45 Sheffield, MA 01257 Real Estate Listings

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Est. Payment$550,000
3 Beds | 3 Baths | 130,680 Sqft

1220 Berkshire School Rd, Sheffield, MA 01257

House For Sale

A home like no other, this classic Berkshire chalet style lodge is conveniently situated and close to everything, but feels like a fairy tale escape. Whimsical wood detailing on the exterior juxtaposed with natural field stone help create a striking and dramatic picture. Beautiful grounds with mature landscaping and plenty of room to spread out round out this picturesque scene.This home boasts many original details, such as wood floors, gingerbread trim, and built in cabinetry. There are three bedrooms and full baths, with an additional option for an in law suite, short term rental, or 4th bedroom, according to your needs. Come see and let your imagination run wild!Additional land is available.

Est. Payment$349,000
3 Beds | 2 Baths | 113,256 Sqft

319 Berkshire School Rd, Sheffield, MA 01257

House For Sale

Charming Farmhouse overlooking Schenob Brook. Detached Barn w/workshop & storage.Perennial gardens. Walk to village. Close to all Berkshire Amenities.

Est. Payment$935,000
3 Beds | 3 Baths | 303,613 Sqft

242 Hickey Hill Rd, Sheffield, MA 01257

House For Sale

This custom-built Bensonwood Timber Frame home was designed w/ a classic open living floor plan & built to Energy Star standards. The craftsmanship, materials & design details are extraordinary. The main living area w/ vaulted ceiling has an abundance of windows & natural light. The gorgeous Berkshire vistas & views can be enjoyed throughout the house. The well-equipped cook's kitchen opens to the dining/living area and the raised hearth fireplace. The screened porch & patio were designed to take in the evening sunsets. There is first floor master suite with walk-in closet. Central AC. This beautiful property has been impeccably maintained. A great location convenient to the southern Berkshire & northern Litchfield county recreational & cultural venues. Only 8 miles to Great Barrington.

Est. Payment$585,000
3 Beds | 3 Baths | 174,240 Sqft

249 Boardman St, Sheffield, MA 01257

House For Sale

Set well back from the road, on four lush riverfront acres, this spacious, meticulously maintained home is the perfect retreat offering both privacy and proximity to Berkshire attractions. Open, light-filled living spaces abound on the main floor. An updated, classically styled kitchen opens to a Great Room with a wood-burning fireplace, dining area, half bath, and easy deck access with river views. A breezeway attaching the 2 car garage is a perfect mudroom. Upstairs, a generously sized master bedroom features a wood-burning fireplace and en suite bath, and 2 additional bedrooms share a full bath. A 1st floor office/den and basement rec room offer even more space for work or play. Or better yet, step outside and enjoy the sights, sounds, and serenity of this unique riverfront property.

Est. Payment$350,000
3 Beds | 2 Baths | 45,302 Sqft

64 Kellogg Rd, Sheffield, MA 01257

House For Sale

3 bedroom/2 bath ranch in the heart of the Berkshires. Nicely sized living room with field stone fireplace and custom built in bookcases. Sunny galley kitchen with good work space and light. Finished attic. Step down to the family room which has a wood stove and french doors which lead to the front stone path and sliding doors leading to the sunroom. The rear deck leads to a sunny huge backyard which is fully fenced and offers privacy and great gardening potential. Nice separation between the guest rooms & the master suite. Central A/C, hardwood floors, attached garage. Near Guido's, Appalachian Trail, Great Barrington, for the best in shopping and dining, schools, and Tanglewood. Finished attic not included in sq. ft. calculation. It's a wonderful life.

Est. Payment$219,000
2 Beds | 1 Bath | 10,890 Sqft

674 Rannapo Rd, Sheffield, MA 01257

House For Sale

Situated on one of the prettiest roads in the Berkshires and surrounded by historic homes and conservation lands, this sweet 2-bedroom cottage combines a beautiful location with a casual style that's rare to find. Swan Cottage has a bright and cheerful interior with an open, freshly remodeled kitchen featuring quartz countertops and white cabinetry. The adjoining dining area features beadboard wainscoting and a large bay window. Sliding glass doors lead from the living room, complete with native stone fireplace, to a deck where one can kick back and relax while soaking in the southwesterly views towards Bartholomew's Cobble and Cooper Hill. Updated electrical, plumbing and new oil tank make this package even more appealing.

Est. Payment$16,000,000
11 Beds | 7 Baths | 3,702,600 Sqft

2080 Undermountain Rd, Sheffield, MA 01257

House For Sale

The Jewel of New England... Offered for the first time in four decades, this 85 acre Berkshire mountainside campus awaits your imagination. This property offers an atmosphere for breakout creative expression with great potential for an enterprise for retreats, wellness center, writers/ artists workshops, educational endeavors or your family's private estate. The property consists of 12 buildings; conference halls, dining/ meeting facilities, lodging accommodations, offices and an historic Queen Anne manor house sitting on a knoll with breathtaking views. 40 years of stewarding this campus where thousands of participants made life long memories, the owners are ready to pass it on. Let their growth be your opportunity. For details & digital brochure please see jewelinnewengland.com

Est. Payment$315,000
4 Beds | 2 Baths | 38,333 Sqft

575 Sheffield Plain , Sheffield, MA 01257

House For Sale

Great curb appeal! Convenient to all Berkshire amenities. Beautiful views. One of the most distinguished antique colonials in beautiful Sheffield, Massachusetts, has come on the market for the first time in over thirty years. Four bedrooms, two baths, updated mechanicals. Three-car detached garage. Residential and/or commercial uses.

Est. Payment$899,000
4 Beds | 4 Baths | 104,980 Sqft

121 Hickey Hill Rd, Sheffield, MA 01257

House For Sale

looking for that little piece of Berkshire sky? A quiet place to watch the sunset? just gaze at the stars as you relax on your back deck. This counrty home is just the place. Situated on a hilltop in Sheffield drenched in sunlight. If your looking for quiet, mountain views, privacy, land, move in ready and under a 3 hour drive from the city, you Must come and see this house!Four bedrooms and baths. A beautiful stone fireplace that anchors the living room for those chilly winter nights.Formal dining room for the holidays. A wonderful eat in kitchen that opens up to a great four season sun room. Slip outside onto the large deck for entertaining, or just stroll around the lovely perenial gardens. 10 miles to Great Barrington and 20 to Tanglewood. Come see what others have missed!

Est. Payment$187,500
2 Beds | 1 Bath | 43,560 Sqft

626 Salisbury Rd, Sheffield, MA 01257

House For Sale

Sweet farm house that needs some TLC.Move in and fix it up to suit yourself. Quiet location with a nice yard with screened porch for relaxing.NO APPLIANCES.

Est. Payment$359,000
2 Beds | 2 Baths | -- Sqft

96 Main St, Sheffield, MA 01257

House For Sale

Nearly 3,000 sq. ft. and +/-0.33 acres in the center of downtown Sheffield this turn-of-the-century building has old world craftsmanship and charm. Great visibility and easily accessible this property includes a 2-bedroom apartment located on the second floor.

Est. Payment$399,000
8 Beds | 6 Baths | 374,616 Sqft

1434 North Main St, Sheffield, MA 01257

Multi Family For Sale

GREAT OPPORTUNITY IN A CONVENIENT LOCATION! Two separate buildings each with 3 potential rental income apartments; Main building can stay as is or be converted back into a single family; live in one, rent the others; solid rental history.

Est. Payment$749,000
3 Beds | 4 Baths | 319,992 Sqft

264 Brush Hill Rd, Sheffield, MA 01257

House For Sale

Tucked away on a quiet dirt road sits this spacious, beautifully maintained 1990s contemporary. Enjoy total privacy and pond frontage only 10 minutes from downtown Great Barrington, 20 from two major ski areas and 25 from Tanglewood. The privacy of this home can be enjoyed from the abundance of outdoor space as well as the inviting three-season screened porch surrounded by amid lush wooded conservation land. Inside you'll find Cathedral ceilings, a stunning stone fireplace, Cook's kitchen with an abundance of maple cabinetry, formal dining, a cozy den with an additional fireplace and a large master suite. The Master Suite features cathedral ceilings, his and hers walk-in closets and an oversized bathroom featuring his and hers sinks, tiled shower and a large soak/jet tub.

Est. Payment$399,000
4 Beds | 3 Baths | 134,165 Sqft

25 Cross Rd, Sheffield, MA 01257

House For Sale

This 4 BR/3 BA 2,568 sq.ft. home features an open floor plan, a renovated kitchen with tile back splash and glass sliders that lead to a large private deck. The deck looks out on mature fruit trees and 3 beautiful acres of land that abuts preserved state land on one side. Built in 1998, the lower level was finished by the sellers 10 years ago. They added about 800 sq. ft. of living space. The lower level features a large space that could be used for TV, exercise or play. It is equipped with a full bath, closets with organizers and a room that could be utilized as a study. The possibilities are endless. Loved and cared for in a meticulous manner, this is an excellent opportunity to live in a coveted Berkshire location.

Est. Payment$149,500
1 Bed | 1 Bath | 24,829 Sqft

358 South Main St, Sheffield, MA 01257

House For Sale

Sweet 1977 Ranch style home set back from the Main Road on a inviting half acre lot with a current passed Title V/septic system for two bedrooms, Sheffield Town Water and a full dry basement. Passed on to the current Owners there has been interior taking down of walls and new sheet-rock work in progress. A new Owner could define the light filled space as needed. One bedroom...all open...partial dividers. Think of it as a small blank canvas for a handy creative with hammer and nails.

Est. Payment$479,000
3 Beds | 3 Baths | 43,560 Sqft

27 Main St, Sheffield, MA 01257

House For Sale

Zoned residential and/or commercial in the heart of historic Sheffield Village, this 3 bedroom generously proportioned Greek Revival artfully blends charming details of the of the past with modern conveniences of today and is perfect for LIVE-WORK. The grand entry hall, dominated by a handsome stairway, flows graciously to the front parlor, formal dining room, and large country kitchen. Period elements include meticulously restored classic moldings, high beamed ceilings, 6 over 6 windows, 3 fireplaces, elegant wood floors, and a cavernous easily accessed attic, which offers multiple use possibilities. The expanded, vaulted ceiling kitchen features a center island, granite counters, updated appliances, and walls of windows surrounding an inviting and comfortable eating area.

Est. Payment$450,000
3 Beds | 2 Baths | 21,780 Sqft

69 East Rd, Sheffield, MA 01257

House For Sale

Infinite charm in this 1700s antique stunner. Once an early tavern that centered around an expansive stone hearth w/ authentic 18th century features. The house boasts original wide plank floors & exposed beams on ceilings throughout.Eat-in sunny kitchen area that extends into the tavern room. The tavern area has a large hearth w/ wood stove insert & french doors overlooking the yard. There are 5 original fireplaces, 2 of these in the bedrooms. Original doors, built in cupboards & period hardware. Large bonus room on third floor that would make a great studio or playroom. Forced hot air w/ newer heating system, roof, electrical & masonry work. Poured concrete foundation & garden shed. Sunny & happy lot on a quiet dead end street. Make this vintage treasure your next home.

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