Sheffield, MA Homes for Sale with Acreage

The Hatfield House : A rare 1793 Sheffield antique offering a unique renovated live/work opportunity, move-in ready; the main residence blends historic character with modern systems; including a new sealed basement. A separate one-bedroom apartment with its own entrance provides income or guest flexibility. Set on 1.5 acres with protected wetland views, commercial/residential zoning allows for

Judi Panzano HOUSATONIC REAL ESTATE

Bordering protected land and moments from the Appalachian Trail, this light-filled contemporary offers privacy, comfort, and an easy connection to the natural beauty of the Berkshires. Set on one acre in a peaceful Sheffield location, the home features vaulted ceilings, open gathering spaces, and a flexible layout designed for both everyday living and entertaining. The spacious kitchen flows into

Lisa Crawford BIRCH PROPERTIES

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

Modernist retreat in a pastoral Berkshire setting-an artful sanctuary where design, landscape, and light exist in quiet harmony. Designed by acclaimed architect Deby Reiser, this light-filled two-bedroom, three-bath home blends refined urban modernism with the stillness of the countryside. Set along a quiet dirt road beside Moon In The Pond Farm, (an eco-conscious farm) a landscape of grazing

Elyse Morris Elyse Harney Real Estate

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 WILLIAM RAVEIS - BERKSHIRE

Dreamy river Colonial: tucked away on 4 beautiful acres, 1361 feet of river frontage, offering privacy and a quiet sanctuary for wildlife viewing. Main floor features an updated classic chef's kitchen that flows into a spacious Great Room w/ wood-burning fireplace, dining area, 1/2 bath, and direct access to the sun deck with sparkling river and dramatic sunset views. A breezeway connecting the

Claudia Laslie WILLIAM RAVEIS - BERKSHIRE

This historic farmhouse, originally built in the 1790s, underwent a complete renovation in 2012, including a new foundation, septic system, roof, updated plumbing and electrical, 5-zone heating, central air, and other modern systems. In 2022, a new well and a boiler for radiant heat were also added. Step inside to find timeless Colonial charm--exposed beams, three original fireplaces, and

Timothy Lovett COMPASS MASSACHUSETTS , LLC GB

Nestled in Sheffield Village on 8+ acres, this charming New England farmhouse blends rustic character with modern comfort. Featuring 3 bedrooms, 2 baths, wood floors, beams, Great Room with a gas stove offers a warm inviting space Enjoy a country kitchen with a pantry. Screened in porch with outdoor patio, gardens, and two sheds for storage or hobbies. Perfect as a private sanctuary or Airbnb,

Suzann Ward HOUSATONIC REAL ESTATE

Step into a canvas of timeless character in this Historic Colonial, originally built and occupied by Nathaniel Austin,a surveyor who was instrumental in mapping and settling Berkshire County, situated in the town of Sheffield. This 5-bedroom, 2-bathroom residence offers a rare opportunity to restore a piece of Berkshire County history while imprinting your own vision on its enduring architecture.

Eric Steuernagle FAIRGROUND REAL ESTATE, INC

Marcel Breuer partner Tician Papachristou designed this home as a private paradise for his three-generation family: a long driveway leads past a tennis court, guest house, swimming pool, gazebo, and gym shed to a three-level modern house evoking the New England barn. From the third-floor master loft suite with private terrace and kitchenette, a skylit central stair leads to the mid-level

Jen Harvey COMPASS MASSACHUSETTS , LLC GB

Reimagined from the studs up by the renowned Wingate Ltd., this spectacular architectural retreat offers ultra-luxury contemporary living on a scenic 2.32-acre Berkshire corridor. This masterfully updated home effortlessly pairs high-design drama with absolute, engineered peace of mind. The Great Room & Chef's Space:Step inside to a sun-drenched, open-concept main floor anchored by a

John Burns WILLIAM PITT SOTHEBY'S - GT BARRINGTON

Spacious 4 bedroom Cape with several useful storage buildings for anyone with a business and attached 2 car garage.Heated sunroom with sliding windows,Eat in kitchen with access to back patio,Livingroom with knotty pine paneling andfireplace with wood burning stove. First floor has 2 bedrooms and a full bathroom with walk in shower offering first floor living.Two additional

Rosemary Baumann HOUSATONIC REAL ESTATE

Set on four private acres along a quiet stretch of road by the Housatonic, this is the kind of place that reveals itself slowly. The driveway is lined with rhododendrons that light up every spring, and the rest of the landscape is paced to bloom straight through summer - fruit trees, azaleas, perennials, all of it planted by someone who clearly knew what they were doing. Out back, a brook babbles

Cameron Volastro WILLIAM PITT SOTHEBY'S - LENOX