Monterey MA Real Estate & Homes for Sale

Nestled in one of the most desirable areas of Western Massachusetts, this spacious 4-bedroom, 3-bathroom post-and-beam home offers the perfect blend of rustic charm and modern efficiency. Thoughtfully designed with exposed wood beams, cathedral ceilings, and skylights that flood the interior with natural light, this property exudes warmth and character throughout. Set on a serene lot that abuts the Federally Protected Appalachian Trail Corridor, nature lovers will find peace and privacy just steps from their door. Enjoy the benefits of green living with the home's electricity powered by a nearby solar farm at Weston Abbey-a rare and sustainable perk. The home features a partially finished basement ideal for a home office, gym, or creative studio, offering flexible space for work or play. With a Great Barrington mailing address, but home is located in Sheffield giving residents lower Sheffield taxes -plus the ability to vote in Sheffield. Conveniently located just minutes from Guido's Fresh Marketplace, shops, restaurants, and outdoor recreation, this exceptional property is a true gem that combines tranquility, community, and eco-conscious living.

GRACIOUS IN-TOWN LIVING IN THE SOUTHERN BERKSHIRES This gracious vintage home has been thoughtfully renovated and lovingly maintained by the current owners for over 20 years. High ceilings, wonderful light, spacious rooms, a ''walk to everything'' in town location, and residential/commercial zoning provide comfort and unlimited possibilities. A 1,000 sq. ft. outbuilding with water & electric service adds more potential. Beautiful period detail combines with with modern updates-crown molding, soapstone counters, farmer's sink, cherry cabinets, a built in hutch, wood & tile flooring, a South facing bay window, French doors, a large 1st floor Laundry Room, new water heater, and new septic are just the beginning. The large, private room above the Garage is an ideal Studio or Office. There is so much to enjoy here-come see for yourself!

Attention investors! Nestled on a peaceful 1-acre lot, this 2 bedroom, 2 bath Cape provides warmth, character, and opportunity! A spacious kitchen, with adjoining pantry, and dining area provides plenty of room for gathering. The inviting living room features exposed beams and a brick hearth, perfect for a wood or pellet stove. The first floor includes a bedroom, laundry and full bath, while upstairs boasts a large bedroom, another full bath and a versatile landing area. Outside you will find an oversized shed with ample storage, perfect for tools, equipment or hobby space. With major updates already done by the owners of 23 years, this home is ready for your personal touch. A little vision and TLC can transform it into the perfect starter home, cozy getaway or AirBnB! A short drive to Great Barrington. Don't miss out! Newly adjusted price.

Nestled in the foothills of the Berkshires on a quiet country road, this circa 1790 colonial, "The Tobey House," awaits its new stewards! This special property features authentic period details & is sited on a majestic 3.88 acre lot with direct access to the waterfalls at Campbells Falls. The sprawling, versatile floorplan is the perfect canvas to bring your antique Pinterest board to life! With windows in all the right places, the home is awash in natural light that perfectly showcases the rich patina of the wide plank flooring and rustic detailing throughout. Entering the architect-designed kitchen, you'll take a deep breath: this is truly a HOME. Cabinet packed with a large granite island overlooking one of 7 (4 functional) original fireplaces, it creates the perfect command center. Built-in enthusiasts will marvel at the absolutely stunning carpentry in every room. An XL dining room flows seamlessly into a charming den. The lovely center hall provides access to the ultimate work from home wing, guest room with ensuite 1/2 bath, & a fantastic covered porch overlooking the pastoral grounds, former pool area w hookups still intact, & massive barn. Upstairs, the capacious primary BR is adorned with hand-stenciled walls. 2 addl well sized BRs share a massive full bath w laundry. Ideal location on MA line - the perfect launch point to enjoy the best of the Berkshires & NW corner. This home's rich heritage is ready to converge with your next chapter: a dream homestead beckons!

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.

It's no wonder why this property is the home of Berkshire county's oldest elm tree! The abundant sunshine, quietude and peace would make anybody want to set down roots and stay a while. This light filled home has refinished wood floors throughout the main level. Kitchen has granite counters, ample cabinet space, pantry and large island. As part of the open floor plan there is a bright dining room and living room area that opens to an expansive composite deck. The great room has endless mountain views, river views and a welcoming fireplace. The lower level also has a main floor bedroom, laundry, office and lots of closet space. Upstairs is the spacious primary bedroom with private bathroom and exterior balcony overlooking horse pastures. There is a third full bath, two additional bedrooms and bonus room. This property really comes alive outside! The two stall barn is in excellent condition. Stalls are 12x12 with electric and frost free hydrant, tack/feed room. Exterior access to two private paddocks that open into a lush pasture. Barn also includes equipment area, workshop and RV parking space or use this space as a run in for livestock. The home is surrounded by mature gardens and hardscapes. Walkout basement has slider to a stone patio area and a fireplace. Could be spectacular extra living space. Home is complete with an invisible fence system for your pups and whole house generator. Horse property, waterfront and views this property is it!

Nestled in the heart of the completely private 1700 acres of the Doolittle Lake Company woods on 2 parcels, this 100 acre 5,670 sq ft beautifully maintained 1780 center hall colonial boasts colonial & art deco architectural details. Moved to its current location in the 1930s NY architect Robert Carrere renovations include generous reception rooms, wide red pine floors, high ceilings, 2 wet bars, 9 wood burning fireplaces. Rotary dial phones, butler bells, & other period details capture the charm of the 1930s. Gourmet kitchen with fireplace custom cabinetry, a fish sink on the back porch for cleaning trout! Elegant sunny dining room & breakfast terrace with herb garden. Sun porch glass doors open to stone walled perennial gardens & pool. Dramatic arches & vaulted ceiling adorn the poolhouse with kitchenette, 1/2 bath, dressing rooms & outdoor shower. Custom oval gunite heated pool. Main bedroom with private sitting area, fireplace & steam shower, 3 large ensuite bedrooms with fireplaces, playroom and laundry on upper floor. Ensuite studio above heated garage. Ownership includes all benefits of hunting, fishing, boating, hiking in this private community on pristine lake & pond. Available caretaking service make maintaining this beautiful home stress free. Enjoy year round peaceful lake area living on unique private estate in gorgeous Doolittle Lake Woods located 2 1/2 hours from Boston or NY. Agent Owned.

Tower Hill house sits on 7 acres with 800 feet of frontage along the western shore of Doolittle Lake in Norfolk, CT. Designed by a local architect and built by local craftspeople, the house is privately sited down a long driveway and sits on a little bluff so there are lovely views over the lake. The Doolittle community takes great care to protect the health of the lake and its surrounding woodlands. Hiking, swimming, kayaking, canoeing and sailing (no motor boats allowed) are among the fun and healthy things to do and town is only a few minute car ride away.

A remarkable opportunity to combine residencial on the second floor with commercial on the main floor in an excellent location with plenty of private parking. The kitchen is set up for the discerning chef , a large dining room, a bedroom/office and living room with a propane fireplace completes the first floor. The gorgeous hardwood floors throughout the house have just been finished and the house is in pristine shape for the next owner. Finally, there is central air on the second floor to complete the full package!

Charming 5-Bedroom Village Colonial in the Heart of North Canaan Located in a desirable sidewalk neighborhood, this beautifully renovated Village Colonial combines classic charm with modern updates. The home features newly updated electrical and plumbing systems, replastered and lathed walls, freshly refinished main-level floors, all-new bathrooms, and a fully remodeled kitchen. Freshly painted throughout, it is ready for you to move right in. From the spacious front porch, enter into a gracious foyer and enjoy an open, airy layout perfect for family living and entertaining. Large, sun-filled rooms lead to a modern kitchen with direct access to a deck and lower patio, ideal for outdoor dining. A versatile first-floor study creating a great home office space. The walk-up attic provides potential for additional living space or a creative studio. The beautifully landscaped backyard is a private oasis with a lawn, gardens, mature fruit trees, and year-round flowering plants. Conveniently located close to ski resorts in Massachusetts and within walking distance to local amenities like the pharmacy, post office, library, grocery stores, playgrounds, and a lifeguarded town beach, this home can be both a tranquil retreat and easy access to everything you need. Make this charming home yours today! The owner has completed beautiful renovations throughout the home, enhancing both its charm and modern functionality. Room sizes are approximate. New furnace installed 1/15/25

Welcome to this classic 3-bedroom Colonial, ideally situated on the outskirts of town yet just a short stroll to the sidewalk district. This home blends timeless charm with functional living spaces, perfect for families or anyone looking for a comfortable setting with easy access to town amenities. Step inside to discover hardwood floors that flow throughout the home, adding warmth and character to every room. The dining room features crown molding and a built-in hutch. Upstairs, you'll find three bedrooms and a full bath. One bedroom opens to a large enclosed porch-perfect for a cozy sleeping porch, sunroom, or playful retreat. A convenient half-bath is located on the main floor for guests. Enjoy your morning coffee on the welcoming front porch, or unwind after a long day. Two car detached garage with extra space in the back currently used for chickens. New house roof. This home is full of potential and charm-don't miss the chance to make it your own! New septic will be installed prior to closing. Contingent on Seller finding home of choice. All room measurements are approximate.

Nestled along Greenwoods Rd. W., this charming 1,032 sq. ft. Colonial offers a cozy and functional layout with thoughtful updates. The first floor features a modest eat-in kitchen with a spacious pantry that conveniently accommodates laundry, a versatile living room with space for a dining area or office nook, and a full bath. Upstairs, you'll find two comfortable bedrooms, each offering generous closet space. This home boasts several mechanical upgrades, including a newer heating system and oil tank, a brand-new hot water heater, and a roof that is approximately 10 years old. Additionally, a generator transfer switch adds peace of mind. If you choose the front bedroom, you'll enjoy the seasonal sounds of the Blackberry River just across the street, adding to the home's tranquil charm. Ideally located with easy access to North Canaan and the best of the Berkshires, this property provides both convenience and a picturesque setting. Don't miss this wonderful opportunity!

Opportunity Knocks! This 2-bedroom single-family home offers great potential for the right buyer. Nestled on a small lot near Route 44, the property features a finished lower level, 2-car garage, and the soothing sound of a nearby river. Located on a no-through street with city water and city sewer. Home needs rehab-bring your vision and ideas to make it shine! Owner says sell-don't miss out on this value-packed opportunity!

BEACON Cottage is a rare board and batten, Carpenter Gothic Modern Victorian. This stunning home is tucked away on Beacon Lane in Historic Norfolk Ct. It's open modern open concept is enhanced with stunning wood floors, period detailing and upscale amenities The private screened in porch offers views of lush grounds, flower gardens, and specimen trees that afford private country living just blocks from the historic village of Norfolk. The home offers offers 2 bedrooms and 2 baths with possibilities of more. A spacious greatroom with built ins,fireplace, open staircase,, walkout basement and a drive under garage make this property ideal for year round living or country a retreat. Shown by apointment only.

Welcome to this beautifully maintained 3-bedroom, 1 full bathroom, 2 half baths home located in a well-established "Green Acres" neighborhood just minutes from town. With a freshly painted exterior, this home boasts great curb appeal and a warm, inviting presence. Newly painted exterior, new furnace installed in 2024, tons to offer. Additional room in the basement, which includes a 1/2 bath. 19 miles to the Metro North Wassaic Train Station and just 14 miles to Great Barrington, MA.

Classic 3-Bedroom Cape with Pool Perfectly positioned between NW Connecticut and Sheffield, MA in the Berkshires. Sheffield is the oldest Town in Berkshire County - the township was purchased in 1724 from Chief Konkapot and other Stockbridge Native Americans. This bright, lovely 3-Bedroom Cape features a beautiful, heated pool, a Bedroom and Full Bath on the Main Floor, 2 Bedrooms and another Full Bath on the Second Floor, a light and bright Living Room with stone fireplace, Kitchen with large island, Dining Room, and a 2-bay Garage with loft. Tall lilacs trees frame the pool on this 1-acre parcel. Close to private schools, skiing, the Appalachian Trail, and Twin Lakes. A sweet spot to make your home whether for year-round living or part-time relaxation.

PRICE REDUCTION! Motivated seller, bring all offers!!! Located on a quiet cul-de-sac this home is waiting for you! Green Acres Community is North Canaan's best kept secret! This 1987 spacious Saltbox with hardwood floors sitting on almost an acre has been recently updated with kitchen appliances, bathroom vanities and fixtures, new propane furnace, washer/dryer, hot water heater, water filtration system and home generator. The large living room could easily have a sitting area, office. The finished walk out basement has a half bath and laundry room and provides another space for a rec or family room or potentially a third bedroom/in-law suite. The wood stove adds warmth to your winter nights. Fiber optic ready for those that work from home. The large wrap around deck, 817 square feet, provides plenty of space for outdoor activities, grilling and get togethers. The quiet neighborhood is conveniently located to public and private area schools, main street shopping, and all of the entertainment that Great Barrington, MA has to offer. Nearby amenities include Amazing restaurants, Twin Lakes, Catamount Ski Area and Ski Butternut, and plenty of hiking along the Appalachian trail. 30 minutes to the Wassaic train station, 2 hours commute to New York City. This home is move in ready. Come take a look and explore all that it has to offer. Make it yours. Motivated seller, bring all offers

Seize the best value on Twin Lakes! Compare this stunning Salisbury estate to the recently sold 29 Morgan Lane and discover unparalleled luxury at an extraordinary price. Nestled on the tranquil shores of East Twin Lake, this masterpiece blends Adirondack charm with modern elegance, offering breathtaking views, grand living spaces, and exquisite craftsmanship. This home is a testament to visionary design, nestled on 2 acres with a private sandy beachfront. The expansive Great Room, with its walnut floors, oak paneling, and regal coffered ceiling, is a celebration of artisanal detail and serene lake views. The second floor is a retreat of luxury, offering a grand Primary suite, two additional ensuite bedrooms, and a laundry room for utmost convenience. The third floor extends the living space with a flexible area for entertainment or guest quarters. The outdoor experience is enhanced by a gazebo with a fireplace and an infinity spa, all set against the dramatic backdrop of the lake and mountains. This home's grandeur is matched by its robust infrastructure, ensuring a legacy of beauty and comfort, all within easy reach of superior private schools and only two hours from NYC. Full Bath included with the flex space on the third floor. The basement has approx. 2500 sq ft of partially finished space with a full bath, laundry connections, and a boat garage. Don't miss this rare opportunity to own the pinnacle of lakeside living-schedule your private tour today!

The post-and-beam residence showcases soaring ceilings and expansive windows that frame the spectacular landscape while highlighting the architectural character throughout. Natural materials-including local woods, native stone, and artisanal steel elements-create a sophisticated dialogue between interior spaces and the surrounding countryside. The heart of the main level features a grand Great Room anchored by a floor-to-ceiling stone fireplace, flowing seamlessly into a gourmet Chef's Kitchen with double islands and custom cabinetry. An elegant staircase serves as a natural divider between living areas, while French doors open to a spacious patio overlooking the pastoral grounds, historic barns, and mountain vistas beyond. The thoughtful floor plan includes a main-level with 3 en suite bedrooms, a library, and formal sitting room accessible from the gracious entry hall. A classic New England mudroom provides practical transition space for all seasons. The second level offers 2 primary bedroom suites plus two charming office spaces with northwestern mountain views. A custom steel staircase ascends to a serene meditation loft, creating a private retreat. The finished lower level opens directly to the landscaped side yard, featuring fieldstone walls that echo the property's agricultural roots. Several outbuildings, including a substantial barn, await their next chapter and offer a blank slate for the country hobbiest.

Clarion Farm is an iconic French Country Estate & Horse Property in Salisbury, CT. It is a serenely private retreat with a 4-bedroom main house, a Studio on 16.25 acres, and a Horse Property on 30.72 acres for a total of 47 acres only a few minutes from the village of Salisbury and 15 minutes into Great Barrington. This exquisite property seamlessly blends tranquility with sophistication, creating an unparalleled living experience. Every aspect has been thoughtfully crafted to ensure maximum comfort and well-being, making it a true haven of peace and French Country Casual Luxury. All rooms are generously sized and flow beautifully into one another. The stunning private stone-walled pool courtyard is perfectly situated on the professionally landscaped property. Clarion Farm has a 12 Stall Horse Barn, a 6 Stall Barn, an Indoor 80 x180 Indoor Riding Ring, a 100 x 200 Outdoor Riding Ring, 6 Paddocks, and a 2 Bedroom Barn Apartment. Ideally situated near the many private & public schools, Catamount Ski Area and Aerial Park, and the villages of Salisbury, CT, Millerton, NY, Great Barrington, MA, and Wassaic Train Station. This listing includes two parcels: 10 N. Beaver Dam Road (Parcel ID: 2408134) and 471 Undermountain Road (Parcel ID: 2769378), with acreage and taxes reflective of both properties.

Minutes to Great Barrington, this 300 acre wilderness provides waterfalls, stream frontage, pond frontage and something for every outdoor enthusiast. Own your own mountain with trails throughout for hunting, hiking and camping. Build your dream house overlooking a stocked pond and classified trout stream while staying in the 3 bedroom 3 bath caretakers house. The possibilities are endless. Swim all summer in your own pond. Pull a trophy buck in the fall. Hike to the peak and back country ski down in the wintertime. Be the first to catch a trout in your own private trout stream.

Beautiful home in a great location. House is heated by wood and is very comfortable. Great location to town-updated kitchen. Basement is amazing-lots of great space! COME LOOK!

A Premier Estate Parcel Ready for Immediate Construction This exceptional 33.9 acre property on Beaver Dam Road-one of the most scenic addresses in Salisbury-offers a rare opportunity to create a private estate of lasting beauty and value. Surrounded on two sides by protected land, the property enjoys a remarkable sense of privacy and quiet, while being just minutes from the town center. The land itself is a harmonious blend of open hayfields and mature trees, highlighted by a historic copse originally commissioned over a century ago by Frederick Law Olmsted, the renowned landscape architect of Central Park. The setting is both pastoral and refined, with long views, curated plantings, and a serene natural character that evolves beautifully through the seasons. Over the past two years, the current owners have undertaken an extensive series of improvements. A private homesite has been carefully positioned deep within the property, far from the road, offering the ideal location for a one- or two-story residence. A foundation has already been poured, and all the essential infrastructure is in place-underground electric, a high-yield well, approved septic systems for both the main house and a separate carriage house, propane tanks, and whole-house generators-allowing for immediate construction. Every detail of this groundwork has been completed to the highest standards.

Enter through the Mahogany front door to the 1st floor featuring Fir wood floors, crown molding, and 11' ceilings setting the tone for this luxury home. The living room offers a fieldstone wood-burning fireplace, coffered ceilings, and sliding glass doors to a Lakeview porch. Adjacent is a kitchen with Shaker cabinetry, quartz countertops, a tiled backsplash, high-end appliances, and a central island. The butler's pantry adds convenience with an ice maker, dishwasher, and extra storage. Outdoor spaces include a dining porch with a fireplace, a screened porch, and an expansive open-air porch with Mahogany decking and stainless-steel railings. Upstairs, two serene primary suites feature lake views, vaulted ceilings, walk-in closets, and luxurious en-suite baths with soaking tubs, oversized showers, and quartz vanities. A media room and two additional en-suite bedrooms with lake views and elegant finishes complete the 2nd level. The finished lower level includes a mudroom, laundry room, game room, multipurpose space, and full bath, with walk-out access to the lake and a state-of-the-art, salt water, self-cleaning, heated gunite pool. Additional features include a boat launch and lakeside gazebo on Twin Lakes. The property also boasts a heated two-car attached garage as well as a 4-bay detached garage, perfect for your car collection, the ultimate party barn or sports or court venue. 13 heat zones, 6 cooling zones, radiant heat throughout, granite accents, & an irrigation system.

Welcome to your potential new home in the charming town of Falls Village, Connecticut! This delightful house in Litchfield County combines a perfect blend of comfort and convenience, making it an ideal choice for those seeking a peaceful retreat with easy access to various amenities. As you step inside, you'll be greeted by an inviting entry foyer with a stylish tile floor and a stairway leading to the second floor. The fully equipped country kitchen is a dream come true for any home chef, featuring quality cabinetry, a convenient breakfast bar, and a pantry for all your storage needs. Whip up your favorite meals while chatting with family or entertaining guests in this warm and welcoming space. Adjacent to the kitchen, you'll find a cozy dining room that opens up to a delightful three-season room. This charming space boasts a vaulted wood-paneled ceiling, a ceiling fan for those warm summer days, and direct access to a beautiful bluestone patio. Imagine sipping your morning coffee while enjoying the serene outdoor views or hosting memorable gatherings with friends and family in this versatile area. This spacious home has four large bedrooms, providing ample room for family members or guests. The full basement, accessible from both inside and outside the house, affords additional storage or the potential for a future recreation area. Throughout the home, you'll appreciate the abundance of natural light that creates a bright and airy atmosphere.