355 houses for sale in Chester, Chester town Hampden County Massachusetts

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

Welcome to this historic Colonial home nestled in the center of Chester, offering charm and modern potential. Featuring 6 spacious rooms, including 3 generous bedrooms and 1.5 bathrooms, this home is ideal for Living, investors, or those seeking an Airbnb rental opportunity. Inside, enjoy the warmth of beautiful wood floors throughout most of the home, a large kitchen with ample counter and cabinet space, and closets galore for all your storage needs. Additional features include a spacious three-season front porch thats surrounded by natural light accented by a beautiful wood ceiling, vinyl windows, an attached 1-car garage, and a storage shed all situated on a 0.36-acre lot. Located along the scenic Westfield River, this property is a haven for outdoor lovers, with nearby hiking and riding trails, and is just a short drive to Jacobs Pillow, Tanglewood, Lee Outlets, and only 30 minutes to Westfield or the Berkshires

Charming 2-bedroom, 1-bath home tucked away in the peaceful Hill Towns, offering comfort, character, and a scenic natural setting. A beautiful stream runs along the rear of the property, and the small, manageable lot makes upkeep easy while still providing room to enjoy the outdoors. Inside, the home features bright, welcoming spaces ideal for simple, low-maintenance living. Whether you're looking to downsize or purchase your first home, this property is a must see!

Tucked away in a peaceful and private setting, this distinctive Octagon-style home offers an opportunity to enjoy country living on over 5 acres in scenic Worthington, Massachusetts, at the foot of the Berkshires. Built in 1991, and set off the beaten path, this property has 450' of frontage and is surrounded by natural beauty, stonewalls and a tranquil atmosphere. Inside you'll find over 2000 sf with an open floor plan, vaulted ceilings and abundant natural light. The kitchen, accented by granite countertops and open style cabinetry, flows seamlessly into the main living areas. Dining area with exterior deck, living room with woodstove, maple floors, mini split heating/cooling, and a full bath round out main level. Downstairs, you'll find 2 bedrooms, a full bath, an office and a laundry room.Whole house generator! Carport and shed for storage. This one-of-a-kind property is perfect as a year-round residence or a fabulous getaway

Tucked against hundreds of acres of protected forest, this beautifully preserved late 1700s Berkshire homestead offers a rare blend of historic New England character, thoughtful modern upgrades, and direct access to the outdoors. Rich in period detail, the home showcases authentic craftsmanship, including hand-hewn beams, wooden pegs, and square nails, timeless elements seldom found beyond true historic farmhouses. Beneath it all, a fieldstone foundation with an insulated rim joist has been professionally sealed, while recent improvements such as a fully insulated roof and comprehensive air sealing enhance comfort and efficiency throughout. Modern systems have been carefully integrated to support year-round living, including an energy efficient mini-split heat pump system providing both heating and air conditioning, a heat pump water heater, and a new 100-amp electrical panel. Hydronic heat remains in place as a reliable backup, offering peace of mind during colder Berkshire winters. T

Tucked into the woods of Sherwood Greens and just a short walk to Long Bow Lake's private beach, this home is the kind of Berkshire retreat you have been looking for. Set on 2.35 acres with privacy on both sides, it offers the peaceful, tucked-away feeling of a cabin in the woods while remaining just minutes from Lee and the Berkshires' renowned cultural attractions, including Jacob's Pillow, Tanglewood, and the area's vibrant restaurants, shops, and hiking trails. One of the community's greatest attractions is Long Bow Lake itself, a quiet non-motorized lake enjoyed by kayakers, canoeists, paddleboarders, and those seeking a more peaceful pace. Inside, cathedral ceilings, warm pine walls, and a wood stove create an inviting atmosphere that feels instantly welcoming. Offering 1,764 square feet, the spacious living room opens to the dining area, creating a comfortable gathering space filled with natural light and character. Sliding glass doors lead to a brand-new deck overlooking the su

Tucked into the woods of Sherwood Greens and just a short walk to Long Bow Lake's private beach, this home is the kind of Berkshire retreat you have been looking for. Set on 2.35 acres with privacy on both sides, it offers the peaceful, tucked-away feeling of a cabin in the woods while remaining just minutes from Lee and the Berkshires' renowned cultural attractions, including Jacob's Pillow, Tanglewood, and the area's vibrant restaurants, shops, and hiking trails. One of the community's greatest attractions is Long Bow Lake itself, a quiet non-motorized lake enjoyed by kayakers, canoeists, paddleboarders, and those seeking a more peaceful pace. Inside, cathedral ceilings, warm pine walls, and a wood stove create an inviting atmosphere that feels instantly welcoming. Offering 1,764 square feet, the spacious living room opens to the dining area, creating a comfortable gathering space filled with natural light and character. Sliding glass doors lead to a brand-new deck overlooking the su

Bult along the Middle Branch of the Westfield River. This cottage offers an open floor plan with some changes for access to the 2 back bed rooms and full bath. There is a sleeping loft accessed by ladder. Open Kitchen Dining Living are with cathedral ceiling. Wrap around porch has a easterly view of the river which is quite close by with dipping pools and the sound of running water. Needs clean up and some rehab and modification inside as well as outside. Newer roof, solid piers. Always served as a year round home

Tuttle Brook is in your back yard. This cottage is in need of complete renovation and clean out but a lot of what is there can be used. Large bed room, Bath, Open Kitchen Dining and living area with a fireplace and wood flooring. South facing entry porch with lots of windows has electric heater for use year round. Make a good little starter or summer cottage. Worth a look and worth the price. SOLD AS IS

Tucked away on a dead-end street in the foothills of the Berkshires, this thoughtfully designed Cape offers space, flexibility, and a setting that feels like a retreat. Set back on 2.73 acres with scenic views, the open floor plan invites easy everyday living and effortless entertaining. The main level features a primary suite with a private bath, walk-in closet, and its own balcony for quiet morning coffee or unwinding at the end of the day. A first-floor laundry room adds convenience, while the dining area flows into a kitchen with granite counters and seating-perfect for gathering and conversation. A home office or flex room completes the first floor, offering options for work, hobbies, or guests. Upstairs, you'll find four additional bedrooms plus access to a bonus space with a separate entrance from the garage-ideal for future expansion or creative use. The walk-out basement includes partially finished space with radiant floors, cold storage, and additional potential

Nestled in a magical woodsy setting on a lightly-travelled country road, this uniquely charming home is a standout. Designed and renovated with exceptional taste, enter the front door and you won't want to leave. The open-floorplan living area includes a gourmet kitchen, a gas fireplace, and access to a wide, screened porch overlooking acres of wooded privacy. The hallway off the entry foyer/mudroom leads past the powder room to the cozy primary suite. At the top of the open staircase you'll find a comfortable sitting nook between 2 more bedrooms and a second full bath. The lower level has a large finished room with another gas fireplace and the third full bathroom, perfect for use as a family room or fourth bedroom. There's also large separate storage. Only 10 minutes from the private Otis Community Beach

Nestled in a magical woodsy setting on a lightly-travelled country road, this uniquely charming home is a standout. Designed and renovated with exceptional taste, enter the front door and you won't want to leave. The open-floorplan living area includes a gourmet kitchen, a gas fireplace, and access to a wide, screened porch overlooking acres of wooded privacy. The hallway off the entry foyer/mudroom leads past the powder room to the cozy primary suite. At the top of the open staircase you'll find a comfortable sitting nook between 2 more bedrooms and a second full bath. The lower level has a large finished room with another gas fireplace and the third full bathroom, perfect for use as a family room or fourth bedroom. There's also large separate storage. Only 10 minutes from the private Otis Community Beach

Enjoy the best of the Berkshires from this beautifully maintained Contemporary Colonial, privately set on more than 2.5 acres with deeded access to Otis Reservoir, Massachusetts' largest recreational lake. Spend your summers boating, swimming, and fishing, then return home to relax in the peace and privacy of your own wooded retreat.Built in 2000, this spacious home offers four bedrooms and three full baths, including a first-floor primary suite with a private en suite bath. The open-concept living area features soaring cathedral ceilings, a cozy gas stove, and a seamless flow into the well-appointed kitchen, creating an inviting space for everyday living and entertaining. A generous screened porch overlooks the expansive yard, while the stone terrace and newer hot tub provide the perfect setting to unwind after a day on the lake or slopes. The finished lower level offers a comfortable media room or family room, providing flexible space for movie nights, games, or guests. An oversized

A very special 18th century authentic reproduction post and beam on a tranquil country road. One of the finer homes in Worthington set on just under six acres of peaceful forest. The home was built in 1976 with high-quality craftsmanship. The home is built with vintage integrity. Cedar siding with rosehead nails and hand split cedar shakes on the roof. Wide plank pine and cherry floors and stunning. The Cherry wall paneling was harvested from the property. The home is a saltbox style set back over 300feet from the road for the ultimate privacy. Amazing perennial gardens and Goshen stone paths, surround the home. There are three bedrooms and two full baths, The dining room and library have fireplaces with authentic granite hearths. There is a large artist wing that can be used for additional living space if needed. A large deck blends in with the surrounding nature and wildlife

A very special 18th century authentic reproduction post and beam on a tranquil country road. One of the finer homes in Worthington set on just under six acres of peaceful forest. The home was built in 1976 with high-quality craftsmanship. The home is built with vintage integrity. Cedar siding with rosehead nails and hand split cedar shakes on the roof. Wide plank pine and cherry floors and stunning. The Cherry wall paneling was harvested from the property. The home is a saltbox style set back over 300feet from the road for the ultimate privacy. Amazing perennial gardens and Goshen stone paths, surround the home. There are three bedrooms and two full baths, The dining room and library have fireplaces with authentic granite hearths. There is a large artist wing that can be used for additional living space if needed. A large deck blends in with the surrounding nature and wildlife

Loved by the same family for generations, this year-round Lake Damond waterfront property is ready for its next chapter. Offering 125 feet of lake frontage, this 4 bedroom, one bath home is tucked into a wooded setting for privacy while still providing plenty of open, sunny space to enjoy the water. The main level features an open living, dining, kitchen area w/ a bank of windows overlooking the lake, access to the expansive deck, 2 first floor bedrooms, a 1st floor bath w/ shower, and workshop/utility/storage room. Upstairs are 2 additional bedrooms. Outdoor features include swimming, non-motorized boating, dock, 3 outbuildings, and access to the association's private beach and play ground. Improvements include a metal roof, Well, replacement windows, and fuel oil tank. Property is being sold furnished and strictly AS IS, WHERE IS. Septic is operational but its assumed the system will need replacement. Cash buyer/rehab loan likely due to septic

Loved by the same family for generations, this year-round Lake Damond waterfront property is ready for its next chapter. Offering 125 feet of lake frontage, this 4 bedroom, one bath home is tucked into a wooded setting for privacy while still providing plenty of open, sunny space to enjoy the water. The main level features an open living, dining, kitchen area w/ a bank of windows overlooking the lake, access to the expansive deck, 2 first floor bedrooms, a 1st floor bath w/ shower, and workshop/utility/storage room. Upstairs are 2 additional bedrooms. Outdoor features include swimming, non-motorized boating, dock, 3 outbuildings, and access to the association's private beach and play ground. Improvements include a metal roof, Well, replacement windows, and fuel oil tank. Property is being sold furnished and strictly AS IS, WHERE IS. Septic is operational but its assumed the system will need replacement. Cash buyer/rehab loan likely due to septic

Discover the potential of 75 Lead Mine Rd, a beautifully restored home in the serene town of Southampton, MA. While offering peaceful natural surroundings and easy access to local amenities and major routes, this home has been thoughtfully rebuilt from the ground up.Inside, you'll find all-new plumbing, electrical, and an updated layout that maximizes comfort and functionality. The new kitchen and master suite blend modern convenience with timeless appeal, while a spacious bonus room above the garage offers endless possibilities for work, play, or guests. Comfort is ensured year-round with a high-efficiency mini-split system, and every wall has been pray-foam insulated for top-tier energy efficiency.All of this has been achieved while carefully preserving the original charm of the home, creating a perfect balance of history and modern living. This property represents a unique opportunity to enjoy the quiet beauty and community spirit of Western MA in a home that truly feels brand new!

Tucked away on just over 6 private acres, this custom executive ranch offers a rare blend of luxury, comfort, and natural beauty. Designed for easy one-level living, the home features 3 bedrooms and 3 full bathrooms, including a serene primary suite with a clawfoot soaking tub and tiled walk-in shower. A stunning chef's kitchen anchors the home with quartz countertops, stainless steel appliances, and thoughtful custom finishes. Warm, inviting living spaces are complemented by a Vermont Castings wood stove, while mini splits provide year-round comfort. A spacious bonus room over the garage with a full bath offers flexibility for guests, a studio, or a home office. Outdoors, enjoy a screened porch, outdoor shower, hot tub, mature fruit trees, and fenced acreage. A peaceful nature retreat and wildlife corridor weave through the property, creating a quiet sanctuary with approximately 2.6 acres offering potential for future subdivision. DEADLINE FOR OFFERS- 5-27-26@3:00 PM

Beautifully refurbished home in the Berkshires with deeded rights to the White Lily Pond Association, offering access to a private beach, tennis and pickleball courts. White Lily Pond is a quiet lake ideal for canoeing, kayaking, paddleboarding, and trolling motors only. Renovated with quality craftsmanship throughout, the home features upgraded insulation, efficient propane heat, and inviting living spaces. The custom kitchen includes granite countertops, a large island, gas range, and custom cabinetry. The living area is highlighted by a fireplace with handcrafted custom sconces. Otis Ridge Ski, Jacobs Pillow, Tanglewood are within minutes of home. A perfect year-round home or Berkshire getaway in desirable Otis

Originally built in the 1700s, this historic post-and-beam barn has been thoughtfully renovated over time while maintaining its unique character and charm. A recently installed solar energy system allows for highly efficient living with the potential for an off-grid lifestyle. The home features an open floor plan filled with natural light from numerous oversized windows. A chef's kitchen adjoins the dining area, creating an ideal space for entertaining. With three full floors of living space, the home offers four ensuite bedrooms plus an additional bedroom, providing comfort and privacy for family and guests. Enjoy seamless indoor-outdoor living with a screened porch off the main level leading to spacious decks and a hot tub. The lower level includes a media room and sauna for relaxation

Private sanctuary nestled in the woods on 2.34 acres with stream and just minutes to the lake. This open floor plan contemporary offers 3 bedrooms and 2 1/2 baths. One bedroom with full bath is located on the first floor and two upstairs with a second full bath. Soaring and dramatic cathedral ceilings open to a cozy loft room above which is perfect for a den or home office. Giant sun room off the back has skylights and lots of glass to let the outside in. Sliders to a large deck for entertaining, finished room in the basement makes great game room with work shop. Storage shed, pellet stove in living room, wood stove in basement. Three newer heat pump mini-splits for heating and cooling (AC). Get away from the madness of the world and enjoy nature at your secluded, wooded lot. Just a short drive or walk to a sandy beach for swimming at the lake

Originally built in the 1700s, this historic post-and-beam barn has been thoughtfully renovated over time while maintaining its unique character and charm. A recently installed solar energy system allows for highly efficient living with the potential for an off-grid lifestyle. The home features an open floor plan filled with natural light from numerous oversized windows. A chef's kitchen adjoins the dining area, creating an ideal space for entertaining. With three full floors of living space, the home offers four ensuite bedrooms plus an additional bedroom, providing comfort and privacy for family and guests. Enjoy seamless indoor-outdoor living with a screened porch off the main level leading to spacious decks and a hot tub. The lower level includes a media room and sauna for relaxation

Welcome to 15 Tiffany Lane, a great opportunity for those looking for single level living, in a quiet location, a short drive from Northampton Center, Florence and Easthampton on over an acre of land. Nestled above a scenic cul-de-sac, this 3bdrm/2ba ranch style home offers more space than expected due to a large addition that opened the kitchen to a spacious and sunny living/dining/family room. This addition has a vaulted ceiling, skylights and opens onto a large deck overlooking the backyard. Step outside onto the composite deck, to the patio or into the handsome gazebo. Inside, hardwood floors shine throughout the main living area including another dining/family room and primary suite w/private bath. Additionally there are 3 finished bonus rooms in the basement. Conveniences include central a/c, in-ground sprinkler system, solar panels and a large garden shed. The attached 2 car garage offers ease of access. Relax and enjoy the rural setting of this peaceful home in Northampton