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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740A State Route 44 55 Route Highland NY 12528-2293

MLS Number 20213165

  • Residential Single Family
  • MlsStatus BACK ON MARKET
  • Lfd Style COLONIAL
  • Property Style Contempo
  • Square Feet 3,600

This stunning 3,600 square foot custom-built contemporary colonial is sited down a long driveway, surrounded by lush and mature trees, offering the privacy and seclusion you yearn for, yet with the convenience of amenities at your fingertips. The grounds here will truly take you breath away; 13 manicured acres with a private pond and open meadow, ideal for natural walks. This desirable open concept design lends itself to entertaining or relaxation, at scale. As you walk through the front door you be greeted by a soaring two-story foyer with opening staircase and amble closet storage. The main floor was meticulously designed, with clean lines and simple spaces, the formal dining room flows flawlessly into the massive gourmet kitchen with gorgeous island, commercial-grade stainless appliances, wet bar, and plenty of working space for the chef in the family. The kitchen offers an extension of space, ideal for large gatherings, with an open living room with gleaming hardwood floors, sun-drenched natural light and gas fireplace. From there you will enter the billiard room, with a pool table and overhead lighting. The sunken great room/living room boasts a beautiful stacked stone centerpiece fireplace and plenty of space to unwind. The first floor also features two bedrooms with a full bathroom and a den/office. The entire second floor is an oversized primary bedroom suite with walk-in closets, a luxurious ensuite bathroom with double vanities, standing custom-tile shower and jacuzzi tub. The suite also offers a private laundry room. The 3-bay garage is a perfect space for a car enthusiast or just keeping your cars/equipment out of the elements. This property is truly a dream for a Hudson Valley retreat. Enjoy radiant heat throughout, central air and reverse osmosis water. Live, work and play here, with space for workshops, in-laws, and a home office. Just minutes to the Mid-Hudson Bridge, Metro North and NYS Thruway and 90 miles from NYC, this location is ideal for commuting. Come and see it for yourself, and move right into this beautiful Hudson Valley home!

Listed by Lindsay Stevens, eXp Realty,LLC

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$
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$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* 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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8 Woodside Place Highland NY 12528-1414

Highland, NY8 Woodside Place

Price$599,000

Est. Mortgage: $/month

MLS Number 20213502

  • Residential Single Family
  • Lfd Style COLONIAL
  • MlsStatus ACTIVE
  • Property Style Colonial
  • Square Feet 2,695

Welcome to 8 Woodside Place, an architecture lover's dream just 90 mins from NYC! This gracious 3 bed, 2.5 bath house also features a nursery, finished attic and, home office. Built in 1900 this estate boasts original windows, original floors, cast iron radiators original tin ceilings, stunning millwork, coffered ceilings, and butler built-ins. Around every corner, you'll appreciate the craftsmanship that has stood the test of time! Lovingly brought back to life, the current owners reclaimed the beauty and charm as well as added brand new roof, boiler, gas line, plumbing, insulation, electrical, gutters, paint, new bathrooms, kitchen, Nest thermostats, smart security doorbell, and hardwired for security cameras. Designed by an NYC interior designer each room in 8 Woodside is meant to tell a story using the 7 elements of design, space, lines, form, pattern, light, color, and texture! This unique home was crafted to accommodate modern or classical furnishings and would make for an amazing artist homestead, weekender, or Airbnb! Perfectly set on a double depth corner lot 8 Woodside features century-old trees, and mature plantings on a level lot with space to grow or wall off for your own private getaway in this up-and-coming hamlet. Located only one block from stores and restaurants and steps from the rail trail and just minutes to the Metro-North! Live, play and stay close to a plethora of breathtaking orchards, The Gunks, Mohonk Mountain House, climbing, cycling, kayaking, Minnewaska State Park, The Culinary Institute of America, the village of New Paltz, and all the beautiful Hudson Valley has to offer!

Listed by Leigh Quintana, Keller Williams Realty HV Nort

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$
%
$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* 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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189 Pancake Hollow Road Highland NY 12528

Highland, NY189 Pancake Hollow Road

Price$589,000

Est. Mortgage: $/month

MLS Number 20214294

  • Residential Single Family
  • Lfd Style CONTEMPO, FARM HOUSE
  • MlsStatus ACTIVE
  • Property Style Farm House
  • Square Feet 1,938

This 3 bedroom, 2 bathroom, contemporary farmhouse is set in beautiful Ulster County. Constructed in 2016, this home not only features tons of luxury amenities but also incorporates energy-efficient design and features; radiant heat, spray foam insulation, on demand hot water heat, central air, nest thermostats, Generac generator, interior barn doors, exposed beams and a modern cable stairway. The open floor plan boasts cathedral ceilings and wood flooring throughout as well as a gas fireplace. The kitchen has been thoughtfully designed featuring Corian counters and the current owners have updated the stove and fridge making it a chef's delight. Upstairs you'll find a landing loft, bathroom, and a spacious master bedroom which includes a spa like master bath with rain head shower. On the main level are two additional bedrooms. The home is filled with tons of natural light, creating a seamless transition between outdoors and in. The double extended deck is approximately 700 sq feet and features a Kitchen Aid BBQ grill and Softub Jacuzzi to provide maximum comfort and entertainment. The outdoor space also has an outdoor shower and fire pit. This tastefully decorated home comes fully-furnished, bringing a whole new meaning to turn-key. No need to think about furniture, appliances, garden equipment or even plates and sheets. Perfectly situated just 1h 30m from NYC while also nearby towns such as Accord, Kingston, Saugerties, Hyde Park, Rhinebeck, Woodstock and Poughkeepsie. Great food, biking, hiking, kayaking, shopping, spirits, vineyard/cider tours, drive inn movie theaters, Mohawk Mountain House, and the Culinary Institute are just a few of the local offerings. The Metro North at Poughkeepsie is just minutes away for an easy commute to the city making it an ideal weekend retreat. This property has successful airbnb rental history and can be conveyed as a fully turn-key live in or short term rental situation. Don't miss this opportunity!

Listed by Sakura Akiyama-Bowden, Corcoran Country Living

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$
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$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* 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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27 Dogwood Knoll Highland NY 12528

Highland, NY27 Dogwood Knoll

Price$580,000

Est. Mortgage: $/month

MLS Number 20214147

  • Residential Single Family
  • Lfd Style COLONIAL
  • MlsStatus ACTIVE
  • Property Style Colonial
  • Square Feet 2,776

Privacy at the end of the cul de sac! Come home to this spacious home that offers so much! There is an open floor plan in the bright light filled home. Family and guest will enjoy the open living room with a wood burning fireplace. The large kitchen has all the features the chef will love. Glass sliders lead to the backyard for easy access to BBQ. Large bedrooms are on the second floor. The master offers walkin closet and a dream bath with shower and jetted tub. The laundry is conveniently located on the second floor. Not to be missed in the large bonus room, with an additional set of stairs for private access. The large heated garage will be appreciated on cold or rainy days! The large level yard is set privately back from the road. Dont miss this incredably well built home, ready for it's new owner. Come see the attention to detail offered here.

Listed by Barbara Carter, Century 21 Alliance-NP

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$
%
$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* 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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71-79 Vineyard Highland NY 12528

MLS Number 20213223

  • Commercial Mixed Use
  • MlsStatus ACTIVE
  • Square Feet 8,665
  • Address 71-79 Vineyard
  • Year Built 1900

2 vintage buildings for the price of one. Main buildings was built as a bank when the rail road came through. Still has many original features such as light fixtures, 2 working vaults, high ceilings, safety deposit stalls, conference room and office. Adjoining building has stable tenants in use and approve as an acting school with 100 students. 2nd floor features two apartments in need of renovation. Could be residential or offices. Situated in the center of the eclectic hamlet of Highland. Easy walk to many restaurants, art galleries, and unique shops. Within walking distance of the Hudson Valley Rail Trail and Walkway over the Hudson. Also easy commute to New York City and the rest of the world by train and plane.

Listed by Elizabeth Decker, Hello Dolly Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* 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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30 WHITE Street Highland NY

MLS Number 20213458

  • Commercial Mixed Use
  • MlsStatus ACTIVE
  • Square Feet 7,216
  • Address 30 WHITE Street
  • Year Built 1980

This is a great opportunity! Two properties sold as one! This was once a thriving apple cider mill that pressed, bottled and shipped both cider and juice nationally. Pressing equipment and vats included. The main building is located in the CB zone which have a number of business uses. Restaurant, retail, warehouse, just to list a few. The second building was also part of the production process. This structure is 2,992 s, 1.3 acres. Planning board approvals needed. Perfectly located in the hamlet of Highland near famous walk way over the Hudson, rail trail and Hudson river. The potential is endless!

Listed by Toni Petfield, Century 21 Alliance-NP

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$
%
$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* 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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199 Hawleys Corners Road Highland NY 12528-2717

MLS Number 20212138

  • Residential Single Family
  • Lfd Style COLONIAL
  • MlsStatus ACTIVE
  • Property Style Colonial
  • Square Feet 1,800

Being sold fully furnished as an active Airbnb! This home is a moneymaker renting between $420-$720/night. Nestled on a quiet country road, this turnkey colonial features a large, bright, open floor-plan, and rocking chair front porch! Move seamlessly throughout the first floor featuring an open concept living/dining /kitchen spaces and powder room. Off the dining room you'll find the back deck great for summer dinners, and a mature tree canopy that surrounds the backyard, offering you maximum privacy. Head upstairs via the wide staircase to the oversized en-suite primary bedroom. This bedroom offers vaulted ceilings, large windows, and excellent storage! Down the hall there are two more large bedrooms and a full bath. Tucked away the hallways closet is a stacked washer and dryer for ease. Head down to the beautifully finished walk out basement, great for a rec-room, yoga studio, home office or guest suite. This extra space has beautiful natural light and easy access to the driveway! Centrally located close to both Highland and New Paltz town centers, the NYS Thruway, or Poughkeepsie train station.

Listed by Leigh Quintana, Keller Williams Realty HV Nort

$
$
%
$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* 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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16 Tina Drive Highland NY 12528-2425

Highland, NY16 Tina Drive

Price$499,999

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 20212700

  • Residential Single Family
  • Lfd Style COLONIAL
  • Property Style Colonial
  • Square Feet 2,466
  • Address 16 Tina Drive

Located on a quiet cul-de-sac, you will find this custom-built 2,466 SF Colonial. Set back from the road on a private 4.6 acre lot, this beautifully built 3 bedroom, 2.5-bathroom home is everything you could dream of in a country setting. Just 90-miles from NYC and minutes from the Hamlet of Highland and the center of New Paltz, life here offers world-class climbing, hiking, trail systems, farm-to-table cuisine, local wineries, a thriving art scene, and breathtaking landscapes. Built in 2004, the home is comfortable and spacious, offering a simple and desirable floorplan with sun-drenched spaces. Enter the home into the soaring two-story foyer, leading into the main living spaces featuring a formal sitting room/den, sizeable formal dining room, spacious enough to dine with family and friends from near and far, sprawling great room/family room with wood-burning fireplace insert, large country kitchen offering plenty of space for the chef in the family, with a large eat-in area. Rear doors lead to the beautifully built covered rear porch, the perfect place to dine or simply enjoy outdoor living. The ground floor also features a powder room for guests. The second story features a primary suite with an ensuite primary bathroom and a walk-in closet. Two additional bedrooms are found on the second floor with a shared second full bathroom with tub/shower. The massive unfinished bonus room and full basement both offer unbelievable storage, or potential for additional finished square footage should you desire. Two car garage, space for gardens, solar panels for energy efficiency, and plenty of opportunity for outdoor living. A stone's throw from all the amenities, yet with the privacy and seclusion you desire with Hudson Valley living.

Listed by Lindsay Stevens, eXp Realty,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* 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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163 Pancake Hollow Road Highland NY 12528

Highland, NY163 Pancake Hollow Road

Price$485,000

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 20213991

  • Residential Single Family
  • Lfd Style RAISED RANCH
  • MlsStatus Accepted offer CTS
  • Property Style Raised Ranch
  • Square Feet 1,728

Better than new! This beautiful 3 bedroom 2 bath raised ranch home with many upgrades centrally located in the desirable Highland School District is new to the market. This amazing home offers dramatic vaulted ceilings in the living, dining and kitchen and a wide open floor-plan. The kitchen, dining and living room all flow together offering great gathering and entertaining space. Lovely kitchen with wood cabinets, granite counter tops and island for all your entertaining and cooking needs. In addition, kitchen has sliding doors leading out to a huge 12x25 private back deck, a great place to start your morning or relax after a long day where you overlook your large private backyard. The master bedroom boasts a tray ceiling, full bath with a walk-in shower, and double sink as well as an over sized walk-in closet. In addition, the owners have roughed in the plumbing for a third bathroom in the lower level for when you are ready to expand and complete the family room as well have installed a full house generator which is included in this sweet home. If that wasn't enough, there is a beautiful shed for additional storage and the raking and seeding of this property are also included. Great commuter location only minutes to NYS Thruway, Metro-North Railways, Stewart InternationalAirport and all the beauty that the Hudson Valley has to offer. From hiking, biking, farmers markets, pick-your-owns, wineries, breweries, restaurants, shopping - county living at it's finest is waiting! You won't want to miss this opportunity!

Listed by John Quinn, Quinn Realty Group Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* 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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13 Hudson Lane Highland NY 12528

Highland, NY13 Hudson Lane

Price$479,999

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 20214150

  • Residential Single Family
  • Square Feet 2,700
  • Property Style Colonial
  • Lfd Style COLONIAL
  • Address 13 Hudson Lane

This Hudson Valley Colonial style home sits in a well established suburban neighborhood. Just 90-miles from NYC, this upstate New York town is the ideal place for outdoor adventures, relaxation and entertaining. This gorgeous 2700 SF colonial-style single family home is located in the safe and friendly Highland Hills community. Enter into the sun-drenched foyer with soaring ceilings and a desirable open concept. The spacious modern kitchen features a center island, stainless steel appliances, granite counter tops, eat-in kitchen area. and formal dining room. The first floor also features the spacious and inviting living room with gas fireplace, formal living room/sitting room, ground-floor den/office, laundry room and half bath. The second floor offers four generous bedrooms, including an oversized primary bedroom with walk-in closet and ensuite bathroom with double vanity, standing shower and oversized tub. The second floor also features the second full bathroom. Oversized two-car garage, massive basement, rear deck for enjoyment and relaxation, and nice rear backyard. The perfect full-time or weekend home. Minutes to the best eateries, shopping, hiking, world-class climbing and all the Hudson Valley has to offer at your fingertips.

Listed by Lindsay Stevens, eXp Realty,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* 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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29 Roxanne Boulevard Highland NY 12528

Highland, NY29 Roxanne Boulevard

Price$444,000

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 20213394

  • Residential Single Family
  • Property Style Ranch
  • Square Feet 2,269
  • Lfd Style RANCH
  • Address 29 Roxanne Boulevard

FREE Dining room set & Freezer are included in the sale. A well maintained, one level home. Enjoy the sunset over peaceful mountain views from the delightful 3 season room which comes furnished with wicker furniture. Light filled rooms are graced with 10 closets. 5 ceiling fans plus, Central AC, Bathrooms updated in 2014 and 2021. A gardener's paradise with established perennial plantings and raised bed organic vegetables gardens plus one peach and one cherry tree which produce abundant fruit. This sought after Roxanne Blvd location is conveniently located midway between the Thruway and Rt 9W on the outskirts of the eclectic hamlet of Highland. Call your favorite REALTOR to see today!

Listed by Elizabeth Decker, Hello Dolly Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* 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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30 North Rd Highland NY 12528

Highland, NY30 North Rd

Price$429,000

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 20212489

  • Residential Single Family
  • Lfd Style COLONIAL
  • MlsStatus Accepted offer CTS
  • Property Style Colonial
  • Square Feet 1,998

This Charming light filled home is not your “cookie cutter” Colonial, it has so much to offer. 2500 sq. ft. including the lower level. Rocking chair front porch, a heated four-season sunroom with vaulted ceilings which leads to a back deck for entertaining. Upstairs private master bedroom suite with a private study and skylight. A bay window in the living room, French doors in the dining room, hardwood floors, built- ins in the dining room, and living room offer plenty of storage for your fine China, wine glasses, dinner plates, a whole house fan, extra wide four-foot hallway, a beautiful stained-glass window on the first-floor bath. Two ductless mini splits for additional heating & cooling. A generator hook-up, and two attics with pull-down stairs. The Kitchen was renovated in 2015 with glass subway tiles and quartz counter tops. Vintage 1953 Tappan Deluxe gas stove, Bosch dishwasher, garbage disposal, pantry, and pocket doors. Downstairs family room with a wood/coal stove, full bath, and laundry room, and drive under garage. A few blocks to the elementary and middle schools. Close to local farms, shops, art & music, just 90 minutes north of NYC, close to NY State thruway, & metro north. Within minutes of the Hudson Valley Rail Trail, Walkway Over the Hudson, the Highland riverfront park, and the quaint hamlet of Highland. Just a short drive to Mohonk Preserve and Minnewaska Park for world class climbing and hiking.

Listed by Debra Dooley, BHHS HUDSON VALLEY PROP-NP

$
$
%
$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* 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.

Save FavoriteSchedule TourAsk A QuestionMore Details