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236 Main St

Jaffrey NH 03452

4
4
3
5505 sq. ft.
244807 sq. ft.
Single-Family
Currently for sale - view listing

Overview

The Captain Gilmore House - Steeped in history and rich in character, this c.1768 center-hall Colonial offers a rare opportunity to own a home with direct ties to the American Revolution. Once owned by Captain Roger Gilmore, a veteran of the Battle of Bunker Hill, the property also served as an early meeting place for town Selectmen, placing it at the very heart of Jaffrey, New Hampshire’s civic beginnings. Lovingly cared for by both current and past stewards, this remarkable home welcomes you through a grand front door into an impressive foyer. Inside, the home showcases timeless craftsmanship with 10-foot ceilings, hand-carved woodwork, & a working fireplace that evokes its 18th-century origins. Thoughtfully preserved & updated, featuring 4 bedrooms, 4 baths, pegged hardwood floors, expansive living & dining rooms, a first-floor study, & walk-up attic offering exceptional potential for additional finished space. A light-filled kitchen connects seamlessly through a breezeway to an attached 3-car garage with a finished studio above. Set on over five picturesque (5.62ac), horse-friendly acres, the grounds offer fenced pasture, classic New England stone walls, & mature maple trees that provide both brilliant autumn color and sap for the property’s vintage sugar house. A 5-stall barn with hayloft anchors the rear of the property, while a freestanding conservatory presents a unique restoration opportunity. A singular offering where history, character, & modern livability converge. Recent updates include a thoughtfully updated chef’s kitchen, a remodeled powder room, refreshed bathrooms throughout, new fencing with full pasture enclosure, interior paint throughout and more. Rich in history with original details reflecting a level of craftsmanship that has become increasingly rare—& simply can’t be replicated today. Located just moments to Jaffrey’s town center, approx. 1.5 hrs to Boston and 4 hrs to NYC. Pre-inspected & move-in ready. *SELLER ACCEPTING BACK-UP OFFERS*

Features

4 bedrooms
4 bathrooms
3 carspaces
3 garage spaces
5505 sq. ft. floor area
244807 sq. ft. lot size
Single-Family

Property history for 236 Main St

2025
Sold
$763,000
15 Aug 2025 by Matthew Cabana, of EXP Realty
2022
Sold
$450,000
30 Sep 2022 by Stephanie Murphy, of Keller Williams Realty-Metropolitan

Happy sellers in Jaffrey

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Local market activity for 4 bedroom single-family properties in Jaffrey

In the last 12 months, 9 four-bedroom single-family properties similar to 236 Main St, have been sold.

This represents a 48% increase in four-bedroom single-family properties sales when compared to the previous 12 months.

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