Highland, NY Homes

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  /36

  Est $294,210 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,125 Sq Ft

  10 Lauretta Dr, Highland, NY 12528

  10 Lauretta Dr, Highland, NY 12528
• 

  

  

  /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
• 

  $349,900 Sold Mar 05, 2025

  114 Half Moon Rd, Highland, NY 12528

  • 3 Beds
  • 2 Baths
  • 1,182 Sq Ft
  • Built 1900

  Last Sold Summary

  • $296/SF
  • 35 Days On Market

  Current Estimated Value $359,241

  Last Listing Agent Anne Marie O'Brien Curasi Realty, Inc.

  114 Half Moon Rd, Highland, NY 12528
• 

  Est $595,679 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,470 Sq Ft

  25 Lauretta Dr, Highland, NY 12528

  25 Lauretta Dr, Highland, NY 12528
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  /32

  $450,000

  • 4 Beds
  • 1.5 Baths
  • 3,140 Sq Ft

  668 U S 44, Highland, NY 12528

  With its over 100-year-old history, this home has only changed hands once before, a testament to its enduring appeal and the kind of place that's been lovingly maintained for generations.Set on 1.2 scenic acres, this charming three-story, 4-bedroom, 1.5-bath Colonial offers classic style and beautiful surroundings. A wraparound paved driveway with river stone posts leads to a two-car garage,

  Heather Hughes Hudson Dwellings Realty

  668 U S 44, Highland, NY 12528
• 

  $325,000 Sold Oct 30, 2025

  422 Gregory Ct Unit 307, Highland, NY 12528

  • 2 Beds
  • 2 Baths
  • 1,027 Sq Ft
  • Built 1991

  Last Sold Summary

  • 3% Above List Price
  • $316/SF
  • 21 Days On Market

  Last Listing Agent Nancy Diehl Rita Levine Real Estate

  422 Gregory Ct Unit 307, Highland, NY 12528
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  /26

  Est $625,814 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,400 Sq Ft

  21 Spring Meadow Ct, Highland, NY 12528

  21 Spring Meadow Ct, Highland, NY 12528
• 

  

  /19

  $299,000

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

  8 Sunny Brook Cir, Highland, NY 12528

  Tastefully updated 2 bedroom, 1.5 bath townhouse features renovated kitchen w/modern styling includes stainless appliances, pantry & open shelving. Spacious living room leads upstairs to primary bedroom w/walk-in closet, well proportioned second bedroom and office alcove. Two renovated bathrooms, new flooring & new a/c compressor. Large fenced bluestone patio for outdoor living enjoyment. Complex

  Dan Axtmann BHHS Hudson Valley Properties

  8 Sunny Brook Cir, Highland, NY 12528
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  /23

  $70,000 Sold Sep 09, 2025

  536 N Riverside Rd, Highland, NY 12528

  • 3 Beds
  • 1 Bath
  • 1,320 Sq Ft
  • Built 1900

  Last Sold Summary

  • 17% Above List Price
  • $53/SF
  • 7 Days On Market

  Current Estimated Value $195,667

  Last Listing Agent Kristi Mordica Welch Realty Inc.

  536 N Riverside Rd, Highland, NY 12528
• 

  Est $490,577 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,750 Sq Ft

  799 State Route 44 55, Highland, NY 12528

  799 State Route 44 55, Highland, NY 12528
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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
• 

  $580,000 Sold Jan 15, 2026

  5 Willow Dock Rd, Highland, NY 12528

  • 2 Beds
  • 2.5 Baths
  • 1,364 Sq Ft
  • Built 1860

  Last Sold Summary

  • 3% Below List Price
  • $425/SF
  • 28 Days On Market

  Last Listing Agent Lindsay Rothman Compass Greater NY LLC

  5 Willow Dock Rd, Highland, NY 12528
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  /11

  Est $438,169 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,420 Sq Ft

  269 Tuckers Corners Rd, Highland, NY 12528

  269 Tuckers Corners Rd, Highland, NY 12528
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  /18

  $349,000

  • 2 Beds
  • 2 Baths
  • 992 Sq Ft

  451 New Paltz Rd, Highland, NY 12528

  INVESTMENT PROPERTYThis 2 family property is conveniently located in Highland. Less than 10 minutes to the Village of New Paltz, and 15 minutes to the Mid-Hudson bridge.The location is just steps away from the Hudson Valley Rail Trail, which is a 7 mile paved trail from the Walkway over the Hudson to New Paltz.Each unit is a one bedroom one bath apartment. Private parking lot has

  Jaynie Aristeo Ridgeline Realty

  451 New Paltz Rd, Highland, NY 12528
• 

  $37,500 Sold Jan 15, 2025

  0 Split Rock Dr Unit KEYH6229813, Highland, NY 12719

  • Land
  • 5.17 Acres
  • $7,253 per Acre

  Last Sold Summary

  • 15% Below List Price
  • 656 Days On Market

  Last Listing Agent Cody Van Houten eXp Realty

  0 Split Rock Dr Unit KEYH6229813, Highland, NY 12719
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  Est $531,243 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,928 Sq Ft

  41 Jenkins Ln, Highland, NY 12528

  41 Jenkins Ln, Highland, NY 12528
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  /11

  $265,000

  • 1 Bed
  • 1 Bath
  • 730 Sq Ft

  128 Vineyard Ave Unit 207, Highland, NY 12528

  Welcome to Highbridge Crossing, a modern condominium building with direct access to the Hudson Valley Rail Trail in the heart of Highland, NY. Thoughtfully designed 1 and 2 bedroom residences range from 730 to 1,230 SF, blending smart design, comfort, and easy outdoor access—ideal for active living without sacrificing style. The open layouts feature large windows and a seamless flow throughout.

  Vitaly Isaacs Magic Of Great Neck Realty Inc

  128 Vineyard Ave Unit 207, Highland, NY 12528
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  /35

  $510,000 Sold Sep 16, 2025

  20-22 Milton Ave, Highland, NY 12528

  • 5 Beds
  • 5 Baths
  • 2,382 Sq Ft
  • Built 1890

  Last Sold Summary

  • 7% Below List Price
  • $214/SF
  • 69 Days On Market

  Last Listing Agent Hayes Clement Compass Greater New York, LLC

  20-22 Milton Ave, Highland, NY 12528
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  /28

  Est $280,977 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 895 Sq Ft

  355 Crescent Ave, Highland, NY 12528

  355 Crescent Ave, Highland, NY 12528
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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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  $450,000 Sold Oct 16, 2025

  224 Martin Ave, Highland, NY 12528

  • 3 Beds
  • 1.5 Baths
  • 1,633 Sq Ft
  • Built 1940

  Last Sold Summary

  • 5% Below List Price
  • $276/SF
  • 87 Days On Market

  Last Listing Agent Dawn Passante Coldwell Banker Village Green

  224 Martin Ave, Highland, NY 12528
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  /16

  Est $496,246 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,810 Sq Ft

  397 Crescent Ave, Highland, NY 12528

  397 Crescent Ave, Highland, NY 12528
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  /26

  $325,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,723 Sq Ft

  578 South St, Highland, NY 12528

  Meticulously Updated Highland Home with Pool and Pond. This thoughtfully updated property at 578 South Street offers exceptional value with continuous improvements through today. Ideally located near the Shawangunk Mountains with hiking trails and outdoor recreation, close to the historic Mohonk Mountain House resort, yet convenient to Metro North Railroad and all amenities. The first floor

  Michele Marina Atlantica East Associates LLC

  578 South St, Highland, NY 12528
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  /10

  $135,000 Sold Dec 09, 2025

  251 Fosler Rd, Highland, NY 12528

  • Land
  • 12.9 Acres
  • $10,465 per Acre

  Last Sold Summary

  • 10% Below List Price
  • 24 Days On Market

  Last Listing Agent Michelle England Howard Hanna Rand Realty

  251 Fosler Rd, Highland, NY 12528
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  Est $370,757 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,982 Sq Ft

  683 State Route 44 55, Highland, NY 12528

  683 State Route 44 55, Highland, NY 12528
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  /8

  $148,000

  • Land
  • 5.56 Acres
  • $26,619 per Acre

  0 Black Bear Ct, Highland, NY 12719

  Yess! Your Dreams Have Been Answered...This Rare Lot..Privacy/5+ Acres/ 40' Pond/ Silence/ 7 Min To Barryville/ 10 Minutes To EldredReady For You.. To Build YOUR Future Retreat!! Yes, Moss Covered Rocks And A Gentle Slope Allowing For A Walk Out Lower Level. Gorgeous Trees Tuck You Into Your Private Serenity. It All Begins With Your Land and Then Your Dream Home Can Be Designed

  Jessica Jagel Cabins & Canoes Real Estate

  0 Black Bear Ct, Highland, NY 12719
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  /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

  Last Listing Agent Ronnie Rebis Grist Mill Real Estate

  365 Crescent Ave Unit 367, Highland, NY 12528
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  /49

  Est $523,530 Not Listed For Sale

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

  23 Blossom Grove Ct, Highland, NY 12528

  23 Blossom Grove Ct, Highland, NY 12528
• 

  

  /25

  $397,000

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

  7 River Rd, Highland, NY 12528

  Charming 1830s Eyebrow Colonial. Spacious Living Area with formal Dining Room and updated Kitchen. Laundry and one bedroom on first floor. 3 bedrooms, 3 Bathrooms. Walk to the Hamlet of Highland and the Highland Landing Park on the mighty Hudson River. Many restaurants and shops nearby as well as the Hudson Vallely Rail Trail. Soothing sounds from babbling Twaalfskill stream across the street.

  Elizabeth Decker Hudson Dwellings Realty

  7 River Rd, Highland, NY 12528
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  $526,000 Sold Jul 24, 2025

  6 Emerson Terrace, Highland, NY 12528

  • 3 Beds
  • 4 Baths
  • 2,186 Sq Ft
  • Built 2017

  Last Sold Summary

  • 1% Above List Price
  • $241/SF
  • 19 Days On Market

  Current Estimated Value $538,688

  Last Listing Agent John Olivero Keller Williams Realty

  6 Emerson Terrace, Highland, NY 12528
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  Est $422,560 Not Listed For Sale

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

  11 Blossom Grove Ct, Highland, NY 12528

  11 Blossom Grove Ct, Highland, NY 12528
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  /33

  $599,000 Under Contract

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

  38 Mayer Dr, Highland, NY 12528

  Gorgeous, newly renovated 3BR, 3-full bathroom home in The Hudson Hills neighborhood of Lloyd, Highland. Open-layout-island kitchen with granite countertops & all new appliances. Skylights and bay windows (all triple pane) provide an abundance of natural light in the living/dining room. Sliders off the dining room lead to a new deck overlooking the backyard. Primary bedroom with large en-suite

  Kristabelle McDermott The Machree Group, LLC

  38 Mayer Dr, Highland, NY 12528
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  /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

  Last Listing Agent Leigh Wagner-Quintana Keller Williams Realty HV Nort

  41 New Paltz Rd, Highland, NY 12528
• 

  Est $310,738 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 918 Sq Ft

  835 South St, Highland, NY 12528

  835 South St, Highland, NY 12528
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  /39

  $425,000 Open Sat 11AM - 1PM

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

  18 Grove St, Highland, NY 12528

  Welcome to a truly turn-key home where thoughtful renovation meets everyday comfort. Completely transformed in 2017, this residence offers a bright, modern feel while delivering flexibility rarely found at this price point. The main living spaces flow beautifully, anchored by a stylish, fully updated kitchen featuring granite countertops, stainless steel appliances, and crisp cabinetry—perfect

  John Durso Keller Williams Realty Partner

  18 Grove St, Highland, NY 12528
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  /18

  $165,000 Sold Jun 25, 2025

  274 Swartekill Rd, Highland, NY 12528

  • Land
  • 12.81 Acres
  • $12,881 per Acre

  Last Sold Summary

  • 6% Below List Price
  • 98 Days On Market

  Current Estimated Value $164,918

  Last Listing Agent Brian Cafferty Halter Associates Realty

  274 Swartekill Rd, Highland, NY 12528
• 

  Est $575,988 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,385 Sq Ft

  29 Glen Rock Cir, Highland, NY 12528

  29 Glen Rock Cir, Highland, NY 12528
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  /7

  $399,900

  • 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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  /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 $352,603

  Last Listing Agent Dawn Passante Coldwell Banker Village GreenN

  26 Toc Dr, Highland, NY 12528
• 

  Est $525,746 Not Listed For Sale

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

  272 Fosler Rd, Highland, NY 12528

  272 Fosler Rd, Highland, NY 12528

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