20

Stockbridge, MA Homes for Sale

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  • /5

    $998,000

    • Land
    • 9 Acres
    • $109,670 per Acre

    19 and 21 Wheatleigh Dr, Stockbridge, MA 01240

    RARE LUXURY: READY-to-BUILD MODERNIST RETREAT on EXCLUSIVE PRIVATE POND minutes to TANGLEWOODWelcome to a once-in-a-lifetime opportunity in the heart of the Berkshires. Set on 9.1 acres approximately acres of pristine land, this exceptional estate parcel offers frontage on tranquil Lily Pond, a private, non-motorized body of water that ensures peace, privacy, nature and views. Comprising the

    Agent Photo

    Selina Lamb

    BIRCH PROPERTIES

    (413) 343-4919

    19 and 21 Wheatleigh Dr, Stockbridge, MA 01240
  • /40

    $1,795,000

    • 4 Beds
    • 3 Baths
    • 5,469 Sq Ft

    17 East St, Lenox, MA 01240

    Nestled just north of Stockbridge, MA, this elegantly expanded brick Federal estate offers a harmonious blend of historic charm and modern design on 13+/- acres (9 conserved.) Originally built in the 1830s, the Carter Estate has been artfully expanded and renovated and boasts over 5,400sf of light-filled, luxurious living space, ideal for those seeking a private yet gracious lifestyle.As you

    Agent Photo

    Selina Lamb

    BIRCH PROPERTIES

    (413) 300-6860

    17 East St, Lenox, MA 01240
  • /6

    $425,000

    • Land
    • 3.30 Acres
    • $128,788 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.

    Agent Photo

    Selina Lamb

    Birch Properties

    (413) 343-5283

    9 Wheatleigh Dr, Stockbridge, MA 01262
  • /6

    $425,000

    • Land
    • 3.30 Acres
    • $128,788 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.

    Agent Photo

    Selina Lamb

    BIRCH PROPERTIES

    (413) 722-5098

    9 Wheatleigh Dr, Stockbridge, MA 01262
  • /6

    $650,000

    • Land
    • 19 Acres
    • $34,211 per Acre

    0 Mohawk Lake Rd, Stockbridge, MA 01262

    Discover a rare opportunity to own a piece of history in Stockbridge, available for the first time in over 120 years. This stunning land offers a private setting perfect for building your dream home, while being just moments away from the renowned Norman Rockwell Museum, Chesterwood, the enchanting Berkshire Botanical Gardens, and the charming downtown Stockbridge, all within a 3-mile radius.

    Agent Photo

    Gary Fuls Jr

    RE/MAX TRANSITIONS

    (413) 884-5511

    0 Mohawk Lake Rd, Stockbridge, MA 01262
  • /55

    $2,500,000

    • 5 Beds
    • 5.5 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
  • /40

    $1,795,000

    • 4 Beds
    • 4 Baths
    • 3,524 Sq Ft

    1 Old Tree Farm Rd, Stockbridge, MA 01262

    Impeccably Renovated Stockbridge Country Retreat. Minutes from Stockbridge, Lenox and Tanglewood, in the heart of the Berkshires cultural corridor, a rare opportunity in a perfect setting on 4.25 level, landscaped acres. Surrounded by mature trees and curated gardens, this home blends classic design with modern updates, offering refined style throughout. White oak floors, three full baths, a gas

    Suzann Ward HOUSATONIC REAL ESTATE

    1 Old Tree Farm Rd, Stockbridge, MA 01262
  • /55

    $1,675,000

    • 4 Beds
    • 2 Baths
    • 2,200 Sq Ft

    5 Glendale Rd, Stockbridge, MA 01262

    Two Dwellings on almost four acres.Just a very special property. Located between the Rockwell Museum and the Botanical Garden. You are moments from Tanglewood. Equidistant from Lenox and Great Barrington providing easy access to the Berkshires wonderful restaurants. The main house has four bedrooms and two baths , while the guest cottage adds another bedroom, bath, and large living room. The

    Martha Piper THE KINDERHOOK GROUP - PITTSFIELD

    5 Glendale Rd, Stockbridge, MA 01262
  • /42

    $485,000

    • 2 Beds
    • 2 Baths
    • 1,296 Sq Ft

    42 East St, Stockbridge, MA 01262

    Set on 6.4 scenic acres, this classic New England farmhouse captures the timeless spirit of Stockbridge, a town beloved for its rich history and cultural legacy. This 2-bed 2-bath home offers authentic charm, featuring beautiful hardwood floors, a spacious kitchen, family room + 1st floor full bath, and a welcoming front porch that evokes a slower, simpler time. Thoughtful updates include a newer

    Conor Meehan STONE HOUSE PROPERTIES, LLC

    42 East St, Stockbridge, MA 01262
  • /29

    $912,000

    • 4 Beds
    • 4 Baths
    • 2,280 Sq Ft

    21 East St, Stockbridge, MA 01262

    **Price Improvement** Nestled in the heart of the Berkshires, this spaciously built 2003 Colonial sits on over 14 acres, offering privacy, potential, and long-term value. Currently operating as a doggy day care, but you wouldn't know it when you walk inside! Well-maintained & cared for. Recent updates include the kitchen, bathrooms, carpets, back deck, and front landscaping, while still leaving

    Brianna Boffoli Cameron Prestige, LLC

    21 East St, Stockbridge, MA 01262
  • /19

    $949,000

    • 11 Beds
    • 6 Baths
    • 4,863 Sq Ft

    Unlisted Address

    Fully Rented In Town 5-Family Investment Opportunity. Home office available with a bathroom. Short walk to Post Office, Restaurants, Library and the Red Lion Inn. Stockbridge Town Park located across the street and hiking trails at the end of the street. See pictures.

    Matt Carlino MACCARO REAL ESTATE

    Unlisted Address
  • /24

    $299,900

    • 1 Bed
    • 1 Bath
    • 658 Sq Ft

    2 Wallace Rd Unit DH-B, Stockbridge, MA 01262

    Come experience this charming condo in the beautiful Heron Pond Community in Stockbridge. Thoughtful use of space with large, private front patio facing expansive manicured lawns and gardens. Enjoy 1-level living, (1-bed,1-bath with separate dining room) fully applianced kitchen with pantry and instant boiling water faucet. Washer and Dryer included. Zoned smart heating thermostats.

    Susan Calkins STONE HOUSE PROPERTIES, LLC

    2 Wallace Rd Unit DH-B, Stockbridge, MA 01262
  • /50

    $2,250,000

    • 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
  • /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

    $1,995,000

    • 6 Beds
    • 8 Baths
    • 10,507 Sq Ft

    14 Pine St, Stockbridge, MA 01262

    Prime Owner-User/Investment Property in the heart of historic Stockbridge. Currently an Educational Facility with Retail, Office and Residential Units. Can be combined for Offices, Medical, Educational, Gallery, Apartments/Condos, or any use that demands a location in one of the most well known and loved towns in America. Fully upgraded mechanicals, large Parking facilities and Handicapped

    Steven Weisz WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    14 Pine St, Stockbridge, MA 01262
  • /50

    $425,000

    • 2 Beds
    • 2 Baths
    • 1,647 Sq Ft

    2 Wallace Rd Unit 2E, Stockbridge, MA 01262

    Welcome to Heron Pond Condominiums in charming Stockbridge, where comfort meets convenience in a tranquil setting. This beautiful condominium offers an ideal combination of spacious living and cozy charm, featuring 2 or 3 bedrooms and 2 full baths. The screened porch is ideal to relax and enjoy nature without the bugs, a serene space to unwind, whether you're enjoying morning coffee or evening

    Paula McLean PAULA MCLEAN REALTORS INC.

    2 Wallace Rd Unit 2E, Stockbridge, MA 01262
  • /26

    $239,000

    • Land
    • 8 Acres
    • $30,508 per Acre

    13 Rattlesnake Mountain Rd, Stockbridge, MA 01262

    PRIME BERKSHIRE LAND - FEEL 'AWAY FROM IT ALL' YET YOU ARE MOMENTS FROM THE BEST OF THE BERKSHIRES. $158,000+ UNDER ASSESSED VALUESet on a serene & forested country road, this location makes the perfect retreat - yet you are in the heart of the Berkshires just minutes to Stockbridge & Lenox, Tanglewood, The Bowl, The Mount, Kripalu, Great Barrington, the Pike, shopping & more. The single home

    Chapin Fish WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    13 Rattlesnake Mountain Rd, Stockbridge, MA 01262
  • /16

    $295,000

    • Land
    • 25 Acres
    • $11,697 per Acre

    0 Glendale Rd Unit 245211, 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 245211, Stockbridge, MA 01262
  • /63

    $1,100,000

    • 4 Beds
    • 3.5 Baths
    • 2,861 Sq Ft

    1 Train Hill Rd, Stockbridge, MA 01262

    This Stockbridge Colonial has it all....location, separate guest suite and plenty of country chic design. This historic home boasts all the charm of yesteryear with fabulous wide pine floors, state of the art country kitchen that retains it's charm, formal dining room with fireplace, gracious banister to the second floor of guest bedrooms with renovated bath all while seamlessly blending with the

    Cortney Dupont COHEN & WHITE ASSOCIATES

    1 Train Hill Rd, Stockbridge, MA 01262
  • /25

    $160,000

    • 3 Beds
    • 1 Bath
    • 792 Sq Ft

    59 High St, West Stockbridge, MA 01236

    This lovely spot is in South County, close to Stockbridge, Lenox, and Great Barrington. You can kayak or canoe as you're not far from the Housatonic River. 1.16 acres of mostly open land with a mobile home. The town of West Stockbridge clears the roads, and Housatonic Water Company supplies water. The boiler was installed in 2018, the roof was redone in 2014, and the windows were replaced in

    Mark Harris SIGNATURE ASSOCIATES

    59 High St, West Stockbridge, MA 01236

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.

Frequently Asked Questions

What is the average home price in Stockbridge, MA?
Homes for sale in Stockbridge, MA have an average home price of $1,397,475.
How many homes have sold over the last 12 months in Stockbridge, MA?
68 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 $1,795,000. If you put a 20% down payment of $359,000 and had a 30-year fixed mortgage with an interest rate of 6.72%, your estimated principal and interest payment would be $9,290 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $398K a year to afford the median home price in Stockbridge.
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, Lenox Memorial High School and Morris Elementary School. Browse all the schools in Stockbridge, MA to learn more.

Home Trends in Stockbridge, MA

Housing Trends

Median Sale Price
$1,900,000
Median Single Family Sale Price
$1,900,000
Median 2 Bedroom Sale Price
$425,000
Median 1 Bedroom Sale Price
$299,900
Average Price Per Sq Ft
$566
Number of Homes for Sale
5
Last 12 months Home Sales
68
Months of Supply
0.90
Median List Price
$1,795,000
Median Change From 1st List Price
-6%
Median Home Sale Price YoY Change
274%
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