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Chesterfield, MA Homes for Sale

Section Image
  • Off Bryant St, Chesterfield, MA 01012
    Off Bryant St, Chesterfield, MA 01012
    Off Bryant St, Chesterfield, MA 01012
    /4

    $321,600

    • Land
    • 201 Acres
    • $1,600 per Acre

    Off Bryant St, Chesterfield, MA 01012

    The Kingsley Lot is 201.3 acres of forest land with 6,760 feet of frontage along the federally designated Wild and Scenic Westfield River in Chesterfield, MA. There is an island in the river that is a part of this property. The property is subject to a permanent Conservation Restriction held by the Mass Div Conservation and Recreation, formerly DEM, that prohibits development and has harvesting

    Keith Ross LANDVEST

    Off Bryant St, Chesterfield, MA 01012
  • 55 Cummington Rd, Chesterfield, MA 01084
    55 Cummington Rd, Chesterfield, MA 01084
    55 Cummington Rd, Chesterfield, MA 01084
    /41

    $450,000

    • 4 Beds
    • 2 Baths
    • 2,056 Sq Ft

    55 Cummington Rd, Chesterfield, MA 01084

    Nestled in the peaceful hills of Chesterfield, this inviting 4-bedroom, 2-bath home offers the perfect blend of privacy, comfort, and country charm. Surrounded by nature in a quiet setting, the property features a flexible floor plan with a first-floor bedroom, full bath, and family room—ideal for guests, multi-generational living, or convenient single-level living. A cozy pellet stove creates a

    Stacey Silvia Lock and Key Realty Inc.

    55 Cummington Rd, Chesterfield, MA 01084
  • off Bryant St, Chesterfield, MA 01012
    off Bryant St, Chesterfield, MA 01012
    off Bryant St, Chesterfield, MA 01012
    /9

    $321,600

    • Land
    • 201 Acres
    • $1,600 per Acre

    off Bryant St, Chesterfield, MA 01012

    The Kingsley Lot is 201.3 acres of forest land with 6,760 feet of frontage along the federally designated Wild and Scenic Westfield River in Chesterfield , MA. There is an island in the river that is a part of this property. The property is subject to a permanent Conservation Restriction held by the Mass Div Conservation and Recreation, formerly DEM, that prohibits development and has harvesting

    Keith Ross LandVest, Inc.

    off Bryant St, Chesterfield, MA 01012
  • 254 Bryant St, Chesterfield, MA 01012
    254 Bryant St, Chesterfield, MA 01012
    254 Bryant St, Chesterfield, MA 01012
    /35

    $695,000

    • 5 Beds
    • 2.5 Baths
    • 2,368 Sq Ft

    254 Bryant St, Chesterfield, MA 01012

    Tucked away on a dead-end street in the foothills of the Berkshires, this thoughtfully designed Cape offers space, flexibility, and a setting that feels like a retreat. Set back on 2.73 acres with scenic views, the open floor plan invites easy everyday living and effortless entertaining. The main level features a primary suite with a private bath, walk-in closet, and its own balcony for quiet

    Aimee Tompkins Park Square Realty

    254 Bryant St, Chesterfield, MA 01012
  • 31 North Rd, Chesterfield, MA 01012
    31 North Rd, Chesterfield, MA 01012
    31 North Rd, Chesterfield, MA 01012
    /54

    $1,850,000

    • 5 Beds
    • 2.5 Baths
    • 3,464 Sq Ft

    31 North Rd, Chesterfield, MA 01012

    The equestrian elegance of this 55 acre property starts at the gated driveway. Perched on the hilltop is a fully equipped custom build multi use barn entirely heated by radiant floor heat and includes 8 14x14 stalls w/ autowaterers perfect for the breeder or veterinarian. Includes kitchenette, office, laundry and bathroom. Also included is a heated equipment shed and workshop, a heated drive

    Grace Golden EQUINE HOMES REAL ESTATE, LLC

    31 North Rd, Chesterfield, MA 01012
  • 0 Pynchon Rd Unit 73512590, Chesterfield, MA 01012
    0 Pynchon Rd Unit 73512590, Chesterfield, MA 01012
    0 Pynchon Rd Unit 73512590, Chesterfield, MA 01012
    /5

    $169,000

    • Land
    • 4 Acres
    • $42,250 per Acre

    0 Pynchon Rd Unit 73512590, Chesterfield, MA 01012

    Rare water front lot on Damon Pond. Clearing needed to obtain a year round view of the pond. Lot is perc tested, surveyed with electric service being installed.. Join the association and have access to the recreation and beach area. NO power boating but kayaking, canoeing, fishing is available to all members. 25 minutes to Northampton. Year round recreational living in a quiet private setting.

    James Molyneux Molyneux Realty

    0 Pynchon Rd Unit 73512590, Chesterfield, MA 01012
Massachusetts Hampshire County Chesterfield

Real Estate & Homes for Sale in Chesterfield, MA

Why Live in Chesterfield

Chesterfield is a hillside town in rural Hampshire County, Massachusetts. The town has a quiet atmosphere against a backdrop of forests, farms, brooks and creeks. Chesterfield sits about 35 miles north of Springfield, roughly 15 miles from Northampton, putting college-town shopping, dining and culture within arm’s reach. Russell Memorial Park adds everyday amenities like a playground, skate park, ballfield and tennis court. Winters are long and often snowy, sometimes stretching into April, but many residents lean into seasonal recreation like cross-country skiing and snowshoeing at Chesterfield Gorge Reservation and nearby Gilbert A. Bliss State Forest. Homebuyers will find farmhouses and Cape Cods on large lots, some waterfront. Dining options are limited, but include some mainstays: the Chesterfield General Store and Café and Bread Euphoria Bakery & Café. Students attend schools in the Hampshire Regional School District.

Learn more about living in Chesterfield

Frequently Asked Questions

What is the average home price in Chesterfield, MA?
Homes for sale in Chesterfield, MA have an average home price of $695,641.
How many homes have sold over the last 12 months in Chesterfield, MA?
8 homes have sold in Chesterfield, MA over the last 12 months.
What are the most popular zip codes in Chesterfield, MA?
The most popular zip codes in Chesterfield, MA include 01012, 01096, 01032, 01027 and 01098.
How much do you need to make to afford a house in Chesterfield?
The median home price in Chesterfield is $449,950. If you put a 20% down payment of $90,000 and had a 30-year fixed mortgage with an interest rate of 6.3%, your estimated principal and interest payment would be $2,230 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $96K a year to afford the median home price in Chesterfield. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Chesterfield, MA?
Chesterfield, MA has highly rated public and private schools. Some of the best schools in Chesterfield based on Niche Grades are Anne T. Dunphy School, New Hingham Regional Elementary School and Wahconah Regional High School. Browse all the schools in Chesterfield, MA to learn more.

Home Trends in Chesterfield, MA

On average, homes in Chesterfield, MA sell after 41 days on the market compared to the national average of 57 days. The median sale price for homes in Chesterfield, MA over the last 12 months is $420,000, up 20% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$420,000
Median Single Family Sale Price
$432,500
Average Price Per Sq Ft
$312
Number of Homes for Sale
3
Last 12 months Home Sales
8
Months of Supply
4.50
Median List Price
$449,950
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
20%
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