Chesterfield Homes with Cape Style

Welcome to Chesterfield, Massachusetts, a hidden gem nestled in the heart of Hampshire County. This charming town, with its picturesque landscapes and friendly community, offers a serene escape from the hustle and bustle of city life. Chesterfield is known for its rolling hills, lush forests, and stunning views, making it an ideal location for nature lovers and outdoor enthusiasts. With a rich history dating back to the 18th century, the town boasts a quaint New England charm that captivates both residents and visitors alike.

One of the most appealing features of Chesterfield is its collection of beautiful Cape-style homes. These classic residences, characterized by their steep roofs and symmetrical facades, exude warmth and character. The Cape Cod style is not just a house; it’s a lifestyle that emphasizes comfort and practicality, perfect for families or those seeking a peaceful retreat. Many of these homes are set on spacious lots, surrounded by the natural beauty that defines Chesterfield, providing ample space for gardens, outdoor gatherings, and play.

Living in Chesterfield means embracing a slower pace of life while still enjoying modern conveniences. The community is close-knit, with local shops, farmers' markets, and recreational activities that foster a sense of belonging. Whether you’re hiking the nearby trails, exploring local art galleries, or simply enjoying a quiet evening on your porch, Chesterfield offers a unique blend of tranquility and charm. Discover your dream Cape-style home in this idyllic town, where every day feels like a retreat.

Newest Chesterfield Homes with Cape Style

$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..

$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.

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