Sheffield, MA Homes for Sale

Welcome to Serenity Hill.This 1994 Cape style home captures the timeless charm of the Berkshires from the moment you arrive. At the entrance, stately stone pillars and a classic stone wall offer a graceful welcome, setting the tone for the calm, natural beauty that defines life in the Berkshires. Located on the border of Great Barrington, this Sheffield home is on a peaceful, quiet country road.

William Morrow WILLIAM PITT SOTHEBY'S - GT BARRINGTON

Custom modern home with open plan living area, high ceilings and oversized windows everywhere bringing in tremendous natural light. One level living with large gorgeous marble kitchen, great working island and wall pantry. Guest wing off entry with two bedrooms and a hall bath. Entry hall has a powder room, hooks for coats and closet. The primary suite, on the south side, has french doors to

Jen Harvey COMPASS MASSACHUSETTS , LLC GB

Stunning contemporary sanctuary in Ashley Falls offering perfect blend of modern design & natural surroundings. 3BR/2.5BA residence bathed in natural light. The first floor features a comfortable den, eat-in kitchen and gracious living room with marble wood burning fireplace. A thoughtfully designed floor plan flows seamlessly to outdoor spaces including large deck for al fresco dining &

Karen Climo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

Beautifully Built New Construction in SheffieldMove-in ready and thoughtfully crafted by a local custom builder, this 3-bedroom, 2-bath home sits on 1.64 private acres. The open-concept living, dining, and kitchen area flows seamlessly to a lovely backyard patio--perfect for indoor-outdoor living. Nearby hiking, biking, and skiing offer endless recreation, or simply relax and enjoy the peaceful

Claire Pollart LANCE VERMEULEN RE, INC

Nestled at the end of a quiet country cul-de-sac, this newly built 5-bedroom, 4.5-bath home embodies refined country living. A dramatic primary suite offers dual walk-in closets and a spa-inspired bath with soaking tub, while a first-floor ensuite bedroom enhances comfort and flexibility. The gas fireplace living room and chef's kitchen create a seamless flow for entertaining, extending to a

Vashti Poor LANCE VERMEULEN RE, INC

Classic 3-Bedroom Cape with Pool - Perfectly positioned between NW Connecticut and Sheffield, MA in the Berkshires. Sheffield is the oldest Town in Berkshire County - the township was purchased in 1724 from Chief Konkapot and other Stockbridge Native Americans. This bright, lovely 3-Bedroom Cape features a beautiful, heated pool, a Bedroom and Full Bath on the Main Floor, 2 Bedrooms and another

Juliet Moore ELYSE HARNEY REAL ESTATE

This gracious vintage home has been thoughtfully renovated and lovingly maintained by the current owners for over 20 years. High ceilings, wonderful light, spacious rooms, a ''walk to everything'' in town location, and residential/commercial zoning provide comfort and unlimited possibilities. A 1,000 sq. ft. outbuilding with water & electric service adds more potential. Beautiful period

David Taylor ELYSE HARNEY REAL ESTATE

A total 41 acres includes a 2nd building lot of 26 acres allowing one to build ones own home with mountain views. A 36x52 work shop. One full time residence and a separate summer studio. Some land does go into New Marlborough. Surrounded by conservation land. Passive solar views facing South and West. Property has been a sculpture park for many years. Trails throughout. Views to Connecticut.

Suzann Ward HOUSATONIC REAL ESTATE

Modernist delight in a Berkshire pastoral setting. A refined retreat where every detail reflects quality and style. Designed by acclaimed architect Deby Reiser, this light-filled three-bedroom, three-bath home blends the sophistication of urban design with the calm of Berkshire countryside living. Tucked away on a quiet country road beside Moon In the Pond Farm an eco-friendly farm with peaceful

Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

Open House 10-11-25, 11:00-1:00. Inside pictures to follow soon. Experience the perfect blend of modern comfort and historical charm in this beautifully maintained home. Featuring 4 spacious bedrooms and 2 baths, this home offers over 1,500 sq. ft. of living space. Enjoy the character of the 1850s with updates, including new mechanicals. Freshly painted inside and out, this home is truly move-in

Suzann Ward HOUSATONIC REAL ESTATE

Wonderful location, 3 bedroom, 3 bath split level. Minutes to the downtowns of Sheffield and Great Barrington. Primary with en suite bath, finished lower level with family room, artists studio plus a two car garage.

Michael Harrigan BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

A Berkshire dream home! Nestled in a quiet private setting to enjoy the outdoors. This 3 bedroom 3 full bath home is empty and ready to go. Great lighting nice open kitchen dining/living area. Additional room can be used as a den or 1st floor bedroom. Wood stove insert for chilly fall nights while enjoying your 3 seasoned screened porch. Oversized 2 car garage. Full basement could be completed as

Suzann Ward HOUSATONIC REAL ESTATE

Located on a pastoral country road in Sheffield, this thoughtfully updated early 1900s farmhouse with carriage house sits on 1 open acre with sweeping views to the west of conservation land. The home blends original character withmodern touches--vaulted ceilings, exposed beams, hard wood floors, and high-end finishes throughout. In the main house a sunlit kitchen anchors the home featuring custom

Lauren Molk ELYSE HARNEY REAL ESTATE

SPECTACULAR ONE OF A KIND BERKSHIRE PROPERTY! This compound includes an elegant and updated 4 bedroom 1759 Colonial home and fabulous RED BARN with 2 separate guest spaces. Mill pond for fishing, heated pool, patios and screen porch, 66 protected SUBDIVIDABLE ACRES...with views of Mount Washington. The perfect place to entertain friends and family. An incredible opportunity for additional

Patrice Melluzzo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

Historic village living at its finest. This expansive Turn-of-the-Century Sheffield home is rich with original detail, from its warm wood floors to a magnificent fieldstone fireplace. The property boasts a large, private yard, offering ample space for gardening, recreation, or outdoor entertainment. A substantial barn on the property provides excellent potential for a workshop, studio, or extra

Tony Segalla LANCE VERMEULEN RE, INC

An exceptional opportunity awaits on 11 private acres in Sheffield. This unique property, currently utilized as a functional therapy facility, offers a massive footprint and a flexible canvas for your next venture. The centerpiece is an 8,000+ sq. ft. building comprised of over 10 offices, multiple conference rooms, common areas, and three residential apartments, creating an ideal setup for a

Tony Segalla LANCE VERMEULEN RE, INC

Old Historic Village downtown location! The centrally located Post Office building constructed in 1860, presents a unique opportunity for both residential and commercial use. Its strategic location ensures consistent foot traffic, making it an invaluable cornerstone of village life. With no mail delivery service in Ashley Falls, the Post Office attracts local residents daily. This building is

Tony Segalla LANCE VERMEULEN RE, INC

Welcome the historic Foxdale and the opportunity to own a piece of history that begins before the declaration of independence. This property originally was built in the 1750s. If a house with character is what you're looking for, look no further! In the heart of the village of Sheffield, you will find this property unlike any other. After its complete restoration by its visionary new owner this

Cortney Dupont COHEN & WHITE ASSOCIATES

The ULTIMATE LIVE-WORK-PLAY RETREATStep onto a property as striking as the Berkshires themselves--where innovative design meets natural splendor, creating an extraordinary canvas for your ideal lifestyle. The 13,738 sq ft retreat fondly known as ''The Factory'' spans 5+ acres with views of rolling hills & protected fields. 10,000 sq ft of versatile commercial and creative space below and flanked

Chapin Fish WILLIAM PITT SOTHEBY'S - GT BARRINGTON

Experience breathtaking panoramic vistas over protected land from every angle in this renovated Classic American Farmhouse. Nestled on two parcels, this residence boasts a pool, a detached garage, and gracious proportions throughout. Relax in the majestic long-range mountain vistas. The house is perfectly positioned to experience both sunrise and sunset views.Step inside to discover an

Elyse Morris ELYSE HARNEY REAL ESTATE

Mid-1960s ranch on a quiet street with nearly 1/2 acre! A perfect family home to settle down in Southern Berkshire County. Semi-finished basement is a huge bonus, plus garage and additional detached barn/workshop. Sunny, spacious and ripe with potential. Some thoughtful updates will be needed -- or move in today and make it yours!

John Segalla HOUSATONIC REAL ESTATE

Come this charming 1820 colonial located in Downtown Sheffield! This unique property features 6 bedrooms and 5 and half bathrooms. Lovely hardwood showcasing wide plank and parquet style floors encompass 3,683 square feet of living space. Plenty of off street parking due to the oversized driveway and 2 car attached garage with loft space. Full, unfinished basement can provide additional storage

Nicholas Decaro Property Works New England

Custom Built Craftsman Contemporary Home nestled in a beautifully landscaped property with an orchard, gardens and path to a seasonal brook. Inside this well appointed home you will find large rooms Vaulted ceilings, whimsical lighting, Fireplaces, Indoor pool, hot tub and sauna, radiant floor & forced air throughout. Two primary suites on main floor and 2/3 more bedrooms in the lower walkout

Mark Rosengren LANCE VERMEULEN RE, INC