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.

Welcome to an Exquisite Country Retreat where thoughtful perfection, exceptional elegance, and stunning natural beauty converge in a rare offering situated on a private 19.7-acre refuge in magical Hillsdale on a most coveted country road. This property invites you to connect with nature while indulging in luxurious comfort. Arrive to simplistic elegance, where timeless materials blend seamlessly with a brilliant layout and thoughtful design. Every detail reflects a commitment to quality and environmental stewardship while immersing yourself in Mountain Views through walls of windows and doors, seamlessly blending indoor comfort with outdoor splendor. A gracious entry welcomes you to the sanctuary where luxury meets sustainability. Open living spaces with high ceilings create stunning focal points, featuring dramatic finishes such as the iconic Noguchi dining fixture and magnificent Calacatta Viola marble adorning the stove hood, fireplace hearth, mantles, and Porcelanosa vanities throughout. Marvel at the spectacular kitchen with custom designed white oak cabinets by a Brooklyn-based bespoke cabinet maker, complimented by a Forte Italian range Experience the warmth of a wood-burning fireplace in the living room or the cozy ambience of a gas fireplace in the sumptuous primary en-suite featuring its dreamy bathroom. Your office (or additional bedroom) is also in this wing of the home. Three additional bedrooms, including one en-suite, another full bath occupy its own private segment. Escape to a world of comfort and conservation at this exquisite country retreat where every moment is infused with the magic of nature's embrace. Discover the unparalleled beauty of this remarkable property, while enjoying all the Hudson Valley and Berkshire bounty and wonders

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!

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!

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.

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.

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!

An early Hudson Valley farmhouse, this c1840 eyebrow colonial sits on two and a half acres with a guest house. There are plenty of period details to fall in love with like wide, old growth pine floorboards and classic farmhouse two-over-two windows. Comfortable, approachable, and built with function in mind like all great northeastern cottages, the rooms are nicely sized and flow easily into one another. The country kitchen is simple, sweet and sunny with classic bead board cupboards and a farmhouse sink, and there's a mudroom leading outside into the lawn. There is a first floor bedroom & full bath, and on the second level, along with two additional bedrooms you'll find a large, central seating area & another full bath. Across the lawn and past the firepit, French doors lead you into a streamlined, new build guesthouse. There is a spacious living room with a vaulted ceiling & Noguchi pendant. The large bedroom has a new ensuite bath with a beautiful marble shower. There is a 1 car garage attached. Updated, high end mechanicals in both homes. 720 Center Hill Road is very much the quintessential Hudson Valley farmhouse, charming and sweet. 2h to NYC and 20m to Amtrak.

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

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

Towards the end of Sky Top Road and tucked away at the end of a long driveway sits The Nine-Square House. A modernist masterpiece, the home is perched amidst dramatic natural topography with magnificent views of the Taconic Hills. The Nine-Square House was born of a several-year-long collaboration between a multi-disciplinary artist/designer and an esteemed architect. The result is an immensely livable and sustainable 3,900 sq-ft home that carefully balances the relationship between its well thought out interiors and the surrounding wooded landscapes and impressive open views of multiple mountain ranges. All features of the home were created to be both functional and pleasing to the eye, addressing every conceivable ergonomic and environmental question. The nine-square philosophy of living is very much felt in the distribution of spaces - on the main floor, the double living room, dining area, and kitchen all flow into each other and are anchored by a marble fireplace and three large glass doors opening to the exterior terrace with a breathtaking view. The kitchen features Danish-designed Reform cabinetry, Bardiglio marble, and Fisher Paykel appliances. An office, a washroom, a dry bar, and a generously proportioned laundry room complete the main level.The central architectural piece of the home is the solid white oak staircase leading up to the second floor. The 4 bedrooms upstairs, though spacious, are much more private and intimate, each with large windows on 2 sides, communing with the serene and quiet landscape outside. The 2 sizable bathrooms have dedicated shower rooms and freestanding soaking tubs with panoramic views. The expansive landing of this level has a reading room at one end and a sitting area at the other.Distinguishing features of the Nine-Square House include high energy efficiency due to insulation exceeding all current standards, multi-zone central AC, radiant heated floors, solid 200 lb interior doors, satin nickel Kohler fixtures, cast iron sinks, and solid forged and machined brass and satin nickel door hardware. An expansive floor plan and extensive technical solutions are met with human-scale rooms, creating an abundantly peaceful and welcoming environment. The land around the house is perfect as it is. There are wooded and open areas, with meandering walking paths trailing through the property, planted with native plants. The home comes turnkey with all the curated furniture included.,AboveGrade:3886,APPLIANCES:Water Softener,EQUIPMENT:Smoke Detectors,Water Filter,ExteriorFeatures:Outside Lighting,FLOORING:Concrete,Wood,FOUNDATION:Concrete,ROOF:Rubber

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.

Sunrise Sunset is a stunning 17-acre property in Columbia County with unparalleled mountain views. The home is an architect designed and built B & B with a private living space. It still has all the necessary licensure and zoning to operate as a B & B, though the buyer can simply use it as a spacious home just hours from New York City and minutes from all the glories of the Hudson Valley. The three guest rooms, which could be used as family bedrooms, offices, or studios, occupy the second floor of a three-bay garage. Each is private, en suite, with a balcony. The architect ensured utmost privacy between guest balconies by angling the dividers between them. They all command sunset views of the Catskills, and sunrise views of the Taconic Mountains which are a part of the historic Berkshire region. Hikers in the Taconics can access CT and MA by walking across state lines from New York. Accessible from the guest rooms or the driveway, a spacious light-infused gallery occupies the center part of the home. It is perfect as a gathering place or for receiving guests to a B & B or a holiday party an elegant showpiece. To the right of the gallery is the residence. Some of the most significant features of the home are the soaring windows with breathtaking views, skylights opening rooms to the heavens, antique doors as well as hand-crafted wooden doors, leaded windows, an indoor 30-foot regulation-size lap pool, and flowing interior spaces that are as inviting as they are stylish. Probably the most dazzling touches are the stonework throughout, made entirely of stone found or quarried on the property. Much of it is limestone from the property's own limestone quarry. The only parts of these stone highlights that are not from the property are the numerous accent pieces of vivid blue iron ore. The stone masterpieces, some small and some very large, are featured surrounding the fireplaces, in bathrooms, and in other areas, bringing local history and natural resources together.The fully equipped kitchen, great room, and dining room flow graciously to create a friendly and comfortable family space. The primary suite is upstairs, and both bedroom and bath open through glass doors to a balcony with full views. The beautifully crafted sinks are custom-made from cherry wood from the property. The new owners will want to add finishing touches to certain areas. Easy access to private walking trails, Hudson, Great Barrington, and Catamount Ski Mt.,AboveGrade:3200,Basement:Garage Access,Interior Access,Below Grnd Sq Feet:1000,FLOORING:Wood,FOUNDATION:Concrete,InteriorFeatures:French Doors,Gas Stove Connection,Sliding Glass Doors,Walk-In Closets,Level 1 Desc:GALLERY GREAT RM DINING KIT DINE-IN OFFICE .5 BTH,Level 2 Desc:CONT..3 BEDROOMS 3 BATH,Level 3 Desc:PRIMARY SUITE,OTHERROOMS:Breakfast Nook,Formal Dining Room,Great Room,In-Law,Laundry/Util. Room,Office/Computer Room,Sun Room,ROOF:Asphalt Shingles,Unfinished Square Feet:1000

Experience the quintessential village charm in this delightful Cape Cod-style cottage nestled in the heart of Copake, NY and picturesque Hudson Valley. Enjoy gatherings in the spacious great room featuring a welcoming gas fireplace, creating a perfect setting for relaxation and entertainment. Step out onto the charming screened porch, where you can savor the fresh air and tranquil surroundings, ideal for morning coffee or evening unwinding. Just a leisurely 2-hour drive from NYC.

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.

Lakeside living at its finest. Here at Copake Lake every day feels like a vacation day. This is your chance to own a bright, cheery, energy efficient lakeside home. Copake Lake is a pristine glacial lake where boating, fishing, swimming and kayaking are frequent pastimes. Relax on the front deck overlooking the lake or hang out on your own private boat dock. The house was built new in 2020 on the foundation of an old lake cottage and features an open floor plan with lots of natural light and a spacious loft bedroom. Make your move to the lake today!

You Do NOT Want To Overlook This Beautifully Updated Home In The Highly Desirable Columbia County Town - HILLSDALE. Welcome To A Spacious 3- Bedroom RESORT-LIKE Residence That Offers Plenty Of Comfortable Living Space Through Out The Main Level & Fully Finished Basement. It Is Nestled In A Picturesque Tree Laden Area And It Features Relaxing Covered Patio And An Extra Large Back Porch. But There Is More.. This Home Has A LAKE ACCESS ! Town of Hillsdale Is A Hiker Paradise & It Is Known For Its Fantastic Landscapes & Gorgeous Views. In Addition The Hillsdale's Town Center That Features Dozens Of Historic Structures Was Added To The National Register of Historic Places. This High Demand Area Is Close To EVERYTHING (Bash Bish Falls, Taconic State Park, and the Catamount Ski Area..) And is ready for YOU!!! Strateggically Situated Near Hudson, New York and Great Barrington, Massachusetts.

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 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.

Unparalleled 134 acre estate fronted on Copake Lake and adjacent to the Copake Country Club. Spacious, 7 Br 6 Ba stone & wood home surrounded by artfully designed stonework and lush landscaping. Great room with fireplace, chef's kitchen and 4 season sun-room. Grotto-like Swimming pool with multi-level terraces and outdoor kitchen. The tennis court is hidden out of site beyond a wooden foot bridge. Past the stocked pond are the horse stables with a fenced-in pasture, and a 3,600 square foot heated Hangar, perfectly suited for an artist's work space, a recording studio or a classic car collection. Several dramatic building sites have been thoughtfully cleared revealing jaw-dropping panoramic views of the Hudson Valley and the Catskills & some w views of lake. 2,200 ft of lake frontage, trails throughout the wooded hillside & a private island.Ideally located between Hudson, NY and the Berkshires. Close to multiple ski resorts, Taconic Parkway and 2 hrs. to NYC & 2.5 hrs. to Boston.

Don't miss out on this exceptional opportunity in this serene Taghkanic neighborhood! This charming bungalow home boasts nearly 1,000 square feet of interior living space, 2 bedrooms, and 1 full bathroom. Enjoy ample parking, including a spacious garage/shed, providing convenience for homeowners. Situated on a 3-acre lot, the possibilities here are endless. Large wrap around porch to enjoy the upcoming summer days/evenings. Conveniently located near Taghkanic High School and Route 23, with plenty of dining options nearby to select from. Schedule your showing today!

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!

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.

Look no further for your country dream home! Surrounded by farmland, and breathtaking mountain views, this beautifully designed split level home, is adorned with an eye catching, herringbone pine, front foyer.As you ascend, you are greeted with an open floor plan, gleaming with natural light. Gorgeous kitchen with granite counters, and tiled backsplash; All Stainless steel appliances. The living room has a pellet stove for auxiliary heat, leased solar panels on roof allow for minimal electric charges. The primary bedroom has a en suite bathroom, flocked by two more bedrooms and a large, hallway full bath. Partially finished basement makes for an awesome playroom/den. Newer updates include the kitchen, all appliances, AZEK brand decking with vinyl rail system on expansive back deck, which overlooks a lush, private backyard, with panoramic views of the Taconic range. Generator transfer switch for ease of mind. Great location on a quiet, country road, without seclusion.