Vintage homes for sale & real estate in Berkshire County, MA

312 homes

Sort:

Recommended

ABOUT THIS HOME
Vintage Home for sale in Berkshire County, MA:
Cozy home with a wood stove for the perfect winter retreat, close to snowmobile trails, and 30-40 minutes from fabulous restaurants, 3 ski areas and land for hunting, only a few miles to 3 beautiful lakes, Plunkett, Ashmere and Garnett. (Garnett is within walking distance with private beach). Swimming, kayaking, canoeing and fishing with ice fishing in the season. Almost 5 acres of the most peaceful, serene and nature filled setting. Wildlife. Make this your primary residence, second residence or an Air BnB. 10 cords of log length seasoned wood to be left for buyer. Updated bathroom, 2-year new deck with sliders from kitchen. This can be your oasis. Beautiful landscaping with lilies and wil

$259,500

2 beds1 bath825 sq ft

9 Greylock Cir, Peru, MA 01235

2 year new deck • Raised garden beds • Fire pit

ABOUT THIS HOME
Vintage Home for sale in Berkshire County, MA:
Welcome to 7 Park Street a sun-filled, classic New England home tucked on a quiet dead-end lane right in the heart of Stockbridge. With 2 bedrooms, 1 bath, and 1,300 sq ft, this 1900 charmer blends historic warmth with thoughtful updates: wide rooms washed in natural light, an inviting screened porch for morning coffee, and an easy, intuitive layout that lives larger than its footprint. The setting is exceptional, stroll just minutes to the Red Lion Inn, cafés, shops, and the library; at the end of the street, pick up beloved local trails toward Laura's Tower for quick nature escapes. A manageable 6,970 sq ft lot keeps weekends free for play, gardening, or launching out to the Berksh

$549,000

2 beds1 bath1,300 sq ft

7 Park St, Stockbridge, MA 01262

Manageable lot • Local trails • Quiet dead-end lane

ABOUT THIS HOME
Vintage Home for sale in Berkshire County, MA:
Fantastic income-generating opportunity! This fully rented 3-family property features two spacious 3-bedroom, 1-bath units on the 2nd and 3rd floors, along with a beautifully renovated studio on the 1st floor. Each unit is separately metered, and tenants pay all utilities except water, making this a low-maintenance investment. The property also includes a large unfinished attic offering approximately 1,200 sq ft of additional potential — perfect for creating more living space or a private tenant retreat. With minimal exterior maintenance and no yard to care for, this property offers easy ownership and steady cash flow. Don’t miss this turnkey investment in the heart of North Ada

$250,000

6 beds3 baths2,664 sq ft

86 W Main St, North Adams, MA 01247

Turnkey investment • Renovated studio • 2,664 sq ft lot

ABOUT THIS HOME
Vintage Home for sale in Berkshire County, MA:
Easy living Ranch home on beautiful Onota Lake. Fantastic views of the Lake and Distant Berkshire Hills. Enjoy westerly sunset views from your expansive, manicured lawn and almost every room in the house. A quiet setting with comparable homes and easy access to all the Berkshires has to offer. Needs a little TLC, but well worth it for this sought after location and lifestyle. Hardwood floors refinished and interior recently painted.

$1,395,000

3 beds2 baths1,728 sq ft

61 Tor Court Ct, Pittsfield, MA 01201

Onota lake • 1.3 acre lot • 2 garage spots

ABOUT THIS HOME
Vintage Home for sale in Berkshire County, MA:
You'll feel right at home in this charming Richmond farmhouse, just minutes from West Stockbridge center and close to everything the Berkshires has to offer. Set on two beautiful, private acres in the historic Richmond Furnace district, this three-bedroom house blends New England charm with modern amenities, including energy-efficient solar panels, newer appliances, and Buderus boiler. The main level offers a smooth flow, featuring a spacious kitchen, bright sitting room with sliding doors to the deck, an inviting living room with fireplace, and an enclosed porch/mudroom accessible from the driveway. A full bath and first-floor laundry add practical convenience. Upstairs, three cozy bedroom

$389,000

3 beds1 bath1,413 sq ft

2801 State Rd, Richmond, MA 01254

Buderus boiler • Newer appliances • Spacious kitchen

Property at 108 Church St, Cheshire, MA 01225, 4 beds, 2 baths

$159,000

4 beds2 baths1,850 sq ft

108 Church St, Cheshire, MA 01225

Property at 8 Webster Rd, Tyringham, MA 01264, 7 beds, 6.5 baths

$4,600,000

7 beds6.5 baths5,885 sq ft

8 Webster Rd, Tyringham, MA 01264

Property at 191 Fort Hill Ave, Pittsfield, MA 01201, 3 beds, 1 bath

$495,000

3 beds1 bath1,998 sq ft

191 Fort Hill Ave, Pittsfield, MA 01201

Property at 30 Walker St, Lenox, MA 01240, 4 beds, 2 baths

$599,000

4 beds2 baths2,170 sq ft

30 Walker St, Lenox, MA 01240

Property at 25 Ashley St, Pittsfield, MA 01201, 4 beds, 2 baths

$204,900

4 beds2 baths1,496 sq ft

25 Ashley St, Pittsfield, MA 01201

Property at 17 Phelps Ave, North Adams, MA 01247, 2 beds, 1.5 baths

$234,900

2 beds1.5 baths1,064 sq ft

17 Phelps Ave, North Adams, MA 01247

Property at 20 Greenway St, Pittsfield, MA 01201, 3 beds, 1.5 baths

$289,900

3 beds1.5 baths1,320 sq ft

20 Greenway St, Pittsfield, MA 01201

Property at 78 State Rd, Great Barrington, MA 01230, 3 beds, 3.5 baths

$725,000

3 beds3.5 baths2,560 sq ft

78 State Rd, Great Barrington, MA 01230

Property at 36 Beacon Ave, Pittsfield, MA 01201, 1 bed, 1 bath

$124,900

1 bed1 bath680 sq ft

36 Beacon Ave, Pittsfield, MA 01201

Property at 30 Cove Ln, Hinsdale, MA 01235, 2 beds, 1 bath

$699,000

2 beds1 bath1,001 sq ft

30 Cove Ln, Hinsdale, MA 01235

Property at 910 North Hoosac Rd, Williamstown, MA 01267, 3 beds, 1 bath

$395,000

3 beds1 bath1,052 sq ft

910 North Hoosac Rd, Williamstown, MA 01267

Property at 74 Washington Ave, North Adams, MA 01247, 4 beds, 3 baths

$425,000

4 beds3 baths2,320 sq ft

74 Washington Ave, North Adams, MA 01247

Property at 95 Water Farm Rd, Sheffield, MA 01257, 4 beds, 2 baths

$495,000

4 beds2 baths1,531 sq ft

95 Water Farm Rd, Sheffield, MA 01257

Property at 33 Adam St, Pittsfield, MA 01201, 4 beds, 2 baths

$194,900

4 beds2 baths2,242 sq ft

33 Adam St, Pittsfield, MA 01201

Property at 399 State Rd, Richmond, MA 01254, 3 beds, 1.5 baths

$495,000

3 beds1.5 baths1,732 sq ft

399 State Rd, Richmond, MA 01254

Property at 13 Goodrich St, Pittsfield, MA 01201, 2 beds, 2 baths

$249,900

2 beds2 baths1,560 sq ft

13 Goodrich St, Pittsfield, MA 01201

Property at 1 Bulkley St, Williamstown, MA 01267, 3 beds, 3 baths

$629,000

3 beds3 baths1,779 sq ft

1 Bulkley St, Williamstown, MA 01267

Property at 33 Hudson St, North Adams, MA 01247, 4 beds, 1.5 baths

$259,000

4 beds1.5 baths2,343 sq ft

33 Hudson St, North Adams, MA 01247

Property at 381 Williams St, Pittsfield, MA 01201, 3 beds, 2.5 baths

$475,000

3 beds2.5 baths2,084 sq ft

381 Williams St, Pittsfield, MA 01201

Property at 106 Sampson Pkwy, Pittsfield, MA 01201, 3 beds, 1.5 baths

$369,000

3 beds1.5 baths1,561 sq ft

106 Sampson Pkwy, Pittsfield, MA 01201

Property at 15 W Stockbridge Rd, Stockbridge, MA 01262, 4 beds, 3 baths

$550,000

4 beds3 baths2,600 sq ft

15 W Stockbridge Rd, Stockbridge, MA 01262

Property at 65 Crofut St, Pittsfield, MA 01201, 5 beds, 4.5 baths

$1,350,000

5 beds4.5 baths4,948 sq ft

65 Crofut St, Pittsfield, MA 01201

Property at 122 Allengate Ave, Pittsfield, MA 01201, 2 beds, 1 bath

$265,000

2 beds1 bath974 sq ft

122 Allengate Ave, Pittsfield, MA 01201

Property at 48 Curtis, Hinsdale, MA 01235, 4 beds, 2 baths

$439,900

4 beds2 baths1,360 sq ft

48 Curtis, Hinsdale, MA 01235

Property at 194 Bartlett Ave, Pittsfield, MA 01201, 4 beds, 3 baths

$469,000

4 beds3 baths2,466 sq ft

194 Bartlett Ave, Pittsfield, MA 01201

Property at 66 Holmes Rd, Pittsfield, MA 01201, 3 beds, 1 bath

$239,900

3 beds1 bath1,257 sq ft

66 Holmes Rd, Pittsfield, MA 01201

Property at 1600 Pleasant St, Lee, MA 01238, 2 beds, 1 bath

$349,900

2 beds1 bath1,570 sq ft

1600 Pleasant St, Lee, MA 01238

Property at 156 Elizabeth St, Pittsfield, MA 01201, 3 beds, 2 baths

$229,900

3 beds2 baths1,454 sq ft

156 Elizabeth St, Pittsfield, MA 01201

Property at 5 Crofut St, Pittsfield, MA 01201, 5 beds, 3.5 baths

$889,900

5 beds3.5 baths3,370 sq ft

5 Crofut St, Pittsfield, MA 01201

Property at 1698 Clayton Mill River Rd, Southfield, MA 01259, 3 beds, 1 bath

$330,000

3 beds1 bath1,530 sq ft

1698 Clayton Mill River Rd, Southfield, MA 01259

Property at 53 Depot St, Cheshire, MA 01225, 3 beds, 2 baths

$399,900

3 beds2 baths1,756 sq ft

53 Depot St, Cheshire, MA 01225

Property at 792 Middle Rd, Clarksburg, MA 01247, 4 beds, 2 baths

$425,000

4 beds2 baths1,740 sq ft

792 Middle Rd, Clarksburg, MA 01247

Property at 190 Willow St, Lee, MA 01238, 3 beds, 3 baths

$499,000

3 beds3 baths1,716 sq ft

190 Willow St, Lee, MA 01238

Property at 40 Roland St, Pittsfield, MA 01201, 3 beds, 1 bath

$209,900

3 beds1 bath1,486 sq ft

40 Roland St, Pittsfield, MA 01201

Property at 220 N Plain Rd, Great Barrington, MA 01230, 3 beds, 2.5 baths

$499,000

3 beds2.5 baths1,922 sq ft

220 N Plain Rd, Great Barrington, MA 01230

Property at 17 Kittredge Rd, Pittsfield, MA 01201, 4 beds, 2.5 baths

$450,000

4 beds2.5 baths2,430 sq ft

17 Kittredge Rd, Pittsfield, MA 01201

Viewing page 3 of 8

Vintage Homes for Sale in Berkshire County

There are currently 312 vintage homes for sale in Berkshire County at a median listing price of $470K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Berkshire County stay on the market for 77 days. This map is refreshed with the newest listings in Berkshire County every 15 minutes.

In the past month, 182 homes have been sold in Berkshire County. In addition to houses in Berkshire County, there were also 87 condos, 5 townhouses, and 83 multi-family units for sale in Berkshire County last month. Find your dream home in Berkshire County using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Berkshire County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Berkshire County. If you're looking to sell your home in the Berkshire County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Berkshire County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

More real estate resources for Berkshire County, MA

Nearby Counties

Cities

Nearby Counties with Vintage Homes

Nearby Cities with Vintage Homes

More to explore in Berkshire County, MA

How to buy a house in Berkshire County, MA

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Massachusetts

Copyright 2025 PrimeMLS All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate for sale on this website comes in part from the VOW Program of PrimeMLS. Data last updated Mon Dec 01 2025 on the search page

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.