The c.1760 Woolsey-Conklin House in Milton

  |  December 24, 2025

Calling history buffs: This c.1760 home is the Woolsey-Conklin house, built by a foundational family of Milton in Ulster County, according to the listing.

Original stone walls embedded in the exterior beautifully belie the home’s vintage.

A graceful portico marks the front entrance.

It opens to the dining/family room.

It’s got thick ceiling beams and a hefty fireplace.

The primary bedroom is just off the foyer, too.

It, too, has an enormous fireplace, which we imagine is decorative at this point.

The house has a total of four fireplaces.

The second bedroom has charming accents like this red cutout closet door.

The bathroom is modernized but could probably use an update.

The finished lower level shows off Dutch framing, with heavy ceiling beams and pillars that are whitewashed to complement the cream-colored cabinets of the kitchen.

And here’s the original cooking fireplace, now a cozy focal point, pot crane and all.

The top floor of the house is unfinished, which leads to plenty of potential possibilities.

The main-floor mudroom has its own charms, like the curved mullions in the window. Amazingly, this 265-year-old home is quite comfortable by modern standards, with upgrades including new Pella windows, a new roof,  a whole-house generator, and updates to the heating system, kitchen, and bathroom.

The 1,954-square-foot house sits on 1.3 acres in bucolic apple-orchard country not far from the Hudson River. Fjord Vineyards is a mere six-minute drive from here; a tiny bit farther gets you to Route 9W for shopping, commuting, etc. It’s listed at a surprising price of $395,000.

If the Woolsey-Conklin house in Milton is your jam, find out more about 50 Conklin Hill Road, Milton, from licensed real estate agents at Compass Greater NY, LLC.

Read On, Reader...