Chesterfield Homes under $750,000

Welcome to Chesterfield, Massachusetts—a hidden gem nestled in the heart of Hampshire County. Known for its stunning landscapes and close-knit community, Chesterfield offers a serene escape from the hustle and bustle of city life. With rolling hills, lush forests, and picturesque views, this charming town is perfect for nature lovers and those seeking a tranquil lifestyle.

Chesterfield boasts a rich history and a vibrant community spirit, where neighbors become friends and local events bring everyone together. The town is dotted with quaint shops, delightful eateries, and recreational opportunities that cater to all ages. Enjoy a leisurely hike on the scenic trails or spend a peaceful afternoon fishing in one of the nearby lakes. For families, Chesterfield's excellent school system and safe environment make it an ideal place to raise children.

When it comes to real estate, Chesterfield offers an array of homes priced under $750,000, making it accessible for first-time buyers, families, and retirees alike. From charming historic homes with character to modern builds that offer all the contemporary amenities, there’s something for everyone. Each property reflects the town’s unique charm and is often set against a backdrop of breathtaking natural beauty.

Whether you’re looking for a cozy cottage or a spacious family home, Chesterfield is ready to welcome you. Experience the warmth of this community and find your perfect home in a town that truly feels like a retreat. Discover the beauty and charm of Chesterfield today—your dream home awaits!

Newest Chesterfield Homes under $750,000

$425,000

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.

$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.

$675,000

5 Beds ⋅ 3 Baths ⋅ 73505281 MLS

Sellers willing to offer a $10,000 credit toward buying down interest rate, closing costs or buyer choice. Major 2025 improvements add peace of mind, including a new leach field and D-box, well pump, balcony railings off the primary suite, dishwasher, and central vac canister. Set on 2.73 private acres, this spacious Cape offers a flexible layout designed for a variety of living needs. The first floor features a primary suite with private bath, walk-in closet and balcony, granite kitchen, laundry, home office/flex room, and inviting gathering spaces. Upstairs are four additional bedrooms plus a separate bonus area with garage access, offering potential for guest quarters, in-law or multigenerational living, home office or B&B use (subject to local regulations). The walk-out lower level features radiant heat, partially finished space, cold storage and expansion potential. A peaceful setting with room to live, work and grow. 3 miles off the center of Chesterfield which features a cafe, town offices, library, post office, and park!

254 Bryant, Chesterfield

Listing courtesy of Listing Agent: Aimee Tompkins from Listing Office: Park Square Realty.

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