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Homes for Sale near Chester Elementary School

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  • /56

    $759,000

    • 4 Beds
    • 2.5 Baths
    • 3,199 Sq Ft

    707 Benton Hill Rd, Becket, MA 01223

    Welcome to this large expansive dwelling that features great privacy! Enjoy outdoor cooking and refreshments on the enlarged deck for these hot summer days. Also featuring a separate personal deck off the Primary bedroom. This great home boasts an oversized living room with a Grand fireplace place that will impress any viewer. An interior balcony from the sizable Primary Bedroom overlooks the

    Agent Photo

    Cristian Sanchez

    COHEN & WHITE ASSOCIATES

    707 Benton Hill Rd, Becket, MA 01223
  • /3

    $50,000

    • Land
    • 3.54 Acres
    • $14,124 per Acre

    95 Lynes Rd, Chester, MA 01011

    Is this 3.54 acre lot shouting your name? Down an unpaved, tree-lined road lies this wooded lot awaiting its new owner. Looking for some small town charm? Chester is known as the "Gem of the Valley." It is home to a variety of activities and amenities, such as the Chester on Track festival, the Railway Museum, a longstanding theatre company, and the Keystone Arch Bridges Trail. Public records and

    Agent Photo

    Cheryl Malandrinos

    HB Real Estate, LLC

    95 Lynes Rd, Chester, MA 01011
  • /10

    $68,500

    $7K PRICE DROP
    • Land
    • 10.1 Acres
    • $6,782 per Acre

    L45 Jacobs Ladder Rd, Becket, MA 01223

    Discover the serene beauty of the Berkshires with this 10.1-acre property, complete with a babbling stream and old stone walls, providing plenty of privacy for your retreat. This ideal location offers easy access to the best of Becket and the Berkshires, including the renowned Jacob's Pillow Dance Festival and the scenic trails of October Mountain State Forest. Whether you're looking to swim in

    Agent Photo

    Gary Fuls Jr

    Gary L Fuls DBA Re/MAX Transit

    L45 Jacobs Ladder Rd, Becket, MA 01223
  • /39

    $365,000

    $50K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 2,832 Sq Ft

    56 Middlefield Rd, Chester, MA 01011

    The price has improved! Don't miss out. 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

    Agent Photo

    Cynthia Gonzalez

    Executive Real Estate, Inc.

    56 Middlefield Rd, Chester, MA 01011
  • /3

    $50,000

    • Land
    • 3.47 Acres
    • $14,409 per Acre

    91 Lynes Rd, Chester, MA 01011

    Discover 3.47 acres of wooded land tucked along a tree-lined, unpaved road in Chester, known as the "Gem of the Valley." Chester offers a blend of small-town charm and outdoor recreation, from the Chester on Track festival and the Railway Museum to the Keystone Arch Bridges Trail and a vibrant local theatre community. Public records identify the parcel as residential (use code 130). If you’ve

    Agent Photo

    Cheryl Malandrinos

    HB Real Estate, LLC

    91 Lynes Rd, Chester, MA 01011
  • /31

    $439,900

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,460 Sq Ft

    859 Moberg Rd, Becket, MA 01223

    Indian Lakes property with gorgeous lakes two beaches for swimming or kayaking &clay tennis courts. This log sided 3 bedrooms 2bath cabin sits in the Hill towns of Becket, Middle of the Berkshires easy to get to Stockbridge, Gt Barrington 3 ski areas 7 lakes and October State forest.2 new baths and new kitchen with stainless appliances and granite counter tops is ready to show. Cozy up to

    Agent Photo

    Ginger Conner

    RED HORSE REAL ESTATE, LLC

    859 Moberg Rd, Becket, MA 01223
  • /4

    $35,000

    • Land
    • 2.58 Acres
    • $13,566 per Acre

    25 Deer Run, Becket, MA 01223

    Welcome to 25 Deer Run in Becket, MA. This beautiful, buildable lot offers the perfect blend of privacy and natural surroundings. The property previously received a passing perc test, which has since expired, providing a strong starting point for future development plans. Nestled among mature trees and scenic landscapes, the lot offers a peaceful setting to enjoy throughout the year. Conveniently

    Brendan Hanna Coldwell Banker Realty - Western MA

    25 Deer Run, 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. - Dalton

    0 Johnny Cake Hill Rd Unit 246420, Middlefield, MA 01243
  • /42

    $264,900

    • 2 Beds
    • 2 Baths
    • 1,758 Sq Ft

    162 Skyline Trail, Middlefield, MA 01243

    Step back in time without sacrificing modern comfort in this charming antique home, originally built in 1783. Thoughtfully updated to preserve its historic character, this home features exposed timber frame construction, wide-open living spaces, and timeless architectural details throughout. The inviting eat-in kitchen offers a farmhouse sink, vaulted ceiling, gas fireplace, open shelving,

    Aimee Kelly eXp Realty LLC

    162 Skyline Trail, Middlefield, MA 01243
  • /5

    $60,000

    • Land
    • 2.12 Acres
    • $28,302 per Acre

    lot 3 Holcomb Rd, Chester, MA 01011

    Open land. Prime 2-acre pasture, building lot with stone walls on a quiet gravel road. Property rear is bordered by protected conservation land, One of 4 lots available.

    James Adams Hilltown Real Estate by Adams Realty

    lot 3 Holcomb Rd, Chester, MA 01011
  • /11

    $15,000

    • Land
    • 3.56 Acres
    • $4,213 per Acre

    Lot 35 Deer Run, Becket, MA 01223

    Very private wooded lot at the end of the cul de sac in the Deer Haven community (HOA). Bargain priced estate sale, being sold as is. Buyers to do their own due diligence. No camping or RV use per town bylaws.

    Kim Bergland RED HORSE REAL ESTATE, LLC

    Lot 35 Deer Run, Becket, MA 01223
  • /49

    $2,750,000

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

    327 Chester Rd, Becket, MA 01223

    Fabulous Property with ponds, rushing streams, huge acreage & 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 & hills beyond, and was totally renovated to the highest standards in 2023 & 2024. Native stone fireplace, heart pine floors, new kitchen, baths, heating, mahogany decks,

    Jeff Wilkinson STONE HOUSE PROPERTIES, LLC

    327 Chester Rd, Becket, MA 01223
  • /40

    $415,000

    • 3 Beds
    • 3 Baths
    • 1,403 Sq Ft

    143 E River Rd, Huntington, MA 01050

    Welcome to this contemporary home that features 3 bedrooms, 3 bathrooms, and sits on a sprawling 9.8-acre lot. The property offers stunning Westfield River and mountain views, a wrap-around deck, an above-ground pool, and a mostly finished walkout basement- this space offers an in-law apartment, use your imagination to personalize to your needs. This could be your own private retreat at the base

    Danielle Lafond Berkshire Hathaway HomeServices Realty Professionals

    143 E River Rd, Huntington, MA 01050
  • /19

    $449,000

    $50K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 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
  • /28

    $235,000

    Pre-Foreclosure
    • 6 Beds
    • 2 Baths
    • 4,132 Sq Ft

    6 Maple St, Chester, MA 01011

    This is an outstanding opportunity to buy at well below market value. Both units are in move in condition however a septic system will need to be installed at the buyer's expense. Each unit is very expansive with three bedrooms in each unit. Over 4,000 square feet of living area. Many updates including newer furnaces. This is a very smart investment for a cash buyer or a rehab type loan to remedy

    James Adams Hilltown Real Estate by Adams Realty

    6 Maple St, Chester, MA 01011
  • /9

    $19,000

    $6K PRICE DROP
    • Land
    • 2.15 Acres
    • $8,837 per Acre

    00 William Holmes Rd, Becket, MA 01223

    Build your dream home on a 2.15-acre corner lot located in the peaceful Deerhaven neighborhood of East Becket, sitting right at the junction of William Holmes Road and Wade Inn Road. This vacant land offers enormous road frontage and scenic views, making it an absolute dream layout for builders and buyers alike. Town assessor’s formal cyclical inspection in 2024, property was officially verified

    Derek Greene The Greene Realty Group

    00 William Holmes Rd, Becket, MA 01223
  • /37

    $534,900

    $65K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,960 Sq Ft

    554 Main St, Becket, MA 01223

    Becket at its BEST! This beautifully maintained 1,900 sq. ft. ranch offers easy single-level living with a bright, wide-open floor plan filled with natural light. The welcoming kitchen features marble countertops, while the custom fireplace and gorgeous hardwood floors add warmth and charm throughout the home. The spacious walkout basement includes both a Smith furnace and Fire Chief wood stove,

    Audrey Matys BERKSHIRE LISTINGS

    554 Main St, Becket, MA 01223
  • /7

    $75,000

    $5K PRICE DROP
    • 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

    $25K PRICE DROP
    • 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
  • /41

    $375,000

    • 3 Beds
    • 3 Baths
    • 1,512 Sq Ft

    732 Main St, Becket, MA 01223

    Move right into this beautifully renovated 3-bedroom, 3-bath ranch on a picturesque 1-acre lot in the heart of Becket. Designed for comfortable one-level living with central A/C, the home offers a flexible floor plan with additional living space featuring its own private entrance, ideal for guests, a home office, hobbies, or whatever fits your lifestyle. Enjoy a full walkout basement, an

    Ed Rich BISHOP WEST REAL ESTATE

    732 Main St, Becket, MA 01223
  • /4

    $45,000

    • Land
    • 2.06 Acres
    • $21,845 per Acre

    lot 2 Holcomb Rd, Chester, MA 01011

    Prime 2 acre building lot with stone walls on a quiet gravel road. Property rear is bordered by protected conservation land , One of 4 lots available.

    James Adams Hilltown Real Estate by Adams Realty

    lot 2 Holcomb Rd, Chester, MA 01011
  • /15

    $22,000

    • Land
    • 2.19 Acres
    • $10,046 per Acre

    0 Bonny Rigg Hill Rd, Becket, MA 01223

    Easily developed two acre lot in Indian Lake Estates with a 68 acre lake, four scenic and well maintained beaches and Har-Tru tennis. Quality perc's and down sloping terrain for a walk-out build. Potential views and old stone foundation walls that will integrate nicely into a landscaping plan. Close proximity to Jacob's Pillow International Dance Festival and other Berkshire cultural events!

    Henry Hagenah OCTOBER MOUNTAIN REAL ESTATE

    0 Bonny Rigg Hill Rd, Becket, MA 01223
  • /42

    $450,000

    Open House 8/08 $20K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,068 Sq Ft

    147 Chipman Rd, Chester, MA 01011

    Welcome home to this peaceful & serene 3 bed, 2.5 bath contemporary offering an open floor plan, main-level primary suite, & a private trail leading to the wild streambed of Glendale Brook! Enter through the welcoming foyer to the main level that features a spacious living room & dining area w/ propane stove & sliders to a sunny deck, a kitchen with pantry closet, half bath w/ laundry, a

    Taylor Hildack Keller Williams Realty

    147 Chipman Rd, Chester, MA 01011
  • /35

    $135,000

    • Land
    • 9.89 Acres
    • $13,650 per Acre

    258 Captain Whitney Rd, Becket, MA 01223

    Nearly 10 acre surveyed lot set on lightly travelled Captain Whitney Road. If you've ever thought of building a house in the woods this property is ready and able to help make that dream come true. Much of the heavy site work is done: lot cleared, driveway in, well drilled, three bedroom never-used septic system -septic tank & leach field installed (2022), cellar hole dug & foundation slab poured

    Kim Bergland RED HORSE REAL ESTATE, LLC

    258 Captain Whitney Rd, Becket, MA 01223
  • /49

    $675,000

    $55K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 1,890 Sq Ft

    135 Mallard Dr, Becket, MA 01223

    Welcome to your private retreat in the Crystal Pond community, set on just over 2 acres of beautifully wooded privacy. This 4-bedroom, 3.5-bath residence blends refined comfort with natural serenity, offering a true Berkshire escape.Soaring cathedral ceilings, skylights, and expansive windows fill the home with natural light, highlighting rich wood plank flooring and a warm, elevated design

    Jennifer Maxwell Lamacchia Realty, Inc. - Dalton

    135 Mallard Dr, Becket, MA 01223
  • /49

    $499,000

    • 3 Beds
    • 3 Baths
    • 1,536 Sq Ft

    454 Seneca Dr, Becket, MA 01223

    Enjoy Lake living in the Indian Lake Estates Community! This 3 Bedroom 3 Bath Contemporary style home offering privacy and year-round recreational living. Open floor plan, vaulted ceiling, fireplace on approximately 2 acres. Short walk across the street to access the community beach to the beautiful 68 acre Indian Lake!

    Matt Carlino MACCARO REAL ESTATE

    454 Seneca Dr, Becket, MA 01223
  • /38

    $264,900

    $21K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,968 Sq Ft

    254 Route 20, Chester, MA 01011

    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

    Dennis LeClair RE/MAX Compass

    254 Route 20, 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
  • /8

    $449,000

    $50K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 720 Sq Ft

    18 Osceola Rd, 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

    18 Osceola Rd, Becket, MA 01223
  • /7

    $22,001

    • Land
    • 2.58 Acres
    • $8,528 per Acre

    Lot32 Valley View Rd, Becket, MA 01223

    Great place to build on this 2.5 acre lot in the Skyline Ridge Home Owner's Association, a neighborhood of custom built homes established in 2004.. The community is tucked off main roads and set in Berkshire woodlands. Wit frontage on both Valley View and Skyline Ridge roads the property is an excellent location for a new construction with a full walkout lower level. Lakes, trails and Berkshire

    Kim Bergland RED HORSE REAL ESTATE, LLC

    Lot32 Valley View Rd, Becket, MA 01223
  • /14

    $39,900

    • Land
    • 2.38 Acres
    • $16,765 per Acre

    LOT 7 Skyline Ridge Rd, Becket, MA 01223

    Discover a rare opportunity to own a private, wooded homesite in the heart of the Berkshires. This 2.38 acre parcel on Skyline Ridge Road offers the perfect canvas to build a refined country retreat or modern getaway surrounded by natural beauty and tranquility. Set within a peaceful residential enclave, the property provides an ideal balance of seclusion and accessibility. Gently sloping terrain

    Dennis LeClair RE/MAX Compass

    LOT 7 Skyline Ridge Rd, Becket, MA 01223
  • /3

    $45,000

    • Land
    • 2.03 Acres
    • $22,167 per Acre

    lot1 Holcomb Rd, Chester, MA 01011

    Prime 2 acre building lot with stone walls on a quiet gravel road. Property rear is bordered by protected conservation land , One of 4 lots available.

    James Adams Hilltown Real Estate by Adams Realty

    lot1 Holcomb Rd, Chester, MA 01011
  • /7

    $74,900

    • Land
    • 2.02 Acres
    • $37,079 per Acre

    87 Stony Brook Lane Rd, Becket, MA 01223

    Build your dream home in the heart of the Berkshires! Builder's flat lot located in a PRIVATE country community. Yearly fee @ See document tab-@$575 yearly is for road & snow maintenance, insurance & reserves. Great location for full time or vacation residence. Owner is a licensed contractor who can build custom build exactly what your looking for!This property offers the connivence of an

    Donna DiGrigoli DIGRIGOLI REAL ESTATE

    87 Stony Brook Lane Rd, Becket, MA 01223
  • /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 Home Owner's Association, a neighborhood of custom built homes established in 2004. The lot features potential northerly views with clearing. Several nearby existing homes enjoy 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. Thinking of building?

    Kim Bergland RED HORSE REAL ESTATE, LLC

    Lot19 Skyline Ridge Rd, Becket, MA 01223
  • /9

    $49,900

    • Land
    • 4.33 Acres
    • $11,524 per Acre

    Lot 18 Skyline Ridge Rd, Becket, MA 01223

    View lot on Skyline Ridge Road. Great views to the northwest from the 4 plus acre lot on a private road. Take a drive up the road to get a sense of the potential views. 2003 perc. Annual fee of $800.00 for road maintenance. Perc, covenants and survey can be seen in document tabs.

    Kim Bergland RED HORSE REAL ESTATE, LLC

    Lot 18 Skyline Ridge Rd, Becket, MA 01223
  • /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
  • /8

    $89,000

    $9K PRICE DROP
    • Land
    • 13,939 Sq Ft
    • $278,125 per Acre

    LOT112 Osceola Dr, Becket, MA 01223

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

    Kim Bergland RED HORSE REAL ESTATE, LLC

    LOT112 Osceola Dr, Becket, MA 01223
  • /32

    $360,000

    • 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, new countertops, and stainless

    Cory Evangelisto NOCHER REALTY

    50 Beach Rd, Becket, MA 01223
  • /7

    $115,900

    • Land
    • 16.62 Acres
    • $6,974 per Acre

    0 Old Chester Rd (Rear), Blandford, MA 01008

    Opportunity awaits on Old Chester Road in Blandford! Discover 16+ acres of peaceful, wooded land offering privacy, serenity, and endless potential. Approx. 300 ft of driveway has already been cleared, providing easy access into the property and a valuable head start for future plans. With a mostly level landscape, approx. 710 ft of frontage, and no wetlands per seller, this property offers a

    Andrea DeRose NextHome Elite Realty

    0 Old Chester Rd (Rear), Blandford, MA 01008
  • /55

    $499,000

    • 3 Beds
    • 2 Baths
    • 2,084 Sq Ft

    283 Benton Hill Rd, Becket, MA 01223

    Nice 3 bedroom contemporary home set on over nine acres with Center Pond Brook flowing past the garden areas & through the back yard. The front porch opens onto the main kitchen & living areas with hardwood floors & cathedral ceilings. French doors lead to the sunroom overlooking the garden areas. The first floor primary bedroom features two walk in closets, built in dressers & desk. More built

    Kim Bergland RED HORSE REAL ESTATE, LLC

    283 Benton Hill Rd, Becket, MA 01223

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