Stockbridge Real Estate

MLS Number 243137

• Commercial
• Acreage 21
• Parking Spaces 100

Rarely does a property of such landmark significance, fully restored and in impeccable condition grace the market. Situated on 21.25 acres in desirable stockbridge on grounds landscaped by frederick law olmstead with views of stockbridge bowl and a short walk to tanglewood. This italianate building has been upgraded by famed architects tsao and mckown. The property offers 33 rooms, 19 ensuite bed rooms with high ceilings, luxurious baths and grand common rooms awaiting your imagination for a new life .

Listed by Cindy Welch of LANDVEST,INC.

MLS Number 243138

• Residential
• Bathroom 23
• Bedrooms 19
• Square Feet 22,000
• Acreage 21

Wheatleigh is the perfect marriage of the grandeur of a 16th century florentine palazzo and the comfort and elegance of the twenty first century. Imagine living in desirable lenox on 22 acres overlooking stockbridge bowl and the mountains and being within a short stroll to tanglewood! Henry cook in 1893 commissioned peabody and sterns to construct this italianate style home. It has since been updated by famed architects tsao and mckown for contemporary living. The 19 suites, guest rooms and baths set a new standard of style and sophistication and can accommodate many friends, business guests and family. Each of the bedrooms have high speed internet and bang and olufsen tv's . The state of the art fitness center, heated pool, and tennis court keep every one active.

Listed by Cindy Welch of LANDVEST,INC.

MLS Number 239285

• Residential
• Bathroom 9
• Bedrooms 5
• Square Feet 9,339
• Acreage 6.2

One of the berkshires' finest residences, basking in the idyllic mountain scenery. Designed and crafted to meticulous standards, this distinguished 6.2 acre compound is surrounded by captivating, protected vistas far and wide. In the enduring tradition of the regions iconic estates, this extraordinary residence is a place for life to the fullest, providing an endless source of enjoyment in exquisite indoor /outdoor spaces. Fine millwork and 9 fireplaces underscore the comfortably elegant environment. Lower-level entertainment (media)room, wine cellar, fitness studio. Elevator, computerized systems. 9,339 sf with 5 bedrooms,6 full/3half baths. Wraparound tiered terraces feature pool with pool house. Glorious terraced gardens and formal gardens with fountain. Separate 3 bedroom guest house

Listed by Patrice C. Melluzzo of WILLIAM PITT SOTHEBY'S - GT BARRINGTON

MLS Number 243745

• Residential
• Bathroom 7
• Bedrooms 7
• Square Feet 8,200
• Acreage 57

Significantly restored in 2024! Sellers have masterfully updated this legacy home w/ a cool & fresh aesthetic that preserves the integrity of its mid-century modern design. Updates to the 1st floor primary suite, kit, entertainment kit, bathrooms & freshly painted interiors are just a few of the improvements. The airy main living spaces w/ their expansive sliding glass doors offer sublime views of the resort-like grounds complete w/ manicured lawns, patios, in-ground pool, playground, newly resurfaced tennis/pickle ball court, gardens curated by a master gardener & distant mountain views. The 7 bedroom, 7 bathroom estate w/ 8200 sq ft of versatile living space prominently sited on 57+ acres is 3 hours to nyc and 2 hours to boston!

Listed by Nancy Cole of COMPASS MASSACHUSETTS,LLC.

MLS Number 244472

• Residential
• Bathroom 3
• Bedrooms 4
• Square Feet 5,469
• Acreage 13.1

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 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--perfect for painting or relaxing. The estate is oriented towards cultural and natural beauty with walking trails

Listed by Selina Lamb of BIRCH PROPERTIES

MLS Number 242787

• Residential
• Bathroom 2
• Bedrooms 4
• Square Feet 2,200
• Acreage 3.6

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 main house has central a/c while the guest cottage has mini splits. Gracious grounds are beautifully landscaped. Adorable play house for little ones. Several outbuildings. Garages for at least 5 cars. First floor primary bedroom with sunroom. Perfect site for a pool. Abuts protected land.

Listed by Martha Piper of WILLIAM PITT SOTHEBY'S - GT BARRINGTON

MLS Number 244348

• Residential
• Bathroom 4
• Bedrooms 4
• Square Feet 2,861
• Acreage 0.89

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 open great room for today's lifestyle living; a fabulous main floor primary bedroom with a wall of closets and an en suite renovated bath. From the spacious decking of the main house there is a romantic covered walkway that leads to separate guest quarters with a great room, bedroom, bath and kitchenette that has it's own private outdoor gathering space with firepit. The two car oversized garage

Listed by Cortney K Dupont and Brandon White of COHEN & WHITE ASSOCIATES

MLS Number 244496

• Residential
• Bathroom 4
• Bedrooms 4
• Square Feet 2,668
• Acreage 0.8

Meticulous and charming and recently renovated 4 bedroom, 4 bath antique cottage situated in a private story book setting along the banks of the kampoosa brook in a desirable stockbridge location. Thoughtful attention to detail at every turn creates a perfect marriage of old and new, making this jewel box a delightful surprise, and well suited for modern living. The house offers several cozy places to sit by the fire, overlook the garden and enjoy the sounds of the babbling brook. Exposed beam ceilings, original oversized fireplace and wide floor boards are just a few of the nods to the original roots of the house. The unique layout of the house provides two potential options for either guest or inlaw suites, each with their own entrances. The yard is beautifully landscaped to create

Listed by Susan Laidlaw of Compass Massachusetts,LLC

MLS Number 245131

• Land
• Acreage 35.07

Large parcel of land centrally located on a quiet road in stockbridge. Minutes to the town centers of stockbridge, lenox, and west stockbridge, as well as tanglewood, kripalu, the norman rockwell museum, and the berkshire botanical gardens. It is also walking-distance to the stockbridge bowl outlet and the berkshire art center.The land is mostly wooded, level, and dry with some open areas. Town water and sewer are on the street. It is an exceptional estate property but could potentially be subdivided in various ways.

Listed by Carole Murko of BOULDERWOOD GROUP

MLS Number 245401

• Condo
• Bedrooms 2
• Bathroom 3
• Year Built 1988
• Square Feet 1,853

Some of the best views the berkshires have to offer. One of the ''great estates'' conversions, winden hill condos are in stockbridge, but within 1.5 miles of downtown lenox and a short drive to tanglewood. Located in the smith building - this unit features 2 bedrooms each with private bath. Easy entertaining in the great room with fireplace and vaulted ceiling. French door leads to the spacious deck. Den/office with half bath serves as bonus third sleeping space. Natural gas heat, central a/c, charging station for your electric vehicle. Very short walk to the community pool, tennis/pickleball.

Listed by Pamela Roberts of ROBERTS & ASSOC. REALTY,INC