Homes for Sale near Highland High School

• 

  

  /2

  $185,000

  • Land
  • 10,454 Sq Ft
  • $770,833 per Acre

  224 Vineyard Ave, Highland, NY 12528

  Recent home demolished and removed. .24 acre lot with town water and sewer (Natural gas on the street but not to the lot). 1.5 miles to the Hamlet of Highland. Ask us about our custom home affordability program.

  

  Danielle Carlson-Murphy

  Start Home Smart, Inc.

  224 Vineyard Ave, Highland, NY 12528
• 

  Explore Highland High School

• 

  

  /2

  $200,000

  • Land
  • 6.2 Acres
  • $32,258 per Acre

  0 Vineyard Ave Unit 20256184, Highland, NY 12528

  Rare find. 6.2 acres with town water, sewer and gas. 1/2 zoning can have single family, multi family and multiple units.

  

  Danielle Carlson-Murphy

  Start Home Smart, Inc.

  0 Vineyard Ave Unit 20256184, Highland, NY 12528
• 

  

  /2

  $325,000

  • Land
  • 9.7 Acres
  • $33,505 per Acre

  (Lot 1) 111 South St, Highland, NY 12528

  Build your custom dream home on this shovel-ready 9,7-acre homesite in a newly approved and recorded 4-lot subdivision totaling nearly 49 acres. All the hard work is done: perc test completed, well & septic approved by the Ulster County Board of Health, and electric & fiber already run to the shared driveway. Accessed via a common driveway, the lot offers privacy and a natural Hudson Valley

  

  Mark Friedman

  McGrath Realty Inc

  (Lot 1) 111 South St, Highland, NY 12528
• 

  

  /2

  $375,000

  • Land
  • 12.97 Acres
  • $28,913 per Acre

  (Lot 4) 111 South St, Highland, NY 12528

  Build your custom dream home on this shovel-ready 13-acre homesite in a newly approved and recorded 4-lot subdivision totaling nearly 49 acres. All the hard work is done: perc test completed, well & septic approved by the Ulster County Board of Health, and electric & fiber already run to the shared driveway. Accessed via a common driveway, the lot offers privacy and a natural Hudson Valley

  

  Mark Friedman

  McGrath Realty Inc

  (Lot 4) 111 South St, Highland, NY 12528
• 

  

  /2

  $300,000

  • Land
  • 11.57 Acres
  • $25,929 per Acre

  (Lot 2) 111 South St, Highland, NY 12528

  Build your custom dream home on this shovel-ready 11.57-acre homesite in a newly approved and recorded 4-lot subdivision totaling nearly 49 acres. All the hard work is done: perc test completed, well & septic approved by the Ulster County Board of Health, and electric & fiber already run to the shared driveway. Accessed via a common driveway, the lot offers privacy and a natural Hudson Valley

  

  Mark Friedman

  McGrath Realty Inc

  (Lot 2) 111 South St, Highland, NY 12528
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  /48

  $1,200,000

  $95K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,919 Sq Ft

  15 Oakes Rd, Highland, NY 12528

  Welcome to The Riverhouse, an extraordinary custom Lindal Cedar home offering front-row living on the Hudson River.A wall of glass and voluminous ceilings frame breathtaking, ever-changing water views, filling the dramatic great room and its striking fireplace with a light-filled, airy atmosphere. The stylish chef's kitchen is both sleek and functional, featuring high-end cabinetry,

  

  Mark McAlpine

  Compass Greater New York, LLC

  15 Oakes Rd, Highland, NY 12528
• 

  /2

  $350,000

  • Land
  • 14.5 Acres
  • $24,138 per Acre

  (Lot 3) 111 South St, Highland, NY 12528

  Build your custom dream home on this shovel-ready 13-acre homesite in a newly approved and recorded 4-lot subdivision totaling nearly 49 acres. All the hard work is done: perc test completed, well & septic approved by the Ulster County Board of Health, and electric & fiber already run to the shared driveway. Accessed via a common driveway, the lot offers privacy and a natural Hudson Valley

  

  Mark Friedman

  McGrath Realty Inc

  (Lot 3) 111 South St, Highland, NY 12528
• 

  

  /3

  $469,000

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  224 Vineyard Ave, Highland, NY 12528

  Ready-To-Build 3-Bedroom Home with Mountain Views - Prime Location Near Town This won't last long ready to-built. Still time to customize the floor plan, pick colors, countertops and more. 3-bedroom, 2-bathroom home on a scenic .24-acre lot with stunning Illinois Mountain views. Perfectly situated just minutes from town, you'll enjoy close proximity to restaurants, the train station, wineries,

  

  Danielle Carlson-Murphy

  Start Home Smart, Inc.

  224 Vineyard Ave, Highland, NY 12528
• 

  

  /45

  $550,000

  $25K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,224 Sq Ft

  9 Roxanne Blvd, Highland, NY 12528

  Welcome to this beautifully maintained split-level home, offering the perfect blend of comfort, functionality, and style. Featuring 4 spacious bedrooms and 3 full bathrooms, plus an additional flex room on the lower level that can serve as a 5th bedroom, home office, or recreation space, this home provides room for everyone.Freshly painted and situated on a quiet dead-end street in one of the

  Simone Edwards Edwards Properties

  9 Roxanne Blvd, Highland, NY 12528
• 

  

  /6

  $227,000

  • Land
  • 3.9 Acres
  • $58,205 per Acre

  5 Elbow Ln, Highland, NY 12528

  Seasonal Hudson River Views. This lot was approved for an in ground septic system and engineered for a 4 bedroom home in 2011. Will need to be updated. 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

  Elizabeth Decker Hudson Dwellings Realty

  5 Elbow Ln, Highland, NY 12528
• 

  

  /11

  $350,000

  • Land
  • 7.2 Acres
  • $48,611 per Acre

  75 Palazzo Ln, Clintondale, NY 12528

  7.2 Acres of Hudson Valley Beauty with Stunning Western Views! Discover the beauty and tranquility of the Hudson Valley on this exceptional 7.2-acre parcel, offering expansive western views and spectacular sunsets. With open skies, peaceful surroundings, and a beautiful natural setting, this property provides the perfect opportunity to create a private country retreat or dream home. Located just

  Dawn Passante Coldwell Banker Village Green

  75 Palazzo Ln, Clintondale, NY 12528
• 

  

  /65

  $998,500

  Open House 9/26 $102K PRICE DROP

  • 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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  /6

  $100,000

  • Land
  • 39,204 Sq Ft
  • $111,111 per Acre

  120 Floyd Ackert Rd, West Park, NY 12493

  Just minutes from the Hudson River, this location sits in the heart of the Mid-Hudson Valley, surrounded by destination spots like John Burroughs Sanctuary, local wineries, farm markets, and a growing collection of restaurants and artisanal shops. The lot is largely level and ready to be improved, giving you a flexible canvas to adapt for retail, service, office, or other permitted uses under GC

  Dawn Passante Coldwell Banker Village GreenN

  120 Floyd Ackert Rd, West Park, NY 12493
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  /35

  $375,000

  • 2 Beds
  • 2 Baths
  • 1,760 Sq Ft

  198 S Riverside Rd, Highland, NY 12528

  CASH ONLY! Brick Ranch! 1,760 sq. ft. 2 Bedroom, 2 Full Bath, Gleaming Hardwood Floors, Updated kitchen with Jenn Air Downdraft stove, European Cabinets, SS Appliances, Kitchen with Corian counter with stools & dinette eating area with ceramic tile floors and sliding door to 6 yr old huge cedar deck, large living room with hardwood floors & large Triple picture window. Full bath on 1st floor,

  Joanne Timperio RE/MAX Benchmark Realty Group

  198 S Riverside Rd, Highland, NY 12528
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  /10

  $300,000

  • 4 Beds
  • 2 Baths
  • 1,450 Sq Ft

  87 Vineyard Ave, Highland, NY 12528

  Village of Highland two family w/two bedroom units. Hardwood floors throughout. Separate utilities with natural gas for heat & hot water. Centrally located with easy access to village amenities, commuter routes & Mid-Hudson Bridge. Attractively low taxes. Ideal for investor or owner occupant.

  Dan Axtmann BHHS Hudson Valley Properties

  87 Vineyard Ave, Highland, NY 12528
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  /46

  $525,000

  • 3 Beds
  • 3 Baths
  • 2,000 Sq Ft

  133 Bedell Ave, Highland, NY 12528

  Gorgeous 3 bedroom, 3 bath, Raised Ranch nestled away on nearly 2 acres of beautiful property found a quiet neighborhood. Large living room fills with natural light from the bay windows that highlights the new flooring throughout the main living areas. Eat-in kitchen is loaded with plenty of heavy duty cabinets and counterspace, center island with breakfast nook, and a cooktop capped with an

  Tremaine Selby Weichert Realtors

  133 Bedell Ave, Highland, NY 12528
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  /3

  $4,400,000

  • Land
  • 73.7 Acres
  • $59,701 per Acre

  00 Vineyard Ave, Highland, NY 12528

  Multi family property consisting of R-1/4, R-1/2 and R-1 zoning. Totaling 73 plus acres with two access points along Rte 44, Vineyard Avenue, in the Town of Lloyd, Ulster County, NY. One on the South end of the property with 150 feet of frontage along Vineyard Avenue and one on the North end of the property with 50 feet of frontage along Vineyard Avenue. Property slopes gently upward from road

  Robert Vitanza Rand Commercial

  00 Vineyard Ave, Highland, NY 12528
• 

  

  /49

  $697,000

  • 5 Beds
  • 6 Baths
  • 2,774 Sq Ft

  90 New Paltz Rd, Highland, NY 12528

  Grand Highland Home with Exceptional Living and Entertaining Spaces. Welcome to this stately Highland residence, proudly perched atop a beautiful knoll and offering that unmistakable feeling of coming home the moment you arrive. This grand 5-bedroom home combines spacious living, thoughtful updates, and an incredible setting designed for both everyday enjoyment and memorable entertaining. The

  Dawn Passante Coldwell Banker Village Green

  90 New Paltz Rd, Highland, NY 12528
• 

  

  /40

  $900,000

  $1K PRICE INCREASE

  • 4 Beds
  • 2.5 Baths
  • 3,002 Sq Ft

  4 Picnic Woods Rd, Clintondale, NY 12515

  Welcome to 4 Picnic Woods Road — a stunning 4-bedroom, 2.5-bath Colonial residence perfectly positioned on 1.05 acres in scenic Clintondale. With over 3,000 square feet of beautifully designed living space, this home offers elegance, space, and comfort for both everyday living and entertaining. From the moment you arrive, the striking stone-accented façade, classic symmetry, and snow-covered

  Arya Rabinovits eRealty Advisors, Inc

  4 Picnic Woods Rd, Clintondale, NY 12515
• 

  

  /13

  $500,000

  $195K PRICE DROP

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

  TBD Rt 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 Rt 9w, Highland, NY 12528
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  /24

  $84,500

  $46K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 952 Sq Ft

  1069 Route 44 55, Clintondale, NY 12515

  Step into the potential of this 952 sq ft railroad-style home, featuring 2 cozy bedrooms and 1.5 bathroom. This classic layout, known for its linear flow and vintage character, offers a unique opportunity for those looking to restore or reimagine a timeless space.While the home needs renovation, its solid structure and charming original details provide the perfect canvas for

  John Quinn Quinn Realty Group Inc.

  1069 Route 44 55, Clintondale, NY 12515
• 

  

  /10

  $75,000

  • Land
  • 7.1 Acres
  • $10,563 per Acre

  0 Crest Ln, Lloyd, NY 12528

  Rare opportunity to own a truly unique 7.1-acre parcel tucked away in the heart of Highland within a quiet, private setting between two dead-end roads—no through traffic and exceptional seclusion. This picturesque property features significant wetlands and a serene pond located near the center of the land, creating a peaceful natural environment that feels like your own private nature preserve.

  John Durso Keller Williams Realty Partner

  0 Crest Ln, Lloyd, NY 12528
• 

  

  /23

  $895,000

  • 4 Beds
  • 2.5 Baths
  • 2,961 Sq Ft

  3 Elbow Ln, Highland, NY 12528

  Experience the pinnacle of upscale country living in this stunning, newly constructed 2,961-square-foot masterpiece. Nestled on 5.4 partially wooded acres in the scenic Hudson Valley, this architectural gem offers the perfect blend of private sanctuary and modern luxury, all just moments from the historic Hudson River.As you approach, a magnificent covered front porch welcomes you, offering

  Adriane Werkema Easy Lifestyle Real Estate

  3 Elbow Ln, Highland, NY 12528
• 

  

  /50

  $750,000

  $240K PRICE DROP

  • Land
  • 215.12 Acres
  • $3,486 per Acre

  00 Rt 44 55, Clintondale, NY 12515

  This is a hard-to-find large acreage consisting of four parcels located on both sides of Route 44/55 in the hamlet of Clintondale. Being sold as one sale leaves the opportunity for investors and builders looking for their next project, or the potential for a single or multi family homestead. You can keep it all for yourself or sell off what you don't need. The largest parcel is approximately

  Clint Carlson WHITETAIL PROPERTIES REAL ESTATE LLC (NY)

  00 Rt 44 55, Clintondale, NY 12515
• 

  

  /31

  $450,000

  • 2 Beds
  • 2 Baths
  • 1,352 Sq Ft

  517 Crescent Ave, Highland, NY 12528

  Welcome to easy, one-level living in this beautifully maintained ranch home, built in 2020 and set on 1.2 peaceful acres. Offering 2 bedrooms, 2 full bathrooms, and a dedicated home office, this property combines modern comfort with the tranquility of country living. Start your mornings on the inviting front porch, the perfect spot to enjoy a cup of coffee while taking in the serene surroundings.

  Anthony DeGelormo Century 21 Alliance Rlty Group

  517 Crescent Ave, 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
• 

  

  /12

  $279,000

  • 2 Beds
  • 1 Bath
  • 1,056 Sq Ft

  76 Sunny Brook Cir, Highland, NY 12528

  ATTENTION INVESTORS, CONTRACTORS, OR SOMEONE LOOKING FOR A RENOVATION PROJECT!!! This townhouse is ready for renovations, being sold as a shell, Freshly painted, New windows, New siding, recessed lightening, New electric switches and outlets with USB plugs. This unit is a legal 2 bedroom, with potential for a 3rd bedroom, office or guest room. This unit needs flooring, kitchen and bathroom. This

  Nancy Young BHHS Hudson Valley Properties

  76 Sunny Brook Cir, Highland, NY 12528
• 

  

  /50

  $475,000

  Open Sun 12PM - 2PM

  • 5 Beds
  • 2.5 Baths
  • 2,974 Sq Ft

  1311 Route 44 55, Clintondale, NY 12515

  Welcome to this versatile Clintondale property featuring a 3-bedroom, 2-bath main home plus a separate 2-bedroom, 1-bath cottage offering outstanding flexibility for multi-generational living, guests, work-from-home needs, or potential rental income.The main home offers convenient living with a first-floor primary bedroom, cozy fireplace, sunroom, dedicated office space, and a fenced yard

  Syndi Acampora eXp Realty

  1311 Route 44 55, Clintondale, NY 12515
• 

  

  /23

  $1,250,000

  • Land
  • 4.7 Acres
  • $265,957 per Acre

  134 Bellevue Rd, Highland, NY 12528

  Spanning an expansive 4.7 acres, 134 Bellevue Road offers a rare opportunity to experience nature and simple indulgence high above the Hudson. This breathtaking, natural setting perfectly blends sweeping river vistas with immediate access to nearby rail lines and world-class outdoor adventure.Recently cleared to showcase its striking natural contours, the property offers a distinct "clean-site"

  Dominick Martorana Century 21 Alliance Rlty Group

  134 Bellevue Rd, Highland, NY 12528
• 

  

  /50

  $649,900

  • 4 Beds
  • 3.5 Baths
  • 2,627 Sq Ft

  14 Lisa Dr, Highland, NY 12528

  Set on 1.6 picturesque acres in a quiet Highland cul-de-sac, this sprawling contemporary ranch offers an exceptional combination of space, privacy, and resort-style outdoor living. Surrounded by mature landscaping and natural beauty, the property features generous living spaces, multiple bedrooms, and an inviting backyard oasis designed for both relaxing and entertaining. The main level features

  Jennifer Gold RE/MAX Benchmark Realty Group

  14 Lisa Dr, Highland, NY 12528
• 

  $510,900

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,800+ Sq Ft

  Adirondack Home Plan at Mountainside Woods, Highland, NY 12528

  Meadow Creek Development Builder

  2 Benjamin Dr Unit 42035422, Highland, NY 12528
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  /2

  $395,000

  • Land
  • 14.5 Acres
  • $27,241 per Acre

  0 Route 299 Unit KEY997500, Lloyd, NY 12528

  This commercial property consists of an 11.6 acre parcel and an adjoining 2.9 acre parcel in a with approximately 800 ft. of frontage on rte. 299. Close proximity to NYS Thruway and is relatively close to the Poughkeepsie Bridge.

  Dennis Barr John J Lease REALTORS Inc

  0 Route 299 Unit KEY997500, Lloyd, 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
• 

  

  /47

  $575,000

  • 4 Beds
  • 3 Baths
  • 2,082 Sq Ft

  16 Gabriety Rd, Highland, NY 12528

  Tucked away on a quiet street and overlooking a picturesque apple orchard, this beautifully maintained mid-century Cape offers the perfect balance of timeless character and modern convenience. Set on just under an acre with mature landscaping, the property provides a peaceful setting while remaining close to the amenities of the Hudson Valley. For commuters, the home is located just 3 miles from

  Leigh Wagner-Quintana KW Hudson Valley North

  16 Gabriety Rd, 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

Showing Results 1 - 40, Page 1 of 2