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Chesterfield, MA Houses for Sale

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  • 345 Ireland St, West Chesterfield, MA 01084
    345 Ireland St, West Chesterfield, MA 01084
    345 Ireland St, West Chesterfield, MA 01084
    /41

    $825,000

    • 3 Beds
    • 2.5 Baths
    • 1,907 Sq Ft

    345 Ireland St, West Chesterfield, MA 01084

    This is the place where dreams come true! A large 3 bed/2.5 bath modern home, classic 2 stall barn with hayloft and insulated, heated 30x50 garage/barn w/ 16' ceilings on nearly 70 acres. Just 30 mins from Northampton this idyllic setting features bucolic views, open green fields and woods with stone walls and winding trails that lead to Jackson’s Brook. A contemporary home with warm traditional

    Agent Photo

    Lisa Carroll

    Delap Real Estate LLC

    (413) 366-3784

    345 Ireland St, West Chesterfield, MA 01084
  • 510 Main Rd, Chesterfield, MA 01012
    510 Main Rd, Chesterfield, MA 01012
    510 Main Rd, 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
  • 31 Farmhouse Rd, Chesterfield, MA 01012
    31 Farmhouse Rd, Chesterfield, MA 01012
    31 Farmhouse Rd, Chesterfield, MA 01012
    /37

    $439,000

    • 2 Beds
    • 1 Bath
    • 1,024 Sq Ft

    31 Farmhouse Rd, Chesterfield, MA 01012

    It's HOT -buy a lake house! Escape to serenity with this charming lakefront cottage, a perfect blend of comfort and natural beauty. Built in 1989, this delightful single-family home features 2 cozy bedrooms and 1 full bath, all nestled in a tranquil wooded setting. The open-concept layout invites warmth and light, with expansive windows that frame stunning views of the surrounding landscape. The

    Shelly Hardy Brick & Mortar Northhampton

    31 Farmhouse Rd, Chesterfield, MA 01012
  • 330 East St, Williamsburg, MA 01096
    330 East St, Williamsburg, MA 01096
    330 East St, Williamsburg, MA 01096
    /37

    $875,000

    • 3 Beds
    • 2 Baths
    • 2,922 Sq Ft

    330 East St, Williamsburg, MA 01096

    Welcome to your sanctuary of privacy, natural beauty and well-being! This exquisitely designed home, set on 70 acres, is built with the highest standards for a healthy lifestyle. Enjoy the unparalleled comfort of geothermal radiant heating, providing consistent warmth throughout the home. Large south facing windows, designed for passive solar, bathe the home in natural light, creating a bright,

    Linda Webster Coldwell Banker Community REALTORS®

    330 East St, Williamsburg, MA 01096
  • 7 Sundown Dr, Williamsburg, MA 01096
    7 Sundown Dr, Williamsburg, MA 01096
    7 Sundown Dr, Williamsburg, MA 01096
    /42

    $669,000

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

    7 Sundown Dr, Williamsburg, MA 01096

    Your woodland retreat awaits, perched on 9 acres just 10 minutes to Williamsburg Ctr. & 25 minutes to downtown Northampton. The original structure was built in 1983 using timber from the property & features an open floor plan w/ exposed beams, tons of southerly light, a large eat in kitchen, a sunroom w/ built-in benches, a living room w/ wood stove insert, a screened in porch leading to a deck,

    Kimberly Raczka 5 College REALTORS® Northampton

    7 Sundown Dr, Williamsburg, MA 01096
Massachusetts Chesterfield

Houses for Sale in Chesterfield, MA

Why Live in Chesterfield

Chesterfield, a rural hillside community in Hampshire County, is known for its natural beauty and seclusion, with abundant trees, farms, and brooks. The area is particularly picturesque in autumn, with vibrant foliage that can be enjoyed while hiking, driving, or relaxing at home. Chesterfield is about 45 minutes from Springfield and 15 miles from Northampton, which offers a variety of retailers, restaurants, and Smith College. The town's 1,200 residents, many of whom are aged 60 or over, enjoy a quiet lifestyle amidst scenic surroundings. Outdoor recreation is plentiful, with Chesterfield Gorge Reservation offering dog-friendly hiking trails, fly fishing, and winter activities like snowshoeing and cross-country skiing. Gilbert A. Bliss State Forest features a 5-mile hiking loop, and Russell Memorial Park provides a playground, skate park, and sports facilities. Homes in Chesterfield are typically farmhouses and Cape Cod-style, often surrounded by trees and sometimes featuring waterfront views. Larger properties may include barns or greenhouses. Community events are organized by the Council on Aging and the Chesterfield Library, which hosts festivals and offers museum passes. Dining options are limited within Chesterfield, but the Chesterfield General Store and Café and Bread Euphoria Bakery & Café on Route 9 are popular local spots. For more extensive shopping, residents travel to Northampton. The Hampshire Regional School District serves local students, with New Hingham Regional Elementary and Hampshire Regional High School offering various clubs and activities. Residents rely on personal vehicles for transportation, with Route 143 and Route 9 providing access to nearby areas. Emergency care is available at Holyoke Medical Center, 20 miles away.
Learn more about living in Chesterfield

Home Trends in Chesterfield, MA

On average, homes in Chesterfield, MA sell after 5 days on the market compared to the national average of 50 days. The median sale price for homes in Chesterfield, MA over the last 12 months is $355,000, down 18% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$355,000
Median Single Family Sale Price
$415,000
Average Price Per Sq Ft
$266
Number of Homes for Sale
1
Last 12 months Home Sales
3
Months of Supply
4.00
Median List Price
$392,500
Median Change From 1st List Price
-6%
Median Home Sale Price YoY Change
-18%
How to Buy a Home How to Finance a Home How to Sell a Home

In Chesterfield, there are currently 5 houses for sale, offering an array of options for potential buyers. With houses priced between $439,000 to $875,000, there's a range to accomodate every budget. As of June, 2025 the median home price in Chesterfield is $392,500, while the average sale price is $380,000, offering insights into the local housing market. On average, houses spend 5 days listed before being sold. Whether you're searching for a single-family residence, exploring single-family detached houses for sale, or considering new construction houses for sale, there are options to cater to different lifestyles. Explore the listings and houses for sale in Chesterfield, MA and find the perfect place to call home.

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