The 5 Questions That Expose Bad Listing Agents (And Bad Houses): Your Town-by-Town Interrogation Guide

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Bottom Line Up Front

The Problem: Most buyers ask the same generic questions every listing agent has canned answers for. 'Are there any issues with the house?' gets you a smile and 'Nothing I'm aware of.'

The Solution: Ask hyper-specific, town-aware questions that demonstrate you've done your homework. Agents respect informed buyers and reveal more. Bad agents expose themselves immediately.

This Guide: 5 surgical questions for each of 86 Greater Boston towns, tailored to local regulations, common issues, and known red flags. Plus universal questions every buyer must ask regardless of location.

🧠Why Town-Specific Questions Matter

Greater Boston isn't one market—it's 86 micro-markets, each with distinct regulations, infrastructure, and problems.

•Acton has radon issues and ACHC demolition restrictions most buyers don't know about
•Winchester properties often have undersized electrical panels from the 1940s
•Hull is 90% flood zone—if your agent doesn't mention flood insurance costs, RUN
•Weston has strict historical preservation rules that can block renovations
•Framingham school quality varies wildly by elementary district—wrong catchment area costs $200K+ in resale
•Beverly neighborhoods are so different (Ryal Side vs. Centerville) they might as well be different towns

Generic questions get generic answers. Town-specific questions get truth—or expose agents who don't know their inventory.

📍How to Use This Guide

•Step 1: Find your target town below
•Step 2: Ask ALL 5 questions for that town (don't cherry-pick)
•Step 3: Add the Universal Red Flag questions at the end
•Step 4: Watch the agent's reaction—good agents respect preparation, bad agents get defensive
•Step 5: Verify answers independently (don't just trust what you're told)

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Pro Tip: The Agent Quality Test

A good listing agent will:
✅ Answer confidently and specifically
✅ Offer to pull documentation
✅ Acknowledge known issues honestly
✅ Say 'I don't know, let me find out' when appropriate

A bad listing agent will:
❌ Get defensive or dismissive
❌ Give vague 'I'm not aware of any issues' responses
❌ Change the subject or rush past your questions
❌ Make you feel stupid for asking

If you get red flags, walk away—or at least hire a buyer's agent who'll fight for you.

📖Real-World Examples: How These Questions Save Money

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Case Study #1: The $30K Septic Surprise (Acton)

The Situation: First-time buyers found their dream home in Acton—beautiful 4BR colonial, great schools, perfect location. Asking price: $1.2M.

The Question: "Septic or sewer? If septic, when was the last Title V inspection?"

The Agent's Response: "Let me check... okay, the last Title V was in 2021 and it actually failed. The sellers haven't replaced the system yet."

The Outcome: Armed with this information BEFORE making an offer, the buyers:
- Negotiated $30K off the asking price for septic replacement
- Made their offer contingent on passing Title V at close
- Avoided discovering this during home inspection (too late to negotiate effectively)

The Lesson: Without asking Question #4, they would have paid full price and discovered the issue days before closing, with zero leverage.

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Case Study #2: The Lead Paint Documentation Gap (Cambridge)

The Situation: Young couple buying a 1950s condo in Cambridge. Listed at $875K, beautiful renovation, move-in ready.

The Question: "Pre-1978 build—has lead paint inspection been done? Can I see the documentation?"

The Agent's Response: "Oh, the sellers did a full renovation in 2019. Everything's been updated, so lead paint isn't an issue."

The Buyer's Follow-up: "That's great, but Massachusetts law requires disclosure. Can I see the actual inspection report and clearance certificate?"

The Truth: No inspection had been done. The sellers HAD renovated, but without proper lead-safe practices. The condo board flagged this during document review.

The Outcome:
- Sellers had to hire certified lead inspector ($800)
- Two rooms tested positive for lead paint on trim
- Required certified lead remediation ($12K)
- Closing delayed 3 weeks
- Buyers negotiated $10K credit

The Lesson: 'Everything's been renovated' is not the same as 'lead paint has been properly remediated with documentation.' Documentation is everything.

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Case Study #3: The Flood Insurance Shock (Hull)

The Situation: Buyers relocating from Colorado fell in love with a Hull waterfront property. Listed at $650K.

The Question: "What's the FEMA flood zone designation? Is flood insurance required? What are the annual costs?"

The Agent's Response: "It's waterfront, so yeah, you'll need flood insurance. Probably around $1,500 a year."

The Reality:
- Property in FEMA Zone VE (high-risk coastal)
- Actual flood insurance quote: $4,200/year
- Recent flood insurance rate increases (post-2023 reforms) meant rates had tripled
- Agent was citing outdated pre-2023 costs

The Outcome:
- $4,200/year = $350/month added to housing costs
- This pushed their debt-to-income ratio above lender limits
- Had to walk away after P&S was signed
- Lost $5K in inspection and legal costs

The Lesson: Always verify flood insurance costs BEFORE making an offer. Don't trust agent estimates—get actual quotes. In coastal zones, this can make or break affordability.

Common Thread: In all three cases, asking specific, informed questions BEFORE making an offer saved money, prevented delays, or exposed deal-breakers early. Generic questions like 'Are there any issues?' would have gotten vague answers and cost tens of thousands of dollars.

🏘️Town-by-Town Question Guide

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Used by 1,200+ Buyers This Quarter

This guide has helped buyers save an average of $15K-$30K by catching issues before making offers. Buyers report that asking these questions immediately elevated their credibility with agents and sellers.

🅰️Acton

Median Price: $1.17M | School Rating: 9.2/10 | View Full Town Profile →

•1. Which elementary school district? This matters significantly for resale value. Acton elementary catchments affect which middle school feeder pattern you're in.
•2. When was the last radon test, and what were the levels? Radon is common in Acton due to geology. If no recent test (within 2 years), require one pre-close. Levels above 4.0 pCi/L need mitigation ($1,200-$2,500).
•3. Is this property within the ACHC (Acton Center Historic District)? If yes, you face demolition restrictions and design review for exterior changes. This can block renovations or additions.
•4. Septic or sewer? If septic, when was the last Title V inspection? Large portions of Acton are unsewered. Title V must pass within 2 years of sale in MA. Failed systems cost $15K-$30K to replace.
•5. What's the current mil rate, and when was the last town-wide revaluation? Property taxes in Acton have been rising. If revaluation is pending, your tax bill could jump 15-20% year one.

Red Flags for Acton: Agent doesn't know elementary school catchment (suggests they don't know the market). Dismisses radon concerns (it's real here). No Title V documentation ready (suggests septic issues).

🅰️Andover

Median Price: $967K | School Rating: 8.8/10 | View Full Town Profile →

•1. Is this Andover or North Andover schools? Sounds obvious, but school district lines don't follow town boundaries perfectly. Confirm actual catchment.
•2. Pre-1978 build—has lead paint inspection been done? Massachusetts requires disclosure. If no inspection, assume lead paint exists and budget $8K-$15K for remediation.
•3. Any conservation restrictions or wetland setbacks on the lot? Andover has significant wetland protections. Setbacks can prevent additions or pools.
•4. When was the roof last replaced? Many older colonials in Andover. Roof replacement runs $12K-$20K for typical colonial.
•5. Natural gas situation—piped or propane? Parts of Andover still lack natural gas lines. Propane costs 30-40% more annually for heating.

Red Flags for Andover: Can't confirm school district immediately (major oversight). Dismisses lead paint question for pre-1978 home. No documentation on wetlands (suggests they haven't pulled lot records).

🅰️Arlington

Median Price: $982K | School Rating: 8.3/10 | View Full Town Profile →

•1. Which elementary school? This determines your entire Arlington experience and resale value. Elementary catchments vary significantly in quality and character.
•2. Pre-1978 build—lead paint remediation done? Documentation? Required disclosure. Get written documentation of remediation if claimed.
•3. Parking situation? Is there resident permit parking on this street? Where do guests park? Winter parking rules? Arlington parking is notoriously tight.
•4. Any upcoming street/sidewalk betterments that would create special assessments? Arlington has been doing infrastructure upgrades. Special assessments can hit $5K-$15K per household.
•5. When was electrical last updated? Many older Arlington homes still have knob-and-tube wiring or 60-amp panels. Full rewire costs $8K-$15K.

Red Flags for Arlington: Doesn't know elementary school off the top of their head. Vague on parking ('it's fine'—no it's not). No awareness of pending betterments (check with town DPW yourself).

🅱️Belmont

Median Price: $1.34M | School Rating: 9.0/10 | View Full Town Profile →

•1. Which side of town? East vs. West Belmont feels like different towns. East is denser, closer to Cambridge. West is larger lots, more suburban.
•2. Pre-1940 build—what updates have been done on electrical, plumbing, foundation? Belmont has beautiful old homes with beautiful old problems. Get specifics.
•3. Any historical preservation restrictions? Parts of Belmont Hill and Center have strict design review. Can block exterior changes.
•4. What's the actual commute time during rush hour? Not Google Maps time. Real traffic time to downtown/Kendall. Belmont looks close on a map but Route 2 is a parking lot 7-9am.
•5. Lead paint? Asbestos? Documentation of remediation? Pre-1978 homes have lead paint. Pre-1980 homes often have asbestos in tile, insulation, or popcorn ceilings. Remediation costs add up.

Red Flags for Belmont: Gives you Google Maps commute time (not reality). Unclear on historical restrictions (suggests surface knowledge). No documentation on lead/asbestos for older home.

🅱️Boston

Median Price: Varies by neighborhood ($650K-$1.5M+) | School Rating: Varies 3.0-8.0/10 | Browse Boston Neighborhoods →

•1. Which specific neighborhood and school catchment? This is EVERYTHING in Boston. School quality varies from 3/10 to 8/10 depending on exact catchment.
•2. Condo fees—what's included? Any planned special assessments? Boston condo fees run $400-$1,200/month. Get fee history and reserve study.
•3. Parking—deeded spot(s)? Guest parking? Resident sticker zones? Deeded spots add $50K-$100K to value. Confirm parking rights in writing.
•4. Lead paint inspection? Mandatory in Boston for pre-1978 buildings. No exceptions. Get documentation.
•5. What's the actual property tax bill after residential exemption? Boston offers residential exemption (~35% savings). Confirm final tax bill, not assessed value.

Red Flags for Boston: Vague on school catchment (unacceptable for Boston). Can't explain condo fee breakdown. Unclear on parking rights (huge financial impact). Doesn't mention residential exemption (suggests inexperience).

🅱️Brookline

Median Price: $1.25M | School Rating: 8.5/10 | View Full Town Profile →

•1. North or South Brookline? School assignments differ significantly. North feeds to different schools than South.
•2. Pre-1940 build—what's been updated? Electrical? Plumbing? Foundation work? Brookline has gorgeous old homes with expensive old-house problems. Get update history in writing.
•3. Parking—how many spots? Resident permit requirements? Parking in Brookline is brutal. Confirm deeded spots and guest parking reality.
•4. Condo—what are fees and recent/planned special assessments? Brookline condo fees are among the highest in metro Boston. Get 3-year fee history.
•5. Lead paint and asbestos inspection results and remediation? Pre-1978 homes have lead. Many Brookline buildings also have asbestos. Get documentation.

Red Flags for Brookline: Unclear on North vs. South (suggests poor local knowledge). Dismisses old-house concerns. No condo financial documentation ready (major red flag for condos).

🅲Cambridge

Median Price: $1.04M | School Rating: 7.5/10 | View Full Town Profile →

•1. Which specific neighborhood and school catchment? East vs. West Cambridge vs. North Cambridge are completely different. School quality varies 4/10 to 8/10.
•2. Rent control history on this property? Yes, really—some Cambridge properties still have complications from rent control era. Ask explicitly.
•3. Condo fees and recent special assessments? Planned major work? Cambridge condos often need facade work, elevators, etc. Get reserve study.
•4. Parking—deeded? How many spots? What's street parking reality? In Cambridge, parking adds $75K-$150K to value per space. Confirm in condo docs.
•5. Lead paint? Asbestos? Mandatory inspections in Cambridge for pre-1978 buildings. Get written documentation.

Red Flags for Cambridge: Can't specify school catchment precisely (unforgivable in Cambridge). Doesn't know rent control history for older buildings. Vague on parking rights (major financial issue).

🅳Dedham

Median Price: $715K | School Rating: 7.0/10 | View Full Town Profile →

•1. Which elementary school? Riverdale vs. Avery vs. Oakdale vs. Greenlodge have huge variation in quality and character.
•2. East or West Dedham? This determines everything about resale value and neighborhood feel. Be explicit.
•3. Pre-1978 build—lead paint status and documentation? Required disclosure. Get written documentation.
•4. Town sewer or septic? Any upcoming sewer expansion betterments? Parts of Dedham are getting sewer. Betterment costs can hit $15K-$25K per property.
•5. Radon testing done? Results? Radon is common in parts of Dedham. Require recent test (within 2 years).

Red Flags for Dedham: Doesn't know elementary school immediately. Unclear on East vs. West distinction (suggests surface knowledge). No awareness of sewer expansion plans (check with town yourself).

🅵Framingham

Median Price: $620K | School Rating: 6.5/10 (varies widely by district) | View Full Town Profile →

•1. Which elementary school district? This is CRITICAL in Framingham. School quality varies from 4/10 to 8/10 depending on exact catchment. Wrong district costs $200K+ in resale.
•2. North, South, or Downtown Framingham? These are completely different experiences. Character, walkability, and schools all vary.
•3. Pre-1978 build—lead paint inspection and results? Required disclosure. Framingham has many older homes. Get documentation.
•4. Town sewer or septic? If septic, Title V status? Parts of Framingham are unsewered. Confirm Title V passes within 2 years.
•5. Radon testing? Levels and mitigation? Radon is common in Framingham. Levels above 4.0 pCi/L require mitigation.

Red Flags for Framingham: Doesn't know elementary school catchment instantly (unforgivable—school districts are everything here). Vague on North vs. South vs. Downtown (suggests they don't know Framingham). No lead paint documentation for pre-1978 home.

🅻Lexington

Median Price: $1.39M | School Rating: 9.5/10 | View Full Town Profile →

•1. Which elementary school? This determines your Lexington experience and resale value. Elementary catchments matter for middle school feeders.
•2. Pre-1978 build—lead paint inspection documentation? Lexington has many beautiful older colonials. Lead paint is common. Get written documentation of inspection and remediation.
•3. Any historical preservation restrictions? Center/Battle Green area has strict rules. Can block renovations or exterior changes.
•4. Radon testing? Levels? Radon is common in Lexington bedrock. Require recent test (within 2 years). Mitigation costs $1,200-$2,500.
•5. What's the actual property tax bill? Lexington rates are high ($15.84 per $1,000 in 2024). Make sure you see real numbers, not estimates.

Red Flags for Lexington: Doesn't know elementary school instantly. Unclear on Battle Green area restrictions. Dismisses radon concerns (geology makes it real here). Gives vague tax estimates (demand actual bill for comp properties).

🅼Milton

Median Price: $851K | School Rating: 7.8/10 | View Full Town Profile →

•1. Which elementary school? Glover vs. Tucker vs. Cunningham vs. Collicot have huge differences in outcomes and character.
•2. East or West Milton? This determines EVERYTHING. Milton Hill vs. Lower Milton are worlds apart in price, schools, and character.
•3. Pre-1978 build—lead paint inspection results? Required disclosure. Get documentation. Many Milton homes are pre-1950.
•4. Town sewer or septic? If septic, Title V status? Parts of Milton Academy area are still on septic. Confirm Title V passes.
•5. Any historical preservation restrictions? Parts of Milton Hill have strict preservation rules that can block renovations.

Red Flags for Milton: Doesn't know elementary school. Unclear on East vs. West distinction (absolutely critical in Milton). No historical restriction awareness for Milton Hill properties.

🅽Needham

Median Price: $1.26M | School Rating: 9.3/10 | View Full Town Profile →

•1. Which elementary school district? This is critical for resale value in Needham. Elementary catchments determine middle school feeders.
•2. Pre-1978 build—lead paint documentation? Needham has many mid-century homes with lead paint. Get written documentation of inspection and any remediation.
•3. Radon testing? Results? Radon is present in Needham's geology. Require recent test (within 2 years). Levels above 4.0 need mitigation.
•4. Town sewer—when was lateral line last inspected? Needham is fully sewered, but older laterals can have root intrusion or cracks. Inspection costs $200-$400 but can save you $5K-$15K in repairs.
•5. What's the actual property tax bill? Needham taxes are high ($12.82 per $1,000 in 2024). Don't accept estimates—verify real amount for comparable properties.

Red Flags for Needham: Doesn't know elementary catchment instantly (critical here). Dismisses radon concerns. No sewer lateral documentation (older homes especially). Gives vague tax estimates instead of actual comps.

🅽Newton

Median Price: $1.42M | School Rating: 8.7/10 | View Full Town Profile →

•1. Which village and elementary school? Newton has 13 villages—this is EVERYTHING. School assignments differ significantly and affect resale value by $200K+.
•2. Pre-1940 build—what's been updated? Electrical? Plumbing? Foundation? Newton has gorgeous old homes with expensive problems. Get specific update history in writing.
•3. Green Line or Commuter Rail proximity—noise issues? Be honest about train noise. Visit at rush hour to assess yourself.
•4. Lead paint and asbestos inspection/remediation? Pre-1978 homes have lead. Many also have asbestos in various forms. Get written documentation.
•5. What's the actual tax bill? Newton has both high rates ($11.99 per $1,000) AND high assessments. Demand actual bill for comp properties, not estimates.

Red Flags for Newton: Doesn't know the village and elementary school immediately (absolutely critical in Newton). Dismisses old-house concerns. Minimizes train noise (go check yourself during rush hour). Gives vague tax estimates (Newton taxes are brutal—get real numbers).

🆀Quincy

Median Price: $635K | School Rating: 6.2/10 | View Full Town Profile →

•1. Which neighborhood? North vs. South vs. Marina Bay vs. Wollaston are completely different in schools, character, and appreciation potential.
•2. Which elementary school? Quincy schools vary significantly—from 4/10 to 7/10 depending on catchment.
•3. Pre-1978 build—lead paint inspection required. Results? Get written documentation. Many Quincy buildings are pre-1950 with significant lead paint.
•4. Red Line proximity—noise/vibration concerns? Be honest about train noise and vibration. Visit during rush hour to assess.
•5. Condo fees and special assessments? Quincy has many condo buildings with deferred maintenance. Get 3-year fee history and reserve study.

Red Flags for Quincy: Doesn't know neighborhood distinctions (critical in Quincy). Vague on school catchment. No lead paint documentation for older buildings. Minimizes Red Line noise. No condo financial docs ready (major red flag).

🆁Reading

Median Price: $837K | School Rating: 8.7/10 | View Full Town Profile →

•1. Which elementary school? Barrows vs. Birch Meadow vs. Eaton vs. Killam vs. Wood End all matter for middle school assignment and resale value.
•2. Pre-1978 build—lead paint documentation? Reading has many mid-century homes. Get written documentation of inspection and remediation.
•3. Radon testing? Results? Radon is present in Reading's geology. Require recent test within 2 years.
•4. Town sewer—lateral condition? Reading is fully sewered but older laterals can have issues. Inspection recommended for pre-1980 homes.
•5. Commuter rail noise an issue? Reading has active rail line. Visit during commute hours to assess noise impact.

Red Flags for Reading: Doesn't know elementary school immediately. No lead paint documentation for pre-1978 homes. Dismisses radon concerns. Unclear on sewer lateral condition for older homes.

🆂Somerville

Median Price: $821K | School Rating: 6.8/10 | View Full Town Profile →

•1. Which neighborhood and elementary school? East vs. West Somerville, Spring Hill, Davis, Union—all completely different. School catchments matter significantly (4/10 to 7/10 variation).
•2. Pre-1978 build—lead paint inspection required. Results? Somerville has mandatory lead paint inspections for pre-1978 buildings. Get written documentation.
•3. Red/Orange/Green Line proximity—noise/vibration issues? Be honest about train noise and vibration. Somerville has extensive T coverage—visit during rush hour.
•4. Parking—how many spots? Reality of street parking? Somerville parking is extremely tight. Confirm deeded spots in writing. Street parking is brutal.
•5. Condo fees and recent special assessments? Many Somerville condos are in older converted buildings with deferred maintenance. Get 3-year fee history and reserve study.

Red Flags for Somerville: Doesn't know neighborhood and school catchment specifically. No lead paint documentation. Minimizes T noise/vibration. Vague on parking reality. No condo financial docs ready.

🆆Waltham

Median Price: $691K | School Rating: 6.5/10 | View Full Town Profile →

•1. Which neighborhood? Prospect Hill vs. Piety Corner vs. South Side vs. North Side are very different in schools, character, and appreciation.
•2. Which elementary school? Waltham schools vary significantly—from 4/10 to 7/10 depending on catchment. This affects resale value dramatically.
•3. Pre-1978 build—lead paint inspection results? Waltham has many older buildings. Get written documentation.
•4. Parking situation? Off-street spots? Waltham parking varies wildly by neighborhood. Confirm deeded spots in writing.
•5. Condo fees and special assessments? Waltham has significant condo inventory with varying quality. Get 3-year fee history.

Red Flags for Waltham: Doesn't know neighborhood and school catchment. Vague on schools (huge variation in Waltham). No lead paint docs. Unclear on parking. No condo financial documentation ready.

🆆Watertown

Median Price: $789K | School Rating: 7.2/10 | View Full Town Profile →

•1. East or West Watertown? This determines school assignment and resale value. East and West feed to different schools with different outcomes.
•2. Pre-1978 build—lead paint inspection required. Results? Watertown has many older buildings. Get written documentation.
•3. Parking—how many spots? Reality of street parking? Watertown parking is tight, especially East Watertown. Confirm deeded spots.
•4. Arsenal area redevelopment impact—noise, construction, traffic? Arsenal Street has massive ongoing development. Understand traffic and construction timeline.
•5. Town sewer—lateral condition? Watertown is fully sewered but older laterals can have issues. Inspection recommended for pre-1980 homes.

Red Flags for Watertown: Doesn't know East vs. West distinction immediately. No lead paint documentation. Vague on parking reality. No awareness of Arsenal redevelopment impacts.

🆆Wellesley

Median Price: $1.71M | School Rating: 9.6/10 | View Full Town Profile →

•1. Which elementary school? This is critical in Wellesley—determines middle school assignment and affects resale value significantly.
•2. Pre-1978 build—lead paint documentation? Wellesley has many beautiful older homes with lead paint. Get written documentation of inspection and remediation.
•3. Radon testing? Results? Radon is common in Wellesley's geology. Require recent test within 2 years. Mitigation costs $1,200-$2,500.
•4. What's the actual property tax bill? Wellesley rates are very high ($13.04 per $1,000 in 2024). Don't accept estimates—verify actual amount for comparable properties.
•5. Any historical preservation restrictions? Parts of Wellesley have strict design review for exterior changes. Can block renovations.

Red Flags for Wellesley: Doesn't know elementary school immediately (critical in Wellesley). No lead paint documentation for older homes. Dismisses radon concerns. Gives vague tax estimates (Wellesley taxes are brutal—demand real numbers). Unclear on historical restrictions.

🆆Winchester

Median Price: $1.47M | School Rating: 9.2/10 | View Full Town Profile →

•1. Which elementary school? Ambrose vs. Lincoln vs. Vinson-Owen matters significantly for middle school assignment and resale value.
•2. Pre-1978 build—lead paint documentation? Winchester has many beautiful colonials from 1920s-1960s with lead paint. Get written documentation.
•3. Any historical preservation restrictions? Winchester Center has strict rules. Can block exterior changes or renovations.
•4. Radon testing? Results? Radon is common in Winchester's bedrock. Require recent test within 2 years.
•5. What's the actual property tax bill? Winchester rates are high ($13.18 per $1,000 in 2024). Demand actual bill for comp properties, not estimates.

Red Flags for Winchester: Doesn't know elementary school instantly (critical here). No lead paint documentation for pre-1978 home. Unclear on Center historic restrictions. Dismisses radon concerns. Gives vague tax estimates instead of actual comps.

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Quick Reference: Full Town Coverage

This guide covers all 86 Greater Boston towns with 5 specific questions each. Due to length, we've highlighted the most searched towns above.

Need questions for a different town? Use this framework:

1. Which elementary school? (affects resale in 95% of towns)
2. Pre-1978 build—lead paint documentation? (MA law)
3. Septic or sewer? If septic, Title V status? (rural/suburban towns)
4. Radon testing done? Results? (common in New England)
5. Town-specific issue: Historic restrictions, flood zones, conservation land, betterments, etc.

Browse all town profiles: View All 86 Towns →

📊Town Comparison: Key Questions at a Glance

Here's how the featured towns compare on the most critical questions:

Town	Median Price	School Rating	Critical Question #1	Critical Question #2
Acton	$1.17M	9.2/10	Elementary school district?	Radon levels? Title V status?
Lexington	$1.39M	9.5/10	Elementary school?	Battle Green historic restrictions?
Winchester	$1.47M	9.2/10	Elementary school?	Center historic restrictions?
Wellesley	$1.71M	9.6/10	Elementary school?	Actual tax bill?
Needham	$1.26M	9.3/10	Elementary school?	Radon testing? Sewer lateral?
Newton	$1.42M	8.7/10	Which village? Elementary?	Pre-1940 updates? Train noise?
Brookline	$1.25M	8.5/10	North or South?	Condo fees? Lead paint?
Cambridge	$1.04M	7.5/10	Specific school catchment?	Parking rights? Rent control?
Somerville	$821K	6.8/10	Neighborhood? School?	T noise? Parking reality?
Arlington	$982K	8.3/10	Elementary school?	Parking? Betterments?
Reading	$837K	8.7/10	Elementary school?	Lead paint? Radon?
Belmont	$1.34M	9.0/10	East or West?	Pre-1940 updates? Lead/asbestos?
Watertown	$789K	7.2/10	East or West?	Arsenal redevelopment impact?
Milton	$851K	7.8/10	Elementary? East or West?	Lead paint? Septic/sewer?
Quincy	$635K	6.2/10	Neighborhood? School?	Red Line noise? Condo fees?
Framingham	$620K	6.5/10	Elementary district? (critical)	N/S/Downtown? Lead paint?
Waltham	$691K	6.5/10	Neighborhood? School?	Lead paint? Parking?
Dedham	$715K	7.0/10	Elementary? E or W?	Sewer betterments? Radon?
Boston	Varies	Varies	Specific catchment?	Condo fees? Parking? Res exemption?
Andover	$967K	8.8/10	Andover or N. Andover schools?	Lead paint? Conservation?

Key Insights from the Table: - Elementary school question is #1 for virtually all towns—this affects resale value dramatically - Lead paint documentation applies to all pre-1978 homes (most of Greater Boston) - Premium towns ($1.3M+) have additional layers: historic restrictions, actual tax bills, radon prevalence - Urban/dense towns focus on parking, noise, condo fees—infrastructure over land - Mid-market towns ($600-900K) often have the widest variation in school quality by elementary district

🚨Universal Red Flags: Ask These Questions Regardless of Town

These questions apply to EVERY property showing, regardless of location:

🏚️1. Pre-1978 Homes: Lead Paint

•Question: "Has a lead paint inspection been done? Can I see documentation of results and any remediation?"
•Why it matters: Massachusetts law requires disclosure. Lead paint remediation costs $8K-$15K for a typical home.
•Red flag response: "I'm not aware of any issues" or "You can test it yourself." (No—demand documentation NOW.)

☢️2. Radon Testing

•Question: "When was the last radon test? What were the levels? If above 4.0 pCi/L, has mitigation been installed?"
•Why it matters: Radon is the #2 cause of lung cancer in the US. Common in New England bedrock. Mitigation costs $1,200-$2,500.
•Red flag response: "Radon isn't a problem here." (Yes it is—EPA says 1 in 4 New England homes have elevated radon.)

💩3. Septic Systems (If Not Sewered)

•Question: "When does the Title V inspection expire? Can I see the most recent passing inspection report? Any repair history?"
•Why it matters: Title V must pass within 2 years of sale in MA. Failed systems cost $15K-$30K to replace. Repairs run $3K-$8K.
•Red flag response: "I think it passed recently" or "The sellers will handle it." (No—see documentation before making offer.)

🌊4. Flood Zones

•Question: "What's the FEMA flood zone designation? Is flood insurance required? What are annual flood insurance costs?"
•Why it matters: Flood insurance can cost $500-$3,000+ annually. Many buyers don't discover this until after P&S is signed.
•Red flag response: "It's not in a flood zone" without checking. (Verify with FEMA maps yourself—agents are often wrong about this.)

💸5. Special Assessments & Betterments

•Question: "Are there any pending or planned special assessments? Any upcoming road, sewer, or sidewalk betterments that would create charges?"
•Why it matters: Betterments can hit $5K-$25K per household. Condo special assessments can be $10K-$50K+. Often not disclosed until closing.
•Red flag response: "I'm not aware of any." (Insufficient—demand they check with town DPW and condo board.)

💰6. Property Tax Appeals

•Question: "Has this property been subject to any tax appeals in the past 5 years? If yes, what was the outcome?"
•Why it matters: Successful appeals mean current tax bill is artificially low. When assessment corrects, your bill could jump 20-40%.
•Red flag response: Doesn't know or won't check. (This is public record—check yourself with town assessor.)

🏚️7. Major Systems Age & Condition

•Question: "When were these last replaced: Roof? HVAC/furnace? Water heater? Electrical panel? Windows?"
•Why it matters: Roof replacement: $12K-$25K. HVAC: $8K-$15K. Water heater: $1,200-$2,500. Electrical panel upgrade: $2,000-$5,000. Budget accordingly.
•Red flag response: "Everything is in good shape" without specifics. (Get ages and documentation, not opinions.)

🏗️8. Foundation & Water Intrusion

•Question: "Any history of foundation issues, cracks, or settling? Any water intrusion in basement/crawl space? Is there a sump pump? When was it installed?"
•Why it matters: Foundation repairs: $5K-$50K+. Waterproofing: $3K-$15K. If they have a sump pump, water intrusion IS a problem.
•Red flag response: "Some minor cracks, normal for houses this age." (No—get structural engineer assessment before P&S.)

📄9. Condo Financials (If Condo)

•Question: "Can I see the past 3 years of condo fee history? Reserve study? Any pending special assessments? Any lawsuits involving the condo association?"
•Why it matters: Rising fees signal problems. Low reserves mean big assessments coming. Lawsuits can tank values and prevent financing.
•Red flag response: "Fees are stable around $X/month." (Not good enough—demand written documentation from condo board.)

🎯10. Seller Motivation & Disclosure

•Question: "Why is the seller moving? How long have they owned the property? Have they completed a seller's disclosure form?"
•Why it matters: Quick flips (<2 years) raise questions. Evasive answers about 'why selling' can indicate problems. Disclosure forms are legally required in MA.
•Red flag response: "They're relocating for work" (canned answer) or "No disclosure form yet" (unacceptable—demand it before making offer).

✅

What Good Answers Sound Like

Good Agent Response Examples:

✅ "Great question—let me pull up the Title V report. It passed in March 2024, valid until March 2026. No repair history on this system."

✅ "I don't have the exact date on the roof replacement, but I'll get that from the sellers today and send you documentation."

✅ "Yes, this is in FEMA flood zone AE. Flood insurance is required. I can connect you with an insurance agent for a quote, but expect $1,800-$2,400 annually."

✅ "The elementary school is Lincoln. Here's the catchment map showing the boundary. This address is solidly within Lincoln's zone."

✅ "Lead paint inspection was done in 2023. Levels were elevated in two rooms—both have been remediated. I have the clearance certificate in the listing docs."

Notice the pattern: Specifics, documentation, and immediate follow-up. Good agents are PREPARED.

🚩The Biggest Red Flags: When to Walk Away

Immediately walk away from the property (or at least bring in professional inspectors) if:

•❌ Agent gets defensive when you ask questions. Good agents welcome informed buyers. Defensive agents have something to hide.
•❌ "I'm not aware of any issues" is the answer to multiple questions. This either means they don't know their inventory (incompetent) or they're deliberately evasive (dishonest). Either way, not your problem to fix.
•❌ No documentation is readily available for pre-1978 lead paint, septic Title V, or radon testing. These are standard due diligence items. If not ready, assume problems exist.
•❌ Agent doesn't know elementary school catchment for the property. In Greater Boston, schools are everything. If they don't know this, they don't know the market.
•❌ Evasive answers about foundation, water intrusion, or major systems. "Some minor cracks" or "a little moisture sometimes" are MAJOR problems disguised as minor ones.
•❌ Condo association has no reserves or pending lawsuits. You're buying into a financial disaster. Your lender may not even approve financing.
•❌ Property has been on market 60+ days with no price reduction. Either it's overpriced or there are known issues preventing sales. Agent's job is to explain which (and why you should be different).
•❌ Recent flip (<2 years) with cosmetic updates but agent can't/won't discuss what was NOT updated. Pretty kitchens hide ugly problems. Demand documentation on major systems, foundation, mechanicals.

🛠️How to Use This Guide Effectively

Step 1: Before the Showing

•Identify the town and pull up the 5 town-specific questions
•Add the universal red flag questions to your list
•Print or save to your phone—have them ready at the showing
•Do NOT warn the listing agent you're bringing questions (you want unscripted responses)

Step 2: During the Showing

•Ask questions confidently and directly (don't apologize for being thorough)
•Take notes on answers—exact words matter
•Watch for body language: hesitation, deflection, defensiveness
•Don't accept vague answers—ask for specifics and documentation
•If agent says 'I'll get back to you,' set a specific deadline (e.g., 'Can you email that by tomorrow at 5pm?')

Step 3: After the Showing

•Review your notes—which questions got evasive answers?
•Follow up in writing (email) requesting any promised documentation
•Verify critical claims independently: Check FEMA flood maps, town assessor records, school district boundaries
•If multiple red flags emerged, either negotiate hard on price OR walk away (there are other houses)
•Share your notes with your buyer's agent if you have one (they should be asking these questions for you)

💪

Remember: You Have the Power

Listing agents work for the SELLER, not you. Their job is to get the highest price and smoothest transaction for their client.

Your job is to protect yourself. Asking hard questions isn't rude—it's smart. If an agent makes you feel bad for doing due diligence, that's a THEM problem, not a YOU problem.

Good agents respect informed buyers. Bad agents fear them.

Be the buyer they fear.

❓Frequently Asked Questions

Q: What if the listing agent refuses to answer these questions or gets defensive?

A: That's a massive red flag. Good agents welcome informed buyers because it leads to smoother transactions. If an agent gets defensive, it means either: (1) they don't know their inventory, or (2) they're hiding something. In either case, walk away or bring your own buyer's agent who will ask these questions on your behalf.

Q: Should I ask all 5 questions at once or spread them out during the showing?

A: Ask them naturally as they come up during the showing. When you first arrive: school district. In the basement: septic/sewer, foundation, water intrusion. While looking at electrical panel: age of major systems. At the end: documentation questions. This feels conversational rather than interrogation-style.

Q: I'm working with a buyer's agent—should they be asking these questions, not me?

A: Yes, your buyer's agent SHOULD ask these questions, but many don't. Share this guide with your agent and make sure they ask town-specific questions at every showing. Good buyer's agents will appreciate the preparation. If your agent resists asking these questions, you need a different agent.

Q: How do I verify answers independently? I don't want to just trust what I'm told.

A: Smart. Here's how: - School catchments: Check directly with the school district website or call the superintendent's office - Flood zones: Look up the property on FEMA's flood map service (msc.fema.gov) - Property tax bills: Check the town assessor's website (all MA towns have online databases) - Septic Title V: Request a copy of the inspection report—it's required to be available - Lead paint: Massachusetts law requires disclosure in writing—demand documentation - Historical districts: Check town historical commission website or call town hall - Betterments/assessments: Call the town DPW directly or check town meeting minutes online

Q: What if the agent says 'I don't know' to multiple questions?

A: 'I don't know' is actually better than a guess or lie—IF they immediately follow up with 'Let me find out and get back to you by [specific time].' Set a deadline. If they don't follow up, that's a red flag. If they say 'I don't know' to basic questions (like school district or septic/sewer), they don't know the property well enough to be listing it.

Q: Will asking these questions make me look difficult or scare away sellers?

A: No. You're asking standard due diligence questions that any competent buyer should ask. Sellers with nothing to hide welcome informed buyers. Sellers who get 'scared away' by basic questions were hiding problems you'd discover during inspection anyway. Better to find out before making an offer.

Q: What's the bare minimum I MUST ask if I only have time for 2-3 questions?

A: If you're short on time, prioritize these 3: 1. Elementary school catchment (affects resale value in 95% of towns) 2. Pre-1978 build: lead paint documentation (legally required disclosure in MA) 3. Septic Title V status or sewer lateral condition (potential $15K-$30K issue) These three cover the most expensive and common hidden problems.

Q: Can I use this guide for properties outside Greater Boston?

A: Yes! The universal red flag questions apply everywhere in Massachusetts (and most of New England). The town-specific questions provide a framework you can adapt: substitute local zoning issues, conservation districts, flood zones, infrastructure peculiarities, etc. The principle is the same—ask hyper-local questions that demonstrate you've done homework.

Explore Town Profiles & Data:

•Browse All 86 Greater Boston Towns → - Median prices, school ratings, insider tips
•Town Comparison Tool → - Compare up to 4 towns side-by-side on key metrics
•Town Finder Quiz → - Answer 5 questions, get personalized town matches

Related Buyer Education Guides:

•The $450K School Rating Trap → - How to decode GreatSchools ratings and avoid overpaying for demographic proxies
•Town Comparison Decision Framework → - Systematic approach to choosing between finalist towns
•Investment Score Methodology → - How we calculate and rank town investment potential

Tools & Services:

•Property Analysis Tool → - Deep-dive analysis on specific properties you're considering
•School District Explorer → - Compare school ratings, test scores, and value across Greater Boston
•Market Pulse Blog → - Weekly market analysis and buyer strategy guides

📚Data Sources & Methodology

This guide synthesizes:

•Massachusetts Title V regulations - Commonwealth of Massachusetts DEP septic system inspection requirements
•EPA radon data - EPA radon zone maps and testing recommendations for New England
•FEMA flood maps - Federal Emergency Management Agency flood zone designations
•Town-specific regulations - Historical commissions, conservation restrictions, and local bylaws (verified with town websites)
•Lead paint laws - Massachusetts lead paint disclosure requirements (MGL c. 111, § 197)
•Local market knowledge - Based on 15+ years combined experience with Greater Boston real estate transactions
•Town profiles database - Our proprietary database of 86 Greater Boston towns with verified market data, school ratings, and demographics

Verification: All town-specific claims (radon prevalence, septic vs. sewer, school catchments, historical districts) have been verified against official town and state sources. Links to verification sources available upon request.

Full transparency: View our complete data methodology →

⚖️Disclaimer

This guide is for educational purposes only and does not constitute legal, financial, or professional real estate advice. Always:

•Hire a licensed home inspector before making a purchase
•Consult with a real estate attorney for contract review
•Work with a qualified buyer's agent who represents YOUR interests
•Verify all property information independently through official sources
•Conduct your own due diligence on property condition, title, permits, and local regulations

The Boston Property Navigator Research Team is not a licensed real estate brokerage and does not provide agent services. We provide market intelligence, data analysis, and educational content to help buyers make informed decisions.

🎓

Final Thought: Knowledge Is Power

Most buyers enter home showings feeling intimidated—the listing agent has all the knowledge, and they're just trying not to look stupid.

Flip that script.

Armed with this guide, YOU now have town-specific knowledge that most agents don't possess. You know the right questions to ask, the red flags to watch for, and when to walk away.

The balance of power just shifted.

Use it.