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*
Closed
Listed by: BHG Masiello Keene
Bought with: EXP Realty
$800,000
236 Main Street, Jaffrey, NH 03452
4beds
3,105sqft
Single Family Residence
Built in 1790
5.62 Acres Lot
$800,100 Zestimate®
$258/sqft
$3,567 Estimated rent
Home value
$800,100
$736,000 - $872,000
$3,567/mo
Zestimate® history
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List your homeWhat's special
Working fireplaceFenced pastureHand-carved woodworkFreestanding conservatoryRefreshed bathrooms throughoutRemodeled powder roomFirst-floor study
Zillow last checked:
Listing updated:
Listed by:
Isabella S Luhrs,
BHG Masiello Keene 603-352-5433,
Roger Doyon,
BHG Masiello Keene
Bought with:
Julie Emerson
EXP Realty
Source: PrimeMLS,MLS#: 5084665
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 4
- Full bathrooms: 1
- 3/4 bathrooms: 1
- 1/2 bathrooms: 2
Heating
- Oil, Hot Air
Cooling
- Attic Fan, Whole House Fan
Appliances
- Included: Dishwasher, Dryer, Double Oven, Wall Oven, Electric Range, Refrigerator, Washer, Water Heater
- Laundry: 1st Floor Laundry
Features
- Dining Area, Primary BR w/ BA, Natural Light, Natural Woodwork, Indoor Storage, Walk-In Closet(s), Programmable Thermostat
- Flooring: Hardwood, Tile
- Windows: Blinds, Drapes
- Basement: Bulkhead,Concrete Floor,Interior Stairs,Storage Space,Unfinished,Exterior Entry,Basement Stairs,Interior Entry
- Attic: Walk-up
- Number of fireplaces: 2
- Fireplace features: Wood Burning, 2 Fireplaces, Wood Stove Hook-up
Interior area
- Total structure area: 5,505
- Total interior livable area: 3,105 sqft
- Finished area above ground: 3,105
- Finished area below ground: 0
Property
Parking
- Total spaces: 6
- Parking features: Circular Driveway, Gravel, Auto Open, Storage Above, Driveway, Garage, Parking Spaces 6+, Barn, Attached
- Garage spaces: 3
- Has uncovered spaces: Yes
Accessibility
- Accessibility features: 1st Floor 1/2 Bathroom, 1st Floor Hrd Surfce Flr, Hard Surface Flooring
Features
- Levels: 3
- Stories: 3
- Exterior features: Building, Deck, Garden, Storage
- Fencing: Full
- Frontage length: Road frontage: 362
Lot
- Size: 5.62 Acres
- Features: Agricultural, Country Setting, Farm, Horse/Animal Farm, Field/Pasture, Landscaped, Level, Open Lot, Orchard(s), 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 School(s)
Details
- Additional structures: Barn(s), Outbuilding, Greenhouse, Stable(s)
- Parcel number: JAFFM237B10L1
- Zoning description: Residential - R2
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Antique,Colonial,Historic Vintage
- Property subtype: Single Family Residence
Materials
- Post and Beam, Wood Frame, Vinyl Siding
- Foundation: Granite, Stone
- Roof: Rolled/Hot Mop,Shingle,Slate
Condition
- New construction: No
- Year built: 1790
Utilities & green energy
- Electric: 200+ Amp Service, Circuit Breakers
- Sewer: Public Sewer
- Utilities for property: Cable Available, Fiber Optic Internt Avail
Community & neighborhood
Security
- Security features: HW/Batt Smoke Detector
Location
- Region: Jaffrey
Price history
| Date | Event | Price |
|---|---|---|
| 5/22/2026 | Sold | $800,000$258/sqft |
Source:  PrimeMLS #5084665 Report a problem | ||
| 4/21/2026 | Listed for sale | $800,000+0.1%$258/sqft |
Source: PrimeMLS #5084665 Report a problem | ||
| 3/23/2026 | Listing removed | $799,000$257/sqft |
Source: PrimeMLS #5076173 Report a problem | ||
| 3/9/2026 | Price change | $799,000-2%$257/sqft |
Source: PrimeMLS #5076173 Report a problem | ||
| 2/10/2026 | Listed for sale | $815,000+6.8%$262/sqft |
Source: PrimeMLS #5076173 Report a problem | ||
| 8/15/2025 | Sold | $763,000+1.8%$246/sqft |
Source: PrimeMLS #5043701 Report a problem | ||
| 7/7/2025 | Price change | $749,500-5.7%$241/sqft |
Source: PrimeMLS #5043701 Report a problem | ||
| 5/30/2025 | Listed for sale | $795,000+76.7%$256/sqft |
Source: PrimeMLS #5043701 Report a problem | ||
| 9/30/2022 | Sold | $450,000-14.9%$145/sqft |
Source: PrimeMLS #4908834 Report a problem | ||
| 8/16/2022 | Contingent | $529,000$170/sqft |
Source: PrimeMLS #4908834 Report a problem | ||
| 5/25/2022 | Price change | $529,000-3.6%$170/sqft |
Source: PrimeMLS #4908834 Report a problem | ||
| 5/9/2022 | Listed for sale | $549,000+52.5%$177/sqft |
Source: PrimeMLS #4908834 Report a problem | ||
| 11/1/2018 | Listing removed | $360,000$116/sqft |
Source: Despres and Associates, Inc. #4691170 Report a problem | ||
| 5/8/2018 | Listed for sale | $360,000+2.9%$116/sqft |
Source: Despres and Associates, Inc. #4691170 Report a problem | ||
| 8/16/2016 | Listing removed | $349,900$113/sqft |
Source: 2519-10 #4489251 Report a problem | ||
| 6/28/2016 | Pending sale | $349,900$113/sqft |
Source: 2519-10 #4489251 Report a problem | ||
| 5/14/2016 | Listed for sale | $349,900+133.3%$113/sqft |
Source: 2519-10 #4489251 Report a problem | ||
| 8/20/2001 | Sold | $150,000$48/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $12,635 -1.6% | $385,200 |
| 2023 | $12,846 +7.7% | $385,200 |
| 2022 | $11,933 +11.1% | $385,200 |
| 2021 | $10,743 +1.3% | $385,200 |
| 2020 | $10,605 -5.6% | $385,200 +19.4% |
| 2019 | $11,233 +5.5% | $322,500 |
| 2018 | $10,643 -11% | $322,500 -11.1% |
| 2017 | $11,962 -0.1% | $362,800 |
| 2016 | $11,972 -0.7% | $362,800 |
| 2015 | $12,052 +6.5% | $362,800 -5.6% |
| 2014 | $11,320 +1.2% | $384,384 |
| 2013 | $11,186 +6.6% | $384,384 |
| 2012 | $10,498 -0.2% | $384,384 |
| 2011 | $10,521 +1.6% | $384,384 |
| 2010 | $10,359 +3.8% | $384,384 -2.4% |
| 2008 | $9,980 +22.9% | $393,706 |
| 2005 | $8,118 | $393,706 |
Find assessor info on the county website
Neighborhood: 03452
Nearby schools
GreatSchools rating
- 3/10Jaffrey Grade SchoolGrades: PK-5Distance: 1 mi
- 4/10Conant Middle High School (M)Grades: 6-8Distance: 1.4 mi
- 9/10Conant High SchoolGrades: 9-12Distance: 1.4 mi
Schools provided by the listing agent
- Elementary: Jaffrey Grade School
- Middle: Jaffrey-Rindge Middle School
- High: Conant High School
- District: Jaffrey-Rindge Coop Sch Dst
Source: PrimeMLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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- New Hampshire
- Cheshire County
- Jaffrey
- 03452
- 236 Main Street
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