West Stockbridge MA Real Estate & Homes for Sale

Welcome to Wildflower Cottage, a charming hideaway nestled in the woods of upstate New York. This modernized interpretation of a traditional New England bungalow has undergone a complete remodel, optimizing every inch of its footprint. The recent additions of decks, porches, stairs, and planter walls seamlessly blend the cottage with its natural surroundings. Reimagined and designed by Rebecca O'Donnell, founder of The Quiet Botanist, this partially wooded and cleared land features wildflower gardens, diverse birdlife, and a stream. Situated adjacent to the expansive Bebee National Conservation Area, this property offers a secluded haven for nature enthusiasts, while still being conveniently located in charming Columbia County and a short drive to the picturesque Berkshires.

On over eight acres of woodlands in the hills of Austerlitz sits this picturesque cabin. Connected to hundreds of acres of state land, you can hike Harvey Mountain right out your front door. The recent renovations make this light & bright home a completely move-in-ready proposition. The original beams have been left untouched throughout and create warmth in tone, while the rest of the home has been finished with a clean, neutral palette. The kitchen has an English style range, marble countertops and lovely deep red cabinetry, and a farmhouse sink looks out over the property. The adjacent living area is anchored by a wood stove. There are two bedrooms and two baths on the main floor, one is ensuite and the other, with an antique clawfoot tub, is shared. Both are finished with beautiful Moroccan zellige tile. Upstairs, there is a cozy, private living space and a large light filled third bedroom. You'll find a large two car garage outside for parking & hobbies. The home borders the Hudson Valley/Berkshire border and is equidistant to both Chatham and West Stockbridge and just over 2h to NYC.

Fantastic Barn with Attached Cottage - Ready to Renovate Immaculate 2 bedroom cottage with views of the Spencertown Hills. Wood floors, lovely southern exposure. New deck overlooking your rolling field below. Bounded by stone walls behind. Quiet dirt road for long walks. Attached 4,000 square foot BARN with great potential.10 mins to Chatham or 10 mins to the Berkshires. Ideal!

Contemporary 2BR Chalet originally guest house on 22 acre Estate Property. The main house burned down, but the foundation, well and septic are ready for the next owner. Property has expansive views to the South and West. Possibility of subdivision separating property into two separate parcels for family compound or individual development. Property is minutes from the business district of New Lebanon with restaurants and other stores. 15 minutes to skiing at Jiminy Peak and access to the Berkshires, Tanglewood, Pittsfield and Great Barrington.

Welcome to Meadow Wood. This elegant property on a secluded reach of the Green River epitomizes the concept of indoor/outdoor living. The graceful and meticulously maintained 30 acre estate features specimen trees, established gardens, a lilypond, terraces, pastoral views, and wonderful privacy. The custom home, built by one of the region's premiere builders, has been featured in design magazines, garden tours & has received a Garden Club of America award for its ethos & thoughtful use of building materials. The house was constructed using sustainable & recycled low maintenance building materials designed to last a lifetime. In addition to the light-filled main house, the property includes the gardens, fenced fields, a 2 car garage w/ potting room and a studio space. The Gunite pool is surrounded by an espaliered apple tree fence & generous stone terrace. The large screened pool house includes 1/2 bath, outdoor shower, kitchenette & massive fireplace. Further from the house is the barn complex consisting of a 2 bedroom apartment with yard & patio, separate studio apartment and 4 garage bays. A barn, cutting gardens, and a separate private drive complete this part of the estate. Hidden from the road, the main house is approached by a long drive lined with mature Scarlet Oaks & daffodils. A courtyard filled with specimen crabapple trees, stone walls & walkways creates the welcome entry to this one level home.The exterior walls are planted w/ climbing hydrangea that blur the

The Every House has the soul of an artist and offers a little something for everyone. A pond for reflecting a pool for a cool dip. A quiet road to walk on. Proximity to Chatham for life's essentials. The mudroom is where you start, shedding boots and coats. Upstairs a country kitchen looks out over the grounds keeping things in perspective. The living room is large enough for formal and informal coexist, anchored by the fireplace. The sunroom serves as a dining room for light filled soirees. First floor bedroom with full bath and steam shower. Upstairs 3 large bedrooms. Third floor office. Amazing carriage house with 2 bedroom apartment. Fruit trees and gardens!

There are few homes as fine a seed as this one. Set on a quiet 6.9 acre parcel in the rolling hills of Chatham, The Seedling is a beautiful custom designed home with room to grow. The home lives large, with the centerpiece being a lofted great room, featuring a double helix staircase to an oversized loft, and a granite hearth. The soaring windows and sliding doors bring light streaming into the open plan living and dining rooms, and there is ample room to entertain. A fully equipped kitchen and powder room round out the living space. The primary suite features two sets of sliding doors for privacy, and a large and light-filled bedroom with sliding glass doors to the yard. Downstairs, you'll find a huge finished basement, ripe to be set as a guest suite, entertainment room, or a combination of uses. The basement is 502 square feet with dedicated laundry and storage rooms.

Indulge in opulent living in Columbia County, NY! This modern home offers panoramic views of the Berkshire Hills & Catamount Mountains. Enter a grand hallway leading to a dining room with floor-to-ceiling windows showcasing the pool area. The chef's kitchen opens to a spacious Great Room with a fireplace and breathtaking vistas. A loft library offers tranquility. A home office can double as a guest bedroom. The first floor features three guest bedrooms, a gym with sauna, and pool access. The upper level boasts a master suite with a fireplace and private terrace. A grand roof deck overlooks the pool, hot tub, and outdoor kitchen. The lower level features a movie room, laundry, and half-bath. Situated on 10+ acres of landscaped property with lawns and country fields, this is the ultimate country escape. Experience luxury living at its best in Columbia County!

Private country setting, contemporary design, and energy efficiency all come together in a serene landscape setting with beautiful views of Catamount Mountain. 3500 SF, stained cedar sided home, 4-bedroom, 3.5-bathroom. Home is sited to maximize long distant views. This certified passive home is industry leading, with its triple insulated floor to ceiling windows and doors, high R-value walls and ceiling and an energy recovery/ventilation system. Finished three-car garage can easily accommodate EV charging stations and an abundance of additional storage needs. The centerpiece of the home is a large open floor-plan kitchen/dining/living space with 13' + high ceilings. Oversized sliding doors from this space make the connection to the concrete paver patio, meadows and woodlands, second nature. Close to the Berkshires, Great Barrington and Stockbridge, 30 minutes to Hudson and minutes to the hamlet of Hillsdale, and Catamount. Experience true green living.

Tullar Farm represents a rare opportunity to own a piece of history where timeless elegance meets modern comfort amidst the serenity of South Egremont's charming landscape. With its rich architectural heritage, generations of proud stewardship, and unrivaled natural beauty, this distinguished estate stands as a testament to the enduring legacy of its past and the promise of the future for generations to come. Set on 67 +/- park-like acres this property offers 3 unique residences, a mature specimen tree farm, a spring-fed pond, wooded walking trails, and captivating views of the distant mountains all just a stone's throw away to restaurants and shops. At the heart of the estate stands The Tullar House; a well-preserved and substantial 6-bedroom 5,000+ sq ft antique Dutch Gambrel dating back to 1761, reported to be the 2nd oldest house in Egremont. Retaining much of its original charm and detail, this historic jewel boasts ample-sized rooms for gatherings and entertaining, a renovated chef's kitchen, a formal dining room, 3 grand fireplaces, 2 primary suites, and plenty of room for guests. Enjoy sweeping views of the grounds from the porch laid with locally sourced marble or relish in the shade of 'The Champion', a 250+-year-old Black Walnut Tree standing as the oldest in the state and serving as a living testament to Tullar Farms' rich past. The exterior is a sight to behold with ornate and symbolic details that capture the attention of all who pass by.

One of the few brick Georgians in Columbia County, the Samuel Wilbur House is a stately reminder of the past. Wilbur, a NYS Senator during the Colonial era, created a home of outstanding beauty and balance. Huge original barns, renovated Carriage House, 20 x 40 heated, saltwater pool, bluestone patios and stream give the outdoor space an instant country feel. The home consists of five separate but connected living spaces, each with their own kitchen, baths and bedrooms. A family compound in a single building, a small inn or bed and breakfast. All of the finishes are of the highest quality, with many of the original details intact. The floors have over a century of patina, the moldings are hand crafted, the fireplace mantels works of art, exposed beams and bricks lend interest to the ceilings and walls. Updated where it's needed, particularly in the main kitchen where modern aesthetics give clean thought to this antique beauty. Wonderful new windows bring in the light and amazing original windows, including the original Palladian window in the upper hall,FOUNDATION:Brick,Masonry,Block,Concrete,OTHERROOMS:Library/Study,Sun Room,In-Law,Workshop,Formal Dining Room,Great Room,Office/Computer Room,AboveGrade:5195,AMENITIES:Pool,ROOF:Asphalt Shingles,FLOORING:Tile,Ceramic Tile,Wood

Introducing The Renard Estate: A Picturesque Country Retreat in Old Chatham. Prepare to be enchanted by Renard Estate, a sprawling 101-acre Country Home and Gentleman's Horse Farm nestled in the heart of Old Chatham. This unique property perfectly embodies the essence of Hudson Valley living and serves as the ultimate family compound. As you arrive, you'll be greeted by the charming sight of rolling bucolic hills and serene vistas, setting the stage for complete privacy. The property's crown jewel is a serene 2.5-acre private pond, adding a touch of elegance to the landscape. Accessible via a long circular driveway, it guides you into this idyllic hillside setting. This property fulfills the dreams of equestrians and nature lovers, offering full horse facilities and meandering riding trails. It also boasts a quarter-mile of Kinderhook Creek frontage, a paradise for fishing enthusiasts. The turnkey home boasts seven bedrooms, four baths, and inviting living spaces. The living room exudes coziness, while the spacious dining area features a captivating stone fireplace. The kitchen, with its welcoming center island, forms the heart of the home, designed for hosting and entertaining family and friends. The outdoor spaces are equally captivating, featuring a Bluestone Patio, a heated in-ground pool, a rustic stone barbecue, a basketball court for lively games, and a kids' playground. The land is adorned with mature plantings and old trees, as well as a flourishing vegetable and flower garden. For those who share a passion for horses, a remarkable 13-stall horse barn awaits, complete with a heated tack room for added convenience. Outdoor riding facilities, paddocks, and run-in sheds provide comfort and shelter for your four-legged companions. Exploring beyond the horse barn, you'll discover a versatile Pole Barn and a recreation shed. Follow the siren call of Kinderhook Creek, a classified Trout Stream, and let your fishing rod, kayak, and water adventures come to life. Renard Estate offers a unique opportunity to own a piece of paradise where nature and luxury seamlessly harmonize.

A long winding country road, a dirt driveway, a fifty acre sanctuary. This stunning post & beam barn house sits on a one acre pond amid fields & fields of wildflowers and deep pine forest. Built by a premier builder in the area, the contemporary home has 20ft ceilings, a giant expanse that feels warm and inviting. The home is longer than it is wide with a substantial kitchen at the center. A large island and dining table run side by side, and you'll find high end appliances in a sharp, polished black finish. A wood burning stove sits between the kitchen and living room, and a den sits in the northwest corner. This entire first floor looks out over the pond to the fields in the distance. Upstairs, you have a giant open loft overlooking the main living space, a bedroom with gorgeous views of the property and a full bath. Antique fixtures such as faucets, sinks and hardware are interspersed throughout the home, and the post and beam construction incorporates reclaimed hand hewn beams, making this new build feel authentic and well beyond its years (in a good way). Radiant heated concrete floors span the lower level of the home where you'll find three bedrooms. Two share a full bath, and one is ensuite with a large, walk-in closet and glass doors leading outside to a pebble patio overlooking the water. There is also a sitting room on the lower level, light and bright, with sliding glass doors that lead outside. The entire house is west facing and enjoys fabulous sunsets. A cottage is tucked back against the tree line, as charming as could possibly be with a full kitchen, a large bedroom and a full bath. 2.5h to NYC, 2.5h to Boston, 30m to Hudson and Amtrak. Dorland Farm is a little slice of Hudson Valley heaven.

Welcome to the Elijah Hudson homestead and farm, nestled in the hamlet of Malden Bridge, NY. Steeped in rich history dating back to the mid1700s, this property boasts a captivating past as a colonial-era inn, meeting place for traveling preachers, and farm of a co-founder of the Federal Stores mercantile (Old Chatham). The homestead, lovingly restored over decades, offers a glimpse into the region's storied past, with original features meticulously preserved alongside modern updates for comfortable living. The property encompasses 43 acres of picturesque land, including sprawling fields, pristine gardens, and tranquil woods teeming with wildlife. Two meticulously restored barns, including a stunning German horse barn and a Dutch dairy barn, stand as testaments to the property's enduring legacy. The Dutch barn, fully rebuilt in recent years, presents a blank canvas for the next owner's vision, while the German barn offers versatile finished spaces for entertainment, hobbies, and more. Experience the best of country living in this idyllic retreat, where generations have gathered to celebrate life's milestones and forge lasting memories. With its proximity to local amenities, recreational opportunities, and vibrant community life, the Elijah Hudson homestead offers an opportunity to own a piece of living history in the heart of upstate New York. Don't miss your chance to write the next chapter in this timeless legacy. Property Improvement Highlights This meticulously maintained property has seen numerous upgrades and renovations over the years, ensuring modern comfort without compromising its historic charm. Recent improvements include an upgraded bath and laundry rooms, a complete restoration of the Dutch barn, and exterior painting of both barns, among others. With a commitment to preserving its heritage while embracing modern living, the Elijah Hudson homestead is ready to welcome its next steward into a future filled with possibility.

This extraordinary, newly updated 16 acre oasis offers a tranquil retreat for the weekender or if you are lucky to live here full time. Meander down the paved 1/4 mile driveway and your private world of serenity awaits. Included is a stunning kitchen with new granite counter tops, built-in appliances, custom inlaid hardwood floors, newly updated baths and trim. The open floor plan allows you to entertain guests while you're in the kitchen. After dinner you can retreat to the family area with propane fireplace or for those warm nights exit to the oversized decking. Just some of the amenities this home boasts are a lighted tennis court, in-ground pool and spa, knotty pine paneled billiard room and sauna. Updated HVAC system, well pump and roof. The oversized 3 car garage features a 50 amp RV/EV hookup. Just 30 min to Hudson.

Former Schoolhouse Completely Redone 1840s One room schoolhouse with the most amazing floors and exposed beams. Come in through the original entrance! The classroom is now a living room with a fireplace and full bath. The expansive and well appointed kitchen has all locally crafted handmade cherry cabinets. A den just off the kitchen is perfect for a post dinner chat. The french doors lead out to a stone patio, a small barn and the old outhouse! Upstairs there are two huge bedrooms with large closets. Set on over 5 acres on a gorgeous country road.

Welcome to your private oasis nestled between Hudson and Chatham, offering the perfect home or family compound on expansive, picturesque land featuring rolling hills and serene large ponds teeming with wildlife, including heron, duck, and kingfishers. The long private driveway leads up to the spacious house, surrounded by nature's beauty. Hosting gatherings is effortless in this large home, ample space for parties of all sizes: cozy gatherings or lively large events! The well-appointed kitchen and island are perfect for culinary delights, while the log cabin invites cozy evenings by roaring fires and games of pool or poker. Enjoy breathtaking views of mountains from the kitchen and dining room, where the ever-changing scenery captivates with each passing weather pattern. Relax with your morning coffee on one of the porches, deck, or by the tranquil free-form inground salt-water pool surrounded by lush greenery. Or unwind with an evening drink as the sun sets over the tranquil landscape. Indoors, the home theater provides endless entertainment. Crafted in unique connective architectural style, this lovely home boasts high-end Pella windows and doors, custom wide board flooring, and white marble and black granite floors, exuding sophistication and charm. The primary suite offers stunning views, double shower with rain shower and stone floor, and two walk-in closets. Additional features including Adirondack-style log billiard room with stone fireplace and wrap-around deck, a breezeway, piano room, dog room, laundry, sun room, and spacious walk-in pantry. Finished lower level boasts impressive home theater, expansive wine cellar, recreation room, and office/den. Ample storage and Generac home generator ensure convenience/peace of mind. Easy access to NYC via nearby Amtrak, just a short drive to Berkshires for exceptional dining experiences. Explore nearby attractions: Lake Taghkanic State Park outdoor adventures, or indulge in local farmer's markets and antiquing in Hudson. Thrill-seekers: Catamount Mountain Resort offers skiing/summer activities, including the longest dual zip line in the US, Aerial Adventure Park. Discover the wonders of Howe Caverns. Enjoy easy access to grocery stores and other amenities. Taconic Parkway, Interstate 90 offer easy travel to NYC, Boston and Albany International Airport. The perfect getaway! Listed separately, two contiguous homes also available to complete your family or home business or farm compound.

Welcome to Mill Daughter's Manor, an exquisite example of Victorian architecture at its finest. Built in the 1870s, this historic home has been thoughtfully maintained and renovated, blending classical elegance with refined upgrades. With its commanding presence, the 3-story home is situated on a quiet street within walking distance of town amenities and nature trails. The 2.7-acre property features partially wooded areas, a fenced-in backyard, a carriage house, and inviting porches, creating a tranquil setting ideal for both leisure and entertaining. Centrally located with easy access to Hudson and the Berkshires, Mill Daughter's Manor is a true gem at the heart of Columbia County.

GREAT POTENTIAL TO HAVE YOUR OWN CABIN IN THE WOODS! This property is located in Sherwood Forest Lake District and features 3 BR, 1 bath, and one car garage. Being sold "as is" including debris in and around the house. House needs work to bring it back to its glory. Buyer to perform due diligence, including well testing, smoke certificate and utilities. Property failed Title V. There is a wood stove for heating and electric hot water heater. Would be perfect for future Airbnb or hunting lodge. Close to ski areas. Will not qualify for financing. Must be cash or rehab loan. Subject to probate approval. There is one additional lot being sold with this house and all for the same low price. The parcel is an additional .527 acres.

Come and see this 9-family home plus 1 retail store almost 5,000 sq ft 2-2-bedroom Apartments,2-1bedroom apartment and 5 studio apartments. Also 1 retail store on ground floor. All apartments under market rents. Close to shops and transportation. Great investment property. Large city free parking lot behind the building. Current rent roll with the 7 rented units is $61,500 not including the 3 vacancies, projected fully rented income will be $87,900

The quintessential country house, built in 1850 and renovated in 2016 offers historic character.. The welcoming Living Room of this post and beam constructed farmhouse features a storybook living room with beamed ceiling, Rumford wood-burning floor-to-ceiling exposed brick fireplace and wide-board floors. The eat-in country kitchen is spacious and light-filled with access to a sun drenched deck. There's also a convenient ground floor full-bath. Upstairs, you'll find a vaulted primary bedroom that affords plenty of light. A deck off the primary is the perfect spot for morning coffee. Three additional bedrooms, two adjoining that is perfect for a home office set up. Second floor bath and laundry. The 2016 renovations includes new windows, plumbing, and baseboard heating. New propane furnace and hot water heater installed this year. Outside are mature trees, stone outcroppings, an original outhouse (now serving as a garden shed) and a choice of three decks to escape the days stress. A whimsical old hand -pump harkens back to the simpler times of country style living. The easy to maintain 1/2 acre parcel is surrounded by 60-acres of woods. Proposed Hudson-Albany rail trail across the road. Convenient to Hudson, Chatham, and 2 hours NYC. Seller says SELL!

Mount Washington serves as the magnificent backdrop to the serene garden paradise that is The Mountain View Farmhouse. Set on a quiet dead end road in the hamlet of Copake Falls this double lot property has been sweetly manicured and set up for your calm enjoyment of the beautiful views. Time stops once you enter the grounds of this precious farmhouse expertly renovated to bring all the modern conveniences to a charming and character filled home.Upon entering the front door you and your guests will be greeted by the warmth only exposed beams and original wide plank wood flooring can evoke. The first floor has an open layout often desired but rarely achieved in homes of this era. The living room effortlessly flows into the dining room and beautiful kitchen that puts the Mt Washington views on display as you prepare your flowers and vegetables from your very own garden. A guest bathroom and side entrance complete the first floor. Upstairs 3 perfectly sized bedrooms (One used as an office currently) and a full bathroom offer comfortable stays for you and your guests.A large portion of the property is fenced in and filled with beautiful plantings, trees and enough tulips to keep every room of your home and your friends home filled all spring. Another area of the yard contains an expert's raised bed garden to grow your own fresh herbs and vegetables all summer long. Set in a peaceful and quaint neighborhood you are just moments away from a hike to Bash Bish Falls, a day on Copake Lake and skiing down the slopes of Catamount in the winters. Hudson, NY and Great Barrington, MA are both a 15-20 minutes drive away where you'll find the best shopping, restaurants & social events the Hudson Valley has to offer.

Nestled on one of the larger lots in this friendly lake community you will find your charming lake home less than two hours from NYC. This unique property includes a 2 car garage with storage as well as plenty of parking for those who gather. Perhaps you see yourself playing golf at the Copake Lake Country Club {1.1 miles}. Or stay in and enjoy the air and scenic views at The Greens Restaurant and Club House where you'll find Mickeys Marina and boat dock {.04 miles}. It is hard not to find peace in such a stunning area, whether you prefer to sit nestled in the trees that embrace your property or decide to venture a bit. This unique and very special home needs a bit of your vision. It has new plumbing, a new water heater, most ducts have been replaced as well as a few new windows. The Kitchen, Bath and Laundry are all plumbed in and are awaiting your personal touch. Your opportunity to make it exactly as your own awaits you. This home/property truly has amazing character and I look forward to sharing it with you. A/O 3/26 continue to show

Nestled in the picturesque town of Craryville, New York, this charming house situated within walking distance to the tranquil Copake Lake, this property embodies the essence of lakeside relaxation while providing convenient access to outdoor recreational activities.It offers versatility and flexibility to live like a two-bedroom home. The well-appointed bedroom provides a peaceful sanctuary, complete with ample closet space and tranquil views of the surrounding landscape. Additionally, a bonus room can easily serve as a second bedroom, home office, or hobby space, adapting to suit your lifestyle needs. The open concept kitchen serves as the heart of the home, boasting ample counter space, modern appliances & granite counters. One of the standout features of this property is its whole house generator.

Welcome to your very own private retreat in the heart of Hudson, New York! Nestled on 8.5 sprawling acres of pristine land, this historic colonial home offers the perfect escape from the hustle and bustle of city life while keeping you just a short 10-minute drive from the vibrant town of Hudson. This home features over 3,000 sqft, 3 bedrooms, and 2.5 baths. Explore your very own wooded wonderland right in your backyard, perfect for nature enthusiasts and outdoor activities. Low taxes! Situated just a short drive from Hudson's historic town center, you'll have access to an array of charming shops, renowned restaurants, and cultural attractions. Hudson is famous for its thriving arts scene, antique shops, and cultural festivals, making it the perfect place to explore and call home. Don't miss your chance to own a piece of Hudson's rich history while enjoying the serenity of your own private oasis!