This is the one you've been waiting for. A classic mid-century home on over 4 private acres, offering the ultimate Berkshire lifestyle. The bright, open-mid century floor plan provides a seamless flow, while two fireplaces add classic comfort. The home features 4 bedrooms, 3 baths, large office and a media room, offering flexibility for family and guests. Outside, your private resort awaits. A beautiful heated swimming pool and a dedicated tennis court provide endless recreation. The expansive grounds, located at the end of a quiet road, guarantee unmatched privacy. Plus, a large solar array and new heating system drastically cuts utility costs. Enjoy total seclusion while being in the middle of everything that makes Great Barrington one of the most desirable towns in the Berkshires.

FOR SALE: Prime Downtown Great Barrington Gem - Endless Possibilities! Welcome to 406 Main Street, a rare opportunity in the heart of downtown Great Barrington, MA. Just steps from bustling Main Street shops and restaurants, this versatile 5,180 sq ft building offers exceptional potential for residential, commercial, or creative mixed-use transformation. Zoned B2, the property allows for single-family, multi-unit, or live/work conversion--with no sprinkler system required for up to 3 residential units. Already equipped with 1 full bath and 4 powder rooms, and featuring two finished floors, the layout adapts effortlessly to your vision--be it modern apartments, stylish offices, retail space, or a dynamic studio. Spacious and bright with 5,180 sq ft across two levels Excellent bones

Stunning Contemporary Home in Great Barrington - Perfect Blend of Privacy and ConvenienceDiscover this beautifully designed 2,500 sq. ft. contemporary residence nestled in the desirable Great Barrington area. Offering 3 spacious bedroom suites , this home combines elegant style with everyday functionality.Step outside to your private fantasy backyard -- an entertainer's dream featuring a charming gazebo and a generous deck, perfect for hosting gatherings or relaxing in your own outdoor oasis.The oversized garage provides ample storage and includes a versatile space above, ready for your expansion ideas. With rough plumbing and electrical already in place, customizing this area is effortless. Located 2 min from Monument Mountain Reservation and 6 min to Main Street.

A Nature-Lover's Haven Awaits Set on an expansive 94-acre stretch bordering the tranquil Tolland State Forest, this distinctive property combines unmatched privacy with exceptional natural charm. Envision life along the serene Farmington River, with hundreds of feet of stunning river frontage and your very own storybook-style covered bridge--an extraordinary hallmark of this countryside escape.Highlights Include:Vast Acreage: 94 acres of secluded, wooded beautyRiverfront Magic: Extensive frontage on the Farmington RiverSignature Feature: Historic-style covered bridge adds character and charm

Located on one of Egremont's most picturesque roads, this beautifully designed contemporary home offers panoramic views from nearly every room. Set in a low-tax town just minutes from Great Barrington, this home is private, comfortable and versatile. The main house has perfect flow, great scale rooms, tons of light, a beautiful stone fireplace, custom Kitchen, and the prettiest of outdoor spaces. The connected ADU/Guest suite has a private entry, ideal for guests, caretaker, or rental income. Perfect for primary residence, vacation retreat, or income producing property. A tranquil setting with easy access to area amenities. Come enjoy the view!

Updated and spacious condo just a short distance from Main Street Stockbridge, downtown Lenox, and all the Berkshires has to offer! Premier Unit at Stockbridge Terrace: Enjoy peaceful living on a private cul-de-sac with a limited number of units. The main level living setup is perfect for the primary resident, featuring a large primary bedroom with an en-suite bath and walk-in closet, an open-concept kitchen that has been recently updated complete with top-of-the-line appliances and all new high end cabinetry. The Great Room boasts cathedral ceilings bringing an abundance of natural light and a soaring gas fireplace for added ambiance. Enjoy your private backyard views from the 4-season sun porch equipped with both heat and A/C for year-round comfort.

This fine, four-bedroom, two bath colonial saltbox home just south of the village of Stockbridge is a handmade work of art and an important slice of Stockbridge history. It was constructed on or about 1750. There are patinaed wide board floors throughout as well as five fireplaces (three wood and two gas) and much original hardware. The home is surrounded by perennial gardens and a formal, boxwood garden, all of which have been meticulously maintained. There are two stone patios which look out over four acres of pasture to the west. This home is fueled by gas heat and is serviced by town water and sewer. Perhaps the famous Reverend, Johnathan Edwards and Chief Kondapot of the Stockbridge-Munsee Indians met in the front parlor a time or two.

Easy living Ranch home on beautiful Onota Lake. Fantastic views of the Lake and Distant Berkshire Hills. Enjoy westerly sunset views from your expansive, manicured lawn and almost every room in the house. A quiet setting with comparable homes and easy access to all the Berkshires has to offer. Needs a little TLC, but well worth it for this sought after location and lifestyle. Hardwood floors refinished and interior recently painted.

Designed in 1929 by noted architect Henry Seaver (Berkshire Museum, Lenox Town Hall), this distinguished Georgian Colonial was once the centerpiece of Pittsfield's social scene. The home preserves exquisite 18th-century details - mantels, wainscoting, and finely crafted woodwork salvaged from two of the city's earliest residences, making it a living piece of Berkshire history. Set back on 2.5 private acres along prestigious Crofut Street, the estate offers 5 bedrooms and 5 baths, including twin primary suites ideal for hosting friends and family year-round. Gracious living and dining rooms, a peaceful sunroom, a cozy study, and a large eat-in kitchen with Viking range and butler's pantry combine period elegance with modern comfort. This turn-key estate is offered fully furnished and

Escape the city and embrace the tranquil rhythm of lakeside living in this stunning 3-bedroom, 2.5-bath waterfront home. Located on the desirable northeastern shore of Lake Buel, this property is your turn-key ticket to summer on the water. The open-concept living space is flooded with natural light from a wall of windows offering panoramic views of the serene lake. Enjoy your morning coffee or evening cocktails from the three-season room, feeling the gentle lake breeze. Your private dock awaits, offering effortless access for boating, swimming, and kayaking. Imagine spending your weekends exploring the pristine waters, followed by a quiet evening watching the sunset paint the sky. This isn't just a second home; it's a legacy of memories waiting to be made. Your Berkshire escape is here.

Great Barrington A masterful rebuild with reverence for Great Barrington's past and a bold reimagining for modern living. This 5-bedroom, 4-1/2 bath colonial sits in-town and blends historic charm with contemporary luxury for effortless, years-long comfort.Property Highlights5 Bedrooms | 4 Full Baths + 1 Half Bath**Complex rebuild from the ground up** - preserved nod to the town's heritage with a fresh, modern interiorChef's Kitchen** - high-end appliances, ample prep space, and thoughtful layout for entertainingRadiant Floor Heating** - in entry Dual Fuel Heat throughout High Velocity Central Air Conditioning** - efficient, quiet climate controlSolid Heavy Doors with Emtek Hardware** - substantial, timeless feel with premium finishes4-Season Porch**

This beautiful home was built in 2006, and updated in 2022. The house is situated on just shy of 5 Acres in the town of Egremont. The home is flooded with sun all day, rarely needing a light on in the house. Direct access to the Green River at the edge of property to cool off on those hot summer days. A new central AC system was installed throughout home and apt A New backup generator, rain gutters, new lighting inside and out, full painting inside and out in 2025. First floor primary suite with jet tub and separate shower. The oversized rear screened in porch is divine, you will never want to leave. A Giant lawn for entertaining and a separate in law apartment for your guests. The garage with radiant heat is perfect for your classic cars or boat. Low Taxes and 5 minutes to GB town.

''Best of Berkshire Living: Gardens, Grand Trees & Income-Ready Guest Cottage''Between the Rockwell Museum and Botanical Garden, minutes from Tanglewood, this nearly 4-acre Berkshire property offers two distinct homes surrounded by heirloom trees and landscaped gardens. The 4BR, 2BA main house features a first-floor primary suite with sunroom, spacious living areas, and central A/C. The charming 1BR guest cottage, with large living room and mini-splits, is ideal for rental income or private guests. Garages for 5+ cars, perfect pool site, and privacy ensured by abutting protected land.

An equestrian dream property offering country living among the scenic hills of Western Massachusetts. Set on 15 acres with over 1,300+/- feet of frontage on the North Branch of the Manhan River and 900+/- feet of road frontage, this exceptional estate provides tranquility, function, and world-class facilities. Perfect for the boutique horse enthusiast, boarding operation, or hosting equestrian events.The property features nine paddocks and a hunt field with multi-species hemlock fencing, top-board electric hot wire, Jug waterers, and ample space for vehicle and trailer parking. The showcase three-stall barn with attached 80' x 180' indoor arena was built in 2019 using SIPS construction for superior energy efficiency.

Nestled in the heart of the Berkshires, this historic Richmond compound presents a rare colonial charm. Spanning 11 bucolic acres with sweeping pastoral views, the legendary c1776 estate boasts a meticulously maintained main residence, three enchanting cottages and a great barn for entertaining. The main residence, a testament to time-honored craftsmanship, features 7 bedrooms and 7.5 baths, each room telling a story of centuries past. The inn's dignified presence is complemented by a dining room, entrance parlor, library, den, period greenhouse, and a well-appointed kitchen that cater to both intimate family gatherings and grand celebrations.

The Ephraim Chapin House, a.k.a the ''Landlord Abel House'' was built in Chicopee c. 1725. In 1979 this handsome home & tavern was dismantled and relocated to Southfield. There it was re-erected upon a new foundation atop a hill, where it now resides on a 51-acre estate straddling the banks of Konkapot River. Once the beloved retreat of an artist and a serious collector of early American art and antiques this 3-story 4-bedroom home has been painstakingly rebuilt and restored.Original wainscoting in the ''keeping room'' is a rare example of interior decorative painting by the Scroll Painter, a documented but unnamed American decorative artist active the 1790's. Other details include original floorboards & exposed chestnut beams, center chimney with 6 brick fireplaces... (See ''More''.)

A luxurious home on one of the most scenic roads in The Berkshires, surrounded by 15 pastoral acres, with picturesque mountain views. Enter a sun-drenched living room with a soaring cathedral ceiling and an elegant fireplace centerpiece. Enjoy an expansive 3-season porch, with panoramic windows and classic mahogany floors. A recently updated eat-in kitchen features Sub Zero appliances and a beautiful butler's pantry. Relax in the newly renovated family room with wall-to-wall casement windows. This 5 bedroom home offers a bonus game room and home office equipped with fiber internet and a spacious private master bedroom with ensuite bath. An additional wing features a separate guest suite with living room, kitchen, dining area, full bathroom and 2 bedrooms. In Alford, renowned for low taxes

HISTORIC BERKSHIRE FARM Best bargain in the Berkshires! Gather year-round with family and friends on this one-of-a kind estate, including 2 houses, 4 historic barns and maintenance building. 161 acres with stunning views, mountain paths, and Jim Kelly's stunning giant stonewalls throughout. Gorgeous New England marble stone farmhouse built in 1780, with modern addition featuring vaulted ceiling and massive windows which flood the dining and kitchen area with light. Enormous custom built hearth and fireplace, mahogany full bar, artisan-made bookcases, wrap-around deck. Close to Williams College and Jiminy Peak. The property offers swimming in two private ponds, 6 bay carriage barn with second floor for offices, studios., or storage.

Spectacular 1896 Victorian on The Hill, completely and stylishly renovated in 2025! This six-bedroom beauty seamlessly blends original floors and grand woodwork with all-new, high-efficiency systems. Key 2025 updates include full insulation, exterior paint and two new upstairs luxury baths. 2024 brought fully ducted Air Source Heat Pumps (central AC/heating) and new windows. A 2023 heat pump water heater, powder bath, and fence complete the efficiency package. Features include an updated kitchen, oversized fireplace foyer, office with separate entrance and a private garden oasis. Located moments from downtown Great Barrington's dining/theatre and Lake Mansfield. A perfect, in-town gem--must see, it won't last long.

Nestled in a secluded, serene setting and surrounded by lush gardens, fruit trees, wildlife and Nature Conservancy on 3 sides, custom-built home offers extraordinary privacy and tranquility. Crafted using wood milled directly from the property, this rustic yet contemporary home boasts a wealth of unique details that highlight exceptional craftsmanship. Moose, deer, bear, turtles, fox and more visit mature grounds tended by master gardener. Incorporates a native stone fireplace, ash sapling banister, antique leaded glass accents, & reclaimed 18th-century tavern doors from historic Egremont Tavern. These elements blend seamlessly with the open-concept floor plan, highlighted by soaring vaulted ceilings and oversized windows. 5 Brs, 5BA w/ attached separate apartment w/ balcony.