Highland NY Real Estate

Highland, NY real estate is set in a little hamlet (population barely over 5,000; area barely over 5 square miles) that manages to balance some of the historic charm of rural Ulster with the commuting convenience of a bedroom community and the lure and lore of a classic old-time commercial river town.

See below to continue reading about real estate in Highland NY, or view available listings in Highland.

Highland Homes for Sale

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
73 Properties Found. Page 1 of 13.
Photo of Listing #20203373

139 Crow Hill Road, Highland


MLS® # 20203373

Ulster County Board of Realtors Logo
Photo of Listing #20210008

Bellevue Road, Highland

$1,800,000 - 5 Beds, 3 Baths, 3,788 Sf

MLS® # 20210008

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Photo of Listing #20211247

690 New Paltz Road, Highland

$1,695,000 - 4 Beds, 4 Baths, 4,822 Sf

MLS® # 20211247

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Photo of Listing #20204027

106 Bellevue Road, Highland

$1,250,000 - 3 Beds, 4 Baths, 4,028 Sf

MLS® # 20204027

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Photo of Listing #20211148

135 Perkinsville Road, Highland

$1,199,000 - 4 Beds, 6 Baths, 4,427 Sf

MLS® # 20211148

Ulster County Board of Realtors Logo
Photo of Listing #20211143

140 North Road, Highland


MLS® # 20211143

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More About Highland Real Estate

Highland real estate is perched on the banks of the Hudson River and is as far east as you can go and with out leaving Ulster County. Homes for sale in Highland are a part of a rich history.  The town's history as a hub of commerce, dates back to the early 1700's. By then it had already grown central enough to the area's economy that a ferry across the river from Highland to Poughkeepsie had to be started, and quickly had plenty of business.

Today, the Mid-Hudson Bridge serves the same purpose. At just over a half-mile in length (a bargain one dollar to cross – charged only in the eastbound direction!), it makes possible an easy, small-town life in Highland for commuters to Poughkeepsie who can be at their “big-city” desks before the morning coffee in their travel mugs from home gets cold. And back to their Highland home again at night before the evening news.

Major thoroughfares run both ways through Highland real estate – Route 9W north-south, and Routes 44 and 55 east-west from the busy bridge – so there's no lack of commercial development in the hamlet and surrounding area. But for those willing to take a short drive to the west or south, the apple orchards, farm stands, and “country calm” of the rest of Ulster are not that far away. And for weekday commuters who relish their weekend “river watching,” this unassuming spot at the foot of the Mid-Hudson Bridge has it all.

Homes in Highland

Historically, homes in Highland were a part of New Paltz to the west, until it became so prosperous and impressed with its own booming riverfront commerce that it split off in 1845. But there are still more similarities than differences between the hamlet of Highland and the Village of New Paltz. Real estate in Highland varies from entry-level to deluxe, and you'll see many townhomes and condos, along with pockets of charming farmhouses and Victorians. Taxes are average to high-average, by Ulster standards.


If at any time you have questions about real estate in Highland or the surrounding Ulster County area, please don’t hesitate to contact Dylan Taft, Principal Broker/Owner, Taft Street Realty, Inc. - 845.687.9292 office or 845.380.3394 mobile.

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Ulster County Board of Realtors Logo The data relating to real estate on this website comes in part from the IDX of the Multiple Listing Service of Ulster County, Inc. Real estate listings held by brokerage firms other than Taft Street Realty Inc are marked with IDX logo and the detailed information about them includes the name of the listing broker.

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