Sheffield Homes for Sale

/40
$499,000
- 6 Beds
- 2.5 Baths
- 3,184 Sq Ft
119 S Main St, Sheffield, MA 01257

A unique opportunity to make this terrific property your own, with a separate bungalow apartment for income or other home business uses. Property features a 6 bedroom, 2 bath 1880's Victorian with a classic yet casual style. First floor features a sunny living room, large country kitchen, formal dining room w/ built-ins, and front parlor/bedroom. Second floor offers 5 bedrooms, 2 full baths, and

Dan Alden

ALDEN COUNTRY REAL ESTATE SERVICES

(413) 481-1637

119 S Main St, Sheffield, MA 01257
/53
$695,000
- 4 Beds
- 4 Baths
- 3,455 Sq Ft
64 Hewins St, Sheffield, MA 01257

A rare & authentic 1842 post & beam farmhouse w/ many original details. This one-of-a-kind antique home awaits the reinvention & stewardship of it's next owners. In the same family for the last 125 years, and with just two prior owners since being built, the structure features post & beam construction, two original fireplaces, antique hardware, woodwork and doors that exemplify early American

Dan Alden

ALDEN COUNTRY REAL ESTATE SERVICES

(413) 296-3500

64 Hewins St, Sheffield, MA 01257
/9
$379,500
- Land
- 6 Acres
- $60,720 per Acre
0 S Main St, Sheffield, MA 01257

Mountain views with Rt 7 access. Whether you are interested in a private residence to farm, raise horses, or escape the city life or if you are looking for a business opportunity with amazing Rt 7 exposure this land is the perfect opportunity. Totaling 6.25 acres of completely usable, flat, dry land. Currently the fields are hayed and have an approximate 1 acre vineyard. The 6.25 acres is made up

Grace Golden Equine Homes Real Estate, LLC

0 S Main St, Sheffield, MA 01257
/45
$999,000
- Land
- 17 Acres
- $57,779 per Acre
1166 Rannapo Rd, Sheffield, MA 01257

It's no wonder why this property is the home of Berkshire county's oldest elm tree! The abundant sunshine, quietude and peace would make anybody want to set down roots and stay a while. This light filled home has refinished wood floors throughout the main level. Kitchen has granite counters, ample cabinet space, pantry and large island. As part of the open floor plan there is a bright dining

Grace Golden Equine Homes Real Estate, LLC

1166 Rannapo Rd, Sheffield, MA 01257
/25
$795,000 Open Sat 9AM - 10:45AM
- 3 Beds
- 2 Baths
- 1,730 Sq Ft
1427 Hewins St, Sheffield, MA 01257

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 with a lovely backyard patio--perfect for indoor-outdoor living. Ideal for both outdoor enthusiasts, with hiking, biking, and skiing nearby or one could just enjoy

Claire Pollart LANCE VERMEULEN RE, INC

1427 Hewins St, Sheffield, MA 01257
/34
$775,000
- 4 Beds
- 2 Baths
- 2,310 Sq Ft
662 Foley Rd, Sheffield, MA 01257

Nature-Lover's Retreat Enjoy the best of country living on 4.55 acres in Sheffield. Tucked away, this sunlit Cape offers privacy, and timeless charm. A wooded drive leads to a 4-bed, 2-bath home with 2,300 sq ft of living space and a warm, open-concept layout featuring wood-beamed ceilings and a spacious great room addition. The second-floor primary suite offers a peaceful escape, while the

Claire Pollart LANCE VERMEULEN RE, INC

662 Foley Rd, Sheffield, MA 01257
/40
$1,240,000
- 5 Beds
- 4.5 Baths
- 3,100 Sq Ft
60 Parsley Ln, Sheffield, MA 01257

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

60 Parsley Ln, Sheffield, MA 01257
/75
$895,000
- 9 Beds
- 7 Baths
- 5,267 Sq Ft
567 S Main St, Sheffield, MA 01257

Charming Multi-Family Property in Sheffield. Welcome to a rare homestead tucked away on 11 acres of peace and privacy in Sheffield. This inviting property offers an ideal setup for multi-generational living or families seeking extra space and privacy. Main House with (4) 1BR and (1) 2BR apartments, a second 3 BR home, and a three-bay garage. A short drive to Great Barrington (15 mins) and

Claire Pollart LANCE VERMEULEN RE, INC

567 S Main St, Sheffield, MA 01257
/17
$845,000
- 3 Beds
- 2.5 Baths
- 2,408 Sq Ft
1786 S Undermountain Rd, Sheffield, MA 01257

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

1786 S Undermountain Rd, Sheffield, MA 01257
/54
$1,190,000
- 4 Beds
- 2.5 Baths
- 3,155 Sq Ft
405 S Undermountain Rd, Sheffield, MA 01257

Idyllic Contemporary Cape on Sprawling 13 Acres in Sheffield - Welcome to 405 South Undermountain Road, where the charm of a classic cape meets the allure of modern living on 13 private acres in Sheffield. Built in 1955 and beautifully updated, this home strikes a harmonious balance between comfort and elegance. Offering an open floor plan with 2 full baths, one 1/2 bath and a functional tiled

Karen Climo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

405 S Undermountain Rd, Sheffield, MA 01257
/42
$995,000 Open Sat 11AM - 12:30PM
- 3 Beds
- 3.5 Baths
- 2,600 Sq Ft
594 Shunpike Rd, Sheffield, MA 01257

Beautifully renovated 2600 sq. ft. Gambrel-style home offering the perfect balance of privacy, comfort, and modern convenience. Step into a welcoming, open foyer that leads to an expansive living space with all-new features, including wood flooring, central air/heat, a full house generator, & updated plumbing/electrical systems. The heart of the home is a brand-new kitchen, complete with sleek

Claire Pollart LANCE VERMEULEN RE, INC

594 Shunpike Rd, Sheffield, MA 01257
/33
$798,000
- 3 Beds
- 2.5 Baths
- 3,082 Sq Ft
86 Main St, Sheffield, MA 01257

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

86 Main St, Sheffield, MA 01257
/37
$1,475,000
- 1 Bed
- 2 Baths
- 1,296 Sq Ft
481 Shunpike Rd, Sheffield, MA 01257

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

481 Shunpike Rd, Sheffield, MA 01257
/60
$998,000
- 3 Beds
- 3 Baths
- 1,800 Sq Ft
856 Barnum St, Sheffield, MA 01257

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

856 Barnum St, Sheffield, MA 01257
/39
$1,275,000
- 4 Beds
- 5 Baths
- 3,528 Sq Ft
1669 Silver St, Sheffield, MA 01257

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

1669 Silver St, Sheffield, MA 01257
/18
$795,000 Open Sun 10AM - 12PM
- 3 Beds
- 3.5 Baths
- 1,991 Sq Ft
483 Home Rd, Great Barrington, MA 01230

OPEN HOUSE SUNDAY 8/10, 10 am-12 noon | 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

Suzann Ward HOUSATONIC REAL ESTATE

483 Home Rd, Great Barrington, MA 01230
/54
$649,000
- 3 Beds
- 2.5 Baths
- 1,822 Sq Ft
1862 Home Rd, Great Barrington, MA 01230

Bordering large parcels of protected land, including the Appalachian Trail, this super-easy-to-maintain contemporary/split-level is in move-in condition. Nicely sited on one acre of land, offering a quiet location with privacy. The interior is light and bright, and the floor plan provides an efficient use of space with distinct gathering areas. The vaulted ceiling living room has a gas

Lori Rose STONE HOUSE PROPERTIES, LLC

1862 Home Rd, Great Barrington, MA 01230
/13
$350,000
- 3 Beds
- 1 Bath
- 900 Sq Ft
412 Berkshire School Rd, Sheffield, MA 01257

1995 split level home on .50 acres walking distance to the village of Sheffield. 3 bedrooms 1 full bath....eat in kitchen, living room....unfinished lower level....electric and forced hot air propane fired heat, vinal siding......septic.(Title 5 completed)....private water company

Patrice Melluzzo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

412 Berkshire School Rd, Sheffield, MA 01257
/44
$685,000
- 3 Beds
- 3 Baths
- 2,395 Sq Ft
649 Hewins St, Sheffield, MA 01257

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

649 Hewins St, Sheffield, MA 01257
/43
$475,000
- 4 Beds
- 2 Baths
- 1,560 Sq Ft
127 Old Joe Rd, Great Barrington, MA 01230

Nestled on a quiet country road, this well-kept ranch offers the ease of single-level living with ample space to relax, entertain, and make your own. The home features an inviting floor plan with plenty of natural light and room for upgrades, allowing you to personalize each space to your taste.Enjoy seamless indoor-outdoor living with a large back deck--perfect for gatherings or quiet mornings

Tony Segalla LANCE VERMEULEN RE, INC

127 Old Joe Rd, Great Barrington, MA 01230
/21
$110,000
- Land
- 7 Acres
- $15,559 per Acre
730 Clayton Rd, Sheffield, MA 01222

BOG LOVERS, come look. Officially designated to be a Bog, this property could be a great one to own, for observing its nature views that change the year around. Whether you would want to build a home, or build a viewing platform for regular visits, it has 7+ acres with roughly 60-70% in a bog like status, the remainder being usable for building and walking along the bog's boundaries. All earlier

Robin Leech Robinson Leech Real Estate

730 Clayton Rd, Sheffield, MA 01222
/53
$695,000
- 6 Beds
- 5 Baths
- 4,572 Sq Ft
604 Sheffield Plain, Sheffield, MA 01257

A rare opportunity awaits in the heart of historic Sheffield. This exceptional multi-unit property, originally a classic 1740s farmhouse, has been thoughtfully converted into a lucrative income-producing asset while retaining its timeless New England charm. Perfectly positioned just south of Great Barrington, it offers both tenants and owners a convenient commute to local attractions, work, and

Tony Segalla LANCE VERMEULEN RE, INC

604 Sheffield Plain, Sheffield, MA 01257
/82
$4,500,000
- 4 Beds
- 3 Baths
- 5,256 Sq Ft
381 Sheffield-Egremont Rd, Sheffield, MA 01257

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

381 Sheffield-Egremont Rd, Sheffield, MA 01257
/54
$649,000
- 5 Beds
- 2.5 Baths
- 2,750 Sq Ft
168 Main St, Sheffield, MA 01257

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

168 Main St, Sheffield, MA 01257
/44
$1,600,000
- 9 Beds
- 4.5 Baths
- 8,406 Sq Ft
2049 S Undermountain Rd, Sheffield, MA 01257

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

2049 S Undermountain Rd, Sheffield, MA 01257
/30
$695,000
- 3 Beds
- 6 Baths
- 4,044 Sq Ft
1180 Ashley Falls Rd Unit A,B,C,D,E, Sheffield, MA 01222

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

1180 Ashley Falls Rd Unit A,B,C,D,E, Sheffield, MA 01222
/53
$3,250,000
- 4 Beds
- 3.5 Baths
- 3,459 Sq Ft
232 Giberson Rd, Sheffield, MA 01257

The Quarry - A One-of-a-Kind Berkshire Estate on 60 Private Acres!Singular, stunning, and secluded--the quarry pool at the heart of this 60-acre Berkshire estate is truly one of its kind: the culmination of geology, industry, and artistry. Carved into a reclaimed limestone quarry and framed by towering stone walls and a 16-foot waterfall, the quarry pool is a marvel in and of itself--equal parts

Jared Kelly WILLIAM PITT SOTHEBY'S - GT BARRINGTON

232 Giberson Rd, Sheffield, MA 01257
/9
$139,000
- Land
- 6 Acres
- $22,720 per Acre
0 Amory Ln, Southfield, MA 01259

Discover the perfect setting for your custom retreat on this expansive 6+ acre lot nestled on a tranquil cul-de-sac off a scenic Berkshire country road. Located in New Marlborough, with a small portion extending into Sheffield, this beautiful parcel offers endless possibilities for your vision. Enjoy the serenity of nature, the charm of rural living, and the potential for lovely views. Whether

Kate Lascar COMPASS MASSACHUSETTS , LLC GB

0 Amory Ln, Southfield, MA 01259
/10
$114,900
- Land
- 1.45 Acres
- $79,241 per Acre
0 Bunce Rd Unit 245787, Sheffield, MA 01257

Situated in a peaceful well-established neighborhood, and surrounded by a natural buffer of mature trees, this beautiful 1.45 acre lot is cleared and ready for construction. Underground phone, cable, and electric utilities are conveniently located right at the end of the roughed-in driveway. Percolation test was completed in 2023. This charming parcel is the last available building lot on this

Vashti Poor LANCE VERMEULEN RE, INC

0 Bunce Rd Unit 245787, Sheffield, MA 01257
/61
$2,500,000
- 4 Beds
- 4.5 Baths
- 3,100 Sq Ft
1373 Boardman St, Sheffield, MA 01257

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

1373 Boardman St, Sheffield, MA 01257
/11
$795,000
- Land
- 18 Acres
- $44,167 per Acre
0 Bull Hill Rd, Sheffield, MA 01257

OWNER FINANCING AVAILABLE! Eighteen acres on the quietest dirt road with its own exceptional landscape feature: a boulder-strewn, mossy-rocked cobble. The cobble bisects a flat three acre cleared field to the east, and a wooded forest with old stone wall remnants to the west. Live amongst the ancient spirits in whatever beautiful house you build. Fifteen wooded acres in Chapter 61A. Buyer to

Kristin Clayborne WILLIAM PITT SOTHEBY'S - GT BARRINGTON

0 Bull Hill Rd, Sheffield, MA 01257
/9
$199,000
- Land
- 1.30 Acres
- $153,077 per Acre
1699 N Main St, Sheffield, MA 01257

COMMERCIAL AREA ON THE SHEFFIELD/GREAT BARRINGTON LINE OFF OF BUSY ROUTE 7. SOME WETLANDS BUT A WORTHY LOCATION. NICE WITH LEVEL LAWN. THERE ARE NOT MANY LOTS LEFT ALONG THIS POPULAR COMMERCIAL CORRIDOR.

Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

1699 N Main St, Sheffield, MA 01257
/30
$345,000
- 3 Beds
- 2.5 Baths
- 1,536 Sq Ft
179 S Main St, Sheffield, MA 01257

Step back in time with this charming 1826 gem, nestled in the quiet village of Sheffield on Main Street. Featuring 3 bedrooms, 3 bathrooms, and a first-floor ensuite, this home offers classic simplicity and historical integrity. The screened-in porch is perfect for enjoying the peaceful surroundings, while the 1-car garage adds convenience. Untouched by modern trends, this property is a blank

Tony Segalla LANCE VERMEULEN RE, INC

179 S Main St, Sheffield, MA 01257
/43
$399,900
- 3 Beds
- 1.5 Baths
- 1,617 Sq Ft
454 Sheffield Plain, Sheffield, MA 01257

Beautifully restored New England Farmhouse located in the quaint town of Sheffield. Exterior features fresh paint, new vinyl windows, and a new roof. Stepping inside this home has retained most of the original wide-plank hardwood flooring that has been restored on the first and second levels. Throughout the first floor there are custom updates in the half bathroom with new ceramic tiles, a new

Cory Evangelisto NOCHER REALTY

454 Sheffield Plain, Sheffield, MA 01257
/2
$99,000
- 2 Beds
- 1 Bath
- 1,230 Sq Ft
16 Lilac Ln, Sheffield, MA 01257

AS IS, Total rehab, most likely a tear down, electric available, no septic. A drive by is requested before making showing appointment. Showings will be scheduled starting Monday Aug. 11

Timothy Harrigan BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

16 Lilac Ln, Sheffield, MA 01257
/24
$315,000
- 6 Beds
- 5.5 Baths
- 3,683 Sq Ft
175 Main St, Sheffield, MA 01257

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

175 Main St, Sheffield, MA 01257

Massachusetts Berkshire County Sheffield Sheffield

Frequently Asked Questions Why Live in Sheffield

Is Sheffield a good place to live?

Sheffield is a good place to live. Sheffield is considered very car-dependent and somewhat bikeable. Sheffield is a neighborhood with a crime score of 1, making it safer than the average neighborhood in the U.S. Sheffield has 1 park for recreational activities. It has a median age of 53. The average household income is $112,124 which is above the national average. College graduates make up 35.2% of residents. A majority of residents in Sheffield are home owners, with 23.1% of residents renting and 76.9% of residents owning their home. A local real estate agent serving Sheffield can help you decide if this neighborhood is the right one for you. Learn more on our Sheffield neighborhood guide.

Is Sheffield, MA a safe neighborhood?

Sheffield, MA is safer than the average neighborhood in the United States. It received a crime score of 1 out of 10.

How much do you need to make to afford a house in Sheffield?

The median home price in Sheffield is $482,263. If you put a 20% down payment of $96,500 and had a 30-year fixed mortgage with an interest rate of 6.63%, your estimated principal and interest payment would be $2,470 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $106K a year to afford the median home price in Sheffield. The average household income in Sheffield is $112K.

What are the best public schools in Sheffield?

The best public schools that serve Sheffield are:

New Marlborough Central School has a B+ Niche grade and a student teacher ratio of 8:1.
Mt. Everett High School has a B Niche grade, a student teacher ratio of 7:1 and an average review score of 4.0.
Undermountain Elementary School has a B Niche grade and a student teacher ratio of 9:1.

What are the best private schools in Sheffield?

The best private schools that serve Sheffield are:

Berkshire School has an A+ Niche grade, a student teacher ratio of 4:1 and an average review score of 4.5.

What are the most popular zip codes in Sheffield, Sheffield, MA?

The most popular zip codes in Sheffield, Sheffield, MA include 01257, 01230, 01222, 06068 and 01259.

What are the most popular neighborhoods near Sheffield, Sheffield, MA?

The most popular neighborhood near Sheffield, Sheffield, MA is North East.

Learn more about living in Sheffield

Home Trends in Sheffield, MA

Housing Trends

Median Single Family Sale Price

$449,990

Average Price Per Sq Ft

$218

Number of Homes for Sale

Last 12 months Home Sales

Median List Price

$482,263

How to Buy a Home How to Finance a Home How to Sell a Home

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