Great Barrington MA Real Estate & Homes for Sale

Enjoy country living at its best in this 1880 Victorian located down a quiet country lane in the Ancram area which is convenient to all the Berkshire's and surrounding areas have to offer. The home features generous size rooms with high ceilings. Enter through a large foyer that opens into the kitchen with a built-in breakfast nook, Viking stove for the serious chef and an adjacent cozy sitting room with a fireplace which opens to a screened in porch. There is a large living room with a fireplace and a dining area that opens to a porch that overlooks an expansive lawn with room for outside activities. Nearby is a private setting with a heated gunite pool. The primary suite has French doors that open to a porch if quiet time is what you need. Other rooms include five bedrooms, butler's pantry and den. The large barn has a one bedroom apartment/guest house with exposed beams, open kitchen living room and two baths. The other side of the barn is a large open area with exposed beams making for a workshop/studio space or garage. There is also another one story barn for storage and a small orchard all on 21+ acres. Plenty to do or just sit back and enjoy the country air.

This is the home you have been waiting for! Gorgeous views out every window, beautiful sunlit rooms and plenty of space to entertain and live comfortably. Welcome to Millerton, a rural, historic setting within a short distance of a lively main street where you will find a movie theater, stores, art studios, eateries and the Harlem Valley Rail Trail. This home offers a wonderful floorplan including a spacious living room, dining room, family room and a kitchen that opens to an expansive deck. Beautiful hardwood floors flow throughout the main floor. As you make your way upstairs you will find a large primary suite with walk-in closet and en-suite bath. An additional two large bedrooms with a full bathroom as well as an additional room for an office. The home offers a full walk up attic which is perfect for additional storage. The lower level is walk out and perfect for future finished space. This home has it all!

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.

The options are endless for this very special 120-acre property on a spectacular country road in beautiful Ancramdale, NY. The property, which has been a family compound for multiple generations, begins with a very long private driveway that leads to the original 1850's farmhouse and guest cottage overlooking a gorgeous 4+ acre pond. As you continue down the driveway, past lovely rolling hills, an old swimming pool & tennis court, a summer cottage and a couple of other outbuildings, the property goes up a hill to two additional residences built in 1970 and 2000, with stunning views of the mountains and exquisite surrounding farmland. This fabulous property is waiting for new owners to make a new family compound. With the exception of the house built in 2000, the others all need to be torn down or completely re-built (all the infrastructure is in place such as driveway, electric, septics, wells), so it is a question of building, but not putting in infrastructure. Conveniently located to all that the Hudson Valley has to offer, less than 10 minutes to Millerton and Pine Plains, less than 30 minutes to Rhinebeck, Hudson and Millbrook and just 2 hours to Manhattan. Bring your imagination, wonderful properties that offer this level of privacy and views extremely rare.,Other School:DUTCHESS DAY,OTHERROOMS:Office/Computer Room,Library/Study,Great Room,Laundry/Util. Room,Rec/Play Room,Family Room,InteriorFeatures:Electric Dryer Connection,Walk-In Closets,Sliding Glass Doors,Gas Stove Connection,Basement:Interior Access,Garage Access,FLOORING:Wood,Ceramic Tile,AboveGrade:4144,ROOF:Metal,EQUIPMENT:Carbon Monoxide Detector,Smoke Detectors,Cooling:Ceiling Fan,Below Grnd Sq Feet:300,FOUNDATION:Concrete

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!

A Water View Property! About 2 Acre Lot (see the last picture), The main house has 3 bedrooms, and a mobile home addition can provide 2 more bedrooms. 4 bedrooms (and even the Bathroom) with a beautiful water view of Churchtown reservoir, Master Bedroom W/Den, Spacious Living Room, Formal Dinning Room, A Deformed Mobile Home in Backyard, Big Backyard and Side yard, 15 min from Hudson, 2 hours from NYC, Needs Full Renovation, Good for Handyman/Investors/End Users, Price to sell

This property in the village of Millerton presents a unique opportunity for potential homeowners or investors. With one apartment already renovated and ready for occupancy, the first floor offers immediate living space or rental income. The second floor, while requiring further renovations such as the installation of two bathrooms and a kitchen, holds the promise of becoming a cozy 1 or 2 bedroom apartment. The charm of wood floors and the benefit of recent updates like a new septic system and furnace add to the appeal. The inclusion of a garage and dedicated parking for one apartment, along with an additional driveway for the second, provides convenience for residents. Its proximity to the village center means restaurants, shops, and entertainment, such as a movie theater, are just a short walk away. Additionally, the nearby Harlem Valley Rail Trail offers outdoor enthusiasts a scenic route for walking, biking, and exploring the natural beauty of the area.

Millerton Village Investment - This Millerton Investment property is fully occupied and offers four separate rental spaces, with mixed uses for a diversified offering. Two residential units on the upper level, each spanning the length of the building and offering ample space, with covered decks for outdoor enjoyment at the back of the building. The residential units offer a 3BR and 2 BR units. The Main level offers commercial spaces, that also stretch the left and right sides of the building, provide great window exposure along Millerton's bustling sidewalks in the heart of the village.

Village Of Millerton: Business Or Residence - This light-filled building offers unlimited versatility! Two separate rooms plus a full bathroom are currently configured as a small home with a Bedroom and Kitchenette/Dining Area. The space is flooded with sunshine and offers many updates, including windows, bathroom updates, and a heat pump for heat and air conditioning. Embrace the joy of in-town living or begin your next entrepreneurial endeavor right in the heart of Millerton's village.

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.

Meticulously Maintained ELEVATED Log Cabin-Style home and horse barns on 19+ acres with BREATHTAKING Mountain Views. Set off a quiet country road, this stunning setting with impeccably manicured grounds captures one's attention upon arrival. One is immediately drawn to the expansive wood deck complete with built-in grill and impressive screened-in gazebo with fire-pit. This is unquestionably the perfect entertainment perch which captures the expansive long views of the valley and hillsides. Fabulous open floor plan inside, with vaulted ceilings in living room with stone fireplace, large dining area, and light and bright gourmet eat-in kitchen with high-end appliances. Primary bedroom also has vaulted ceilings, stone fireplace, and large walk-in closet leading to primary bath. Den/study off of primary bedroom. Another great entertaining space is found downstairs including a large area perfect for games, exercise or media room with kitchenette. Also downstairs is a large second bedroom and updated bathroom. 3 car heated garage with massive storage space upstairs. 45KW generator. For the horse enthusiast, the property also includes a hay barn, paddock, 4 stall horse barn & tack room, equipment sheds and arena. Great riding trails abound. This exceptional property is move-in ready and utterly magical.

Unveiling, the ultimate retreat for those seeking a legal Airbnb, vacation haven, or year-round sanctuary. Prepare to be captivated by the mesmerizing melody of the Webutuck Creek as it serenades you from your own private back pea gravel patio. Set upon an expansive 4-plus-acre parcel, encompassing two lots, this Millerton gem promises an unparalleled embrace of untouched nature on both sides of the tranquil creek. Welcome to the epitome of rustic charm, (epitomized by) this timeless barn-style abode also boasts(ing) a detached 2-car garage. Step inside and be enchanted by the inviting open floor plan, where a majestic original wood-burning fireplace commands attention, setting the stage for convivial gatherings or intimate fireside retreats. Channel your inner chef in the sumptuous kitchen adorned with marbled quartz countertops, pristine white cabinets, and luxurious brass accents, all complemented by top-of-the-line stainless steel appliances. Gaze out onto the lush surroundings through expansive windows while the warm wood floors beckon you to unwind in style. Upstairs, discover two generously proportioned guest bedrooms bathed in natural light, alongside a bright full guest bathroom. But hold onto your awe because the pi ce de r sistance awaits the master ensuite, a haven boasting unobstructed vistas of the Webutuck Creek and verdant grasslands beyond. Experience year-round comfort with dedicated Mitsubishi heat pumps keeping you cozy in winter and cool in summer, while an installed universal EV charger in the garage ensures modern convenience. Additional delights include the option for an outdoor shower hookup perfect for rinsing off after a refreshing dip in the creek. Convenience meets tranquility with a large utility/laundry room on the first-floor catering to all your country house storage needs. Revel in the abundance of closet space and (revel) in a home where every detail exudes excellence and freshness. Step outside to embark on endless strolls or epic bike rides along the coveted Bronx Rail Trail, conveniently accessible just beyond your doorstep. And when it's time for a leisurely morning coffee or a delightful lunch, Millerton's charming main street beckons with its array of restaurants, shops, and upstate events. "Just a short nature walk away." Why dream of vacations when you can call this idyllic haven home? Don't miss your chance to own a slice of paradise. This is more than a home it's an invitation to live the life you've always imagined.

Introducing Van Rensselaer Lower Manor. Built c1685 onward, this historical home is situated on 62 acres of green lawns, fields and wooded terrain that offer Catskill Mountain views. The main house of the estate recently renovated to preserve past details while introducing modern amenities consists of over 5,000 sq ft of living space with an additional 2,000 sq ft separate studio building and a 2,800 sq ft barn. Approach the home via a circular driveway and enter through a gracious wide hall flanked by the south and north wings of the house. The south wing features a cozy living room with a majestic hearth, leading to a dining room and summer kitchen adorned with French doors opening to a charming gravel patio offering endless nights of entertaining. A convenient powder room and an informal sitting room/office complete this wing. Meanwhile, in the North wing, one is greeted by the original kitchen hearth and bake oven. The wooden mantel has been stripped to lend a more contemporary feel. A second dining room and (winter) kitchen are found off this living space all complimented by a tastefully renovated full bathroom. Three separate stairways provide access to a sprawling second floor with a total of eight rooms, 5 currently set up as bedrooms. Three full baths, all elegantly renovated, complete the second level. Step outside to discover a c1825 post-and-beam barn at the edge of a 60-acre wooded expanse. Significant restoration has been done to maintain its integrity and provide striking views of the Catskill Mountains. Sited closer to the road stands the Flower Shop (zoned for retail), a fully renovated 1950s structure, currently utilized as an art studio. This space boasts 10'8" ceilings, a two-car garage, full bathroom, and large plate glass windows with soundproof inserts. These south facing windows create a soft glow and clean sensibility meant to inspire the pursuit of one's entrepreneurial dreams. Every element of this estate from its 17th century Manor home to the more contemporary Art Studio has been thoughtfully restored to accentuate original details without sacrificing modern comforts. A sophisticated contemporary palette blends seamlessly with the enduring charm of hand-hewn wide board floors, forged hardware, original doors and countless other details to make this property timeless yet current. Located in historic Claverack, the Lower Manor is 10 min to Hudson / Amtrak, 15 min to Hillsdale, 2 hours to NYC

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 approach to this spectacular contemporary barn-style home takes you up a long, winding private driveway past open fields & woods that are part of this special 22+ acre property. At the top of the hill, sits this incredibly private, recently completed, custom, stick built, 3-bedroom, 3.5-bath, contemporary home boasting approximately 4,000 sf of total square footage. This stunning home is designed to take advantage of its exquisite surroundings and to be one with nature with lots of windows, an open floor plan, and soaring high ceilings. Features include a standing seam roof, a lovely in-ground gunite pool, 9' engineered European oak flooring, a fabulous loft office/den, custom cabinetry and vanities, bedrooms with baths en suite, beautiful tiling, a contemporary propane fireplace, high-end appliances and a full basement, the perfect place for a gym/media room/family room/ playroom. Through the trees that surround the home, you can see glimpses of the mountains and pastoral farmland, and with some clearing, the views would be truly unparalleled. Conveniently located in New York's scenic Hudson Valley, just 6 minutes to Millerton & Pine Plains, 20 minutes to Rhinebeck, Red Hook & Millbrook and under 2 hours to NYC. Additional options at additional cost include bluestone patio, decking, garage and much more. Agricultural exemption ensures ongoing tax advantages!! A truly stunning and unique, must-see private property (not in a development).

This historic 1780's Dutch Colonial home sounds like a dream! From the charming details to the lush surroundings, it's truly a unique find. The Koi pond with its waterfall and the stone patio with a gorgeous archway must create a magical atmosphere. And being walking distance to local amenities while still having the tranquility of a rural setting is a rare combination. The interior is just as enchanting, with the family room exuding brightness and warmth, perfect for both indoor and outdoor gatherings. The stone flooring with radiant heat sounds luxurious, and the pellet stove adds a cozy touch. It's wonderful how the space seamlessly flows into the kitchen, making entertaining a breeze. The dining room sounds like the heart of the home, with its beamed ceiling and wide-plank floors creating an authentic antique ambiance. And who wouldn't want to gather by the fireplace for celebrations? Upstairs, the bedrooms maintain the home's charm with wide plank flooring and built-ins for storage. The front hallway's versatility for crafting, office space, or a reading nook adds to the home's appeal. The barn ensemble offering additional space is a fantastic bonus, especially with its pre-existing business potential. Overall, this home seems like a treasure waiting to be discovered by its next owner. It's clear the current owners have cherished it, and it's exciting to think about the memories and adventures awaiting the new inhabitants.

This picturesque property offers a serene escape from the hustle and bustle of city life, surrounded by lush greenery and scenic views. As you approach the home, you'll be greeted by the inviting charm of a classic farmhouse exterior, complete with a welcoming front porch where you can relax and soak in the tranquility of the countryside. But the true highlight of this property awaits outside a stunning inground heated pool, surrounded by a spacious patio area and lush landscaping, creating the perfect setting for outdoor relaxation and entertainment. Whether you're lounging poolside on a sunny day or hosting a barbecue with friends, this backyard oasis is sure to impress. Conveniently located just a short drive from downtown Hudson, you'll enjoy easy access to a variety of shops, restaurants, galleries, and entertainment options. Explore the vibrant arts scene, stroll along the historic streets, or simply take in the breathtaking beauty of the Hudson Valley landscape.

Two bedroom plus bonus room! Beautiful quiet residential street in Sought after Claverack. Just three miles to Warren St! This is a well-loved home! It was built by the owner in 1954 and has never been sold. Tax data says 2 bedrooms but there is an additional room on main level with a closet. This home has beautiful hardwood floors, Spacious Living room with working Bluestone fireplace. Roof is 10 years old; Septic is a 1000 gallon concrete tank, Community water, new high efficiency boiler. Large basement with washer dryer and tons of storage. There is also a 1 car attached garage. Home was lovingly cared for and owner has receipts for Maintenace and upgrades.

This is a Diamond in the Rough. Lake cottage needing some updates, but what a spot to overlook the lake from the front this home. Light and bright dining area and living room are situated in the front with some newer windows. 2/3 bedrooms with main bedroom with views. 1 bath with shower. Lake access with dock and picnic area. Lake is approximately 195 acres with a depth in the deepest area of 14'. Great lake for fishing (and ice fishing), kayaking, canoe, swimming and whatever you love to do by the water. This can only be purchased with cash because it's on leased land. Shared well with two neighbors. Septic no information. Close to Village of Millerton and Sharon, CT. Motivated Seller.....,FOUNDATION:Concrete,Piling,AboveGrade:545,FLOORING:Wood,Laminate,Cooling:Ceiling Fan,Level 1 Desc:2/3 BEDROOMS, LIVING, DINING, KITCHEN,3/4 BATH,ROOF:Asphalt Shingles

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.

LOOKING for a Country home near the Taconic State Parkway in Columbia County? Meticulously maintained Ranch Home is situated on 7 pastoral acres with a COI pond, 2 Sheds. This Spacious 2 bedroom ranch has an open concept kitchen with gas stove and granite counter tops, brick gas fireplace, 2 large bathrooms, large trex back deck for grilling and entertaining. This home has so much to offer: inviting front stone walkway, mature landscaping, circular driveway with plenty of privacy. This is a must see home.

Located at the end of a private road, this four bedroom home is comfortable and sure to please. The first level features a stylish eat-in-kitchen, light-filled dining room, cozy living room, family room, and a powder room. A primary suite with a stunning new bathroom, three additional bedrooms, and another full bathroom off the hallway complete the second floor. Many improvements throughout, including attractive oak flooring on the second floor. A spacious walk-out basement provides an opportunity for finishing more living space with a sliding glass door to access to the backyard. A new walkway and custom stonework enhance the front yard. For outside dining, there is a rear deck overlooking the 5+ private acres. Only a short drive to the town of Pine Plains makes this a convenient location with easy access to all local amenities. A great opportunity to make this your own home. Enjoy the sounds of nature in this country retreat!

Step into the timeless allure of an 1890 Eyebrow Colonial a 5-bedroom, 2-bath gem that surprises with its spaciousness and boasts remarkable wide board floors. Recently separated onto 3.53 acres, this home offers ample space for gardens, pets, and children to frolic. The Metro North Wassaic station is a mere 10 miles away, granting access to the vibrant yet serene lifestyle of Eastern Dutchess County. With its character-filled interiors, this residence captures the essence of charm. Engage in countryside delights like skiing, biking, hiking, top-notch dining, and the Millerton Movie House all just a short drive away. Discover this inviting home and its location, minutes from downtown Millerton.,AboveGrade:2328,Basement:Interior Access,Cooling:Attic Fan,Ceiling Fan,EQUIPMENT:Carbon Monoxide Detector,Smoke Detectors,FLOORING:Vinyl,Wide Board,FOUNDATION:Stone,Heating:Zoned,InteriorFeatures:Electric Dryer Connection,Electric Stove Connection,Walk-In Closets,Washer Connection,Level 1 Desc:KITCHEN, FULL BATH, DINING RM, LIVING RM, DEN/OFFICE, FOYER,Level 2 Desc:5 BEDROOMS, FULL BATH, WALK-IN-CLOSETS,Level 3 Desc:UNFINISHED ATTIC,Other School:PRIVATE,OTHERROOMS:Foyer,Library/Study,ROOF:Asphalt Shingles