Homes, values and local insight for Chesterfield, Hampshire County, Massachusetts. Typical home value $407,000.
Reviewed and updated October 3, 2026 by Ryan and Megan Winslow, Winslow Homes
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Chesterfield is a distinctive Massachusetts community that offers residents a blend of local character, quality amenities, and regional convenience.
The Chesterfield real estate market serves a range of buyers including first-time homeowners, growing families, professionals, and retirees. Properties include single-family homes, condominiums, and townhouses across various price points and styles that reflect the area's architectural heritage and modern development.
Winslow Homes LLC and Ryan & Megan Winslow serve Chesterfield buyers and sellers across Massachusetts. Ryan and Megan Winslow provide both real estate brokerage and mortgage services as Mortgage Bankers with The Federal Savings Bank (Ryan Winslow NMLS #2426605 | Megan Winslow NMLS #2692933). Get pre-approved at www.winslowloan.com or call 386-690-5858.
Explore Chesterfield Neighborhoods
Historic center with local shops, dining, and civic institutions.
Residential area with established neighborhoods and good school access.
Quiet residential streets with a mix of homes and convenient commuter access.
Expanding area with newer construction and family-friendly amenities.
Unique Property Types in Chesterfield
Properties with lake, pond, or reservoir access where available in Chesterfield.
Homes near local waterways offering natural settings and scenic views.
What Every Buyer Must Know
Some areas of Chesterfield near waterways may fall in AE flood zones. Verify specific property with FEMA flood map.
Moderate flood risk exists in select Chesterfield areas near wetlands or drainage basins.
Most Chesterfield properties are in Zone X (minimal flood risk). Flood insurance optional but may be recommended.
Insurance Tip: Massachusetts homeowners insurance averages $1,500-$2,200 annually. Coastal properties may need additional windstorm coverage.
Real Estate Investment in Chesterfield
Steady appreciation and rental demand make Chesterfield suitable for long-term wealth building.
Rental demand in Chesterfield supports cash flow strategies for single-family and multifamily properties.
Older properties in Chesterfield offer value-add opportunities through renovation and modernization.
Chesterfield investment risks include regional market volatility, property tax changes, and insurance cost increases. Work with experienced agents to assess individual opportunities.
Where New Homes Are Being Built
New development zones on the outskirts of Chesterfield offer modern construction and newer floor plans.
Buyer Tips for New Construction: Always hire your own inspector for new builds. Review CDD obligations carefully. Negotiate upgrades, not price. A buyer's agent costs you nothing with new construction and provides critical representation.
Drive Times & Work-From-Anywhere
Convenient access from Chesterfield to nearby cities via major roads and highways.
Chesterfield residents commute to regional metropolitan areas for employment and entertainment.
Chesterfield supports remote workers with reliable broadband access, quiet residential settings, and home office-friendly properties.
Your Dollar in Chesterfield
Massachusetts property tax averages 1.14% statewide. Senior citizen and veteran exemptions available. Residential tax rate varies by town.
Massachusetts has a flat 5% income tax rate plus a 4% surtax on income over $1M (effective 2023). Property tax rates vary by municipality. The residential exemption in some communities reduces the assessed value of owner-occupied homes. No sales tax on clothing under $175.
Cost of living in Chesterfield aligns with regional Massachusetts averages. Housing remains the largest expense category.
Homeowners insurance in Chesterfield averages $1,200-$2,500 annually. Coverage varies by property age, value, and risk factors.
Living the Chesterfield Life
Chesterfield offers parks, trails, and outdoor recreation opportunities year-round.
Local restaurants, cafes, and cultural venues provide community gathering spaces in Chesterfield.
Local retail, services, and major shopping areas accessible within and near Chesterfield.
Employment & Economic Drivers
Retail, professional services, and hospitality anchor the Chesterfield economy.
Residents also commute to regional employment centers for professional opportunities.
Remote work grows as a major economic factor in Chesterfield, supported by quality broadband and home-office friendly properties.
Getting Around Chesterfield
Chesterfield connects to major highways and arterials providing access to regional destinations.
Chesterfield offers walkable neighborhoods and bike-friendly areas in the town center and residential zones.
Chesterfield residents access regional airports within reasonable driving distance for domestic and international travel.
What's Coming to Chesterfield
Expanding development areas bringing new construction to Chesterfield.
The Chesterfield market outlook remains positive with steady demand, moderate appreciation, and balanced inventory conditions expected through 2026.
Real Estate Investment in Chesterfield
Pre-approve financing before searching. Work with Chesterfield-focused agents.
Long-term holds in Chesterfield benefit from regional appreciation trends.
DISCUSS INVESTMENT STRATEGY
Avoid These Costly Errors
Get pre-approved with Ryan & Megan Winslow, Mortgage Bankers with The Federal Savings Bank, before shopping.
Budget for taxes, insurance, HOA, and maintenance beyond the mortgage payment.
A local Chesterfield agent knows which streets flood, which buildings have pending special assessments, and which neighborhoods are appreciating fastest. Buyer agent services are free to the buyer in most transactions.
The typical home in Chesterfield is worth $407,000, 10% below the Hampshire County typical value of $455,000 and 38% below the Massachusetts typical value of $662,000.
Zillow Home Value Index for Chesterfield, August 2026. The middle of the market for single family homes and condos.
Home values in Chesterfield moved +26.9% over five years and +75.0% over ten.
Median gross rent in Chesterfield. Useful for investors running rental numbers.
Share of occupied homes in Chesterfield lived in by the owner.
Older homes often need inspection focus on roof, systems and windows.
Median household income in Chesterfield.
Ryan and Megan are mortgage bankers with The Federal Savings Bank, lending in all 50 states. You get the home and the loan from one team. On a typical Chesterfield home of $407,000:
Ryan and Megan price Chesterfield homes from recent sales, not guesses. Send your address and you get a free market analysis, with no obligation.
Typical value $401,000 · 942 residents
Area guide →Typical value $412,000 · 1,181 residents
Area guide →Typical value $477,000 · 1,629 residents
Area guide →Typical value $446,000 · 2,475 residents
Area guide →Typical value $359,000 · 2,071 residents
Area guide →Typical value $392,000 · 819 residents
Area guide →See the full Hampshire County real estate guide or the Massachusetts real estate guide.
The Zillow Home Value Index for Chesterfield was $407,000 in August 2026, +0.6% over the past year.
Chesterfield is in Hampshire County, Massachusetts.
About 1,174 people as of the 2024 Census Bureau estimate, compared with 1,187 in 2020.
Ryan and Megan Winslow of Winslow Homes have sold over 3,000 homes since 2009 and are licensed in Florida, Massachusetts, Connecticut and Rhode Island. Call or text 386-690-5858.
Apply at www.winslowloan.com. Ryan and Megan are mortgage bankers with The Federal Savings Bank and lend in all 50 states, including FHA, VA and conventional loans.
88% of occupied homes in Chesterfield are owner occupied, based on the 2019 to 2023 American Community Survey.
17 years, over 3,000 homes sold, and one team for the home and the loan. Call or text 386-690-5858.
Sources: U.S. Census Bureau 2024 population estimates and 2019 to 2023 American Community Survey; Zillow Home Value Index, August 2026. Numbers update as new data is released. Talk to Ryan and Megan for current sold prices on your street.
No in-person meeting or phone call needed for most addresses. See your estimated value, price range and value trend in seconds.
Get coming-soon homes, pocket listings and price drops in Chesterfield, MA before they hit the big home search sites.
The typical home in Chesterfield is worth $404,523 as of August 2026 in ZIP code 01012. Values moved +0.0% over the last 12 months at the middle ZIP code.
| ZIP | Typical value | 12 months | 5 years | Median sale, Mar to May 2026 | Days on market |
|---|---|---|---|---|---|
| 01012 | $404,523 | +0.0% | +26.0% |
Sources: Zillow Home Value Index through August 2026 and the Redfin Data Center ZIP code tracker, March to May 2026. Ask Ryan and Megan for a value for your own home.
