Homes for Sale near Highland Middle School

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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

  (845) 683-5805

  19 North Rd, Highland, NY 12528
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  /15

  $225,000

  • 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
• 

  

  

  /33

  $475,000

  • 3 Beds
  • 2 Baths
  • 2,715 Sq Ft

  334 Pancake Hollow Rd, Highland, NY 12528

  With 3 bedrooms, 2 full bathrooms, and 2,715 square feet of flexible living space, this turnkey home is ready for you to move right in and make it your own.At the heart of the home is a spacious open-concept kitchen and living room — perfect for everyday living and effortless entertaining. The generously sized primary suite offers both privacy and potential, with space to add an

  Leigh Wagner-Quintana Keller Williams Realty HV Nort

  334 Pancake Hollow Rd, Highland, NY 12528
• 

  

  

  /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
• 

  

  

  /49

  $509,000

  • 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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /46

  $545,000

  • 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
• 

  

  /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

  Leigh Wagner-Quintana Keller Williams Hudson Valley

  42 Bell Dr, Highland, NY 12528
• 

  

  /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
• 

  

  /16

  $310,000

  • 2 Beds
  • 1 Bath
  • 946 Sq Ft

  329 Gregory Ct Unit 509, Highland, NY 12528

  Pictures have been virtually staged for inspiration.This fully renovated 2-bedroom condominium, which features a spacious home office, is both sophisticated and stylish. Located on the second floor, it includes a washer and dryer, as well as a terrace that overlooks lush wooded areas. The property boasts desirable amenities such as a pool, tennis courts, a clubhouse, a basketball court, a dog

  Nancy Senescu Bella NS Properties LLC

  329 Gregory Ct Unit 509, Highland, NY 12528
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  /42

  $1,275,000

  • 3 Beds
  • 2.5 Baths
  • 2,900 Sq Ft

  110 Bellevue Rd, Highland, NY 12528

  Paradise retreat with breathtaking panoramic water views of the Hudson River from every room. This impeccably renovated home has spared no expense, featuring Caesarstone throughout its generous floor plan and top-of-the-line Sub-Zero, Wolf, and Viking appliances in a dream kitchen. The open layout is perfect for entertaining or simply enjoying the stunning views as ships pass by. An abundance of

  Nancy Senescu Bella NS Properties LLC

  110 Bellevue Rd, Highland, NY 12528
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  /9

  $129,000

  • 2 Beds
  • 1 Bath
  • 1,225 Sq Ft

  69 North Rd, Highland, NY 12528

  Yup! It's a bunch of work, but it'll be the cutest house around! This is located just outside of the charming, Historic Hamlet of Highland! Driveway & garage for off street parking. Close to the Mid Hudson Bridge, the Walkway over the Hudson, New Paltz, the Thruway/87, and so much more! Hike the "Gunks" and even the Catskills are so close! Love to eat out? There are sweet restaurants

  Kathy Dawson Howard Hanna Rand Realty

  69 North Rd, Highland, NY 12528
• 

  

  /22

  $375,000

  • 2 Beds
  • 1 Bath
  • 1,090 Sq Ft

  16 Orchard Ln, Highland, NY 12528

  Welcome to your next home! This delightful 2-bedroom, 1-bath raised ranch is nestled in one of the area's most sought after neighborhoods, just minutes from local shops, restaurants, schools, and everything you need for convenient living.Step inside to find a bright and functional layout with plenty of natural light. The main level features two comfortable bedrooms and a cozy living

  Megan Krusen eXp Realty

  16 Orchard Ln, Highland, NY 12528
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  /40

  $359,900

  • 2 Beds
  • 2 Baths
  • 1,438 Sq Ft

  466 New Paltz Rd, Highland, NY 12528

  Charming Highland Retreat – Convenient, Comfortable, and Full of Character. Welcome to 466 New Paltz Road, a delightful property nestled in the heart of Highland, NY. This inviting home perfectly blends classic charm with modern updates, offering the ideal retreat for year-round living or a weekend getaway in the beautiful Hudson Valley. Step inside to find a bright and airy interior featuring 2

  Justin Phillips United RE Hudson Valley Edge

  466 New Paltz Rd, Highland, NY 12528
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  /24

  $350,000

  • 4 Beds
  • 1.5 Baths
  • 1,524 Sq Ft

  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
• 

  

  /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 Sothebys Intl

  136 Chapel Hill Rd, Highland, NY 12528
• 

  

  /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
• 

  

  /50

  $1,250,000

  • 14 Beds
  • 9 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
• 

  

  /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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  /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
• 

  

  /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
• 

  

  /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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  /52

  $3,950,000

  • 9 Beds
  • 12 Baths
  • 10,500 Sq Ft

  9 Chambers Rd, West Park, NY 12493

  A great legacy meets true luxury: Hudson Shore Estate, formerly home to one of Eleanor Roosevelt's early passion projects, a pioneering vocational school for women, has now been masterfully restored to its former glory and offers the perfect setting for a multi-generational family compound. A unique example of Arts & Craft design amongst its peer group of renowned Hudson River mansions, the

  Hayes Clement Compass Greater New York, LLC

  9 Chambers Rd, West Park, NY 12493
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  /26

  $950,000

  • Land
  • 46 Acres
  • $20,833 per Acre

  73 Peach Ln, Clintondale, NY 12515

  One Beautiful Apple Orchard with Pond. Mountain View with a Million Dollar View. Mature Apple Trees will be ready to pick this fall. Two parcels 20.9 Acres and 24.7 Acres for a total Acres of 45.6 Acres one mile county road frontage.can access the property from two county roads. At the highest area of the orchard. is a clearing.no apple Trees. just grass looking as far as you can see to the

  John Melchior Howard Hanna Rand Realty

  73 Peach Ln, Clintondale, NY 12515
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  /20

  $395,000

  • Land
  • 7 Acres
  • $54,861 per Acre

  75 Palazzo Ln, Clintondale, NY 12528

  Build your dream home or investment property on this exceptional 7.2-acre parcel of land, ideally situated in the heart of the Hudson Valley. Just 5 miles from the New Paltz Thruway exit (I-87), 6 miles to SUNY New Paltz, and 7 miles to the vibrant New Paltz Village, this location offers the perfect balance of privacy and accessibility.The property features a producing apple orchard with mature

  Michele Richards Four Seasons Sotheby's Int.

  75 Palazzo Ln, Clintondale, NY 12528
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  /33

  $2,000,000

  • 3 Beds
  • 2.5 Baths
  • 2,322 Sq Ft

  70 Floyd Ackert Rd, West Park, NY 12493

  A Rare Hudson Riverfront Opportunity - Historic Stone Home with Unmatched Views and Endless Potential It's not often a property like this becomes available—a one-of-a-kind 1870s stone ferry house, set on 3.3 private acres right at the edge of the Hudson River. With sweeping, unobstructed views and a direct connection to the water, this is a chance to create something truly extraordinary.Step onto

  Jeanne Rakowski Corcoran Country Living

  70 Floyd Ackert Rd, West Park, NY 12493
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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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  /36

  $445,000

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft

  67 Picnic Woods Rd, Clintondale, NY 12515

  Welcome to your dream ranch home in Clintondale, NY—where comfort, style, and convenience come together in perfect harmony. This clean, well-maintained home set on a serene 1-acre lot is relaxing and inviting, making it the perfect retreat. Imagine waking up to the serenity of the beautiful pond as you enjoy your breakfast on the rear deck or before sunset when the sun is low on the horizon—a

  JANICE CARRASCO Nexthome NOVACARR Realty

  67 Picnic Woods Rd, Clintondale, NY 12515
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  /6

  $232,000

  • Land
  • 3.90 Acres
  • $59,487 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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  /5

  $125,000

  • Land
  • 0.90 Acre
  • $138,889 per Acre

  120 Floyd Ackert Rd, Esopus, NY 12429

  Bring your plans! Here is your blank canvas for the home of your dreams. Located a short distance from Route 9W in West Park for easy commuting to Kingston or south to Highland and Metro North. Property is located on .9 acres with lots road frontage.

  Dawn Passante Coldwell Banker Village Green

  120 Floyd Ackert Rd, Esopus, NY 12429
• 

  

  /25

  $420,000

  • 3 Beds
  • 1.5 Baths
  • 1,562 Sq Ft

  8 Perkinsville Rd, Highland, NY 12528

  Discover your perfect Hudson Valley escape with this beautifully maintained raised ranch located in the heart of Highland, NY. Nestled on a quiet street and just minutes from the Mid-Hudson Bridge and NYS Thruway, this home offers both convenience and tranquility. This well-maintained 3-bedroom, 1.5-bath raised ranch combines classic charm with standout features—most notably, a sun-drenched

  Kelly Martin Michael A. Martin

  8 Perkinsville Rd, Highland, NY 12528
• 

  

  /43

  $295,000

  • 3 Beds
  • 2 Baths
  • 2,314 Sq Ft

  312 Crescent Ave, Highland, NY 12528

  A Romantic Restoration Opportunity | New Paltz NY Area 3BD | 2BA | Victorian w/ Carriage House Located in the beautiful hamlet of Clintondale Tucked in the rolling farm country of the Hudson Valley, (lots of farms equals low taxes) just 90 minutes from NYC by car bus or train. Metro north and Amtrak 14 mins away this quintessential Victorian offers a rare opportunity to restore something truly

  Machree Quaker The Machree Group, LLC

  312 Crescent Ave, Highland, NY 12528
• 

  

  /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
• 

  

  /6

  $825,000

  • Land
  • 16 Acres
  • $50,000 per Acre

  TBD South St, Lloyd, NY

  Prime property. This parcel is flat, mostly cleared, has a pond, sweeping views of the Shawangunk Mountains and borders the 27 hole Apple Greens Golf Course. 1,400 feet of the property adjoins the course. If golf is your game, it doesn't get any more convenient than this. Perfect for a community that grew up here, wants to stay here and are ready to downsize and become ''snow birds''. Here for

  Dennis Cooper Corcoran Country Living

  TBD South St, Lloyd, NY
• 

  

  /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 ample space for

  Jaynie Aristeo Ridgeline Realty

  451 New Paltz Rd, Highland, NY 12528
• 

  

  /6

  $825,000

  • Land
  • 16 Acres
  • $50,000 per Acre

  tbd South St, Highland, NY 12528

  Prime property. This parcel is flat, mostly cleared, has a pond, sweeping views of the Shawangunk Mountains and borders the 27 hole Apple Greens Golf Course. 1,400 feet of the property adjoins the course. If golf is your game, it doesn't get any more convenient than this. Perfect for a community that grew up here, wants to stay here and are ready to downsize and become ''snow birds''. Here for

  Dennis Cooper Corcoran Country Living

  tbd South St, Highland, NY 12528

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