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Sheffield, Massachusetts: Country Homes, Houses, and Rural Real Estate

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$689,000 5.6 acres 4 Beds | 4 Baths | 3279 sqft
1548 SOUTH UNDERMOUNTAIN Rd, Sheffield, MA 01257 - Berkshire County

5.6 acres Sheffield, MA

LOVELY LIGHT FILLED COLONIAL OVERLOOKING THE HOUSATONIC RIVER VALLEY. BEAUTIFUL MARBLE FIREPLACES, CROWN MOLDNGS AND WOOD FLOORS. FIRST FLOOR BEDROOM WITH SEPARATE BATH, DEN WITH WOODSTOVE (CHECKING ON PERMIT), FORMAL LIVING AND DINING ROOMS, CENTRAL KITCHEN AND GREAT MUDROOM MAKE UP THE FIRST FLOOR. UPSTAIRS ARE THREE BEDROOMS AND A NOVEL IDEA FOR A SPLIT FULL BATH. ATTIC IS A FULL WALK-UP AND
Jennifer Harvey Berkshire Property Agents, LLC
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$2,690,000 12.55 acres 8 Beds | 7 Baths | 5981 sqft
651 Boardman St, Sheffield, MA 01257 - Berkshire County

12.55 acres Sheffield, MA

Beautiful 12.5 acre Berkshire property suitable as a magnificent home or family compound. Panoramic views from a masterfully updated and expanded 1830s Colonial 6 bedroom farmhouse and a 1500 sq ft guest house with a full kitchen, a picturesque 3/4 acre pond, saltwater heated infinity pool, tennis court, post and beam craft barn and kid's playhouse are part of what this property offers. See MORE
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$2,295,000 14.52 acres 3 Beds | 4 Baths | 3552 sqft
514 Rannapo Rd, Sheffield, MA 01257 - Berkshire County

14.52 acres Sheffield, MA

Built in 1785 for Jane Ashley, daughter of Colonel John Ashley, and her husband John Bull, Bull Hill Farm is a masterpiece restoration and re-imagination of a classic New England farm.The house is an exemplary blend of true Colonial & Federal design elements that has been fully renovated and updated with a meticulous eye for detail and with a refined yet whimsical style.
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$1,575,000 14.7 acres 4 Beds | 4 Baths | 3920 sqft
398 Weatogue Rd, Sheffield, MA 01222 - Berkshire County

14.7 acres Sheffield, MA

Sittin' On Top of the WorldA dramatic hilltop setting, a unique contemporary with quality and style throughout, beautiful decks, patios and landscaping, an in ground pool, views forever, and so much more, all combine to make Monarch Hill the ultimate retreat. High above the Housatonic River and bordered by hundreds of acres at Bartholomew's Cobble, this home is designed for peace and comfort.
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$1,550,000 17.04 acres 4 Beds | 3 Baths | 4892 sqft
1458 Barnum St, Sheffield, MA 01257 - Berkshire County

17.04 acres Sheffield, MA

Beautiful mountain views, open pastures & Schenob Brook frontage create the idyllic setting for The Barns, a stylish, spacious, architect-designed home offering privacy & amenities including CAC & sound system. A stunning great room is its centerpiece, complemented by a summer living room, cook's kitchen, library with fireplace, den, artist's studio, more. Truly the ideal home in the Berkshires!
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$1,400,000 9.57 acres 4 Beds | 4 Baths | 6684 sqft
50 North Undermountain Rd, Sheffield, MA 01257 - Berkshire County

9.57 acres Sheffield, MA

Gracious Berkshires Brick FederalThe charm and history of this classic Colonial are evident from the moment you enter. Grand, spacious rooms, 7 fireplaces, high ceilings, a tranquil setting with views to the Berkshire Hills. Updated mechanicals, new deck, Gunite pool, a patio and balcony overlooking the south lawn, a wonderful Gallery space. This is a home with a story, where interesting
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$950,000 24.84 acres 5 Beds | 4 Baths | 3800 sqft
394 Berkshire School Rd, Sheffield, MA 01257 - Berkshire County

24.84 acres Sheffield, MA

THE PERFECT COUNTRY RETREAT FOR LOADS OF FAMILY AND FRIENDS. Surrounded by 25 acres, this private compound offers a 3-4 bedroom contemporary farmhouse; a rustic cottage with a kitchenette and full bath; and a large studio with a kitchenette and full bath above the detached garage. Plenty to do... large lawn, pond, brook for fishing/swimming, hiking trails. All just 5 minutes to Sheffield center.
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$950,000 24.84 acres 5 Beds | 4 Baths | 3800 sqft
394 Berkshire School Rd, Sheffield, MA 01257 - Berkshire County

24.84 acres Sheffield, MA

THE PERFECT COUNTRY RETREAT FOR LOADS OF FAMILY AND FRIENDS. Surrounded by 25 acres, this private compound offers a 3-4 bedroom contemporary farmhouse; a rustic cottage with a kitchenette and full bath; and a large studio with a kitchenette and full bath above the detached garage. Plenty to do... large lawn, pond, brook for fishing/swimming, hiking trails. All just 5 minutes to Sheffield center.
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$899,000 5.66 acres 3 Beds | 4 Baths | 2973 sqft
45 East Rd, Sheffield, MA 01257 - Berkshire County

5.66 acres Sheffield, MA

Beautiful Berkshire contemporary home on 5.66 acres, 3/4 bedrooms, Master bedroom on first floor, 2 separate dressing rooms, Gunite heated pool with a stone deck, architect designed incorporating a 150 year old timber frame barn, silo and cupola, new kitchen with granite and marble counter tops, all top quality materials, fully finished lower level, screened in porch with fireplace, a must see.
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$799,000 5.18 acres 4 Beds | 4 Baths | 3130 sqft
199 Hickey Hill Rd, Sheffield, MA 01230 - Berkshire County

5.18 acres Sheffield, MA

One immediately feels welcomed while driving up the tree-lined driveway into this great property. Enter approximately 3800 square feet of pure delight with tremendous attention to detail and ponderosa pine floors throughout. The open light-filled living room is the center of all action, with seating areas for family and friends plus a wood-burning fireplace.
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$698,000 2.12 acres 3 Beds | 3 Baths | 2684 sqft
969 SILVER St, Sheffield, MA 01257 - Berkshire County

2.12 acres Sheffield, MA

C 2000 POST-AND-BEAM STYLE HOME SITED ON A PRESTIGIOUS COUNTRY ROAD CLOSE TO SALISBURY CT, TWIN LAKES AND GT BARRINGTON. REPURPOSED BARN WOOD WAS USED TO CREATE THIS ARTISTIC AND IMMACULATE HOME. THREE BEDROOMS, THREE BATHS, DEN, OPEN DINING AND KITCHEN, HUGE FOYER. DOUBLE HEIGHT LIVING ROOM WITH A FIREPLACE. WOOD AND CERAMIC FLOORS, SCREENED PORCH, CENTRAL AIR, SEPARATE TWO CAR GARAGE AND GARDENS
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$599,000 9 acres 8 Beds | 10 Baths | 4314 sqft
94 Maple Ave, Sheffield, MA 01257 - Berkshire County

9 acres Sheffield, MA

A majestic home on a peaceful country road, but walking distance to town. Originally built as a B&B, this property boasts 7 bedrooms, each with an en suite bath PLUS an owners quarters. A huge porch, an inground pool, lovely fireplace and large kitchen.
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$579,000 2.23 acres 3 Beds | 2 Baths | 4609 sqft
775 North Main St, Sheffield, MA 01257 - Berkshire County

2.23 acres Sheffield, MA

Great investment opportunity! Home of a successful antiques shop for over 30 years. Property consists of 3 large retail spaces with ample parking, plus attached 2-bedroom, 1 1/2 bath living quarters. Kitchen features walk-in pantry, comfortable den opens to lovely sun room. Full attic offers great potential for additional living space. Spacious, private backyard.
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$549,000 24.75 acres 1 Bed | 3 Baths | 2519 sqft
164 Ashley Falls Rd, Sheffield, MA 01257 - Berkshire County

24.75 acres Sheffield, MA

EXQUISITE RENOVATION OF A HISTORIC TRAIN DEPOT. Transformed by a talented artist, this post and beam train depot has been renovated with the finest finishes, while retaining many of its original details. Nearly five pastoral acres include wildflower meadows, vegetable beds, and perennial gardens. Privacy on nearly 25 acres close to the Connecticut border, yet just 15 minutes to Great Barrington.
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$495,000 6.67 acres 4 Beds | 3 Baths | 2464 sqft
1161 Home Rd, Sheffield, MA 01257 - Berkshire County

6.67 acres Sheffield, MA

Private setting for this charming reproduction colonial home situated on 6.67 acres. This 2500 sq. ft. home has 4 bedrooms 2.5 baths....wonderful feeling of spaceLand has established gardens and offers great opportunity for those who love horses. A pleasure to show!