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7786 S Main Street

Pine Plains, NY 12567 · Dutchess County

Beds
4
Baths
1.5
Sqft
3,072
Status
Active
On site
8 days

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About this home

A true treasure and piece of Pine Plains history, this elegant circa-1903 residence offers an exceptional blend of historic character, architectural detail, and extraordinary potential. Boasting over 3,000 square feet, four bedrooms, and 1.5 baths, the home showcases generously proportioned rooms, soaring ceilings, original woodwork, pastel tile and classic period trim that speak to its enduring charm. Once home to the village pharmacy and library, this remarkable property carries a unique legacy, ready to be thoughtfully restored and elevated. Set on approximately 0.47 acres, the grounds include a lofted barn offering a wealth of possibilities for a studio, workshop, or additional storage. Lovely fenced yard with plenty of space for a garden, your pets and entertaining al fresco. Perfectly positioned in the heart of Pine Plains, the property offers a quintessential Hudson Valley lifestyle, with shops, bookstores, restaurants, and local amenities just steps away. Everyone will want to come visit with Stissing House across the street. Convenient to Red Hook, Rhinebeck, and Millbrook this is an exceptional canvas for the engaged buyer seeking historic authenticity, character, and the opportunity to create something truly extraordinary on a gem property in a Hallmark like Village setting.

Listed with Mondello Upstate Properties · Chelsea Seiler · Source: OneKey MLS

One Key MLS

Information provided by One Key MLS, and is deemed reliable but not guaranteed accurate. Data last updated: Oct 23, 2026, 7:07 AM ET. ©2026 One Key MLS.

Estimate your monthly payment

Estimate your mortgage payment, including the principal and interest, taxes, insurance, HOA, and private mortgage insurance.

$2,909.19Total / mo

Estimated monthly payment

Principal & interest
$2,093.44(72.0%)
Taxes
$615.75(21.2%)
Insurance
$200.00(6.9%)

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 Pine Plains, NY

Current listings

New in the last 30 days

6

Oct 2026

Average price

Active listings

$2,134,528

Oct 2026

Average days on market

Active listings

164 days

Oct 2026

Computed from 33 active OneKey MLS listings in Pine Plains, NY.

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