Pittsfield MA Real Estate & Homes for Sale

Nestled in the heart of the Berkshires, this historic Richmond compound presents a rare blend of colonial charm and modern equestrian excellence. Spanning 11+ bucolic acres with sweeping pastoral views, the legendary c1776 estate boasts a meticulously maintained main residence, three enchanting cottages, and the potential to include the region's premier full-service equestrian facility (see related listing for $2.25m and ask for pictures). The main residence, a testament to time-honored craftsmanship, features 7 bedrooms and 7.5 baths, each room telling a story of centuries past. The inn's dignified presence is complemented by a dining room, entrance parlor, library, den, period greenhouse, and a well-appointed kitchen that cater to both intimate family gatherings and grand celebrations.

Charming 2-bedroom, 2-bath single-family home with 1,071 sqft of living space on a 6,098 sqft lot. Built in 1900, this home features a newly reconditioned chimney and a new outdoor oil tank. Enjoy peaceful creek access with outdoor fencing removed. Heating includes oil and baseboard with a brand new furnace and hot water heater-no central AC. Unique septic setup with a tight tank for the toilet and a grey water system for the shower. A rare opportunity to own a well-maintained home with modern updates in a serene setting.

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.

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.

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!

Straight up the Taconic Parkway, just 2.5 hours from Midtown, your driveway is barely noticeable -- but you know what lies beyond - safety, serenity, and seclusion. Unlock the gate, drive through the woods, and prepare to experience a different kind of rush hour - tracking big buck or flushing wild pheasants or raucous turkeys. Better still, just rest and relax on your ultra-private 223+ ac retreat on the hillsides of the Hudson River. Your driveway reveals nothing to the rest of the world about the lovely accommodations that await in the custom-built, true-log home. Outdoor enthusiasts or those just looking for a unique family or group retreat in the Hudson River highlands will find it here. The grounds of the home are well-maintained with landscaping around 2 ponds, and ample parking, plus a 500 sq ft double-door equipment barn. Enter the home and take in the cathedral-like lodge with an open living-dining-kitchen space anchored by a massive 25 foot floor-to-ceiling fieldstone wood burning fireplace. True log walls and rich pinewood floors throughout the home add strength and character in every room. The kitchen, where everyone gathers, is open to this lovely space, with a great seating peninsula, ideal for travelers and wilderness voyagers to sit while the feast is prepared. 2 bdrms on main floor, off kitchen w a shared full bath. Upstairs, a master suite w private bdrm ( massive closets ), full ba, & loft overlooking fireplace. Full basement nicely finished w bonus room ideal for a pull-out couch / guest room, laundry and work area, + .5 bath. Don (or shed) camo, boots, and parkas while still in the comfort of the lower level. There is ample storage, with drive-out doors! Whole house AC. The property is tax-advantaged with ag AND NYS Section 480-a Forest protections. The main driveway covers more than a mile as it curves through the property. Miles more off-road trails provide further access to the parcels, including the 5 high-mounted blinds. Actively managed farm fields, also within the property boundaries, mean ready-made access is waiting for your next ATV adventure.Enjoy this masterpiece along the hills of the Hudson!

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.

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!

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.

CANAAN VALLEY LUXURY - The total renovation of this beautifully located single level home, rebuilt from the foundation up in 2024, has been done with unparalleled taste and style. Set just above the Whiting River and overlooking preserved land in an area of estate level properties, the serenity and timeless appeal of Canaan Valley surround you. The result is a virtually new home that is offered fully furnished and designed for comfort, sustainability, and easy maintenance. The 950 sq. ft. separate Studio building, with its own newly done interior, offers multiple options with a Kitchen, Bath, Living Room and Bedroom, all ideal as a guest apartment, office, or studio space. Unique choices of the highest quality are evident throughout. Tilt in windows from Germany, Hansgrohe fixtures, custom Italian lighting, quartz, porcelain, and marble surfaces. Luxury vinyl plank flooring, Hardie Board siding, and Trex decking for durability. The screened porch, deck, and inground pool with pool house are delightful. New Bosch heating and cooling, new 5 bedroom septic, all new wiring. There is so much to enjoy in this ideal retreat - come see for yourself!

This is a unique chance to enjoy stunning views of Bear Mountain from a contemporary home featuring expansive windows that showcase the scenery, set on nearly 20 acres that stretch across Salisbury, CT, and Sheffield, MA. The bright sunshine and lofty ceilings, along with a screened porch and two upper-level decks, seamlessly blend indoor and outdoor living in this lovely residence. The open-concept kitchen, living room, and dining room exude grandeur thanks to the breathtaking views and high ceilings. Completing the first floor are a library and a convenient powder room. On the upper level, a balcony landing equipped with bookcases and a desk forms a sunlit study area. The primary suite boasts its own full bath and a private balcony offering mountain vistas. Additionally, there are two more bedrooms that share a full bath. A detached two-bay garage includes a basement wine room. Located minutes from Great Barrington, Massachusetts and the cultural attractions of both the Berkshires and Litchfield Hills, this rare offering provides both privacy and convenient access to regional amenities. An extraordinary opportunity to own a contemporary retreat with unparalleled Bear Mountain views in one of New England's most scenic border regions. (CT 8 acres & MA 11.67 acres)

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!

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.

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

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.

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.

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.

Tucked away on a private road with shared lake access to the serene waters of Lake Washinee, this custom one-level home offers the perfect blend of natural beauty, thoughtful design, and modern comfort. Set on just over three wooded acres with a tranquil stream, the property offers privacy and peaceful surroundings in every direction. The original home was built in 1950. There was a complete renovation and additions to the home in 2003, enlarging the home significantly. Step inside to discover vaulted ceilings, hardwood floors, and skylights that flood the home with natural light. The spacious primary suite is a true retreat, featuring a large bedroom with a distinctive triangular balcony, large bathroom with a hot tub and walk-in shower, a walk-in closet, and a convenient laundry room-all on the main level. Designed with indoor-outdoor living in mind, the home boasts a large covered deck perfect for entertaining or relaxing in any season. Just steps away, an inground pool with its own covered lounge area invites summer enjoyment. The lower level includes a private bedroom with half bath and its own entrance-ideal for guests, a home office, or rental potential. A walk-out basement and one-car garage offer additional storage and the opportunity to expand your living space.

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.

Welcome to Owls Nest - a peaceful and private retreat tucked away on over 5 acres in the hills of North Canaan. This beautifully maintained colonial offers 4 bedrooms, 3.5 bathrooms, and timeless charm throughout. Upstairs, all bedrooms feature hardwood floors, while the main level boasts 2 wood-burning fireplaces, a spacious living room, a formal dining room, and a cozy study with a stunning stone hearth. The kitchen includes an informal dining area and plenty of storage, making it perfect for both everyday meals and entertaining. It is a chef's delight. Dual ovens with air fryer, induction cook top, stainless hood and a natural live edge wood top. Step outside to enjoy your screened-in porch with ceiling fans, a large private deck with a hot tub, and a tranquil backyard surrounded by nature. The walkout lower level is fully finished with a full bath, an extra kitchen, and a bonus storage room ideal for a wine cellar. Additional features include a walk-up attic, central vacuum, ceiling fans, and garden spaces that attract gentle wildlife like deer, owls, and turkeys. Located on a quiet street and just minutes from skiing, golf, Lime Rock Park, fine dining, and cultural events, this home offers year-round enjoyment or a perfect weekend getaway. Lovingly cared for and thoughtfully updated by its current owners.Don't miss the chance to own one of North Canaan's most serene and special properties. SqFt includes 1340 sqft in finished/heated walkout lower level.