29

Sheffield, MA Homes for Sale

Section Image
  • /40

    $1,275,000

    • 3 Beds
    • 3 Baths
    • 2,878 Sq Ft

    1166 Rannapo Rd, Sheffield, MA 01257

    It's no wonder this property is the home of Berkshire county's oldest elm tree! The abundant sunshine & quietude would make anybody want to set down roots. This light filled home has wood floors throughout the main level. Kitchen has granite counters, pantry & large island. As part of the open floor plan there is a dining room and living room that opens to an expansive deck. The great room

    Grace Golden Equine Homes Real Estate, LLC

    1166 Rannapo Rd, Sheffield, MA 01257
  • /58

    $715,000

    • 3 Beds
    • 3 Baths
    • 2,120 Sq Ft

    649 Hewins St, Sheffield, MA 01257

    This special property has been thoughtfully renovated to preserve its antique farmhouse charm. Set on an open 1-acre lot along a pastural country road and shaded by a stately maple tree, this home exudes that timeless vintage character that is so rare to find. Step through the rustic pine door onto the brick floor of the white washed pine-paneled mudroom. Upon entering the bright kitchen, you may

    Vashti Poor LANCE VERMEULEN RE, INC

    649 Hewins St, Sheffield, MA 01257
  • /59

    $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

    $1,095,000

    • 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
  • /53

    $725,000

    • 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

    64 Hewins 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
  • /52

    $998,000

    • 2 Beds
    • 3 Baths
    • 1,800 Sq Ft

    856 Barnum St, Sheffield, MA 01257

    Welcome to 856 Barnum, a stunning residence born from the creative vision of a talented photographer and acclaimed New York architect, Debora K. Reiser. What was once a modest Cape Cod has been transformed into a sophisticated modern masterpiece.The exterior showcases sleek lines and elegant copper details, with a striking turret adding depth to its profile. Upon entering, you are greeted by a

    Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

    856 Barnum St, Sheffield, MA 01257
  • /53

    $1,750,000

    • 4 Beds
    • 3.5 Baths
    • 4,853 Sq Ft

    360 Brush Hill Rd, Sheffield, MA 01257

    Tucked away in the woods with access to Three Mile Pond, this contemporary home will leave you longing to return. With views from most rooms, the thoughtfully designed floor plan leaves little to be desired. The main living spaces include an inviting living room with a stone fireplace that opens to a screened porch, a cozy den/library, and a spacious great room with soaring ceilings, a grand

    Tony Segalla LANCE VERMEULEN RE, INC

    360 Brush Hill Rd, Sheffield, MA 01257
  • /40

    $400,000

    • 5 Beds
    • 2 Baths
    • 2,485 Sq Ft

    254 Main St, Sheffield, MA 01257

    Welcome the historic Foxdale and the opportunity to own a piece of history that begins before the declaration of independence. This property originally was built in the 1750s. If a house with character is what you're looking for, look no further! In the heart of the village of Sheffield, you will find this property unlike any other. After its complete restoration by its visionary new owner this

    Cortney Dupont COHEN & WHITE ASSOCIATES

    254 Main St, Sheffield, MA 01257
  • /10

    $119,000

    • Land
    • 1.45 Acres
    • $82,069 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
  • /40

    $499,000

    • 6 Beds
    • 2.5 Baths
    • 2,994 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

    119 S Main St, Sheffield, MA 01257
  • /33

    $495,000

    • 2 Beds
    • 1 Bath
    • 1,700 Sq Ft

    1291 Ashley Falls Rd, Sheffield, MA 01222

    Nestled in the charming village of Ashley Falls, this cozy single-level home offers a perfect blend of comfort and scenic beauty. The open floor plan includes 2 bedrooms, 1 bath, an eat-in kitchen, and a spacious living room with a wood-burning fireplace, large picture windows, and direct access to a screened porch overlooking acres of picturesque farmland. Additional features include a slab

    Dan Alden ALDEN COUNTRY REAL ESTATE SERVICES

    1291 Ashley Falls Rd, Sheffield, MA 01222
  • /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
  • /20

    $549,000

    • 3 Beds
    • 3 Baths
    • 6,420 Sq Ft

    355 Clayton Rd, Sheffield, MA 01222

    Opportunities and Potential abound. Set back on 6+- acres in Rural Ashley Falls. Presently Greenwoods Church, can now be yours to live and work from. The large bright and open main room is 42' x 70' with a concrete floor and forced air heat. Create the space you've envisioned for yourself and your business, the ideas are endless from continuing a place of worship, a grand home, a car collectors

    Mark Rosengren LANCE VERMEULEN RE, INC

    355 Clayton Rd, Sheffield, MA 01222
  • /21

    $325,000

    • 4 Beds
    • 1 Bath
    • 1,704 Sq Ft

    1114 County Rd, Great Barrington, MA 01230

    1950's Cape on 7.5 acres along a country road. This 4 bedroom home has a main floor with nice size kitchen, dining room, living room with fireplace, 2 bedrooms and a full bath. Upstairs there are two more bedrooms and a small office and good attic storage. Screened in porch off the living room, wood floors and beautiful yard. Roof is old (estimate attached in docs), Title V failed and seller is

    Jen Harvey COMPASS MASSACHUSETTS , LLC GB

    1114 County Rd, Great Barrington, MA 01230
  • /11

    $795,000

    • Land
    • 18 Acres
    • $44,167 per Acre

    0 Bull Hill Rd, Sheffield, MA 01257

    Eighteen acres on the quitest 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.

    Martha Piper 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

    $369,000

    • 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

    $430,000

    • 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
  • /21

    $220,000

    • 2 Beds
    • 1 Bath
    • 1,096 Sq Ft

    339 Clayton Rd, Sheffield, MA 01222

    Fantastic Opportunity to own in well established South Berkshire neighborhood. This homes good bones and newer roof make it a perfect candidate for a fresh makeover. Level 1 acre lot and oversized 2 car garage !

    Eric Steuernagle FAIRGROUND REAL ESTATE, INC

    339 Clayton Rd, Sheffield, MA 01222
  • /41

    $499,000

    • 3 Beds
    • 2 Baths
    • 2,152 Sq Ft

    163 Main St, Sheffield, MA 01257

    Built in 1802, this delightful 3-bedroom home is full of original details and charm. The 1st floor features two parlors with a double-sided fireplace, built-in bookcases, and a bay window with window seat perfect for curling up with a good book by the fire. French doors lead to a large open dining room and kitchen with granite countertops and cherry cabinets. Just off the kitchen is a cozy den

    Vashti Poor LANCE VERMEULEN RE, INC

    163 Main St, Sheffield, MA 01257
  • /21

    $110,000

    • Land
    • 7 Acres
    • $15,559 per Acre

    730 Clayton Rd, Sheffield, MA 01222

    This property contains a wetland suggested by some to be an official BOG; full of a bog's normal wildlife depending on the season. All earlier permits for building have expired, so new ones are required before building, including location, building, septic, and well permits. The probable building zone is an area adjacent to the bog shoreline, estimated to be around 2.5 acres, or less, as shown on

    Robin Leech Robinson Leech Real Estate

    730 Clayton Rd, Sheffield, MA 01222
  • /5

    $297,000

    • Land
    • 36 Acres
    • $8,303 per Acre

    0 County Rd, Sheffield, MA 01257

    Sheffield Woodland with Potential Views - Located off Bucolic County Road, just minutes from Sheffield Center this lovely 35.77-acre wooded parcel has a substantial elevation of over 1000 ft. The property is currently wooded with multiple hardwoods perfect for timbering to clear a home site. The property with clearing has south and western exposure. The well-drained soil has been perc'd and will

    Elyse Morris ELYSE HARNEY REAL ESTATE

    0 County Rd, Sheffield, MA 01257
  • /39

    $1,495,000

    • 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
  • /2

    $249,000

    • 4 Beds
    • 1.5 Baths
    • 1,152 Sq Ft

    321 Salisbury Rd, Sheffield, MA 01257

    Attention investors! This property features a primary bedroom with a half bath, along with three additional bedrooms, offering plenty of living space. The combined two lots total 7.99 acres, providing ample room for expansion. Having been vacant for several years, this property presents a blank canvas, ready for someone with a vision to restore it to its former glory. Potential buyers should be

    Diane McDougald Berkshire Hathaway Home Service New England Properties

    321 Salisbury Rd, Sheffield, MA 01257
  • /24

    $339,000

    • 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
  • /68

    $4,290,000

    • 4 Beds
    • 4.5 Baths
    • 5,800 Sq Ft

    113 Brush Hill Rd, Great Barrington, MA 01230

    THE GOAT......This exceptional Berkshire minimalistic sensation has been architecturally designed to maximize the open floor plan concept while being mindful of private work/play spaces. A showpiece with 12+ acres of privacy surrounds you while the panoramic western views in every season bring you peace and calmness. The walls of glass integrate nature and the tranquil spellbinding views with

    Mary Jane White COHEN & WHITE ASSOCIATES

    113 Brush Hill Rd, Great Barrington, MA 01230
  • /45

    $299,000 Open Sat 11:30AM - 1:30PM

    • 2 Beds
    • 2 Baths
    • 1,659 Sq Ft

    52 Shunpike Rd, Southfield, MA 01259

    Attention investors!! Nestled on a peaceful 1-acre lot, this 2-bedroom, 2-bath Cape offers warmth, character, and SO MUCH OPPORTUNITY! A spacious kitchen with adjoining pantry and dining area provides plenty of room for gathering. The inviting living room features a chunky staircase, exposed beams and a brick hearth, perfect for a wood or pellet stove. The first floor includes a bedroom, laundry

    Chris LaPatin LAMACCHIA REALTY, INC

    52 Shunpike Rd, Southfield, MA 01259

Frequently Asked Questions About Sheffield

What is the average home price in Sheffield, MA?
Homes for sale in Sheffield, MA have an average home price of $925,282.
How many homes have sold over the last 12 months in Sheffield, MA?
22 homes have sold in Sheffield, MA over the last 12 months.
What are the most popular zip codes in Sheffield, MA?
The most popular zip codes in Sheffield, MA include 01230, 06098, 01223, 06790 and 12529.
How much do you need to make to afford a house in Sheffield?
The median home price in Sheffield is $779,000. If you put a 20% down payment of $155,800 and had a 30-year fixed mortgage with an interest rate of 6.83%, your estimated principal and interest payment would be $4,080 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $175K a year to afford the median home price in Sheffield.
How are the schools in Sheffield, MA?
Sheffield, MA has highly rated public and private schools. Some of the best schools in Sheffield based on Niche Grades are Berkshire School, New Marlborough Central School and North Canaan Elementary School. Browse all the schools in Sheffield, MA to learn more.

Home Trends in Sheffield, MA

Home Trends

Median Price (12 Mo)
$562,500
Median Single Family Price
$819,500
Average Price Per Sq Ft
$397
Number of Homes for Sale
10
Last 12 months Home Sales
22
Months of Supply
5.50
Median List Price
$779,000
Median Discount From 1st List Price
5%
Median Home Sale Price YoY Change
7%
How to Buy a Home How to Finance a Home How to Sell a Home