9

Stockbridge, MA Houses for Sale

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  • /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
  • /70

    $1,299,000

    • 5 Beds
    • 4 Baths
    • 3,289 Sq Ft

    49 Main St, Stockbridge, MA 01262

    Improved stunning Stockbridge Village property that boasts an updated main house and includes a separate three apartment carriage house. The main property offers great natural light and ample common spaces that are gracious in size, updated lovely kitchen, five bedrooms, four baths, screened porch and inviting outdoor spaces. It has been thoughtfully updated while keeping the charm and character

    Cortney Dupont COHEN & WHITE ASSOCIATES

    49 Main St, Stockbridge, MA 01262
  • /64

    $1,299,900

    • 5 Beds
    • 4 Baths
    • 2,976 Sq Ft

    44 Prospect Hill Rd, Stockbridge, MA 01263

    Escape to incredible mountaintop views and woodland privacy on prestigious Prospect Hill Road, Stockbridge, in this contemporary treasure set on 7.43 secluded acres and minutes to Tanglewood, the Stockbridge Bowl, and all that is Berkshire. This exceptional five bedroom, four bath awe-inspiring home is a living art retreat, inviting you to own and experience nature's grandeur inside and out.

    Tonia Scalise WILLIAM PITT SOTHEBY'S - LENOX

    44 Prospect Hill Rd, Stockbridge, MA 01263
  • /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 spacious Colonial sits on over 14 acres, offering privacy, potential, and long-term value. With only two owners since it was built, the home has been well cared for and currently serves as both a private residence and a doggy daycare. Recent updates include the kitchen, bathrooms, carpets, back deck, and front landscaping, while

    Brianna Boffoli Cameron Prestige, LLC

    21 East St, Stockbridge, MA 01262
  • /43

    $1,100,000

    • 5 Beds
    • 3.5 Baths
    • 3,194 Sq Ft

    33 Interlaken Rd, Stockbridge, MA 01262

    Enjoy convenient one level living in this expanded contemporary ranch. Super location - Located less than 5 minutest to the main gates of Tanglewood, the Stockbridge Bowl for swimming, and Gould Meadows for a nature lovers hike. Sited at the end of a long winding driveway this 2+ acre parcel is level and sunny (ideal for a pool). 5+ bedrooms and 3 1/2 bathrooms including a suite with a

    Lori Rose STONE HOUSE PROPERTIES, LLC

    33 Interlaken Rd, Stockbridge, MA 01262
  • /34

    $1,295,000

    • 4 Beds
    • 2.5 Baths
    • 2,511 Sq Ft

    16 Glendale Middle Rd, Stockbridge, MA 01262

    VINTAGE EYEBROW COLONIAL WITH VIEWS & A POST AND BEAM ADDITION. Updated and renovated open concept plan dripping with charm in pristine condition. 2013 addition by renowned builder David Lanoue. Systems updated at that time. Gorgeous wide pine flooring, a chef's kitchen with custom cabinets a Viking Range, a stone farmers sink with windows overlooking the beautiful view. 4 Bedrooms, 2.5 baths,

    Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

    16 Glendale Middle Rd, 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
  • /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

Why Live in Stockbridge

Stockbridge is a seasonal community in the Berkshires known for its sweeping mountain vistas, historic estates, and vibrant art scene. The town's cultural hub includes the Norman Rockwell Museum, which houses the world's largest collection of Rockwell's work, and historic sites like Naumkeag and Chesterwood. Performing arts thrive with venues such as Tanglewood, the summer home of the Boston Symphony, and the Berkshire Theatre Group. Outdoor attractions include Monument Mountain Reservation and October Mountain State Forest, offering year-round recreation from hiking to skiing. Stockbridge's village center features cozy coffee shops, restaurants, local boutiques, and art galleries, anchored by The Red Lion Inn. The Berkshire Hills Regional School District serves the area, with highly rated schools like Muddy Brook Regional Elementary and Monument Mountain Regional High School. Homes range from colonial-style farmhouses to modern custom-built estates, with many properties retaining historic charm while offering modern amenities. Safety in Stockbridge is comparable to the national average, and residents enjoy walkability in the village center but rely on cars for grocery shopping and access to larger towns. U.S. Route 7 and Interstate 90 provide connectivity to nearby cities and Albany International Airport, 50 miles away.

Home Trends in Stockbridge, MA

Housing Trends

Median Sale Price
$500,000
Median Single Family Sale Price
$1,210,000
Median Townhouse Sale Price
$995,000
Median 2 Bedroom Sale Price
$350,000
Median 1 Bedroom Sale Price
$335,450
Average Price Per Sq Ft
$459
Number of Homes for Sale
5
Last 12 months Home Sales
15
Months of Supply
4.00
Median List Price
$691,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
-16%
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