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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
  • /41

    $1,950,000

    • 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 &

    Sharron Cochran Equine Homes Real Estate, LLC

    31 North 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
  • /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
$425,000
Median Single Family Sale Price
$435,000
Average Price Per Sq Ft
$298
Number of Homes for Sale
3
Last 12 months Home Sales
11
Months of Supply
3.30
Median List Price
$450,000
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
20%
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