Sheffield, MA Homes

/41
$499,000 Pending
- 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
/41
$475,000 Sold Aug 21, 2025

163 Main St, Sheffield, MA 01257
- 3 Beds
- 2 Baths
- 2,152 Sq Ft
- Built 1805
Last Sold Summary
- 17% Below List Price
- $221/SF
- 321 Days On Market
Current Estimated Value $499,959

Last Listing Agent Vashti Poor WILLIAM RAVEIS - BERKSHIRE

163 Main St, Sheffield, MA 01257

/31
Not Listed For Sale

206 E Main St, Ashley Falls, MA 01222
- 3 Beds
- 2 Baths
- 2,160 Sq Ft
- Built 1850
206 E Main St, Ashley Falls, MA 01222

Last Sold Summary
- $163/SF
- 167 Days On Market
Last Sold Price $351,250

Last Listing Agent Cory Evangelisto NOCHER REALTY

/55
$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 WILLIAM RAVEIS - BERKSHIRE

168 Main St, Sheffield, MA 01257
/21
$168,000 Sold Aug 11, 2025

339 Clayton Rd, Sheffield, MA 01222
- 2 Beds
- 1 Bath
- 1,096 Sq Ft
- Built 1952
Last Sold Summary
- 50% Below List Price
- $153/SF
- 318 Days On Market
Last Listing Agent Eric Steuernagle FAIRGROUND REAL ESTATE, INC

339 Clayton Rd, Sheffield, MA 01222

/72
Est $373,224 Not Listed For Sale

136 Clayton Rd, Ashley Falls, MA 01222
- 4 Beds
- 2 Baths
- 1,770 Sq Ft
- Built 1955
136 Clayton Rd, Ashley Falls, MA 01222

Last Sold Summary
- 13% Above List Price
- $187/SF
- 122 Days On Market
Last Sold Price $330,650

Last Listing Agent Wayne Ditore BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD

/40
$970,000
- 5 Beds
- 4.5 Baths
- 3,024 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 WILLIAM RAVEIS - BERKSHIRE

60 Parsley Ln, Sheffield, MA 01257
/68
$1,350,000 Sold Mar 27, 2026

20 Sheffield-Egremont Rd, Great Barrington, MA 01230
- 4 Beds
- 3.5 Baths
- 3,240 Sq Ft
- Built 1909
Last Sold Summary
- 3% Below List Price
- $417/SF
- 10 Days On Market
Last Listing Agent Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

20 Sheffield-Egremont Rd, Great Barrington, MA 01230

/43
Est $621,225 Not Listed For Sale

345 Miller Ave, Sheffield, MA 01257
- 3 Beds
- 2 Baths
- 2,081 Sq Ft
- Built 1942
345 Miller Ave, Sheffield, MA 01257

Last Sold Summary
- 9% Above List Price
- $274/SF
- 13 Days On Market
Last Sold Price $569,500

Last Listing Agent Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

/53
$695,000 Pending
- 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 WILLIAM RAVEIS - BERKSHIRE

604 Sheffield Plain, Sheffield, MA 01257
/59
$2,295,000 Sold Jun 27, 2025

246 County Rd, Sheffield, MA 01257
- 4 Beds
- 3.5 Baths
- 3,150 Sq Ft
- Built 1915
Last Sold Summary
- $729/SF
- 1 Day On Market
Current Estimated Value $2,117,973

Last Listing Agent Fintan Hanley COMPASS MASSACHUSETTS , LLC GB

246 County Rd, Sheffield, MA 01257

/46
Est $1,995,389 Not Listed For Sale

403 S Undermountain Rd, Sheffield, MA 01257
- 3 Beds
- 4.5 Baths
- 3,000 Sq Ft
- Built 2016
403 S Undermountain Rd, Sheffield, MA 01257

Last Sold Summary
- 13% Below List Price
- $767/SF
- 88 Days On Market
Last Sold Price $2,300,000

Last Listing Agent Tom Lynch COMPASS MASSACHUSETTS , LLC GB

/29
$775,000 Pending
- 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 to a lovely backyard patio--perfect for indoor-outdoor living. Nearby hiking, biking, and skiing offer endless recreation, or simply relax and enjoy the peaceful

Claire Pollart WILLIAM RAVEIS - BERKSHIRE

1427 Hewins St, Sheffield, MA 01257
/35
$350,000 Sold Dec 23, 2025

2105 S Undermountain Rd, Sheffield, MA 01257
- 3 Beds
- 2.5 Baths
- 3,217 Sq Ft
- Built 1796
Last Sold Summary
- 29% Below List Price
- $109/SF
- 85 Days On Market
Current Estimated Value $383,173

Last Listing Agent Dan Alden ALDEN COUNTRY REAL ESTATE SERVICES

2105 S Undermountain Rd, Sheffield, MA 01257

/22
Est $666,609 Not Listed For Sale

169 Ashley Falls Rd, Sheffield, MA 01257
- 3 Beds
- 2.5 Baths
- 2,016 Sq Ft
- Built 1840
169 Ashley Falls Rd, Sheffield, MA 01257

Last Sold Summary
- 16% Above List Price
- $285/SF
- 3 Days On Market
Last Sold Price $575,000

Last Listing Agent Claire Pollart WILLIAM RAVEIS - BERKSHIRE

/56
$899,000
- 3 Beds
- 3.5 Baths
- 2,748 Sq Ft
594 Shunpike Rd, Sheffield, MA 01257

The Ultimate Berkshire Retreat: Designer Luxury with Versatile Income Potential.Experience the pinnacle of refined living in this ''essentially brand new'' masterpiece by Wingate Ltd. Spanning 2,748 sq. ft. across three levels, this reimagined residence sits on one of the Berkshires' most scenic corridors, surrounded by rolling dairy farms and dramatic mountain vistas.Designed for Luxury &

John Burns WILLIAM PITT SOTHEBY'S - GT BARRINGTON

594 Shunpike Rd, Sheffield, MA 01257
/47
$825,000 Sold Sep 15, 2025

20 Hillside Ln, Sheffield, MA 01222
- 3 Beds
- 2 Baths
- 2,057 Sq Ft
- Built 1992
Last Sold Summary
- 8% Below List Price
- $401/SF
- 61 Days On Market
Current Estimated Value $827,152

Last Listing Agent Sarah Dixon WILLIAM RAVEIS - BERKSHIRE

20 Hillside Ln, Sheffield, MA 01222

/31
Est $1,051,791 Not Listed For Sale

960 S Undermountain Rd, Sheffield, MA 01257
- 4 Beds
- 3 Baths
- 2,289 Sq Ft
- Built 1764
960 S Undermountain Rd, Sheffield, MA 01257

Last Sold Summary
- 7% Above List Price
- $428/SF
- 116 Days On Market
Last Sold Price $980,000

Last Listing Agent Mark Rosengren WILLIAM RAVEIS - BERKSHIRE

/33
$775,000
- 3 Beds
- 2.5 Baths
- 3,082 Sq Ft
86 Main St, Sheffield, MA 01257

SOUTH BERKSHIRE COUNTY, UPDATED VILLAGE CENTER HOME & OFFICEThis graciously restored vintage house has all the benefits of an ideal Sheffield setting with walkability to restaurants, Bushnell-Sage Library, Dewey Hall, post office, bank, and churches. With residential/commercial zoning, the house features an above-garage private large office/studio, a 1,000 sq. ft. outbuilding with plumbing and

David Taylor ELYSE HARNEY REAL ESTATE

86 Main St, Sheffield, MA 01257
/2
$680,000 Sold Jun 30, 2025

63 Glennanna Way, Sheffield, MA 01257
- 4 Beds
- 3.5 Baths
- 2,000 Sq Ft
- Built 1999
Last Sold Summary
- 2% Below List Price
- $340/SF
- 76 Days On Market
Current Estimated Value $722,801

Last Listing Agent Patrice Melluzzo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

63 Glennanna Way, Sheffield, MA 01257

/29
Est $581,814 Not Listed For Sale

24 Cactus St, Sheffield, MA 01257
- 3 Beds
- 2 Baths
- 1,494 Sq Ft
- Built 2002
24 Cactus St, Sheffield, MA 01257

Last Sold Summary
- 17% Above List Price
- $334/SF
- 16 Days On Market
Last Sold Price $499,000

Last Listing Agent Leslie Chesloff William Pitt

/29
$365,000
- 3 Beds
- 1.5 Baths
- 1,482 Sq Ft
153 E Main St, Ashley Falls, MA 01222

TITLE V PASSED. Mid-1960s ranch on a quiet street with nearly 1/2 acre! A perfect family home to settle down in Southern Berkshire County. Semi-finished basement is a huge bonus, plus garage and additional detached barn/workshop. Sunny, spacious and ripe with potential. Some thoughtful updates will be needed -- or move in today and make it yours!

John Segalla HOUSATONIC REAL ESTATE

153 E Main St, Ashley Falls, MA 01222
/33
$675,000 Sold May 16, 2025

1105 Boardman St, Sheffield, MA 01257
- 3 Beds
- 3.5 Baths
- 2,576 Sq Ft
- Built 2002
Last Sold Summary
- 7% Below List Price
- $262/SF
- 34 Days On Market
Current Estimated Value $710,173

Last Listing Agent William Morrow WILLIAM PITT SOTHEBY'S - GT BARRINGTON

1105 Boardman St, Sheffield, MA 01257

/4
Est $747,775 Not Listed For Sale

1609 County Rd, Great Barrington, MA 01230
- 4 Beds
- 2 Baths
- 1,792 Sq Ft
- Built 1991
1609 County Rd, Great Barrington, MA 01230

Last Sold Summary
- 36% Above List Price
- $307/SF
- 24 Days On Market
Last Sold Price $550,000

Last Listing Agent Selina Lamb BIRCH PROPERTIES

/2
$57,900 Pending
- Land
- 5.1 Acres
- $11,353 per Acre
0 Alum Hill Unit 73415610, Sheffield, MA 01257

OWNER FINANCING AVAILABLE! This 5.1-acre wooded parcel in peaceful Sheffield, MA offers the perfect setting for your Berkshires retreat or year-round home. Surrounded by natural beauty, you'll enjoy nearby attractions like Bartholomew’s Cobble, the Appalachian Trail, and the cultural gems of Great Barrington just minutes away. Sheffield is known for its small-town charm, farm-to-table dining, and

Derek Greene The Greene Realty Group

0 Alum Hill Unit 73415610, Sheffield, MA 01257
/13
$272,500 Sold Dec 05, 2025

412 Berkshire School Rd, Sheffield, MA 01257
- 3 Beds
- 1 Bath
- 900 Sq Ft
- Built 1995
Last Sold Summary
- 22% Below List Price
- $303/SF
- 66 Days On Market
Current Estimated Value $282,712

Last Listing Agent Patrice Melluzzo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

412 Berkshire School Rd, Sheffield, MA 01257

/18
Est $221,101 Not Listed For Sale

139 Silver St, Sheffield, MA 01257
- 5 Beds
- 1,656 Sq Ft
- Built 1910
139 Silver St, Sheffield, MA 01257

Last Sold Summary
- 39% Above List Price
- $96/SF
- 394 Days On Market
Last Sold Price $159,000

Last Listing Agent Cortney Dupont COHEN & WHITE ASSOCIATES

/24
$299,900
- 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
/30
$300,000 Sold Nov 07, 2025

179 S Main St, Sheffield, MA 01257
- 3 Beds
- 2.5 Baths
- 1,536 Sq Ft
- Built 1826
Last Sold Summary
- 24% Below List Price
- $195/SF
- 395 Days On Market
Current Estimated Value $354,977

Last Listing Agent Tony Segalla WILLIAM RAVEIS - BERKSHIRE

179 S Main St, Sheffield, MA 01257

/24
Est $492,377 Not Listed For Sale

301 Miller Ave, Sheffield, MA 01257
- 3 Beds
- 2 Baths
- 1,644 Sq Ft
- Built 1958
301 Miller Ave, Sheffield, MA 01257

Last Sold Summary
- 3% Below List Price
- $310/SF
- 101 Days On Market
Last Sold Price $510,000

Last Listing Agent Suzann Ward HOUSATONIC REAL ESTATE

/36
$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
/34
$680,000 Sold Oct 20, 2025

662 Foley Rd, Sheffield, MA 01257
- 4 Beds
- 2 Baths
- 2,310 Sq Ft
- Built 1992
Last Sold Summary
- 12% Below List Price
- $294/SF
- 69 Days On Market
Current Estimated Value $735,652

Last Listing Agent Claire Pollart WILLIAM RAVEIS - BERKSHIRE

662 Foley Rd, Sheffield, MA 01257

/19
Est $289,256 Not Listed For Sale

590 S Main St, Sheffield, MA 01257
- 2 Beds
- 1 Bath
- 1,160 Sq Ft
- Built 1945
590 S Main St, Sheffield, MA 01257

Last Sold Summary
- 29% Above List Price
- $194/SF
- 195 Days On Market
Last Sold Price $225,000

Last Listing Agent Dan Alden ALDEN COUNTRY REAL ESTATE SERVICES

/60
$1,250,000
- 3 Beds
- 2.5 Baths
- 2,204 Sq Ft
905 West Rd, Great Barrington, MA 01230

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

905 West Rd, Great Barrington, MA 01230
/9
$342,000 Sold Aug 01, 2025

0 S Main St, Sheffield, MA 01257
- Land
- 6.25 Acres
- $54,720 per Acre
Last Sold Summary
- 10% Below List Price
- 49 Days On Market
Last Listing Agent Grace Golden Equine Homes Real Estate, LLC

0 S Main St, Sheffield, MA 01257

/32
Est $433,503 Not Listed For Sale

222 Water Farm Rd, Sheffield, MA 01257
- 2 Beds
- 1.5 Baths
- 1,170 Sq Ft
- Built 1973
222 Water Farm Rd, Sheffield, MA 01257

Last Sold Summary
- 13% Above List Price
- $329/SF
- 63 Days On Market
Last Sold Price $385,000

Last Listing Agent Michael Harrigan BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

/21
$110,000
- Land
- 7.07 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, and/or build a viewing platform for regular visits, it has 7.2 acres (see map with) about 3.5+acres in a bog like 'state', the remainder being usable for building and walking along the bog's

Robin Leech Robinson Leech Real Estate

730 Clayton Rd, Sheffield, MA 01222
/34
$795,000 Sold Jun 09, 2025

371 Berkshire School Rd, Sheffield, MA 01257
- 3 Beds
- 2.5 Baths
- 2,633 Sq Ft
- Built 1949
Last Sold Summary
- $302/SF
- 12 Days On Market
Current Estimated Value $812,176

Last Listing Agent Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

371 Berkshire School Rd, Sheffield, MA 01257

/36
Est $566,282 Not Listed For Sale

78 Ashley Falls Rd, Sheffield, MA 01257
- 3 Beds
- 2 Baths
- 1,400 Sq Ft
- Built 2002
78 Ashley Falls Rd, Sheffield, MA 01257

Last Sold Summary
- 1% Above List Price
- $399/SF
- 144 Days On Market
Last Sold Price $559,000

Last Listing Agent Tony Segalla WILLIAM RAVEIS - BERKSHIRE

/38
$695,000 Pending
- 3 Beds
- 3 Baths
- 1,991 Sq Ft
483 Home Rd, Great Barrington, MA 01230

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 garage. Full basement could be completed as

Suzann Ward HOUSATONIC REAL ESTATE

483 Home Rd, Great Barrington, MA 01230

Showing Results 1 - 40, Page 1 of 18

Massachusetts Berkshire County Sheffield

Home Trends in Sheffield, MA

On average, homes in Sheffield, MA sell after 128 days on the market compared to the national average of 55 days. The median sale price for homes in Sheffield, MA over the last 12 months is $677,500, up 19% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$677,500

Median Single Family Sale Price

$677,500

Median Townhouse Sale Price

$649,000

Average Price Per Sq Ft

$309

Number of Homes for Sale

Last 12 months Home Sales

Months of Supply

2.60

Median List Price

$729,000

Median Change From 1st List Price

15%

Median Home Sale Price YoY Change

19%

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Sheffield, MA Homes

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Home Trends in Sheffield, MA

Housing Trends