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27 Photos
COHEN & WHITE ASSOCIATES
$499,000
3 BD | 3 BA
Residential - Condo/Townhouse

Beautiful Garden House Unit located in White Pines. Very bright, open common spaces, cathedral ceilings, sunroom, three bedrooms. two and half baths, deck and stair chair lift. Association indoor pool, tennis courts, walking trails and association beach on the Stockbridge Bowl. Amazing location close to Tangelwood and the Village of Lenox. A must see!


53 Photos
HELEN MULLANY REAL ESTATE, LLC
$500,000
2 BD | 2 BA
Residential - Condo/Townhouse

Enjoy easy condo living, in a splendid Berkshire setting, with amenities! Adult community with association swimming, tennis, exercise room, & numerous areas providing serene spaces to relax and connect with nature. Featuring a spacious living room with fireplace, a large kitchen/dining area, a heated porch which opens to a large deck for entertaining. 2 Bedrooms, 2 full baths, a third room, a den by day, converts to a perfect third guest bedroom, with a full bath nearby. There is an in unit laundry, central A/C, and an attached garage. The grounds are tree lined, perfectly landscaped, and offer a scenic country feel. Nestled in a private setting bordered by woods, this tucked away gem is ready for occupancy. Pets welcome. Close to Stockbridge Main St., and many cultural attractions.


54 Photos
THE KINDERHOOK GROUP - PITTSFIELD
$589,000
9 BD | 9 BA
Residential - Single Family

Built in 1828, this well-maintained Brick Colonial sits on 3.30 acres, and offers amazing mountain views. Currently being used as a B & B, the main house is set up with 5 bedrooms, 4.5 baths, including an immense addition with Chefs kitchen, loft and screened porch. The 3-story barn presents itself with an attached garage, storage area, its own workspace. There are also 3 private bedrooms each with their own private bath, and outside sitting area. On the top level there is an apartment, which lends itself to an open concept style of living. Complete with kitchen, full bath, living, dining area and an incredible sleeping loft. Convenient location, close to many Berkshire attractions. Sale is subject to third party approval


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WILLIAM PITT SOTHEBY'S - GT BARRINGTON

Build your perfect home on this land sited along one of the most prestigious roads in Stockbridge.The property encompasses the entire corner running along the corner of Larrywaug and North Church St. or divide into two lots. Four acre zoning and this property has enough frontage and acreage for two building lots. With clearing there is the possibility of views from different sites on the property.


33 Photos
BERKSHIRE PROPERTY AGENTS
$625,000
2 BD | 1 BA
Residential - Single Family

Serenely located with 100+ feet of water frontage on the Outlet at the entrance to the Stockbridge Bowl, is this charming 2 bedroom, 1 bathroom four season home with a large barn. 3 bedroom septic system. Open plan generous living room/dining room/kitchen with a stone fireplace and views onto the lawn, mature trees and the water. Delightful screened in porch and large stone patio facing the water and dock. The large unfinished barn has great potential to be used as additional living space or an artist's studio. Come be transported by nature in this unique quiet waterside oasis just a few minutes drive to Tanglewood, and the centers of Lenox and Stockbridge.


40 Photos
LANCE VERMEULEN RE, INC
$679,000
3 BD | 3 BA
Residential - Single Family

A convenient location in Stockbridge with Lenox nearby, too! This property is part of the Mahkeenac Terrace association on the east shore of Stockbridge Bowl. Single level living. Large master suite with sitting area, gas fireplace. Open kitchen living room with 14!ft eating island, floor to ceiling windows, gas fireplace. Large private patio with built in grill and refrigerator. Out building provides additional entertainment space plus storage for winter months. Swim or dock boat ( annual fee) at private association beach.


26 Photos
WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY
$699,000
4 BD | 2 BA
Residential - Single Family

BERKSHIRE RETREAT-Tucked away on 6 beautiful acres with a large cleared area and surrounding forest. This property has two maintained walking trails and a sweet little creek towards the back of the land. This 4 bedroom, 2 bath contemporary has loads of privacy yet close all your favorite Berkshire destinations. Large open living and dining with fireplace. 2 bedrooms on first floor and 2 more bedrooms on lower level. Large oversized two car garage. Spacious screened in porch with exterior deck. Central air. The property continues all the way to Old Tree Farm Road with ample frontage, possible building lot. Conveniently located in between Stockbridge and Lenox with only a 4 minute drive to the Stockbridge Bowl public boat launch area. Make this your next home.


32 Photos
BROCKMAN REAL ESTATE, LLC
$725,000
3 BD | 3 BA
Residential - Single Family

White Pines Country Villa with Stockbridge Bowl Beachfront.Light-filled and spacious! Huge windows and vaulted ceilings invite the sunlight and stunning meadow views into this coveted end-unit White Pines condo. The first floor has it all - a large primary bedroom and bathroom, a perfect-for-entertaining great room, an eat-in kitchen, half bath, wood fireplace, and a big deck overlooking the green meadows below. The downstairs has ample space for family and friends, with an awesome ''kids'' bedroom or games room, guest bedroom, full bath, and a stylish office with attached deck. Get a head-start on next year's summer season - private beachfront on the Bowl and walking distance to Tanglewood! Amenities also include an indoor pool, tennis courts, and clubhouse with exercise room & sauna.


27 Photos
BROCKMAN REAL ESTATE, LLC
$725,000
3 BD | 3 BA
Residential - Condo/Townhouse

White Pines Country Villa with Stockbridge Bowl Beachfront.Light-filled and spacious! Huge windows and vaulted ceilings invite the sunlight and stunning meadow views into this coveted end-unit White Pines condo. The first floor has it all - a large primary bedroom and bathroom, a perfect-for-entertaining great room, an eat-in kitchen, half bath, wood fireplace, and a big deck overlooking the green meadows below. The downstairs has ample space for family and friends, with an awesome ''kids'' bedroom or games room, guest bedroom, full bath, and a stylish office with attached deck. Get a head-start on next year's summer season - private beachfront on the Bowl and walking distance to Tanglewood! Amenities also include an indoor pool, tennis courts, and clubhouse with exercise room & sauna.


25 Photos
COHEN & WHITE ASSOCIATES
$798,500
3 BD | 2 BA
Residential - Single Family

This Circa 1930's colonial w/classic gambrel roof located on one of the most picturesque roads in the Berkshires is just minutes from Main St. Stockbridge, the Stockbridge Bowl beachfront and Tanglewood just down the road. The addition of a Great Room where all can gather with direct access to a vaulted ceiling dining area overlooking the fabulous acreage with mountain view make this a most welcoming home. Wonderful spacious decking is the perfect spot to enjoy the privacy and magnificent mature trees and landscaping with a backdrop of rolling hills. Formal living and dining rooms, spacious eat in country kitchen, three bedrooms and two full baths with lovely pastoral vistas from all, offer you the opportunity to enjoy living in a most comfortable home in a fantastic Berkshire location!


8 Photos
BERKSHIRE PROPERTY AGENTS, LLC

WATERFRONT: A rare opportunity to build a dream home on very private property with 460 ft of waterfront and panoramic views of Lily Pond, a renown unspoiled body of water that was cherished by the Gilded Age crowd. Extensive permitting in place for the driveway, dwelling and septic location. Located in Stockbridge within walking distance of Tanglewood, nearby Lenox village center, and the private beach at White Pines on Stockbridge Bowl. PRIME LOCATION AND VERY PRIVATE.


25 Photos
STONE HOUSE PROPERTIES, LLC
$839,000
4 BD | 3 BA
Residential - Single Family

Magnificent federal style brick home on 5 acres. A school house in 1848 and returned to original owners in 1873. The home has been expanded and lovingly cared for by the original owners for several generations. It is located in a spectacular, private and peaceful setting, with a large outdoor stone terrace with mature perennial gardens designed by a registered landscape architect.


48 Photos
LANCE VERMEULEN RE, INC
$875,000
5 BD | 3 BA
Residential - Single Family

1780's colonial set on over 12 beautiful acres. Few like this left in the Berkshires. Originally a Stagecoach stop between Hartford and Albany, this spacious home has those special details not found in modern buildings today. Built in cabinets, wide plank floors and fireplaces, one complete with bread ovens and usable hanging cooks pot. Dutch door looking out to lovely view. Recently updated kitchen leads into a greenhouse with fountain and radiant floors for year round use. Dining room table is the original to the home & is included in the sale to be passed onto the next family to make their own memories. There is a separate guesthouse with a full open kitchen, LR, bath, laundry room & loft. Several outbuildings including Tack room, chicken coop/playhouse, & much more. Can be sub-divided.


52 Photos
WHEELER & TAYLOR REALTY CO., INC.
$899,000
4 BD | 2 BA
Residential - Single Family

THREE HOUSES FOR SALE ON 11.6 PARK LIKE ACRES .1910 CONVERTED ANTIQUE BARN is now a warm and welcoming MAIN HOUSE with 4+ bedrooms, 2 full baths, large stone fireplace, cherry wood paneling, lots of windows, 2+ car garage .TWO ADDITIONAL RANCH STYLE HOUSES have a separate driveway and privacy. Perfect GUEST COTTAGE and CARETAKERS properties. Unique opportunity in a desirable area in Stockbridge.


55 Photos
WHEELER & TAYLOR REALTY CO., INC.

THREE HOUSES FOR SALE ON 11.6 PARK LIKE ACRES . 1910 CONVERTED ANTIQUE BARN is now a warm and welcoming MAIN HOUSE, with 4 + bedrooms and 2 full baths, cherry paneling, large stone fireplace and 2+ car garage with storage. TWO ADDITIONAL RANCH STYLE HOUSES are included with separate driveway and privacy. The perfect GUEST HOUSE AND CARETAKERS properties. Unique opportunity in an ideal location.


4 Photos
WILLIAM PITT SOTHEBY'S - GT BARRINGTON

Build your perfect home on this land sited along one of the most prestigious roads in Stockbridge.The property encompasses the entire corner running along Prospect Hill, Larrywaug and to North Church St. or divide into three lots. Four acre zoning and this property has enough frontage and acreage for three building lots. With clearing there is the possibility of views from different sites on the property.


38 Photos
HELEN MULLANY REAL ESTATE, LLC
$995,000
6 BD | 3 BA
Residential - Single Family

Gracious 1890 residence with carriage barn income property, graces the charming main street of Stockbridge. The main house is comprised of 4 bedrooms, double parlors w/fireplace, formal dining room, country kitchen and the most delightful screened porch. An attached 2 bedroom apartment with separate entrance, is ideal for extended family and guests. Distanced from the main house by a circular drive, the converted carriage barn sets behind, housing three apartments. Mature landscaping, perennial gardens, stone patios, and a 3 bay garage complete this idyllic compound. Red Lion Inn, Stockbridge Golf Club and theatre nearby.


4 Photos
HELEN MULLANY REAL ESTATE, LLC
$995,000
4 BD | 3 BA
Multi-Family

A gracious Main Street property with four rental apartments, a main house with four bedrooms, double parlors, country kitchen, two full baths, a wonderful screened porch and a three bay garage. The yard has wonderful out door spaces for the residents, and all a short walk to everything the town offers. Perfect for an investor owner occupier.


38 Photos
COHEN & WHITE ASSOCIATES
$998,500
7 BD | 7 BA
Residential - Single Family

What a beautiful home for TODAY! Set in the heart of Stockbridge -- that most gracious and iconic of Berkshire towns -- ''Seasons'' is a New England classic, a lovingly detailed, superbly renovated 1862 Greek Revival mansion, warm and welcoming. From the restful length of its shady porch to the elegantly appointed front parlor, from the serene formal dining room to its secluded bedroom retreats, ''Seasons'' manages to both welcome the world, while offering friends and family a perfect refuge. This spectacular all-season ''Getaway'' home, part 19th century, part 21st, generously arranged, with elegantly designed public rooms, and the pleasures of a spacious modern chef's kitchen with Multi-zone air conditioning throughout. In perfect order, it's waiting for YOUR fortunate family!


35 Photos
COHEN & WHITE ASSOCIATES

Rated #2 in the country in 2018 and #16 in the world, Seasons on Main is a nationally recognized top rated 1862 Greek revival B&B in the center of Stockbridge and has been lovingly restored to its original grandeur and maintained with the utmost care.This is your opportunity to own a turnkey business with a proven record of success, or to have as your own exquisite homestead.

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