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33 Photos
ELYSE HARNEY REAL ESTATE
$1,875,000
5 BD | 5 BA
Residential - Single Family

PRIVACY AND POOLSIDE SPLENDOR IN THE BERKSHIRESTucked away in desirable Egremont, quality and attention to detail are evident throughout this beautifully cared for home. Designed for comfort, entertaining, or hosting family and friends, and ideally suited with the peace and quiet necessary for working remotely, this home is a perfect retreat. Filled with light, it features a warm, well appointed kitchen that invites you to ''gather here'', a cheerful sun room, 4 wood burning fireplaces, and a huge primary bedroom suite with a balcony and bow window sitting area. 4 additional bedrooms (3 on the first floor), the gracious living room, and a private library/office offer all of the versatility you will need.


23 Photos
LANDVEST, INC.

The ultimate family and friends compound with 23 rooms, 11 bedrooms, and 8 baths in 2 houses connected by a 2nd floor porch. The main house was built in the grand gilded age style in 1890 and the second attached home followed in similar style in 1900. Well maintained period details are enhanced by newer mechanicals, fresh paint, and new roofs. The two massive barns with new metal roofs are complemented by an icehouse, garden house, and caretaker home.The views are long range and pastoral overlooking the pastures, stream, and south pond.3rd floor ready to be finished. The Cassilis Farm Estate offers magnificent homes on a 20-acre beautiful setting less than 10 miles to Great Barrington.


54 Photos
LANCE VERMEULEN RE, INC
$1,995,000
19 BD | 20 BA
Residential - Single Family

The beautiful & historic Windflower Inn, is a terrific business or lifestyle opportunity. Built in 1850 & meticulously maintained, this rambling colonial with 13 en-suite guest rooms, several with in-room fireplaces, is a top-rated property on Trip Advisor. The first floor consists of two living rooms & a dining room - all with large fireplaces. The ground-floor accommodations also feature private access to a beautiful wrap-around porch. The screened porch overlooks a small pond & gardens. The 10+ acres includes four perennial gardens, mature blooming trees, & firepit, & meanders to celebrated ''Trolly Trail'' for walks, cross-country skiing & snowshoeing. A fabulous chicken coop provides fresh eggs for guests. Restaurant kitchen includes a double Garland commercial stove, commercial


49 Photos
LANCE VERMEULEN RE, INC

The beautiful & historic Windflower Inn is a terrific business or lifestyle opportunity. Built in 1850 & meticulously maintained, this rambling colonial with 13 en-suite guest rooms, several with in-room fireplaces, is a top-rated property on Trip Advisor. The first floor consists of two living rooms & a dining room -- all with large fireplaces. The ground-floor accommodations also feature private access to a beautiful wrap-around porch. The screened porch overlooks a small pond & gardens. The 10+ acres includes 4 perennial gardens, mature blooming trees, & firepit, & meanders to celebrated ''Trolly Trail'' for walks, cross-country skiing & snowshoeing. A fabulous chicken coop provides fresh eggs for guests. Restaurant kitchen includes a double Garland commercial stove, commercial


30 Photos
WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$2,065,000
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.


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


53 Photos
LANCE VERMEULEN RE, INC

This gorgeous and successful bed and breakfast offers a unique opportunity to live and work in the heart of Great Barrington. Each of the six exquisite suites features a sitting area, sleeping area and spacious bathroom. The 2-bedroom owner quarters are quite literally the ''coolest pad in town.'' The stunning living/dining/bar space overlooks the town. Commercial kitchen with stunning wall of red storage cabinetry. Mint condition. Elevator access. Laundry Room. Large office. Please see Detailed Property Notes under Documents tab. We look forward to telling and showing you more!


32 Photos
BERKSHIRE HATHAWAY HOMESERVICE BARNBROOK REALTY

This property is a great opportunity for any investor. Currently being run as a twenty-four lane bowling alley with a bar, an arcade, a food stand, a Uhaul center and a mini golf course. You could easily add eight more bowling lanes to this property. Centrally located in Great Barrington so it is easy to get to CT, NY, the Turnpike, and all of Berkshire County. There is so much upside to this property. There is parking for 89 cars and a very high traffic count daily. This is the price for both the real estate and the business.


89 Photos
WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY
$2,895,000
6 BD | 8 BA
Residential - Single Family

Recent $1m plus renovation on this private Green River Waterfront Property on pastoral 9+ acres. 6 ensuite bedrooms (4 in main house / 2 in carriage house), 2 half baths, exercise space with indoor Endless Pool, 4 car garage with workshop, 2 home offices and a hobby/art space. Radiant floors. Outdoor patios, beautiful screen porch, and private primary suite deck with awning. Lush gardens, rock walls, rolling lawn to the river with level areas for play. Outdoor shower. Incredible sunrises and wildlife viewing. Two story water side primary suite with separate closets. A charming and comfortable home for gatherings and entertaining. Significant income potential from Carriage House. F/O internet. Walk to 100 acre town park, trails, the village shop, GB & area attractions. See supplement.


62 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.


48 Photos
WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY
$3,800,000
4 BD | 5 BA
Residential - Single Family

NY architect Kenneth Nadler designed this custom built home on 43 acres ( 5.07 acres/38.46 acre lot). 4 bedrooms, 4.5 baths. Main level living room with fireplace (gas insert) double height window wall, raised panels, eat in kitchen with marble counters, oversized island. Kitchen opens to both screen porch and family room and close to the garage entrance and laundry room. A dining room, music/library, en suite bdr and a luxurious primary bedroom with a plethora of storage and spa like bath. Second floor offers, loft area used as game room, an additional ensuite bedroom and two additional bedrooms that share a Jack n Jill bath. Amenities include; Elevator, Inground Pool, Central Air, Buderus oil boiler, two car attached garage, stone patio's,, central vac, gleaming wood flooring.


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.


17 Photos
LANDVEST, INC.
$6,800,000
4 BD | 6 BA
Residential - Single Family

When the Interior Design Hall of Famers were commissioned to build a family compound in the beautiful Berkshires, they first started by getting acquainted with the land. Calvin Tsao and Zack McKown walked the many acres of open fields often to take in the magnificent views from all angles. The almost 18 acres was on the slope of the hill with the Berkshire hills in the distance and forefront. To capture the postcard panorama, they designed the 7000' house to follow the sun with angles and very large windows. The end result is a C configuration. The winding 1/2 mile drive is lined with a long allee of trees and mature landscaping leading to the house. Stone walls delineate the lawn from the woodlands. Views looking out to the Mountains are visible even at ground level.

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