Chesterfield Homes for Sale

Welcome to Chesterfield, Massachusetts, a hidden gem nestled in the picturesque Hampshire County. Known for its serene landscapes and charming rural atmosphere, Chesterfield offers a unique blend of natural beauty and small-town charm. With rolling hills, lush forests, and tranquil streams, this quaint town is perfect for those seeking a peaceful retreat from the hustle and bustle of city life.

Chesterfield is a tight-knit community where neighbors become friends, and local events foster a sense of belonging. Residents enjoy a slower pace of life, with plenty of opportunities for outdoor activities, including hiking, biking, and exploring the nearby state parks. The town’s rich history is reflected in its well-preserved architecture and community landmarks, making it a delightful place to call home.

For those looking to plant roots in this idyllic town, there are a variety of homes for sale that cater to diverse lifestyles and preferences. From charming historic homes that exude character to modern constructions that offer contemporary amenities, Chesterfield has something for everyone. Whether you're a first-time homebuyer, a growing family, or seeking a peaceful retirement retreat, you’ll find properties that fit your needs perfectly.

With its stunning natural surroundings, welcoming atmosphere, and an array of homes for sale, Chesterfield is more than just a place to live; it's a community where you can thrive. Explore the possibilities and discover your dream home in Chesterfield today!

Newest Chesterfield Homes for Sale

$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.

$1,850,000

5 Beds ⋅ 3 Baths ⋅ 73420042 MLS

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 & more. The grounds include 8 paddocks with waterers , an exercise track, 3 lg pastures w/ hydrants. A second barn offers 12 addl stalls. The Meticulously kept grounds is professionally landscaped and a covered wraparound porch to greets guests. Kitchen has quartz counters, GE Profile appliances & a slider to large patio perfect for entertaining. Gas Fireplace in Livingroom, hardwood floors w/cherry inlay. Sweeping staircase to second floor w/4 bedrooms and a grand primary en suite with a private entrance. Whole house generator, central vac & 3 car garage. SEE VIDEO & ATTACHMENT FOR FULL DETAIL

31 North Road, Chesterfield

Listing courtesy of Listing Agent: Grace Golden from Listing Office: Equine Homes Real Estate, LLC.

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