Chesterfield Real Estate

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

316 Main Road, Chesterfield
$425,000
4 Beds ⋅ 1 Baths ⋅ 73595201 MLS
This Chesterfield, Massachusetts single-family Cape Cod residence has just completed many updates including new windows, new roof, septic system and a complete refurbish of the interior. Constructed in 1960 and encompassing 1,947 square feet of living space, this home has much to offer new owners. This attractive property offers a balanced integration of timeless architecture and functional modern updates, set upon a generous 3 acre wooded lot. Entering from the side near the garage a spacious lighted area with a picture window framing the natural beauty of the rear yard presents itself and may serve as a den, private office, exercise or Pilate's space. Moving into the adjoining main home, an open dining area and fireplace living room welcomes all to gather. The galley kitchen serves as the heart of the home while utilizing efficiently the space allotted and featuring refined stone counters paired with a suite of high-quality stainless steel appliances. This space is designed for both culinary efficiency and social interaction. The living room off the main entry foyer serves as a welcoming gathering point, anchored by an inviting fireplace that provides a focal point for the residence. The bathroom is designed for convenience and ease, appointed with a double sink and a spacious walk-in shower. This residence further accommodates practical living needs with four bedrooms, an attached garage, and a dedicated workshop space. These additional areas provide ample room for professional projects, hobbies, or storage, ensuring the home remains as functional as it is comfortable. We invite you to schedule a private viewing to experience the character and quality of this Chesterfield property firsthand. We have placed some furniture in a few rooms to demonstrate the options for size and use.

316 Main Road, Chesterfield

Listing courtesy of Listing Agent: Jarod Martin from Listing Office: Greenfield Group Real Estate.
31 North Rd, Chesterfield
$1,850,000
5 Beds ⋅ 3 Baths ⋅ 73589598 MLS
The equestrian elegance of this hilltop property begins the moment you arrive, a gated driveway winding through professionally landscaped grounds and leading to an expansive 55-acre sanctuary designed for both refined country living and serious equestrian pursuits.The home welcomes you with a grand entryway and a covered porch. Inside, hardwood floors w/ cherry inlay, a sweeping staircase, and a gas fireplace create an atmosphere of timeless sophistication. The kitchen features quartz countertops and high-end GE Profile appliances, access to a large patio ideal for entertaining. An expansive primary en suite offers a private entrance and a peaceful retreat, while four additional large bedrooms provide generous accommodations for family and guests. Main-floor laundry, central vacuum, 5 heat zones, a whole-house generator, security system, and three electrical meters add efficiency and peace of mind.Outside, the property continues to impress with extensive outdoor lighting, an expansive lawn, gated driveway, large patio, automatic propane grill, and meticulously maintained landscaping. PVC three-rail fencing creates a polished aesthetic throughout the grounds.At the heart of the estate is a fully equipped, custom-built multi-use barn thoughtfully designed for breeders, veterinarians, trainers, and discerning horse owners. The main barn features eight 14' x 14' stalls w/ automatic waterers, radiant floor heating, heated wash stalls, a heated tack room, heated tacking area, kitchenette with laundry, office, bathroom, ceiling fans throughout, and a rubber “cobblestone” aisle. A remarkable 44' x 105' hay loft provides substantial storage.Efficiency is built into the operation with a heated drive-through aisle for easy loading, heated equipment shed and workshop and large parking area. The barn has its own private well and septic system. A second barn, 12 additional stalls, providing a total of 20 stalls.The outdoor equestrian amenities are equally impressive: eight paddocks with automatic waterers and hay huts, three large pastures, and an exercise track. Every detail has been thoughtfully considered to make professional operations exceptionally convenient.This is far more than a beautiful country property. It is a sophisticated equestrian estate where luxury and professional-level horse facilities come together on approximately 55 acres—an extraordinary opportunity for the serious equestrian seeking a turnkey operation and an exceptional place to call home.

31 North Rd, Chesterfield

Listing courtesy of Listing Agent: Grace Golden from Listing Office: CR Premier Properties.
50 Bray Road, Chesterfield
$405,000
2 Beds ⋅ 1 Baths ⋅ 73586487 MLS
Set on 1.5 acres, directly on the shores of Damon Pond, this peaceful, quiet retreat offers a private dock, glorious water views & exceptional privacy! With a new picture window facing the pond, the beauty of the setting can be enjoyed year-round from this sweet, ranch-style home. Thoughtfully improved, this home has undergone an impressive list of updates! Current owner has added a spacious attached garage and tiled mudroom! New metal roof, new deck, new front porch & a major driveway upgrade featuring new circular driveway for easy entry & exiting. This home has been fully deleaded, electrical updated w/new panel, additional insulation & thermal barrier. Washer & dryer have been added plus mini-split for AC/supplemental heat, attic provides additonal storage. All windows on main level have been replaced, portable generator added for peace of mind, high-speed internet! Whether you’re looking for a year-round home or quiet escape, this property offers the chance to slow down, enjoy the warmth of the cozy propane stove in winter, the ease of one-level living and the tranquility of lakeside living. Kayak off the dock to the private beach for a swim, enjoy fishing or simply take in the changing seasons on the water! Conveniently located approx. 30 min to Northampton & 30 min to the Berkshires.

50 Bray Road, Chesterfield

Listing courtesy of Listing Agent: Lisa Palumbo from Listing Office: Delap Real Estate LLC.
432 Main Road, Chesterfield
$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®.
Bissell Rd, Chesterfield
$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..
3 Stage Rd, Chesterfield
$469,000
3 Beds ⋅ 2 Baths ⋅ 73549025 MLS
Watching the Deer and Flocks of Turkeys eating apples in the back yard while the birds and bees wander through the flower and fruit gardens. 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 bedroom 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 skylights 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 walkways. Included is a 2 story barn that serves as both a garage work shop area and storage. Over 30 acres with access from the next road over.

3 Stage Rd, Chesterfield

Listing courtesy of Listing Agent: James A. Molyneux from Listing Office: Molyneux Realty.
Pynchon Rd, Chesterfield
$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.
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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.

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