Is condo life with cafés at your door the right fit, or will a backyard and easy parking make you happier long term? In Boston, that choice often comes down to your monthly costs, your commute, and how much maintenance you want to handle. You deserve a clear, side‑by‑side look at what each option really means for your budget and lifestyle.

In this guide, you’ll compare condos, small multi‑families, and single‑family homes across Boston with practical cost factors, financing differences, and a decision checklist. You’ll also see how neighborhoods like the South End, Dorchester, and West Roxbury stack up. Let’s dive in.

Boston condo vs house: quick snapshot

Greater Boston single‑family values have climbed faster than condos in recent years, with single‑family medians reaching about $1 million in mid‑2025, while condos have been steadier around the mid‑$600k to $700k range. That gap shapes what you can buy and where you buy it. Recent coverage of the region’s milestone helps frame the market context.

South End condo snapshot

• What you get: Central location, strong walkability, and refined finishes in classic brownstones or boutique buildings.
• What it costs: Condos in premium South End pockets often command a per‑square‑foot premium. Smaller one‑bedrooms can price below larger renovated units.
• Tradeoffs: Limited private outdoor space and reliance on building management. HOA or common‑area expenses can be higher in older or amenity‑rich buildings.

Dorchester three‑decker snapshot

• What you get: More interior space per dollar and potential rental income from other units. The neighborhood has long been home to Boston’s iconic two‑ and three‑decker stock. Learn more about this housing type from the Dorchester Atheneum’s historical overview.
• What it costs: Median values in several Dorchester subareas are materially below central neighborhoods.
• Tradeoffs: Older systems and building envelopes can mean higher maintenance. Plan for inspections that address unit separations, mechanicals, and code compliance.

West Roxbury single‑family snapshot

• What you get: A more suburban feel within city limits, with yards and on‑site parking more common. Price‑per‑square‑foot is typically lower than central brownstones.
• What it costs: Recent reports placed median sales in the mid‑$700k to low‑$800k range, depending on timing and product.
• Tradeoffs: Longer commutes to central job hubs depending on your exact block. Fewer walkable amenities than core neighborhoods.

What your monthly cost really includes

Your budget decision is bigger than the purchase price. Build your monthly number with line‑item clarity:

• Mortgage principal and interest: Your lender will estimate this based on your rate and down payment.
• Property taxes: Boston applies the residential tax rate to assessed value and offers exemptions for eligible owner‑occupants. Use the city’s Assessing Department tools to review assessments and exemptions.
• Insurance: Condo owners typically carry an HO‑6 policy for interiors and personal property, while the building’s master policy covers common areas. Single‑family owners carry full dwelling coverage. See the condo vs homeowners insurance breakdown to align limits with your situation.
• HOA/condo fees: These vary widely. Metro Boston medians often land in the low‑to‑mid hundreds per month, while full‑service buildings can exceed $1,000. Get current budgets and minutes before you assume future costs. A quick primer on averages is available from this HOA fee overview.
• Maintenance reserve: For houses, simple rules of thumb are useful. Many owners budget about 1 percent of purchase price per year or about $1 per square foot, and older homes may need 2 to 4 percent for major systems over time. Condos shift big items to the association, but the tradeoff is potential special assessments if reserves are low. See common budgeting rules in this maintenance guide.
• Parking and storage: Budget for garage or off‑site parking if your condo does not include a spot. Street permit rules can change, so verify current policies with the City before you rely on them.

Tip: A $350 monthly HOA equals $4,200 per year. Add that to PITI when you compare a condo to a house at a similar price.

Financing and approval differences

Financing can tilt the decision, especially if you are open to a 2 to 4 unit home.

• Condos: Some programs require building eligibility and look at factors like owner‑occupancy, HOA delinquencies, and reserve funding. Governance and disclosure in Massachusetts are guided by Chapter 183A of the General Laws. Ask your lender about any project‑approval steps early.
• Small multi‑family (2–4 units): FHA allows qualified owner‑occupants to buy 2 to 4 unit properties with low down payments, and lenders often count a portion of projected rent from the other units when qualifying. Requirements and reserves vary by program, so review details before you shop. See a plain‑English overview of typical lender considerations for 2 to 4 units here.
• Single‑family: Usually the most straightforward to finance. The buyer pool at resale can also be broader, which can support liquidity over time. Regional data showing single‑family strength provides helpful context, as seen in recent Boston market coverage.

Lifestyle and commute tradeoffs

Transit access varies by neighborhood and even by block. Dorchester benefits from Red Line branches and frequent buses. The South End has quick access to Back Bay and commuter rail nodes. West Roxbury relies more on commuter rail, express buses, or driving. Boston‑area commute times often average around the low‑30 minutes mark, but your specific route matters. Explore the network using the MBTA system overview and test your door‑to‑door trip with a planner before you decide.

Resale and who buys it next

Every property has a likely next buyer. Single‑family homes with yards tend to appeal to a wide audience over time. Condos in walkable, amenity‑rich areas often sell quickly to urban‑minded buyers. Small multi‑families attract owner‑occupants and investors, which can be a narrower pool. There is no single guarantee, but market context showing single‑family strength in Greater Boston helps explain why many buyers choose that path for long‑term liquidity.

Pros, cons, and best fit

South End condo

• Best fit: You value location, design, and a lower‑maintenance lifestyle.
• Pros: Walkability, central access, often turnkey interiors, professional management.
• Cons: Higher per‑square‑foot pricing, HOA costs, limited private outdoor space.

Dorchester three‑decker

• Best fit: You want space and are open to managing tenants to offset costs.
• Pros: More square footage per dollar, potential rental income, long‑term wealth building through multi‑unit ownership.
• Cons: Older buildings can require higher maintenance. Lending and inspections are more complex than for single‑family.

West Roxbury single‑family

• Best fit: You prioritize private outdoor space, on‑site parking, and a quiet street feel.
• Pros: Yard and parking, simpler ownership, broad resale appeal.
• Cons: Longer commute to central job nodes for many addresses, fewer walkable amenities.

Quick decision checklist

Use this to compare a condo, a three‑decker, and a single‑family on equal footing.

Cost model for any property

• Price + down payment + estimated rate = principal and interest from your lender
• Taxes: Look up assessed value and exemptions with the City’s Assessing Department tools
• Insurance: Compare HO‑6 for condos vs full homeowners coverage for houses using this insurance comparison
• HOA/condo fees: Start with a realistic estimate based on typical HOA ranges
• Maintenance: Budget 1 percent of purchase price or $1 per square foot per year for houses, and review HOA reserves for condos using these budgeting rules
• Parking: Add monthly garage or off‑site costs if not included

If you are buying a condo

• Request: Current HOA budget and financials, the latest reserve study, master insurance declarations, 12 to 24 months of meeting minutes, owner‑occupancy and rental data, any pending or recent special assessments, management contract, bylaws and rules.
• Legal baseline: Read up on Massachusetts Chapter 183A for owner rights and association governance.
• Red flags: Low reserves, repeated special assessments, or minutes noting upcoming big‑ticket projects with no funding plan.

If you are buying a three‑decker (2–4 units)

• Inspection: Hire a multi‑unit‑savvy inspector to review unit separations, heating and electrical per unit, plumbing, roof, foundation, and permitting.
• Financing: Confirm down‑payment minimums and rent‑credit rules with your lender. See typical 2–4 unit program considerations here.
• Modeling: Underwrite conservatively. Include vacancy and a 30 to 50 percent operating expense ratio for older, owner‑managed buildings.

If you are buying a single‑family

• Maintenance: Use a stronger maintenance reserve for older homes.
• Insurance: Confirm full replacement cost with your carrier.
• Lead and older‑home hazards: For homes built before 1978, federal law requires lead‑paint disclosure and delivery of the EPA pamphlet. See the EPA’s notice on disclosure requirements here.

Example decision paths

• You want urban convenience and low maintenance: A South End condo keeps you close to transit and amenities. Budget realistically for HOA fees and confirm reserves to minimize special‑assessment risk.
• You want space and long‑term wealth building: A Dorchester three‑decker can pair larger living space with rental income potential. Plan for thorough inspections and a financing conversation early.
• You want a yard and simpler ownership: A West Roxbury single‑family offers private outdoor space and easier parking. Account for a longer commute and a larger personal maintenance reserve.

Ready to choose with clarity?

Whether you lean condo, three‑decker, or single‑family, the right answer balances your budget, your commute, and how you want to live day to day. If you want a clear, numbers‑forward comparison tailored to your goals, our boutique team pairs appraisal‑level valuation with neighbor‑by‑neighbor insight to help you buy with confidence. Start a conversation with Prism Real Estate Group to map your options and request a free market valuation.

FAQs

How do Boston condo fees affect my budget?

• Add the monthly HOA to your mortgage, taxes, and insurance. Typical metro ranges are in the low‑to‑mid hundreds per month, and full‑service buildings can exceed $1,000.

What should I review before buying a Boston condo?

• Request the HOA budget, reserve study, master insurance declarations, recent meeting minutes, owner‑occupancy data, bylaws, and documentation of any pending assessments.

Can I buy a Boston three‑decker with a low down payment?

• FHA allows many qualified owner‑occupants to buy 2–4 unit properties with a low down payment, and lenders may count a portion of projected rents when qualifying.

How do Boston property taxes work for homeowners?

• Taxes are applied to assessed value using the residential rate, with an exemption available to eligible owner‑occupants. Use the City’s Assessing tools to estimate your bill.

What insurance do I need for a condo vs a house in Boston?

• Condos typically need an HO‑6 policy for interior coverage plus the building’s master policy for common areas. Single‑family homes need full dwelling coverage.

What are commute differences among South End, Dorchester, and West Roxbury?

• South End offers central access to Back Bay and rail. Dorchester benefits from Red Line branches. West Roxbury relies more on commuter rail, express buses, or driving.