Chesterfield Homes with Single Family Residence Subtype

Welcome to Chesterfield, Massachusetts, a hidden gem nestled in the picturesque Hampshire County. Known for its stunning natural landscapes, Chesterfield offers a serene retreat from the hustle and bustle of city life, making it an ideal location for families and individuals seeking tranquility and community. With its charming rural atmosphere, this quaint town is characterized by rolling hills, lush forests, and scenic views that create a perfect backdrop for outdoor enthusiasts and nature lovers alike.

Chesterfield is not just about breathtaking scenery; it boasts a rich history and a close-knit community that welcomes newcomers with open arms. Residents enjoy a slower pace of life, with local events and farmers’ markets that foster connections among neighbors. The town’s commitment to preserving its natural beauty and fostering a vibrant community spirit makes it an attractive place to call home.

When it comes to housing, Chesterfield features a delightful array of single-family residences that cater to diverse lifestyles and preferences. These homes often showcase charming architectural styles, spacious yards, and modern amenities, providing comfortable living spaces that are perfect for families or those looking to settle down. Whether you seek a cozy cottage or a larger family home, the real estate market in Chesterfield offers a variety of options to fit your needs.

In Chesterfield, you’ll find not just a house, but a place to build memories and create a life surrounded by nature and community. Embrace the opportunity to make this enchanting town your new home!

Newest Chesterfield Homes with Single Family Residence Subtype

$529,000

3 Beds ⋅ 2 Baths ⋅ 73549025 MLS

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 Kitchen, full bath, half bath, laundry and office. The main side entry from the side porch serves as a foyer to the main house and opens into the amazing Family room with exposed beam ceiling filled with windows overlooking the stone patio and gardens. Second floor offers a bed room with skylight and an additional guest/office room. The great outdoors includes a lovely stone patio surrounded by flowering plantings that open to a yard of beautiful flowered walk ways. Included is a 2 story barn that serves as both a garage work shop area and storage. All this on over 30 acres with brook.

3 Stage Rd, Chesterfield

Listing courtesy of Listing Agent: James A. Molyneux from Listing Office: Molyneux Realty.

$898,000

3 Beds ⋅ 3 Baths ⋅ 73532241 MLS

Nestled into 3.2 acres of serene woodland, this breathtaking custom contemporary Cape — crafted in 2018 by Sovereign Builders — is nothing short of a dream realized. Soaring ceilings and large windows pour golden light across rich hardwood floors, while dreamy western sunsets paint the sky behind multiple mountain vistas. Every room frames woodland views, and resident hummingbirds set a pace that is unhurried and deeply restorative. The open floor plan flows with easy elegance, anchored by a stunning kitchen with stainless steel appliances and shaker cabinetry. The first-floor primary suite offers a private sanctuary, while a rustic cabin tucked on the property beckons as a writer's retreat — with a fire pit and patio for starlit gatherings. Yet for all its stillness, the world is never far. Northampton is 20 minutes away, Tanglewood a beautiful ride, and the Chesterfield Gorge offers world-class fly fishing and hiking just down the road. Private, purposeful, and quietly extraordinary

82 Willcutt Road, Chesterfield

Listing courtesy of Listing Agent: Jeanne Troxell Munson from Listing Office: The Murphys REALTORS®, Inc..

$250,000

4 Beds ⋅ 1 Baths ⋅ 73526790 MLS

Loved by the same family for generations, this year-round Lake Damond waterfront property is ready for its next chapter. Offering 125 feet of lake frontage, this 4 bedroom, one bath home is tucked into a wooded setting for privacy while still providing plenty of open, sunny space to enjoy the water. The main level features an open living, dining, kitchen area w/ a bank of windows overlooking the lake, access to the expansive deck, 2 first floor bedrooms, a 1st floor bath w/ shower, and workshop/utility/storage room. Upstairs are 2 additional bedrooms. Outdoor features include swimming, non-motorized boating, dock, 3 outbuildings, and access to the association’s private beach and play ground. Improvements include a metal roof, Well, replacement windows, and fuel oil tank. Property is being sold furnished & strictly AS IS, WHERE IS. Septic is operational but its assumed the system will need replacement. Cash buyer/rehab loan likely due to septic.

54 Bray Rd, Chesterfield

Listing courtesy of Listing Agent: Shelly Hardy from Listing Office: Brick & Mortar Northampton.

$685,000

5 Beds ⋅ 3 Baths ⋅ 73505281 MLS

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 entrance create exciting opportunities for a private guest suite, in-law accommodations, multigenerational living, home business, or potential bed-and-breakfast venture (subject to local regulations). The walk-out lower level offers radiant heated floors, partially finished space, and room for future expansion. Peaceful surroundings, flexible spaces, and a location that feels miles away while remaining close to local amenities make this property truly one of a kind.

254 Bryant, Chesterfield

Listing courtesy of Listing Agent: Aimee Tompkins from Listing Office: Park Square Realty.

Start Your Search

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.