Chesterfield, MA Homes for Sale

/42
$665,000
- 3 Beds
- 2.5 Baths
- 2,303 Sq Ft
7 Sundown Dr, Williamsburg, MA 01096

Buyer's cold feet is your 2nd chance! This magical Cottage on over 9 acres offers privacy and many options for year-round relaxation and enjoyment of nature! Relax in the 2 saunas, cozy sun-filled reading nook, large family room, screened porch or 3rd story octagonal "meditation/yoga" turret, where you can take in the 360 degree views and a variety of wildlife! The open floor plan between

Mark Carmien

Brick & Mortar Northhampton

(413) 307-4092

7 Sundown Dr, Williamsburg, MA 01096
/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
/41
$749,900
- 5 Beds
- 2.5 Baths
- 2,368 Sq Ft
254 Bryant St, Chesterfield, MA 01012

Meticulously built custom home in a beautiful country setting, nestled among mature trees offering exceptional privacy. This spacious property features an open living room/dining set up which opens to a sun-soaked Trex deck. A cozy first-floor office/den provides flexible living space with beautiful natural light. The gorgeous kitchen features rich hickory cabinetry, gleaming granite countertops,

Molly Gold Canon Real Estate, Inc.

254 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
/25
$195,000
- 2 Beds
- 1 Bath
- 754 Sq Ft
204 Ireland St, West Chesterfield, MA 01084

This is a nice older cottage with a nice location and yard. Needs some updating but the nice surroundings and on one of the loveliest roads in the hill towns. The Chesterfield Gorge Reservation and the Chesterfield Bend swimming area are maybe a mile away. So come have a look, prices to sell.

James Molyneux Molyneux Realty

204 Ireland St, West Chesterfield, MA 01084
/5
$179,000
- Land
- 4 Acres
- $44,750 per Acre
0 Pynchon Rd Unit 73402258, 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 contracted to be delivered this summer. Join the association and have access to the recreation and beach area. NO power boating but kayaking, canoeing, fishing. 25 minutes to Northampton. Year round recreational living in a quiet private setting.

James Molyneux Molyneux Realty

0 Pynchon Rd Unit 73402258, Chesterfield, MA 01012
/4
$669,000
- 4 Beds
- 3.5 Baths
- 1,908 Sq Ft
510 Main Rd, Chesterfield, MA 01012

Incredible opportunity to personalize a nearly new construction! This home is undergoing a complete transformation—only the original first-floor framing remains. A full second-floor addition and full interior rebuild are in progress. Now framed with rough plumbing and electrical underway, this is the ideal time for a buyer to select finishes and add personal style. The second floor will feature a

Daniel James Piasecki Coldwell Banker Community REALTORS®

510 Main Rd, Chesterfield, MA 01012

Massachusetts Hampshire County Chesterfield

Why Live in Chesterfield

Chesterfield, MA, is a rural hillside community in Hampshire County known for its natural beauty and seclusion. With abundant trees, farms, and brooks, Chesterfield offers a peaceful lifestyle, especially appreciated by its 1,200 residents, 40% of whom are aged 60 or over. The town is located about 45 minutes north of Springfield and 15 miles from Northampton, home to Smith College and a variety of retailers and restaurants. Outdoor enthusiasts can enjoy scenic hikes and cross-country skiing at Chesterfield Gorge Reservation, which features a dog-friendly trail along the Westfield River and connects to Gilbert A. Bliss State Forest. Russell Memorial Park provides local amenities such as a playground, skate park, baseball field, and tennis court. Winters can be cold and snowy, often extending into April, but winter recreation options like snowshoeing are available. Homes in Chesterfield are typically farmhouses and Cape Cod-style, many with large lots and waterfront views. Community engagement is fostered through events organized by the Council on Aging and the Chesterfield Library, which hosts the Family Harvest Festival and offers passes to local museums. Dining options are limited within Chesterfield, but the Chesterfield General Store and Café and Bread Euphoria Bakery & Café serve local and organic fare. For more extensive shopping, residents travel to Northampton, 15 miles away. Students attend schools in the Hampshire Regional School District, with New Hingham Regional Elementary and Hampshire Regional High School providing education from prekindergarten through twelfth grade.

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 $606,656.

Are home prices dropping in Chesterfield?

Yes, home prices in Chesterfield are down 16% in the last 12 months.

How many homes have sold over the last 12 months in Chesterfield, MA?

12 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, 01098 and 01027.

How much do you need to make to afford a house in Chesterfield?

The median home price in Chesterfield is $444,950. If you put a 20% down payment of $89,000 and had a 30-year fixed mortgage with an interest rate of 6.17%, your estimated principal and interest payment would be $2,170 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $93K a year to afford the median home price in Chesterfield.

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, Wahconah Regional High School and Hampshire 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 57 days on the market compared to the national average of 53 days. The median sale price for homes in Chesterfield, MA over the last 12 months is $402,450, up 13% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$402,450

Median Single Family Sale Price

$427,500

Average Price Per Sq Ft

$303

Number of Homes for Sale

Last 12 months Home Sales

Months of Supply

3.00

Median List Price

$444,950

Median Change From 1st List Price

Median Home Sale Price YoY Change

13%

How to Buy a Home How to Finance a Home How to Sell a Home

Homes in Nearby Neighborhoods

Homes in Nearby Cities

Homes in Nearby Counties

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage