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287 Derby Road

Middletown, NY 10940 · Orange County

Beds
4
Baths
1.5
Sqft
2,336
Status
Active
On site
31 days

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About this home

A place to put down roots, spread out and create the country lifestyle you’ve been dreaming of. Set on 14 mature acres in the Pine Bush School District, this circa-1850s Colonial is a property filled with character and history. The four-bedroom, approximately 2,600-square-foot home welcomes you with a charming covered front porch and retains wonderful original details, including hardwood floors, a beautiful staircase and exposed beams—all surrounded by mature trees and an established country landscape. Outside is where this property truly comes to life. Imagine horses grazing, an expansive vegetable and flower garden, evenings beneath the trees, or simply having the space to enjoy the outdoors at your own pace. The impressive two-story barn offers garage space, extensive storage and tremendous versatility for horses of other livestock, a workshop, equipment, car collection, hobbies or other pursuits. Adding even more flexibility is a separate approximately 840-square-foot one-bedroom house—an ideal setup for extended or multigenerational living, guests, or a private workspace. With 14 acres, multiple buildings and a setting that feels established rather than newly created, this is the kind of property that can evolve with its next owner. Bring the horses, plant the garden, fill the barn with your projects and make this special piece of the Hudson Valley your own.

Listed with RE/MAX Benchmark Realty Group · Patricia M Sassi · Source: OneKey MLS

One Key MLS

Information provided by One Key MLS, and is deemed reliable but not guaranteed accurate. Data last updated: Nov 2, 2026, 1:08 PM ET. ©2026 One Key MLS.

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$4,841.43Total / mo

Estimated monthly payment

Principal & interest
$3,448.02(71.2%)
Taxes
$1,193.42(24.7%)
Insurance
$200.00(4.1%)

Representative rates

Representative rates only, indicative for comparison. Edit the interest rate for your own quote; your lender’s numbers vary with credit, points, and insurance.

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Market insights

The market around Middletown, NY

Current listings

New in the last 30 days

80

Nov 2026

Average price

Active listings

$538,776

Nov 2026

Average days on market

Active listings

154 days

Nov 2026

Computed from 334 active OneKey MLS listings in Middletown, NY.

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