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

  (845) 524-9107

  Lot 57.1 Yulan-Barryville Rd, Highland, NY 12791
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  /36

  $1,600 - $1,900 per month

  Discover Peaceful Living at Black Creek Apartments

  1 - 2 Beds

  30 Black Creek Rd, Highland, NY 12528

  Experience a new chapter in refined living at 30 Black Creek Apartments, nestled in the peaceful beauty of Esopus, New York. Now under new ownership and professional management, this reimagined community is committed to delivering exceptional service and an elevated living experience.Set against the backdrop of the Hudson Valley’s natural charm, 30 Black Creek offers charming and peaceful

  30 Black Creek Rd, Highland, NY 12528
• 

  $434,000 Sold Nov 26, 2025

  • 1,934 Sq Ft
  • $224/SF
  • 29 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1959

  4 Salk Dr, Highland, NY 12528

  Welcome Home to Comfort, Style & Mountain ViewsThis beautifully renovated split-level home is tucked away in a well-kept neighborhood, offering picturesque mountain views from the front elevation. With flexible living space, modern updates, and inviting outdoor areas, it’s ready for you to move right in.Inside, you’ll find 3 plus bedrooms (including a flexible bonus space) and two full

  Barbara Korabel Four Seasons Realty Group

  4 Salk Dr, Highland, NY 12528
• 

  Est $372,648 Not Listed For Sale

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

  64 Argent Dr, Highland, NY 12528

  64 Argent Dr, Highland, NY 12528
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  /22

  $850,000 Pending

  • 5 Beds
  • 4 Baths
  • 3,230 Sq Ft

  7 Elliotts Ln, Highland, NY 12528

  Welcome to 7 Elliotts Ln, where space, comfort, and flexibility all come together—right in the heart of New Paltz. Set on a full acre, this 5-bedroom, 4-bath home offers over 3,200 square feet of living space, including a legal accessory apartment that's ideal for guests, extended living, or additional rental income. Step inside and you'll find beautifully new hardwood floors that run throughout

  

  Donna Brooks

  Compass Greater NY, LLC

  (845) 250-6194

  7 Elliotts Ln, Highland, NY 12528
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  /4

  $925 per month

  • 1 Bath
  • 130 Sq Ft
  • Apartment for Rent

  200 Fosler Rd Unit 22, Highland, NY 12528

  Small room for rent located within the Marlboro school district!Quiet area but with plenty of neighbors. Shared laundry on site. Located on an old catering site. Full application is needed including background & credit check. All utilities included except WiFi

  Angela Kadian Stonewall Realty Group LLC

  200 Fosler Rd Unit 22, Highland, NY 12528
• 

  $222,000 Sold Nov 24, 2025

  • 762 Sq Ft
  • $291/SF
  • 56 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1960

  534 New Paltz Rd, Highland, NY 12528

  Welcome to 534 New Paltz Rd, Lloyd, NY — a fully renovated and fully furnished home designed for modern living and investment potential. Every detail has been upgraded: New Septic System, New Roof, New Electrical, New plumbing, New Well Pump, New Pressure Tank, New Water Filter, New Water Heater, New Windows, New Heaters, New Doors, New Sump Pump, New Kitchen, New Bathroom Vanity, New Flooring,

  Jonathan Minerick HomeCoin.com

  534 New Paltz Rd, Highland, NY 12528
• 

  Est $578,715 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,478 Sq Ft

  288 Baileys Gap Rd, Highland, NY 12528

  288 Baileys Gap Rd, Highland, NY 12528
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  /27

  $585,000 Pending

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

  660 N Chodikee Lake Rd, Highland, NY 12528

  Spacious, secluded and close to New Paltz: This roomy ranch features key technical updates while retaining its bright 1970s vibe. Privately set at the end of a long driveway flanked on each side by stacked-bluestone walls, the house sits at the center of the historic Stonewall Farm on its own 19 wooded acres. Entered through a pergola-topped courtyard into a symmetrical blue-stoned foyer gallery,

  

  Hayes Clement

  Compass Greater New York, LLC

  (845) 327-2488

  660 N Chodikee Lake Rd, Highland, NY 12528
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  /50

  $3,039 - $16,313 per month

  Vineyard Commons

  2 - 3 Beds

  6142 Merlot Dr, Highland, NY 12528

  55+ LIVING IN THE HEART OF HUDSON VALLEYVineyard Commons offers a fresh approach to active adult living, combining comfort, convenience and style. Our spacious two and three bedroom apartments feature vaulted ceilings, abundant closet space and gourmet kitchens with granite countertops and stainless steel appliances, all on a single level for effortless living. Enjoy the freedom to do as

  6142 Merlot Dr, Highland, NY 12528
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  $327,000 Sold Nov 20, 2025

  • 1,816 Sq Ft
  • $180/SF
  • 74 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1900

  283 Hawleys Corners Rd, Highland, NY 12528

  Nestled on a quiet country road in Highland, this inviting old-style home offers peaceful living on a cleared, and leveled, one-acre lot. Surrounded by nature, the property blends timeless charm with essential exterior modern updates. Including durable new siding, a freshly built deck perfect for relaxing or entertaining, a new roof, and updated gutters—ensuring years of worry-free enjoyment.

  Dawn Passante Coldwell Banker Village Green

  283 Hawleys Corners Rd, Highland, NY 12528
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  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,768 Sq Ft

  32 Timber Lake Dr, Highland, NY 12792

  32 Timber Lake Dr, Highland, NY 12792
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  /33

  $639,000 Pending

  • 4 Beds
  • 1.5 Baths
  • 2,244 Sq Ft

  668 N Chodikee Lake Rd, Highland, NY 12528

  Welcome to Stonewall Farm, a rare 20-acre retreat featuring a charming 19th Century stone house and outbuilding 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 plus its signature foursquare stone farm house built

  

  Hayes Clement

  Compass Greater New York, LLC

  (845) 599-7908

  668 N Chodikee Lake Rd, Highland, NY 12528
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  /7

  $1,350 per month

  • 1 Bath
  • 300 Sq Ft
  • Apartment for Rent

  200 Fosler Rd Unit 49, Highland, NY 12528

  Small studio cottage located within the Marlboro school district!Quiet area but with plenty of neighbors. All utilities included tenant pays for wifi otherwise. Full application is needed including background & credit check. These are motel like set ups, it is located on an old catering site.

  Angela Kadian Stonewall Realty Group LLC

  200 Fosler Rd Unit 49, Highland, NY 12528
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  /24

  $350,000 Sold Nov 20, 2025

  • 1,524 Sq Ft
  • $230/SF
  • 93 Days On Market

  • 4 Beds
  • 1 Bath
  • Built 1950

  153 Upper Grand St, Highland, NY 12528

  Charming Cape Cod home ideally located outside the downtown of Highland is waiting for it's new owners! This quaint home is centrally located minutes from both NYS Thruway as well as Metro-North Railways, making commuting to work a breeze and is conveniently situated near local shops, restaurants, breweries/wineries, the Walkway Over the Hudson, and all that the vibrant areas that the Hudson

  John Quinn Quinn Realty Group Inc.

  153 Upper Grand St, Highland, NY 12528
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  Est $561,205 Not Listed For Sale

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

  274 Fosler Rd, Highland, NY 12528

  274 Fosler Rd, Highland, NY 12528
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  /21

  $369,000 Under Contract

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

  38 Roxanne Blvd, Highland, NY 12528

  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 of New Paltz or Poughkeepsie Bridge.

  

  Amy Hawks

  Berardi Realty

  (845) 203-3694

  38 Roxanne Blvd, Highland, NY 12528
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  /35

  $1,695 - $1,850 per month

  Brookside Apartments

  1 - 2 Beds

  210 Vineyard Ave, Highland, NY 12528

  Located minutes from the Mid-Hudson Bridge, 4 miles from Vassar Hospital. Quiet brookside location. One mile from the quaint shops in the town of Highland.

  210 Vineyard Ave, Highland, NY 12528
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  $375,000 Sold Nov 18, 2025

  • 1,050 Sq Ft
  • $357/SF
  • 22 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1930

  27 Amato Ln, Highland, NY 12528

  Tucked away on a peaceful dead-end road in Highland, this inviting 2-bedroom, 1-bath home offers the perfect blend of charm, updates, and convenience. Whether you're searching for a starter home or a weekend retreat, this property checks all the boxes. The main level welcomes you with an open layout, rustic exposed beams, and a stylishly renovated kitchen featuring sleek soapstone countertops.

  Jacob Cohen eXp Realty

  27 Amato Ln, Highland, NY 12528
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  Est $621,475 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,214 Sq Ft

  321 Perkinsville Rd, Highland, NY 12528

  321 Perkinsville Rd, 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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  /4

  $1,400 per month

  • 1 Bath
  • 400 Sq Ft
  • Apartment for Rent

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

  Very pretty and spacious studio apartment. Located 5 miles to New Paltz and 5 miles to Poughkeepsie and Metro North. Modern and beautifully renovated. Water/Sewer, lawn care, trash removal and snow removal. Call for pet approval. Off street parking in a lot. Many amenities located in this area.

  Pamela Di Martino Curasi Realty, Inc.

  70 New Paltz Rd Unit 2A, Highland, NY 12528
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  $50,000 Sold Nov 17, 2025

  • Land
  • 7.33 Acres
  • $6,821 per Acre

  • 154 Days On Market

  0 Yulan-Barryville Rd Unit KEY857000, Highland, NY 12719

  Discover 7.33 acres of serene, wooded land in Barryville, NY—an ideal setting for outdoor lovers and nature seekers. This private lot offers endless possibilities, whether you're planning a weekend retreat, future cabin, or long-term investment. Surrounded by the natural beauty of the Catskills, you’ll enjoy peace, privacy, and abundant wildlife right from your own property. Located near state

  Loretta Wolff NexLvl Real Estate Inc.

  0 Yulan-Barryville Rd Unit KEY857000, Highland, NY 12719
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  Est $591,476 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,100 Sq Ft

  94 Glen Rock Cir, Highland, NY 12528

  94 Glen Rock Cir, Highland, NY 12528
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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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  /24

  $2,500 per month

  Hudson Place

  2 Beds

  1300 Hudson Place, Highland, NY 12528

  Welcome to Hudson Place, where your dream lifestyle becomes a reality. This community offers more than just a place to live - it provides a true sense of belonging and convenience featuring an onsite gym, community room and BBQ area. One of the crowning jewels of this location is its proximity to the Walkway Over the Hudson. Take leisurely strolls or invigorating jogs while relishing the scenic

  1300 Hudson Place, Highland, NY 12528
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  $425,000 Sold Nov 17, 2025

  • 1,365 Sq Ft
  • $311/SF
  • 105 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1900

  59 South St, Highland, NY 12528

  Charming 1900 Two-Story Farmhouse with Vintage Character... Step into timeless charm with this lovingly cared for two-story farmhouse, built circa 1900 and brimming with original character. Featuring authentic hardwood floors, this 2-bedroom home offers cozy living spaces, walk-in closets, and a woodstove perfect for those crisp Hudson Valley evenings. Enjoy peaceful mornings on the classic

  jeff farnell John J Lease REALTORS Inc

  59 South St, Highland, NY 12528
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  /17

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,080 Sq Ft

  119 Tuckers Corners Rd, Highland, NY 12528

  119 Tuckers Corners Rd, 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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  /11

  $2,400 per month

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

  596 Milton Turnpike, Highland, NY 12528

  Escape the hustle and bustle of city life with this cozy 2-bedroom rental, nestled in the heart of serene countryside. Perfectly blending rustic charm and modern convenience, this home offers the ideal retreat for those seeking peace and privacy. Comfortable, bright, and inviting spaces with plenty of natural light. A cozy living room that leads into a functional kitchen, perfect for family meals

  Teri Biondo HV Premier Properties Realty

  596 Milton Turnpike, Highland, NY 12528
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  $335,000 Sold Nov 13, 2025

  • 1,396 Sq Ft
  • $240/SF
  • 90 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1988

  87 Sterling Place, Highland, NY 12528

  Welcome to 87 Sterling Place in Highland, located right over the Mid Hudson Bridge. The home features 2 spacious rooms and a loft for a possible office or guest space. There is an attached 1 car garage perfect for sheltering you from the elements outside. Go shopping at Hannafords right next door and pull into your garage to unload the car – no more being out in the rain and snow unloading your

  Mark Snyder eXp Realty

  87 Sterling Place, Highland, NY 12528
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  Est $461,089 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,672 Sq Ft

  625 Milton Turnpike, Highland, NY 12528

  625 Milton Turnpike, 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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  /15

  $2,200 - $2,250 per month

  Orchard Hills

  2 Beds

  Orchard Hill Cir, Highland, NY 12528

  Explore the ideal sanctuary in Highland, New York! This vibrant community boasts a mix of 2 and 3 bedroom townhouses and 1 bedroom studios. Revel in the convenient proximity to local boutiques, dining establishments, and the full spectrum of Highland's amenities. Furthermore, the nearby rail trail beckons outdoor enthusiasts and nature admirers, creating an exceptional refuge for strolls, jogs,

  Orchard Hill Cir, Highland, NY 12528
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  $319,000 Sold Nov 12, 2025

  • 1,220 Sq Ft
  • $261/SF
  • 45 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1976

  38 Sunny Brook Cir, Highland, NY 12528

  Move-In Ready 3 Bedroom Townhouse in Highpoint! Move right into this beautifully updated 3-bedroom townhouse featuring a brand-new kitchen with quartz counters, tiled floors and stainless appliances, new flooring, and fresh carpeting throughout. Enjoy spacious rooms with a comfortable layout perfect for everyday living. Located in a welcoming community with fantastic amenities including a pool

  Naomi Streicher Q Home Sales

  38 Sunny Brook Cir, Highland, NY 12528
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  /35

  Est $615,397 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,650 Sq Ft

  135 Chapel Hill Rd, Highland, NY 12528

  135 Chapel Hill Rd, 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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  /16

  $2,000 per month

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

  698 South St Unit 2, Highland, NY 12528

  New floors are on the way, be in by the holidays! The eat in kitchen, living room & half bath start off the 1st floor of this middle unit condo, which also offers two 2nd floor bedrooms, a full bath with/tub & plenty of closet space. The washer and dryer hook ups are located in your full basement. Rental includes trash removal, lawn maintenance & snow removal~ except your porches and steps.

  Michele Spignardo Keller Williams Hudson Valley

  698 South St Unit 2, Highland, NY 12528
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  $386,000 Sold Nov 07, 2025

  • 1,808 Sq Ft
  • $213/SF
  • 25 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1989

  2 Cambridge Ct, Highland, NY 12528

  Offering a beautifully maintained 3-bedroom, 2.5-bathroom townhouse with garage in a highly sought-after neighborhood! Nestled in a quiet, well-kept community, this spacious home offers a perfect blend of convenience and comfort. The bright and airy layout features an updated kitchen with modern finishes, perfect for everyday living or entertaining guests. Enjoy natural light throughout the home,

  Christopher Baker River to Ridge Rlty Associates

  2 Cambridge Ct, Highland, NY 12528
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  Est $225,500 Not Listed For Sale

  9 Elbow Ln, Highland, NY 12528

  9 Elbow Ln, Highland, NY 12528

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