5

Chesterfield, MA Houses for Sale

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  • /41

    $810,000

    • 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
  • /12

    $269,000

    • 2 Beds
    • 1 Bath
    • 871 Sq Ft

    46 Bray Rd, Chesterfield, MA 01012

    Year-Round Waterfront living in this adorable 2-bedroom, 1 bath cottage tucked along the shores of Damon Pond in Chesterfield, MA. Featuring an open floor plan that maximizes space and light. Remodeled kitchen and bath. New Metal roof (2021). Storage shed. Nature lovers will feel right at home with frequent sightings of kingfishers, blue herons and even bald eagles. Spend your days kayaking,

    Linda Webster Coldwell Banker Community REALTORS®

    46 Bray Rd, Chesterfield, MA 01012
  • /42

    $775,000

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

    330 East St, Williamsburg, MA 01096

    Nestled on over 70 acres of natural beauty just over the Westhampton border, this nearly 3,000 sq ft custom-built home offers privacy, peace, and thoughtful design throughout. Large southern-facing windows capture mountain views, while the open floor plan flows seamlessly from the kitchen to living and dining areas. Radiant floor heat, tile floors, and a sunroom enhance comfort year-round.

    Jill Vincent-Lapan Canon Real Estate, Inc.

    330 East St, Williamsburg, MA 01096
  • /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
  • /37

    $399,000

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

    31 Farmhouse Rd, Chesterfield, MA 01012

    Whether it's year-round or a summer retreat, you've got swimming and ice skating covered.Escape to 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

    Shelly Hardy Brick & Mortar Northhampton

    31 Farmhouse Rd, Chesterfield, MA 01012

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.

Home Trends in Chesterfield, MA

Housing Trends

Median Sale Price
$440,000
Median Single Family Sale Price
$440,000
Average Price Per Sq Ft
$296
Number of Homes for Sale
0
Last 12 months Home Sales
3
Months of Supply
0.00
Median List Price
$465,000
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
-7%
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