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41 Photos
BERKSHIRE PROPERTY AGENTS, LLC
$1,975,000
5 BD | 6 BA
Residential - Single Family

HISTORIC EXPANSION - A 12.4 ACRE ESTATE YOU CAN MOVE RIGHT IN TO. Take the New England concept of original house, new house, back house, guest house, pool and barn- This 1780 Colonial has grown to reflect the needs of this owner's generational family. New additions include a first floor open flowing gourmet kitchen w/ two dishwashers, living-dining room, master suite, library, bathrooms, screened porch, laundry, new wood floors and windows, new roof, heating system & so much more. Original section has a dining room, front parlor, 3 upstairs bedrooms, 3 fireplaces, 2 bathrooms. The Guesthouse has 1 bedroom, 2 baths w/its own open living, porch and laundry. A huge 2 story barn w/ a garage and gym. The heated gunite pool is central to all the structures; pergola, patios and an outdoor shower


46 Photos
THE KINDERHOOK GROUP - PITTSFIELD
$2,100,000
4 BD | 4 BA
Residential - Single Family

Rare opportunity to own this private, 32-acre estate in the center of Alford. Built in 1875, the historic post-and-beam home was completely renovated by famed director Dick Schneider to create this spacious and comfortable country house perfect for relaxing with friends and family. The main part of the house features a light-filled, eat-in kitchen which leads out to the deck overlooking nature. The living room has a wood-burning fireplace and an adjacent den with attached full bath. Upstairs are 3 bedrooms including a large master suite. The breezeway off the downstairs atrium leads to a 2-car garage above which are located the guest quarters with full bath and which is also ideal for use as an office or home gym. The grounds are simply gorgeous, with the Alford Brook running through


27 Photos
WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$2,200,000
4 BD | 4 BA
Residential - Single Family

This meticulously renovated home on one of Great Barrington's most desirable roads is perfect for both a full-time home or weekends in the country. Traditional exterior but thoroughly moderized from top to bottom. Graciously sized rooms, high ceilings, large cook's kitchen, attention to every luxurious detail, this home has everything one needs for comfortable living. Three bedrooms, 2 1/2 baths. Separate apartment for staff or guests. Views in several directions.


59 Photos
WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY
$2,250,000
7 BD | 8 BA
Residential - Single Family

An iconic country estate nestled in the northern hills of Berkshire County. Boasting early 1900's classic craftsman style architecture yet fully renovated and modernized with gourmet kitchen and freshly redone, heated Gunite in ground pool. The main residence offers a master suite and 3 en suites on the second level while all entertaining spaces are on the ground level with access to patios and porches. Connected by your 3-season glass and screened nature-gallery, your guest house awaits. Multi level with workout space, office and 2 bedrooms / 2 full baths. Further guest accommodations are found above the detached garage blending a more contemporary 1 bedroom with living space and sizable full bath. Its rare to find almost 3 acres in such close proximity to all of Williamstown.


25 Photos
LANDVEST, INC.
$2,300,000
4 BD | 5 BA
Residential - Single Family

Windy Ridge Farm is an elegant country estate on 140 acres with views to Mt Greylock and the valley to the south. The location off a 1/4 mile long tree lined drive offers privacy in a bucolic setting, yet is only a 15 min drive to Williamstown, 8 minutes to Jiminy Peak, and 25minutes to Tanglewood.. There is so much to enjoy at home! The fabulous gunite pool with water fountain and surround sound, and the tennis court are favorites for the summer. The wine entertaining area is used for pre-dinner cocktails and dining is either seasonally in the 3-season gazebo with 360-degree views or the formal dining room with a roaring fire. The sunken living room with 20' ceiling, fireplace and balcony is ideal for entertaining. Open fields suitable for Agriculture, horse farm.


32 Photos
WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY
$2,500,000
5 BD | 7 BA
Residential - Single Family

Bright & Open Contemporary Home on 15+ acres. Open floor plan with easy flow from room to room. This 6,800 SF home owes it charm to the architectural details of homes in the Hamptons. Wooded setting with mountain & field views and Pool. Last house on a shared drive. Five Bedrooms with en suite baths, including 1st and 2nd floor master suites. Great room with chef's kitchen, dining area and living room. Library, formal dining room & computer room/office on first floor. Pantry and Bar area. Fitness/Playroom. Home Theatre on lower level. Craftsman finishes throughout. New Gunite Pool with expansive stone patios, established perennial gardens & mahogany front porch. Custom stone fire pit. Oversized 2 car+ garage. Convenient to the Taconic Parkway and downtown Great Barrington. Agent owned.


48 Photos
WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY
$2,600,000
5 BD | 4 BA
Residential - Single Family

Shadowbrook: This breathtakingly beautiful European-style estate has been completely updated, renovated, and enhanced to be the ideal country retreat. Comprising 29 very private, secluded acres, its centerpiece is a gorgeous 5BR mansion, set amidst lush landscaping, stone patio and walls, Normandy barn, gunite swimming pool, paddock with run-in, chateau de poulet, field, stream, woods, and secret chanterelle grove. Exquisite taste, meticulous workmanship and attention to detail are evident throughout, in the seamless matching of original Philippine mahogany woodwork, the elegant staircase, new roofs, windows, systems, kitchen, and baths. Seasonal mountain views; possible higher vantage point on the property; abutting conservation land; close to town and amenities. Furnishings available.


33 Photos
STONE HOUSE PROPERTIES, LLC
$2,750,000
16 BD | 17 BA
Residential - Single Family

The Garden Gables, located in the center of Lenox on over 4 very private park-like acres with gardens, patios, mature trees and a heated 70' pool, can be the ultimate family compound. Beautifully furnished and tastefully decorated with 16 unique bedrooms all with updated private baths, several with fireplaces and all fully air conditioned.The historic 1780 main building and attached Eladesor Cottage includes 12 spacious suites. The separate Orchard Cottage includes 4 ensuite rooms with separate entrances, cathedral ceilings and fireplaces.There are also 2 charming dining areas in the main building in addition to the library/music room and cozy ''sherry room'' both with fireplaces.The kitchen is equipped with updated appliances. An extraordinary opportunity!


63 Photos
LANCE VERMEULEN RE, INC
$2,995,000
5 BD | 5 BA
Residential - Single Family

Custom-built five-bedroom Timbercraft home on 8+ acres. Private tennis/basketball court, in-ground Gunite heated pool. Pennsylvania Stone and cedar shake exterior, three-sided fireplace and Timberframe truss ceiling in great room. Large state-of-the-art kitchen and breakfast nook tower. Plenty of deck areas to enjoy the outdoors. Lower level equipped with workout room, sauna and plenty of room for games. First-floor bedroom suite with full bath and gas fireplace. High-speed internet allows you to work remotely, and a large studio space above the garage make it perfect for private office or guest quarters. Don't miss out on this opportunity to have your own retreat in the Berkshires.


52 Photos
BERKSHIRE PROPERTY AGENTS, LLC
$3,100,000
5 BD | 6 BA
Residential - Single Family

Cookledge, is a sprawling contemporary compound spread over mountain top glacial outcroppings, with awe-inspiring views south over Connecticut and west to the Taconic Range. Nearby the Southfield Store Cafe, drive up the long romantic winding drive to this sensitively sited and quality built home with huge windows and glass doors that draws one outside from almost every room to the truly stunning views. Large airy rooms with high ceilings, tall doorways, hardwood floors, multiple fireplaces, along with separate master and guest bedroom wings, all with ensuite baths, flow easily throughout the main house. The heated three-car garage has a Tesla charger and a guest or caretaker apartment above, with a fireplace and deck. Total seclusion, trails to a stream gorge, and magnificent serenity.


22 Photos
WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY
$3,500,000
5 BD | 8 BA
Residential - Single Family

This outstanding private and spacious estate is set on 12.1 beautifully landscaped acres offering just over 14,000 square feet of quality living area. The unique 4 Bedroom, 5 full bath/3 half bath main house includes an in-law guest quarters and an Olympic sized indoor/heated, pool. Top grade appliances are another important feature. Dark walnut hardwood flooring runs throughout the main house as does a state-of-the-art radiant heating system. Other special features include Vantage Lighting, an indoor/outdoor intercom system, a security system, a large game room and home office, a steam shower and overflow tub in the master bath, a humidification system, and a full house commercial generator. The horse barn also includes in-law guest quarters as well as a fireproof walk-in vault.


65 Photos
LANCE VERMEULEN RE, INC
$3,750,000
5 BD | 6 BA
Residential - Single Family

Surrounded by magnificent pastoral views over protected land, this historic home is a gem. Once part of the adjacent farm, then home to an opera diva, it has been transformed into a wonderful, light-filled sanctuary with a clean, simple aesthetic. Antique character has been highlighted, modern conveniences added, and high-efficiency updates made. Each room is delightful. The sleek eat-in chef's kitchen with access to deck and screened porch. The dining room with antique fireplace, custom bar and wall of built-in shelving. The extraordinary great room, once a barn, now a dramatic space with a fireplace at one end, and spectacular view window on the other. The primary bedroom suite with exquisite bathroom & dressing room. The gracious first floor guest suite with sweet ceiling detail...


56 Photos
COHEN & WHITE ASSOCIATES
$3,895,000
5 BD | 8 BA
Residential - Single Family

The Birches.......welcome to your new oasis in the Berkshires where every season is memorable. This magical family compound has all the modern amenities a buyer wants to live, play, relax and work from, surrounded by twenty plus acres of privacy and far reaching views in all directions. Architecturally redesigned and renovated using the finest materials this stunning contemporary has big open common areas for gathering, first floor master en suite, guest bedrooms en suite and a private two bedroom guest quarters with kitchenette, all offering plenty of space for a large crowd or intimacy for a few. Just arrive with your suitcase and enjoy all this impeccably maintained estate has to offer; beautiful gunite heated pool with waterfall surrounded by expansive stone patio


50 Photos
WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY, LENOX
$4,600,000
7 BD | 8 BA
Residential - Single Family

Options abound for a lifestyle change at what is now known as The Inn at Richmond and The Berkshire Equestrian Center. This magnificent 27 acre property includes a charming Colonial era 7 bedroom inn, 5 cottages, 2 event barns, 1 Shaker horse barn, 26 horse stalls, 15 grazing paddocks, a 16,000 sf multi-purpose heated indoor arena with offices and a two bed apartment with spa, 1 outdoor arena, and the possibility to develop three building lots. With its casual elegance and charm, this Colonial equestrian estate will allow your long held passion to blossom whether you use the property as a stunning family compound, an event destination, and/or a first class equestrian facility. The prime central Berkshire County location will graciously support your new found lifestyle,


29 Photos
WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$4,900,000
4 BD | 4 BA
Residential - Single Family

A rare estate offering in the Berkshires. Breathtaking southern and western views from this historically important Great Barrington estate. Designed by Charles Platt for Charles Freer of the renowned Freer Gallery in DC, and constructed of stone quarried from the property, this one floor layout was well ahead of its time.The main house has a large, comfortable living room with views from massive windows, a library, a gracious dining room, all with fireplaces. The property encompasses a stable and riding ring, pool, orchard, vineyard and two fully equipped guest houses and a caretaker's home. This is a rare opportunity to own a unique nearly 50 acre estate with magnificent views - all close to Great Barrington.

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