Highland, NY Homes for Sale with Acreage

• 

  

  

  /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
• 

  

  

  /19

  $369,000

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

  38 Roxanne Blvd, Highland, NY 12528

  A/O 9/27/2025 (no available showings at this time) 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

  

  Amy Hawks

  Berardi Realty

  (845) 203-3694

  38 Roxanne Blvd, Highland, NY 12528
• 

  

  

  /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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  /8

  $195,000

  • Land
  • 22.3 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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  /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
• 

  

  /46

  $569,000

  • 4 Beds
  • 2.5 Baths
  • 2,270 Sq Ft

  93 Glen Rock Cir, Highland, NY 12528

  Move in Colonial shows pride of ownership. Set beautifully on 1.4 acres this 4 bedroom 2.5 bath stunner boasts modern kitchen with granite countertops custom cabinets and center island. It's open floorplan great room gives ample room for kitchen dining or cozying around the gas fireplace. For more formal dining there is a dining room. The entire first floor has equisite hardwood flooring From

  

  Randy Spiesman

  Weichert REALTORS

  (845) 413-2225

  93 Glen Rock Cir, Highland, NY 12528
• 

  

  /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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  /65

  $1,500,000

  • 3 Beds
  • 3.5 Baths
  • 4,572 Sq Ft

  74 Bellevue Rd, Highland, NY 12528

  Hudson River Views! This inviting home combines comfort, character, and convenience with a dramatic two-story foyer and open floor plan. Enjoy a cozy living room with a gas fireplace, formal dining area overlooking the river, and a kitchen with custom cherry cabinets, granite counters, and Jenn Air cooktop. A flexible room with French doors makes a great office or fourth bedroom. Bathroom and

  Hollis Dukler Coldwell Banker Village GreenN

  74 Bellevue Rd, Highland, NY 12528
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  /44

  $1,299,000

  • 3 Beds
  • 2.5 Baths
  • 3,068 Sq Ft

  243 Hawleys Corners Rd, Highland, NY 12528

  Discover the perfect blend of craftsmanship, comfort and opportunity in this stunning custom-built Craftsman home, offering over 3,000 square feet of living space on 20 picturesque acres. Previously subdivided with six additional parcels, this property offers exceptional potential for expansion, development or a private gathering retreat. Inside, you will find cathedral ceilings, custom woodwork,

  Melissa Pettinella Century 21 Alliance Realty Grp

  243 Hawleys Corners Rd, Highland, NY 12528
• 

  

  /39

  $1,195,000

  • 4 Beds
  • 3.5 Baths
  • 2,240 Sq Ft

  520 Plutarch Rd, Highland, NY 12528

  Modern Artisan Home on 5 Serene Acres Welcome to this reimagined modern retreat (+ New Paltz schools!), where every detail reflects a local artisan's vision and the signature craftsmanship of Lake North Designs. The exterior's mix of textures creates a bold architectural statement, while stone walls—sourced directly from the property—add grounding authenticity inside and out. The entryway makes a

  Bree Chambers Compass Greater NY, LLC

  520 Plutarch Rd, Highland, NY 12528
• 

  

  /44

  $869,000

  • 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 countertops,

  Lindsay Stevens eXp Realty

  1 Janine Place, 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
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  /11

  $265,000

  • 1 Bed
  • 1 Bath
  • 730 Sq Ft

  128 Vineyard Ave Unit 207, Highland, NY 12528

  Welcome to Highbridge Crossing, a modern river-town condominium building with direct access to the Hudson Valley Rail Trail in the heart of Highland, NY. This 803-square-foot first-floor residence blends smart design, comfort, and easy outdoor living—ideal for low-maintenance living without sacrificing style. The open-concept layout features large windows and seamless flow throughout. The custom

  Vitaly Isaacs Magic Of Great Neck Realty Inc

  128 Vineyard Ave Unit 207, Highland, NY 12528
• 

  

  /11

  $265,000

  • 1 Bed
  • 1 Bath
  • 730 Sq Ft

  128 Vineyard Ave Unit 206, Highland, NY 12528

  Welcome to Highbridge Crossing, a modern river-town condominium building with direct access to the Hudson Valley Rail Trail in the heart of Highland, NY. This 803-square-foot first-floor residence blends smart design, comfort, and easy outdoor living—ideal for low-maintenance living without sacrificing style. The open-concept layout features large windows and seamless flow throughout. The custom

  Vitaly Isaacs Magic Of Great Neck Realty Inc

  128 Vineyard Ave Unit 206, Highland, NY 12528
• 

  

  /11

  $340,000

  • 2 Beds
  • 1 Bath
  • 1,122 Sq Ft

  128 Vineyard Ave Unit 210, Highland, NY 12528

  Welcome to Highbridge Crossing, a modern river-town condominium building with direct access to the Hudson Valley Rail Trail in the heart of Highland, NY. This 803-square-foot first-floor residence blends smart design, comfort, and easy outdoor living—ideal for low-maintenance living without sacrificing style. The open-concept layout features large windows and seamless flow throughout. The custom

  Vitaly Isaacs Magic Of Great Neck Realty Inc

  128 Vineyard Ave Unit 210, Highland, NY 12528
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  /11

  $265,000

  • 1 Bed
  • 1 Bath
  • 730 Sq Ft

  128 Vineyard Ave Unit 205, Highland, NY 12528

  Welcome to Highbridge Crossing, a modern river-town condominium building with direct access to the Hudson Valley Rail Trail in the heart of Highland, NY. This 803-square-foot first-floor residence blends smart design, comfort, and easy outdoor living—ideal for low-maintenance living without sacrificing style. The open-concept layout features large windows and seamless flow throughout. The custom

  Vitaly Isaacs Magic Of Great Neck Realty Inc

  128 Vineyard Ave Unit 205, Highland, NY 12528
• 

  

  /11

  $270,000

  • 1 Bed
  • 1 Bath
  • 803 Sq Ft

  128 Vineyard Ave Unit 106, Highland, NY 12528

  Welcome to Highbridge Crossing, a modern river-town condominium building with direct access to the Hudson Valley Rail Trail in the heart of Highland, NY. This 803-square-foot first-floor residence blends smart design, comfort, and easy outdoor living—ideal for low-maintenance living without sacrificing style. The open-concept layout features large windows and seamless flow throughout. The custom

  Vitaly Isaacs Magic Of Great Neck Realty Inc

  128 Vineyard Ave Unit 106, Highland, NY 12528
• 

  

  /12

  $270,000

  • 1 Bed
  • 1 Bath
  • 803 Sq Ft

  128 Vineyard Ave Unit 104, Highland, NY 12528

  Welcome to Highbridge Crossing, a modern river-town condominium building with direct access to the Hudson Valley Rail Trail in the heart of Highland, NY. This 803-square-foot first-floor residence blends smart design, comfort, and easy outdoor living—ideal for low-maintenance living without sacrificing style. The open-concept layout features large windows and seamless flow throughout. The custom

  Vitaly Isaacs Magic Of Great Neck Realty Inc

  128 Vineyard Ave Unit 104, Highland, NY 12528
• 

  

  /31

  $450,000

  • 4 Beds
  • 2 Baths
  • 1,428 Sq Ft

  10 Carly Dr, Highland, NY 12528

  Discover the perfect blend of comfort, convenience, and lifestyle in this beautifully maintained 4-bedroom, 2-bathroom single-level home, tucked away in a peaceful cul-de-sac in sought-after Highland, NY. Sitting on a full acre, this property offers endless possibilities space to entertain, relax, and enjoy outdoor living. Cool off all summer long in the above-ground pool, or take in the privacy

  Megan Krusen eXp Realty

  10 Carly Dr, Highland, NY 12528
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  /6

  $199,900

  • Land
  • 11 Acres
  • $18,173 per Acre

  TBD Hawleys Corners Rd, Highland, NY 12528

  11 acres offering privacy and potential. The land is ideal for building a secluded estate, nature retreat located on a country road yet close to Route 299 leading to NYS Thruway. Mid Hudson Bridge 5 miles away. The parcels break down as follows:Parcel 1: 3.5 acresParcel 2: 4 acresParcel 3: 3.7 acresKey Features:Peaceful rural setting with minimal trafficSurrounded by woods

  Dawn Passante Coldwell Banker Village GreenN

  TBD Hawleys Corners Rd, Highland, NY 12528
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  /6

  $44,000

  • Land
  • 2.9 Acres
  • $15,172 per Acre

  TBD Hawleys Corners Rd, Highland, NY 12528

  This property is located in a desirable area that offers a balance of privacy and convenient access to key attractions in the Hudson Valley. Its location is situated just a few miles from the heart of downtown New Paltz and with Kingston also close by, you'll have easy access to all the vibrant shops, restaurants, and cultural scene. The site is also 6 miles from the Mid-Hudson Bridge and the

  Dominick Martorana Century 21 Alliance Rlty Group

  TBD Hawleys Corners Rd, Highland, NY 12528
• 

  

  /25

  $397,000

  • 3 Beds
  • 3 Baths
  • 1,661 Sq Ft

  7 River Rd, Highland, NY 12528

  Charming 1830s Eyebrow Colonial. Spacious Living Area with formal Dining Room and updated Kitchen. Laundry and one bedroom on first floor. 3 bedrooms, 3 Bathrooms. Walk to the Hamlet of Highland and the Highland Landing Park on the mighty Hudson River. Many restaurants and shops nearby as well as the Hudson Vallely Rail Trail. Soothing sounds from babbling Twaalfskill stream across the street.

  Elizabeth Decker Hudson Dwellings Realty

  7 River Rd, Highland, NY 12528
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  /26

  $599,000

  • 4 Beds
  • 2 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

  Ronnie Rebis Grist Mill Real Estate

  340 Vineyard Ave, Highland, NY 12528
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  /24

  $575,000

  • 3 Beds
  • 1 Bath
  • 2,086 Sq Ft

  269 Orchard Rd, Highland, NY 12528

  Nestled among scenic orchards is this beautiful, updated nineteenth century farm house situated on almost 20 acres of beautiful pasture land and woods. This charming 3 bedroom home has a lovely full bath and plenty of living space for both humans and horses alike. The current owner keeps her horses on the property which is equipped with 2 run-in sheds and 7 shed row stalls which all have power

  Daniel Balassone VYLLA Home

  269 Orchard Rd, Highland, NY 12528
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  /14

  $135,000

  • 2 Beds
  • 1 Bath
  • 552 Sq Ft

  407 Swartekill Rd, Highland, NY 12528

  Charming 2-Bedroom Mobile Home on 1.29 Acres in Swartekill Neighborhood Discover the potential of this cozy 2-bedroom, 1-bathroom mobile home nestled on a spacious 1.29-acre lot in the desirable Swartekill neighborhood, located in the Town of Esopus and within the sought-after New Paltz School District. This property offers a unique opportunity for those looking to invest, renovate, or create

  Kristen Zigouras eXp Realty

  407 Swartekill Rd, Highland, NY 12528
• 

  

  /31

  $399,000

  • 3 Beds
  • 2.5 Baths
  • 1,104 Sq Ft

  534 U S 44, Highland, NY 12528

  Set high on a hill with mountain views, this fully remodeled home is turn-key and ready to enjoy. The open floor plan connects the kitchen, dining, and living areas—ideal for both everyday living and entertaining. The first floor also features a convenient half bath and laundry room, while upstairs offers three bedrooms and two baths, including a primary bedroom with ensuite. A full attic

  Sally Sprogis Four Seasons Sotheby's Int'l R

  534 U S 44, Highland, NY 12528
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  /10

  $110,000

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

  748 State Route 44 55, Highland, NY 12528

  Discover the perfect canvas for your vision on this expansive 2.1-acre parcel—fully surveyed and complete with a percolation test–approved septic system, offering clarity and confidence as you plan your future home or weekend escape. Tucked along a quiet, picturesque country road, this property delivers the ideal blend of privacy, nature, and accessibility. Its prime location places you just

  Ashley Olson Minard eXp Realty

  748 State Route 44 55, Highland, NY 12528
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  /8

  $148,000

  • Land
  • 5.56 Acres
  • $26,619 per Acre

  0 Black Bear Ct, Highland, NY 12719

  Yess! Your Dreams Have Been Answered...This Rare Lot..Privacy/5+ Acres/ 40' Pond/ Silence/ 7 Min To Barryville/ 10 Minutes To EldredReady For You.. To Build YOUR Future Retreat!! Yes, Moss Covered Rocks And A Gentle Slope Allowing For A Walk Out Lower Level. Gorgeous Trees Tuck You Into Your Private Serenity. It All Begins With Your Land and Then Your Dream Home Can Be Designed

  Jessica Jagel Cabins & Canoes Real Estate

  0 Black Bear Ct, Highland, NY 12719
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  /17

  $50,000

  • Land
  • 1.36 Acres
  • $36,765 per Acre

  0 White St, Highland, NY 12528

  Looking for the perfect lot for your new home? This lovely 1.36-acre wooded lot is situated on a gentle rise above an established community in historic Highland. It offers the best of both worlds; peace, privacy, and appealing elevated views, with convenient access to all amenities and the security of having neighbors nearby. Easy access to the Walkway Over the Hudson, Empire State Rail

  Carolyn Michelle KW MidHudson

  0 White St, Highland, NY 12528
• 

  

  /31

  $500,000

  • Land
  • 97.1 Acres
  • $5,149 per Acre

  TBD Lily Lake Rd, Highland, NY 12528

  A rare opportunity to own a breathtaking 97-acre property featuring the very lake that gives Lily Lake Road its name. Tucked away in the beautiful countryside of Highland, New York, this one-of-a-kind parcel offers unmatched privacy, natural beauty, and endless potential for your dream retreat or legacy estate.At the heart of the property lies Lily Lake — a serene, private body of water

  John Quinn Quinn Realty Group Inc.

  TBD Lily Lake Rd, Highland, NY 12528
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  /48

  $509,900

  • 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
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  /4

  $150,000

  • Land
  • 1.5 Acres
  • $100,000 per Acre

  0 Haviland Rd Unit KEY899872, Highland, NY 12528

  Discover the potential of this rare 1.5 acre non-conforming lot with breathtaking views of the Hudson River. This vacant parcel offers the perfect canvas for your dream build. Whether you envision a serene weekend retreat or a year round residence immersed in natures beauty. This property provides a gloriuos vantage point for sunrise coffee, sunset gatherings and endless water views. While the

  Anthony DeGelormo Century 21 Alliance Rlty Group

  0 Haviland Rd Unit KEY899872, Highland, NY 12528
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  /26

  $325,000

  • 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
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  /6

  $275,000

  • Land
  • 6.2 Acres
  • $44,355 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,

  Theodore Chazkel Four Seasons Sotheby's Int'l R

  9 Lumen Ln, Highland, NY 12528
• 

  

  /3

  $150,000

  • Land
  • 6.7 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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  /5

  $59,000

  • Land
  • 6.06 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
• 

  

  /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
• 

  

  /15

  $399,000

  • Land
  • 8.7 Acres
  • $45,862 per Acre

  3748 Us Highway 9w, Highland, NY 12528

  8.7 acres of untouched land just south of the Mid Hudson Bridge. Current plan was to build a church. Site plan and survey attached with the docs. Property is next to Walgreens and will allow many uses. Zoning Examples to be confirmed by buyer agent, Light Business Use, Convenience store, day care adult or child, funeral home, office, skating rink, bowling alley, Vet office, warehouse, park,

  Jason Madison eXp Realty

  3748 Us Highway 9w, Highland, NY 12528
• 

  

  /15

  $399,000

  • Land
  • 8.7 Acres
  • $45,862 per Acre

  3748 Route 9w, Highland, NY 12528

  8.7 acres of untouched land just south of the Mid Hudson Bridge. Current plan was to build a church. Site plan and survey attached with the docs. Property is next to Walgreens and will allow many uses. Zoning Examples to be confirmed by buyer agent, Light Business Use, Convenience store, day care adult or child, funeral home, office, skating rink, bowling alley, Vet office, warehouse, park,

  Lindsay Stevens eXp Realty

  3748 Route 9w, Highland, NY 12528
• 

  

  /16

  $35,000

  • Land
  • 1.09 Acres
  • $32,110 per Acre

  0 Eldred-Yulan Rd Unit KEYH6315244, Highland, NY 12792

  Cleared 1.09 acre building lot atop a hill with a view of Bodine Lake. Lot has been cleared for home site and has a drilled well in place. Septic plans on file.

  Cara Rieber Rieber Realty Inc

  0 Eldred-Yulan Rd Unit KEYH6315244, Highland, NY 12792

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