Listed by Keller Williams Realty Metro-Keene · Ben Prentice · 603-352-0514
Single Family Residence · Charlestown, NH
258 Main Street, Charlestown, NH
$949,900
$1,000,000 · changed Jul 15, 2026
Est. $4,803/mo · 20% down, 30-yr, 6.5% (Owl’s Nest Real Estate estimate, not MLS data)
- Beds
- 5
- Baths
- 3
- Sq Ft
- 4,748
- Built
- 1834
- MLS®
- #5091263
Property Description
Here's your chance at a Charlestown single-family home: 258 Main Street, priced at $949,900. Expect 5 bedrooms, 3 bathrooms and 4,748 square feet of living space. Homes like this trade on the fundamentals: space, privacy and a New Hampshire address that works year-round. Also on the sheet: a 1-acre lot, garage parking for 2 and 1834 construction. Scroll on for current photos, the complete spec sheet and this Charlestown listing's market context.
Set in the heart of the Charlestown Main Street Historic District, this exceptional 1834 home known locally as “The Stone Cottage” and featured in the National Register of Historic Places, is a rare opportunity to own one of New Hampshire’s estimated 50 surviving stone houses. Meticulously restored over an 8-year period, the home seamlessly blends historic character with thoughtful modern upgrades, and is only a stone’s throw from essential amenities. Offering 5 total bedrooms and 3 full baths, the residence showcases remarkable craftsmanship throughout, including original wide pine floors, soaring 8’10” ceilings on the main level, and an extraordinary collection of 9 working fireplaces with soapstone hearths, both original and custom. A stunning 2005 library addition features custom Douglas fir timber frame construction and connects through a hidden passageway to an expansive in-law suite with a kitchenette and separate garage access. The library also includes beautifully tiled bath with seamless shower design on the first floor, making this home ideal for multigenerational living or guest accommodations. The heated oversized 2-car garage has an interior handicap-accessible ramp, while the breezeway and two-level wraparound deck create inviting transitional living and entertaining spaces. The kitchen is equally impressive with custom cherry cabinetry, tiled flooring, a large quartz breakfast island, JennAir cooktop, and Kenmore double ovens. Additional highlights include 7-zone radiant heat throughout, pellet stove, and a beehive oven and fireplace in the basement. The walkout basement also has it’s own garage-door for toys and equipment storage. Major system updates include roof, plumbing, electrical, furnace, and insulation. This is not just a home, but a chance to own a truly one-of-a-kind piece of Historic New England.
Location Highlights
258 Main Street is a single family residence in Charlestown, New Hampshire, listed at $949,900. That works out to about $200 per square foot, for a home built in 1834. It has been on the market for 5 months.
At this latitude, Charlestown averages roughly 8.4 hours of sun a day in June and 3.6 in December.
Zoned schools in the Charleston School District: Charlestown Middle School (Middle), FallMount (High). Always confirm zoning with the district office.
Source: zoned school names are PrimeMLS listing data; distances, sun exposure and school facts are Owl’s Nest Real Estate additions (school facts from the NCES, U.S. Department of Education) — not PrimeMLS data.
Property Details
Essentials & finishes
- Bedrooms
- 5
- Total Baths
- 3
- Full Baths
- 3
- SqFt
- 4,748
- Price / SqFt
- $200.06
- Property Type
- Single Family Residence
- Year Built
- 1834
- County
- NH-Sullivan
- Town
- Charlestown, NH
- Status
- Active
- Days on Market
- 147
Primary Features
- County
- NH-Sullivan
- Property Type
- Residential
- Year Built
- 1834
- Zoning
- Center
Interior Features
- Appliances
- Dishwasher, Dryer, Microwave, Double Oven, Gas Range, Refrigerator, Washer
- Basement
- Yes
- Basement Access Type
- Interior
- Basement Description
- Concrete Floor, Exterior Entry, Insulated, Interior Entry, Storage Space, Interior Stairs, Walk-Out Access
- 1/4 Baths
- 0
- 3/4 Baths
- 0
- Cooling
- None
- Electric
- 200+ Amp Service
- Flooring
- Tile, Wood
- Heating
- Oil, Pellet Stove, Hot Water, Zoned, Radiant Floor, Boiler
- Interior Features
- Wood Fireplace, 3+ Fireplaces, In-Law/ADU, Natural Woodwork, Vaulted Ceiling(s), 1st Floor Laundry
- Rooms - Total
- 11
- SqFt-Approximate Finished Above Grade
- 4,748
- SqFt-Approximate Finished Below Grade
- 0
- SqFt Approximate Total Finished
- 4,748
- SqFt Approximate Total
- 7,107
Location Information
- School - District
- Charleston School District
- School - High
- FallMount
- School - Middle/Jr
- Charlestown Middle School
Financial Details
- Tax - Gross Amount
- $13,559
- Tax Year
- 2025
- Taxes TBD
- No
Additional
- Construction Status
- Existing
- Construction
- Stone
- Covenants
- No
- Flood Zone
- No
- Pre-Construction
- No
- Property Sub Type
- Single Family Residence
- Seasonal
- No
- Total Stories
- Two
- Surveyed
- Unknown
- Timeshare/Fractional Ownership
- No
External Features
- Color
- Stone/tan
- Driveway
- Gravel
- Exterior Features
- Deck, Porch
- Foundation
- Poured Concrete, Stone
- Garage
- Yes
- Garage Capacity
- 2
- Lot Features
- Level, Major Road Frontage, Open Lot, Sidewalks, In Town, Near Shopping
- Lot - Acres
- 1
- Lot - SqFt
- 43,560
- Parking
- Heated Garage, Parking Spaces 3 - 5
- Road Frontage Type
- Paved, Public Maintained Road
- Road Frontage
- Yes
- Road Frontage Length
- 221
- Roof
- Asphalt Shingle
- Sewer
- Public
- Utilities
- Underground Utilities
- Water Source
- Public
MLS®: PrimeMLS #5091263; Listed by Keller Williams Realty Metro-Keene · Ben Prentice · 603-352-0514
Property History
Estimated annual taxes for this property
- 2024
- $16,148
- 2023
- $15,744
- 2022
- $15,341
Source: Owl’s Nest Real Estate estimate from the list price at New Hampshire’s average effective tax rate — not PrimeMLS or town assessor data. Verify with the town assessor.
Market Data
Live snapshot computed by Owl’s Nest Real Estate from PrimeMLS IDX active listings in this town
- Active listings in Charlestown
- 27
- Average list price
- $299,017
- Price range
- $49,900 – $499,000
Mortgage Calculator
Estimate your monthly payment for this home
Estimated Monthly Payment
$6,347/ mo
- Principal & Interest
- $4,803
- Property Tax
- $1,346
- Home Insurance
- $198
Source: Owl’s Nest Real Estate estimate, not PrimeMLS data. Estimates use typical New Hampshire costs — a 1.7% effective property-tax rate, insurance at 0.25% of home value/yr, and PMI below 20% down. Actual town tax rates vary; verify with your lender and the town assessor.
Around This Property
Schools, everyday places and nearby destinations near 258 Main Street, Charlestown, NH
Assigned Schools
- Middle
- Charlestown Middle School
- High School
- FallMount
- District
- Charleston School District
Source: Google Maps Platform (Places) and Owl’s Nest Real Estate — not PrimeMLS data.
Questions About This Listing
How much does 258 Main Street cost?
258 Main Street in Charlestown, NH is listed for $949,900 on PrimeMLS.
That is about $200 per square foot of finished living space.
It came on the market on May 27, 2026.
How many bedrooms and bathrooms does 258 Main Street have?
258 Main Street in Charlestown, NH has 5 bedrooms and 3 bathrooms in 4,748 square feet of finished living space.
What type of home is 258 Main Street?
258 Main Street in Charlestown, NH is a single-family home built in 1834.
The MLS lists its style as Cape, Colonial, Farmhouse, Federal, Historic Vintage, Multi-Family, with two stories.
What town is 258 Main Street in?
258 Main Street is in Charlestown, New Hampshire 03603, in Sullivan County.
Location notes from the MLS: sidewalks, in town and near shopping.
What is the lot size of 258 Main Street?
258 Main Street in Charlestown, NH sits on 1 acres, per the MLS.
The lot is described as level, major road frontage and open lot.
It has 221 feet of road frontage (paved and public maintained road).
Zoning: Center.
The MLS lists it as outside a flood zone.
What are the annual property taxes for 258 Main Street?
Annual property taxes on 258 Main Street in Charlestown, NH are $13,559 for the 2025 tax year, per the MLS.
New Hampshire towns set their own tax rates and revalue periodically, so confirm the current bill with the Charlestown assessing office.
What heating and cooling does 258 Main Street have?
258 Main Street in Charlestown, NH is heated by oil, pellet stove, hot water, zoned, radiant floor and boiler, per the MLS.
The MLS lists no cooling system.
What are the water and sewer systems at 258 Main Street?
258 Main Street in Charlestown, NH has public water and public sewer, per the MLS.
MLS details — water: public; sewer: public.
Electric: 200+ amp service.
Other utilities: underground utilities.
Does 258 Main Street have a basement?
Yes. 258 Main Street in Charlestown, NH has a basement with interior access.
The MLS describes it as concrete floor, exterior entry, insulated, interior entry, storage space, interior stairs and walk-out access.
What are the key features of 258 Main Street?
Inside, the MLS lists these features at 258 Main Street in Charlestown, NH: wood fireplace, 3+ fireplaces, in-law/ADU, natural woodwork, vaulted ceiling(s) and 1st floor laundry.
Outside: deck and porch.
Flooring: tile and wood.
Listed appliances: dishwasher, dryer, microwave, double oven, gas range, refrigerator and washer; confirm which ones convey in the purchase agreement.
What parking does 258 Main Street have?
258 Main Street in Charlestown, NH has a 2-car garage and a gravel driveway.
Parking details: heated garage and parking spaces 3 - 5.
What school district is 258 Main Street in?
The MLS places 258 Main Street in Charlestown, NH in the Charleston School District.
Listed schools: Charlestown Middle School (middle) and FallMount (high).
School assignments can change; confirm with the district.
Is 258 Main Street still for sale?
Yes. 258 Main Street in Charlestown, NH is listed as Active on PrimeMLS (MLS #5091263).
Status can change quickly; contact us to confirm availability before you visit.
Which brokerage has 258 Main Street listed?
258 Main Street in Charlestown, NH is listed by Ben Prentice of Keller Williams Realty Metro-Keene (603-352-0514).
Owl's Nest Real Estate shows it through the PrimeMLS IDX feed; we are not the listing brokerage.
How does the price of 258 Main Street compare with other Charlestown listings?
At $949,900, 258 Main Street in Charlestown, NH is priced above the $399,000 median asking price of the 13 single-family homes for sale in Charlestown on PrimeMLS as of November 3, 2026 (this listing included).
That figure is Owl's Nest Real Estate's analysis of active listings, and asking prices are not sale prices — ask us for recent comparable sales before you make an offer.
How can I see 258 Main Street in person?
To see 258 Main Street in Charlestown, NH, use Request a Showing on this page or call Owl's Nest Real Estate at 401-648-5308.
We can show any MLS-listed home and represent you as your buyer's agent; the listing brokerage represents the seller.
Similar Listings in Charlestown
$325,000
3 bd | 2 ba | 1,579 ft²
89 West Street, Charlestown, NH
Single Family Residence
MLS® #5112794 · BHHS Verani Upper Valley
$85,000
2 bd | 1 ba | 1,224 ft²
43 Windy Acres Road, Charlestown, NH
Mobile Home
MLS® #5115626 · Century 21 Highview Realty
$59,900
0 bd | 0 ba
0 Peperes Road, Charlestown, NH
Land
MLS® #4953461 · Coldwell Banker Homes Unlimited
$49,900
0 bd | 0 ba
0 Saints Way, Charlestown, NH
Land
MLS® #4953450 · Coldwell Banker Homes Unlimited
$399,000
2 bd | 2 ba | 1,144 ft²
469 Meany Road, Charlestown, NH
Single Family Residence
MLS® #5090338 · Twin State Realty LLC
$399,900
4 bd | 3 ba | 2,485 ft²
149 Great Country Road, Charlestown, NH
Single Family Residence
MLS® #5108347 · Twin State Realty LLC

NOTE: This representation is based in whole or in part on data generated by PrimeMLS, Inc., which assumes no responsibility for its accuracy. The data relating to real estate displayed on this site comes in part from the IDX Program of PrimeMLS.
This listing data is intended 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 11/03/26.
