Highland, NY Homes

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  /50

  $680,000

  • 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
• 

  $260,000 Sold Jun 24, 2025

  411 Vineyard Ave, Highland, NY 12528

  • 3 Beds
  • 1 Bath
  • 1,040 Sq Ft
  • Built 1963

  Last Sold Summary

  • 21% Below List Price
  • $250/SF
  • 141 Days On Market

  Current Estimated Value $279,059

  Last Listing Agent Brian Smith River Realty Services, Inc.

  411 Vineyard Ave, Highland, NY 12528
• 

  Est $401,836 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

  • 46% Above List Price
  • $179/SF
  • 140 Days On Market

  • Last Sold Price $275,000
  • Sep 30, 2024

  Last Listing Agent Maria Murphy Keller Williams Realty
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  /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
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  $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 $567,660

  Last Listing Agent Kristabelle McDermott The Machree Group, LLC

  38 Mayer Dr, Highland, NY 12528
• 

  Est $469,867 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

  • 17% Above List Price
  • $228/SF
  • 88 Days On Market

  • Last Sold Price $400,000
  • Nov 08, 2024

  Last Listing Agent Dawn Passante Coldwell Banker Village Green
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  /31

  $500,000

  • 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
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  /31

  $369,000 Sold Jul 07, 2025

  10 Perkinsville Rd, Highland, NY 12528

  • 3 Beds
  • 2 Baths
  • 1,311 Sq Ft
  • Built 1987

  Last Sold Summary

  • 4% Below List Price
  • $281/SF
  • 29 Days On Market

  Current Estimated Value $404,067

  Last Listing Agent Ewa Kusmierek eXp Realty, LLC

  10 Perkinsville Rd, Highland, NY 12528
• 

  Est $717,861 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

  • 20% Above List Price
  • $263/SF
  • 26 Days On Market

  • Last Sold Price $599,700
  • Oct 19, 2023

  Last Listing Agent EILEEN FESKO BHHS Hudson Valley Properties
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  /14

  $265,000

  • 1 Bed
  • 1 Bath
  • 730 Sq Ft

  128 Vineyard Ave Unit 201, 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 201, 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 $414,087

  Last Listing Agent John Durso Keller Williams Realty Partner

  18 Grove St, Highland, NY 12528
• 

  Est $368,196 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% Above List Price
  • $200/SF
  • 16 Days On Market

  • Last Sold Price $317,500
  • Mar 31, 2025

  Last Listing Agent Rebecca Kaufman Q Home Sales
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  /30

  $369,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,104 Sq Ft

  534 U S 44, Highland, NY 12528

  Set high on a hill with mountain views, this fully remodeled home is turn-key and ready to enjoy. The open floor plan connects the kitchen, dining, and living areas--ideal for both everyday living and entertaining. The first floor also features a convenient half bath and laundry room, while upstairs offers three bedrooms and two baths, including a primary bedroom with ensuite. The updated

  Sally Sprogis Four Seasons Sothebys Intl

  534 U S 44, 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 $391,119

  Last Listing Agent Christopher Baker River to Ridge Rlty Associates

  2 Cambridge Ct, Highland, NY 12528
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  Est $456,191 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

  • 6% Above List Price
  • $226/SF
  • 176 Days On Market

  • Last Sold Price $429,000
  • Jun 14, 2024

  Last Listing Agent Dylan Taft Taft Street Realty, Inc.
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  /18

  $100,000

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

  3550 Route 9w, Highland, NY 12528

  Prime development opportunity in the heart of Highland! This property is ideally located on Route 9W with excellent visibility and accessibility, featuring Town water and sewer—a rare and valuable combination for future development. Zoned GB (General Business), offering a wide range of permitted uses including retail, office, service businesses, and mixed-use potential (buyer to verify).

  Liudmila Lobeeva eXp Realty

  3550 Route 9w, Highland, NY 12528
• 

  $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 $426,085

  Last Listing Agent jeff farnell John J Lease REALTORS Inc

  59 South St, Highland, NY 12528
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  Est $585,500 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

  • 6% Above List Price
  • $195/SF
  • 5 Days On Market

  • Last Sold Price $550,000
  • Dec 05, 2023

  Last Listing Agent Dylan Taft Taft Street Realty, Inc.
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  /25

  $397,000

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

  7 River Rd, Highland, NY 12528

  UNIQUE FLOOR PLAN in this updated eyebrow colonial creates an ideal setup for a bed-and-breakfast use of this property. Each bedroom features it's own full bath, offering comfort and privacy for all. The spacious living area includes a formal dining room and updated kitchen. A first- floor bedroom and convenient laundry add to the home's flexibility. Enjoy a short walk to the Hamlet of Highland

  Elizabeth Decker Hudson Dwellings Realty

  7 River Rd, 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 $173,708

  Last Listing Agent Kathy Dawson Howard Hanna Rand Realty

  69 North Rd, Highland, NY 12528
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  /27

  Est $318,068 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

  • 3% Above List Price
  • $245/SF
  • 63 Days On Market

  • Last Sold Price $307,500
  • Oct 17, 2024

  Last Listing Agent Paige McClintock Howard Hanna Rand Realty
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  /13

  $265,000

  • 1 Bed
  • 1 Bath
  • 730 Sq Ft

  128 Vineyard Ave Unit 206, 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 206, Highland, NY 12528
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  /45

  $700,000 Sold Aug 04, 2025

  354 Plutarch Rd, Highland, NY 12528

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

  Last Sold Summary

  • 7% Below List Price
  • $314/SF
  • 46 Days On Market

  Current Estimated Value $707,268

  Last Listing Agent Nicola Friedman Windsor Realty Services, Inc.

  354 Plutarch Rd, Highland, NY 12528
• 

  /2

  Est $449,997 Not Listed For Sale

  280 Orchard Rd, Highland, NY 12528

  • 3 Beds
  • 2 Baths
  • 1,996 Sq Ft
  • Built 1957

  280 Orchard Rd, Highland, NY 12528

  Last Sold Summary

  • 15% Below List Price
  • $195/SF

  • Last Sold Price $390,000

  Last Listing Agent CAROLYN DE MICHELE
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  /30

  $179,000

  • Land
  • 3.02 Acres
  • $59,272 per Acre

  44 Vineyard Ave, Highland, NY 12528

  Gorgeous wooded 3 acre flag lot with view potential to the east and south. Great commuter location minutes from the NYC trains and the NYS Thruway. Driveway has been roughed in for you and the septic approval will need to be redone. Power and cable will be brought in around 350' by the seller. Excellent location for a full time or weekend home. Old stone walls line the southern and western edges.

  Bruce Stalnaker Coldwell Banker Village GreenN

  44 Vineyard Ave, 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 $388,922

  Last Listing Agent Brenda Watington W Manor LLC

  785 South St, Highland, NY 12528
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  /2

  Est $687,612 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

  Last Sold Summary

  • 7% Below List Price
  • $242/SF

  • Last Sold Price $640,000

  Last Listing Agent John Quinn Quinn Realty Group Inc
• 

  

  /17

  $50,000

  • Land
  • 1.36 Acres
  • $36,765 per Acre

  0 White St, Highland, NY 12528

  Looking for the perfect lot for your new home? This lovely 1.36-acre wooded lot is situated on a gentle rise above an established community in historic Highland. It offers the best of both worlds; peace, privacy, and gorgeous elevated views, with convenient access to all amenities and the security of having neighbors around if needed. Easy access to the Walkway Over the Hudson, Empire State Rail

  Carolyn Michelle KW Mid-Hudson

  0 White St, Highland, NY 12528
• 

  $277,000 Sold Jul 15, 2025

  23 Toc Dr, Highland, NY 12528

  • 3 Beds
  • 1.5 Baths
  • 1,272 Sq Ft
  • Built 1985

  Last Sold Summary

  • 1% Below List Price
  • $218/SF
  • 102 Days On Market

  Current Estimated Value $282,110

  Last Listing Agent Randy Spiesman Weichert REALTORS

  23 Toc Dr, Highland, NY 12528
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  /33

  Est $523,139 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

  • 9% Above List Price
  • $214/SF
  • 34 Days On Market

  • Last Sold Price $480,000
  • Jan 08, 2024

  Last Listing Agent Savannah Miceli Century 21 Alliance-NP
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  /14

  $270,000

  • 1 Bed
  • 1 Bath
  • 803 Sq Ft

  128 Vineyard Ave Unit 106, 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 803-square-foot first-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 custom

  Andrea Babcock Onyx Property Management LLC

  128 Vineyard Ave Unit 106, Highland, NY 12528
• 

  

  /23

  $295,000 Sold Jul 09, 2025

  4 Sunnybrook Cir, Highland, NY 12528

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

  Last Sold Summary

  • 2% Above List Price
  • $242/SF
  • 110 Days On Market

  Last Listing Agent Anita Cunniff Boxwood Realty and Design

  4 Sunnybrook Cir, Highland, NY 12528
• 

  Est $403,130 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

  • 5% Above List Price
  • $290/SF
  • 113 Days On Market

  • Last Sold Price $383,000
  • Mar 14, 2025

  Last Listing Agent JoAnn Ellis Summerset Realty
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  /7

  $399,900 Pending

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

  29 Oakes Rd, Highland, NY 12528

  An exceptional and rare opportunity to own a piece of the Hudson Riverfront between two of the region’s most iconic landmarks, the Mid-Hudson Bridge and the Walkway Over the Hudson. Located on the Highland side, presenting a blend of natural beauty and historic charm. At the heart of the property is a c.1840s two bedroom, one bath home, offering timeless character and panoramic views of the

  Anthony DeGelormo Century 21 Alliance Rlty Group

  29 Oakes Rd, Highland, NY 12528
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  /41

  $390,500 Sold Jun 24, 2025

  217 Hawley's Corners Rd, Highland, NY 12528

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

  Last Sold Summary

  • 3% Above List Price
  • $252/SF
  • 42 Days On Market

  Last Listing Agent Angela Paul Past Member

  217 Hawley's Corners Rd, Highland, NY 12528
• 

  Est $364,792 Not Listed For Sale

  64 Argent Dr, Highland, NY 12528

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

  64 Argent Dr, Highland, NY 12528

  Last Sold Summary

  • 1% Above List Price
  • $245/SF
  • 89 Days On Market

  • Last Sold Price $360,000
  • Nov 22, 2024

  Last Listing Agent Stacie Mooradian Howard Hanna Rand Realty
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  /34

  $305,000 Pending

  • 2 Beds
  • 1 Bath
  • 946 Sq Ft

  791 Gregory Ct Unit 706, Highland, NY 12528

  Immaculate first-floor two bedroom end-unit condominium in Highland, NY. located in the sought-after Woods at Bridgeview Community. Enjoy the French-door study and covered patio off the living room with wooded views into Franny Reese Park. A quick three minute car ride brings you to the Hudson Valley Rail Trail, that connects to the Walkway of the Hudson. Highlights of this well-maintained home

  Barbara Carter Century 21 Alliance Rlty Group

  791 Gregory Ct Unit 706, 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 $323,011

  Last Listing Agent Naomi Streicher Q Home Sales

  38 Sunny Brook Cir, Highland, NY 12528
• 

  Est $367,005 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

  • 8% Above List Price
  • $231/SF
  • 27 Days On Market

  • Last Sold Price $340,000
  • Jul 19, 2023

  Last Listing Agent Simone Edwards Edwards Properties
• 

  

  /22

  $2,100,000

  • Land
  • 70.5 Acres
  • $29,787 per Acre

  243 Vineyard Ave Unit 251, Highland, NY 12528

  Spectacular 70 acre parcel located right outside the village of Highland. May be used as a farm or subdivided. Parcel has 3 rentals located on it in addition to 1 vacant house. Also on this property is a very large steel building with high ceilings and oversized garage doors as well as a barn! Close commuter location - Metro North, NYS Thruway, Mohonk Mountains and Hudson Valley Rail Trail.

  John Quinn Quinn Realty Group Inc

  243 Vineyard Ave Unit 251, Highland, NY 12528

Showing Results 161 - 200, Page 5 of 18