Highland, NY Homes for Sale

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  /45

  $299,999

  • 3 Beds
  • 1 Bath
  • 972 Sq Ft

  71 North Rd, Highland, NY 12528

  Vintage Hudson Valley charm, original character, and plenty of potential come together at 71 North Road in Highland. This inviting 3-bedroom, 1-bath home is filled with the details that give an older home its warmth and personality—from beautiful original woodwork and trim to hardwood floors, classic French doors, and original wood siding.A sweet covered front porch welcomes you home and

  Hilary Ryan Goldman Howard Hanna Rand Realty

  71 North Rd, Highland, NY 12528
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• 

  

  

  /22

  $199,000

  $50K PRICE DROP

  • Land
  • 6.38 Acres
  • $31,191 per Acre

  0 Browning Blvd Unit KEY997085, Highland, NY 12719

  Escape to this beauty lakefront property sitting on 6.38 gorgeous acres in the private gated community of York Lake Shores. Enjoy boating, sailing, swimming, and fishing on the pristine lake while surrounded by peace and nature. Ideally located just two hours from New York City and under 20 minutes to the Metro-North train, this property offers the perfect balance of seclusion and convenience.

  Dawn Payne Payne Team LLC

  0 Browning Blvd Unit KEY997085, Highland, NY 12719
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  /6

  $179,000

  $20K PRICE DROP

  • Land
  • 11 Acres
  • $16,273 per Acre

  TBD Hawleys Corners Rd, Highland, NY 12528

  11 acres offering privacy and potential. The land is ideal for building a secluded estate or your own nature retreat. Located on a country road, yet close to Route 299 leading to the NYS Thruway. The Mid-Hudson Bridge is only 5 miles away. The parcels break down as follows: Parcel 1: 3.5 acres, Parcel 2: 4 acres, and Parcel 3: 3.7 acres. Key features include a peaceful rural setting with minimal

  Dawn Passante Coldwell Banker Village Green

  TBD Hawleys Corners Rd, Highland, NY 12528
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  /43

  $995,000

  • 2 Beds
  • 2 Baths
  • 1,575 Sq Ft

  83 Cotter Rd, Highland, NY 12528

  Tucked away at the end of a 1,700+ foot private driveway, this one-of-a-kind custom-built retreat offers the peace, privacy, and natural beauty you’ve been searching for. Situated on an incredible 63-acre parcel in the Town of Plattekill (Wallkill School District), this property is a rare opportunity for outdoor enthusiasts, hunters, weekend escape seekers, or anyone looking to enjoy a secluded

  Gary MacEntee Keller Williams Realty

  83 Cotter Rd, Highland, NY 12528
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  /35

  $680,000

  • 4 Beds
  • 2.5 Baths
  • 2,464 Sq Ft

  555 Plutarch Rd, Highland, NY 12528

  Perfectly sited on a quiet walking road, this handsome Center-hall Colonial is now available for the first time in almost 2 decades. The nearly 7 acres offer an oasis around the residence with a stream that opens into the Swarte Kill (Black Creek) to kayak and experience wetland wildlife.Right from the full-length rocking chair porch, you feel so at home. This four-bedroom residence has a

  Eliane Abramoff Four Seasons Sothebys Intl

  555 Plutarch Rd, Highland, NY 12528
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  /27

  $480,000

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

  98 North Rd, Highland, NY 12528

  This charming 1900 farmhouse in Highland 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. There's a large dining area for large gatherings or intimate dinners. The primary bedroom is on the first

  Dawn Passante Coldwell Banker Village Green

  98 North Rd, Highland, NY 12528
• 

  

  /22

  $2,100,000

  • Land
  • 70.5 Acres
  • $29,787 per Acre

  243 Vineyard Ave Unit 251, Highland, NY 12528

  Spectacular 70 acre parcel located right outside the village of Highland. May be used as a farm or subdivided. Parcel has 3 rentals located on it in addition to 1 vacant house. Also on this property is a very large steel building with high ceilings and oversized garage doors as well as a barn! Close commuter location - Metro North, NYS Thruway, Mohonk Mountains and Hudson Valley Rail Trail.

  John Quinn Quinn Realty Group Inc

  243 Vineyard Ave Unit 251, Highland, NY 12528
• 

  

  /18

  $797,000

  $58K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,182 Sq Ft

  110 Macks Ln, Highland, NY 12528

  Welcome to this stunning 3,100 sq. ft. Colonial set on a picturesque 2.5-acre lot. Featuring 4 spacious bedrooms and 2.5 baths, this home blends comfort with timeless elegance. The chef's kitchen serves as the heart of the home--perfect for both entertaining and everyday living--whileselect bedrooms offer private or adjoining bath access for added convenience.Beautiful hardwood floors run

  Elizabeth Decker Hudson Dwellings Realty

  110 Macks Ln, Highland, NY 12528
• 

  

  /19

  $629,000

  • 4 Beds
  • 2 Baths
  • 2,236 Sq Ft

  120 Vineyard Ave, Highland, NY 12528

  Charming Two-Family Home in Highland, NYWelcome to this inviting two-family home in the Town of Lloyd, ideally located in the heart of the Hudson Valley and within walking distance to the Hamlet of Highland. Each floor offers 2 bedrooms and 1 full bath, making this property an excellent opportunity for an owner-occupant, multi-generational living, or investment.Recent improvements

  Angela Chenery Century 21 Alliance Rlty Group

  120 Vineyard Ave, Highland, NY 12528
• 

  

  /35

  $599,000

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

  6 Apple Ln, Highland, NY 12528

  Welcome to this well-maintained home offering a thoughtful blend of comfort, style, and convenience. Enjoy breathtaking sunrise views from the backyard and beautiful sunsets from the front of the home. The backyard features a spacious deck, perfect for relaxing or entertaining, while professional landscaping enhances both the front and rear of the property. Recent updates include hardwood

  Donna Gray Redfin Real Estate

  6 Apple Ln, Highland, NY 12528
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  /24

  $530,900

  • 3 Beds
  • 3 Baths
  • 2,050 Sq Ft

  452 Vineyard Ave, Highland, NY 12528

  This home is completely remodeled. New roof, new siding new windows new Insulation all new electrical all new plumbing. All new flooring throughout the home. Brand new kitchen with quartz countertops, completely remodeled bathrooms. Brand new central air unit brand new furnace ,brand new hot water heater. This Home is just minutes away from the mid Hudson Bridge and the Minnewaska mountains.

  Derek Greene Greene Realty Group

  452 Vineyard Ave, Highland, NY 12528
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  /32

  $485,000

  $114K PRICE DROP

  • 4 Beds
  • 2.5 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 retro

  Ronnie Rebis Grist Mill Real Estate

  340 Vineyard Ave, Highland, NY 12528
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  /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 rocking-chair

  Artur Galustyan Century 21 Alliance Rlty Group

  346 Crescent Ave, Highland, NY 12528
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  /47

  $474,000

  • 3 Beds
  • 2 Baths
  • 1,492 Sq Ft

  4 Alex Ct, Highland, NY 12528

  Delightful Ranch in welcoming Mountainside Woods features an inviting rocking-chair front porch overlooking neighbor-friendly streets with sidewalks. Mountainside offers the perfect blend of community and location, nestled in nature at the foot of beautiful Illinios Mtn with easy access to numerous walking and hiking trails, parks, farmers markets, and area attractions. This popular Taconic model

  Susan Todd BHHS Hudson Valley Properties

  4 Alex Ct, Highland, NY 12528
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  /6

  $110,000

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

  748 State Route 44 55, Highland, NY 12528

  BOHA 2.1-acre parcel ready to build and approved for a 4-bedroom home in beautiful Ulster County. Ideally located just 1 mile from Rocking Horse Ranch Resort, with convenient access to the Mid-Hudson Bridge and NY State Thruway. This exceptional property offers the perfect blend of seclusion and accessibility. The approved homesite is nestled well back from the road, creating a peaceful, secluded

  Darci Russo KW MidHudson

  748 State Route 44 55, Highland, NY 12528
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  /12

  $400,000

  • 5 Beds
  • 3 Baths
  • 2,700 Sq Ft

  19-21 Church St, Highland, NY 12528

  Village of Highland three family comprised of (2) two bedroom units and (1) one bedroom unit. Spacious apartments with well proportioned rooms. Natural gas for heat & hot water. Separate utilities & off street parking. Centrally located with easy access to village amenities, Route 9W & Mid-Hudson Bridge.

  Dan Axtmann BHHS Hudson Valley Properties

  19-21 Church St, Highland, NY 12528
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  /46

  $575,000

  $24K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,340 Sq Ft

  105 S Chapel Hill Rd, Highland, NY 12528

  Welcome to this spacious and inviting ranch home in the heart of Highland, conveniently located near the iconic Mid-Hudson Bridge and just minutes from shopping, restaurants, commuter routes, and all that the Hudson Valley has to offer. The main level features three comfortable bedrooms and a bright, open layout designed for everyday living. The spacious kitchen offers abundant cabinet and

  Dawn Passante Coldwell Banker Village GreenN

  105 S Chapel Hill Rd, Highland, NY 12528
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  /42

  $799,000

  • 5 Beds
  • 5 Baths

  239-241 Fosler Rd, Highland, NY 12528

  Beautiful well maintained multi-family property offer, a rare opportunity for both owner-occupant & investors. Two houses that sit on 15 acres with endless revenue generating opportunities. The deed allows for the property to be subdivided & extending the private road along northern property line. The main house is a single family that features 2 bedrooms, 2.5 bathrooms with a full finished

  Maurice Bailey Neighborhood Assistance Corp

  239-241 Fosler Rd, Highland, NY 12528
• 

  

  /19

  $225,000

  • Land
  • 2.69 Acres
  • $83,643 per Acre

  19 Spruce Ln, Highland, NY 12528

  Tucked along a quiet country lane just minutes from both Highland and the vibrant Village of New Paltz, this beautiful parcel offers the opportunity to create a home that feels connected to the landscape around it. Whether you envision a peaceful weekend retreat or the place you'll call home for years to come, this setting invites you to slow down and settle into the rhythm of the Hudson Valley.

  Christina Ahouse Four Seasons Sotheby's Int'l-K

  19 Spruce Ln, Highland, NY 12528
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  /50

  $540,000

  $10K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,696 Sq Ft

  14 Blossom Grove Ct, Highland, NY 12528

  Welcome home to this warm and welcoming raised ranch home in the Wallkill school district! Located on a picturesque 1.2 acre corner lot on a beautiful cul-de-sac in the Town of Plattekill. This lovingly maintained home features 3 bedrooms and 3 full bathrooms, with a spacious and versatile layout that was designed for comfortable living. Be sure to check out the oversized pantry at the bottom of

  Gary MacEntee Keller Williams Realty

  14 Blossom Grove Ct, Highland, NY 12528
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  /33

  $674,900

  • 3 Beds
  • 2.5 Baths
  • 2,144 Sq Ft

  10 Eisgruber Park Ln, Highland, NY 12528

  Privacy and seclusion await in this well maintained home. The gourmet eat-in kitchen features vaulted ceilings, granite island, wine bar, double ovens, stainless steel appliances, and abundant cabinetry, and sliding glass door leading to a deck. The open concept living flows into the formal dining room with a bay window and hardwood floors. Upstairs, the primary suite boasts vaulted ceilings, a

  Margaret Thorne KW MidHudson

  10 Eisgruber Park Ln, Highland, NY 12528
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  /50

  $1,150,000

  • 9 Beds
  • 5 Baths

  52 John White Rd Unit 50, Highland, NY 12528

  Exceptional Hudson Valley Quadruplex Investment Opportunity on 16.4 Private AcresRarely does a property like this become available. Whether you're searching for a high-performing investment, a private compound, or an owner-occupied property with substantial rental income, this unique estate offers endless possibilities.Tucked away at the end of a quiet country road, the property features

  Jackie Siracuse Absolute Real Estate of NY Inc

  52 John White Rd Unit 50, Highland, NY 12528
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  /3

  $55,000

  • Land
  • 9,583 Sq Ft
  • $250,000 per Acre

  0 State Route 97 Unit KEY979499, Highland, NY 12719

  Prime commercial opportunity at one of the busiest intersections in the area! Situated on the corner of Routes 97 & 55, this highly visible .22-acre parcel features an existing billboard perfect for generating immediate income or maximizing advertising exposure. Included is an additional .74-acre parcel just a short distance away, offering expanded potential for development or business use.

  Dawn Payne Payne Team LLC

  0 State Route 97 Unit KEY979499, Highland, NY 12719
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  /40

  $570,000

  $15K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,856 Sq Ft

  98 Black Creek Rd, Highland, NY 12528

  Welcome to **98 Black Creek Road**—a beautifully maintained split-level home offering the perfect blend of privacy, space, and convenience in the heart of Esopus.Nestled on approximately **2 acres** of peaceful, tree-lined property, this move-in ready residence features **3 spacious bedrooms, 2.5 bathrooms, and over 2,200 square feet** of comfortable living space. Sunlight fills the open

  Jorge Lugo Real Broker NY LLC

  98 Black Creek Rd, Highland, NY 12528
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  /9

  $329,900

  $15K PRICE DROP

  • 4 Beds
  • 1.5 Baths
  • 2,040 Sq Ft

  136 Camp Sunset Rd, Highland, NY 12528

  Four bedroom, 1.5 bathroom Colonial in Town of Plattekill on 2.1 acres in Marlboro Schools! Rocking chair porch overlooking your side yard. Close to shopping, schools and amenities. Sold as-is. Buyer to pay NYS and any local transfer taxes. Offers with rehab loan financing must be accompanied by pre-qual letter; cash offers with proof of funds. Please see agent remarks for access, showing

  Brian Smith River Realty Services, Inc.

  136 Camp Sunset Rd, Highland, NY 12528
• 

  

  /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
• 

  

  /6

  $299,000

  • 3 Beds
  • 2 Baths
  • 1,425 Sq Ft

  933 South St, Highland, NY 12528

  Opportunity awaits on this private 4.52-acre property in the Town of Plattekill. Nestled among mature trees, this property features a 3-bedroom, 2-bath Cape Cod home with approximately 1,425 square feet of living space, a detached garage, and additional outbuildings. The home is being sold strictly as-is and presents an excellent opportunity for investors, contractors, or buyers looking to

  Zak Abdullah Weichert New Homes Co

  933 South St, Highland, NY 12528
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  /32

  $489,000

  $11K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,844 Sq Ft

  41 Penny Ln, Highland, NY 12528

  Welcome to 41 Penny Lane, a beautifully maintained, move-in ready 3-bedroom, 2.5-bath ranch that has been lovingly cared for nearly 40 years. Tucked away on a quiet, private, dead-end road and set on a picturesque 0.52-acre lot, this 1,844-square-foot home offers easy, single-level living with a wonderful connection to the outdoors. Walk in and you're greeted by an open, light-filled living

  Jacob Cohen eXp Realty

  41 Penny Ln, Highland, NY 12528
• 

  

  /55

  $1,500,000

  • 3 Beds
  • 2.5 Baths
  • 2,520 Sq Ft

  60 Palazzo Ln, Highland, NY 12528

  This bold custom built home sits atop a hill like a postcard extolling the beauty of the Hudson Valley. Built to exacting specifications and with an understanding of how people live best by a master craftsman, this is a post and beam masterpiece in an inspiring setting. Uniquely, it offers all the bells and whistles you expect in a new luxury home while also feeling like an heirloom. Set on 4

  Dawn Passante Coldwell Banker Village GreenN

  60 Palazzo Ln, Highland, NY 12528
• 

  

  /50

  $529,000

  • 7 Beds
  • 4 Baths

  53 Main St, Highland, NY 12528

  Some properties ask you to be patient. This one puts money in your pocket from closing day.Fully occupied and cash flowing, this commercial-residential multi-family sits on Main Street in the heart of Highland, steps from the Walkway Over the Hudson, one of the most visited destinations in the entire Hudson Valley. Two tenanted units. Month-to-month leases. Current rents below market

  Amy McArdle eXp Realty

  53 Main St, Highland, NY 12528
• 

  

  /30

  $545,000

  • 3 Beds
  • 2.5 Baths
  • 1,682 Sq Ft

  9 Emerson Terrace, Lloyd, NY 12528

  Welcome to Mountainside Woods, where luxury, comfort, and convenience come together.Why wait for new construction when you can move right into this stunning former model home in the highly sought-after Mountainside Woods community? Thoughtfully designed with both style and functionality in mind, this beautifully appointed home is loaded with premium upgrades.The gourmet kitchen serves as

  Megan Krusen eXp Realty

  9 Emerson Terrace, Lloyd, NY 12528
• 

  

  /19

  $429,000

  • 4 Beds
  • 2 Baths
  • 1,443 Sq Ft

  1 Jackman St, Highland, NY 12528

  Discover the charm of this quaint four-bedroom farmhouse nestled on a quiet private road in the Village of Highland. Filled with character, the home features beautiful original woodwork and hardwood floors that showcase its timeless appeal. Outside, the inviting yard provides a peaceful setting to relax, entertain, or simply enjoy the tranquility of home.What truly makes this property special

  Dawn Passante Coldwell Banker Village Green

  1 Jackman St, Highland, NY 12528
• 

  

  /13

  $500,000

  $195K PRICE DROP

  • Land
  • 11.5 Acres
  • $43,478 per Acre

  TBD Route 9w, Highland, NY 12528

  Attention Investors! 11.5 acres located just minutes from the Mid-Hudson Bridge in desirable Highland, NY ready for developing. Ideally located on a high traffic state highway with over 1,000 feet of road frontage and tons of visibility. This lot sits directly across the highway from the future river front development named "The Hudson Valley Wine Village" which is proposed to have 800 new

  John Quinn Quinn Realty Group Inc

  TBD Route 9w, Highland, NY 12528
• 

  

  /15

  $169,900

  $5K PRICE DROP

  • Land
  • 5.84 Acres
  • $29,092 per Acre

  0 Crawford Rd Unit KEY983986, Highland, NY 12528

  Escape to the peace and beauty of the Sullivan County Catskills with this lovely 5.8-acre parcel on Crawford Rd in the Town of Highland. Partially cleared and very private, this property offers the perfect setting to build your dream home in the country. Imagine relaxing on your future front porch or back deck while watching eagles soar overhead, enjoying star-filled skies, and taking in the

  Dominick Tufano RE/MAX Benchmark Realty Group

  0 Crawford Rd Unit KEY983986, Highland, NY 12528
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  /8

  $60,000

  • Land
  • 20,908 Sq Ft
  • $125,000 per Acre

  0 Route 9w Unit KEYH6287477, Lloyd, NY 12528

  Centrally located .48 acre lot on Rt. 9W just outside the quaint village of Highland. Lot is zoned GB and is situated next to a local bank, major fast food establishments, gas stations and assorted businesses.

  John Quinn Quinn Realty Group Inc

  0 Route 9w Unit KEYH6287477, Lloyd, NY 12528

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