Chesterfield Real Estate

Welcome to Chesterfield, Massachusetts – a hidden gem nestled in the picturesque Hampshire County. This charming town, with its rich history and stunning natural beauty, offers a unique blend of rural tranquility and vibrant community life.

Chesterfield is characterized by its rolling hills, lush forests, and sparkling streams, making it a haven for outdoor enthusiasts. Residents and visitors alike can enjoy a plethora of recreational activities, from hiking and biking along scenic trails to fishing and kayaking in the pristine waters of the nearby rivers. The town is also home to several conservation areas, providing ample opportunities for birdwatching and nature walks.

The sense of community in Chesterfield is palpable, with friendly neighbors and local events that bring everyone together. The annual Chesterfield Fair is a highlight, showcasing local artisans, delicious food, and fun activities for all ages. The town's commitment to preserving its heritage is evident in its well-maintained historic buildings and the warm, welcoming atmosphere that permeates the area.

Chesterfield is also conveniently located near larger towns, allowing residents to enjoy the serenity of rural living while having easy access to modern amenities. With excellent schools, local markets, and small businesses, this quaint town offers a perfect balance of community spirit and convenience.

Whether you’re seeking a peaceful retreat or a place to call home, Chesterfield, MA, invites you to explore its charm and experience the beauty of life in this enchanting corner of Hampshire County. Come discover why so many have chosen to make Chesterfield their beloved home!

Newest Listings in Chesterfield

$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.

$550,000

2 Baths ⋅ 73570735 MLS

The Chesterfield General Store is an iconic hilltown business. The place to go for morning baked goods, coffee or breakfast sandwiches, for lunch or a snack, or for one of their top selling wood fired oven pizzas. Sold along with the meals and beverages are local arts and crafts merchandise and beer, wine and liquor. Catering, either in the store or at other locations, is a profitable part of the business. The building, which is in very good condition with many updates, and business are being sold together and offer a complete turn-key purchase opportunity. Come explore this opportunity to make your dream of owning your own impactful business come true!

432 Main Road, Chesterfield

Listing courtesy of Listing Agent: Michael Packard from Listing Office: Coldwell Banker Community REALTORS®.

$199,950

73561436 MLS

Ready to build without starting from scratch! This private 7.4-acre double lot on a quiet country road offers just over 400 feet of frontage and a beautiful homesite with extensive site work already completed. More than 2 acres have been professionally cleared and mulched while maintaining the surrounding woods for privacy. The driveway has been prepared, perc testing completed, and a 6-bedroom septic plan is ready to be filed. High-speed fiber internet is available. The property offers plenty of room for a spacious home, garage, gardens, outdoor living, and more, with marked hiking trails extending into the wooded acreage. Enjoy the privacy and quiet of the Hilltowns while remaining conveniently close to Williamsburg, Northampton, and the greater Pioneer Valley. Much of the costly and time-consuming work of turning raw land into a homesite has already been done. Bring your house plans and take advantage of a rare combination of acreage, privacy, build readiness, and easy access to the Pioneer Valley. See attached documents for details of completed work and request the drone video for a full view of the property.

Bissell Rd, Chesterfield

Listing courtesy of Listing Agent: Louis Poulin from Listing Office: eRealty Advisors, Inc..

$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.

$64,900

73521752 MLS

Peaceful waterfront getaway on beautiful Damon Pond! Rare opportunity to own a private recreational retreat with approx. 130’ of frontage on this scenic 82-acre pond known for its quiet coves, islands, inlets, and natural beauty. Camp, fish, kayak, canoe, swim, or simply unplug and relax by the water. Dock already in place for easy access. Property was previously used as a seasonal camping retreat with a tent/platform setup before being damaged by a fallen tree; some infrastructure remains onsite with potential for future camping platform, RV setup, or rustic getaway space. Broadband available via Whip City Fiber. Recent quote obtained for underground electric service and RV hookup (~$7,000). Lake Damon community maintains roads, beach area, and dam. Approx. association fee $750/year. Buyer to perform all due diligence regarding intended use, utilities, septic, permitting, zoning, and potential future building options.

Bray Rd, Chesterfield

Listing courtesy of Listing Agent: Melissa Stevens from Listing Office: Coldwell Banker Community REALTORS®.

$169,000

73512590 MLS

Rare water front lot on Damon Pond. Clearing needed to obtain a year round view of the pond. Lot is perc tested, surveyed with electric service being installed.. Join the association and have access to the recreation and beach area. NO power boating but kayaking, canoeing, fishing is available to all members. 25 minutes to Northampton. Year round recreational living in a quiet private setting. This is the place where you start with great amenities and build from there.

Pynchon Rd, Chesterfield

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

$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

73457166 MLS

Perched on the hill is a fully equip quality custom built MULTI USE BARN. Perfect for a Veterinarian clinic, horse or dog breeders, boarding, storing landscape equip, building equip, heavy equip. This property can do it all. The barn is entirely heated by radiant floor heat & includes 8 stalls w/auto waterers. Includes kit, office, W&D & bath. Also heated equip shed, workshop and drive through aisle for lg trucks, wash stalls & more. There are 8 paddocks w/waters, an exercise track, 3 lg pastures w/hydrants. A second barn offers another 12 stalls. The property starts at the gated driveway with meticulously kept and professionally landscaped grounds and a covered wraparound porch. Kit has quartz counters, GE Profile appliances & slider to large patio for entertaining. Gas FP in Livingroom, hardwood floors w/cherry inlay. Sweeping staircase to second floor w/5 bedrooms and grand primary en suite with private entrance. Whole house generator, central vac, 3 car garage. All on 55 acres.

31 North, Chesterfield

Listing courtesy of Listing Agent: Grace Golden from Listing Office: Alex Anthony R.E..

$321,600

73445753 MLS

The Kingsley Lot is 201.3 acres of forest land with 6,760 feet of frontage along the federally designated Wild and Scenic Westfield River in Chesterfield , MA. There is an island in the river that is a part of this property. The property is subject to a permanent Conservation Restriction held by the Mass Div Conservation and Recreation, formerly DEM, that prohibits development and has harvesting restrictions along the river and allows public access. The property has been managed by a professional forester for many years and supports a forest of red oak, red maple, birch, white pine and hemlock. A recent timber inventory in the documents section, identified a total value of $176,000 Property is classified under Chapter 61 for reduced property assessment. The CR is located at Book 5971 Page 110. Set along the Westfield River—the first in Massachusetts designated Wild and Scenic—these parcels offer a rare chance to own a piece of unspoiled New England beauty.

off Bryant St, Chesterfield

Listing courtesy of Listing Agent: Keith Ross from Listing Office: LandVest, Inc..

$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..

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.