Stockbridge, MA Homes for Sale

/42
$1,650,000
- 4 Beds
- 3 Baths
- 7,027 Sq Ft
17 East St, Stockbridge, MA 01262

Architecturally iconic and rich with history, this brick Federal home and its gracefully conceived mid-1990s expansion offer a rare opportunity for a buyer with vision. The last major renovation paired the 1830s structure with an addition that respects the original proportions while opening new possibilities for contemporary living. Set along the Stockbridge–Lenox corridor on 13+/- acres (9

Selina Lamb

Birch Properties

(413) 300-6860

17 East St, Stockbridge, MA 01262
/6
$395,000
- Land
- 3.3 Acres
- $119,697 per Acre
9 Wheatleigh Dr, Stockbridge, MA 01262

RARE OPPORTUNITY to build your new Berkshires home moments from Tanglewood's back gate and share deeded rights to a private beach on the Stockbridge Bowl too. Lovely and private, lightly wooded parcel on private lane with frontage on Lily Pond. Wheatley Drive is a private Rd. There is a voluntary HOA. Contribution of $1,000. annually for road maintenance and plowing is voluntary.

Selina Lamb

Birch Properties

(413) 343-5283

9 Wheatleigh Dr, Stockbridge, MA 01262
/8
$998,000
- Land
- 9.1 Acres
- $109,670 per Acre
19 and 21 Wheatleigh Dr, Stockbridge, MA 01240

Exceptional ready-to-build opportunity in the heart of the Berkshires. This rare 9.1-acre estate parcel offers direct frontage on tranquil Lily Pond, a private, non-motorized body of water known for its serenity, protected natural setting, and long, unobstructed views. A winding driveway follows a charming brook and leads across a brand-new bridge to an incredibly private pond-front building

Selina Lamb

Birch Properties

(413) 343-4919

19 and 21 Wheatleigh Dr, Stockbridge, MA 01240
/6
$395,000
- Land
- 3.3 Acres
- $119,697 per Acre
9 Wheatleigh Dr, Stockbridge, MA 01262

RARE OPPORTUNITY to build your new Berkshires home moments from Tanglewood's back gate and share deeded rights to a private beach on the Stockbridge Bowl too. Lovely and private, lightly wooded parcel on private lane with frontage on Lily Pond. Wheatley Drive is a private Rd. There is a voluntary HOA. Contribution of $1,000. annually for road maintenance and plowing is voluntary.

Selina Lamb

BIRCH PROPERTIES

(413) 722-5098

9 Wheatleigh Dr, Stockbridge, MA 01262
/50
$845,000
- 4 Beds
- 3.5 Baths
- 2,955 Sq Ft
9 Castle Hill Rd, Stockbridge, MA 01262

Tucked away on a quiet country road just minutes from the heart of historic Stockbridge, this 3.49-acre property pairs timeless New England charm with modern comforts. The star of the show is a beautifully updated red farmhouse with 3 bedrooms and 2.5 bathrooms, set on a sunny, bucolic lot that feels worlds away--yet is moments from downtown.The main house has been thoughtfully renovated,

Selina Lamb

BIRCH PROPERTIES

(413) 269-8632

9 Castle Hill Rd, Stockbridge, MA 01262
/63
$1,300,000
- 4 Beds
- 2 Baths
- 2,548 Sq Ft
18 Goodrich St, Stockbridge, MA 01262

This fine, four-bedroom, two bath colonial saltbox home just south of the village of Stockbridge is a handmade work of art and an important slice of Stockbridge history. It was constructed on or about 1750. There are patinaed wide board floors throughout as well as five fireplaces (three wood and two gas) and much original hardware. The home is surrounded by perennial gardens and a formal,

Robert Doerr LANCE VERMEULEN RE, INC., LENOX

18 Goodrich St, Stockbridge, MA 01262
/55
$1,490,000
- 4 Beds
- 2 Baths
- 2,200 Sq Ft
5 Glendale Rd, Stockbridge, MA 01262

''Best of Berkshire Living: Gardens, Grand Trees & Income-Ready Guest Cottage''Between the Rockwell Museum and Botanical Garden, minutes from Tanglewood, this nearly 4-acre Berkshire property offers two distinct homes surrounded by heirloom trees and landscaped gardens. The 4BR, 2BA main house features a first-floor primary suite with sunroom, spacious living areas, and central A/C. The charming

Martha Piper THE KINDERHOOK GROUP

5 Glendale Rd, Stockbridge, MA 01262
/51
$2,100,000
- 4 Beds
- 4 Baths
- 2,738 Sq Ft
8 Yale Hill Rd, Stockbridge, MA 01262

A RARE BEAUTY ON HISTORIC YALE HILL! Discover an historically significant gem in this perfectly renovated home! Peacefully tucked away from it all, yet close enough to enjoy a stroll to town, tennis, Library, golf & restaurants.Chef's Kitchen, large flexible living spaces, 4 Bedrooms, 4 Baths, tall ceilings and charm galore. The Mill House, transformed into a cozy Guest quarters, with 3

Helen Mullany HELEN MULLANY REAL ESTATE, LLC

8 Yale Hill Rd, Stockbridge, MA 01262
/63
$2,185,000
- 3 Beds
- 2.5 Baths
- 2,952 Sq Ft
14 Old Tree Farm Rd, Stockbridge, MA 01262

Set on a quiet country road w/ private driveway, this charming 3 BR, 2.5 BA home sits on 8 picturesque acres just minutes from Tanglewood, Stockbridge Bowl & the villages of Stockbridge, Lenox & West Stockbridge. Perfect for outdoor enthusiasts, culture lovers or anyone seeking a peaceful Berkshire retreat. The location offers hiking, yoga & wellness centers, boating, skiing, & convenient access

Claire Pollart LANCE VERMEULEN RE, INC

14 Old Tree Farm Rd, Stockbridge, MA 01262
/55
$599,000
- 3 Beds
- 3 Baths
- 2,295 Sq Ft
86 E Main St, Stockbridge, MA 01262

Prime location just a short distance to Stockbridge Village, Tangelwood, Berkshire Theatre Group and many more cultural attractions here in the beautiful Berkshires. Sprawling backyard with Housatonic River views. Open common spaces with ample space, exposed beams, character and wood flooring. The second level offers two bedrooms, full bath, large landing flex space and office/sitting area.

Cortney Dupont COHEN & WHITE ASSOCIATES

86 E Main St, Stockbridge, MA 01262
/30
$895,000
- 3 Beds
- 2.5 Baths
- 2,218 Sq Ft
200 Old Stockbridge Rd Unit Vanna 3, Stockbridge, MA 01262

Welcome to The Vanna Building at Winden Hill. First time to the market in nearly thirty years this is an excuisite example of Period living. The sun drenched Condo has 12 ft high ceilings, original marble fireplaces and uninterupted SW views as far as the eye can see. The first floor comprises of the extra large living room, dining room and kitchen, laundry and half bath. There are three bedrooms

Fintan Hanley COMPASS MASSACHUSETTS , LLC GB

200 Old Stockbridge Rd Unit Vanna 3, Stockbridge, MA 01262
/36
$278,800
- 1 Bed
- 1 Bath
- 658 Sq Ft
2 Wallace Rd Unit DH-B, Stockbridge, MA 01262

Looking for one-level living in the heart of the Berkshires? Comfort, convenience and move-in-ready appeal is what you'll find at this Heron Pond condo! Well-maintained, 1 br/1ba unit filled with natural light includes living room, separate dining room, updated bath and galley kitchen. Outside, relax on your own stone patio. Enjoy peaceful surroundings, the pond, and beautifully kept grounds.

Pamela Roberts ROBERTS & ASSOC. REALTY, INC

2 Wallace Rd Unit DH-B, Stockbridge, MA 01262
/47
$585,000
- 2 Beds
- 2.5 Baths
- 1,935 Sq Ft
19 Hawthorne Rd Unit Carriage Barn E-2, Stockbridge, MA 01262

MOTIVATED SELLER! Beautiful Carriage Barn Unit located in the sought after White Pines. The main level has open common spaces that include a gracious great room with a wall of windows to let in the natural light, wet bar and wood burning fireplace. Generous dining room overlooking the picturesque sun porch with serene view and galley kitchen that is oversized with ample storage space and laundry

Cortney Dupont COHEN & WHITE ASSOCIATES

19 Hawthorne Rd Unit Carriage Barn E-2, Stockbridge, MA 01262
/43
$3,850,000
- 4 Beds
- 3.5 Baths
- 4,000 Sq Ft
21A Interlaken Rd, Stockbridge, MA 01262

Modern country living at its finest--crafted with exceptional quality, refined taste, and a true sense of warmth. A dramatic double-height entry and living room create a seamless dialogue with the surrounding landscape while offering the comfort of home. The main level features an open-concept kitchen, living, and dining area, anchored on one side by the primary suite and on the other by a

Jen Harvey COMPASS MASSACHUSETTS , LLC GB

21A Interlaken Rd, Stockbridge, MA 01262
/32
$549,000
- 2 Beds
- 1 Bath
- 1,300 Sq Ft
7 Park St, Stockbridge, MA 01262

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

Samantha Homeyer BIRCH PROPERTIES

7 Park St, Stockbridge, MA 01262
/30
$895,000
- 3 Beds
- 2.5 Baths
- 2,218 Sq Ft
200 Vanna #3 Old Stockbridge Rd, Stockbridge, MA 01262

Welcome to The Vanna Building at Winden Hill. First time to the market in nearly thirty years this is an excuisite example of Period living. This sun drenched Condo has 12 ft high ceilings, original marble fireplaces and uninterupted SW views as far as the eye can see. The first floor comprises of the extra large living room, dining room and kitchen, laundry and half bath. There are three

Fintan Hanley COMPASS MASSACHUSETTS , LLC GB

200 Vanna #3 Old Stockbridge Rd, Stockbridge, MA 01262
/19
$550,000
- 4 Beds
- 3 Baths
- 2,600 Sq Ft
15 W Stockbridge, Stockbridge, MA 01262

The ideal Berkshire escape can be yours. Prime location between historic Stockbridge & vibrant West Stockbridge, minutes to Tanglewood. This turnkey 4-bed, 3-bath home is a sanctuary of light where thoughtful upgrades ensure peace of mind. Key systems are new: a lifetime metal roof, 3 year old re-engineered and designed septic, high-efficiency Buderus boiler, and oversized windows that connect

C. Ethan Watt WILLIAM PITT SOTHEBY'S - SALISBURY

15 W Stockbridge, Stockbridge, MA 01262
/51
$599,900
- 3 Beds
- 2 Baths
- 1,292 Sq Ft
40 Prospect Hill Rd, Stockbridge, MA 01262

Location is everything with this light-filled contemporary ranch on Prospect Hill. Ready for quick occupancy! Five minutes from downtown Stockbridge or to Tanglewood and so close to the town beach on Stockbridge Bowl. This three bedroom, two bath home has been lovingly cared for. Living room and dining with hardwood floors, built-in shelving and built-in storage. Quality updates in the primary

Pamela Roberts ROBERTS & ASSOC. REALTY, INC

40 Prospect Hill Rd, Stockbridge, MA 01262
/16
$295,000
- Land
- 25.22 Acres
- $11,697 per Acre
0 Glendale Rd Unit 248566, Stockbridge, MA 01262

Beautiful 25 Acres in Stockbridge. Stockbridge Bowl, Tanglewood, the villages of Stockbridge, Lenox, and Housatonic are all nearby. The property consists of two separate building lots - the south lot with 12.56 acres, and the north lot with 12.66 acres. Potential for mountain views from both lots with some clearing. Many possibilities - build on the north lot and keep the south lot for extra

Sheila Thunfors STONE HOUSE PROPERTIES, LLC

0 Glendale Rd Unit 248566, Stockbridge, MA 01262
/2
$289,000
- Land
- 3.69 Acres
- $78,320 per Acre
0 Interlaken Cross Rd, Stockbridge, MA 01262

A pristine building lot in the heart of the Berkshires! Parcel B at Echo Valley is a 3.69-acre wooded, buildable lot offering a beautiful blank canvas for your dream home. Located off Interlaken Cross Road in Stockbridge, MA, this level parcel is easy to work with and provides excellent flexibility for siting your house, garage, and outdoor living spaces. Just minutes from Tanglewood, Stockbridge

Lisa Berry Simply Sell Realty

0 Interlaken Cross Rd, Stockbridge, MA 01262
/14
$399,000
- 2 Beds
- 1 Bath
- 1,298 Sq Ft
17 High St, West Stockbridge, MA 01236

AFFORDABLE OPPORTUNITY TO BUILD EQUITY!This cozy fixer-upper is the perfect chance for a first time buyer to create a home of their own. With solid bones, a welcoming front porch, and a detached garage ideal for work shop or extra storage. Located in a convenient setting, it's ready for your vision. A little work could mean a big reward.Housatonic Village a few steps away. Being sold ''as-is''.

Helen Mullany HELEN MULLANY REAL ESTATE, LLC

17 High St, West Stockbridge, MA 01236

Massachusetts Berkshire County Stockbridge

Why Live in Stockbridge

Stockbridge, MA, a small community in the Berkshires, is known for its sweeping mountain vistas, historic estates, and vibrant art scene. The town's Main Street is lined with local businesses, cozy coffee shops, and art galleries, anchored by the iconic Red Lion Inn. Stockbridge is a cultural hub, home to the Norman Rockwell Museum, which houses the world's largest collection of Rockwell's work, and other historic sites like Naumkeag and Chesterwood. The Berkshire Theatre Group and Tanglewood music venue offer a variety of performances, while nearby attractions like Jacob's Pillow and Mass MOCA provide additional cultural experiences. Outdoor recreation is abundant, with Monument Mountain Reservation and October Mountain State Forest offering hiking, fishing, and camping. Winter activities include snowmobiling and skiing at nearby resorts like Ski Butternut. The Stockbridge Golf Club and Stockbridge Bowl cater to golfers, boaters, and beachgoers. Housing options range from colonial-style farmhouses and Victorian-style homes to modern custom-built estates. The Berkshire Hills Regional School District serves the area, with highly rated schools such as Muddy Brook Regional Elementary and Monument Mountain Regional High School. Stockbridge is primarily car-dependent, with U.S. Route 7 and Interstate 90 providing access to nearby towns and Albany International Airport, 50 miles away.

Learn more about living in Stockbridge

Frequently Asked Questions

What is the average home price in Stockbridge, MA?

Homes for sale in Stockbridge, MA have an average home price of $1,043,808.

How many homes have sold over the last 12 months in Stockbridge, MA?

32 homes have sold in Stockbridge, MA over the last 12 months.

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

The most popular zip codes in Stockbridge, MA include 01262, 01266, 01240, 01238 and 01236.

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

The median home price in Stockbridge is $845,000. If you put a 20% down payment of $169,000 and had a 30-year fixed mortgage with an interest rate of 6.31%, your estimated principal and interest payment would be $4,190 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $180K a year to afford the median home price in Stockbridge. Learn how much home you can afford with our Home Affordability Calculator.

How are the schools in Stockbridge, MA?

Stockbridge, MA has highly rated public and private schools. Some of the best schools in Stockbridge based on Niche Grades are Berkshire Waldorf High School, The Montessori School of the Berkshires and Morris Elementary School. Browse all the schools in Stockbridge, MA to learn more.

Home Trends in Stockbridge, MA

On average, homes in Stockbridge, MA sell after 46 days on the market compared to the national average of 54 days. The median sale price for homes in Stockbridge, MA over the last 12 months is $777,500, down 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$777,500

Median Single Family Sale Price

$895,000

Median Townhouse Sale Price

$660,000

Median 2 Bedroom Sale Price

$566,500

Median 1 Bedroom Sale Price

$278,800

Average Price Per Sq Ft

$422

Number of Homes for Sale

Last 12 months Home Sales

Months of Supply

5.60

Median List Price

$845,000

Median Change From 1st List Price

Median Home Sale Price YoY Change

-3%

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