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19 Photos
ROBERTS & ASSOC. REALTY, INC
$474,500
2 BD | 3 BA
Residential - Condo/Townhouse

Winden Hill features panoramic westerly views. Take in the sunsets and views of Lily Pond from your private deck. Two bedrooms-each with private bath, den with French doors serves as a bonus sleeping space. Central a/c, natural gas heat, and fireplace. Condo community features pool, tennis/pickleball court and is close to Lenox center, Shakespeare, Tanglewood and Kripalu!


20 Photos
WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY
$475,000
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.


16 Photos
STONE HOUSE PROPERTIES, LLC
$479,000
4 BD | 3 BA
Residential - Single Family

Minutes to Tanglewood, this mid-century contemporary offers a peaceful haven. Set well off the road, the house is gently nestled in the landscape amidst, sunny and private gardens. Gorgeous wide plank floors throughout the first floor. Beautiful craftsman built-ins in the dining room and first floor office / sitting room. High-ceilinged and bright 2nd floor bedroom/office. New septic system 2019 for 5 bedrooms - each current office are possible bedrooms. Plus whole house generator and two sheds for storage.Enter through the charming screened porch to an elegant foyer where the living room, kitchen / dining room, sitting room and first floor master suite are located. A sunlit staircase leads to the second floor offering three bedrooms and a 3/4 bath and storage.


33 Photos
ROBERTS & ASSOC. REALTY, INC
$489,000
3 BD | 2 BA
Residential - Single Family

Sited at the end of a quiet cul-de-sac this move-in ready contemporary cape is a must-see! Open plan with fireplaced living, dining that opens to large rear deck, and an updated kitchen. There is a first floor bedroom and full bath and laundry. Second floor features two additional bedrooms, full bath and open loft area. This very private sanctuary of 3.5 acres (fully passing Title V!) includes an attached garage, large storage shed and a welcoming circular drive surrounded by perennial gardens. Compare for value and convenience! Less than ten minutes to Tanglewood and Stockbridge Bowl!


39 Photos
STONE HOUSE PROPERTIES, LLC
$498,000
4 BD | 2 BA
Residential - Single Family

A beautifully maintained Federal home, located on Yale Hill in Stockbridge and within walking distance to the village. Light and bright, this home has two screened porches, an eat-in kitchen, dining room, living room and library providing ample space for home gatherings. The second floor has 4 bedrooms and a large attic provides more storage for this surprisingly large home. Located on the east side of the road, next to the Kampoosa, with a tidy landscaped yard, mature gardens, flat lawn and a seating area by the brook taking in the magic of the rapids. The barn is spacious and ideal for the hobbyist or artist and can provide a great venue for fair-weather entertaining. Over the years, this home has had updates to the mechanical systems, kitchen and baths. (see supplement)


8 Photos
BERKSHIRE PROPERTY AGENTS

THE LEDGES parcel is located on a naturally occurring terrace along the westerly ridge of Campion Farms. The lot is edged on the west by a long wooded bluff, rising dramatically up to the ridge. Views unfold to the east and the south across the Berkshire Mountains.Campion Farms is located within the historic township of Stockbridge, Massachusetts. The rural setting offers a stunning natural landscape with over 30 conservation acres. Within minutes of the Berkshires premier cultural and outdoor attractions.


43 Photos
COHEN & WHITE ASSOCIATES
$549,000
4 BD | 4 BA
Residential - Single Family

Perched beautifully high with lovely west/southerly views this meticulously maintained 4-bedroom, 4 bath; 2 first floor master ensuite bedrooms, one with a private entrance to deck. This Stockbridge home is a gardener's, wildlife & birders delight! Come see & love this special home!


54 Photos
THE KINDERHOOK GROUP - PITTSFIELD
$569,000
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


46 Photos
WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY
$575,000
3 BD | 3 BA
Residential - Single Family

It's all about location! Stockbridge home on 4 acres on a quiet dead end street. This 1990's home has been meticulously maintained and updated in 2003. A spacious floor plan includes an L shaped living room with fireplace, open kitchen with family space for dining or entertaining, full bath. Enjoy the screen porch for summer days. The light filled dining room is spacious and could be used as a den or main floor bedroom. Second floor offers two guest bedrooms and full bath, over-sized European master en-suite. Company coming? We have just the spot for them in a charming studio apartment or rent year round via VRBO or Air B&B for extra income! A perfect full time or second home minutes to Tanglewood, Shakespeare and Company and Kripala. The two car garage completes this package.


35 Photos
STONE HOUSE PROPERTIES, LLC
$575,000
4 BD | 3 BA
Residential - Single Family

Total seclusion, scant minutes from Tanglewood, and a beautiful town beach for swimming and kayaking. Quiet and completely private country living at it's best, a rare-to-find in Stockbridge.There is wildlife abound, wild turkeys crossing the yard, owls hooting in the big oak tree and acreage to hike in the woods. Watching birds flock to the feeder in winter. Cardinals, sparrows, finches to list a few.With 2,240 square feet, this Colonial home boasts bright and natural lighting, every window looking out to beautiful greenery, and a seasonal water view of Stockbridge Bowl. Oversized and insulated 2-car garage with high ceilings and 2nd level storage for all your summer and winter toys!This home will fit all your needs all year round!


21 Photos
WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY
$598,000
3 BD | 3 BA
Residential - Single Family

NEW REDUCED PRICE! Live in true Berkshires splendor with magnificent mountain views! This contemporary 3 bedroom has it all. Open floor plan with loads of sunlight, gourmet kitchen &large deck for entertaining. Level property with tranquil meadows. Ideally located very close to Tanglewood & Stockbridge Bowl town beach. Very close to vibrant downtown Lenox & so many of the Berkshires' world class cultural attractions. Don't miss this gem!


46 Photos
BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY
$625,000
4 BD | 4 BA
Residential - Single Family

Beautiful, Spacious & Immaculate Stockbridge home on nearly 2 landscaped acres with distant mountain views. Offering a spacious Open Plan Living space with Fireplace, Central A/C, 4 Bedrooms, 4 Full Baths, Gourmet Kitchen plus the Separate Private Suite with private entry, full basement with Washer & Dryer and the oversized 2-car garage, both with high ceilings. There is also a beautiful, architect designed Screened-in Porch and the charming Antique Barn/Stable with a private driveway. Located in the desirable Glendale section of Stockbridge, served by Public Utilities, within an easy distance from Tanglewood, swimming & boating on Stockbridge Bowl, Shopping, Restaurants, Galleries & from all Berkshire activities..Price has just been Reduced. Please View ''Virtual Tour''


26 Photos
COHEN & WHITE ASSOCIATES
$685,000
4 BD | 4 BA
Residential - Condo/Townhouse

Rare White Pines Brookside Villa ready for your enjoyment with Har Tru tennis courts, clubhouse, exercise room, indoor pool and private association beachfront on the Stockbridge Bowl for swimming and boating. Wonderful open common spaces...Great Room with fireplace open to dining and kitchen with direct access to a generous screened porch. Main level master bedroom en suite, three guest bedrooms, family room, spacious decking and an attached one car garage. Very private end unit on a dead end drive....WALK TO TANGLEWOOD!!


32 Photos
LANCE VERMEULEN RE, INC., LENOX
$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!


37 Photos
ROBERTS & ASSOC. REALTY, INC
$774,900
5 BD | 6 BA
Residential - Single Family

Warm and welcoming historic Colonial featuring 3800+ sq. ft. in the center of Stockbridge. This grand yet cozy home offers plenty of space for gracious entertaining with a formal living room, dining room, parlor and a large eat-in country kitchen. Accommodate family and friends with 5 generous bedrooms and 5.5 bathrooms. Finished third floor with a game/media room as well as plenty of storage and a bonus room. Enjoy the extensive lawn and outdoor space from the large screened in porch - rare to a village home. A private tranquil site with an easy stroll into town and abutting protected properties with maintained nature trails. Fueled by natural gas with many recent improvements including new roof and exterior paint. This is a must see property!!


8 Photos
WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY
$798,000
9 BD | 7 BA
Multi-Family

Outstanding opportunity to own a fully rented 5-unit multifamily rental property in the heart of downtown Stockbridge. Electric is submetered. New boiler installed 4 years ago. Pre-painted siding means no need to paint exterior. Ideally located - walk to everything! Only 1 block from post office, library, restaurants, shopping & Red Lion Inn. Building is also across the street from Stockbridge Town Park & Housatonic River and great hiking trails are right down the block. For financials, please call listing agent.


48 Photos
LANCE VERMEULEN RE, INC
$895,000
5 BD | 3 BA
Residential - Single Family

1780's colonial on beautiful property. 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.


35 Photos
STONE HOUSE PROPERTIES, LLC
$895,000
4 BD | 4 BA
Residential - Single Family

Set on 6 beautiful acres this Mike Shiels built home bathed in sunlight and absolutely private. Tasteful finishes and a great floorpan - one floor living for one or two people with the remaining bedrooms (each with private bath) on the lower lever. Large guest suite is substantially separate from the rest of the house. Large kitchen opens to the deck. Set on 6.65 acres with an additional 20 subdividable acres available. Perfectly located central to all the venues that make the Berkshires great.


38 Photos
STONE HOUSE PROPERTIES, LLC
$949,000
3 BD | 4 BA
Residential - Single Family

Big Views, Privately Sited, and Dramatic Sunsets. It's easy to enjoy the beautiful approach on scenic Ice Glen Road to this nicely maintained home. The floor plan is open and comfortable and allows for one level living and most rooms enjoy the spectacular western views. Gourmet kitchen with high end appliances, including a Wolf cooktop and Bosch oven and dishwasher. Spacious living/dining with gas fireplace and sliding doors to the deck which overlooks the swimming pool and landscaped grounds and takes in the big views. A lovely, spacious solarium, which also opens to the deck is a wonderful room to enjoy all seasons. The lower level is finished with 2 bedrooms, yoga/exercise room/kitchenette and an easy walk out to the grounds. Great location, mid-way between Great Barrington and Lenox!


4 Photos
HELEN MULLANY REAL ESTATE, LLC
$1,149,000
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 nice out door spaces for the residents, and all a short walk to everything the town offers. Perfect for an investor owner occupier.

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