Refine Search
Map
Sort by
$235,000
6 Beds ⋅ 2 Baths ⋅ 73503205 MLS
This is an outstanding opportunity to buy at well below market value. Both units are in move in condition however a septic system will need to be installed at the buyer's expense. Each unit is very expansive with three bedrooms in each unit. Over 4,000 square feet of living area. Many updates including newer furnaces. This is a very smart investment for a cash buyer or a rehab type loan to remedy the septic system. Chester is a desirable town located in the Berkshire foothills.

6 Maple St, Chester
$799,900
4 Beds ⋅ 3 Baths ⋅ 5075427 MLS
2026 means a brand-new home! Welcome to the Condor Farmhouse at Pipit Estates. This popular house style offers a wonderfully welcoming and functional floor plan with room for everyone. The Eat-in Kitchen is perfect with granite counters, stainless steel appliances, and a large pantry. An extra "Flex Room" can be utilized as a formal Dining Room, Playroom, or perhaps an Office. The Mudroom with an entrance from the garage will be a handy space for all. 3 spacious Bedrooms, a Primary Bedroom with attached Bathroom, and a large Laundry Room complete the second floor. The full basement is a walk-out with slider and daylight windows, perfect to finish in the future for additional living space. Pet friendly community and no age restrictions. Beautiful country setting with over 16 acres of open space. Take advantage of all the charming town of Chester has to offer including a top-rated school system! There are additional floor plans to choose from including Ranch homes for single floor living.

12 Robin Way Unit 5, Chester
$365,000
5 Beds ⋅ 4 Baths ⋅ 73461501 MLS
The price has improved! Don't miss out. Discover this charming and spacious two-family home nestled in the heart of Chester. Recently refreshed with new flooring throughout and thoughtful cosmetic updates, this well-maintained property is ready for its next owner. Each unit offers 3 comfortably sized bedrooms, 1.5 bathrooms, a large living room, dining area, kitchen, first-floor laundry, and a bonus room that can be used as an office, playroom, or additional storage. The property sits on a generous lot—close to 1 acre—with a large front yard and expansive backyard that accommodates parking for approximately 6 additional vehicles. Ideal for anyone seeking a tranquil setting with strong rental income potential or a reliable investment opportunity. A barn with a 2-car garage and upstairs loft adds even more versatility and is being sold as is. The home also includes a new septic system, offering added peace of mind.

56 Middlefield Rd, Chester
$1,500,000
4890134 MLS
Builders take notice! This is a rare opportunity you don’t want to miss out on with over 200 acres of undeveloped land in beautiful Chester. Sold together - there are 7 parcels; Tax Map 2 Lots 29, 30, 31, 31-1, 33, 38-1 and lot 39. Road frontage along Pomp Road and all land is in current use. Buyer to pay any fees when taking it out of current use status. Buyer to do their due diligence. Aerial photos coming soon. Also for sale is additional 483 acres in Derry, NH -see MLS 4890183 for more information.

Jack Rd, Chester
$264,900
3 Beds ⋅ 2 Baths ⋅ 73428417 MLS
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 that’s 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.

254 Route 20, Chester
$225,000
2 Beds ⋅ 1 Baths ⋅ 73416131 MLS
This cedar sided bungalow in a peaceful setting offers an open floor plan, 5.61 acres of land, a private deck overlooking the beautiful yard w/ blueberry bushes, apple & pear trees. Kitchen w/appliances to stay. Cozy DR. Large open LR w/cathedral ceilings. First floor laundry. Full bath w/tub & shower. Potential for a half bath off the empty bedroom (it was a half bath at one time) Abbott Brook runs along the back edge of the property. This would make a great vacation retreat or year-round home. Enjoy the recreational areas & activities all close by or take a short drive to the Berkshires or Northampton. This is an ideal location to be away from it all but not too far from major cities. New hot water tank, newer pressure tank for the well. Septic was new in 2009 & the roof was last redone in 2014. Electric baseboard heat & forced air wood furnace in the basement. Also wood stove hook up in the living room. Some cosmetic TLC needed, bring your imagination to make this home your own

11 Taft Road, Chester
$75,000
72690617 MLS
Private 18 acre lot! 200 feet of frontage & 3000 feet back w/winding trails & a brook. From the road there is a little clearing with ATV trails to the right & an old over grown skidder trail to the left as land has not been logged since 2007. The skidder trail rises up to the top of a ridge & there is a brook in the back left corner. The ATV trails wind gently leading up to the flatter portions w/possible views & home site location potential. There is electric on the street. One mile down the road are the Littleville Fairgrounds and Dayville. Trails criss cross over east river road in a few locations offering you the ability to explore beyond your property into many of the hilltowns' recreational destinations. This property would make a great recreational camp for hunting, fishing, hiking & more or it could be the site to build your dream home. Plot plans & old logging plan in photos. Lot 14 to the right is also for sale different owner, similar lot, possibility to purchase both.

East River Rd Lot 13 Map 409, Chester

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

board logoCopyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated .