5-Bedroom Homes for Sale in Berkshire County MA

/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
/58
$1,395,000
- 6 Beds
- 3.5 Baths
- 3,905 Sq Ft
21 Stockbridge Rd, West Stockbridge, MA 01266

Tucked away on a private 2.35-acre knoll, this beautifully updated residence offers a rare blend of antique charm and modern ease in one of the Berkshires' most sought-after villages. With six generously sized bedrooms, a chef's kitchen designed for entertaining, and multiple inviting living spaces with fireplaces, the home is ideal for gatherings or quiet retreats alike. A stunning contemporary

Dan Alden

ALDEN COUNTRY REAL ESTATE SERVICES

(413) 675-5317

21 Stockbridge Rd, West Stockbridge, MA 01266
/16
$470,000
- 8 Beds
- 6 Baths
- 8,543 Sq Ft
153 First St, Pittsfield, MA 01201

Looking to add a well-performing asset that provides you with income from day one? This six-family investment property offers investors immediate cash flow and upside potential... sitting at a 11 cap rate, this property offers a strong return on investment with room to grow based on some under market rents! This property offers a range of studio to 3-bedroom units and Off street parking.

Corey Bishop

BISHOP WEST REAL ESTATE

(413) 728-1773

153 First St, Pittsfield, MA 01201
/57
$3,250,000
- 6 Beds
- 5.5 Baths
- 4,681 Sq Ft
1333 Norfolk Rd, Southfield, MA 01259

Set on 11 enchanting acres in the pastoral town of New Marlborough, Massachusetts, this exceptional Berkshires estate offers a rare convergence of architectural refinement, natural splendor, and modern luxury. Designed by an architect and originally built in 1984, the main house, guest house, and pool house were all fully renovated in early 2025 to create a cohesive, contemporary compound with

Selina Lamb

BIRCH PROPERTIES

(413) 327-9228

1333 Norfolk Rd, Southfield, MA 01259
/53
$2,649,000
- 6 Beds
- 6.5 Baths
- 4,289 Sq Ft
250 West St, Lenox, MA 01240

Just seconds not minutes from the main gates of Tanglewood, this stunning contemporary estate is tucked into a sunlit site surrounded by woodland, offering a rare blend of proximity and seclusion. In a region renowned for its natural beauty, it's almost unheard of to find a home this close to the cultural heart of the Berkshires that also feels so entirely removed.Perfectly positioned for

Selina Lamb

BIRCH PROPERTIES

(413) 423-1264

250 West St, Lenox, MA 01240
/32
$149,900
- 5 Beds
- 3 Baths
- 2,250 Sq Ft
136 Church St Unit 142, Cheshire, MA 01225

Situated in the heart of the quaint town of Cheshire, this 3 family offers potential for the new owner as an investment or owner occupied. First floor has 2 bedrooms, primary is large, living room and kitchen are also spacious and kitchen offers pantry w/ potential laundry hook ups. Upstairs back unit is 2 bedroom, Upstairs front unit is 1 bedrooms & currently vacant. Long term tenants &

Nadine Hiser

KRG - Key Realty Group

(413) 475-9494

136 Church St Unit 142, Cheshire, MA 01225
/10
$165,000
- 6 Beds
- 3 Baths
- 1,646 Sq Ft
10 Miner St, North Adams, MA 01247

Two Family home, with one unit vacant and the other rented, providing immediate cash flow. Just minutes from downtown, MCLA, and local shopping, the location offers unbeatable convenience.The first-floor unit features two bedrooms, one bath, and an enclosed porch--perfect for morning coffee or added storage. The spacious second unit spans two levels with four bedrooms and two full baths, ideal

Corey Bishop

BISHOP WEST REAL ESTATE

(413) 298-6352

10 Miner St, North Adams, MA 01247
/69
$5,900,000
- 11 Beds
- 10 Baths
- 9,748 Sq Ft
25 W Sheffield Rd, Great Barrington, MA 01230

Tullar Farm represents a rare opportunity to own a piece of history where timeless elegance meets modern comfort amidst the serenity of South Egremont's charming landscape. With its rich architectural heritage, generations of proud stewardship, and unrivaled natural beauty, this distinguished estate stands as a testament to the enduring legacy of its past and the promise of future for generations

Lauren Molk ELYSE HARNEY REAL ESTATE

25 W Sheffield Rd, Great Barrington, MA 01230
/60
$4,950,000
- 7 Beds
- 8.5 Baths
- 7,073 Sq Ft
1 Pinecroft Dr, Lenox, MA 01240

Gated Berkshire Stone Estate in exclusive Pinecroft compound with Canyon Ranch Living and its 125 maintenance-free acres. Optional membership. Turnkey home features elevator, 300-year-old reclaimed timber floors and large gourmet kitchen. Great room boasts floor-to-ceiling stone fireplace, wet bar, Nano doors to screened lanai. Two primary en suite bedrooms with cedar closets. Lower level: gym,

Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

1 Pinecroft Dr, Lenox, MA 01240
/77
$5,800,000
- 5 Beds
- 5.5 Baths
- 5,002 Sq Ft
764 E Hill Rd, New Marlborough, MA 01230

High on a hilltop in the Southern Berkshires stands East Hill Farm. Pristine forest, spring-fed pond, glorious barn, pastures, gardens, pool, and tennis court. The centerpiece: a 1798 Federal home with Georgian elements of classic New England architecture.Manor House5 Bedrooms, 5 1/2 Baths 5,000 sfReady for private living, entertaining, horses, farming, a bespoke destination, or simply:

Chapin Fish WILLIAM PITT SOTHEBY'S - GT BARRINGTON

764 E Hill Rd, New Marlborough, MA 01230
/82
$2,550,000
- 6 Beds
- 6.5 Baths
- 7,143 Sq Ft
13 Taconic Ave, Lenox, MA 01240

An Unrivaled 8-Acre Sanctuary of Beauty, Privacy & SophisticationNestled in the cultural heart of the Berkshires, just steps from downtown Lenox, this extraordinary property offers a rare and coveted blend of seclusion and sophistication set on an unheard-of 8 acres of wooded, professionally designed, and maturely landscaped grounds.Inside, the home has been completely reimagined, with every

Maggie Gavin WILLIAM PITT SOTHEBY'S - LENOX

13 Taconic Ave, Lenox, MA 01240
/69
$565,900
- 8 Beds
- 3 Baths
- 4,034 Sq Ft
144 Brombach St, Pittsfield, MA 01201

Beautiful, spacious 8 bedroom, 3 updated bath, 4000+sf home, custom built and nestled between two lakes with incredible views in the heart of the picturesque Berkshire Mountains! Walk to Onota Lake in approximately 9 minutes and enjoy a 5 minute drive to Pontoosuc Lake both suitable for kayaking, fishing, swimming, picnicking and more. Enjoy the convenience of 2 laundry rooms and two updated

Darcy Reid MOCKINGBIRD REAL ESTATE

144 Brombach St, Pittsfield, MA 01201
/47
$1,790,000
- 6 Beds
- 6.5 Baths
- 5,115 Sq Ft
76 Lenox Rd, West Stockbridge, MA 01266

New World charm meets timeless elegance in this thoughtfully designed French Country-style home, perfectly sited to take in stunning westerly mountain and sunset views. Privately nestled on 3.76 manageable acres, it's just minutes to Tanglewood, downtown Lenox, and West Stockbridge.Designed with both comfort and hospitality in mind, the home offers a flexible layout with six bedrooms and seven

Maggie Gavin WILLIAM PITT SOTHEBY'S - LENOX

76 Lenox Rd, West Stockbridge, MA 01266
/47
$1,650,000
- 5 Beds
- 3 Baths
- 2,808 Sq Ft
353 State Rd, Great Barrington, MA 01230

The Woodlands, A RARE OPPORTUNITY TO OWN YOUR OWN 74-ACRE PRIVATE SANCTUARY IN THE HEART OF GREAT BARRINGTON.This property abuts the Thomas & Palmer Brook preserve on three sides, is a two-minute drive to Ski Butternut and five minutes to dining and shopping in downtown Great Barrington. A picturesque pond flows into a babbling brook right outside of the large cathedral-ceiling primary suite's

Timothy Lovett COMPASS MASSACHUSETTS , LLC GB

353 State Rd, Great Barrington, MA 01230
/45
$3,900,000
- 10 Beds
- 5.5 Baths
- 7,864 Sq Ft
535 Main Rd, Monterey, MA 01245

Welcome home to NEWGRANGE. 1920's era Manor House with lake frontage on Lake Garfield. Over 10,000 square feet of living on 7.7 Acres. Complete the restoration and enjoy original Stone Fireplaces, comfortable Living spaces, formal Dining and 10 Bedrooms. Write that novel in the paneled Office, Library or Sunroom, create delicacies in the Country Kitchen, or shoot a round of pool in the Billiard

Steven Weisz WILLIAM PITT SOTHEBY'S - GT BARRINGTON

535 Main Rd, Monterey, MA 01245
/51
$1,998,000
- 12 Beds
- 10.5 Baths
- 7,979 Sq Ft
7 Hubbard St, Lenox, MA 01240

Welcome to The Dewey, a rare opportunity to own one of Lenox's most iconic residences. Built in 1767, this remarkable property--known as the Israel Dewey House--stands as a testament to early American architecture and timeless elegance. Set in the heart of the Berkshires, It beautifully bridges centuries of history with the comforts of today.The Main HouseSpanning 6,839 square feet across three

Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

7 Hubbard St, Lenox, MA 01240
/85
$3,995,000
- 5 Beds
- 6.5 Baths
- 6,915 Sq Ft
662 Brewer Hill Rd, New Marlborough, MA 01230

Iconic only begins to describe this rare union of sophistication & natural splendor. Spanning 40+ secluded acres of rolling meadows, forested trails, & sweeping mountain views, this remarkable estate has welcomed world-renowned artists & hosted unforgettable gatherings, from summer soirees to intimate retreats.At its heart is the Great House--a 6,000 sq. ft. architectural masterpiece by renowned

Claire Pollart LANCE VERMEULEN RE, INC

662 Brewer Hill Rd, New Marlborough, MA 01230
/77
$4,500,000
- 5 Beds
- 5.5 Baths
- 4,027 Sq Ft
19 Roberts Rd, Sandisfield, MA 01255

Introducing  FREE QUARTER FARMNearly 1,500 Acres | Sandisfield, the Southern Berkshires | $4,500,000Miles of private trails for hiking, hunting, fishing, horseback riding - your own wilderness preserve134+ acres not in conservation with 1,489 feet of road frontage - craft your legacy5BR/5BA timeless home built for this wildly beautiful placeStand between your home, overlooking your private

Chapin Fish WILLIAM PITT SOTHEBY'S - GT BARRINGTON

19 Roberts Rd, Sandisfield, MA 01255
/59
$1,850,000
- 6 Beds
- 5.5 Baths
- 4,952 Sq Ft
1 Devon Rd, Stockbridge, MA 01262

Located in Stockbridge, this historic General Williams House (circa 1795) has been restored and updated. Featuring 6 bedrooms, 5.5 bathrooms, 6 beautiful wood burning fireplaces, large dining and living spaces and 2 kitchens. The ''Ice House'' features its own kitchen and bath, for family gatherings or as Artist Studio. A sparkling in-ground pool for your summer pleasure. All this and more

George Cain WILLIAM PITT SOTHEBY'S - GT BARRINGTON

1 Devon Rd, Stockbridge, MA 01262
/57
$1,595,000
- 5 Beds
- 3 Baths
- 3,043 Sq Ft
593 Lakeway Dr, Pittsfield, MA 01201

This exceptional lakefront retreat offers it all! Nearly 100 feet of eastern shoreline, private dock, and shimmering in-ground pool. Inside, a beautiful kitchen flows into living spaces with lake views from nearly every room. The first floor also features a spacious living room, dining area, play/relaxation room, office with custom desk/Murphy bed, and full bath. Upstairs, the luxurious primary

Victoria Standring LAMACCHIA REALTY, INC

593 Lakeway Dr, Pittsfield, MA 01201
/59
$1,500,000
- 5 Beds
- 2.5 Baths
- 3,000 Sq Ft
194 Sandisfield Rd, Sandisfield, MA 01255

A master stoneworker and his family spent a year walking 11 acres to find the one perfect spot. Then they built their dream around it - every fieldstone placed by hand from rocks cleared by 150 years of farming, hand-hewn cherry beams harvested from the land soaring above the stone-clad Great room. This rustic modern farmhouse embodies the truth that in simplicity lives beauty. The timber-framed

Chapin Fish WILLIAM PITT SOTHEBY'S - GT BARRINGTON

194 Sandisfield Rd, Sandisfield, MA 01255
/54
$2,500,000
- 5 Beds
- 4.5 Baths
- 5,233 Sq Ft
55 Main St, Stockbridge, MA 01262

Historic Elegance Reimagined!Wellness-forward design. Artisan craftsmanship. In-town privacy.A Kitchen Rebuilt from the Ground Up: At the heart of the home, a brand-new chef's kitchen makes a bold, refined statement with honed dark gray granite countertops, crisp white shaker cabinetry, and minimalist matte black fixtures. Oversized divided-light windows flood the space with natural light, while

Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

55 Main St, Stockbridge, MA 01262
/20
$3,799,000
- 15 Beds
- 15 Baths
- 11,945 Sq Ft
615 Laurel St, Lee, MA 01238

The Lakehouse enjoys a spectacular setting on a westerly facing cliff overlooking pristine Laurel Lake in the heart of The Berkshires. The Lakehouse is a classic three-story, shingle style mansion with 530' of lake frontage including its own dock. Built in 1903, the architecture denotes the unpretentious, timeless elegance of a turn-of-the-century lakeside cottage. There are 15 bedrooms and

Pamela J Long EAST COAST INN BROKERS

615 Laurel St, Lee, MA 01238
/64
$1,900,000
- 5 Beds
- 4.5 Baths
- 4,500 Sq Ft
355 Adsit Crosby Rd, New Marlborough, MA 01230

Stunning contemporary nestled in tranquility. The main level boasts a gracious great room with cathedral ceilings, fireplace and walls of windows that wash the common spaces with natural light and bring nature in. Gourmet chefs kitchen with ample storage and dining room with direct access to the oversized porch that features a gas stove for the chillier days. First floor primary en suite with

Cortney Dupont COHEN & WHITE ASSOCIATES

355 Adsit Crosby Rd, New Marlborough, MA 01230
/44
$1,800,000
- 5 Beds
- 3.5 Baths
- 3,768 Sq Ft
307 Stanley Rd, Otis, MA 01253

Welcome to this Berkshire Waterfront Paradise! With amazing lake and sunset views this home has it all. Five bedrooms all with lake views. Your family and friends will find the total relaxation the Berkshires can offer. Whether it's a swim, paddle, fishing or a water ski on the lake it's all just steps out the door. The beautiful stone fireplace sores to compliment this open space and provides a

David St. Laurent BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS OTIS

307 Stanley Rd, Otis, MA 01253
/50
$1,950,000
- 5 Beds
- 4.5 Baths
- 4,301 Sq Ft
20 E Dugway Rd, Lenox, MA 01240

Lenox Estate on 36 Acres - Two HomesJust one mile from the center of Lenox, this unique estate offers exceptional space and versatility with two separate residences. The main home boasts 4,100 square feet with five bedrooms and three and a half bathrooms--perfect for spacious living or entertaining. The second home is a charming 1,200-square-foot residence with two bedrooms and two full baths,

Tanya Shepardson LAMACCHIA REALTY, INC

20 E Dugway Rd, Lenox, MA 01240
/50
$1,825,000
- 5 Beds
- 5.5 Baths
- 3,225 Sq Ft
5 Easland Rd, West Stockbridge, MA 01266

A Home Designed for Living and RetreatNestled at the base of Tom Ball Mountain on over 10 private acres, 5 Easland Road is a custom-designed contemporary sanctuary where nature, luxury, and thoughtful craftsmanship come together in perfect harmony.This 5-bedroom, 5.5-bath home features soaring vaulted ceilings, dramatic walls of glass, and gleaming hardwood floors throughout. Each of the three

Maggie Merelle WILLIAM PITT SOTHEBY'S - GT BARRINGTON

5 Easland Rd, West Stockbridge, MA 01266
/33
$1,500,000
- 7 Beds
- 7.5 Baths
- 4,000 Sq Ft
802 State Rd, Richmond, MA 01254

Nestled in the heart of the Berkshires, this historic Richmond compound presents a rare blend of colonial charm and modern equestrian excellence. Spanning 11+ bucolic acres with sweeping pastoral views, the legendary c1776 estate boasts a meticulously maintained main residence, three enchanting cottages, and the potential to include the region's premier full-service equestrian facility (see

Diana Bisselle William Pitt Sotheby's Int'l

802 State Rd, Richmond, MA 01254
/16
$1,800,000
- 40 Beds
- 20 Baths
- 30,000 Sq Ft
15 East St, Stockbridge, MA 01262

Located in a Sngle Family zoned area on a desirablle, private parcel consisting of nine total buildings with an in-ground pool amongst other amenities. Property is available for sale, lease or equity investment by new partners. This is an amazing property on the border of Stockbridge and Lenox with close proximity to Albany / Hartford / I-91. Many opportunities for possible hotel, B&B, family

Tim Damon Mercury Real Estate

15 East St, Stockbridge, MA 01262
/40
$1,590,000
- 11 Beds
- 12.5 Baths
- 8,134 Sq Ft
518 Main St, Great Barrington, MA 01230

The iconic Wainwright Inn, built in 1766, is ideally located on Main Street in Great Barrington, the largest town & hub of the famous Berkshires vacation destination in Western Massachusetts. The Inn consists of a main house with 9 guest suites & a spacious owner's suite, & a carriage house with an apartment & two additional guest suites. In pristine condition, the current owners have improved

Tanya LeRose THE KINDERHOOK GROUP - PITTSFIELD

518 Main St, Great Barrington, MA 01230
/43
$1,890,000
- 5 Beds
- 4.5 Baths
- 6,000 Sq Ft
248 East Rd, West Stockbridge, MA 01266

A luxurious home on one of the most scenic roads in The Berkshires, surrounded by 15 pastoral acres, with picturesque mountain views. Enter a sun-drenched living room with a soaring cathedral ceiling and an elegant fireplace centerpiece. Enjoy an expansive 3-season porch, with panoramic windows and classic mahogany floors. A recently updated eat-in kitchen features Sub Zero appliances and a

Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

248 East Rd, West Stockbridge, MA 01266
/41
$1,800,000
- 22 Beds
- 21 Baths
- 9,018 Sq Ft
885 Washington Mountain Rd, Washington, MA 01223

The Possibilities are endless! Family Compound & Retreat ! Hotel, Wedding Venue, Campgrounds, Cross Country Skiing Trails or Family Compound, bring your imagination and bring Buck Steep Manor back to Life! Five Buildings and many Cabins amid this 350-acre Estate. The Manor House 25 rooms the Lodge 19 rooms the Dutch Colonial Barn 5 rooms the Cottage 10 rooms The Antique Carriage Barn Hall 99pl

Joy Salvini RE/MAX Compass

885 Washington Mountain Rd, Washington, MA 01223
/41
$1,450,000 New Construction
- 5 Beds
- 3.5 Baths
- 3,978 Sq Ft
37 Old Farm Ln, Pittsfield, MA 01201

LOOK AT THIS! Did you know you may qualify for construction loans with VA, FHA, or even with less than 20% down? Your dream home is just a build away! Imagine living in a modern oasis surrounded by nature — where space, comfort, and serenity come together in perfect harmony. This TO BE BUILT home at 37 Old Farm Ln offers nearly 4,000 sqft of luxurious living with 5 bedrooms, 4.5 baths, a sunlit

Mg Group Century 21 North East

37 Old Farm Ln, Pittsfield, MA 01201
/35
$149,000
- 5 Beds
- 2 Baths
- 2,444 Sq Ft
98-100 Columbia St, Adams, MA 01220

Opportunity Knocks! Duplex in the Heart of Admas. This true duplex offers 2,400 sq. ft. with separate utilities, updated windows, and vinyl siding. Each side has its own parking plus a large fenced backyard with a swing set--perfect for families, pets, and entertaining. Centrally located, it's within walking distance to shopping, dining, and local amenities. With solid bones, This home is ideal

Christine Girard STEEPLEVIEW REALTY - N. ADAMS

98-100 Columbia St, Adams, MA 01220
/20
$399,900
- 5 Beds
- 4 Baths
- 3,331 Sq Ft
31 Dover St, North Adams, MA 01247

Stately Victorian with good iIncome Potential:Step into this lovely Victorian, thoughtfully converted into four charming units, perfect for owner occupancy (first floor offers 6 rooms!) or a solid investment opportunity. This property boasts numerous updates, including modern heating, updated electrical, newer windows, fresh paint and more. Centrally located, just a short walk to MCLA, MASS

Pauline Green STEEPLEVIEW REALTY - ADAMS BRANCH

31 Dover St, North Adams, MA 01247
/36
$319,900
- 5 Beds
- 3 Baths
- 2,864 Sq Ft
380 Union St, North Adams, MA 01247

Turnkey three-family investment opportunity in North Adams with strong rental income potential. Close to downtown, MASS MoCA, and local schools, this property benefits from consistent rental demand. Two units offer 2 bedrooms and 1 bathroom and the lower unit features 1 bedroom and 1 bathroom. Each unit also includes its own enclosed porch and off-street parking. Recently updated with a new roof,

Cory Evangelisto NOCHER REALTY

380 Union St, North Adams, MA 01247
/42
$175,000
- 5 Beds
- 2 Baths
- 1,700 Sq Ft
297 Walnut St, North Adams, MA 01247

Welcome to 297 Walnut st in the vibrant city of North Adams! This property features two separate units: a fully renovated 2-bedroom, 1-bathroom apartment on the first floor currently rented for $1,500 per month, with tenants responsible for heat and electricity. The second-floor unit, a 3-bedroom, 1-bathroom, is vacant and in need of renovation, with a potential rent of $1,700 per month once

Monette Valliere Keller Williams Elite

297 Walnut St, North Adams, MA 01247
/18
$319,900
- 5 Beds
- 2.5 Baths
- 2,283 Sq Ft
667 & 669 E Main St, North Adams, MA 01247

**OPEN HOUSE SAT 9/6 12-2PM** Rare opportunity to purchase two homes side by side! Family owned, these properties are being offered together as a package on 1.43 acres both on the same deed. The sale includes both homes plus a spacious 4-car garage and plenty of off-street parking. Perfect for a family compound, rental portfolio, or multi-home investment.

Kyle Crocker eXp REALTY

667 & 669 E Main St, North Adams, MA 01247
/5
$245,900
- 6 Beds
- 2 Baths
- 2,564 Sq Ft
5 Richmond St, Adams, MA 01220

Spacious apartments with 3 bedrooms and a separate laundry in each unit. Updated kitchens. Porches with a view of MT, Greylock. Close to Ashuwilticook walking/biking trail .Walk to amenities. Updated heating systems. The Cupola offers a beautiful view of Mt.Greylock and Adams. It is roomy enough to be an office, an Artist's studio or just a relaxing haven away from the second floor apartment.

Sandra Sorel Coldwell Banker Realty - Western MA

5 Richmond St, Adams, MA 01220
/36
$289,900
- 5 Beds
- 2 Baths
- 1,841 Sq Ft
137 Bracewell Ave, North Adams, MA 01247

Discover this beautifully renovated modern Victorian duplex in the heart of downtown North Adams--just steps from Mass MoCA, restaurants, shops, and the amenities this vibrant arts community has to offer. This turnkey property is perfect for live and work from home, occupy one unit while renting the other, or use both as income-producing rentals. Upstairs Unit: 3 bedrooms (or 2 plus an office), 1

Pam Tworig BISHOP WEST REAL ESTATE

137 Bracewell Ave, North Adams, MA 01247

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