#1 in Rural Real Estate Online
Listing Type
Date Listed

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

32 photos
$2,995,000 12.55 acres 8 Beds | 7 Baths | 5981 sqft
651 Boardman St, Sheffield, MA - 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
33 photos
$1,995,000 46.44 acres 5 Beds | 7 Baths | 6636 sqft
1448 South UNDERMOUNTAIN Rd, Sheffield, MA - Berkshire County

46.44 acres Sheffield, MA

MOUNTAIN TOP COMPOUND WITH IMPRESSIVE CONTEMPORARY LOG HOME AND GUEST CABINon 46 acres w/ spring fed ponds, stream, waterfalls & distant sunrise views. A large eastern facing window wall w/ 30 ft ceiling & massive stone fireplace makes the living room the center room of the house. Two story master suite w/ library & fireplace, large deck with hot tub plus 4 guest bedrooms. WATCH VIDEO!
27 photos
$1,575,000 14.7 acres 4 Beds | 4 Baths | 3920 sqft
398 Weatogue Rd, Sheffield, MA - 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.
42 photos
$1,550,000 17.04 acres 4 Beds | 3 Baths | 4892 sqft
1458 Barnum St, Sheffield, MA - 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!
29 photos
$1,400,000 9.57 acres 4 Beds | 4 Baths | 6684 sqft
50 North Undermountain Rd, Sheffield, MA - 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
19 photos
$698,000 2.12 acres 3 Beds | 3 Baths | 2684 sqft
969 SILVER St, Sheffield, MA - Berkshire County

2.12 acres Sheffield, MA

C 2000, Post-and-Beam style home.Sited on one of Sheffield's most prestigious country roads. Immaculate 3 bedroom, 3 bath home, with a bedroom/den, open dining/kitchen, double height living room w fireplace, wood and tile floors,new screened porch, central AC, new 2 car garage,full basement.Timeless design meets the demands of sophisticated life style. Close to GB & Salisbury CT, Twin Lake
13 photos
$599,000 9 acres 8 Beds | 10 Baths | 4314 sqft
94 Maple Ave, Sheffield, MA - 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.
13 photos
$575,000 24.75 acres 1 Bed | 3 Baths | 2519 sqft
164 Ashley Falls Rd, Sheffield, MA - 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.
28 photos
$499,000 2.28 acres 3 Beds | 3 Baths | 2616 sqft
51 Woodbeck Ridge Rd, Sheffield, MA - Berkshire County

2.28 acres Sheffield, MA

Single level contemporary home on a quiet lane surrounded by State owned land and just 4 miles to town. Open plan living with a large Sun Room, finished Media room in the lower level, open covered front porch and deck. Two car garage and nice landscaping. Totally privateSee listing #208671 which with this listing could be a family compound.
29 photos
$479,000 4.5 acres 6 Beds | 3 Baths | 3616 sqft
254 South Main St, Sheffield, MA - Berkshire County

4.5 acres Sheffield, MA

A true Colonial, circa 1760, for residential and/or commercial use. Extraordinary historic integrity: Intact original architectural features include Georgian paneling, wide-board floors, six fireplaces & other museum-quality details. Built as a tavern by Stephen Dewey: a tavern room in the basement! Updated heat & electric, central AC & vac. On 4.5 acres with garage/barn. More land available.
5 photos
$475,000 4.14 acres 5 Beds | 3 Baths | 2450 sqft
1474 County Rd, Sheffield, MA - Berkshire County

4.14 acres Sheffield, MA

Privacy and Space surrounded by protected land, this home has lots of space with distant views. Ten minutes to Butternut for skiing and Gt Barrington for dinner and a movie. Country living with everything close by.
20 photos
$475,000 2.07 acres 3 Beds | 3 Baths | 2670 sqft
33 Woodbeck Ridge Rd, Sheffield, MA - Berkshire County

2.07 acres Sheffield, MA

The perfect single level contemporary home in like new condition adjacent to State owned land and just 4 miles from GuidosTotally private. Open plan living area with sliders to a covered porch and deck, master bedroom with glass doors to deck. Finished family room with a half bath in the lower level.Could be family compound with MLS # 208667
6 photos
$365,000 3.16 acres 3 Beds | 2 Baths | 1332 sqft
820 Salisbury Rd, Sheffield, MA - Berkshire County

3.16 acres Sheffield, MA

Enjoy this quiet setting just 5 minutes from Sheffield center. This immaculate house is move in condition. 3 Bedroom/2 Bath with potential for more. Great yard that goes down to the Schenob Brook.
11 photos
$325,000 4.1 acres 3 Beds | 3 Baths | 2240 sqft
941 Clayton Rd, Sheffield, MA - Berkshire County

4.1 acres Sheffield, MA

Terrific Berkshire County Home in the Ashley Falls Section of Sheffield.This neat-as-a-pin home features 4+ acres, a large Living Room with gas fireplace, Dining Room, Kitchen, 3 Bedrooms, and 2.5 Baths. Also, included: a new trex Deck, an above-ground Pool, and over-sized windows through-out the house. Located close to Housatonic River and Bartholomew's Cobble. A super buy!
12 photos
$95,000 2.5 acres 1 Bed | 1 Bath | 600 sqft
276 Waterfarm Rd, Sheffield, MA - Berkshire County

2.5 acres Sheffield, MA

LITTLE cottage with a BIG basement.The cabin sits on a newer poured foundation that is almost twice as large. Two parcels (1.06ac and 1.44ac) Mostly wooded flat lot with large boulders on a quiet country road close to downtown Sheffield. Needs new septic system.