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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  /13

  $189,000

  • Land
  • 5 Acres
  • $37,426 per Acre

  Lot 1 Zane Grey Way, Highland, NY 12719

  Fantastic opportunity to own a prime, buildable lake access property in Sullivan County’s beautiful York Lake in the exclusive, private community of York Lake Shores. York Lake is a 103-acre pristine, natural, non-motor boat, spring-fed lake that is only accessible to residents within the two communities that surround it. While not lakefront, this 5.05 acre lot is the closest one can be

  

  Edward Rabon

  Century 21 Geba Realty

  (845) 622-8776

  Lot 1 Zane Grey Way, Highland, NY 12719
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  /7

  $195,000

  • Land
  • 22 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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  /15

  $239,900

  • 1 Bed
  • 1 Bath
  • 762 Sq Ft

  534 New Paltz Rd, Highland, NY 12528

  Move-in Ready Gem-Perfect for Easy Living in Highland, NYStep into this completely renovated 1-Bedroom, 1-Bath home designed for comfort and convenience. The entire house has been fully renovated featuring New Septic System, New Roof, New Electrical, New Plumbing, New Washer/Dryer hook up, New water heater, New Electrical panel 200 amp, New Sheetrock, New wall and ceiling insulation, New

  Sandra Rosario Hello Dolly Real Estate

  534 New Paltz Rd, Highland, NY 12528
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  /19

  $469,000

  • 3 Beds
  • 3 Baths
  • 1,656 Sq Ft

  12 Summit Dr, Highland, NY 12792

  Escape to your own private sanctuary! This stunning retreat sits on 5.5 acres of pristine woodland within the exclusive gated community of Timber Lake Estates. Paved roads wind through the community, leading you around the sparkling centerpiece - Timber Lake itself.Four seasons of recreation await right outside your door. Summer brings endless lake adventures: fishing from the shore,

  Joann Alvis Coldwell Banker Village GreenN

  12 Summit Dr, Highland, NY 12792
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  /21

  $475,000

  • 4 Beds
  • 2 Baths
  • 1 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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  /36

  $575,000

  • 3 Beds
  • 2.5 Baths
  • 2,242 Sq Ft

  17 Dogwood Knolls, Highland, NY 12528

  Incredible home with stunning renovations; this one of a kind raised ranch has over 2,200 sq.ft. featuring 3/4 bedrooms two and a half baths, PLUS bonus room and 2 car garage. Located in a peaceful setting of 3.3 private acres on the dead-end road; you get the "best of both worlds" a residential neighborhood that's also easily accessible to main roads, shopping and restaurants! This home has

  Gzim Hakanjin Coldwell Banker Realty

  17 Dogwood Knolls, Highland, NY 12528
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  /40

  $475,000

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

  224 Martin Ave, Highland, NY 12528

  Welcome to this charming ranch style home featuring 3 cozy bedrooms. The primary bedroom has a large full bath, perfect for comfortable living. As you step inside you will be greeted by beautiful wood floors that flow seamlessly throughout the living spaces. The spacious kitchen boasts a charming breakfast area with sliders leading to the stone patio, making it the ideal spot for casual dining or

  Dawn Passante Coldwell Banker Village GreenN

  224 Martin Ave, Highland, NY 12528
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  /49

  $550,000

  • 3 Beds
  • 1.5 Baths
  • 1,092 Sq Ft

  13 Sharon Dr, Highland, NY 12528

  Beautiful Ranch totally renovated ,new roof 2025 ,new siding 2025.Offer 3 bath and 1.5 Bath .Welcome to this charming ranch style home featuring 3 cozy bedrooms. As you step inside you will be greeted by beautiful commerce floors that flow seamlessly throughout the living spaces. The spacious kitchen boasts a charming breakfast area with sliders leading to the stone patio, making it the ideal

  Drita Shala Howard Hanna Rand Realty

  13 Sharon Dr, Highland, NY 12528
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  /24

  $575,000

  • 4 Beds
  • 2.5 Baths
  • 2,342 Sq Ft

  27 Salk Dr, Highland, NY 12528

  Welcome to this beautifully maintained 4-bedroom, 2.5-bath Colonial perfectly blending timeless charm with modern conveniences. Located in a great commuter location, just minutes from the Mid-Hudson Bridge and local shopping, this home offers space, comfort, and unbeatable accessibility.The inviting living room features a cozy fireplace, ideal for relaxing evenings, while the family room and

  Margaret Thorne Keller Williams Hudson Valley

  27 Salk Dr, Highland, NY 12528
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  /24

  $515,000

  • 4 Beds
  • 2.5 Baths
  • 2,184 Sq Ft

  19 Oak Crest Dr, Highland, NY 12528

  Blending comfort and style, this thoughtfully refreshed home is ready to welcome you. Major upgrades bring peace of mind, including a 50-year architectural roof (installed 2023) brand new bathrooms and beautiful new flooring throughout, including warm red oak hardwood that elevates the interior. The upstairs features all new carpeting, two fully renovated bathrooms, walk in primary closet, new

  Sandi Park Coldwell Banker Realty

  19 Oak Crest Dr, Highland, NY 12528
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  /46

  $600,000

  • 5 Beds
  • 3 Baths
  • 2,024 Sq Ft

  191 Bedell Ave, Highland, NY 12528

  Welcome to 191 Bedell Ave in Highland, a move-in ready gem blending classic charm with modern updates! This beautifully maintained home features cathedral ceilings, hardwood floors, abundant natural light, and spacious living areas perfect for relaxing or entertaining. This sprawling raised ranch includes 5 bedrooms, 3 baths, and tons of living space on 1.46 Acres! Sit back and relax in the fully

  Michael Cahill HomeSmart Homes & Estates

  191 Bedell Ave, Highland, NY 12528
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  /27

  $499,999

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  290 Tuckers Corners Rd, Highland, NY 12528

  Discover the perfect blend of comfort, convenience, and potential in this well-maintained ranch-style home, built just eight years ago and nestled on 15 subdividable, buildable acres in Highland, NY. Whether you’re a builder, investor, or simply seeking a peaceful retreat with room to expand, this property is an exceptional find. The move-in ready home features central air, a heat pump, and a

  Virginia Corbett eXp Realty

  290 Tuckers Corners Rd, Highland, NY 12528
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  /47

  $549,000

  • 3 Beds
  • 3 Baths
  • 2,102 Sq Ft

  42 Bell Dr, Highland, NY 12528

  Welcome to 42 Bell Drive, a beautifully sited, oversized Raised Ranch nestled in the magical hamlet of Highland. Perched atop a gentle hill and surrounded by mature trees, this 2,100+ square foot home offers a perfect blend of space, light, and serenity.The main level features vaulted ceilings, a fireplace, and a bright, open-concept living and dining area that flows effortlessly into a large,

  Leigh Wagner-Quintana Keller Williams Hudson Valley

  42 Bell Dr, Highland, NY 12528
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  /33

  $464,900

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

  6 Smith Terrace, Highland, NY 12528

  Discover the perfect blend of modern style, flexible living, and serene surroundings in this beautifully updated ranch-style home, ideally located in the scenic town of Highland. Offering 1,728 sq ft of thoughtfully designed space, this 4-bedroom, 3-bathroom gem includes a fully legal 1-bedroom accessory apartment—making it as functional as it is stunning.From the moment you arrive, you’ll be

  Virginia Corbett eXp Realty

  6 Smith Terrace, Highland, NY 12528
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  /15

  $330,000

  • 3 Beds
  • 1 Bath
  • 1,732 Sq Ft

  8 Van Wagner Rd, Highland, NY 12528

  Incredible open newly renovated kitchen with stainless steel appliances. Beautiful floors, An updated tiled bath with new fixtures. Spacious huge family room. Dedicated laundry room, Huge deck and so much more. Walk to the hamlet of Highland with all it's interesting shops - art gallery, florist, hair salons, custom butcher shop, candy shop, music shop, kilt maker, churches, and restaurants

  Andre Green GREEN ROSE REAL ESTATE

  8 Van Wagner Rd, Highland, NY 12528
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  /27

  $399,999

  • 2 Beds
  • 1 Bath
  • 1,050 Sq Ft

  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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  /36

  $425,000

  • 4 Beds
  • 1.5 Baths
  • 1,449 Sq Ft

  136 Chapel Hill Rd, Highland, NY 12528

  Beautifully blending timeless character with modern upgrades, this thoughtfully updated four-bedroom farmhouse offers the perfect balance of charm, comfort, and convenience. Original woodwork, wide-board flooring, and classic architectural details preserve the home's historic soul, while a series of recent renovations enhance everyday living. The fully updated kitchen and dining room are designed

  Sally Sprogis Four Seasons Sotheby's Int'l R

  136 Chapel Hill Rd, Highland, NY 12528
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  /16

  $799,000

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

  104 North Rd, Highland, NY 12528

  Come explore this once in a lifetime oppurtunity! New construction duplex/2 family home located right in Highland on North Road. Will be a great investment property, rent both sides or live in one and rent the other. Both units include 3 bedrooms, 2 1/2 baths, full unfinished basement and approximately 1550 sq. ft. This home features stone front with large windows, lots of natural light, upgraded

  Marisa Bellacicco Century 21 Alliance Rlty Group

  104 North Rd, Highland, NY 12528
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  /50

  $1,250,000

  • 14 Beds
  • 10 Baths
  • 6,406 Sq Ft

  346 Crescent Ave, Highland, NY 12528

  The Historic “Clintondale Elixir Spring House”A timeless treasure, the historic Clintondale Elixir Spring House—originally built in 1790—is a rare and remarkable offering to the market. Encompassing over 6,400 square feet of living space, this distinguished residence invites you to create your forever home amid rich character and architectural beauty.Step through the welcoming

  Artur Galustyan Century 21 Alliance Rlty Group

  346 Crescent Ave, Highland, NY 12528
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  /9

  $150,000

  • Land
  • 13 Acres
  • $11,628 per Acre

  251 Fosler Rd, Highland, NY 12528

  Ready to Go! 12.9 acres fully approved for a 4 bedroom home in the Wallkill School District. Zoned RR1.5 This level and wooded lot is engineered and recently approved with the town and DOH. Mature woodlands offer privacy and natural habitat, meandering rock walls throughout, some wetlands (see map). Very pretty lot! Close to all the area has to offer including shopping, schools, Main Street

  Michelle Genatempo Howard Hanna Rand Realty

  251 Fosler Rd, Highland, NY 12528
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  /50

  $450,000

  • 5 Beds
  • 4 Baths
  • 1,890 Sq Ft

  155 Tuckers Corners Rd, Highland, NY 12528

  Welcome to 155 Tuckers Corners Rd – a charming 1928 Craftsman Bungalow nestled on 3.37 private acres in Highland. This spacious home offers 5 bedrooms and 1.5 bathrooms in the main residence, along with a walk-out basement featuring a full in-law suite complete with its own kitchen, living room, bedroom, and full bath. Please note: the square footage does not include the finished lower-level

  Anais O'Connor Compass Greater NY, LLC

  155 Tuckers Corners Rd, Highland, NY 12528
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  /22

  $425,000

  • 2 Beds
  • 1 Bath
  • 1,365 Sq Ft

  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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  /28

  $370,000

  • 3 Beds
  • 1.5 Baths
  • 1,196 Sq Ft

  21 Clearwater Rd, Highland, NY 12528

  21 Clearwater Rd, Lloyd, NY 12528 - Updated Listing DescriptionWelcome to 21 Clearwater Rd, Lloyd, NY 12528! This beautifully maintained property offers the perfect blend of comfort and outdoor charm in the heart of the Hudson Valley. Step inside to discover hardwood floors throughout, providing a warm and inviting atmosphere. Enjoy year-round comfort with the new mini-split air conditioning

  Dustin Leibowitz eXp Realty, LLC

  21 Clearwater Rd, Highland, NY 12528
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  /6

  $300,000

  • Land
  • 6 Acres
  • $48,387 per Acre

  9 Lumen Ln, Highland, NY 12528

  Prime Development Opportunity. 6.2 acres of strategically located vacant land in Highland, NY. Zoned for General Business and packed with potential. This plot is situated just off highly traveled Route 9W. The parcel offers both visibility and accessibility, ideal for a wide range of commercial or mixed-use developments.This property has an array of permitted uses, including retail, office space,

  Theodore Chazkel BHHS HUDSON VALLEY PROP-NP

  9 Lumen Ln, Highland, NY 12528
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  /19

  $304,900

  • 4 Beds
  • 1 Bath
  • 1,574 Sq Ft

  159 Hawleys Corners Rd, Highland, NY 12528

  This charming 3-bedroom, 1-bath home on a double lot in Highland, NY, is full of potential and just waiting for the right touches to shine. One lotis .25 and the other .38 acres in size is nestled within a few miles of the scenic Hudson Valley Rail Trail and the tranquil Hudson River parks, it'sideal for outdoor enthusiasts. With a solid structure and a spacious layout, the home offers a cozy

  Jeffery Dolfinger Century21 Hudson Valley Realty

  159 Hawleys Corners Rd, Highland, NY 12528
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  /2

  $150,000

  • Land
  • 7 Acres
  • $22,388 per Acre

  0 Highland Lake Rd Unit KEY868497, Highland, NY 12732

  Located just outside of the charming hamlet of Eldred, this wooded parcel provides access to the spectacular Halfway Brook with rushing waters and waterfall along the rear property line. This area of the Hudson Valley provides easy access to the Delaware River for fishing, rafting & canoeing. It also provides plenty of opportunities for outdoor recreation, camping and hunting. It's a hop, skip

  Theresa Powers Keller Williams Realty

  0 Highland Lake Rd Unit KEY868497, Highland, NY 12732
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  /42

  $1,695,000

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

  330 Station Rd, Highland, NY 12528

  Welcome to Ridgeview Orchard Estate. Experience refined living in this exquisite new construction home, where sophisticated design meets the rugged beauty of the Shawangunk Mountain Ridge. Crafted with insulated concrete form (ICF) walls for superior energy efficiency and year-round comfort, this home is a true sanctuary of elegance and warmth. From the moment you step inside, you're welcomed by

  Danielle Bartula Howard Hanna Rand Realty

  330 Station Rd, Highland, NY 12528
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  /41

  $850,000

  • 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 gleaming new hardwood floors that run throughout most

  Donna Brooks Compass Greater New York, LLC

  7 Elliotts Ln, Highland, NY 12528
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  /36

  $769,000

  • 4 Beds
  • 2.5 Baths
  • 3,253 Sq Ft

  2 Fieldstone Ct, Highland, NY 12528

  Stunning colonial with contemporary flair gem boasts 4 large spacious bedrooms and 2.5 luxurious bathrooms, providing ample space for comfortable living. Step inside to discover a beautifully updated interior with modern finishes throughout. The 2-story living room creates an inviting space for gatherings, while the chef's kitchen features a sleek open layout, ideal for entertaining guests. Have

  Joseph Brown RE/MAX Real Property Group

  2 Fieldstone Ct, Highland, NY 12528
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  /43

  $995,000

  • 4 Beds
  • 2 Baths
  • 2,176 Sq Ft

  370 N Elting Corners Rd, Highland, NY 12528

  Tucked away on a peaceful hilltop just 7 minutes from the heart of New Paltz, this stunning 1930s Dutch Colonial has been completely reimagined—where old-world charm meets modern craftsmanship and curated design.Renovated from top to bottom by ANVO Construction with deep intentionality, this is more than a home—it’s a legacy project. Set in Highland with New Paltz schools, it offers the best of

  Lindsay Stevens eXp Realty

  370 N Elting Corners Rd, Highland, NY 12528
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  /5

  $59,000

  • Land
  • 6 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
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  /21

  $289,000

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft

  19 North Rd, Highland, NY 12528

  A/O show for backup. This completely renovated home is perfect! Starting with the front porch, where you can sit and relax, work, nap, chat, etc. and enjoy the peaceful surroundings. Enter the home on the ground floor. From the minute you walk in, you'll notice how light and bright things are. On this level the laundry room as well as a few additional finished spaces that can be used for a

  Nicole Gold RE/MAX Benchmark Realty Group

  19 North Rd, Highland, NY 12528
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  /27

  $399,900

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

  546 South St, Highland, NY 12528

  Located in the heart of the Hudson Valley, this spacious 2,500 sq ft home in Highland blends classic charm with modern upgrades—perfect for those who crave room to grow and a connection to the outdoors.The first floor features a warm and inviting living room, a large dining area ideal for gatherings, an efficient kitchen ready for your personal touch, a private laundry room, and a convenient

  Lindsay Stevens eXp Realty

  546 South St, Highland, NY 12528
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  /56

  $1,235,000

  • 7 Beds
  • 5 Baths
  • 4,630 Sq Ft

  660 N Chodikee Lake Rd, Highland, NY 12528

  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, with frontage on Chodikee Lake reached just across a

  Hayes Clement Compass Greater New York, LLC

  660 N Chodikee Lake Rd, Highland, NY 12528
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  /35

  $548,000

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

  20-22 Milton Ave, Highland, NY 12528

  Move-in ready and close to all the best amenities: This spacious two-unit Victorian in the heart of the village of Highland is just steps from popular restaurants and shops, and only minutes by car or bicycle to the Walkway Over the Hudson, New Paltz, and NYC-bound Metro-North service at Poughkeepsie. The first-floor unit features 2 bedrooms, 1 bath, a private deck, and 2 separate entrances,

  Hayes Clement Compass Greater New York, LLC

  20-22 Milton Ave, Highland, NY 12528
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  /8

  $450,000

  • Land
  • 2.04 Acres
  • $220,588 per Acre

  0 Lake View Dr Unit KEY857198, Highland, NY 12743

  Discover your dream retreat on this stunning lakefront vacant land located on Highland Lake, one of Sullivan County's premier motorboat lakes. With an established driveway and dock already in place, this property offers easy access to endless recreational opportunities, from fishing to boating to everything in between. Imagine building your perfect getaway, surrounded by breathtaking views and

  Dawn Payne Payne Team LLC

  0 Lake View Dr Unit KEY857198, Highland, NY 12743
• 

  

  /19

  $550,000

  • 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, this unique offering includes five individual parcels, presenting a blend of natural beauty, development potential, and historic charm. At the heart of the property is a c.1840s two

  Anthony DeGelormo Century 21 Alliance Rlty Group

  29 Oakes Rd, Highland, NY 12528
• 

  

  /6

  $247,000

  • Land
  • 3.90 Acres
  • $63,333 per Acre

  5 Elbow Ln, Highland, NY 12528

  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 this 9 lot sub division have been built with an eye on design and privacy.

  Elizabeth Decker Hello Dolly Real Estate

  5 Elbow Ln, Highland, NY 12528
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  /3

  $70,000

  • Land
  • 7 Acres
  • $9,550 per Acre

  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

  Kayce Drasher NexLvl Real Estate Inc.

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

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