The $250K Liberal Tax: Why Massachusetts Progressives Pay Double for Less House

This isn't cherry-picking. It's a pattern that repeats across Greater Boston—and it raises an uncomfortable question:

Are the most progressive towns in Massachusetts also the least affordable? And are the towns shifting rightward offering the best value for family-sized homes?

The answer, backed by voting records and property data, is yes. But the why is more complicated—and more interesting—than simple partisan politics.

Let's look at more comparisons to establish the pattern.

The pattern is clear: Towns that shifted Republican offer significantly better value for family-sized homes. Even when comparing two Democratic towns (Canton vs. Milton), the more Democratic one costs 38% more—showing that political alignment correlates with price, even within the same party.

The trade-off is stark: Space and privacy vs. location and transit access. But the price gap—$250K to $400K—is substantial. For the same budget, you get 2.6x to 3.7x more living space in towns that shifted Republican.

Before anyone accuses this of partisan point-scoring, let's be clear: This isn't about whether Democrats or Republicans have better housing policies. The pattern emerges from structural economic and geographic forces that correlate with—but aren't caused by—political affiliation.

Here's what's really driving the "liberal tax":

1. Location, Location, Location

The most expensive towns in Greater Boston share one thing: proximity to Boston, Cambridge, and major job centers.

• Brookline abuts Boston
• Cambridge is Boston-adjacent with Red Line access
• Milton borders Boston neighborhoods
• Newton is inside I-95

These towns command premiums because they minimize commute times for high-earning professionals working in Kendall Square (biotech), Longwood Medical Area (healthcare), and Financial District (finance/law).

Towns like Hanover, Pembroke, and Marshfield are 30-45 minutes out. That distance creates a natural price discount—regardless of voting patterns.

But here's the political correlation: High-earning professionals in knowledge industries (tech, healthcare, academia, law) cluster in urban-adjacent towns and vote overwhelmingly Democratic. Their housing demand drives up prices in those areas.

2. Transit Access Premium

Every Greater Boston town with direct MBTA Red/Orange/Green Line access commands a premium:

• Brookline (Green Line): $777/sqft
• Cambridge (Red Line): $900+/sqft
• Somerville (Red/Orange Lines): $850/sqft
• Arlington (near Red Line): $700/sqft

• Towns without rapid transit:
• Hanover: $407/sqft
• Pembroke: $387/sqft
• Canton: $445/sqft

The T access alone adds $250-$400/sqft premium. And transit-accessible towns vote heavily Democratic.

This isn't because Democrats inherently prefer transit—it's because urban professionals who use transit vote Democratic and bid up prices in those neighborhoods.

3. Zoning & Supply Constraints

Here's where progressive housing policy meets regressive outcomes.

• The most Democratic towns in Greater Boston have:
• Stricter zoning laws (historic preservation, environmental review)
• More restrictive permitting (lengthy approval processes)
• Lower housing production (NIMBY resistance to multifamily)
• Higher barriers to entry (minimum lot sizes, setback requirements)

Example: Brookline, Cambridge, and Newton all have strong progressive voting records—and some of the most restrictive zoning in Massachusetts.

• Meanwhile, towns like Hanover and Pembroke have:
• Simpler permitting (less bureaucracy)
• Larger developable parcels (available land)
• More flexible zoning (easier to build)

The irony: Towns that vote for affordable housing policies at the state level often have local zoning that constrains supply and raises prices.

This isn't hypocrisy—it's the collective action problem of housing. Residents support affordable housing in theory, but oppose new construction in their neighborhood (traffic, character, density concerns).

4. Demographics & Self-Selection

Greater Boston is experiencing political geographic sorting—people increasingly live near those who share their values.

• Liberal-leaning households prioritize:
• Walkability and transit access
• Urban amenities (restaurants, culture, nightlife)
• Diversity and density
• Proximity to universities and hospitals

• Conservative-leaning households prioritize:
• Larger homes and private yards
• Car-dependent suburbs
• Lower taxes and smaller government
• Traditional family-oriented communities

• This self-selection creates a feedback loop:
• Progressive professionals cluster in urban-adjacent towns
• Their demand drives up prices
• Working-class and middle-class families move outward for affordability
• Outer suburbs become more conservative
• The price gap widens

The 2024 shift: Hanover, Pembroke, and Marshfield all shifted 5-9 points toward Republicans. But this doesn't mean residents became more conservative—it likely reflects demographic turnover as middle-class families priced out of blue towns moved to affordable red/purple suburbs.

5. School Quality vs. School Prestige

One hypothesis: Expensive liberal towns have better schools, justifying higher prices.

The data says otherwise.

• Look at school ratings:
• Hanover (R+3): 8.0/10
• Brookline (D+73): 8.3/10
• Pembroke (R+2.8): 6.5/10
• Cambridge (D+77): 7.8/10
• Canton (D+28): 8.2/10
• Milton (D+38): 8.8/10

The school quality gap is 0.3-1.3 points—far smaller than the $250K-$600K price gap.

And as we've documented in our Achievement Gap analysis, 84% of MCAS score variation is explained by demographics, not instructional quality.

Translation: Expensive towns have high test scores because they attract affluent families—not because they have dramatically better teaching. A middle-class child will receive a comparable education in Hanover (8.0/10) as in Brookline (8.3/10).

Yet Brookline costs $250K more.

The most progressive towns in Massachusetts—the ones that vote 70-85% Democratic, support rent control, advocate for affordable housing, and champion equity—are also the least affordable for working- and middle-class families.

Let's be blunt:

• Cambridge (D+77): Median household income $128K, median home price $1.2M+
• Brookline (D+73): Median income $128K, median home price $1.025M
• Newton (D+59): Median income $167K, median home price $1.5M+
• Lexington (D+60): Median income $219K, median home price $1.3M+

These towns are politically progressive but economically exclusive. Their residents advocate for housing equity statewide while local zoning ensures only the wealthy can afford to live there.

• Meanwhile:
• Hanover (R+3): Median income $175K, median home price $775K
• Pembroke (R+2.8): Median income $110K, median home price $620K
• Canton (D+28): Median income $154K, median home price $725K

These moderate and conservative-leaning towns are more affordable for middle-class families—not because of political philosophy, but because of location, transit access, and zoning.

The paradox: If you're a progressive family with a $150K household income and want a 4BR home with a yard, you're more likely to find affordability in a town that just voted for Trump.

And if you're a working-class family making $75K-$100K? You're effectively priced out of the most progressive towns entirely.

The 2024 election data reveals something significant: Towns that shifted Republican are the affordable suburbs.

• Rightward shift (2020 → 2024):
• Hanover: D+6 → R+3 (9-point shift)
• Pembroke: D+6 → R+2.8 (8.8-point shift)
• Marshfield: D+10 → D+5.1 (4.9-point shift)
• Plymouth: D+12 → D+6 (6-point shift)

These are the towns where middle-class families can still afford to buy. They're 30-40 minutes from Boston, have good (not elite) schools, and offer space for growing families.

• Solidly blue (no shift):
• Brookline: D+76 → D+73 (stable)
• Cambridge: D+78 → D+77 (stable)
• Newton: D+63 → D+59 (stable)

These are the towns where only high earners can buy. They're 10-20 minutes from Boston, have excellent (often prestige) schools, and offer walkability and transit.

The correlation is clear: As housing affordability decreases, towns shift rightward. As prices rise and density increases, towns stay blue.

This isn't about ideology—it's about who can afford to live where.

If you're a prospective buyer navigating Greater Boston's market, here's what this analysis reveals:

1. The "Liberal Tax" Is Real, But It's a Location Tax

• You're not paying $250K extra because Brookline votes Democratic. You're paying extra because:
• It abuts Boston (10-minute drive to Longwood Medical)
• It has Green Line access (car-free lifestyle possible)
• It has urban amenities (Coolidge Corner, restaurants, culture)
• It has limited land (dense, can't build outward)

The value proposition: If you prioritize walkability, transit, urban life, and shorter commute, Brookline delivers—at a steep price.

The alternative: If you prioritize space, privacy, yard, and are OK with 30-minute car commute, Hanover delivers—at half the price per sqft.

2. School Quality Is More Uniform Than Prices Suggest

The gap between 8.0/10 (Hanover) and 8.3/10 (Brookline) schools is marginal. Both are good. Both will prepare your kids for college.

As our Achievement Gap research shows, wealthy districts don't teach better—they select wealthier students who score higher.

Implication: Don't overpay $250K for a 0.3-point school rating difference. Invest that money in your retirement or 529 plan instead.

3. Political Sorting Is Accelerating

If community values matter to you, visit both types of towns:

• Solid blue towns (D+50+): Tend to be diverse, dense, progressive, with younger populations and renter majorities
• Purple/red towns (R+5 to D+10): Tend to be family-oriented, car-dependent, suburban, with older populations and homeowner majorities

Neither is "better"—they're different. And increasingly, they're economically and politically segregated.

4. Use the Town Comparison Tool

Don't guess. Compare directly:

Compare Hanover vs. Brookline →

Compare Pembroke vs. Cambridge →

Compare Canton vs. Milton →

Compare Marshfield vs. Sharon →

See side-by-side data on prices, schools, commute, crime, demographics, and community character.

The biggest irony in all of this?

The most progressive towns in Massachusetts—the ones that vote overwhelmingly for affordable housing policies at the state and federal level—have the most regressive local zoning.

• They advocate for:
• Rent control
• Inclusionary zoning
• Tenant protections
• Affordable housing mandates

• But their local policies ensure:
• Single-family zoning dominance
• High minimum lot sizes
• Lengthy permitting processes
• NIMBY resistance to multifamily construction

The result: Housing supply is constrained, prices rise, and only the wealthy can afford to live there.

As we documented in Greater Boston's Housing Crisis, Massachusetts needs 13,000+ new homes per year but permits only 6,800 single-family homes annually statewide—and that number is falling.

Who builds? Towns like Hanover, Pembroke, and Canton—where zoning is more flexible and land is available.

Who doesn't build? Towns like Brookline, Cambridge, and Newton—where zoning is restrictive and residents oppose new construction.

The towns that need more housing the most build the least. The towns with space and affordability build the most.

So where does that leave you as a buyer?

• If you're politically progressive, do you:
• Stretch your budget to live in an expensive blue town that aligns with your values—but buy less space?
• Move to an affordable red/purple town that offers better value—but live among neighbors who vote differently?

• If you're politically conservative, do you:
• Accept higher prices to live in a job-rich urban area—even if the politics don't align?
• Prioritize affordability and move outward—even if the commute is longer?

There's no right answer. Housing decisions involve trade-offs:

• Space vs. Location
• Commute vs. Budget
• Transit vs. Driving
• Urban vs. Suburban
• Diversity vs. Homogeneity
• Walkability vs. Privacy

• And increasingly:
• Political Alignment vs. Economic Reality

The "liberal tax" in Greater Boston is real. Towns that vote 70-85% Democratic cost $250K-$600K more than towns that shifted Republican in 2024.

• But it's not about politics per se. It's about:
• Location (proximity to Boston and job centers)
• Transit access (MBTA Red/Orange/Green Line stops)
• Zoning (restrictive permitting and limited supply)
• Demographics (self-selection and economic sorting)
• Market forces (high-earning professionals clustering in urban areas)

The uncomfortable truth: The most progressive towns in Massachusetts are the least affordable. And the towns shifting rightward are the ones where middle-class families can still buy a home.

This isn't a moral judgment. It's a market reality.

And it raises a question for progressive voters: If housing equity matters, shouldn't the first step be allowing more housing in the towns that need it most?

Until then, the "liberal tax" will keep growing. And the political geography of Greater Boston will continue to sort by income, not just by ideology.

Want to explore towns by your priorities—not just politics or price? Use our Town Finder Tool to discover the best-fit towns based on your budget, commute, school needs, and lifestyle preferences.

Need a side-by-side comparison? Try our Town Comparison Tool to see detailed data on any Greater Boston towns.