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17 East St, Stockbridge
$1,510,000
4 Beds ⋅ 3 Baths ⋅ 73290001 MLS
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 conserved), the property is ready for a thoughtful, design-forward restoration. Beautiful natural light, high ceilings, and more than 5,000 sq ft provide an exceptional canvas. Stone walls, sweeping lawns, a classic barn, and a charming stone cottage invite imaginative reuse. For those who appreciate historic architecture and are ready to shape a property of scale and significance, 17 East Street offers a rare Berkshire opportunity.

17 East St, Stockbridge

Listing courtesy of Listing Agent: Selina Lamb from Listing Office: Birch Properties.
10 Prospect Hill, Stockbridge
$895,000
4 Beds ⋅ 2 Baths ⋅ 73538782 MLS
Rare opportunity on coveted Prospect Hill Road in Stockbridge. Offered for the first time in more than 40 years, this c.1880 residence is privately set on 3.5 acres just moments from downtown Stockbridge, the Red Lion Inn, Tanglewood, Lenox, and the Berkshires' renowned cultural attractions. The home offers approximately 2,515 square feet with wide-plank floors, exposed brick, wood beams, built-ins, and original character throughout. A spacious kitchen, dining area, living room with fireplace, first-floor bedroom, and flexible spaces provide a compelling canvas for renovation or reimagination. Three additional bedrooms and a finished third floor offer abundant possibilities for modern living. Expansive lawns, mature trees, privacy, and potential for a pool complete this exceptional offering. A rare chance to create a distinctive Berkshire home in one of Stockbridge's most desirable locations.

10 Prospect Hill, Stockbridge

Listing courtesy of Listing Agent: Selina Lamb from Listing Office: Birch Properties.
15 Mahkeenac Heights Rd, Stockbridge
$840,000
2 Beds ⋅ 2 Baths ⋅ 73431213 MLS
Chic and modern Berkshires retreat. Completed in 2022, this fully renovated property is one of only a handful of homes in Mahkeenac Heights to offer a rare double lot — a private, wooded setting just moments from Stockbridge Bowl and minutes to Tanglewood. The design is simple, modern, and sophisticated: a wall of glass frames the surrounding forest, filling the airy living space with light and creating a seamless connection to nature. Seasonal westerly views of the Stockbridge Bowl appear late fall through early spring. The main house offers 2 bedrooms plus a flexible loft, 1 full bath and 1 half bath, with a screened porch, wood stove, and outdoor dining areas for year-round living. A 10 × 10 study with its own deck and a separate cottage with power add flexible space for office, studio, or gym. This rare property blends modern architecture, full renovation, and exceptional acreage for the perfect Berkshires lifestyle.

15 Mahkeenac Heights Rd, Stockbridge

Listing courtesy of Listing Agent: Selina Lamb from Listing Office: Birch Properties.
19 and 21 Wheatley Drive, Stockbridge
$825,000
73366568 MLS
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 site. All major work is complete: fully permitted building site, architect-designed plans for a 5-bedroom modern home, drilled well, power brought to the site, and approved 5-bedroom septic design. The property also includes deeded rights to the private White Pines beach on the Stockbridge Bowl—an extraordinary amenity for swimming, boating, and enjoying one of the Berkshires’ most iconic lakes. Conveniently located minutes to Tanglewood, downtown Stockbridge, Lenox, and the region’s finest cultural, dining, and outdoor destinations.

19 and 21 Wheatley Drive, Stockbridge

Listing courtesy of Listing Agent: Selina Lamb from Listing Office: Birch Properties.
9 Wheatley, Stockbridge
$350,000
73226129 MLS
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.

9 Wheatley, Stockbridge

Listing courtesy of Listing Agent: Selina Lamb from Listing Office: Birch Properties.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

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