Highland NY Real Estate

On the western banks of the Hudson River, at the far eastern edge of Ulster County, the small hamlet of Highland, New York (population of around 6,000 and  area barely over 5 square miles) offers a real estate market 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. View more Highland, NY real estate information.

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Highland Homes for Sale

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More About Highland NY Real Estate

Highland real estate is perched on the banks of the Hudson River and is as far east as you can go and without leaving Ulster County. Ulster’s neighboring counties are Green to the north, Delaware to the northwest, Sullivan to the west, and Orange to the south. Across the river to the east is Dutchess County, as well as the larger town of Poughkeepsie.

Highland is connected to Poughkeepsie via the Mid Hudson Bridge. 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.

Other nearby towns, communities, and settlements are West Park, Lloyd, New Paltz, Clintondale, and Milton. Most of Highland falls along U.S. Route 9W (extending north to south) and U.S. Route 44 (extending east over the river). This narrow residential corridor is sandwiched between two forested areas, one terminating at the Hudson River and the other rising westward up into the Illinois Mountain Park. 

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 for Sale in Highland NY

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.

Many of the homes in and around Highland NY are mid-sized single family homes displaying strong rural Victorian roots. These designs typically feature lap (since upgraded to vinyl) siding, large front porches (some wrap around), loft spaces and single-pane sash windows with exterior shutters. Browse real estate in Highlands, NY.

Other common home designs in Highland include mid-century suburban ranchers and split-levels, Georgian colonial, and Dutch farmhouse. Properties are also generously sized, often containing many mature trees, or backing onto scenic wooded areas. 

Older homes tend to occupy the larger properties, many of which could function as hobby-farm acreages. There are also newer developments, like Highland Hills, with many large and beautiful homes arranged along smaller lots on winding streets. Another popular development is Tano Ridge in the central-west portion of Highland.

These developments, along with the many well-kept and long-standing homes, are a testament to the desirability of the Highland real estate market. 

Things to Do in Highland NY

Highland in Ulster County, New York, is a community and area with a lot to offer both residents and visitors. For a start, the area features stunning scenery and natural spaces, like the Illinois Mountain Park, Bob Shepard Highland Landing Park, and Black Creek State Forest a short distance to the north. 

Within Highland there are many charming stores and cafes, especially around the old town center at Main Street and Route 44. This area has a number of historic buildings and is a beautiful place to spend an afternoon, either enjoying the town’s ambience, or visiting for important services, like banking or shopping for necessities.

The town also boasts some excellent community parks, many of which have high-quality sporting facilities, like the Rosemary Nardone Soccer Complex or the Highland Babe Ruth Park.

A Brief History of Highlands

Highland has a rich history as a hub of commerce, dating back to the early 1700s. 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.

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.

The Town of Highland was officially established in 1853. The later development of the Erie Railroad helped to establish Highland as something of a vacation town, within both a beautiful and serene area, and within a convenient distance of bigger urban centers. 

Highland has two sites on the National Register of Historic Places: The Brown–Ellis House and Anthony Yelverton House


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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