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

What an opportunity this one is! With 12 rooms and 7 bedrooms, this fixer-upper can become your hilltown dream-come-true! Gorgeous, private yard, with a two car garage and matching red barn tucked way in the back, this dreamy backyard is part of over one acre of peacefulness. Inside, the unique, flowing floor plan makes the potential of this house immense! Assessed at $352,500 in fair condition, just imagine what it'll be worth once you make it pristine! Three porches, farmhouse Dutch split entry door, 3 fireplaces, first floor bedroom, hardwood floors, and a huge kitchen with annexes and bonus features. Pull-down stairs to the attic offer even more space, at the very least for storage. Great opportunity for co-ownership, to share this big house. CASH only, dependent upon lender short sale approval. All showings deferred until 7/15/26 12-2:00 Open House

Nestled deep off a quiet country road and completely hidden from view down a long dirt driveway, this 1980s contemporary home offers a rare retreat for buyers seeking absolute privacy, mature natural surroundings, and a serious project with massive upside.Generous natural light, and a versatile layout, the home is a canvas ready for a full reimagining. Situated on over 6 sprawling acres, the setting is peaceful, secluded, and quintessential Western Mass.This property is being sold as-is and has significant deferred maintenance. A full roof replacement is needed immediately, along with extensive interior updates throughout. Due to the condition of the roof and structure, traditional financing (FHA, VA, or standard conventional) will likely not be an option. Personal effects will be left

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

The Possibilities are endless! Family Compound & Retreat! Hotel, Wedding Venue, Campgrounds, Cross Country Skiing Trails or Family Compound, bring your imagination and bring Buck Steep Manor back to Life! Five Buildings and many Cabins amid this 350-acre Estate. The Manor House 25 rooms the Lodge 19 rooms the Dutch Colonial Barn 5 rooms the Cottage 10 rooms The Antique Carriage Barn Hall 99pl capacity, and the Post and Beam Utility Barn two levels. Photos are from the past when it was running as a venue. It has frontage on Washington Mt Rd, Frost Rd and Lovers Lane Rd. Come view this unique property you won't be disappointed. All Information to be confirmed by Buyer. See Also MLS Listing 73240- in Commercial

Escape to your own mountaintop sanctuary where privacy, breathtaking views, and endless possibilities come together. Homestead in the Sky is a rare opportunity to own two parcels totaling 56 acres of pristine mountain land. Whether you dream of creating a family compound, establishing a self-sufficient homestead, developing an exceptional equestrian estate, or simply enjoying a peaceful mountain retreat, this remarkable property offers the space and freedom to make it your own. Built just 10 years ago, the thoughtfully designed home captures spectacular views from nearly every room. The custom kitchen is both beautiful and functional, featuring granite countertops, handcrafted tile work, a gas range, and double ovens ready for everyday living or entertaining

The Possibilities are endless! Family Compound & Retreat! Hotel, Wedding Venue, Campgrounds, Cross Country Skiing Trails or Family Compound, bring your imagination and bring Buck Steep Manor back to Life! Five Buildings and many Cabins amid this 350-acre Estate. The Manor House 25 rooms the Lodge 19 rooms the Dutch Colonial Barn 5 rooms the Cottage 10 rooms The Antique Carriage Barn Hall 99pl capacity, and the Post and Beam Utility Barn two levels. Photos are from the past when it was running as a venue. It has frontage on Washington Mt Rd, Frost Rd and Lovers Lane Rd. Come view this unique property you won't be disappointed. All Information to be confirmed by Buyer. See Also MLS Listing 73240- in Commercial

Discover a charming single-family paradise at 17 Hemlock Ln, Hinsdale, MA. Located in the highly desired Ashmere Heights Association with 287 acres of lake access! This home offers a unique opportunity for tranquil living in a picturesque setting. With two bedrooms, this home provides comfortable and private spaces for rest and rejuvenation. A single full bathroom serves the home, offering practical amenities for daily routines. Situated on a generous 10,890 square foot lot, this property offers ample outdoor space for leisure and potential expansion. Imagine the possibilities for creating your ideal outdoor retreat, from vibrant gardens to serene relaxation areas. The loft area is great for extra sleeping areas or storage. This inviting property presents a compelling opportunity to embrace a peaceful lifestyle in Hinsdale. Just a short walk from the associations private beach and non motorized watercraft storage area. Come see what the Berkshires have to offer!

Escape to your own mountaintop retreat at Homestead in the Sky. This rare offering includes two parcels totaling 56 private acres with breathtaking views, perfect for a family compound, homestead, horse property, or peaceful mountain getaway. The 10-year-young home captures stunning views from nearly every room. The custom kitchen features granite countertops, handcrafted tile, gas range, double ovens, and opens to a sun-filled living room with soaring ceilings, a wall of windows, and slider to deck overlooking Goose Pond, Mount Greylock, and the Berkshires. The primary suite offers a custom bath and walk-in closet. Outside, enjoy a greenhouse with lower-level goat barn, raised gardens, open pasture potential, miles of trails for horses, hiking or ATVs, plus a heated 28'x48' workshop with 14' ceilings. A truly exceptional mountain estate with endless possibilities

Vacation all year round! This turnkey lakefront house offers modern comfort and a stunning view of Ashmere Lake. Tucked on the eastern cove side of the lake, it provides a more sheltered stretch of waterfront. The main level features two bedrooms with oak hardwood floors and individual heat pumps for customizable comfort. The kitchen is finished with granite countertops, soft close cabinetry, and a practical open concept layout. The 2nd floor offers additional living space for a bedroom or quiet lounging, with a lovely front facing view of the lake. Mechanical updates include a new hot water heater, electric service panel, heating panels located in both the full bathroom and the basement, as well as heat pumps in the main living area, the 2nd floor and in the bedrooms. A deck off the main level overlooks a sweet'daisy flower yard' which supports pollinators. Dip your feet into the lake off of your own private dock!

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

Come enjoy the peace and quiet in this beautifully redone two-family property! This home has been completely updated from top to bottom, including New Roof and Siding, new walls, floors, and kitchen. Brand new fence for added privacy, a fully renovated basement with fresh concrete flooring, new water heaters, washer and dryer hookups on both floors, in addition, an upgraded electrical system. Whether you're looking for a comfortable home or a great investment opportunity, this property is move-in ready and built to last

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 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 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 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