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

$436,900

3 Beds ⋅ 2 Baths ⋅ 73572877 MLS

Perched on a hillside overlooking three acres of woodland and rolling meadow, this Colonial is minutes from the town center, Russell Memorial Park, and an easy jaunt to the best spot for a front row seat for the renowned annual 4th of July parade. The light-filled home offers flexible living space with two spacious bedrooms upstairs, a nicely sized room that would be a terrific first floor bedroom or office, two full bathrooms (one on each floor), first-floor laundry, and an open kitchen/living/area with Brazilian cherry floors. French doors lead from the living area to a sunroom/dining area with sliders that open to a stone patio. While there is no direct heat in the sunroom/dining area, it stays warm thanks to its proximity to the living room and passive solar heating. You'll love the gorgeous sunsets and amazing rainbows right in your own front yard. Owned solar panels, only three years old, are on the metal, maintenance-free roof. Electric car charger, newer central air, an efficient propane furnace, and a whole house water filtration system plus a reverse osmosis system for drinking water. There’s more: a spacious yard with room for gardening and exploring, a three-stall barn for storage, and a chicken coop. Watch for deer, foxes, rabbits, and an occasional bear roaming about the meadow. A wonderful place to call home, and an easy drive to Florence, Williamsburg, and Northampton.

92 South St, Chesterfield

Listing courtesy of Listing Agent: Rachel Simpson from Listing Office: 5 College REALTORS® Northampton.

$514,900

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.

$227,000

4 Beds ⋅ 1 Baths ⋅ 73526790 MLS

NEW PRICE! Freshly cleaned out and ready for your vision, this year-round Lake Damond waterfront home offers a clean slate for its next owner. Loved by the same family for generations, the property features 125 feet of direct lake frontage, a dock, three outbuildings, and access to the association’s private beach and playground. The main level includes an open living, dining, and kitchen area with a bank of windows overlooking the lake, an expansive deck, two bedrooms, a bath with shower, and a workshop/utility/storage room. Two additional bedrooms are upstairs. Improvements include a metal roof, private well, replacement windows, and a newer fuel oil tank. Septic is operational, but the seller assumes it will need replacement. Buyer is responsible for all septic testing, design, approvals, and costs. Floor plans available.

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: Alex Anthony R.E..

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