If the Ulster County lifestyle is for you, and you also require easy access to NYC, Highland real estate is a great option. Highland NY sits on the western shore of the Hudson River directly across from Poughkeepsie. Highland is known largely for its convenience to the places that surround it. Poughkeepsie is a drive across the bridge for easy access to Metro North Railroad, restaurants, shopping, and large arts venues. Once Highland was barely noticed by homebuyers who were new to the Hudson Valley, but in recent years the word is out on the hidden gems of Highland. It's becoming a bit of a Hudson Valley darling! Don't leave Highland off your list of towns to explore if you're thinking of buying real estate in Upstate NY!
Highland NY Homes
| All Listings |
Under $100,000 |
$100,000 - $200,000 |
| $200,000 - $300,000 |
$300,000 - $400,000 |
$400,000 - $500,000 |
| $500,000 - $600,000 |
$600,000 - $700,000 |
$700,000 - $800,000 |
| $800,000 - $900,000 |
$900,000 - $1,000,000 |
Over $1,000,000 |
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Commercial Sale
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0 Beds
-
0 Baths
-
348,480
SqFt
$4,500,000
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Land
-
0 Beds
-
0 Baths
-
0
SqFt
$2,100,000
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Residential
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7 Beds
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4 Baths
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5,730
SqFt
$1,235,000
↓ $160,000
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Residential
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4 Beds
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2 Baths
-
2,176
SqFt
$995,000
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Land
-
0 Beds
-
0 Baths
-
0
SqFt
$825,000
Sale Pending
![103 Vineyard Avenue, Highland]()
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Commercial Sale
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0 Beds
-
0 Baths
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4,300
SqFt
$787,000
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Land
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0 Beds
-
0 Baths
-
0
SqFt
$695,000
Sale Pending
![9 Lisa Drive, Highland]()
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Residential
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3 Beds
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2.5 Baths
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2,681
SqFt
$559,900
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Residential Income
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5 Beds
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0 Baths
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2,382
SqFt
$548,000
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Residential
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4 Beds
-
2.5 Baths
-
2,184
SqFt
$515,000
↓ $10,000
Sale Pending
Enhanced
![224 Martin Avenue, Highland]()
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Residential
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3 Beds
-
1.5 Baths
-
1,633
SqFt
$475,000
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Residential
-
4 Beds
-
2 Baths
-
2,266
SqFt
$450,000
↓ $25,000
Rocking Horse Ranch offers adventure all the year-round. Original art is on display throughout Black Creek B&B. You’ll find French Country influences at the Inn at Twaalfskill. See our list...
Visit Slabsides, home of the naturalist/author John Burroughs. Horseback riding, roller skating, skiing, dogs - the Hudson Valley Rail Trail allows many types of traffic. See our list...
Drop by the artist-run Studio 89 for some inspiration or to buy art. Promote your healthy lifestyle at Gina Marie’z. Highland Cultural Arts Studio has wonderful offerings for children. See our list...
Be part of tradition by stopping by for pick-your-own or the farm stand at Locust Grove Farm. From strawberries in early summer to pumpkins in the fall, you pick ‘em at DuBois Farms. See our list...
Bruschetta Classica, Caprese & Broccoli Rabe at the Vigneto Café. All-You-Can-Eat Pasta at the Flavorful Ladle. Caesar Salad & a Broccoli Calzone at Pomo D’Oro. See our list...
Yoga, martial arts, dance… in person & virtual… the Living Seed Yoga. Cross training, strength training, boxing… Hudson Valley Raw Athletics. Pilates tower… Pilates of New Paltz. See our list...
Order a handmade make-up kit crafted of fruits, veggies & herbs from the Farmer’s Touch. Tartans imported from the U.K. are crafted into kilts at Highland’s Kiltmaker’s Apprentice. See our list...
Explore the lovely bluff-top forest at Fanny Reese State Park. Look down on the sparkling Hudson River from Walkway Over the Hudson. See our list...
There's so much to do in Highland, NY - it can be hard to decide! Contact one of our Local Experts at . We'd love to give you our recommendation on the best things to do in Highland.
Highland properties are not far from New Paltz, which is a short drive in the other direction for easy access to SUNY New Paltz, restaurants, shopping, and arts! Highland does boast one of the major attractions in the Hudson Valley, the where you can stroll across the great river and take in the views. Highland is also home to the Highland, NY real estate tends to be varied in architectural style so you’re sure to find something to your taste - you might even find a modern chalet on a lake.... Browse the available listings above or contact an agent now.
Check out affordable Highland townhomes for sale for the ultimate in commuter convenience. Highland NY real estate single-family homes can range in price from around $275,000 for a nice cottage or ranch up to the $1.2 million price point for luxury new construction and stunning larger historic homes with Hudson River Views.
For more information about Highland homes, . We'd love to help you find your dream home!
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IDX INFORMATION IS PROVIDED EXCLUSIVELY FOR CONSUMERS' PERSONAL, NON-COMMERCIAL USE AND MAY NOT BE USED FOR ANY PURPOSE OTHER THAN TO IDENTIFY PROSPECTIVE PROPERTIES CONSUMERS MAY BE INTERESTED IN PURCHASING.
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INFORMATION COPYRIGHT 2022, ONEKEY™ MLS. ALL RIGHTS RESERVED. THE SOURCE OF THE DISPLAYED DATA IS EITHER THE PROPERTY OWNER OR PUBLIC RECORD PROVIDED BY NON-GOVERNMENTAL THIRD PARTIES. IT IS BELIEVED TO BE RELIABLE BUT NOT GUARANTEED. THIS INFORMATION IS PROVIDED EXCLUSIVELY FOR CONSUMERS’ PERSONAL, NON-COMMERCIAL USE. THE DATA RELATING TO REAL ESTATE FOR SALE ON THIS WEBSITE COMES IN PART FROM THE IDX PROGRAM OF ONEKEY® MLS
Listing information last updated on July 16th, 2025 at 9:00pm EDT.
IDX INFORMATION IS PROVIDED EXCLUSIVELY FOR CONSUMERS' PERSONAL, NON-COMMERCIAL USE AND MAY NOT BE USED FOR ANY PURPOSE OTHER THAN TO IDENTIFY PROSPECTIVE PROPERTIES CONSUMERS MAY BE INTERESTED IN PURCHASING.