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Chesterfield, MA Homes for Sale

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  • 7 Sundown Dr, Williamsburg, MA 01096
    7 Sundown Dr, Williamsburg, MA 01096
    7 Sundown Dr, Williamsburg, MA 01096
    /37

    $679,000

    • 3 Beds
    • 2.5 Baths
    • 2,303 Sq Ft

    7 Sundown Dr, Williamsburg, MA 01096

    Nine wooded acres in Goshen, and a 1983 timber-frame house built into them with rare care — its frame raised from timber cut on the land. Exposed beams overhead, wood and tile underfoot, a south wall of glass that follows the light all day. Complete seclusion, yet ten minutes to Williamsburg, twenty-five to Northampton, an easy drive to the Berkshires and Tanglewood.The open main level holds an

    Agent Photo

    Jacob Wint

    William Pitt Sotheby's International Realty

    7 Sundown Dr, Williamsburg, MA 01096
  • 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
  • 3 Stage Rd, Williamsburg, MA 01096
    3 Stage Rd, Williamsburg, MA 01096
    3 Stage Rd, Williamsburg, MA 01096
    /40

    $514,900

    $14K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,781 Sq Ft

    3 Stage Rd, Williamsburg, MA 01096

    Antique Cape that has maintained its wonderful original features along with sensible enhancements for modern living. The large living room with the central chimney fireplace complex that once served as the kitchen and main heating source is the central feature of the main floor. The formal dining area and the living room and bed room share the central space. The first floor is completed by the

    James Molyneux Molyneux Realty

    3 Stage Rd, Williamsburg, MA 01096
  • 31 North Rd, Chesterfield, MA 01012
    31 North Rd, Chesterfield, MA 01012
    31 North Rd, Chesterfield, MA 01012
    /41

    $1,850,000

    $100K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 3,494 Sq Ft

    31 North Rd, Chesterfield, MA 01012

    The equestrian elegance of this property starts at the gated driveway. Perched on the hill is a fully equipped custom built multi use barn entirely heated by radiant floor heat & includes 8 stalls w/auto waterers perfect for breeders or veterinarian. Includes kit, office, W&D & bath. Also included is a heated equip shed and workshop, heated drive through aisle for large trucks, wash stalls &

    Grace Golden Alex Anthony R.E.

    31 North Rd, Chesterfield, MA 01012
  • 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
    /36

    $685,000

    $10K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 2,368 Sq Ft

    254 Bryant St, Chesterfield, MA 01012

    Escape the ordinary and discover a home designed to adapt to your lifestyle. Nestled on 2.73 private acres this spacious Cape blends comfortable everyday living with endless possibilities. The inviting layout features a first-floor primary suite, granite kitchen, dedicated home office, and generous gathering spaces. Upstairs, four additional bedrooms and a separate bonus area with its own garage

    Aimee Tompkins Park Square Realty

    254 Bryant St, Chesterfield, MA 01012
  • 54 Bray Rd, Pelham, MA 01002
    54 Bray Rd, Pelham, MA 01002
    54 Bray Rd, Pelham, MA 01002
    /41

    $227,000

    Open Sun 11AM - 1PM $23K PRICE DROP
    • 4 Beds
    • 1 Bath
    • 945 Sq Ft

    54 Bray Rd, Pelham, MA 01002

    NEW PRICE! Freshly cleaned out and ready for your vision, this year-round Lake Damond waterfront home offers a clean slate for its next owner. Loved by the same family for generations, the property features 125 feet of direct lake frontage, a dock, three outbuildings, and access to the association’s private beach and playground. The main level includes an open living, dining, and kitchen area

    Shelly Hardy Brick & Mortar Northhampton

    54 Bray Rd, Pelham, MA 01002
  • 0 Bray Rd, Chesterfield, MA 01012
    0 Bray Rd, Chesterfield, MA 01012
    0 Bray Rd, Chesterfield, MA 01012
    /8

    $69,900

    $10K PRICE DROP
    • Land
    • 12,196 Sq Ft
    • $249,643 per Acre

    0 Bray Rd, Chesterfield, MA 01012

    Peaceful waterfront getaway on beautiful Damon Pond! Rare opportunity to own a private recreational retreat with approx. 130’ of frontage on this scenic 82-acre pond known for its quiet coves, islands, inlets, and natural beauty. Camp, fish, kayak, canoe, swim, or simply unplug and relax by the water. Dock already in place for easy access. Property was previously used as a seasonal camping

    Melissa Stevens Coldwell Banker Community REALTORS®

    0 Bray 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

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 $620,362.
Are home prices dropping in Chesterfield?
Yes, home prices in Chesterfield are down 10% in the last 12 months.
How many homes have sold over the last 12 months in Chesterfield, MA?
6 homes have sold in Chesterfield, MA over the last 12 months.
What is the average household income in Chesterfield, MA?
The average household income in Chesterfield, MA is $104K.
What are the most popular zip codes in Chesterfield, MA?
The most popular zip codes in Chesterfield, MA include 01012, 01096, 01002, 01098 and 01027.
How much do you need to make to afford a house in Chesterfield?
The median home price in Chesterfield is $444,500. If you put a 20% down payment of $88,900 and had a 30-year fixed mortgage with an interest rate of 6.65%, your estimated principal and interest payment would be $2,280 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $98K a year to afford the median home price in Chesterfield. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Chesterfield is $104K.
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 Prices in Chesterfield, MA

The median home sale price in Chesterfield, MA is $357,500, down 16% year-over-year. Homes in Chesterfield sell in 71 days on average, compared to the national average of 55 days.

Home Price Trends

Median Sale Price
$357,500
Median Single Family Sale Price
$420,000
Median 2 Bedroom Sale Price
$300,000
Average Price Per Sq Ft
$301
Number of Homes for Sale
2
Last 12 months Home Sales
6
Months of Supply
4.00
Median List Price
$444,500
Median Change From 1st List Price
9%
Median Home Sale Price YoY Change
-16%
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