Exquisite, fully renovated farmhouse on private lane abutting nature reserve in heart of Stockbridge close to Red Lion. Foyer leads into an open plan LR/DR/Kit w/ beamed ceilings, hardwood floors, FP, oak slab island, marble counters, chef's stainless appls. Bright LR w/ floor-ceiling windows & French doors open onto patio w/ dining area. Huge 1st floor main BR suite w/ vltd ceils, walls of windows, WIC's, sitting area & luxurious marble BA w/ dbl sinks & shower. A half bath and laundry/storage room complete the 1st floor. 2nd floor has 3 BRs, 2 BAs (1 en-suite) & a 2nd LR + 2nd laundry. An open bonus space for a gym, office or playroom & WI cedar closet on the 3rd floor. Mature trees grace the charming back garden w/ patio. A 2-car garage & A/C complete this atmospheric, tranquil oasis!

Ideally situated in the heart of downtown Stockbridge, this 1860 colonial home has been stylishly updated and is move-in ready. The stunning first floor has three spacious adjoining living areas, including a central dining area and a family room with fireplace. The renovated kitchen has a chef's range and a large island perfect for gathering around. In the rear of the first floor is one of the home's two primary en-suite bedrooms, both with gas fireplaces. Take the back or front staircase to the second floor, which has the second primary en-suite bedroom, a central sitting area, and three more bedrooms, each with their own bathroom. A light filled loft/office and a vaulted-ceiling media room are found at the rear of the second floor - a perfect place for work or entertainment.

CIRCA 1824 GEM on 4.3 ACRES OF MEADOWS AND WOODS IN THE HEART OF THE HISTORIC VILLAGE OF STOCKBRIDGE. Walk to shops, restaurants, town tennis courts, the library, the Stockbridge Golf Club, the Berkshire Theatre Festival and more. The David Dudley Field house is steeped in history remaining in the Field family until 1984. The current owners have lovingly maintained and cherished this exceptional property for 40 yrs. The gracious interior is bathed in natural light and full of beautiful period details. Front and back staircases, pocket doors, built-in shelving, exceptional fireplace mantels, beautiful floors, etc. The carriage barn is a delight. An exceptional property perfectly located in the center of Berkshire activities. Lenox and Great Barrington are only a quick 10 minutes away.

THE TRIFECTA-Looking for a beautiful home that includes a large outbuilding with tons of potential and an extra building lot to boot? This property is the winning ticket!WIN-This 3 bedroom/3 bath 2,563 sq/ft home was built in approximately 1997 by the owner, who happens to a fine home builder and cabinetmaker! Meticulous attention to detail and craftsmanship can be found in every room, whether it's the antique paneling in the dining room, the antique stained glass found throughout the house, or the brand new kitchen full of custom cabinetry and countertops - this house just oozes craftsmanship! This house features a large living room with fireplace, dining room, office/family room, and a large, open kitchen with a central island.

A Magnificent 6 bedroom stucco residence less than a mile to the center of Stockbridge. Enjoy views of the golf course and mountains in the distance. Five fireplaces, a beautiful eat in kitchen, stunning butlers pantry with a cozy nook to sit in, and a sun filled spacious dining room. Read a good book in the beautiful library next to one of the five fire places throughout the house. Step out beautiful French doors to your screened in patio which leads to a well lit and heated pool. A 20 ft hallway wall of built in cabinets and closets leading to the primary bedroom. Three en suite bedroom areas for guests and family. Electric car charger in the heated garage. Majestic stonewalls. Not far to all attractions Tanglewood, Norman Rockwell, ski areas etc. A must see!

Rare; a renovated historic farmhouse abutting conserved land in the center of Stockbridge at the end of a private, quiet lane. The 3 season front porch with new Pella windows looks over a sunny lawn. The flow of first floor rooms allow for space and togetherness. There is a proper mudroom and butler's pantry. The bedrooms on the second floor are sun drenched, with tall ceilings and lovely restored wood floors. All 4.5 baths in the house have been remodeled with elegant detail. The third floor remains a fun recreational space for overflow family, guests, office or exercise. With utility upgrades, owned solar panels, and new windows, this is a highly functional 21st century house with the softness and warmth of an antique. Walk to tennis, golf, Ice Glen, dining, and the library. Glorious.

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. 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.

Welcome to 14 Pine Street, a unique and vibrant property nestled in the heart of picturesque Stockbridge, MA. This versatile building offers an ideal blend of commercial and residential spaces, making it an outstanding investment opportunity for those seeking a dynamic property in a central location. The property went through extensive renovations in 2019, including the following upgrades: Installation of upper parking lot, sidewalks and ramps, retaining wall and landscaping, drainage and rain garden, roof, updated all 4 boilers, repainted exterior, and a full renovation of the Ground Floor (new bathrooms, kitchenette, lighting, and two new egresses). The Main Floor offers a flexible commercial space, boasting a large assembly room with vaulted ceilings and oversized windows that flood

Welcome to 14 Pine Street, a unique and vibrant property nestled in the heart of picturesque Stockbridge, MA. This versatile building offers an ideal blend of commercial and residential spaces, making it an outstanding investment opportunity for those seeking a dynamic property in a central location. The property went through extensive renovations in 2019, including the following upgrades: Installation of upper parking lot, sidewalks and ramps, retaining wall and landscaping, drainage and rain garden, roof, updated all 4 boilers, repainted exterior, and a full renovation of the Ground Floor (new bathrooms, kitchenette, lighting, and two new egresses). The Main Floor offers a flexible commercial space, boasting a large assembly room with vaulted ceilings and oversized windows that flood

Step into the charm of history with this renovated exceptional property nestled in the picturesque town of Stockbridge, just off Main Street. A meticulously renovated 4-bedroom, 4-bath historic home offers elegant living spaces with the convenience of modern amenities such a solar array providing all electricity, a car charger and central air. The new eat-in kitchen offers SubZero, BlueStar, Vent-A-Hood and Bosch appliances, while overlooking the Kampoosa Brook and a private swimming hole. The Millhouse, as it's known, one of the first in Stockbridge is a 3-bedroom, 3-bath guest house with a great summer rental history. There's also a two-car garage and a fruit orchard. Enjoy the sound of the rushing brook from almost any window along with walking to town for an espresso, food or theater.

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!

Houses like this do not come along often! Two magnificent houses on 2.7 acres of serenity. The 17 Room mansion boasts Victorian architecture with modern luxuries. Named the Taggart house, this property has hosted celebrities and guests for many years. Almost 9000 square feet including a ballroom! Continue operating the business or live in it as your dream home. The rear guest house is a 4,500 square foot modern post and beam farmhouse built in 2006 with many beautiful recent renovations. Kayak from your private beach on the Housatonic River, stroll into Town and all that Stockbridge has to offer.

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

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.

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 .