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82 Willcutt Road, Chesterfield
$849,000
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..

309 Ireland St, Chesterfield
$530,000
3 Beds ⋅ 2 Baths ⋅ 73542070 MLS
Perched on two lush acres on Ireland Street & overlooking the hills of Worthington, this handsome farmhouse is the perfect marriage of tradition & modernity. 1st floor offers an open kitchen with large pantry & living room with access to the wraparound porch. Currently used as the primary bedroom, the addition at the rear of the home features vaulted ceilings, a wood burning fireplace & floor to ceiling windows with sunset views. Dining room & accessible full bath w/ laundry at front of house. 2nd floor has three sun-filled bedrooms and full bath w/ tub & shower. Attached barn with two garage bays, plentiful storage & workshop space. This energy-efficient home has brand new owned solar & has been converted to a central air heat pump system for heating & cooling. Interior access to basement with heated finished space & walk-out to the back yard, perfect for a den. Original foundation reinforced w/ concrete walls & floor. 200amp service & generator. Absolutely stunning yard & gardens.

309 Ireland St, Chesterfield

Listing courtesy of Listing Agent: Jocelyn Cleary from Listing Office: Canon Real Estate, Inc..

92 South St, Chesterfield
$440,000
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.

55 Cummington Rd, Chesterfield
$425,000
4 Beds ⋅ 2 Baths ⋅ 73512409 MLS
Nestled in the peaceful hills of Chesterfield, this inviting 4-bedroom, 2-bath home offers the perfect blend of privacy, comfort, and country charm. Surrounded by nature in a quiet setting, the property features a flexible floor plan with a first-floor bedroom, full bath, and family room—ideal for guests, multi-generational living, or convenient single-level living. A cozy pellet stove creates a warm and welcoming atmosphere during New England winters. Additional highlights include a spacious 2-car garage, storage shed, and raised garden beds ready for your seasonal planting. This well-maintained home provides a rare opportunity to enjoy serene Western Massachusetts living while remaining within reach of local amenities and outdoor recreation. Welcome to privacy and peaceful living!

55 Cummington Rd, Chesterfield

Listing courtesy of Listing Agent: Patriot Living Group from Listing Office: Lock and Key Realty Inc..

515 Main Rd, Chesterfield
$340,000
4 Beds ⋅ 1 Baths ⋅ 73578554 MLS
Beautiful pastoral location, a surprising amount of space and boundless potential for this Chesterfield cape home on 2.5 flat acres. First floor has a wraparound floor plan and bright entryway from garage with laundry and access to rear porch. Kitchen and adjacent dining room with bow window and built-in cabinet. Large living room surrounded by windows (hardwood under the carpets) with fireplace. Two first floor bedrooms at the rear of the home overlooking the back yard and full bathroom located on the hall with large linen closet. The bedrooms and dining room also have wood floors under the wall-to-wall carpeting. Second floor has two bedrooms and walk-in attic access for storage or could be finished for additional space. Full basement with workshop area, Buderus boiler and Roth double-wall oil tank. Single-car attached garage and additional carport with fixed generator. Detached workshop with electric, propane heater and garage door at rear. Title 5 failed and is buyer responsibility. First showings at the open house Saturday, September 19th from 1pm-3pm.

515 Main Rd, Chesterfield

Listing courtesy of Listing Agent: Jocelyn Cleary from Listing Office: Canon Real Estate, Inc..

54 Bray Rd, Chesterfield
$193,000
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.

316 Main Road, Chesterfield
$169,700
4 Beds ⋅ 1 Baths ⋅ 73480565 MLS
Situated gracefully on a level, partially wooded parcel of 3 acres creating ample room for family activities, this single family Cape presents an inviting home atmosphere. And after some customizing and renovation, this home is poised for occupancy. The thoughtfully proportioned living area, encompassing 1947 square feet, provides optional use areas for comfortable daily routines and personal pursuits. Within the residence, two private sleeping quarters offer tranquil sanctuaries for rest and rejuvenation on the first floor. A full bathroom with oversized walk in shower thoughtfully complements the two bedrooms at one wing of the house ensuring essential convenience and functional elegance. There is space on the second floor used for an additional two bedrooms. A fireplaced LR with picture window, dining area with built in cabinets, galley kitchen, breezeway/office with separate entrance and attached 1-car garage adds value to this opportunity. Property to be sold in as is.condition.

316 Main Road, Chesterfield

Listing courtesy of Listing Agent: Jarod Martin from Listing Office: Greenfield Group Real Estate.

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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