Homes, values and local insight for Montgomery, Hampden County, Massachusetts. Typical home value $458,000.
Reviewed and updated October 3, 2026 by Ryan and Megan Winslow, Winslow Homes
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Montgomery is a distinctive Massachusetts community that offers residents a blend of local character, quality amenities, and regional convenience.
The Montgomery 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 Montgomery 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 Montgomery 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 Montgomery
Properties with lake, pond, or reservoir access where available in Montgomery.
Homes near local waterways offering natural settings and scenic views.
What Every Buyer Must Know
Some areas of Montgomery near waterways may fall in AE flood zones. Verify specific property with FEMA flood map.
Moderate flood risk exists in select Montgomery areas near wetlands or drainage basins.
Most Montgomery 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 Montgomery
Steady appreciation and rental demand make Montgomery suitable for long-term wealth building.
Rental demand in Montgomery supports cash flow strategies for single-family and multifamily properties.
Older properties in Montgomery offer value-add opportunities through renovation and modernization.
Montgomery 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 Montgomery 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 Montgomery to nearby cities via major roads and highways.
Montgomery residents commute to regional metropolitan areas for employment and entertainment.
Montgomery supports remote workers with reliable broadband access, quiet residential settings, and home office-friendly properties.
Your Dollar in Montgomery
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 Montgomery aligns with regional Massachusetts averages. Housing remains the largest expense category.
Homeowners insurance in Montgomery averages $1,200-$2,500 annually. Coverage varies by property age, value, and risk factors.
Living the Montgomery Life
Montgomery offers parks, trails, and outdoor recreation opportunities year-round.
Local restaurants, cafes, and cultural venues provide community gathering spaces in Montgomery.
Local retail, services, and major shopping areas accessible within and near Montgomery.
Employment & Economic Drivers
Retail, professional services, and hospitality anchor the Montgomery economy.
Residents also commute to regional employment centers for professional opportunities.
Remote work grows as a major economic factor in Montgomery, supported by quality broadband and home-office friendly properties.
Getting Around Montgomery
Montgomery connects to major highways and arterials providing access to regional destinations.
Montgomery offers walkable neighborhoods and bike-friendly areas in the town center and residential zones.
Montgomery residents access regional airports within reasonable driving distance for domestic and international travel.
What's Coming to Montgomery
Expanding development areas bringing new construction to Montgomery.
The Montgomery market outlook remains positive with steady demand, moderate appreciation, and balanced inventory conditions expected through 2026.
Real Estate Investment in Montgomery
Pre-approve financing before searching. Work with Montgomery-focused agents.
Long-term holds in Montgomery 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 Montgomery 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 Montgomery is worth $458,000, 29% above the Hampden County typical value of $355,000 and 31% below the Massachusetts typical value of $662,000.
Zillow Home Value Index for Montgomery, August 2026. The middle of the market for single family homes and condos.
Home values in Montgomery moved +26.8% over five years and +72.6% over ten.
Share of occupied homes in Montgomery lived in by the owner.
Older homes often need inspection focus on roof, systems and windows.
Median household income in Montgomery.
Median age of residents in Montgomery.
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 Montgomery home of $458,000:
Ryan and Megan price Montgomery homes from recent sales, not guesses. Send your address and you get a free market analysis, with no obligation.
Typical value $352,000 · 1,640 residents
Area guide →Typical value $359,000 · 2,071 residents
Area guide →Typical value $503,000 · 6,181 residents
Area guide →Typical value $310,000 · 1,221 residents
Area guide →Typical value $378,000 · 1,209 residents
Area guide →Typical value $389,000 · 40,403 residents
Area guide →See the full Hampden County real estate guide or the Massachusetts real estate guide.
The Zillow Home Value Index for Montgomery was $458,000 in August 2026, +5.2% over the past year.
Montgomery is in Hampden County, Massachusetts.
About 837 people as of the 2024 Census Bureau estimate, up from 821 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.
97% of occupied homes in Montgomery 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 Montgomery, MA before they hit the big home search sites.
