BEDS4
BATHS2 full 2 partial
SQUARE FEET3,105
MLS#5084665
STATUSActive
PROPERTY TYPEResidential - Single Family
SCHOOLJaffrey-Rindge Coop Sch Dst
Listing Courtesy of:
BHG Masiello Keene
Agency Phone: (570) 594-7798 Cell
Associate Name: Isabella Luhrs
Property Description
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?ideal for creative or guest use. 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.
Listing Video
Property Features
Property Type: Residential - Single Family
Basement: Bulkhead, Concrete Floor, Interior Stairs, Storage Space, Unfinished, Exterior Access, Basement Stairs
Basement: Yes
Cooling: Attic Fan, Whole House Fan
Fenced: Yes
Garage: 3 car attached
Heating: Oil, Hot Air
Home Style: Antique, Colonial, Historic Vintage
Lot Size: 5.62 Acres
Roof Type: Rolled, Shingle, Slate
Stories: 3.0
Taxes: $13,451
Year Built: 1790
Amenities
Blinds
Dining Area
Draperies
Wood Fireplace
2 Fireplaces
In-Law/ADU
Primary BR w/ BA
Natural Light
Natural Woodwork
Indoor Storage
Walk-in Closet
Wood Stove Hook-up
Programmable Thermostat
1st Floor Laundry
Walkup Attic
Barn
Building
Deck
Full Fence
Garden Space
Outbuilding
Storage
Greenhouse
Stable(s)
Feature Descriptions
Accessibility: 1st Floor 1/2 Bathroom, 1st Floor Hrd Surfce Flr, Hard Surface Flooring
Appliances: Dishwasher, Dryer, Double Oven, Wall Oven, Electric Range, Refrigerator, Washer, Water Heater
Baths 1/2: 2
Baths 3/4: 1
Baths Full: 1
Color: White
Construction: Post and Beam, Wood Frame, Vinyl Siding
Construction Status: Existing
Driveway: Circular, Gravel
Electric: 200+ Amp Service, Circuit Breaker(s)
Equipment: HW/Batt Smoke Detector, Whole BldgVentilation
Exterior: Post and Beam, Wood Frame, Vinyl Siding
Flood Zone: No
Flooring: Hardwood, Tile
Foundation: Granite, Stone
Lot: Agricultural, Country Setting, Farm, Horse/Animal Farm, Field/Pasture, Landscaped, Level, Open, Orchards, Trail/Near Trail, Wooded, Near Country Club, Near Golf Course, Near Paths, Near Shopping, Near Skiing, Near Snowmobile Trails, Near Hospital, Near ATV Trail, Near Schoo
Number of Rooms: 9
Parking: Auto Open, Storage Above, Driveway, Garage, Parking Spaces 6+, Barn, Attached
Road Frontage: 362
Roads: Public Maintained Road
Sale Inclusions: Additional Buildings, Barn, Equipment, Sugar House
Sewer: Public
Sq. Ft. Above Grade Finished: 3105
Sq. Ft. Total Finished: 3105
Total Stories: 3
Water: Public
Zoning: Residential - R2
Room Sizes
Foyer: 10.1x15 Level - 1
Living Room: 15.4x32.4 Level - 1
Office/Study: 13.7x15.6 Level - 1
Dining Room: 17.9x15 Level - 1
Kitchen: 15.9x20.1 Level - 1
Mudroom: 15.4x8.5 Level - 1
Bathroom Half: 3.1x7.6 Level - 1
Bathroom Full: 10.2x9.1 Level - 2
Bathroom Three Quarter: 8.4x6.5 Level - 2
Bathroom Half: 4.3x4.11 Level - 2
Bedroom: 13.7x12.9 Level - 2
Bedroom: 13.7x13.11 Level - 2
Bedroom: 15.4x13.8 Level - 2
Primary Bedroom: 15.4x13.3 Level - 2
Studio: 29.6x42.1 Level - 2
Local Schools
High School: Conant High School
Middle School: Jaffrey-Rindge Middle School
Elementary School: Jaffrey Grade School
School District: Jaffrey-Rindge Coop Sch Dst
Listed By / Shown By
Listed By
Agency Name: BHG Masiello Keene
Agency Phone: (570) 594-7798 Cell
Agent Name: Isabella Luhrs
TOUR THIS HOME
Choose a date and time to see 236 Main Street, Jaffrey, NH 03452.
An agent will get in touch to confirm your request shortly.
Estimate Your Payment
Estimated Payment
$ 3,134.70 per month $1,780.45 Principal & Interest $1,120.92 Property Tax $233.33 Homeowner's Insurance
Listing data compilation and photo(s) copyright © 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data Last Updated 2026-04-20 17:18:22 
236 Main Street | MLS# 5084665
This single family home located at 236 Main Street, Jaffrey, NH 03452 is currently listed for sale by BHG Masiello Keene, with an asking price of $800,000. This property was built in 1790 and has 4 bedrooms and 2 full and 2 partial baths with 3105 sq. ft. Main Street is located within the Jaffrey-Rindge Coop Sch Dst school district. Search Jaffrey real estate on www.masiellogrouprealestate.com today.