Chester, MA homes for sale & real estate

14 homes

Sort:

Recommended

73 Ingell Rd, Chester, MA 01011
73 Ingell Rd, Chester, MA 01011
73 Ingell Rd, Chester, MA 01011
ABOUT THIS HOME
Chester, MA Homes for Sale
A diamond in the rough! Located on a country road with expansive views. Rustic ranch-style farmhouse with a western flair. Notable improvements in the last 10 years roof/windows/skylight/furnace and updates to the electric. Generous open floor plan for the kitchen and living room with peaceful outside views to expansive skies. Second floor heated studio with approximately 385sf, potential to connect to the main house. Attached 8 stall barn with large loft for equestrian lovers or for many other purposes. Fenced in pasture in need of love. Enjoy views and night skies from this special property. Being sold "As Is". Title V passed.

$425,000

2 beds1 bath1,350 sq ft

73 Ingell Rd, Chester, MA 01011

8.07 acre lot • Garage • Car-dependent

12 Riverfront St, Chester, MA 01011
12 Riverfront St, Chester, MA 01011
12 Riverfront St, Chester, MA 01011
ABOUT THIS HOME
Chester, MA Homes for Sale
Charming riverfront home in historic Chester, close to all main attractions in Berkshire County and the college towns of Amherst and Northampton. The house has been lovingly maintained as a short-term rental since 2018, with excellent occupancy rates for visitors looking for a quiet getaway with a small town atmosphere while also central to all of Western Massachusetts. Single floor living, hardwood floors, updated kitchen and bath, back porch/mudroom and stunning deck with hot tub situated high above the serene Westfield River. This house is sold fully and tastefully furnished for immediate occupancy as your main home, vacation hideaway, or as a top-rated investment opportunity. Walking di

$339,900

2 beds1 bath1,450 sq ft

12 Riverfront St, Chester, MA 01011

0.34 acre lot • Garage • Car-dependent

613 Skyline Trl, Chester, MA 01011
613 Skyline Trl, Chester, MA 01011
613 Skyline Trl, Chester, MA 01011
ABOUT THIS HOME
Chester, MA Homes for Sale
Complete privacy awaits you in this charming Cape-style home! Perfect for easy entertaining, the home features a spacious three-season lanai with a wet bar, a covered patio, a large level yard, vibrant flowering gardens, and raspberry and blueberry bushes — plus a barn for added versatility. Inside, the cozy living room with a wood stove opens seamlessly to the kitchen, which is outfitted with stunning solid oak cabinetry, granite countertops, and beautiful stainless steel appliances. A large family room offers an additional office area with a full wall of built-in shelves — perfect for remote work or creative projects. The first-floor spa-like full bath includes a washer and dr

$489,500

3 beds2 baths2,012 sq ft

613 Skyline Trl, Chester, MA 01011

5.87 acre lot • 2 garage spots • Car-dependent

0 N Chester Rd, Chester, MA 01011
0 N Chester Rd, Chester, MA 01011
0 N Chester Rd, Chester, MA 01011
ABOUT THIS HOME
Chester, MA Homes for Sale
Here's your opportunity to own an amazing 5-acre property nestled in the heart of Chester, MA, in Hampden County. Located off Chester Rd, the parcel is considered landlocked, while a paper road provides recorded access, there is currently no vehicle access, and the land is being sold as-is. A plat map is available for review. Set on a gently sloping hillside overlooking a small river, the elevation offers potential for beautiful views of the surrounding valley. Zoned Residential with no HOA, the property’s undeveloped condition gives buyers the freedom to design their ideal getaway. Buyers should conduct their own due diligence to verify access, utility availability, zoning, and permi

$38,497

— beds— baths— sq ft

0 N Chester Rd, Chester, MA 01011

5 acre lot • Car-dependent

0 Round Hill Rd, Chester, MA 01011
0 Round Hill Rd, Chester, MA 01011
0 Round Hill Rd, Chester, MA 01011
ABOUT THIS HOME
Chester, MA Homes for Sale
A great get away with over three acres. There is a recent perk test, if you want to build on the land. This property comes with a newer camper. Walking distance to the hiking trails of the expansive Chester State Forest. The road does not have electric at this time, so off grid living is the way to go. 200 feet north of Smithy Road.

$34,000

— beds— baths— sq ft

0 Round Hill Rd, Chester, MA 01011

3.24 acre lot • Car-dependent

Property at 0 Skyline Trl, Chester, MA 01011

$150,000

— beds— baths— sq ft

0 Skyline Trl, Chester, MA 01011

Property at 0 Johnny Cake Hill Rd, Middlefield, MA 01243

$649,900

— beds— baths— sq ft

0 Johnny Cake Hill Rd, Middlefield, MA 01243

$649,900

— beds— baths— sq ft

0 Johnnycake Hill Rd, Middlefield, MA 01243

Property at 31 Skyline Trl, Chester, MA 01011

$299,800

— beds— baths— sq ft

31 Skyline Trl, Chester, MA 01011

Property at lot 13 Skyline, Chester, MA 01011

$47,000

— beds— baths— sq ft

lot 13 Skyline, Chester, MA 01011

Property at 0 Skyline Trail, Lot 24, Middlefield, MA 01243

$45,000

— beds— baths— sq ft

0 Skyline Trail, Lot 24, Middlefield, MA 01243

Property at lot 61 Skyline, Chester, MA 01011

$850,000

— beds— baths— sq ft

lot 61 Skyline, Chester, MA 01011

Property at lot 3 Skyline, Chester, MA 01011

$50,000

— beds— baths— sq ft

lot 3 Skyline, Chester, MA 01011

Property at 0 East River Rd Lot 13 Map 409, Chester, MA 01050

$75,000

— beds— baths— sq ft

0 East River Rd Lot 13 Map 409, Chester, MA 01050

Viewing page 1 of 1

End of results

Nearby homes that match your criteria

OPEN SAT, 11AM TO 1PM

138 Mystic Isle Way, Becket, MA 01223
138 Mystic Isle Way, Becket, MA 01223
138 Mystic Isle Way, Becket, MA 01223
ABOUT THIS HOME
Chester, MA Homes for Sale
Prepare to be wowed by this stunning lakefront home, which was built with meticulous craftsmanship by a Connecticut engineer and recently transformed by the current owners. Notable features include over 2,100 sq ft of flexible living space, 80'+ lake frontage, and every modern amenity. This turnkey home, which includes two separate living quarters, is perfect for multi-generational living or income potential. Inside you'll find an open concept showcasing lake views at every turn with vaulted ceilings, two high end kitchens, central AC, plus a full house generator, double EV charging station, propane heating, new dock, new roof, stone firepit, sunroom and screened in porch. All this and minu

$1,100,000

3 beds2 baths2,174 sq ft

138 Mystic Isle Way, Becket, MA 01223

0.34 acre lot • Car-dependent

134 Chester Rd, Blandford, MA 01008
134 Chester Rd, Blandford, MA 01008
134 Chester Rd, Blandford, MA 01008
ABOUT THIS HOME
Chester, MA Homes for Sale
Peaceful Ranch-Style Retreat on 6.81 Acres in Blandford! This well maintained home offers central air, central vac, and a whole house back up generator for year round comfort and convenience. The 2-car attached garage is heated and insulated, and there is a separate boat garage, wood shed and landscape shed for all your tools and toys. Relax on the beautiful mahogany deck overlooking beautiful landscape beds and a tranquil ponds and waterfalls, or cozy up inside by the wood stove. The home also features a security system for added peace of mind. A perfect blend of privacy, functionality, and nature-ideal for outdoor lovers, hobbyists, or anyone seeking quiet country living with easy access

$475,000

3 beds1.5 baths1,454 sq ft

134 Chester Rd, Blandford, MA 01008

6.81 acre lot • 4 garage spots • Car-dependent

269 River Rd, Worthington, MA 01098
269 River Rd, Worthington, MA 01098
269 River Rd, Worthington, MA 01098
ABOUT THIS HOME
Chester, MA Homes for Sale
Wonderful Country Cottage. This interesting contemporary home offers peace, quite, seclusion, to enjoy the beautiful surroundings offered by over 15 acres of land bounded on 2 sides by State Forest. Small brook and man made pond, flower and vegetable gardens, several small outbuildings including a rustic guest house. storage, chicken coop and more. House has a large sun space that serves for Plant Starting, passive solar and could easily become your family room. Living Dining area with vaulted ceiling and stone fireplace. Kitchen with unique counters from native wood, interesting Tile work, stain glass window all in great condition. Main floor is completed by a small bed room and unique bat

$409,000

2 beds1 bath1,152 sq ft

269 River Rd, Worthington, MA 01098

15.52 acre lot • Car-dependent

5 Lake View Rd, Peru, MA 01235
5 Lake View Rd, Peru, MA 01235
5 Lake View Rd, Peru, MA 01235
ABOUT THIS HOME
Chester, MA Homes for Sale
Nestled in the peaceful woods of Peru, MA, this two-bedroom cottage offers a serene escape just steps from Garnet Lake. Enjoy morning coffee on the enclosed porch, surrounded by birdsong and towering trees. While the property currently has no water or septic, it's a perfect canvas for your off-grid dreams or seasonal retreat. Whether you're kayaking, hiking or simply unwinding in nature, this location delivers tanquility in spades.

$134,600

2 beds1.5 baths640 sq ft

5 Lake View Rd, Peru, MA 01235

9,583 sq ft lot • Car-dependent

40 Dragon Way, Becket, MA 01223
40 Dragon Way, Becket, MA 01223
40 Dragon Way, Becket, MA 01223
ABOUT THIS HOME
Chester, MA Homes for Sale
This property offers a fantastic location and several desirable features. Just steps away, you'll find the * Sherwood Shoppe * , perfect for home cooking, or grabbing quick essentials. The Sherwood Forest area boasts several lakes with beaches for swimming, fishing, and non-motorized boating. Residents of Becket have rights to Center Lake and its beach. The home itself is clean and neat, offering two bedrooms with wood laminate floors throughout, as well as a full basement. It is equipped with oil heat and electric hot water. A small deck at the rear is ideal for grilling, while a large front deck has ample space for outdoor dining or lounging. The location is truly perfect, just 5 minutes

$199,000

2 beds1 bath651 sq ft

40 Dragon Way, Becket, MA 01223

9,600 sq ft lot • Car-dependent

527 Old Post Rd, Worthington, MA 01098
527 Old Post Rd, Worthington, MA 01098
527 Old Post Rd, Worthington, MA 01098
ABOUT THIS HOME
Chester, MA Homes for Sale
This is a wonderful Mini Farm with 5+ acres of fenced fields and pastures for rotating your livestock. House is a small ranch in great shape with Living Room, Dining area, galley Kitchen, with a 3 season porch in back. 3 bed rooms 2 of which are set as work spaces and a full bath round out the main floor. Basement offers finished area for guest use, work space and all utilities. Updated windows doors, utilities, and much more. Great Barn with loft that can hold up to 300 bales if hay plus a small walk in shed to get out of the sun and rain. Garage with chicken coop attached, nice outdoor patio and room for all your equipment and toys. Ready to go just bring your horses. alpacas, goats, shee

$439,000

3 beds1 bath960 sq ft

527 Old Post Rd, Worthington, MA 01098

10.77 acre lot • 2 garage spots • Car-dependent

Property at 137 Sherwood Dr, Becket, MA 01223, 1 bed, 1 bath

$169,000

1 bed1 bath528 sq ft

137 Sherwood Dr, Becket, MA 01223

Property at 343 Huntington Rd, Worthington, MA 01098, 5 beds, 4.5 baths

$1,250,000

5 beds4.5 baths5,355 sq ft

343 Huntington Rd, Worthington, MA 01098

Property at 345 Big Bass Ln, Becket, MA 01223, 3 beds, 2 baths

$499,900

3 beds2 baths1,800 sq ft

345 Big Bass Ln, Becket, MA 01223

Property at 359 Jacobs Ladder Rd, Becket, MA 01223, 3 beds, 2 baths

$649,500

3 beds2 baths2,820 sq ft

359 Jacobs Ladder Rd, Becket, MA 01223

Property at 274 Goss Hill Rd, Chester, MA 01050, 3 beds, 3 baths

$519,900

3 beds3 baths2,644 sq ft

274 Goss Hill Rd, Chester, MA 01050

Property at 841 Moberg Rd, Becket, MA 01223, 3 beds, 2 baths

$425,000

3 beds2 baths1,449 sq ft

841 Moberg Rd, Becket, MA 01223

Property at 6 Brookside Glen --, Huntington, MA 01050, 3 beds, 2 baths

$489,000

3 beds2 baths2,117 sq ft

6 Brookside Glen --, Huntington, MA 01050

Property at 233 Algerie Rd, Becket, MA 01223, 3 beds, 4 baths

$690,000

3 beds4 baths2,786 sq ft

233 Algerie Rd, Becket, MA 01223

Property at 0 Hamilton Rd, Becket, MA 01223

$23,900

— beds— baths— sq ft

0 Hamilton Rd, Becket, MA 01223

Property at 00 Fritz Rd, Worthington, MA 01098

$55,000

— beds— baths— sq ft

00 Fritz Rd, Worthington, MA 01098

Property at 0 Middlefield Rd, Washington, MA 01223

$65,000

— beds— baths— sq ft

0 Middlefield Rd, Washington, MA 01223

Property at 218-179-1- Bonny Rigg Hill Rd Rd, Becket, MA 01223

$85,000

— beds— baths— sq ft

218-179-1- Bonny Rigg Hill Rd Rd, Becket, MA 01223

Property at 195 Goss Hill Rd, Huntington, MA 01050

$115,000

— beds— baths— sq ft

195 Goss Hill Rd, Huntington, MA 01050

Property at 8 William Holmes Rd, Becket, MA 01223

$15,999

— beds— baths— sq ft

8 William Holmes Rd, Becket, MA 01223

Average home prices near Chester, MA

Cities

Chicopee homes for sale
$309,900
Lee homes for sale
$524,000
Blandford homes for sale
Pittsfield homes for sale
$352,000
West Springfield Town homes for sale
$380,000
Northampton homes for sale
$599,000
Hatfield homes for sale
$625,000
Westfield homes for sale
$380,000
Huntington homes for sale
$519,900
Easthampton Town homes for sale
$459,900
Holyoke homes for sale
$303,000

Zip Codes

01050 homes for sale
$439,500
01011 homes for sale
$425,000

Chester, MA real estate trends

$1.14M

Sale price

+86.4%
since last year

$338

Sale $/sq ft

+15.8%
since last year

Over list price

0.2%

Days on market

Down payment

—

Total homes sold

See more Chester, MA market insights

More to explore in Chester, MA

Featured
Price

How to buy a house in Chester, MA

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Massachusetts

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Subsidiaries

Countries

United States

Canada

Updated January 2023: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, TITLE FORWARD, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

Rocket Mortgage is an affiliated business of Redfin. All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York. For additional information on Rocket Mortgage or to receive lending services in the State of New York, please visit RocketMortgage.com.

Rocket Mortgage, LLC, Rocket Homes Real Estate LLC, Rocket Card, LLC, RockLoans Marketplace LLC (doing business as Rocket Loans), and Rocket Money, Inc., are separate operating subsidiaries of Rocket Limited Partnership. Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company is a separate legal entity operated and managed through its own management and governance structure. Rocket Limited Partnership is an indirect, wholly owned subsidiary of Rocket Companies, Inc. (NYSE: RKT).

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.