About this home
The Underhill House is an enchanting 4BR/1.5BA historic country estate, on 2 Acres in Ashfield located on a quiet road just 5 mins from Ashfield Lake, 10 mins from the DAR forest, 30 mins from Smith College, 40 mins from Amherst College and UMass, and 25 mins from Deerfield Academy. Tanglewood and Lennox are an hour away. Ashfield has over 20 miles of hiking trails. Boasting bucolic views of fields and surrounded by protected farmland, planted with tree peonies, roses, fruit trees, lilacs, and magnolia hedges, this sprawling Georgian Colonial set behind mature maple trees with a striking vintage farm silo blends classic character with modern updates and conveniences such as fiber optic internet, spacious rooms offering two entrances each and lots of light, 8 fireplaces, wood floors (maple) through out, with many original details. French doors and large windows blur indoor/outdoor lines. The heart of the home is a renovated and inviting open-concept great room with rich cherry floors, a fireplace, large windows and a kitchen featuring granite counters, copper vent hood + copper apron sink, an ample pantry/utility room, and a main-floor laundry. A flexible attached 5-room farmhand quarters above the carport/carriage shed offers endless potential, with an attached creamery converted to a garage. The covered parking area is highly functional as-is, but also perfectly situated to be reimagined as a superb screen porch or outdoor patio. This antique home (circa 1792/1829) has many already completed major updates that provide peace of mind, including cosmetics, a new slate roof over the main house, a rebuilt north chimney, updated electrical/septic/plumbing, structural improvements, and more. Already plumbed for an additional bathroom. This graceful grand home is ready for its next chapter. A golden opportunity to enjoy a generously sized home in a peaceful setting and build immediate equity while customizing a classic New England treasure.
Listing last checked: Listing updated:
Listed by Andrea C. Kwapien · Delap Real Estate LLC · MLS #73563765
Request property information
Select a document to start a request. You can add others in the form. Availability varies.
Details at a glance
Interior6 property facts
- Rooms
- 15
- Heating
- Central, Steam, Oil, Fireplace(s), Fireplace
- Cooling
- None
- Flooring
- Wood, Flooring - Wood
- Basement
- Yes · Partial, Crawl Space, Interior Entry, Bulkhead, Sump Pump, Concrete
- Fireplaces
- 8
Building6 property facts
- Style
- Single Family Residence
- Year built
- 1829
- Garage
- 2
- Parking
- 14
- Foundation
- Stone, Irregular
- Roof
- Shingle, Slate
Land & utilities5 property facts
- Lot size
- 2 acres
- Water
- Private
- Sewer
- Private Sewer
- Pool
- Not reported
- Zoning
- RRA
Financial2 property facts
- Annual taxes
- $3,131
- Assessment year
- 2026
Location
Estimated monthly cost
Explore costs at the $650,000 asking price. Adjust the assumptions to your situation.
Known monthly costs$3,548 / monthAdjust
- Principal & interest
- $3,287
- Property tax
- $261
- Insurance
- Not entered
- HOA
- Not entered
Listing annual taxes: $3,131. Initial monthly tax is one twelfth of that amount. HOA amount was not supplied.
Partial estimate: add insurance, monthly HOA to include those costs. Blank amounts are unknown.
The initial 6.5% rate is illustrative, not a current rate or lender quote. Excludes utilities, maintenance, closing costs and mortgage insurance, which may apply with a down payment below 20%. Taxes and insurance can change.
More property insights
Automated value estimate $722,779
Estimated range $663,646–$781,911.
Automated estimates are not appraisals or guarantees of market value.
Request a professional market analysisPhoto-based condition insights
Overall presentation: above average
Explore more of Ashfield
Continue your search in Ashfield.
Need help making sense of this home?
About 238 Briar Hill Rd
Can I request a private showing?
Request a tour of 238 Briar Hill Rd and a Bean Group agent will help coordinate an available time with the listing side.
Can you help me evaluate this property?
Yes. We can discuss condition, comparable sales, offer strategy and the questions worth asking before you decide whether to proceed.
Are property documents available?
Availability varies by property and source. Request the documents you need and we will help obtain what is available.

