Chester, MA homes for sale & real estate

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OPEN OCT 12, 11AM TO 1PM

ABOUT THIS HOME
Chester, MA Homes for Sale
Very well-maintained home on dead end street within walking distance to store, 2 restaurants and library. Walk out onto the back deck to a nice size yard with the West Branch of the Westfield River in your back yard, to come home and stick your toes in and relax after a long day. 6 rooms 3 bedrooms and 1.25 baths, 1 car attached garage and a cute front porch. Title V failed, perc test done, design being generated and new septic system to be installed. Same owner for 50 years and it is time to move on. Move right in and enjoy the holidays. Open House Monday, October 12 from 11-1. Don't miss this sweet home.

$290,000

3 beds1.5 baths1,384 sq ft

27 Maple Ave, Chester, MA 01011

Nice size yard • New septic system • Back deck

ABOUT THIS HOME
Chester, MA Homes for Sale
First Showings start Sunday 10/4 at the Open House, 11am-12:30pm on this great starter home. If you have been looking for an affordable opportunity to buy a home, then this is it. The home has an open layout with a large living room, dining room and a full bath all on the first level. There is also a sizable country kitchen that leads to a deck with a pleasant view of the hills of Chester. There is a laundry off the kitchen as well. The second floor has another bedroom and an open area that is presently used as a guest/bed loft. Off the back deck is a yard with enough room for the kids or entertaining. There is also a barn shed on the property for workshop or storage. This home is the perfe

$189,000

2 beds1 bath1,160 sq ft

1 William St, Chester, MA 01011

Laundry off kitchen • Open layout • Large living room

ABOUT THIS HOME
Chester, MA Homes for Sale
Escape to the scenic hills of Chester with this unique 5.2-acre property offering the opportunity to create your year-round country home. Two major infrastructure investments are already in place with the well and three bedroom septic system. Giving you the head start on your new home. The existing 560-square-foot cottage provides a comfortable retreat while you plan and develop your vision for the property. Surrounded by wooded acreage, the setting offers privacy, natural beauty, and plenty of room to enjoy the outdoors. In the meantime, the existing cottage makes an excellent weekend getaway, hunting lodge, or recreational retreat. Built in 2011 with a metal roof, wood exterior, the cotta

$129,900

Studio1 bath560 sq ft

93 Crane Rd, Chester, MA 01011

5.2-acre property • Metal roof • Wooded acreage

ABOUT THIS HOME
Chester, MA Homes for Sale
Welcome home to your little slice of a rural countryside community. This property is situated on the west branch of the Westfield River in a quiet but convenient location. Enjoy your coffee on the porch and get lost in the sounds of nature. Inside you will find an open floor plan, a newer primary first floor bedroom, and three rooms upstairs with closets. This home is a hidden gem with tons of potential. Book your showing and bring your vision. Water heater purchased in 2021. Roof on addition was put on this year APO. Roof on main part of house is about 12 years old. 500 gal propane tank is owned. Buyer to do due diligence. Property appraised for 239k.

$215,000

2 beds1 bath1,652 sq ft

23 Maple St, Chester, MA 01011

0.44 acre lot • 2 parking spots • Built 1870

VIDEO TOUR

ABOUT THIS HOME
Chester, MA Homes for Sale
Set on approximately 62 acres spanning both sides of Cone Road, Middle Branch Overlook Estate is a private country retreat with sweeping southeast-facing views across the Middle Branch of the Westfield River valley. Comprised of three abutting parcels and bordered by protected land to the north and south, the property features open fields, woodland, a year-round brook, ponds, fruit trees, gardens, and an extensive trail network. The three-bedroom timber-frame residence is positioned on a high point overlooking a gently sloping hayfield. Built with native wood and subsequently expanded, the home features warm pine interiors, open kitchen, dining and living areas, a first-floor primary suite

$1,550,000

3 beds3 baths2,613 sq ft

69 Cone Rd, Middlefield, MA 01243

Year round brook • Fruit trees • Private covered deck

Property at 254 Route 20, Chester, MA 01011, 3 beds, 1.5 baths

$234,900

3 beds1.5 baths1,968 sq ft

254 Route 20, Chester, MA 01011

Property at 1 Crane Rd, Chester, MA 01011, 4 beds, 2 baths

$150,000

4 beds2 baths2,151 sq ft

1 Crane Rd, Chester, MA 01011

Property at 166 Route 20, Chester, MA 01011, 2 beds, 1.5 baths

$100,000

2 beds1.5 baths1,328 sq ft

166 Route 20, Chester, MA 01011

Property at 143 River Rd, Huntington, MA 01050, 3 beds, 3 baths

$389,900

3 beds3 baths1,403 sq ft

143 River Rd, Huntington, MA 01050

Property at 56 Middlefield Rd, Chester, MA 01011, 5 beds, 3 baths

$365,000

5 beds3 baths2,832 sq ft

56 Middlefield Rd, Chester, MA 01011

Property at 0 Town Hill Rd, Middlefield, MA 01243

$77,000

Land4.79 acres (lot)

0 Town Hill Rd, Middlefield, MA 01243

Property at 0 Mica Mill Rd, Chester, MA 01011

$129,000

Land28.00 acres (lot)

0 Mica Mill Rd, Chester, MA 01011

Property at Lot 13 W Hill Rd, Middlefield, MA 01243

$49,997

Land5.00 acres (lot)

Lot 13 W Hill Rd, Middlefield, MA 01243

$40,000

Land10.00 acres (lot)

50 Smith, Chester, MA 01011

Property at 95 Lynes Rd, Chester, MA 01011

$40,000

Land3.54 acres (lot)

95 Lynes Rd, Chester, MA 01011

Property at 91 Lynes Rd, Chester, MA 01011

$50,000

Land3.47 acres (lot)

91 Lynes Rd, Chester, MA 01011

Property at lot 3 Holcomb Rd, Chester, MA 01011

$60,000

Land2.12 acres (lot)

lot 3 Holcomb Rd, Chester, MA 01011

Property at lot1 Holcomb Rd, Chester, MA 01011

$45,000

Land2.03 acres (lot)

lot1 Holcomb Rd, Chester, MA 01011

Property at lot 2 Holcomb Rd, Chester, MA 01011

$45,000

Land2.06 acres (lot)

lot 2 Holcomb Rd, Chester, MA 01011

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

$649,900

Land155.00 acres (lot)

0 Johnny Cake Hill Rd, Middlefield, MA 01243

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Nearby homes that match your criteria

3D WALKTHROUGH

ABOUT THIS HOME
Chester, MA Homes for Sale
Set on approximately 30 acres in Worthington, this private 3-bedroom home offers a rare combination of comfortable living space, privacy, and room to enjoy the outdoors. Built in 1994, the 2,044-square-foot residence has been lovingly maintained by its original owners and features three bedrooms, one full bath, and one half bath. Walking in the front door you are greeted with the extra wide stair case and entry space. As you enter the main living space the open kitchen is on one side and the open living room on the other. The large south facing windows allow the sun to shine throughout. Enjoy your morning in the sunk sitting area with the warming sun. Or connect with nature in the three sea

$565,000

3 beds1.5 baths2,044 sq ft

21 Guard, Worthington, MA 01098

Three season porch • Open kitchen • Claw foot tub

FLOOR PLAN

ABOUT THIS HOME
Chester, MA Homes for Sale
Come see this cheerful, modernized ranch, renovated with the utmost care by its architect owner over a ten year span. Deeded beach & lake access within walking distance. Plenty of room for all with two bedrooms on the main level, a recently finished family room off the kitchen & dining room areas plus a second living room. New slate & gleaming hardwood flooring- real! - throughout the main level. The completely renovated main bathroom features wood wainscotting, tile floors & jet tub. The walkout lower level opens onto the back yard with 2 storage sheds & fire pit. The large 27'x17' game room, with a wall of windows facing the back yard, could be used for mult

$345,000

2 beds1.5 baths1,620 sq ft

31 Old Carriage Rd, Becket, MA 01223

Deeded beach access • Walkout lower level • Finished family room

ABOUT THIS HOME
Chester, MA Homes for Sale
Berkshire County Lakefront cottage, fully furnished and just 30 minutes to Tanglewood!Near Lee and Lenox, this Berkshires waterfront cottage offers two bedrooms and a full bath on the main level, plus a bonus room in the lower-level walkout. An open floor plan--kitchen, dining, and living--opens to a screened-in porch with western views over Little Robin Lake. Enjoy the quiet of this no-motor lake: kayak, swim off your dock, or fish until sunset. Evening dinners or a glass of wine belong on the expansive lower stone patio. A gentle slope leads to lake access and an expansive shoreline--ideal for a fire pit and s'mores--plus an attached garage for winter storage of boats and water gear. Hike

$495,000

2 beds1 bath876 sq ft

126 Alan A Dale Dr, Becket, MA 01223

Screened-in porch • No-motor lake • Lakefront cottage

ABOUT THIS HOME
Chester, MA Homes for Sale
47 Acre woodland sanctuary with home and guest house in Worthington MA. Home is at the end of a quarter mile driveway off a scenic road. 18th century style Cape, built in 1990, Central chimney, hand split cedar shake, gambrel roof, red cedar clapboards. 2 bedrooms, 1 full and 1 half bath; 3 Rumford fireplaces. Shiplap wide board pine paneling, batten doors, wide pine floors, hand troweled plaster walls and ceilings, antique hardware; Kitchen with stone countertop and custom-made cabinets. Views toward valley and distant hills. The special property also has a detached guest house which is a 1783 historic Worthington cape, reassembled as guest quarters with study, bedroom, foyer, and full bat

$814,000

3 beds1.5 baths2,325 sq ft

130 Prentice Rd, Worthington, MA 01098

Red cedar clapboards • Gambrel roof • Central chimney

ABOUT THIS HOME
Chester, MA Homes for Sale
Welcome to 135 South Road in beautiful Peru! This charming 3-bedroom, 2-full-bath Cape-style home, built in 2004, offers comfort, privacy, and country living on just over 3 acres of private land. The main level offers 2 bedrooms, full bath and living space, while the oversized 2-car garage provides plenty of room for vehicles, storage, hobbies, or outdoor equipment. The spacious second floor is dedicated to a beautiful primary en-suite, featuring a luxurious jet tub and a huge walk-in closet. Enjoy the peace and privacy of your own covered wrap around porch that adds to the charm of this beautiful home.

$429,900

3 beds2 baths1,560 sq ft

135 South Rd, Peru, MA 01235

Private land • Primary en-suite • Jet tub

VIDEO TOUR

ABOUT THIS HOME
Chester, MA Homes for Sale
HOMESTEADERS and HORESELOVERS here is your Dream Home! Comfortable Country Living on almost 5 acres, less than 10 miles from city amenities. A mountain top Modern RANCH: kitchen w/ Granite counters & Island, a Wood Stove in the dining area w/ Bay Wndow, Skylights and Beamed Ceiling in the living room, and sunny Loft with endless uses. The rear Addition: an L-shaped Family Room with Sliders stepping out to the backyard, Patio, & Deck, has a wonderful unexpected BONUS~ an Indoor HotTub! There's a basement with a "game room" complete with a drink refrigerator then a spiral staircase leading up to the LR. This thoughtful, unique floor plan easily lends itself to private rel

$544,000

3 beds2 baths2,980 sq ft

84 Chester Rd, Blandford, MA 01008

3 bay garage • Indoor hottub • Wood stove

Property at 172 Skyline Trl, Middlefield, MA 01243, 4 beds, 3 baths

$475,000

4 beds3 baths3,104 sq ft

172 Skyline Trl, Middlefield, MA 01243

Property at 347 Kinne Brook Rd, Worthington, MA 01098, 3 beds, 2 baths

$479,000

3 beds2 baths2,055 sq ft

347 Kinne Brook Rd, Worthington, MA 01098

Property at 3 Pleasant St, Huntington, MA 01050, 4 beds, 1 bath

$305,000

4 beds1 bath1,600 sq ft

3 Pleasant St, Huntington, MA 01050

Property at 859 Moberg Rd, Becket, MA 01223, 3 beds, 2 baths

$399,500

3 beds2 baths1,460 sq ft

859 Moberg Rd, Becket, MA 01223

Property at 233 Gentian Holw, Becket, MA 01223, 3 beds, 3 baths

$339,000

3 beds3 baths1,846 sq ft

233 Gentian Holw, Becket, MA 01223

Property at 2-R Old Chester Rd, Blandford, MA 01008, 4 beds, 2.5 baths

$495,000

4 beds2.5 baths2,920 sq ft

2-R Old Chester Rd, Blandford, MA 01008

Property at 229 Hamilton Rd, Becket, MA 01223, 3 beds, 2.5 baths

$575,000

3 beds2.5 baths2,079 sq ft

229 Hamilton Rd, Becket, MA 01223

Property at 10 Brookside Rd, Peru, MA 01235, 1 bed

$84,900

Land2.45 acres (lot)

10 Brookside Rd, Peru, MA 01235

Property at 0 Hayscent Dr, Becket, MA 01223

$24,500

Land2.05 acres (lot)

0 Hayscent Dr, Becket, MA 01223

$32,500

Land2.61 acres (lot)

Seneca Dr, Becket, MA 01223

Property at 0 Sir Edwards Way, Becket, MA 01223

$38,000

Land1.95 acres (lot)

0 Sir Edwards Way, Becket, MA 01223

Property at 0 William Holmes Rd, Becket, MA 01223

$84,000

Land12.89 acres (lot)

0 William Holmes Rd, Becket, MA 01223

Property at lot A/B Goss Hl, Montgomery, MA 01050

$400,000

Land82.13 acres (lot)

lot A/B Goss Hl, Montgomery, MA 01050

Property at 0 Bonny Rigg Hill Rd, Becket, MA 01223

$25,000

Land2.65 acres (lot)

0 Bonny Rigg Hill Rd, Becket, MA 01223

Average home prices near Chester, MA

Cities

Chicopee homes for sale
$360,000
Lee homes for sale
$625,000
Blandford homes for sale
$363,950
Pittsfield homes for sale
$310,000
West Springfield Town homes for sale
$393,700
Northampton homes for sale
$635,000
Hatfield homes for sale
$592,500
Westfield homes for sale
$434,950
Huntington homes for sale
$302,450
Easthampton Town homes for sale
$485,000
Russell homes for sale
$469,000
Holyoke homes for sale
$334,450

Zip Codes

Chester, MA real estate trends

$204K

Sale price

-32.0%
since last year

$237

Sale $/sq ft

+104.3%
since last year

Over list price

2.4%

Days on market

Down payment

—

Total homes sold

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