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Highland, NY Houses for Sale

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  • /27

    $585,000

    • 3 Beds
    • 2 Baths
    • 2,386 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

    Agent Photo

    Hayes Clement

    Compass Greater New York, LLC

    (845) 456-9362

    660 N Chodikee Lake Rd, Highland, NY 12528
  • /34

    $495,000

    • 5 Beds
    • 4 Baths
    • 2,366 Sq Ft

    258 Martin Ave, Highland, NY 12528

    ACCEPTED OFFER AS OF SEPT 2, 2025. Major space meets major opportunity: This versatile 2-family home nestled on 2 sunny acres offers privacy plus big potential for comfortable living and extra income. Perfectly adaptable, you can rent both units, live in one while renting the other, or knock down a wall to create a spacious single-family residence. The first unit is an extra roomy, one-level home

    Agent Photo

    Hayes Clement

    Compass Greater NY, LLC

    (845) 377-4797

    258 Martin Ave, Highland, NY 12528
  • /49

    $1,175,000

    • 7 Beds
    • 5 Baths
    • 5,730 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. The first house, built in 1820 by William Brooks and

    Agent Photo

    Hayes Clement

    Compass Greater NY, LLC

    (845) 378-9916

    660 N Chodikee Lake Rd, Highland, NY 12528
  • /41

    $825,000 Open Sun 11AM - 2PM

    • 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

    Agent Photo

    Donna Brooks

    Compass Greater New York, LLC

    (845) 250-6194

    7 Elliotts Ln, Highland, NY 12528
  • /48

    $549,900

    • 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
  • /55

    $750,000

    • 3 Beds
    • 3 Baths
    • 2,596 Sq Ft

    1 Jonathan Ct, Highland, NY 12528

    Charming Colonial on 1.39 Acres with Resort-Style AmenitiesWelcome to this beautifully maintained Colonial nestled on 1.39 acres of mature, professionally landscaped grounds. This inviting 3-bedroom, 3 full-bath home offers the perfect blend of timeless charm and modern amenities in a sought-after location near the Mid-Hudson Bridge.Step inside to find a spacious layout featuring

    Danielle Carlson-murphy Start Home Smart, Inc.

    1 Jonathan Ct, Highland, NY 12528
  • /33

    $450,000

    • 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
  • /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
  • /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
  • /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
  • /49

    $419,000

    • 4 Beds
    • 2 Baths
    • 2,128 Sq Ft

    307 Vineyard Ave, Highland, NY 12528

    Classic 1900 Farmhouse with Timeless Charm - 4 Beds, 2 Baths on One AcreNestled on residential-level farmland, you step into the charm of yesteryear with this sunlit 1900 farmhouse. Enjoy rich woodwork, a welcoming layout, hardwood floors just waiting to be refinished. Four floors offer 4 bedrooms, 2 full baths, 2 additional rooms on the second floor offer incredible expansion

    Debra Dooley BHHS HUDSON VALLEY PROP-NP

    307 Vineyard Ave, Highland, NY 12528
  • /25

    $375,000

    • 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
  • /50

    $399,000

    • 3 Beds
    • 2 Baths
    • 1,934 Sq Ft

    4 Salk Dr, Highland, NY 12528

    Welcome Home to Comfort, Style & Mountain Views This 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 baths.

    Barbara Korabel FOUR SEASONS REALTY GROUP

    4 Salk Dr, Highland, NY 12528
  • /43

    $419,000

    • 3 Beds
    • 2 Baths
    • 2,248 Sq Ft

    20 Lauretta Dr, Highland, NY 12528

    Tucked away on a quiet dead-end road, set high with scenic mountain views, this well-kept Raised Ranch is ready for your next chapter in the Hudson Valley. Freshly painted and move-in ready, the home offers 3 bedrooms, 2 bathrooms, a wood-burning fireplace, and a fenced-in backyard. The updated kitchen and spacious, finished lower level—with oversized windows framing the views—provide comfort and

    Peter Ilani BHHS Hudson Valley Properties

    20 Lauretta Dr, Highland, NY 12528
  • /7

    $399,900

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

    29 Oakes Rd, Highland, NY 12528

    An exceptional and rare opportunity to own a piece of the Hudson Riverfront between two of the region’s most iconic landmarks, the Mid-Hudson Bridge and the Walkway Over the Hudson. Located on the Highland side, presenting a blend of natural beauty and historic charm. At the heart of the property is a c.1840s two bedroom, one bath home, offering timeless character and panoramic views of the

    Anthony DeGelormo Century 21 Alliance Rlty Group

    29 Oakes Rd, Highland, NY 12528
  • /13

    $329,999

    • 3 Beds
    • 1 Bath
    • 1,372 Sq Ft

    365 Crescent Ave Unit 367, Highland, NY 12528

    Welcome to this charming and beautifully updated home, nestled in a spacious corner lot in a quiet neighborhood. This inviting property offers the perfect blend of country charm and modern conveniences. Step inside to find a warm and welcoming country-style kitchen featuring a cozy coffee bar and breakfast nook, perfect for starting your mornings. The kitchen boasts newer appliances and flows

    Ronnie Rebis Grist Mill Real Estate

    365 Crescent Ave Unit 367, Highland, NY 12528
  • /15

    $270,000

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

    53 Sunny Brook Cir, Highland, NY 12528

    Welcome to this inviting 2-bedroom townhouse unit, perfectly situated in one of Highland’s most desirable and affordable communities. Offering both comfort and convenience, this home features a spacious layout, one-level living and a rare sense of privacy. Step outside to your own fenced-in patio, an ideal space for relaxing, gardening, or entertaining. Inside, you'll find two well-sized

    Danielle Bartula Howard Hanna Rand Realty

    53 Sunny Brook Cir, Highland, NY 12528
  • /17

    $349,000

    • 3 Beds
    • 1 Bath
    • 1,816 Sq Ft

    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 GreenN

    283 Hawleys Corners Rd, Highland, NY 12528
  • /29

    $389,000

    • 3 Beds
    • 1.5 Baths
    • 1,670 Sq Ft

    46 Brescia Blvd, Highland, NY 12528

    Discover your upstate oasis at 46 Brescia Blvd — a beautifully renovated 3-bedroom, 1.5-bath home offering the perfect mix of comfort, style, and indoor-outdoor living in the heart of the Hudson Valley.Located just 90 minutes from NYC and minutes from the Hudson Valley Rail Trail, wineries, and local farm markets, this move-in-ready home features modern upgrades, smart home touches, and

    Heather Bragg ReAttached

    46 Brescia Blvd, Highland, NY 12528
  • /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
  • /28

    $330,000

    • 2 Beds
    • 1 Bath
    • 1,723 Sq Ft

    578 South St, Highland, NY 12528

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

    Michele Marina Atlantica East Associates LLC

    578 South St, Highland, NY 12528
  • /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
  • /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
  • /35

    $4,600,000

    • 16 Beds
    • 10.5 Baths
    • 11,160 Sq Ft

    35 Washington Lake Rd, Highland, NY 12792

    Amazing One-of-a-kind Lakefront Home! This magnificent 11,000+ SF home features massive 2 story great room w/ stone fireplace, floating staircase & spiral staircase, commercial kitchen w/ walk in freezer & refrigerator, huge dining area/ game room/ wet bar. The home also offers 16 bedrooms, 10.5 baths, theater room, office, enclosed porch, huge patio featuring outdoor kitchen w/ wood fired pizza

    Jill Barnes Cabins & Canoes Real Estate

    35 Washington Lake Rd, Highland, NY 12792
  • /44

    $899,999 Open Sat 12PM - 2PM

    • 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

    Lindsay Stevens eXp Realty

    1 Janine Place, Highland, NY 12528
  • /8

    $149,000

    • 2 Beds
    • 1 Bath
    • 1,096 Sq Ft

    18 Hillside Place, Highland, NY 12528

    Looking for a great opportunity? Look no more! This property has tons of potential and is average in living space size for the neighborhood. It is located close to main roads with easy access to local amenities, such as shopping, banking, schools, and various eateries. Per our bpo/tax describe the property as a SFR (ranch) built in 1950. It has a GLA of approx. 1096 and has 2 bedrooms and 1bath,

    Christopher Rose Listing by REALHome Services & Solutions

    18 Hillside Place, Highland, NY 12528
  • /25

    $345,000

    • 3 Beds
    • 6 Baths
    • 2,444 Sq Ft

    785 South St, Highland, NY 12528

    This unique property is like no other. Once you enter you will be surprised at the space inside as well as the 13 acres outside. Great opportunity for you to own a one of a kind property that you can make it your own by adding some TLC and vision to make your own oasis. Come see this diamond in the rough that is close to major highways and shoppping area.

    Brenda Watington W Manor LLC

    785 South St, Highland, NY 12528
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