Highland Real Estate

Highland is a hamlet of Ulster County located along route 9W. Part of the town of Lloyd, Highland sits along the west bank of the Hudson River just across from Poughkeepsie and has about 5,600 residents. This bustling hamlet is largely residential with a tractor supply store, supermarket, restaurants, and its own middle and high schools. The Hudson Valley Rail Trail is a favorite among locals, its entrance right in the middle of Highland. Take the trail east and it turns into the Walkway over the Hudson River, where you get sweeping views of the river and farmland. Illinois Mountain Park and Franny Reese State Park both fall within Highland as well.

The property for sale in Highland ranges from pricey land plots to more affordable single family homes, plus many commercial opportunities. The homes range from renovated farmhouses to Colonials and usually have a good-sized yard to boot.

Below, browse all real estate available in Highland

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139 Crow Hill Road Highland NY 12528

Highland, NY139 Crow Hill Road

Price$2,399,000

Est. Mortgage: $/month

MLS Number 20222773

  • Land Agricultural
  • MlsStatus ACTIVE
  • Address 139 Crow Hill Road

6098Privacy, Privacy, Privacy! Create a family compound in an idyllic setting for your family for generations to come, surrounded by mountain vistas, ridgeline views, your own private lakes, and your personal apple orchard near upscale New Paltz, New York. This blissful executive property has numerous buildable spots, all with magnificent Hudson Valley views. Located just 90 minutes from New York City, this gorgeous spot is in its own world in the heart of Ulster County apple country. Enjoy the rural life yet not be far from shopping, great restaurants, bars, a college atmosphere (SUNY New Paltz), and just minutes off the New York Thruway, exit 18, New Paltz. At 140 acres, this exquisite property has approximately 7,000 existing mature apple trees and a classic red barn dating back to 1840. THIS PROPERTY IS THE PERFECT SETTING FOR YOUR OWN VINEYARD, it has perfect soil, air drainage and availability of water on which to set out a new vineyard. Nestled in a bowl shape on the other side of the ridge from Apple Greens Golf Course (holes 19-27), this property features two private, interconnected, spring-fed lakes: 5+ acres of deep lakes with good groundwater. Property has its own private gravel road, which was the public road through the area from colonial times to the 1950s. And the views… ridgeline, cliffs, Catskill mountain range, surrounded by thousands of trees, and a spectacular view of Mohonk Fire Tower. This area is heaven for climbers, golfers, skiers, lovers of nature, and anyone who wants to go at a slower pace. You'll build your evening around catching the sunset up here, all the while a short drive or train ride into the city. Buildable for multiple houses, the purchaser retains the option to continue as an operational farm. Existing worker housing can be used, improved, or removed at buyer's option. There's 70 acres of apples trees with approximately 100 trees per acre. The property is served by the local electric utility (Central Hudson), landline phone/DSL company (Verizon) , and high speed internet/cable company (Spectrum). Must be seen to be believed! This kind of property brings family together, where generations can stay in one place and not be on top of each other. It's all about family, beautiful land, and privacy. Tax records show 107 acres but the deed state there are 140 acres. Property also includes Tax ID 513200.087.003-0005-016/0000. Cost per acre is actually $17,850.00 per acre.

Listed by Frank Tangredi, Frank Tangredi Realty Company

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$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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243 Vineyard Avenue Highland NY 12528

Highland, NY243 Vineyard Avenue

Price$2,100,000

Est. Mortgage: $/month

MLS Number 20220492

  • Land Residential
  • MlsStatus ACTIVE
  • Address 243 Vineyard Avenue

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. Endless opportunities await you!

Listed by John Quinn, Quinn Realty Group Inc.

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$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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5 2 Bellevue Road Highland NY 12528

Highland, NY5 2 Bellevue Road

Price$1,499,000

Est. Mortgage: $/month

MLS Number 20223825

  • Residential Single Family
  • Square Feet 3,788
  • Lfd Style CONTEMPO
  • MlsStatus ACTIVE
  • Property Style Contempo

Completed New Construction! Interest Rates Have Gone Down! This is nearly an impossible view to find! High above the banks of the Hudson River with stunning panoramic views. This opportunity does not come by often for a new construction custom house! Views from almost every room! Quality built Energy Star / HERS Rated 3,788 sq/ft home featuring 5 bedrooms and 2.5 bathrooms. Throughout the house, you will find hardwood floors, large oversized windows, LED recessed lighting, custom moldings and sliders throughout, 10ft ceilings and 9ft basement ceilings. The main living area has an open concept with gas fireplace that is conducive to indoor-outdoor living with a wall of retractable glass that opens onto a large deck overlooking the river. The kitchen also has amazing views with custom cabinets, granite counters, stainless appliances and a large island to seat four. The second floor features an oversized high ceiling master bedroom with a private deck, large master bathroom with walk-in shower and soaking tub which overlooks the breathtaking views; three additional bedrooms, a hall bathroom and separate laundry room. The lower level features a walkout basement, large finished family room that opens up to a patio with the same amazing views and an additional bedroom. Outside you will find Hardi Plank siding, blue stone front sidewalk, Trex decking with cable railings on all three levels, plantings, sod grass and a freshly paved drive. There is even space for a pool. With all of the views this house has to offer you can still enjoy a level landscaped yard and close proximity to the Poughkeepsie Metro North Train station, NYS Thruway and Route 84. Dont let this opportunity pass you buy!

Listed by Alfred Varrone, Upstate Realty Group

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$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Tbd Route 9W Highland NY 12528

Highland, NYTbd Route 9W

Price$1,200,000

Est. Mortgage: $/month

MLS Number 20223429

  • Land Residential
  • MlsStatus ACTIVE
  • Address Tbd Route 9W

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 constructed homes and 100,000 sq. ft. of commercial space. Take advantage of this limited opportunity to develop in rapidly growing Highland.

Listed by John Quinn, Quinn Realty Group Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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0 Vineyard Avenue Highland NY 12528

Highland, NY0 Vineyard Avenue

Price$1,200,000

Est. Mortgage: $/month

MLS Number 20220424

  • Land Residential
  • MlsStatus ACTIVE
  • Address 0 Vineyard Avenue

Sprawling 73 acre lot is privately set back from the road and provides ample development options; perfect for a subdivision or your own estate! This undeveloped land features mountain views, rolling hills and mature wooded trees. Municipal water and sewer hookup available. Prime location, minutes to Mid Hudson Bridge, Poughkeepsie Train station, NYS Thruway and commuter routes. View our virtual tour!

Listed by Margaret Thorne, Keller Williams Realty HV Nort

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$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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291 Orchard Road 1-4 Highland NY 12528

Highland, NY291 Orchard Road 1-4

Price$935,000

Est. Mortgage: $/month

MLS Number 20230157

  • MultiFamily 4 Family
  • Year Built 1953
  • MlsStatus ACTIVE
  • Address 291 Orchard Road 1-4

This is a wonderful investment opportunity to own a four family home situated on private 92.3 wooded acres located just minutes from the Mid-Hudson Bridge in the charming town of Highland. A former apple farm, it is the perfect hunting and fishing retreat located less than 90 miles from Manhattan, where you will find bears, deer, fox, beavers, wild turkey, pheasants, chipmunks, possum, among other wildlife on the vast grounds, while you can fish for catfish in the gorgeous, scenic lake. Your guests may relax in any one of the four oversized apartments with private patios, and enjoy watching wildlife in a peaceful country setting. Or, you may choose to rent one or more of the four units out for a great return on investment. This is an incredible opportunity for someone to land bank while your investment pays for itself, and more! The property is located just minutes from the Mid-Hudson Bridge in the beautiful, quaint town of Highland with local boutiques, bistros, galleries and cafes. Located just 10 minutes to Poughkeepsie, MTA to NYC, 6 minutes to New Paltz. Close access (3 miles) to Rail Trail and Old Railroad Bridge across Mid-Hudson River. Perfect for owner to occupy and/or an investment. Must see opportunity!

Listed by John Quinn Jr., Quinn Realty Group Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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591-593 Route 44 55 Highland NY 12528

MLS Number 20230226

  • Commercial Mixed Use
  • MlsStatus ACTIVE
  • Year Built 1975
  • Square Feet 6,014
  • Address 591-593 Route 44 55

Located in high traffic area for residents & tourists! Across from a top-rated family resort, approximately 3 miles from the quaint hamlet of Highland which offers shopping & access to the Walkway Over the Hudson and rail trail system, and approximately 7 miles from the eclectic Village of New Paltz which offers hiking, biking, rail trails, county fairgrounds, entertainment, shopping and the SUNY New Paltz college. Close proximity to Metro North and NYS Thruway. Commercial Building has many uses but is currently setup as a Restaurant with a large kitchen for main dining area & smaller kitchen for pizzeria or take out area. Included in deed is a 5 Family House & Garage. All residential units are currently rented. This is truly the perfect opportunity for an investor or business owner!

Listed by JoAnn Ellis, Summerset Realty

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$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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3748 Us Highway 9W Highland NY 12528

Highland, NY3748 Us Highway 9W

Price$660,000

Est. Mortgage: $/month

MLS Number 20221696

  • Land Commercial
  • MlsStatus ACTIVE
  • Address 3748 Us Highway 9W

8.7 Acres zoned light business use which is mostly wooded. some permitted uses are Convenience Store, Day-care Center, Restaurant, Retail Business, etc. Please see Associated Documents for complete listing of permitted use.

Listed by John Quinn, Quinn Realty Group Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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298 South Street Highland NY 12528

Highland, NY298 South Street

Price$569,000

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 20223113

  • Residential Single Family
  • Lfd Style FARM HOUSE
  • Property Style Farm House
  • Square Feet 2,696
  • Address 298 South Street

Nestled amid wineries, breweries, apple orchards and farm markets, this completely renovated and turnkey 1890 Colonial Farmhouse will wow you! Enjoy privacy and multi-level entertaining with swim-with-a-view of the Shawangunk ridge in your gorgeous in-ground pool! Have drinks on your wonderful porch or just stroll down the road to the Gunk Haus's beer garden. Perennial gardens, a stacked stone wall, and flagstone patio make entertaining a dream, and that gorgeous barn will make a great art studio! Your well-designed kitchen features granite counters, a butcher block island, glass tile backsplash, and stainless appliances, including the farmhouse sink! The spacious family room is drenched in sunlight via a wall of windows and flows out to the patio through beautiful French doors. The hardwood living room floor is radiantly heated, and there is recessed and accent lighting throughout. The primary suite spa bath features a luxurious soaking tub, beautiful shower, granite counter, and a separate dressing room. The sunroom and attic have energy efficient foam insulation. New in 2019 are the roof, insulated siding, windows, furnace, and hot water heater. Convenient to the NYS Thruway, New Paltz, Kingston, Woodstock, the Walkway Over the Hudson, hiking trails, and world-class restaurants! Imagine, nothing to do but enjoy your new Hudson Valley home!

Listed by Catherine Boyle Cole, BHHS Hudson Valley Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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12 Woodside Place Highland NY 12528-1

Highland, NY12 Woodside Place

Price$525,500

Est. Mortgage: $/month

MLS Number 20221871

  • Residential Single Family
  • Lfd Style COLONIAL
  • MlsStatus ACTIVE
  • Property Style Colonial
  • Square Feet 2,266

Come see this lovely colonial home located in the beautiful Hamlet of Highland. This charming stucco home is situated on .18 acres. The home features 4 bedrooms, 2 full baths, spacious living and dinning area with french doors, some original hardwood flooring. There is an additional Den located off the living room with a private entrance. There is also a 145 sq ft screened in porch located off the kitchen. The home also full basement with a walk in entrance. House is located to walking distance to the heart of the Hamlet where you will find a variety of restaurants, local breweries, art gallery. A must see with a great location with walking and biking just minutes away from The Walkway Over The Hudson.

Listed by Geraldine Gaudioso, Century 21 Alliance-NP

$
$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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135-139 South Street Highland NY 12528

Highland, NY135-139 South Street

Price$479,000

Est. Mortgage: $/month

MLS Number 20223477

  • Residential Single Family
  • MlsStatus ACTIVE
  • Property Style Farm House
  • Square Feet 1,793
  • Address 135-139 South Street

Set on a site with fantastic views of the Schawangunk Mountains sits a multi-building family compound waiting for it's next owners. Imagination and TLC are needed for this home's next chapter. The 1860 3 bedroom and two bath wood and stone main house with an all weather porch next to an eat in kitchen, has views that are memorable. Sunsets are forever overlooking apple orchards and a golf course. Apple trees, a pond, a three car garage with two horse stalls, a guest house/garage with a possible apartment above, more views and a tree lined entrance path from an old mansion that was on the included lot next door make for a future of fun. The main house has been occupied by the same owner for over 6 decades. Everything works in the home but is in need of updating.. A giant stone fireplace wall in the 40 foot living room is ready for many cozy evenings. The house is vacant and the owners want to sell it “as is”. It's on 3.6 acres with views from every window. There is ample room for anything you want. This property consists of the home, 3 car garage with 2 horse stalls, a second building with an apartment upstairs and a 1 car garage under. Many apple trees, a small pond and fantastic views of the "Gunks" and golf course. Enclosed porch is 19'5 x 9'3. Needs work. Being sold "as is".

Listed by Howard Schwartz, BHHS HUDSON VALLEY PROP-KING

$
$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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40 Penny Lane Highland NY 12528

Highland, NY40 Penny Lane

Price$465,000

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 20230093

  • Residential Single Family
  • Property Style Contempo
  • Square Feet 1,776
  • Lfd Style CONTEMPO
  • Address 40 Penny Lane

Close to everything yet private! Less than 2 miles from NY State Thruway exit 18. Ride your bike or walk to the Hudson Valley Rail Trail which is less than a mile away. This contemporary styled single- level home sits on a wooded 1.40 acre private lot. There are abundant new renovations throughout. Some recent improvements include flooring, custom barn doors, updated appliances, granite countertops, glass enclosed shower and much more. Plenty of natural light floods through the cathedral windows into the spacious living area. The kitchen flows into the living area with its striking floor to ceiling fireplace. The main bedroom is generously sized and accompanied by a large attached bathroom and a spacious walk-in closet. The bonus room is perfect for a home office or yoga room. Nature abounds and it is waiting for you!

Listed by Derek Eckert, Century 21 Alliance-NP

$
$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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