Homes for sale under $800k in Chester, MA

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ABOUT THIS HOME
Homes for sale under $800k in Chester, MA
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

Open floor plan • Notable improvements • Heated studio

ABOUT THIS HOME
Homes for sale under $800k in Chester, MA
This private Colonial home is set on 2.5 wooded acres at the end of a quiet dead-end road in Chester’s “Gem of the Valley. ” The property is fully equipped for equestrian and homesteading lifestyles, featuring a four-stall barn with walk-out access to a fenced paddock, along with two additional fenced pastures ideal for horses, goats, or other farm animals. Inside, the home has been freshly painted throughout, creating a crisp, move-in-ready feel. New carpet has been installed in the upstairs bedrooms, and the full bathroom has been updated with a new vanity, toilet, and flooring. The kitchen has been refreshed with appliances and lighting, offering a clean and functional

$374,900

3 beds1.5 baths1,792 sq ft

11 Campbell Rd, Chester, MA 01011

Fenced pastures • New gutters • Four stall barn

ABOUT THIS HOME
Homes for sale under $800k in Chester, MA
BOM due to Buyer Financing! Nestled on 4.5 Scenic Acres is where you'll find this private retreat, a beautifully updated ranch that's the perfect blend of modern comfort and country living. Thoughtfully updated boasting APO: A brand-new septic system, Architectural Roof in 2023, Newer Gas Boiler about 7-8 yrs old & More! An inviting open design w/ vaulted ceilings, recessed lighting, custom built-ins to discover an expansive living rm/family rm w/ a cozy wood stove flows seamlessly into the stylish kitchen w/ an abundance of chic white cabinets, stainless appliances, propane gas stove & charming dining area. There are 2 generous bedrms w/ wood flrs & roomy closets along w

$324,900

2 beds1 bath1,360 sq ft

689 Skyline Trl, Chester, MA 01011

Updated ranch • Newer gas boiler • Architectural roof

ABOUT THIS HOME
Homes for sale under $800k in Chester, MA
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.

$279,500

3 beds1.5 baths1,968 sq ft

254 Route 20, Chester, MA 01011

Vinyl windows • Natural light • Large kitchen

ABOUT THIS HOME
Homes for sale under $800k in Chester, MA
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 f

$235,000

2 beds1 bath1,076 sq ft

11 Taft Rd, Chester, MA 01011

Private deck • Blueberry bushes • Apple trees

Property at 187 Route 20, Chester, MA 01011, 2 beds, 1 bath

$234,900

2 beds1 bath860 sq ft

187 Route 20, Chester, MA 01011

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ABOUT THIS HOME
Homes for sale under $800k in Chester, MA
Available for the first time in decades, this exceptional property offers peace, privacy, and endless opportunities to explore nature! Set on 77 acres with brooks and meandering trails, it's a true retreat for those seeking both solitude and adventure. The home features a spacious, sunlit first-floor layout with an eat-in kitchen, dining room, living room with pellet stove, heated porch/bonus room, and half bath. A wide center staircase leads to the second floor, where you'll find three bedrooms, a full bath, and walk-up attic access. While ready for updates, the house offers a generous and functional floor plan—a blank canvas for your vision. Whether you're drawn to the historic dist

$699,900

4 beds1.5 baths2,948 sq ft

3258 Main St, Becket, MA 01223

Heated porch • Walk-up attic access • 77 acres

ABOUT THIS HOME
Homes for sale under $800k in Chester, MA
Nestled among rock outcrops and only steps from the shores of Indian Lake, this 6 bedroom, four-and-a-half bath home has been a welcoming place for generations. Designed with a contemporary, multi-level layout, its sun-filled spaces connect effortlessly to the outdoors, offering both gathering areas for friends and family as well as private nooks for quiet moments. Views shift with the seasons—from summer's sparkling water to autumn's vibrant foliage and the quiet beauty of winter snow. Well cared for and thoughtfully maintained, it now stands ready for its next chapter, inviting new owners to enjoy the same connection to nature, family, and place that has made it so special. Indian L

$699,900

6 beds4.5 baths3,144 sq ft

138 Seneca Dr, Becket, MA 01223

Sun-filled spaces • Gathering areas • Private nooks

ABOUT THIS HOME
Homes for sale under $800k in Chester, MA
Discover your dream retreat in this stunning log home on 37 acres, adjoining over 1,000 acres of state forest. Enjoy tranquility and breathtaking mountain views from the wrap-around deck while sipping your morning coffee. Relax in the wood-fired hot tub or outdoor sauna. Inside, the open floor plan features a chef's kitchen with granite countertops and a Viking stove, perfect for entertaining. The inviting living room boasts a cozy stone hearth fireplace. The first floor features two bedrooms and a main bathroom, while the second floor comprises an office, a private primary suite, and an en-suite bath. The walk-out basement offers space for hobbies or a gym. Embrace the charm of country liv

$699,000

3 beds2 baths2,284 sq ft

15 Stephanie Ln, Peru, MA 01235

37 acres • State forest • Outdoor sauna

ABOUT THIS HOME
Homes for sale under $800k in Chester, MA
Nestled on four private wooded acres, this handcrafted Lincoln log home offers a harmonious blend of timeless craftsmanship and contemporary living. Built by the original owners, the residence affectionately known as '' Log Mahal'' showcases meticulous attention to detail and a deep appreciation for natural materials. Step inside to a warm and inviting atmosphere, where exposed log beams and rich wood tones create a cozy ambiance. The open-concept living area is anchored by a stunning river rock stone fireplace, perfect for chilly evenings. Adjacent, a wood-burning stove adds both charm and additional warmth. Ascend the graceful winding staircase to the master suite - a private retreat feat

$699,000

3 beds2.5 baths2,820 sq ft

236 Surriner Rd, Becket, MA 01223

Winding staircase • Exposed log beams • Private wooded acres

ABOUT THIS HOME
Homes for sale under $800k in Chester, MA
Let's imagine extreme privacy for a moment, yet your loved ones are simply a three minute walk away or a quick drive; because each one has their own home! With connecting roads this home is 3 of 3. This home is the larger of the 3, Sitting at 2786 Sq. Ft. 3 Bedrooms, 3 Full Bathrooms, a spacious Great Room Perfect for entertaining. A completely finished lower level, currently being used as a game room. You will also find a full bath and a private Sauna. Just outside you will discover a fire pit with bench seating as well as a sauna. A parcel on Indian lakes is also an attractive feature that is available. This will give you access to the tennis court and the lake itself. A deck off of the G

$690,000

3 beds4 baths2,786 sq ft

233 Algerie Rd, Becket, MA 01223

Bench seating • Private sauna • Access to lake

ABOUT THIS HOME
Homes for sale under $800k in Chester, MA
Welcome to 106 Stoney Brook Road in the hills of Becket Massachusetts. This 3 bedroom 2 bath ranch offers an open concept living area including a spacious living room with pellet stove, eat in kitchen, and den just filled with natural light. The main floor offers a generously sized primary en suite complete with custom shower and walk-in closet. An additional 2 bedrooms and a full bath nicely round out the first floor. A partially finished basement adds to the charm and space within this beautiful home. On the exterior you will find a large deck off of the kitchen that overlooks the private and peaceful yard complete with fire pit that is perfect for anyone looking for a serene retreat that

$639,900

3 beds2 baths3,273 sq ft

106 Stoney Brook Rd, Becket, MA 01223

Large deck • Custom shower • Walk-in closet

Property at 289 Algerie Rd, Becket, MA 01223, 3 beds, 2.5 baths

$575,000

3 beds2.5 baths1,603 sq ft

289 Algerie Rd, Becket, MA 01223

Property at 337 Captain Whitney Rd, Becket, MA 01223, 5 beds, 3 baths

$575,000

5 beds3 baths2,252 sq ft

337 Captain Whitney Rd, Becket, MA 01223

Property at 674 Benton Hill Rd, Becket, MA 01223, 4 beds, 3 baths

$555,000

4 beds3 baths2,410 sq ft

674 Benton Hill Rd, Becket, MA 01223

Property at 173 King Richard Dr, Becket, MA 01223, 3 beds, 2 baths

$550,000

3 beds2 baths1,353 sq ft

173 King Richard Dr, Becket, MA 01223

Property at 554 Main St, Becket, MA 01223, 3 beds, 1.5 baths

$547,700

3 beds1.5 baths1,960 sq ft

554 Main St, Becket, MA 01223

Property at 283 Benton Hill Rd, Becket, MA 01223, 3 beds, 2 baths

$528,000

3 beds2 baths2,084 sq ft

283 Benton Hill Rd, Becket, MA 01223

Property at 18 Osceola Dr, Becket, MA 01223, 1 bed

$519,000

1 bed— baths720 sq ft

18 Osceola Dr, Becket, MA 01223

Property at 235 Algerie Rd, Becket, MA 01223, 3 beds, 2.5 baths

$500,000

3 beds2.5 baths1,440 sq ft

235 Algerie Rd, Becket, MA 01223

Property at 162 Ymca Rd, Becket, MA 01223, 3 beds, 2 baths

$499,000

3 beds2 baths1,600 sq ft

162 Ymca Rd, Becket, MA 01223

Property at 454 Seneca Dr, Becket, MA 01223, 3 beds, 3 baths

$499,000

3 beds3 baths1,536 sq ft

454 Seneca Dr, Becket, MA 01223

Property at 40 Ryan Rd, Washington, MA 01223, 3 beds, 2 baths

$495,000

3 beds2 baths2,300 sq ft

40 Ryan Rd, Washington, MA 01223

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

$494,900

3 beds2 baths1,800 sq ft

345 Big Bass Ln, Becket, MA 01223

Property at 500 E River Rd, Chester, MA 01011, 4 beds, 2 baths

$480,000

4 beds2 baths2,171 sq ft

500 E River Rd, Chester, MA 01011

Property at 1178 Bancroft Rd, Becket, MA 01223, 3 beds, 1.5 baths

$449,000

3 beds1.5 baths1,239 sq ft

1178 Bancroft Rd, Becket, MA 01223

Homes for sale under $800k in Chester

There are currently 6 homes for sale under $800k in Chester. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Chester stay on the market for 44 days. This map is refreshed with the newest listings in Chester every 15 minutes.

In the past month, 1 home has been sold in Chester. In addition to houses in Chester, there was also 1 condo, 0 townhouses, and 1 multi-family unit for sale in Chester last month. Find your dream home in Chester using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Chester are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Chester. Our Chester real estate stats and trends will give you more information about home buying and selling trends in Chester. If you're looking to sell your home in the Chester area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Chester with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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