847 properties for sale in Chester town, Hampden County Massachusetts

Tucked well back from the road on 3.5 private acres, this modern, lightly used home offers an effortless blend of low-maintenance living, single-story convenience, and quintessential Berkshires charm. Designed with an open, light-filled layout, the main level features gleaming hardwood floors and an seamless flow throughout the common living areas. At the heart of the main floor is a inviting living room with a gas fireplace framed by a stone surround and hearth, an updated kitchen, and a generous primary suite complete with a large walk-in closet.Enjoy indoor-outdoor living with a covered front porch, a spacious screened porch, and an expansive wrap-around deck perfect for entertaining or taking in the peaceful surroundings.The expansive finished walk-out lower level extends your living The expansive finished walk-out lower level extends your living space, equipped with cozy radiant heated floors, high-efficiency boiler system, and a flexible unfinished bonus room ready for custom exp

Impeccably maintained contemporary home set on four manicured acres bordering Massachusetts Fish and Game conservation lands and surrounded by approximately 4,500 acres of protected land in Hinsdale. Enjoy a private, serene setting just 1.6 miles from 287-acre Ashmere Lake. Inside, open entertaining spaces blend seamlessly with quiet retreats. The main level features a designer kitchen with granite countertops, Wolf range, and breakfast bar flowing into the dining area. A light-filled great room with gas fireplace offers year-round comfort, while a three-season screened porch and expansive decks invite outdoor dining. Three bedrooms include a first-floor primary suite with attached office or reading room. Additional highlights include 2.5 baths, laundry room, oversized two-car garage, and a massive basement with workbench and abundant storage. Just 30 minutes to Tanglewood, under 3 hours to Boston, and just over 3 hours to Manhattan

Tucked away on a serene and private lot just minutes from the sparkling waters of Otis Reservoir, this stunningly renovated 5-bedroom, 3-bath Colonial offers the perfect blend of luxury, comfort, and natural beauty. Designed for both elegant entertaining and everyday living, the heart of the home is the spectacular chef's kitchen featuring quartz countertops, abundant cabinetry, and refined finishes throughout. The thoughtfully designed 1st flr offers a formal living room, sophisticated dining area, two spacious bedrooms, and a beautifully updated full bath - ideal for guests or flexible living arrangements. Upstairs, retreat to the luxurious primary suite complete with a private ensuite bath, along with two additional generously sized bedrooms and a third full bath. Surrounded by peaceful nature views, trails and exceptional privacy, this remarkable property is a rare opportunity to enjoy upscale living in a tranquil setting to enjoy all the beauty the Berkshires have to offer

Impeccably cared for and thoughtfully maintained, this sprawling ranch offers comfortable one-level living with a flexible layout and plenty of space both inside and out. The sun-filled living room welcomes you with abundant natural light and a wood-burning fireplace, creating a warm and inviting gathering space. There is a well-appointed kitchen and dining room, while a bright and peaceful sunroom provides the perfect spot to relax and enjoy the surrounding setting. The home features three bedrooms, including a primary suite with a recently remodeled bathroom. Another bedroom offers the convenience of its own three-quarter bath. The spacious dining room could easily be reimagined as a fourth bedroom, home office, den, or additional living space to suit your needs. A large basement provides an abundance of storage and workspace and could easily accommodate a workshop, hobby area, or other creative uses. Outside, a newer concrete driveway leads to a substantial 30' x 30' outbuilding, of

Experience lakeside living at its best in this beautifully maintained stand alone condo set directly on Ashmere Lake. The main floor offers easy one level living with three bedrooms, two full baths, a welcoming great room with propane fireplace, a sunny breakfast nook, and a formal dining area. Step from the primary bedroom or great room onto the rear deck or relax in the three season porch overlooking Ashmere Lake. The finished lower level is perfect for guests or extended living, complete with a kitchenette, full bath, bedroom, large gathering space along with enclosed under-stair storage. Walk out access to the patio. Ashmere Landings amenities include a heated pool, Har Tru tennis court, pickle ball court, and lake access with kayak storage and dock. A rare blend of comfort, privacy

Welcome to your private retreat in the Crystal Pond community, set on just over 2 wooded acres. This 4-bedroom, 3.5-bath home blends comfort and natural beauty in a peaceful Berkshire setting. Cathedral ceilings, skylights, and expansive windows fill the home with natural light, highlighting rich wood plank flooring throughout. The main living area features a fireplace, while a separate den includes a wood stove insert for added warmth. One second-floor bedroom offers a private loft, and two additional bedrooms feature private balconies with wooded views. Enjoy a screened-in back porch and brand new front decks, ideal for relaxing or entertaining. A two-car garage with storage above provides space for vehicles, gear, and kayaks for nearby pond access

This four bedroom two bath log home with deeded rights to Ashmere lake has several updates including the furnace, garage and Generac generator. Property includes an extra lot for possible expansion or just privacy. First floor laundry for ease and convenience, as well as hook ups in the basement. The property includes lot 13 that the home is on and Lot 12 is a 75.03 X 215.41 extra lot

In town 2-bedroom ranch with strong potential! Features include public water/sewer, off street parking, and a fenced backyard. Ideal for contractors, investors, or buyers seeking a project. Home is not insurable/does not qualify for standard financing due to roof condition and is offered as is. A great opportunity to renovate and add value

Completely renovated contemporary home on almost 10 acres of marvelous land. The home sits back from the road, offering tranquility and privacy. The first floor features two bedrooms and an additional room with a wood-burning fireplace which can be used as a recreation room or a third bedroom. Downstairs you will also find a large laundry room with epoxy flooring, and a brand new full bathroom. The second floor offers an open concept and features a brand new kitchen with quartz countertops, a great room with a wood stove, a cozy dining area and a new full bathroom with a jetted tub. You will feel like you are at a spa! Relax and enjoy nature from your tub or step outside to the new deck that wraps around the home. The property has great quality flooring, from terracotta Mexican tile to walnut wood. Other improvements include new LP SmartSide siding, a new electrical service, roof, plumbing, windows and mini-splits throughout that provide both heat and A/C. A detached garage and a recen

Exceptional opportunity to enhance an already ideal waterfront home with the inclusion of the adjoining waterfront parcel, 26 Cove Lane. Offering added privacy, expanded shoreline enjoyment, and additional space, this extra lot creates exciting possibilities for a future owner. Whether envisioned for expansion of the existing home, additional outdoor living space or the potential for a separate structure, the parcel adds significant versatility and value on one the most desirable locations on Ashmere Lake. Expansive deck and private dock. Enjoy peaceful mornings and unforgettable sunsets on beautiful Ashmere Lake!

Welcome to your private retreat in the Crystal Pond community, set on just over 2 wooded acres. This 4-bedroom, 3.5-bath home blends comfort and natural beauty in a peaceful Berkshire setting. Cathedral ceilings, skylights, and expansive windows fill the home with natural light, highlighting rich wood plank flooring throughout. The main living area features a fireplace, while a separate den includes a wood stove insert for added warmth. One second-floor bedroom offers a private loft, and two additional bedrooms feature private balconies with wooded views. Enjoy a screened-in back porch and brand new front decks, ideal for relaxing or entertaining. A two-car garage with storage above provides space for vehicles, gear, and kayaks for nearby pond access

Impeccably maintained contemporary home set on four manicured acres bordering Massachusetts Fish and Game conservation lands and surrounded by approximately 4,500 acres of protected land in Hinsdale. Enjoy a private, serene setting just 1.6 miles from 287-acre Ashmere Lake. Inside, open entertaining spaces blend seamlessly with quiet retreats. The main level features a designer kitchen with granite countertops, Wolf range, and breakfast bar flowing into the dining area. A light-filled great room with gas fireplace offers year-round comfort, while a three-season screened porch and expansive decks invite outdoor dining. Three bedrooms include a first-floor primary suite with attached office or reading room. Additional highlights include 2.5 baths, laundry room, oversized two-car garage, and a massive basement with workbench and abundant storage. Just 30 minutes to Tanglewood, under 3 hours to Boston, and just over 3 hours to Manhattan

Have you been searching for an affordable retreat in the Berkshires? Nature lovers, hikers & outdoor enthusiasts, could this be the one you've been waiting for. Last house before entrance to one of Skyview Association's docks & water. Not waterfront but oh so close, check out the map. Nestled among trees this cottage offers a peaceful escape where mornings begin with birdsong & evenings end around the fire under the stars. The living room features large windows that bring the outdoors in, while the oversized bedroom provides plenty of sleeping space for family & guests. Structure supported on piers; some piers are leaning/settling. Two sheds for extra storage. Bring your vision, your tools, & your love of the outdoors to restore this cabin into the getaway it was meant to be. Skyline Association members have access to several boat launches & beach. EASY to show. Agents use ShowingTime

Completely renovated contemporary home on almost 10 acres of land. The home sits back from the road, offering tranquility and privacy. The 1st floor features 2 bedrooms and an additional room with a wood-burning fireplace which can be used as a recreation room or a 3rd bedroom. Downstairs you will also find a large laundry room with epoxy flooring, and full bathroom. The second floor offers an open concept and features a brand new kitchen with quartz countertops, a great room with a wood stove, a cozy dining area and a new full bathroom with a jetted tub. You will feel like you are at a spa! Relax and enjoy nature from your tub or step outside to the new deck that wraps around the home. The property has great quality flooring, from terracotta Mexican tile to walnut wood. Other improvements include new LP SmartSide siding, new electrical service, roof, plumbing, windows and mini-splits throughout that provide both heat and A/C. Setached garage and a recently paved driveway!

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

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 is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

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 is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

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

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

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 is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted