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

$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.

$79,900

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: Equine Homes Real Estate, LLC.

$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: Equine Homes Real Estate, LLC.

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