50 Conklin Hill Road

Milton NY 12547

1954 sq. ft.

56628 sq. ft.

Single-Family

Last sold for $390,000

Callie Brennan, last sold this property on 18 February 2026 after -30 days on market.

Overview

Welcome to the Woolsey-Conklin house - a living piece of Hudson Valley history built in 1760 by one of the foundational families of Marlboro. This English Colonial has been preserved to honor its historical integrity and updated for today's world. Classic features of colonial craftsmanship, including a steep side-gabled roof and center-hall layout, welcome you at both the front and rear entrances. Inside, original wide-plank red pine floors, four fireplaces, hand-hewn beams, and finely preserved trim reflect more than 260 years of American domestic life. The finished walk-out basement, once used to store provisions through long Hudson Valley winters, showcases Dutch-style framing with long, continuous beams—a rare and enduring structural hallmark of 18th-century architecture. The unfinished second floor (approx. 600 sq ft.) provides an opportunity to expand your living space while honoring the original design. Upgrades have been undertaken with great care to maintain the home's authenticity. These include new Pella architectural windows, a whole-house generator, a new roof, and updates to the heating system, kitchen, and bathroom. This home is a canvas for your storybook vision - a unique opportunity to live in history without sacrificing comfort or convenience. Outside, follow the stone pathways and enjoy a meditative walk through the fairytale gardens brimming with thoughtfully curated native flowers and shrubbery. Set on 1.3 acres, you'll still have plenty of space to add your own magic. This historical artifact is tucked into the rolling countryside of Marlboro, a town dedicated to preserving the agrarian lifestyle the Woolseys and Conklins knew. You'll find no shortage of outstanding provisions - pick your own at Weeds Orchard, sip local wine at Fjord Vineyards and Glorie Winery, grab veggies for dinner at Overlook Farms and the Marlboro farmer's market. And do not miss a show at the renowned Falcon music venue! This home is a quick drive to New Paltz, Beacon, Gardiner — each offering some of the best dining, wining, breweries, and outdoor activities in the region. Metro-North trains are just 15 (Poughkeepsie) and 25 (Beacon) minutes away, and only 65 miles from the George Washington Bridge. The Woolsey-Conklin house awaits its next steward.

Features

3 bedrooms

1 bathroom

1954 sq. ft. floor area

56628 sq. ft. lot size

Single-Family

Estimated Value

Based on this property and similar 3 bedroom single-family properties sold in Milton over the last 12 months, the estimated median property value of 50 Conklin Hill Road is $420k.

Median value

$420k

Estimated value range

$158.5k - $659k

Median days on market

Estimated value trend

-14%

decrease over the last 12 months

Average days on market is based on recent, comparable sales in Milton. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 50 Conklin Hill Road

2026

Sold

$390,000

18 Feb 2026 by Callie Brennan, of Compass Greater NY, LLC

2022

Sold

Undisclosed

10 Mar 2022 by Brian Woolsey

Happy sellers in Milton

We have insufficient information to provide an overview of customer satisfaction for Milton. Viewing the agent profiles, reviews and sales for Milton can provide insights for this location.