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Chester, Massachusetts: Country Homes, Houses, and Rural Real Estate

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$525,000 42 acres 3 Beds | 4 Baths | 1856 sqft
72 Round Hill Rd, Chester, MA 01011 - Hampden County

42 acres Chester, MA

Dreaming of cutting the cord? Experience the freedom of living off grid with this homesteading opportunity nestled in the hills of Chester, MA. Property located on 42 acres with fruit trees, grapes, diverse timber forest, barn and small guest cabin in the woods. Hiking, cross country skiing, and horse trails in the nearby state forest. This property would also make a wonderful second residence.
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$449,000 4.66 acres 3 Beds | 3 Baths | 2907 sqft
101 Ingell Road, Chester, MA 01011 - Hampden County

4.66 acres Chester, MA

ONLY 30 MINUTES TO THE BERKSHIRES W/O THE BERKSHIRE PRICE! Also only 30 minutes to Lee, Tanglewood, and Northampton! Designed with an artistic flair, this exquisite country property has numerous outstanding features. The entryway opens to the large cathedral ceiling living room featuring a Woodstock soapstone gas stove. Kitchen created by Crown Point of Claremont, NH with custom cabinets, granite counters and stainless appliances. Additional 1st floor rooms include a dining room, sunroom, den, laundry room, master bedroom and bath, plus another full bath. The upstairs has a second master bedroom with sitting room, full bath, 3rd bedroom, alcove off the stairs, and a passage way to more storage. The 4.66 acres are artfully landscaped with al
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$389,900 2 acres 5 Beds | 3 Baths | 2676 sqft
282 Skyline Trl, Chester, MA 01011 - Hampden County

2 acres Chester, MA

Pride of ownership is evident in this 5 bedroom, 2.5 bathroom home. Over 2600 sq ft of naturally lit living space with a nice open floor plan this home features a gorgeous 4 season sun room, first floor master bedroom, beautiful wide plank wood flooring throughout, first floor laundry and plenty of storage space. Finished basement has a huge home office, separate room with a pool table and a workshop that would be a dream for any handy man. If that's not enough there is a three bay garage with additional storage above. This is not a drive by! Make your appointment today.
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$349,500 30 acres 3 Beds | 2 Baths | 1924 sqft
87 Crane Rd, Chester, MA 01011 - Hampden County

30 acres Chester, MA

Private country home on 30 acres of woods, fruit trees and pond. This 3 bedroom, 2 bath home has 2 woodstoves, a newly remodeled kitchen with custom cabinets, an attached 2 car garage with sunroom and lots of country charm. You will enjoy the beamed ceilings, hardwood floors, large living room and cozy bedrooms. There is a full walk-out basement, a storage shed and barn.
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$349,000 12.02 acres 3 Beds | 3 Baths | 1401 sqft
1 Birch Circle, Chester, MA 01011 - Hampden County

12.02 acres Chester, MA

The Bungalow Log Home floor plan features one floor with no basement or loft. The log home begins with a front porch. An entrance opens to a dining room attached to the kitchen on the right, and the great room with a fireplace on the left. The dining room is separated from the kitchen by an island counter encasing a stove. Toward the rear of the Bungalow Log Home floor plan is a long hallway. The first room to the left, moving clockwise down the hall, is a bathroom, a small closet, a bedroom with private bathroom, the master bedroom is at the end of the hall with a large walk-in closet and a master bath featuring two sinks, second bedroom, laundry room, and pantry. According to the Bungalow Log Home floor plan the laundry room also op
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$249,000 22.9 acres 3 Beds | 2 Baths | 1822 sqft
7 Soisalo, Chester, MA 01011 - Hampden County

22.9 acres Chester, MA

Custom build Chalet home based on log home design. Enjoy sitting on the deck enjoying nature at its best. Stone walls, fruit trees, wild blueberry bushes, fenced in garden area. Build as a weekend retreat and hunting cabin. Detached 3 bay garage with work area a 1 bay has front & rear garage door for drive thru ease. There is also a walk up loft area for added storage.
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$200,000 10.5 acres 3 Beds | 2 Baths | 2052 sqft
24 Bromley Rd, Chester, MA 01011 - Hampden County

10.5 acres Chester, MA

Unique contemporary, welcoming country setting on 10.5 acres. Lots of windows to let the natural sunlight in.Large rooms & some beautiful wood flooring you will find a sunroom with a wall of windows for watching nature as you relax with your cup of coffee or glass of wine.Lease Option with a 2 yr. min. lease, monthly rental fee of $1,600 required. Owners have never lived in the home.
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$189,000 3.4 acres 1 Bed | 2 Baths | 1344 sqft
517 Skyline Trl, Chester, MA 01011 - Hampden County

3.4 acres Chester, MA

Bring your paint brush, broom, and love for the country to this beautiful A-frame on Skyline Trail. This house needs some cleaning and painting but is structurally sound. All major systems are in working order. The roof was redone in 2008 with 30 year architectural shingles. There are two fire places that are set up for pellet stoves, wide pine floors in the living room and master bedroom. The kitchen has new ceramic tile. The partially finished basement has a room that was used as a second bedroom and a den/family room. This country A-frame comes with 3.4 acres of land, a fenced in gardening area, a small chicken coop, and an unheated garage/work space. Several stone walls can be found throughout this beautiful country property. T
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$182,500 2.5 acres 4 Beds | 2 Baths | 2236 sqft
289 ROUTE 20 --, Chester, MA 01011 - Hampden County

2.5 acres Chester, MA

Nicely kept 4 bedroom, 2.5 bath home on 2.5 acres in Chester Village. Large, bright kitchen with room for breakfast table & chairs. Dining room has built-in wood cabinets. Living room has fireplace. Rooms and ceilings recently repainted and 1st floor bath renovated. Two bedrooms on 1st floor with full bath - two more bedrooms on 2nd floor with full bath.