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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


40 Photos
BURNHAM GOLD REAL ESTATE, LLC
$1,985,000
6 BD | 4 BA
Residential - Single Family

This 38-acre property - with a handsome, modern take on the American Farmhouse, sited on a hillside with landscaped lawns, hayfield and a pond - offers some of the finest views in Berkshire County. The pastoral setting is private, secluded and peaceful, and the house was laid out to offer a panoramic view of the Taconic Range, and a special focus on the majestic Mount Greylock - a mountain that has inspired artists and authors like Melville and Thoreau, with its ridges, notches and unique cirque changing hues throughout the day, in every season.


57 Photos
THE KINDERHOOK GROUP - PITTSFIELD
$1,995,000
4 BD | 4 BA
Residential - Single Family

''High Meadows'' is a grand and luxurious 20 acre estate with spectacular sweeping views of October Mountain. Set high upon a private knoll, the chic and newly renovated 4 bedroom contemporary home features a towering sun filled great room, wine cellar, 3 fieldstone fireplaces and new outdoor bar/kitchen to mention just a few.There are meticulous specimen landscaping with master gardens, pear and apple orchards, groomed walking trails and perhaps best of all, not only a lovely gunite pool/spa area, but an extraordinary crystal clear swimming and trout pond! This is an ideal home and property for ENTERTAINING friends and family! Call for a private tour.


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.


43 Photos
COHEN & WHITE ASSOCIATES
$2,650,000
4 BD | 5 BA
Residential - Single Family

Nestled within 27+ private acres, this custom designed and built home and its expansive gardens have been lovingly created with an artistic sensibility to embrace and enhance the beauty of this exemplary Berkshire home and its peaceful and magical landscaped setting. Crafted with only the finest materials, and meticulously maintained, this gracious property both welcomes and reflects stunning distant views in all seasons through the carefully positioned windows that welcome the outside, in. Outdoors, there is a vista from every turn of the garden paths; across warm fieldstone patios and wide sloping lawns; the play of dappled light on the surface of the natural pond-like swimming pool. In short, a family home where careful and artistic employ of space, coordinated color and lands


55 Photos
WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY
$2,750,000
5 BD | 4 BA
Residential - Single Family

The Historic Ashley Falls Mill built in 1737. Inviting and dramatic renovation with contemporary floor plan. The Mill sits suspended above the water and features two waterfalls, two lush islands and a large swimming pond. Beautiful details including original hand-hewn beams, reclaimed marble, soaring ceilings and luxury finishes. Finished studio space above two car garage. Meticulously landscaped with masonry and multiple outdoor vignettes. Incredible light and the soothing sound of water make this a unique retreat. Features 5 Bedrooms and 4 Full Baths.


33 Photos
WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY
$2,850,000
5 BD | 5 BA
Residential - Single Family

SPECTACULAR HOME WITH UNBELIEVABLE VIEWS! Extraordinary attention to detail and outstanding quality throughout this terrific open floor plan home. The 2 story sunken LR features a significant fireplace flanked by large captivating windows showing off 100 mile views across state lines. The state-of-the-art kitchen is any cook's dream come true.The spacious dining area provides guests the opportunity to enjoy this home's exciting interior and exterior features. Just when you think you have seen it all, enter the 1st floor Master Suite. How ''sweet'' it is with a two sided fireplace to add extra warmth to both the bedroom and the bath. On the way out of this remarkable bathroom, be sure to notice the dressing room with its special features and countless built-ins. MORE


15 Photos
LENOX CANYON REALTY
$2,875,000
6 BD | 6 BA
Residential - Single Family

Exquisite in every detail, this home graces more than an acre of prime Berkshire property! In a league of it's own as part of the Pinecroft subdivsion of Canyon Ranch, this luxurious haven offers the option of membership to the world class health and wellness facility. A gourmet kitchen, fireplaced living room with wet bar and gracious dining room welcome you home!Numerous exceptional amenities abound including an eight seat hi-def movie theater, climate controlled wine cellar, sauna and soda fountain. Other features include a heated three car garage, heated gunite pool with spa and a fully equipped outdoor kitchen in the pool house!


40 Photos
WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$2,900,000
5 BD | 5 BA
Residential - Single Family

This spectacular 5 bedroom, 4 1/2 bath post & beam home perched on a 10+ acre mountain ridge instantly welcomes you with a beautiful outdoor pool & hot tub overlooking breathtaking views. The primary bedroom, en-suite bath with spa amenities & walk-in closet is located on the main level, along with a chef's kitchen, large island with marble counters & dining room which opens into the great room with a wood burning fireplace. The second floor includes an en-suite bedroom, office & two additional bedrooms sharing a jack & jill bath. The lower level features a walk-out to the stone patio, pool & hot tub areas & includes a bedroom with full bath, game room & TV room with a wood burning fireplace. This is a geo-thermal energy-efficient home with radiant floors in the primary bath & lower level.


23 Photos
SCOT COHEN REALTY
$2,995,000
3 BD | 5 BA
Residential - Single Family

Expansive views from every window - Taconic Range and the Bash Bish Gap to the east & Stissing Mountain to the south. Floor to ceiling windows in main living area. Custom cabinetry throughout. 3 bedrooms. 4.5 baths. Sleeping loft. Large office with full bath (could be guest suite). Sauna. Movie theatre. Large gym/playroom with full bath. Heated, in-ground pool. Firepit. Extensive decking & covered porch. Fenced yard with fruit trees. 2 car attached garage. 13.92 acres.


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.


77 Photos
STONE HOUSE PROPERTIES, LLC
$3,350,000
3 BD | 4 BA
Residential - Single Family

Nature becomes art when framed by walls of glass in this one-level minimalist masterpiece. Flawless transition from interior living space to the spectacular outdoors with breathtaking mountain views. Elegance and sophistication throughout in the clean modern lines and consistent palette of materials and fixtures. Designed by the award winning and internationally acclaimed Res4 architects using systematic design methodology leveraging existing prefabrication methods to produce custom modern homes (see ''more''). Open kitchen living with custom cabinetry and Stuv fireplace. Media room with retractable screen and surround sound. Two versatile guest bedrooms with custom Murphy beds allowing easy transition to office space. Interior courtyard with Wolf outdoor grill. Heated screened in porch.


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


66 Photos
COHEN & WHITE ASSOCIATES
$4,850,000
5 BD | 8 BA
Residential - Single Family

CASA TRAMONTI.....House of the sunset...life's reminder that whatever happens every day can end beautifully, says it all for this sophisticated Contemporary, built by one of Berkshire's premier builders. Offered for the first time, it has the necessary amenities of Broadband fiber optic & great cell phone service. From the approach this home captures stunning westerly views to the Catskills, keeping the viewer mesmerized with walls of glass. The sleek & sophisticated design of a most comfortable and ''livable'' space features open common living, decking for 80*, 5 br's en suite, an amazing sunroom & screened porch with waterfall sounds. A home theatre, gym & specimen plantings, organic vegetable garden, a multiple fruit orchard & fire pit to gather around.....reason to never leave home!!


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 reknowned 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.


31 Photos
COMPASS CONNECTICUT, LLC
$5,900,000
13 BD | 11 BA
Residential - Single Family

Set on 31 acres overlooking two mountain ridges, this 26 room, 11,700+ sq. ft. stately English Manor home is one-of-a-kind in so many ways. Generously proportioned and graceful rooms with exceptional architectural details throughout such as exquisite moldings & period marble carved fireplaces. First floor includes an elegant living room, library paneled in rare Purpleheart wood from the Amazon rainforest, banquet sized dining room, family room with original faux bois panelling, cocktails room, cooks kitchen, breakfast room, catering kitchen & staff office. 7 principal bedroom suites, most with fireplaces & private baths. 6 additional bedrooms. perfect for offices, etc. Third floor is generous with several rooms for fun, play or fitness. 2 berm guest house on separate parcel.


50 Photos
ELYSE HARNEY REAL ESTATE
$17,950,000
9 BD | 14 BA
Residential - Single Family

Meticulously designed by Acheson Doyle Partners, beautifully landscaped and finished with the finest materials, the 9-bedroom main house is on more than 470 pristine acres and boasts unparalleled western views of the Berkshire Mountain Range. The entrance hall, with a grand staircase, opens to a dramatic 39-foot-long formal dining space with a soaring 32-foot-tall (3 story) glass atrium ceiling. Several living spaces on the main floor including a light-filled 47-foot great room, a handsome library as well as a spacious living room compliment an exceptionally appointed designer quality chef's kitchen with a large butler's pantry. The property also includes an expansive Outdoor Pool, a Spa (seats 15), Tennis Court, a Barn, a Warehouse, and Art Storage Building, and a rustic log cabin.

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