Classic red farmhouse on 3.49 bucolic acres just minutes from the heart of Stockbridge. This updated 3BR/2.5BA home blends original charm with thoughtful upgrades. Post and beam construction, a sleek gas fireplace, and a sunny open layout connect the living, dining, and kitchen areas. The first-floor primary suite includes a walk-in closet and private bath. Upstairs, two more bedrooms and a full bath offer space and flexibility. A spacious 1BR/1BA apartment above the attached garage is perfect for guests, rental income, or studio use. Proven short-term rental history adds investment appeal. Enjoy a contemporary deck overlooking lawns and trees—ideal for relaxing or entertaining under Berkshire skies. The property offers privacy, convenience, and timeless appeal in the town Norman Rockwell called home. Just minutes to downtown Stockbridge, with Lenox, Tanglewood, and Great Barrington close by. A rare blend of character, versatility, and location in the Berkshires.
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 4.16 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 fireplace and a spacious screened porch with mahogany flooring and ceiling fan. A separate one bedroom guest suite above the detached two car garage includes a full bath, kitchenette, private deck, and quiet seclusion for guests.
ICONIC STOCKBRIDGE BRICK FEDERAL ESTATEElegantly expanded brick Federal estate offers a harmonious blend of historic charm and modern design on 13+/- acres (9 conserved.) Built in the 1830s, the Carter Estate has been artfully expanded and boasts over 5,400sf of light-filled, luxurious living space.As you enter through classic stone walls and manicured hedgerows, you'll be welcomed by sweeping meadows and lush gardens. Time slows as you meander along stone pathways that lead to a charming red barn and a quaint stone summer cottage.Architectural details throughout the home reflect its historic Federal-style elegance, while modern updates ensure comfort and efficiency year-round. Gather by the cozy kitchen fireplace in the winter or open the doors to the blooming gardens in the warmer months. This home features four spacious bedrooms (septic design allows for up to eight bedrooms), making it versatile for various living arrangements.

Stockbridge is located in Massachusetts. Stockbridge, Massachusetts has a population of 1,827. Stockbridge is less family-centric than the surrounding county with 17.88% of the households containing married families with children. The county average for households married with children is 21.74%.
The median household income in Stockbridge, Massachusetts is $46,458. The median household income for the surrounding county is $63,159 compared to the national median of $69,021. The median age of people living in Stockbridge is 60.1 years.
The average high temperature in July is 80.9 degrees, with an average low temperature in January of 11.9 degrees. The average rainfall is approximately 47.2 inches per year, with 56.2 inches of snow per year.