Highland, NY Homes for Sale

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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

  (845) 524-9107

  Lot 57.1 Yulan-Barryville Rd, Highland, NY 12791
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  /46

  $569,000

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

  93 Glen Rock Cir, Highland, NY 12528

  Move in Colonial shows pride of ownership. Set beautifully on 1.4 acres this 4 bedroom 2.5 bath stunner boasts modern kitchen with granite countertops custom cabinets and center island. It's open floorplan great room gives ample room for kitchen dining or cozying around the gas fireplace. For more formal dining there is a dining room. The entire first floor has equisite hardwood flooring From

  

  Randy Spiesman

  Weichert REALTORS

  (845) 413-2225

  93 Glen Rock Cir, Highland, NY 12528
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  /18

  $59,900

  • Land
  • 6.09 Acres
  • $9,836 per Acre

  Lot 28 Summit Dr, Highland, NY 12792

  Beautiful 6+/- acres in gated community! This peaceful property is a nice corner parcel with a lot of road frontage that is mostly level and wooded. This is a great place to build your dream home with lake rights to Timber Lake Estates. Close to Eldred, Barryville and the Delaware River. Come take a look at this property before it's gone!

  

  Dawn Curreri

  Eagle Valley Realty

  (845) 412-9934

  Lot 28 Summit Dr, Highland, NY 12792
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  /16

  $159,000

  • Land
  • 5.05 Acres
  • $31,485 per Acre

  Lot 1 Zane Grey Way, Highland, NY 12719

  Fantastic opportunity to own a prime, buildable property with access to beautiful York Lake. Located in the exclusive private community of York Lake Shores, York Lake is a pristine 103-acre, natural, non-motor boat, spring-fed lake that is only accessible to residents within the two communities that surround it. This lovely 5.05 acre lot is as close as one can be to the community’s lake access

  

  Edward Rabon

  Compass Greater NY, LLC

  (845) 448-8745

  Lot 1 Zane Grey Way, Highland, NY 12719
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  /19

  $369,000

  • 3 Beds
  • 2.5 Baths
  • 1,707 Sq Ft

  38 Roxanne Blvd, Highland, NY 12528

  A/O 9/27/2025 (no available showings at this time) Opportunity knocks with this three bedroom, two bathroom split ranch situated on one acre, on a quiet cul-de-sac road. Beautiful hardwood floors and desirable floor plan. Bring your vision as this home is full of potential! The lower level walkout area of the home is finished with a full bathroom. Conveniently located just minutes to the Village

  

  Amy Hawks

  Berardi Realty

  (845) 203-3694

  38 Roxanne Blvd, Highland, NY 12528
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  /50

  $1,175,000

  • 7 Beds
  • 5 Baths
  • 5,730 Sq Ft

  660 N Chodikee Lake Rd, Highland, NY 12528

  ACCEPTED OFFERS ON BOTH HOUSES AS OF SEPT 17, 2025. Welcome to Stonewall Farm, a rare 40-acre retreat featuring not one but TWO architecturally distinctive houses less than two hours from Manhattan and minutes from the New Paltz village center. Privately set at the end of a long driveway flanked on each side by its namesake stacked-bluestone walls, the property features both meadows and woods.

  

  Hayes Clement

  Compass Greater NY, LLC

  (845) 378-9916

  660 N Chodikee Lake Rd, Highland, NY 12528
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  /2

  $185,000

  • Land
  • 0.24 Acre
  • $770,833 per Acre

  224 Vineyard Ave, Highland, NY 12528

  Recent home demolished and removed. .24 acre lot with town water and sewer (Natural gas on the street but not to the lot). 1.5 miles to the Hamlet of Highland. Ask us about our custom home affordability program.

  

  Danielle Carlson-murphy

  Start Home Smart, Inc.

  (845) 713-8132

  224 Vineyard Ave, Highland, NY 12528
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  /25

  $365,000

  • 2 Beds
  • 2 Baths
  • 1,300 Sq Ft

  241 Upper Rd N, Highland, NY 12528

  Welcome to 241 Upper North Road - Where Comfort Meets Convenience! This beautifully maintained modern double-wide mobile home offers the charm and functionality of a modular home, nestled on a spacious 0.78-acre lot. With an inviting open floor plan, this residence features 2 bedrooms, a versatile den with a cozy gas fireplace, and 2 full bathrooms, offering ample space for both relaxation and

  

  Isabel Alves

  RE/MAX Town & Country

  (845) 493-3607

  241 Upper Rd N, Highland, NY 12528
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  /8

  $195,000

  • Land
  • 22.3 Acres
  • $8,744 per Acre

  0 Crawford Rd Unit KEY821449, Highland, NY 12528

  Beautiful wooded 22.3 acre parcel along quaint Crawford Road just outside of the charming Delaware river hamlet of Barryville. Close to Eldred, Yulan and the Delaware River.

  

  Rosemarie DeCristofaro

  Callicoon Real Estate LLC

  (845) 671-5361

  0 Crawford Rd Unit KEY821449, Highland, NY 12528
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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 TownThis 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,

  

  Danielle Carlson-murphy

  Start Home Smart, Inc.

  (845) 581-7956

  224 Vineyard Ave, Highland, NY 12528
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  /65

  $1,500,000

  • 3 Beds
  • 3.5 Baths
  • 4,572 Sq Ft

  74 Bellevue Rd, Highland, NY 12528

  Hudson River Views! This inviting home combines comfort, character, and convenience with a dramatic two-story foyer and open floor plan. Enjoy a cozy living room with a gas fireplace, formal dining area overlooking the river, and a kitchen with custom cherry cabinets, granite counters, and Jenn Air cooktop. A flexible room with French doors makes a great office or fourth bedroom. Bathroom and

  Hollis Dukler Coldwell Banker Village GreenN

  74 Bellevue Rd, Highland, NY 12528
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  /31

  $450,000

  • 4 Beds
  • 2 Baths
  • 1,428 Sq Ft

  10 Carly Dr, Highland, NY 12528

  Discover the perfect blend of comfort, convenience, and lifestyle in this beautifully maintained 4-bedroom, 2-bathroom single-level home, tucked away in a peaceful cul-de-sac in sought-after Highland, NY. Sitting on a full acre, this property offers endless possibilities space to entertain, relax, and enjoy outdoor living. Cool off all summer long in the above-ground pool, or take in the privacy

  Megan Krusen eXp Realty

  10 Carly Dr, Highland, NY 12528
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  /36

  $565,000

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

  5 Willow Dock Rd, Highland, NY 12528

  A truly special home that seamlessly blends the charm of its century-old origins with modern-day comfort and design. Tucked away on a quiet dead-end road, it offers sweeping Hudson River views from nearly every room, inviting you to experience the river’s beauty through all four seasons. Just steps from the water’s edge, this historic treasure provides a front-row seat to breathtaking sunrises

  Lindsay Rothman Compass Greater NY LLC

  5 Willow Dock Rd, Highland, NY 12528
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  /26

  $599,000

  • 4 Beds
  • 2 Baths
  • 2,510 Sq Ft

  340 Vineyard Ave, Highland, NY 12528

  Step back in time with this spacious Victorian home full of original charm and character. Nestled on 41.10 acres of scenic land with mountain views. This property features a detached barn, 2 car garage and a classic summer kitchen. This property offers endless potential for restoration or creative retreat spaces. Inside you will find hardwood floors, birch cabinets with amazing stainless

  Ronnie Rebis Grist Mill Real Estate

  340 Vineyard Ave, Highland, NY 12528
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  /24

  $575,000

  • 3 Beds
  • 1 Bath
  • 2,086 Sq Ft

  269 Orchard Rd, Highland, NY 12528

  Nestled among scenic orchards is this beautiful, updated nineteenth century farm house situated on almost 20 acres of beautiful pasture land and woods. This charming 3 bedroom home has a lovely full bath and plenty of living space for both humans and horses alike. The current owner keeps her horses on the property which is equipped with 2 run-in sheds and 7 shed row stalls which all have power

  Daniel Balassone VYLLA Home

  269 Orchard Rd, Highland, NY 12528
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  /33

  $499,900

  • 4 Beds
  • 2 Baths
  • 2,640 Sq Ft

  98 North Rd, Highland, NY 12528

  This charming 1900 farmhouse in Highland, New York, offers a comfortable and spacious living space with original wide custom moldings and beautiful oak hardwood flooring. Enjoy the beautiful sunlight in the fully finished sunroom. The kitchen is open with plenty of counter space and new appliances. Large dining area. The primary bedroom is on the first floor with windows facing three sides. enjoy

  Dawn Passante Coldwell Banker Village GreenN

  98 North Rd, Highland, NY 12528
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  /44

  $869,000

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

  1 Janine Place, Highland, NY 12528

  Just 90 minutes from New York City, this extraordinary turnkey farmhouse has been completely reimagined with meticulous attention to detail, blending timeless Hudson Valley charm with modern luxury living. Step inside to soaring ceilings, wide-plank wood floors, and sunlit spaces that flow effortlessly. At the heart of the home, the custom chef's kitchen features a gas range, quartz countertops,

  Lindsay Stevens eXp Realty

  1 Janine Place, Highland, NY 12528
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  /48

  $509,900

  • 3 Beds
  • 3 Baths
  • 1,824 Sq Ft

  62 Clearwater Rd, Highland, NY 12528

  Discover unparalleled privacy in this beautifully maintained home, set on its own serene acreage. Step inside to find a warm and inviting interior featuring hardwood floors throughout the main living areas and plush carpet in the bedrooms for comfort. The living room is anchored by a gorgeous stone fireplace, creating the perfect gathering spot for cozy evenings or entertaining guests. The

  Patricia Lucey Picture It Sold, LLC

  62 Clearwater Rd, Highland, NY 12528
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  /21

  $450,000

  • 4 Beds
  • 2 Baths
  • 2,266 Sq Ft

  12 Woodside Place, Highland, NY 12528

  Come see this home that offers a perfect combination of charm, convenience, and community. This beautiful 4-bedroom, 2-bath home is full of character, featuring original hardwood floors and elegant French doors. The spacious living and dining areas are ideal for family gatherings, while the kitchen boasts stunning granite countertops, perfect for cooking and entertaining. Enjoy peaceful mornings

  Geraldine Gaudioso Century 21 Alliance-NP

  12 Woodside Place, 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 river-town condominium building with direct access to the Hudson Valley Rail Trail in the heart of Highland, NY. 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

  Vitaly Isaacs Magic Of Great Neck Realty Inc

  128 Vineyard Ave Unit 207, Highland, NY 12528
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  /11

  $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, NY. 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

  Vitaly Isaacs Magic Of Great Neck Realty Inc

  128 Vineyard Ave Unit 206, Highland, NY 12528
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  /11

  $340,000

  • 2 Beds
  • 1 Bath
  • 1,122 Sq Ft

  128 Vineyard Ave Unit 210, 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, NY. 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

  Vitaly Isaacs Magic Of Great Neck Realty Inc

  128 Vineyard Ave Unit 210, Highland, NY 12528
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  /11

  $265,000

  • 1 Bed
  • 1 Bath
  • 730 Sq Ft

  128 Vineyard Ave Unit 205, 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, NY. 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

  Vitaly Isaacs Magic Of Great Neck Realty Inc

  128 Vineyard Ave Unit 205, Highland, NY 12528
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  /11

  $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, NY. 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

  Vitaly Isaacs Magic Of Great Neck Realty Inc

  128 Vineyard Ave Unit 106, Highland, NY 12528
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  /12

  $270,000

  • 1 Bed
  • 1 Bath
  • 803 Sq Ft

  128 Vineyard Ave Unit 104, 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, NY. 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

  Vitaly Isaacs Magic Of Great Neck Realty Inc

  128 Vineyard Ave Unit 104, Highland, NY 12528
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  /6

  $199,900

  • Land
  • 11 Acres
  • $18,173 per Acre

  TBD Hawleys Corners Rd, Highland, NY 12528

  11 acres offering privacy and potential. The land is ideal for building a secluded estate, nature retreat located on a country road yet close to Route 299 leading to NYS Thruway. Mid Hudson Bridge 5 miles away. The parcels break down as follows:Parcel 1: 3.5 acresParcel 2: 4 acresParcel 3: 3.7 acresKey Features:Peaceful rural setting with minimal trafficSurrounded by woods

  Dawn Passante Coldwell Banker Village GreenN

  TBD Hawleys Corners Rd, Highland, NY 12528
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  /6

  $44,000

  • Land
  • 2.9 Acres
  • $15,172 per Acre

  TBD Hawleys Corners Rd, Highland, NY 12528

  This property is located in a desirable area that offers a balance of privacy and convenient access to key attractions in the Hudson Valley. Its location is situated just a few miles from the heart of downtown New Paltz and with Kingston also close by, you'll have easy access to all the vibrant shops, restaurants, and cultural scene. The site is also 6 miles from the Mid-Hudson Bridge and the

  Dominick Martorana Century 21 Alliance Rlty Group

  TBD Hawleys Corners Rd, Highland, NY 12528
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  /32

  $365,000

  • 2 Beds
  • 2.5 Baths
  • 2,086 Sq Ft

  222 Sterling Place, Highland, NY 12528

  Welcome to this exceptional townhouse in a highly desirable community—spacious, thoughtfully updated, and filled with features you won’t easily find elsewhere.The first level offers a bright eat-in kitchen that opens into a combined dining and living area, creating a warm, connected space perfect for everyday living and entertaining.Upstairs, the second floor hosts a primary bedroom, a

  Dawn Passante Coldwell Banker Village Green

  222 Sterling Place, Highland, NY 12528
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  /23

  $295,000

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

  48 Sunny Brook Cir, Highland, NY 12528

  Welcome to 48 Sunny Brook Circle, where easy living meets effortless style. This sun-drenched, single-level end unit offers 1,056 square feet of comfort and charm, designed for those who crave simplicity without compromise. Step inside and you'll find a bright, open layout featuring a spacious eat-in kitchen, a welcoming living room, a private primary suite, and a versatile converted den (legal

  Leigh Wagner-Quintana Keller Williams Hudson Valley

  48 Sunny Brook Cir, Highland, NY 12528
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  /17

  $245,000

  • 2 Beds
  • 2 Baths
  • 1,456 Sq Ft

  16 Trout Brook Ln, Highland, NY 12528

  Beautiful Hudson Valley location encompassed by apple orchards, farms, colleges, yet still close to trains and airports. Immaculate 2017 1456 sq. ft. manufactured home includes central air, forced hot air propane heat, stainless steel appliances, front and side porches, and large shed with electric. Upgrades include custom walk-in closet, Rapid Wall insulated skirting with side access door, vinyl

  Lisa Cozzolino Cronin & Company Real Estate

  16 Trout Brook Ln, Highland, NY 12528
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  /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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  /14

  $135,000

  • 2 Beds
  • 1 Bath
  • 552 Sq Ft

  407 Swartekill Rd, Highland, NY 12528

  Charming 2-Bedroom Mobile Home on 1.29 Acres in Swartekill Neighborhood Discover the potential of this cozy 2-bedroom, 1-bathroom mobile home nestled on a spacious 1.29-acre lot in the desirable Swartekill neighborhood, located in the Town of Esopus and within the sought-after New Paltz School District. This property offers a unique opportunity for those looking to invest, renovate, or create

  Kristen Zigouras eXp Realty

  407 Swartekill Rd, Highland, NY 12528
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  /31

  $399,000

  • 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. A full attic

  Sally Sprogis Four Seasons Sotheby's Int'l R

  534 U S 44, Highland, NY 12528
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  /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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  /44

  $1,299,000

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

  243 Hawleys Corners Rd, Highland, NY 12528

  Discover the perfect blend of craftsmanship, comfort and opportunity in this stunning custom-built Craftsman home, offering over 3,000 square feet of living space on 20 picturesque acres. Previously subdivided with six additional parcels, this property offers exceptional potential for expansion, development or a private gathering retreat. Inside, you will find cathedral ceilings, custom woodwork,

  Melissa Pettinella Century 21 Alliance Realty Grp

  243 Hawleys Corners Rd, Highland, NY 12528
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  /47

  $389,000

  • 4 Beds
  • 1.5 Baths
  • 1,458 Sq Ft

  22 Washington Ave, Highland, NY 12528

  Lovely home within walking distance to center Village Highland & Walkway Over the Hudson Bridge. 3BR/1.5BA home located at the end of quiet Cul de Sac with private backyard. Beautiful front porch up front and a rustic 2 story barn over looking private backyard with stream and forest. Enjoy the coziness and charm of this lovingly cared for home built in 1840. Detached 2 car garage with small paved

  CAROL MC RITCHIE Thomas Zengen

  22 Washington Ave, Highland, NY 12528
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  /33

  $399,900

  • 4 Beds
  • 3 Baths
  • 1,728 Sq Ft

  6 Smith Terrace, Highland, NY 12528

  Welcome to this beautifully updated four-bedroom, three-bath contemporary ranch which includes a rentable 1 bedroom accessory apartment in Highland, Ulster County. With over 1,700 square feet of living space on a third of an acre, this home offers a thoughtful blend of style, function, income potential and flexibility. Inside, the open layout highlights hardwood and tile flooring, exposed

  Virginia Corbett eXp Realty

  6 Smith Terrace, Highland, NY 12528
• 

  

  /10

  $110,000

  • Land
  • 2.1 Acres
  • $52,381 per Acre

  748 State Route 44 55, Highland, NY 12528

  Discover the perfect canvas for your vision on this expansive 2.1-acre parcel—fully surveyed and complete with a percolation test–approved septic system, offering clarity and confidence as you plan your future home or weekend escape. Tucked along a quiet, picturesque country road, this property delivers the ideal blend of privacy, nature, and accessibility. Its prime location places you just

  Ashley Olson Minard eXp Realty

  748 State Route 44 55, Highland, NY 12528
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  /39

  $1,195,000

  • 4 Beds
  • 3.5 Baths
  • 2,240 Sq Ft

  520 Plutarch Rd, Highland, NY 12528

  Modern Artisan Home on 5 Serene Acres Welcome to this reimagined modern retreat (+ New Paltz schools!), where every detail reflects a local artisan's vision and the signature craftsmanship of Lake North Designs. The exterior's mix of textures creates a bold architectural statement, while stone walls—sourced directly from the property—add grounding authenticity inside and out. The entryway makes a

  Bree Chambers Compass Greater NY, LLC

  520 Plutarch Rd, Highland, NY 12528
• 

  

  /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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