35

Homes for Sale near Chester Elementary School

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  • /39

    $414,999

    • 5 Beds
    • 4 Baths
    • 2,832 Sq Ft

    56 Middlefield Rd, Chester, MA 01011

    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,

    Agent Photo

    Cynthia Gonzalez

    Executive Real Estate, Inc.

    (413) 966-0486

    56 Middlefield Rd, Chester, MA 01011
  • /30

    $575,000

    • 3 Beds
    • 2.5 Baths
    • 1,603 Sq Ft

    289 Algerie Rd, Becket, MA 01223

    This Contemporary Ranch offers easy living with interesting open common spaces and all three bedrooms and two and a half baths on the main level. The expansive kitchen with European styling, giving you the washer & dryer in this space for convenience, has wonderful storage, a generous center island that is open to the dining area that is open to the living room. Enjoy the amazing deck with the

    Agent Photo

    Cristian Sanchez

    COHEN & WHITE ASSOCIATES

    (413) 338-8629

    289 Algerie Rd, Becket, MA 01223
  • /12

    $649,900

    • Land
    • 155 Acres
    • $4,193 per Acre

    0 Johnny Cake Hill Rd Unit 246420, Middlefield, MA 01243

    This approximately 155-acre Berkshire nature preserve has enough frontage on Johnnycake Hill Road to accommodate four building lots. Nestled in the beautiful corner of the world where the Pioneer Valley meets the Berkshire Hills, the property is ideal for a myriad of outdoor uses including horseback riding and cross-country skiing. The land contains well over a mile of logging trails and old

    Doug Collins LAMACCHIA REALTY, INC

    0 Johnny Cake Hill Rd Unit 246420, Middlefield, MA 01243
  • /54

    $875,000

    • 3 Beds
    • 2.5 Baths
    • 2,700 Sq Ft

    55 Mallard Dr, Becket, MA 01223

    Discover the perfect blend of comfort and charm with this stunning contemporary situated on two acres. There is a full-house Generac generator for comfort and peace of mind and central air. The great room is washed with natural light from the wall of windows and has a beautiful gas fireplace to provide additional warmth on cold Winter days. There is a circular flow into the spacious dining room

    Cortney Dupont COHEN & WHITE ASSOCIATES

    55 Mallard Dr, Becket, MA 01223
  • /12

    $69,900

    • Land
    • 10.4 Acres
    • $6,721 per Acre

    Lot 8 Benton Hill Rd, Becket, MA 01223

    10+ acre lot with a recent passing perc test. and two brooks. A small brook crosses the property towards the rear as it heads towards Center Pond Brook. Town maintained road, no HOA, electric & fiber optic at the street. Abutting property also available.

    Kim Bergland RED HORSE REAL ESTATE, LLC

    Lot 8 Benton Hill Rd, Becket, MA 01223
  • /11

    $64,900

    • Land
    • 6.52 Acres
    • $9,954 per Acre

    LOT9 Benton Hill Rd, Becket, MA 01223

    6.5 acres with frontage on Center Pond Brook and newly perced. Rough driveway in with some overgrown cleared areas. Abutting properties on both sides available.

    Kim Bergland RED HORSE REAL ESTATE, LLC

    LOT9 Benton Hill Rd, Becket, MA 01223
  • /34

    $547,700

    • 3 Beds
    • 1.5 Baths
    • 1,960 Sq Ft

    554 Main St, Becket, MA 01223

    Experience a peaceful Berkshire fall from this inviting ranch-style home in the quiet hills of Becket. Surrounded by vibrant foliage and towering pines, this single-level retreat offers warmth, comfort, and nature at your doorstep. Enjoy scenic hikes and crisp fall days now, then gear up for winter fun with Otis Ridge, Bousquet Mountain, and Jiminy Peak just a short drive away. With a fully

    Audrey Matys BERKSHIRE LISTINGS

    554 Main St, Becket, MA 01223
  • /7

    $75,000

    • Land
    • 18.05 Acres
    • $4,155 per Acre

    0 E River Rd Lot 13 Map 409 Unit 72690617, Chester, MA 01050

    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

    Victoria Minella-Sena Berkshire Hathaway HomeServices Realty Professionals

    0 E River Rd Lot 13 Map 409 Unit 72690617, Chester, MA 01050
  • /23

    $225,000

    • 2 Beds
    • 1 Bath
    • 1,076 Sq Ft

    11 Taft Rd, Chester, MA 01011

    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

    Victoria Minella-Sena Berkshire Hathaway HomeServices Realty Professionals

    11 Taft Rd, Chester, MA 01011
  • /40

    $289,900

    • 3 Beds
    • 1.5 Baths
    • 966 Sq Ft

    70 Town Hill Rd, Middlefield, MA 01243

    Welcome to this beautifully updated 3-bedroom, 1.5-bath Cape set in a peaceful, private location. Thoughtfully renovated, the home features a brand-new kitchen with white shaker cabinets, stainless appliances, and abundant natural light, along with updated baths and the convenience of first-floor laundry. Enjoy year-round comfort with a new furnace and central air. A large two-car garage provides

    Alice Kempf Kempf-Vanderburgh Realty Consultants, Inc.

    70 Town Hill Rd, Middlefield, MA 01243
  • /7

    $139,000

    • Land
    • 0.32 Acre
    • $434,381 per Acre

    LOT112 Osceola Rd, Becket, MA 01223

    WATERFRONT LOT WITH FIFTY FEET ON THE LAKE. Unusual, undeveloped .32 acre lot on Center Pond with 50' of easterly facing shorefront. Being sold as is, raw land. Buyers to do their own due diligence.

    Kim Bergland RED HORSE REAL ESTATE, LLC

    LOT112 Osceola Rd, Becket, MA 01223
  • /22

    $49,500

    • 5 Beds
    • 1.5 Baths
    • 2,322 Sq Ft

    171 Prospect St, Chester, MA 01011

    Beautiful wood house with tons of space and character, needs some love to bring back to life. Nestled into the hills of Chester, it's just steps away from the Railway Museum and downtown. Foundation partially rebuild with newer windows and doors. Much work already done. Come bring it over the finish line and have yourself a beautiful historic house with amazing mountain and river views.

    Vadim Tulchinsky Witman Properties, Inc.

    171 Prospect St, Chester, MA 01011
  • /7

    $30,000

    • Land
    • 1.98 Acres
    • $15,151 per Acre

    0 Mountain Pasture Rd Unit 243661, Becket, MA 01223

    Discover your slice of serenity on nearly 2 acres of picturesque wooded land, ideally situated for your dream vacation retreat or primary residence. Nestled along a tranquil privately maintained dirt country road, just a short distance from Route 8, this property offers the perfect blend of seclusion and accessibility.Imagine building your escape amidst the natural beauty of the Berkshires, with

    Samantha Homeyer BIRCH PROPERTIES

    0 Mountain Pasture Rd Unit 243661, Becket, MA 01223
  • /43

    $425,000

    • 3 Beds
    • 1.5 Baths
    • 1,239 Sq Ft

    1178 Bancroft Rd, Becket, MA 01223

    Charming 3BR Cape style home with a beautiful solarium, plus a screened porch located on 11 acres. Sit on a bench and enjoy the babbling brook or listen to it from the heated solarium, the screened porch or the deck. This lovingly cared for home is immaculate with a recently renovated kitchen. The walk-out lower level could easily be finished for additional living space. Nicely located on a quiet

    Jeff Wilkinson STONE HOUSE PROPERTIES, LLC

    1178 Bancroft Rd, Becket, MA 01223
  • /9

    $25,900

    • Land
    • 2.16 Acres
    • $11,991 per Acre

    0 Moberg Rd, Becket, MA 01223

    Spacious 2.16-acre parcel located in the desirable Indian Lake Estates Association. This private community offers access to a pristine non-motorboat lake, perfect for swimming, kayaking, canoeing, and fishing, as well as scenic walking trails for year-round enjoyment. The lot is already build-ready with a recently completed perc test (August 6, 2025), streamlining the process for your future

    Michael Sorrentino BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD

    0 Moberg Rd, Becket, MA 01223
  • /23

    $234,900

    • 2 Beds
    • 1 Bath
    • 860 Sq Ft

    187 Route 20, Chester, MA 01011

    Charming 2-bedroom, 1-bath home tucked away in the peaceful Hill Towns, offering comfort, character, and a scenic natural setting. A beautiful stream runs along the rear of the property, and the small, manageable lot makes upkeep easy while still providing room to enjoy the outdoors. Inside, the home features bright, welcoming spaces ideal for simple, low-maintenance living. Whether you’re

    Timothy Coughlen Park Square Realty

    187 Route 20, Chester, MA 01011
  • /42

    $480,000

    • 4 Beds
    • 2 Baths
    • 2,171 Sq Ft

    500 E River Rd, Chester, MA 01011

    This 1800's farmhouse was once home to The Ideal Shoe Company (Danvers, MA). It's a property rich with history, charm, and situated in the middle of 13+ gorgeous acres fit to explore, or simply revel in their beauty. Surrounded by hundreds of acres of conservation land, your adventures could be endless. Take in the tranquil sounds of the Westfield River while roaming the tree-lined paths or

    Alexis Noyes Brick & Mortar Northhampton

    500 E River Rd, Chester, MA 01011
  • /32

    $380,000

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft

    50 Beach Rd, Becket, MA 01223

    Discover this recently remodeled gem in the Center Pond community. Set on a corner lot, this 3-bedroom, 1-bath home combines modern updates with the charm of a peaceful lake neighborhood. The exterior offers a newer roof, windows, doors, and freshly painted siding. Inside includes an open-concept living space anchored by a stunning new kitchen with sleek cabinetry, butcher block countertops, and

    Cory Evangelisto NOCHER REALTY

    50 Beach Rd, Becket, MA 01223
  • /19

    $519,000

    • 1 Bed
    • 720 Sq Ft

    18 Osceola Dr, Becket, MA 01223

    Unique Opportunity! Lakefront on Center Pond. Original lake cabin built circa 1950 set on .79 acres with 100 feet of lake frontage. Located within 25 feet of the lake the structure will require extensive renovations. The cabin does have electricity and will need well and septic. Great spot and well worth the effort!

    Kim Bergland RED HORSE REAL ESTATE, LLC

    18 Osceola Dr, Becket, MA 01223
  • /4

    $50,000

    • Land
    • 3 Acres
    • $16,667 per Acre

    lot 3 Skyline Trail, Chester, MA 01011

    A great 3-acre parcel on a paved road with stone walls. Lightly forested and flat. This is a relatively easy building site for your new home. Land is just north of 590 Skyline trail.

    James Adams Hilltown Real Estate by Adams Realty

    lot 3 Skyline Trail, Chester, MA 01011
  • /9

    $84,900

    • Land
    • 2.82 Acres
    • $30,106 per Acre

    1 Wade Inn Rd, Becket, MA 01223

    Welcome to Deer Haven, a quiet and scenic community in Becket. This 2.82-acre wooded lot offers the perfect balance of privacy and neighborhood setting. Zoned residential, the property provides plenty of space to design and build your dream home in the Berkshires. A fire hydrant is conveniently located in front of the lot, adding peace of mind for future development. With its natural setting and

    Christian Garner NOCHER REALTY

    1 Wade Inn Rd, Becket, MA 01223
  • /61

    $555,000

    • 4 Beds
    • 3 Baths
    • 2,410 Sq Ft

    674 Benton Hill Rd, Becket, MA 01223

    Escape to this stunning four-bedroom contemporary retreat, nestled on 4.7 serene acres along a quiet country road. The open-concept living area boasts soaring cathedral ceilings, rich hardwood floors, and French doors that lead to an expansive upper deck. The sleek kitchen features stainless appliances, quartz countertops, and a bay window with picturesque views of the wooded backyard. The

    Melinda Boos KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

    674 Benton Hill Rd, Becket, MA 01223
  • /9

    $21,000

    • Land
    • 2.47 Acres
    • $8,502 per Acre

    Lot 26 Stoney Brook Rd, Becket, MA 01223

    Nice level 2.47 acre building lot on a private country road. Good location for a full time or vacation residence. owner is a licensed contractor who can custom build the home you've been dreaming of.

    Kim Bergland RED HORSE REAL ESTATE, LLC

    Lot 26 Stoney Brook Rd, Becket, MA 01223
  • /18

    $578,900

    • 4 Beds
    • 2 Baths
    • 2,244 Sq Ft

    506 Skyline Trail, Chester, MA 01011

    Set along the scenic Skyline Trail, this fully renovated home offers refined finishes, abundant natural light, and an elegant open layout. A long, estate-style concrete approach creates a grand sense of arrival, leading to a beautifully updated interior with porcelain tile floors, modern updates, and two fireplaces that add warmth and character. The finished bonus space just off the main living

    Oleg Abramchuk First NationWide Realty Inc.

    506 Skyline Trail, Chester, MA 01011
  • /12

    $649,900

    • Land
    • 155 Acres
    • $4,193 per Acre

    0 Johnnycake Hill Rd Unit 73378321, Middlefield, MA 01243

    This approximately 155-acre Berkshire nature preserve has enough frontage on Johnnycake Hill Road to accommodate four building lots. Nestled in the beautiful corner of the world where the Pioneer Valley meets the Berkshire Hills, the property is ideal for a myriad of outdoor uses including horseback riding and cross-country skiing. The land contains well over a mile of logging trails and old

    Doug Collins Lamacchia Realty, Inc.

    0 Johnnycake Hill Rd Unit 73378321, Middlefield, MA 01243
  • /41

    $370,000

    • 3 Beds
    • 1.5 Baths
    • 1,792 Sq Ft

    11 Campbell Rd, Chester, MA 01011

    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

    Jessica Sperry Maverick Realty

    11 Campbell Rd, Chester, MA 01011
  • /7

    $25,000

    • Land
    • 2.26 Acres
    • $11,062 per Acre

    Lot 155 Chippewa Dr, Becket, MA 01223

    Come and build your Berkshire dream home in Indian Lake Association. The lot provides for a private country setting with all the amenities of the lake and tennis courts. The private roads throughout the community make for a quiet stroll at any point in time.

    David St. Laurent BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS OTIS

    Lot 155 Chippewa Dr, Becket, MA 01223
  • /8

    $64,900

    • Land
    • 6.73 Acres
    • $9,651 per Acre

    LOT10 Benton Hill Rd, Becket, MA 01223

    6.7 acre parcel with frontage on Center Pond Brook and a fresh October 2025 perc. Private location on a town maintained road. Fiber optic and electric on the street. No HOA. Abutting property also available.

    Kim Bergland RED HORSE REAL ESTATE, LLC

    LOT10 Benton Hill Rd, Becket, MA 01223
  • /5

    $21,000

    • Land
    • 2.17 Acres
    • $9,677 per Acre

    LOT 1B Hopkins Ln, Becket, MA 01223

    Kim Bergland RED HORSE REAL ESTATE, LLC

    LOT 1B Hopkins Ln, Becket, MA 01223
  • /13

    $425,000

    • Land
    • 102.28 Acres
    • $4,155 per Acre

    0 Stoney Brook Rd Unit 245266, Becket, MA 01223

    Discover the Opportunity of owning 102 Acres in Becket! - Step into a world of possibilities with this extraordinary 100 + acres property located in the heart of Becket, Massachusetts. Offering frontage on Stoney Brook Road, Route 8, and Main Street, this expansive parcel is ready to meet your vision. Whether you're dreaming of a private estate or seeking a lucrative development project, this

    Christian Deckert WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    0 Stoney Brook Rd Unit 245266, Becket, MA 01223
  • /2

    $32,900

    • Land
    • 10.16 Acres
    • $3,238 per Acre

    0 Skyline Trail Lot 24, Middlefield, MA 01243

    Over 10 acres of country land available for a private homestead, farming operation, or future development. Here is your unique opportunity to own a piece of New England's scenic beauty nestled in the Berkshires. Whether you're looking for a private retreat, a farm, or investment property, the region provides a mix of rolling hills, forests, and open meadows. Bring your vision for this land!

    Phim Mar Byrnes Real Estate Group LLC

    0 Skyline Trail Lot 24, Middlefield, MA 01243
  • /10

    $39,900

    • Land
    • 4.48 Acres
    • $8,906 per Acre

    Lot19 Skyline Ridge Rd, Becket, MA 01223

    4.48 acre lot in the Skyline Ridge HOA. Potential views to the north. Several existing homes are located nearby with distant mountain and ridge views. Bordering State Forest, lakes, trails and the cultural attractions of the Berkshires nearby. Successful perc test 2003: 2.3 MPI.

    Kim Bergland RED HORSE REAL ESTATE, LLC

    Lot19 Skyline Ridge Rd, Becket, MA 01223
  • /42

    $2,650,000

    • 2 Beds
    • 2.5 Baths
    • 1,183 Sq Ft

    327 Chester Rd, Becket, MA 01223

    Fabulous Estate Property with ponds, rushing streams, huge acreage and a gem of a house. The 220 acres abuts state forest and beautiful Walker & Spark Brooks both run through the property. The 2BR/2.5B home has lovely views of the pond and hills beyond, and was totally renovated to the highest standards in 2023 and 2024. Native stone fireplace, heart pine floors, new kitchen, baths, heating,

    Jeff Wilkinson Jeff Wilkinson

    327 Chester Rd, Becket, MA 01223
  • /40

    $479,000

    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft

    345 Big Bass Ln, Becket, MA 01223

    Nestled between forest and garden in the serene, secluded Crystal Pond neighborhood, this bright and breezy home offers rustic charm, serenity and convenience, & central A/C.The open concept floorplan seamlessly merges the dining, kitchen areas into a vaulted great room that boasts threewalls of windows, and skylights. Two bedrooms, new bath and laundry on the first floor, with a beautiful summer

    Ginger Conner RED HORSE REAL ESTATE, LLC

    345 Big Bass Ln, Becket, MA 01223
  • /2

    $64,500

    • Land
    • 0.41 Acre
    • $157,317 per Acre

    0 Nottingham Cir, Becket, MA 01223

    Breathtaking, developable, lake front property... in Becket’s highly desirable Sherwood Forest boasting 17860 square feet area.. for fun with friends and family all year round.

    Carmelo Calderon Statewide Real Estate Associates, Inc.

    0 Nottingham Cir, Becket, MA 01223
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