95K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,919 Sq Ft

  15 Oakes Rd, Highland, NY 12528

  Welcome to The Riverhouse, an extraordinary custom Lindal Cedar home offering front-row living on the Hudson River.A wall of glass and voluminous ceilings frame breathtaking, ever-changing water views, filling the dramatic great room and its striking fireplace with a light-filled, airy atmosphere. The stylish chef's kitchen is both sleek and functional, featuring high-end cabinetry,

  

  Mark McAlpine

  Compass Greater New York, LLC

  15 Oakes Rd, Highland, NY 12528
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  /8

  $1,900 Per Month

  • 1 Bed
  • 1 Bath
  • 920 Sq Ft
  • Apartment for Rent

  28 Toc Dr Unit 1, Highland, NY 12528

  Fully renovated 1-bedroom apartment available in Highland, NY! This bright and welcoming unit features updated flooring, refreshed lighting, and a clean, stylish feel throughout. The bedroom offers great natural light and ample closet space. Conveniently located near local shops, restaurants, and public transportation, this apartment offers both comfort and convenience in the heart of Highland.

  Yesenia Pagan Keller Williams Realty Partner

  28 Toc Dr Unit 1, Highland, NY 12528
• 

  $527,000

  Sold May 20, 2026

  44 Clearwater Rd, Highland, NY 12528

  • 4 Beds
  • 3 Baths
  • 2,850 Sq Ft
  • Built 1969

  Last Sold Summary

  • 2% Above List Price
  • $185/SF
  • 33 Days On Market

  Current Estimated Value $544,526

  Last Listing Agent Jacob Cohen eXp Realty

  44 Clearwater Rd, Highland, NY 12528
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  Not Listed For Sale

  420 Crescent Ave, Highland, NY 12528

  • 24 Beds
  • 23 Baths
  • 15,000 Sq Ft
  • Built 1972

  420 Crescent Ave, Highland, NY 12528

  Last Sold Summary

  • 26 Days On Market

  Last Listing Agent Matt Eyler New Paltz Properties
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  /17

  $649,999

  • 4 Beds
  • 3 Baths
  • 2,241 Sq Ft

  213 Tuckers Corners Rd, Highland, NY 12528

  NEW CONSTRUCTION!!! Estimated to be completed the beginning of August - This stunning new construction ranch-style home offers 2,241 square feet of refined, single-level living space featuring four spacious bedrooms, three full bathrooms, and an attached two-car garage, all set on a sprawling and private 10.20 -acre estate within the Marlboro School District. While the foundation for luxury is

  

  Richard Baxter

  Keller Williams Realty

  213 Tuckers Corners Rd, Highland, NY 12528
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  /20

  $2,600 Per Month

  • 2 Beds
  • 1.5 Baths
  • 1,047 Sq Ft
  • Townhouse for Rent

  56 Sterling Place, Highland, NY 12528

  Charming 2-Bedroom Townhouse for Rent in Highland, NYWelcome to 56 Sterling Place in Highland, NY! This inviting 2-bedroom, 1.5-bath townhouse offers comfortable living in a welcoming community with fantastic amenities right at your doorstep.Residents can enjoy a variety of community amenities, including a swimming pool, tennis courts, basketball courts, and a playground—providing

  John Quinn Quinn Realty Group Inc

  56 Sterling Place, Highland, NY 12528
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  /38

  $380,000

  Sold Oct 03, 2025

  399 New Paltz Rd, Highland, NY 12528

  • 4 Beds
  • 3 Baths
  • 2,700 Sq Ft
  • Built 1992

  Last Sold Summary

  • 9% Above List Price
  • $141/SF
  • 18 Days On Market

  Current Estimated Value $423,619

  Last Listing Agent Dawn Passante Coldwell Banker Village GreenN

  399 New Paltz Rd, Highland, NY 12528
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  Not Listed For Sale

  546 South St, Highland, NY 12528

  • 5 Beds
  • 2 Baths
  • 2,500 Sq Ft
  • Built 1932

  546 South St, Highland, NY 12528

  Last Sold Summary

  • 81 Days On Market

  Last Listing Agent Lindsay Stevens eXp Realty
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  /18

  $165,000

  Pending

  • 3 Beds
  • 1 Bath
  • 928 Sq Ft

  41 Grand St, Highland, NY 12528

  Opportunity Knocks Bring Your Vision! This charming circa 1800 Cape style home (928 sq ft) is ready for its next chapter. Sitting on a level lot with mature trees and a classic covered front porch, this property offers solid bones and endless potential for the right buyer. Whether you're an investor looking for your next project, a first-time buyer ready to build equity, or a handy homeowner with

  

  Danielle Carlson-Murphy

  Start Home Smart, Inc.

  41 Grand St, Highland, NY 12528
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  /49

  $7,492 Per Month

  • 3 Beds
  • 2.5 Baths
  • 2,531 Sq Ft
  • House for Rent

  475 N Riverside Rd, Highland, NY 12528

  Nestled on a picturesque 5.7-acre setting and set well back from the road, this stunning and prestigious A-Frame home offers privacy, beauty, and exceptional living space. A long, scenic driveway welcomes you to this one-of-a-kind property, where natural surroundings and timeless architecture create a true Hudson Valley retreat. The main level features 3 bedrooms and 3.5 bathrooms, including a

  Anne Marie O'Brien Curasi Realty, Inc.

  475 N Riverside Rd, Highland, NY 12528
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  $300,000

  Sold Apr 15, 2026

  787 Gregory Ct, Highland, NY 12528

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

  Last Sold Summary

  • 2% Above List Price
  • $317/SF
  • 18 Days On Market

  Current Estimated Value $299,330

  Last Listing Agent Eugene Valoy BHHS Hudson Valley Properties

  787 Gregory Ct, Highland, NY 12528
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  Not Listed For Sale

  217 Hawley's Corners Rd, Highland, NY 12528

  • 3 Beds
  • 2 Baths
  • 1,547 Sq Ft
  • Built 1900

  217 Hawley's Corners Rd, Highland, NY 12528

  Last Sold Summary

  • 42 Days On Market

  Last Listing Agent Angela Paul Past Member
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  /2

  $350,000

  • Land
  • 14.5 Acres
  • $24,138 per Acre

  (Lot 3) 111 South St, Highland, NY 12528

  Build your custom dream home on this shovel-ready 13-acre homesite in a newly approved and recorded 4-lot subdivision totaling nearly 49 acres. All the hard work is done: perc test completed, well & septic approved by the Ulster County Board of Health, and electric & fiber already run to the shared driveway. Accessed via a common driveway, the lot offers privacy and a natural Hudson Valley

  

  Mark Friedman

  McGrath Realty Inc

  (Lot 3) 111 South St, Highland, NY 12528
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  /13

  $2,900 Per Month

  • 3 Beds
  • 1.5 Baths
  • 2,000 Sq Ft
  • House for Rent

  155-157 Vineyard Ave, Highland, NY 12528

  Charming Highland Rental - 155-157 Vineyard Ave, Highland, NY 12528This conveniently located rental offers a comfortable place to call home in the heart of the Hudson Valley.The home features large 3 bedrooms and 1.5 bathrooms, with an open layout in the living area. Enjoy the ample yard along with the convenience of being close to everything Highland has to offer.The location

  John Quinn Quinn Realty Group Inc.

  155-157 Vineyard Ave, Highland, NY 12528
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  /27

  $625,000

  Sold Jun 01, 2026

  660 N Chodikee Lake Rd, Highland, NY 12528

  • 3 Beds
  • 2 Baths
  • 3,486 Sq Ft
  • Built 1974

  Last Sold Summary

  • 7% Above List Price
  • $179/SF
  • 35 Days On Market

  Current Estimated Value $618,658

  Last Listing Agent Hayes Clement Compass Greater New York, LLC

  660 N Chodikee Lake Rd, Highland, NY 12528
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  Not Listed For Sale

  9 White Pine Ln, Highland, NY 12719

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Built 2025

  9 White Pine Ln, Highland, NY 12719

  Last Sold Summary

  • 43 Days On Market

  Last Listing Agent Megan Kinealy Country House Realty Inc
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  /3

  $469,000

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  224 Vineyard Ave, Highland, NY 12528

  Ready-To-Build 3-Bedroom Home with Mountain Views - Prime Location Near Town This won't last long ready to-built. Still time to customize the floor plan, pick colors, countertops and more. 3-bedroom, 2-bathroom home on a scenic .24-acre lot with stunning Illinois Mountain views. Perfectly situated just minutes from town, you'll enjoy close proximity to restaurants, the train station, wineries,

  

  Danielle Carlson-Murphy

  Start Home Smart, Inc.

  224 Vineyard Ave, Highland, NY 12528
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  /8

  $2,000 Per Month

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft
  • Apartment for Rent

  635 South St Unit 8, Highland, NY 12528

  Newly renovated, two bedroom, one bath apartment in a peaceful and serene setting. Commuter friendly with it's proximity to Rt. 9W & 299, Mid-Hudson & Newburgh-Beacon Bridges, NYS Thruway & I-84 as well as the Poughkeepsie Train Station. It is also centrally located to dining, shopping & entertainment. No pets, no smoking or vaping on the premises.

  Kathleen Mackey Summerset Realty

  635 South St Unit 8, Highland, NY 12528
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  /23

  $278,000

  Sold Jan 28, 2026

  48 Sunny Brook Cir, Highland, NY 12528

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1974

  Last Sold Summary

  • 6% Below List Price
  • $263/SF
  • 32 Days On Market

  Current Estimated Value $291,589

  Last Listing Agent Leigh Wagner-Quintana Past Member

  48 Sunny Brook Cir, Highland, NY 12528
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  /23

  Not Listed For Sale

  4 Sunnybrook Cir, Highland, NY 12528

  • 3 Beds
  • 1.5 Baths
  • 1,220 Sq Ft
  • Built 1974

  4 Sunnybrook Cir, Highland, NY 12528

  Last Sold Summary

  • 110 Days On Market

  Last Listing Agent Anita Cunniff Boxwood Realty and Design
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  $550,000

  $25K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,224 Sq Ft

  9 Roxanne Blvd, Highland, NY 12528

  Welcome to this beautifully maintained split-level home, offering the perfect blend of comfort, functionality, and style. Featuring 4 spacious bedrooms and 3 full bathrooms, plus an additional flex room on the lower level that can serve as a 5th bedroom, home office, or recreation space, this home provides room for everyone.Freshly painted and situated on a quiet dead-end street in one of the

  Simone Edwards Edwards Properties

  9 Roxanne Blvd, Highland, NY 12528
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  /7

  $1,950 Per Month

  • 2 Beds
  • 1 Bath
  • 750 Sq Ft
  • Apartment for Rent

  70 New Paltz Rd Unit 2D, Highland, NY 12528

  2 Bedroom beautifully styled 2nd floor apartment on a country road in Highland. Close to Poughkeepsie and Metro North as well as New Paltz and Highland with amenities galore. I87 is only 4 miles away. Apartment is equipped with beautiful sleek stainless appliances and stylish cabinetry. The large windows allow for beautiful natural light. Access to a large back yard for cook outs and recreation.

  Pamela Di Martino Curasi Realty, Inc.

  70 New Paltz Rd Unit 2D, Highland, NY 12528
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  /49

  $417,865

  Sold Jan 14, 2026

  307 Vineyard Ave, Highland, NY 12528

  • 4 Beds
  • 2 Baths
  • 2,128 Sq Ft
  • Built 1900

  Last Sold Summary

  • $196/SF
  • 71 Days On Market

  Current Estimated Value $459,628

  Last Listing Agent Debra Dooley BHHS HUDSON VALLEY PROP-NP

  307 Vineyard Ave, Highland, NY 12528
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  Not Listed For Sale

  0 Split Rock Dr Unit KEYH6229813, Highland, NY 12719

  0 Split Rock Dr Unit KEYH6229813, Highland, NY 12719

  Last Sold Summary

  • 656 Days On Market

  Last Listing Agent Cody Van Houten eXp Realty
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  /32

  $1,995,000

  $195K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 3,511 Sq Ft

  400 N Elting Corners Rd, Highland, NY 12528

  Perched at the end of a long winding driveway and surrounded by 24 acres of private woods, this extraordinary steel-built contemporary home offers architectural sophistication tucked quietly into the landscape of Highland, NY. Designed as both a statement in modern design and a deeply immersive retreat, the home balances bold structural elements with warmth, texture, and a constant connection to

  Richard Vizzini Corcoran Country Living

  400 N Elting Corners Rd, Highland, NY 12528
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  /13

  $2,100 Per Month

  • 2 Beds
  • 1 Bath
  • 760 Sq Ft
  • Apartment for Rent

  47-49 Mile Hill Rd, Highland, NY 12528

  Beautifully Renovated 2-Bedroom Unit for RentWelcome home to this beautifully renovated 2-bedroom unit located on a quiet street, just minutes from the Hudson River and the Poughkeepsie Bridge. Enjoy convenient access to major commuter roads, shopping, restaurants, parks, and everything the area has to offer.This unit has been thoughtfully updated with:Brand-new carpet

  Marie-Louise Enderle BHHS Hudson Valley Properties

  47-49 Mile Hill Rd, Highland, NY 12528
• 

  $499,000

  Sold Feb 03, 2026

  123 Vineyard Ave, Highland, NY 12528

  • 4 Beds
  • 3 Baths
  • 2,400 Sq Ft
  • Built 1900

  Last Sold Summary

  • 17% Below List Price
  • $208/SF
  • 68 Days On Market

  Current Estimated Value $517,826

  Last Listing Agent Dawn Passante Coldwell Banker Village Green

  123 Vineyard Ave, Highland, NY 12528
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  Not Listed For Sale

  245 Upper Rd N, Highland, NY 12528

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1960

  245 Upper Rd N, Highland, NY 12528

  Last Sold Summary

  • 27 Days On Market

  Last Listing Agent Dan Axtmann BHHS Hudson Valley Properties
• 

  

  /20

  $199,000

  $50K PRICE DROP

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

  0 Browning Blvd Unit 27248900, Highland, NY 12719

  Escape to the beauty of lake living with this stunning 6.38-acre property 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.

  Cathy Nation Premier Land Hub

  0 Browning Blvd Unit 27248900, Highland, NY 12719
• 

  $51,000

  Sold Oct 31, 2025

  0 Summit Dr Unit KEYH6318306, Highland, NY 12732

  • Land
  • 5.04 Acres
  • $10,119 per Acre

  Last Sold Summary

  • 14% Below List Price
  • 361 Days On Market

  Last Listing Agent Dawn Payne Payne Team LLC

  0 Summit Dr Unit KEYH6318306, Highland, NY 12732
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  Not Listed For Sale

  53 Grand St, Highland, NY 12528

  • 2 Beds
  • 1 Bath
  • 728 Sq Ft
  • Built 1992

  53 Grand St, Highland, NY 12528

  Last Sold Summary

  • 29 Days On Market

  Last Listing Agent Elizabeth Decker Hudson Dwellings Realty
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  /6

  $227,000

  • Land
  • 3.9 Acres
  • $58,205 per Acre

  5 Elbow Ln, Highland, NY 12528

  Seasonal Hudson River Views. This lot was approved for an in ground septic system and engineered for a 4 bedroom home in 2011. Will need to be updated. Virgin land! Beautiful building lot in fairly new subdivision with underground electric service. Only minutes to the Mid Hudson Bridge, The Walkway Over the Hudson and many other attractions. Easy access to train and plane. Current new homes in

  Elizabeth Decker Hudson Dwellings Realty

  5 Elbow Ln, Highland, NY 12528

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