Highland NY Real Estate

The little hamlet of Highland (population barely over 5,000; area barely over 5 square miles) 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


Price: $787,500
City: Highland
Beds: 3
Baths: 2
Type: Single Family
MLS ID: 20113976

Wow This 16 Acre Property Features A 3 Bedroom 2 Bath Raised Ranch Home Nestled Among Hemlocks, Mature Trees And Fabulous Landscape A Gorgeous...

Price: $699,000
City: Highland
Beds: 4
Baths: 3
Type: Single Family
MLS ID: 20113525

Amazing Privacy And Hudson River Views From This Nearly New, Custom Home. An Architectual Delight Mahogany Porch Surrounds The Entire 1st Floor...

Price: $599,000
City: Highland
Beds: 4
Baths: 2
Type: Single Family
MLS ID: 20112319

Beautiful Comtempory Ranch On Hudson Riverexclusive Ranch With Priceless Waterviews Spectacular Paneramic Waterview Of The Hudson. 1900 Sq. Ft...

Price: $595,000
City: Highland
Beds: 4
Baths: 1
Type: Single Family
MLS ID: 20114553

This Grand Victorian Home Built In 1874 Was Known As Lakeledge And Was Heralded As The "Gem Of The Highland Homesteads". The Original...

Price: $575,000
City: HIGHLAND
Beds: 3
Baths: 1
Type: Single Family
MLS ID: 20114954

This House Was Restored With Impecable Detail, 1790's Saltbox Farmhouse With Separate Guest House. Very Private 4.5 Acres With Land On Both Sides...


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More About Highland Real Estate

Perched on the banks of the Hudson River – as far east as you can go and still be in Ulster County – Highland has a history as a hub of commerce that 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 – 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, Highland NY real estate was part of New Paltz to the west, until it become 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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