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Multi-Million-Dollar Homes You’d Love to Own

A selection of properties currently on the Berkshire real estate market, ranging in price from $3 million to $6 million.


At the Top of the World in Connecticut
14 Weber Road
Sharon , Conn.

5 Beds/ 5 Baths/ 6154 sqft
$5,945,000
Offered by Elyse Harney Morris, Elyse Harney Real Estate, 860-318-5126

Privacy and all-encompassing, protected views surround this beautifully renovated 5 Bedroom home on 284+ acres. Oversized windows throughout invite and blend the tranquility of an unparalleled setting with superior craftsmanship.

Mexican Alder doors create a dramatic entry into the heart of the home. An exquisite Chef’s Kitchen sits central to the formal Dining Room, enclosed Bluestone Porch, and casual Breakfast area; creating a seamless flow for entertaining. The Library’s wood-burning fireplace and custom built-ins further warm the interior ambiance. A spacious Living Room, and spectacular Master Suite above, absorbs the serenity of the surrounding vistas. French Doors fill the back of this home with light and descend upon an expansive bluestone patio.

Landscaped gardens and stonework join the rear Patio to a gunite pool that sits at the crest of views overlooking the property’s 42-acre pond – reflecting the beauty of an unmatched panorama. A one of a kind setting blessed with all of Nature’s beauty in a home carefully detailed for comfort and serene living.

Timeless Berkshire Cottage
151 Walker Street
Lenox, Mass.

10 Beds/ 8 Baths/ 2 Half Baths/ 6934 sqft
$ 4,250,000
Offered by Dan Alden, William Pitt Sotheby’s International,413-335-9300

Thistlewood – A classic Berkshire Cottage that has been meticulously restored & updated for a modern lifestyle. Designed by noted Boston architects Rotch & Tilden, the main house offers classic proportions and elegant details throughout. The grounds wrap the house with stately gardens, pool & poolhouse.

The original carriage house has been reinvented as a 4 bedroom, 3 1/2 bathroom guest house with wood-panelled great room, entertainment bar, 2 ensuite first floor bedrooms and a second floor guest apartment. All finishes & systems are of the highest quality.

The property is within walking distance to Lenox village & Tanglewood, convenient to all Berkshire attractions & amentities and just 2.5 hours to NYC & Boston metro areas.

Waterfront Estate
1 Chanterwood Road
Lee, Mass.

5 Beds/ 5 ½ Baths/ 5600 sqft
$ 3,500,000
Offered by Chapin Fish, William Brockman Real Estate, 413-528-4859

1 CHANTERWOOD Rd, Lee, Massachusetts 01238 – CHANTERWOOD: STUNNING BERKSHIRE WATERFRONT ESTATE ON GOOSE POND-ONE OF NEW ENGLAND’S FINEST LAKES! 300′ of shoreline + private sandy beach, dock, privacy, & 12 acres divided into 3 parcels to allow for multiple homes. Renovated & expanded 5-6 bedroom lodge with the charm & quality of 100 years ago. Spectacular Great Room & state-of-the-art systems.

Retreat in Alford
50 East Road
Alford, Mass.

4 Beds/ 8 Baths/ 11,800 sqft
3,300,000
Offered by Keith Ross, Landvest, 978-544-5767

A meandering drive through a hardwood forest leads to this 11,800 sq ft family retreat in the Berkshires. The wood shingled home was built in 2003 on a ridge near the center of the quaint village of Alford. The home offers great privacy with sunset views, yet is only a 20 minute drive to Tanglewood and other cultural amenities offered in the area. A 2,400 sq ft studio and 800 sq ft pool cabana are next to the house

Queen Anne Style Lenox Cottage
106&114 Cliffwood Street
Lenox, Mass.

8 Beds/ 8 Baths/ 8,500 sqft
$4,750,000
Offered by Nancy K Kalodner, Cohen and White Associates, 413-446-1111

A pinnacle of the Gilded Age, this superb and luxurious Lenox ‘cottage’ is a gem! A sparkling example of the American Queen Anne Style at its finest, this 1883 original has been restored and reinvented, polished and preserved, for those who demand nothing less than elegance, comfort, and perfect beauty when returning to the place they call home.

La Montagna
278 Hillsdale Road
Egremont, MA

6 Beds/ 6 Baths/ 7075sqft
$ 6,150,000
Offered by Elyse Harney Morris, Elyse Harney Real Estate, 860-318-5126

Located at the apex between New York and Boston on 61 totally private acres with stunning 360 degree views. Views from every room in the house enhance its position. Spacious, light-filled rooms are perfect for entertaining. Six resplendent Bedrooms and 6 fully appointed Baths, Chef’s Kitchen, Breakfast Room, massive Living and Dining Rooms with egress to outdoor living, fireplace, easterly and westerly views. Three full floors of additional living space in a separate, private, Post and Beam Barn with expansive Studio, 2 Bedrooms, 2.5 Baths, soaring ceilings looking out to views, pool and secret garden. The in-ground pool between the house and barn offers a Greek Revival Temple pool house. This property is perfect as private retreat, corporate, spiritual or health retreat. The amenities nearby are skiing across the street at the Catamount ski area, golf at the Egremont Country Club, horseback riding choices, and a private airport.

Converted Historic Barn
65 Shun Toll Road
Egremont, Mass.

4 Beds/ 5 Baths/ 2 Half Baths/ 6600sqft
3,500,000
Offered by Chapin Fish, William Brockman Real Estate, 413-528-4859

65 Shun Toll Rd, Egremont, Massachusetts 01230 – Many dream of converting a historic barn into a country house. A barn tells a story, has a past, and the old beams, posts and boards have a patina and a magic which new construction can never recreate. This 26 acre estate is masterfully designed and crafted from two 18th & 19th century barns on one of the Berkshire’s finest country lanes in North Egremont. 65 Shun Toll Road embodies a rustic elegance that will simply captivate you as you gaze across the soaring, yet brilliantly intimate spaces and through the expanses of glass to the inspiring and extraordinary distant views of farmland below and mountains beyond. Offering nearly every luxury imaginable in its 6,600 square feet, yet in an ultimately comfortable and authentic manner – the perfect Berkshire country home.

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Ideally situated in the heart of downtown Stockbridge, and move-in ready

Elle Villetto and Jared Kelly of William Pitt Sotheby’s International Realty offer an 1860 colonial home, stylishly updated and move-in ready. See it now and be in before the summer!

A minimalist condo with maximum light

We often referred to this project as the “house of glass” because there is glass everywhere.

Berkshire region real estate sales

Weekly real estate transactions for Berkshire County in Massachusetts, Litchfield County in Connecticut, and Columbia County in New York.

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