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32 Photos
ROBERTS & ASSOC. REALTY, INC
200 Old Stockbridge Rd
Berkshire - South
Stockbridge > MA > 01262
$539,000
2 BD | 3 BA
Residential - Condo/Townhouse

Some of the best views the Berkshires have to offer! Winden Hill condos are in Stockbridge, but within 1.5 miles of Lenox and short drive to Tanglewood. Two bedrooms each with private bath; great room with three sliders to the spacious deck. Den serves as bonus third sleeping space. Natural gas heat, central a/c. Enjoy gorgeous community pool, tennis/pickle ball court.


39 Photos
COHEN & WHITE ASSOCIATES
19 Hawthorne Rd
Berkshire - South
Stockbridge > MA > 01262
$549,000
2 BD | 3 BA
Residential - Condo/Townhouse

This White Pines Garden Unit is a must see if you are considering condominium living. Open living spaces with double volume glass to take in the view, fireplace, built-ins, dining in a glass gazebo and a state-of-the-art chair lift to take you to the beautifully finished lower level where the sun room, with tile flooring, has direct access to spacious decking and private courtyard outdoor space. Master bedroom en suite as well as a guest room en suite, in-unit laundry and an office complete this level. Indoor heated pool, exercise room, 2 Har Tru tennis courts, hiking trails, private beachfront on the sought after Stockbridge Bowl where you can swim or dock your kayak & boat...all within walking distance to Tanglewood!!


18 Photos
WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY
12 North Church St
Berkshire - South
Stockbridge > MA > 01262
$575,000
3 BD | 2 BA
Residential - Single Family

Contemporary Stockbridge Retreat - close to town and minutes to Tanglewood, this tastefully designed home is set on 7 private acres with southwesterly views. The upper level provides an open, light-filled floor plan that boasts a spacious kitchen, a dining area with built-in storage, and a living room complete with a double-sided fireplace. A set of sliding doors connects the dining room and living room to an expansive outdoor deck - a perfect space for summer entertaining. A versatile den and full bath complete the upstairs. On the lower level you will find three sizable bedrooms, another full bath, a laundry room and plenty of storage space. This home is the perfect retreat for someone looking for total privacy in a convenient location close to all of the Berkshires cultural attractions.


29 Photos
BERKSHIRE PROPERTY AGENTS
19 Hawthorne Rd
Berkshire - South
Stockbridge > MA > 01262
$579,000
3 BD | 3 BA
Residential - Condo/Townhouse

BEST INVESTMENT IN WHITE PINES. A premier condo community with a private beach on Stockbridge Bowl. Access to two tennis courts, and a wonderful indoor pool and pool house. Walking distance to Tanglewood. The first floor has a spacious open living/dining area with a wood-burning fireplace, kitchen with plenty of cabinets, half bath, and master bedroom and bath. Upstairs are two guest bedrooms which share a full bath. Lots of closet space. Located in ''The Meadows,'' this unit has pastoral views and a screened porch to enjoy summer evenings.


34 Photos
WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY, LENOX
74 East Main St
Berkshire - South
Stockbridge > MA > 01262
$629,900
6 BD | 5 BA
Residential - Single Family

Welcome to Stockbridge! Walk to town, The Red Lion Inn or to the Berkshire Theatre Festival from this lovely 6 bedroom in-town Victorian loaded with charm and historic character! This sunny, cheerful home features spacious rooms, period woodwork, wide board floors, built-ins, wood burning fireplaces and a two story addition that offers a family room with loft and a modern kitchen which opens out onto a large deck overlooking the beautiful back lawn and gardens. Further enhancing this homes livability is the separate one bedroom apartment, nicely updated and suitable as an in-law or an au-pair complete with separate entrance. Town water, sewer, natural gas and all updated utilities!


15 Photos
WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY
44 Lake Dr
Berkshire - South
Stockbridge > MA > 01262
$645,000
3 BD | 3 BA
Residential - Single Family

FURTHER PRICE REDUCTION! Spectacular lake front home with complete privacy, dock, level land & beautiful landscaping. Stockbridge Bowl is a swimming & boating paradise. Only minutes to Tanglewood, downtown Lenox, downtown Stockbridge, the Berkshires' best cultural attractions, skiing, hiking, biking & acclaimed farm to table restaurants. Don't miss this rare opportunity to own your dream home on magical Stockbridge Bowl.


46 Photos
STONE HOUSE PROPERTIES, LLC
6 Wheatley Dr
Berkshire - South
Stockbridge > MA > 01262
$649,000
3 BD | 3 BA
Residential - Single Family

Hand crafted architectural work of art. Extraordinary use of masonry, wood and glass. Delightful and unique details at every turn. One's eye is continually brought to the next level, the next space. A wonderful retreat in a wooded setting on a quiet dirt road only minutes to Stockbridge Bowl, a short walk to Tanglewood and a quick drive to downtown Lenox.


51 Photos
KELLER WILLIAMS BERKSHIRE
6 Goodrich St
Berkshire - South
Stockbridge > MA > 01262
$659,000
4 BD | 3 BA
Residential - Single Family

This amazing home has all of the charm of yesterday and enjoys todays updates! The kitchen is huge and has gorgeous counters and appliances.... The kitchen overlooks back ''sitting room''. Floors are wide plank wood and beautifully maintained. Large living spaces flow beautifully one to the next. Upstairs has four bedrooms, one a master with it's own en-suite bath. Outside is a great deck to enjoy warm summer night and fenced ''door yard''. And then there are the barns and apartment. Studio type space with loft, kitchen and a bath - this space could be a barn manager's space or rental space. Barn itself is a bank barn - with large (14x14 +/-) stalls and tack storage. There is a side shedrow for storage of farm tractors and such. Room for a small one car garage also. Down stair


20 Photos
WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY
23 Hawthorne Rd
Berkshire - South
Stockbridge > MA > 01262
$675,000
3 BD | 3 BA
Residential - Condo/Townhouse

Lake views from every room at this tastefully updated White Pines condo. Situated directly across from the Association's private beach on the Stockbridge Bowl, this Lakeside Villa offers a sunny and open floor plan, with hardwood floors, a gas fireplace, and an updated kitchen. The upstairs master bedroom features breathtaking views of the lake, custom California Closets, and a fully renovated en-suite bath. Downstairs you will find two additional bedrooms (one is currently used as an office with a Murphy bed), a shared bath, and a laundry room. Amenities include an indoor pool, Har-Tru tennis courts, a fitness center, kayak storage, a dock and mooring buoys. Minutes to Tanglewood, Stockbridge, and Lenox, this home is an exceptional value in a coveted location.


27 Photos
BERKSHIRE PROPERTY AGENTS
19 Hawthorne Rd
Berkshire - South
Stockbridge > MA > 01262
$685,000
3 BD | 3 BA
Residential - Condo/Townhouse

WHITE PINES COUNTRY VILLA-SINGLE FLOOR LIVING-SPACIOUS, TWO LEVEL CONTEMPORARY- HUGE FIRST FLOOR OPEN PLAN LIVING / DINING, ENTERTAINMENT WORTHY HOME WITH WOOD BURNING FIREPLACE, LARGE FIRST FLOOR MASTER SUITE WITH ATTACHED PORCH, EAT IN KITCHEN WITH AN ATTACHED GARAGE, HALF BATH , SKYLIGHTS, INTERIOR BALCONY, SW FACING DECK. - SUNNY WALK OUT LOWER LEVEL WITH A BEDROOM, SLEEPING DEN-BEDROOM, BATHROOM AND A OVERSIZED BONUS ROOM WITH WINDOWS AND CLOSETS (room enough for another bedroom suite)- PASTORAL AND SEASONAL MOUNTAIN VIEWS, PRIVATE BEACH AT THE STOCKBRIDGE BOWL KAYAK SPACE, INDOOR POOL, 2 TENNIS COURTS, GYM, PETS ALLOWED, WALKING DISTANCE TO TANGLEWOOD, WHEATLEIGH, CLOSE TO LENOX- 2.5+ HOURS FROM BOSTON OR NYC


37 Photos
ROBERTS & ASSOC. REALTY, INC
176 Old Stockbridge Rd
Berkshire - South
Stockbridge > MA > 01262
$689,000
3 BD | 4 BA
Residential - Condo/Townhouse

One-of-a-kind Winden Hill condo with magnificent westerly views! Come inside; prepare to be wowed! Open plan with cathedral ceiling in living/dining great room features gas fireplace, exposed beams, two sliders to large private deck. First floor master suite and spacious front entry. Upper level is a second full master suite complete with balcony and private sitting area. The lower level affords great privacy for family/guests - spacious bedroom/sitting/family room with two sliders out to patio taking in the meadow and mountain views beyond. Third full bath, storage and cabinetry abound. Winden Hill community features pool, tennis/pickle ball and close proximity to Lenox village.


4 Photos
BARNBROOK REALTY, INC.
10 Westdale Rd
Berkshire - South
Stockbridge > MA > 01262
$695,000
3 BD | 2 BA
Residential - Single Family

The epitome of single level living. There are no steps to get in to this gorgeous brand new home. The home was designed for anyone, however it does have features that would make it possible to stay in the home longer as one grows older. Doorways are wider as well. Open floor plan with hardwood floors and beautiful fixtures. Centrally located and easy to get to the Masspike or the New York State Thruway. Tanglewood is a five minute drive away!


20 Photos
WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY
4 Castle Hill Rd
Berkshire - South
Stockbridge > MA > 01262
$695,000
5 BD | 4 BA
Residential - Single Family

Perched above the Housatonic River on 8.9 acres, find quietude and serenity in this beautiful contemporary Stockbridge home. Minutes from Tanglewood, this home speaks to lovers of art, music, and nature. A sense of space, simplicity, and style define the interior, which features open living and dining areas, fabulous fireplaces, picture windows, and a superb master bedroom with sparkling en suite bath. From the living area, step into a stunning screened porch with radiant floor heating and hear the sounds of the river below. An interior spiral staircase leads to guest quarters, a rec room, and an office. Exquisite grounds feature a pool, hot tub, rock garden, grassy lawn, and perennial gardens. In the same family for 40 years - a rare opportunity in the heart of the Berkshires.


32 Photos
LANCE VERMEULEN RE, INC., LENOX
5 Dugway Rd
Berkshire - South
Stockbridge > MA > 01262
$698,000
4 BD | 4 BA
Residential - Single Family

Built in 2002, this beautiful contemporary home located on a quiet country lane in Stockbridge is ready for you to enjoy. Enter the foyer, hang up your coat and settle in. Relax by the fire in the beautiful great room with cathedral ceiling and beautiful two-story stone-clad chimney. When it's cold out, drive into your attached garage and enter through the kitchen with your groceries. Just behind the fireplace is the master bedroom suite with a lovely bathroom including double sinks, a large jet tub and tiled shower with dual shower heads. There's plenty of room for family and friends upstairs with three bedrooms, two full baths and ample closet and storage space. Utilities are located in the garage and easily accessible. Close to everything Berkshire... This is a must see property!


27 Photos
BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY
38A Glendale Rd
Berkshire - South
Stockbridge > MA > 01262
$699,000
4 BD | 3 BA
Residential - Single Family

Custom built home ''2017'' in the town of Stockbridge. Sits high up to enjoy mountain views. State of the art high efficiency heating cooling system. 4 bedroom 3 bath spectacular home. Open kitchen dining living room. Gorgeous wood floors, French doors, tiled bathrooms, Laundry/mudroom, and a Master bedroom suite. House can be sold furnished. Move right in .Has an amazing $80k rental income per year.


23 Photos
COHEN & WHITE ASSOCIATES
28 Lake Dr
Berkshire - South
Stockbridge > MA > 01262
$775,000
3 BD | 2 BA
Residential - Single Family

STOCKBRIDGE....Live in this unique modernized country style log house, located with a direct access dock on the Stockbridge Bowl outlet. Huge picture windows in most rooms frame woods and water views. This delightful year-round home with a 2 sided open fireplace, has a spacious country kitchen featuring a BBQ grill set in the fireplace and a large kitchen for family dining, plus 3 bedrooms and a 4th bedroom/office. Close to Tanglewood, ski areas, and Lenox, with bike and hike areas nearby.Come see the house of your dreams. Come see Shangri Log


40 Photos
ROBERTS & ASSOC. REALTY, INC
2 Laurel Ln
Berkshire - South
Stockbridge > MA > 01262
$799,000
5 BD | 6 BA
Residential - Single Family

One of a kind opportunity in Stockbridge!! This gracious colonial features 3800+ sq ft. Integrated living spaces work nicely for entertaining with formal living, dining, parlor and a large country kitchen. Fueled with natural gas. Accommodate family and guests with 5 BRs and 5.5 BAs; finished 3rd floor game room. Take in this .69 acre property from the large screened porch - rare to a village home. A private tranquil site with a easy stroll into town and abuts town trails leading to Ice Glen and Laura's Tower.


28 Photos
WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY
29 Mahkeenac Rd
Berkshire - South
Stockbridge > MA > 01262
$875,000
3 BD | 3 BA
Residential - Single Family

Stunning 3BR contemporary located in desirable Mahkeenac Terrace Stockbridge Bowl lake community. Deeded lake & boat access. Huge master suite, spacious great room with cathedral ceiling and loads of sunlight, 3 gas fireplaces. Large backyard w/ in-ground exercise pool, patio w/ built-in bbq. Less than 5 minutes to Tanglewood & close to the Berkshires' best cultural & recreational attractions. The ultimate year round country home. Don't miss this lake-living gem!


30 Photos
BERKSHIRE PROPERTY AGENTS
4 Cove Ln
Berkshire - South
Stockbridge > MA > 01262
$995,000
3 BD | 1 BA
Residential - Single Family

A once in a lifetime opportunity to own a slice of paradise. Privately situated on a peninsula in the heart of Beachwood on the Stockbridge Bowl boasting a stunning 90 feet of lake frontage and dock. Unobstructed sunrise and sunset views over the water. The rustic cabin dates from 1939 and has a double volume living/dining room graced by a charming stone fireplace and views of the garden and the lake. Bonus enclosed sitting room/study off the living room. The cabin has been updated with modern amenities such as a custom Blue Star Prof. range, and split-system air-conditioning/heating. 3 bedrooms and 1 bathroom. Sensitively landscaped easy-to-maintain garden with River Birch and Black Walnut trees and 2 separate stone patio dining areas. Outdoor shower. Pontoon. Sold As Is.


38 Photos
WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY
1 South Hill Rd
Berkshire - South
Stockbridge > MA > 01262
$995,000
5 BD | 4 BA
Residential - Single Family

LONGVIEW FARM..Over the new bridge and down a town maintained dead end road sits this early Historic Colonial home situated on 12.5 sub dividable acres. A former Stagecoach stop for the Hartford to Albany route this gem offers original hardware, ''document safe'', dining room with brick fireplace and oven to heat your fresh bread! This home has been lovingly maintained and updated. A perfect blend of the old and new! A spacious home. The keeping room with brick fireplace surrounded by wide wood panels. Updated kitchen, 5 bedrooms and 3.5 baths separated on two floors. Conservatory with glass walls and radiant heated floors is located steps from the kitchen. Amenities include an attached garage, rocking chair porch, guest house with loft, living room, full bath, tack room.

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