8

Chester, MA Homes for Sale under $100,000

Section Image Section Image
  • 91 Lynes Rd, Chester, MA 01011
    91 Lynes Rd, Chester, MA 01011
    91 Lynes 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
  • 95 Lynes Rd, Chester, MA 01011
    95 Lynes Rd, Chester, MA 01011
    95 Lynes Rd, Chester, MA 01011
    /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
  • lot 3 Holcomb Rd, Chester, MA 01011
    lot 3 Holcomb Rd, Chester, MA 01011
    lot 3 Holcomb Rd, Chester, MA 01011
    /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
  • 0 E River Rd Lot 13 Map 409 Unit 72690617, Chester, MA 01050
    0 E River Rd Lot 13 Map 409 Unit 72690617, Chester, MA 01050
    0 E River Rd Lot 13 Map 409 Unit 72690617, Chester, MA 01050
    /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
  • lot 2 Holcomb Rd, Chester, MA 01011
    lot 2 Holcomb Rd, Chester, MA 01011
    lot 2 Holcomb Rd, Chester, MA 01011
    /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
  • lot1 Holcomb Rd, Chester, MA 01011
    lot1 Holcomb Rd, Chester, MA 01011
    lot1 Holcomb Rd, Chester, MA 01011
    /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
  • lot 4 Holcomb Rd, Chester, MA 01011
    lot 4 Holcomb Rd, Chester, MA 01011
    lot 4 Holcomb Rd, Chester, MA 01011
    /4

    $69,000

    • Land
    • 2.5 Acres
    • $27,600 per Acre

    lot 4 Holcomb Rd, Chester, MA 01011

    Prime 2-acre farmland pasture. This is a premium 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 4 Holcomb Rd, Chester, MA 01011
  • Lot 35 Deer Run, Becket, MA 01223
    Lot 35 Deer Run, Becket, MA 01223
    Lot 35 Deer Run, Becket, MA 01223
    /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
Massachusetts Hampden County

Real Estate & Homes in Chester, MA under $100,000

Home Prices in Chester, MA

The median home sale price in Chester, MA is $329,000, up 1% year-over-year. Homes in Chester sell in 52 days on average, compared to the national average of 56 days.

Home Price Trends

Median Sale Price
$329,000
Median Single Family Sale Price
$315,000
Median 2 Bedroom Sale Price
$329,000
Median 1 Bedroom Sale Price
$41,500
Average Price Per Sq Ft
$191
Number of Homes for Sale
4
Last 12 months Home Sales
29
Months of Supply
1.70
Median List Price
$309,999
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
1%
How to Buy a Home How to Finance a Home How to Sell a Home

In Chester, there are currently 8 homes for sale priced under $100,000, providing budget-friendly options for prospective buyers. Whether you're in search of houses for sale under 100k or other property types, there are opportunities to discover your ideal home within your budget in Chester, MA. From cozy starter homes to properties awaiting your personal touch, these affordable residences offer an entry point into the housing market or an opportunity for real estate investment without stretching your finances.

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group