Is Roslindale, Massachusetts Good for Airbnb Investment?

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Roslindale, Massachusetts market research

Roslindale, Massachusetts Airbnb Investment Overview

$1,200–$2,800Typical monthly host earnings
8–12%Typical annual ROI
65–70%Average annual occupancy
VariesCombined taxes and local fees
Investment

Is Airbnb a Good Investment in Roslindale, Massachusetts?

Potentially—Roslindale, Massachusetts combines visitor demand with long-term real estate upside.

  • Presents a compelling opportunity within Boston's dynamic real estate market.
  • Current market conditions in Roslindale show a stable and appreciating property landscape, driven by its family-friendly atmosphere, diverse community.
  • While tourism trends directly within Roslindale are more localized, the neighborhood benefits significantly from Boston's overall robust tourism sector, attracting visitors for its historical sites, universities.
  • This spillover demand from Boston proper, combined with Roslindale's charming village center and green spaces like the Arnold Arboretum.
  • Property values in Roslindale, while higher than national averages, offer strong long-term investment potential due to ongoing development and desirability within the greater Boston area.
  • The investment potential is further enhanced by the opportunity to cater to both tourists seeking a quieter, more residential experience close to city amenities.
Earnings

How Much Does an Average Airbnb Earn in Roslindale?

$1,200–$2,800 per month based on location, season, and property quality.

  • Based on available market data and rental analytics, Airbnb hosts in Roslindale, Massachusetts typically earn between $1,200 to $2,800 per month.
  • Seasonal variations show peak earnings during summer months and fall foliage season, with revenues increasing by 25-40% above winter baseline rates.
  • Key factors influencing earnings include proximity to public transportation (particularly the Commuter Rail station), property size and amenities, professional photography quality, competitive pricing strategies.
  • Properties within a 10-minute walk of Forest Hills Station command premium rates due to easy access to downtown Boston, while listings featuring parking, modern kitchens.
  • Revenue optimization depends heavily on dynamic pricing tools, maintaining superhost status, and capitalizing on Boston's major events and conventions that drive demand spillover to surrounding neighborhoods like Roslindale.
ROI Analysis

Airbnb Return on Investment in Roslindale

Potentially strong—typical annual ROI is 8–12%.

  • Typically generate ROI between 8-12% annually, with payback periods ranging from 7-10 years depending on property acquisition costs and renovation expenses.
  • The average daily rate for Airbnb properties in Roslindale ranges from $85-120, with occupancy rates averaging 65-75% throughout the year.
  • Compared to traditional long-term rentals in the area, which typically yield 6-8% ROI with average monthly rents of $1,400-1,900 for similar properties.
  • The higher ROI potential comes with increased vacancy risk, regulatory considerations, and substantially more time investment for property management.
Occupancy Rate

Average Airbnb Occupancy Rate in Roslindale

Roslindale, Massachusetts averages 65–70% annual occupancy, with seasonal variation.

  • Airbnb occupancy rates in Roslindale, Massachusetts typically average around 65-70% annually, with significant seasonal variation that peaks during summer months (July-September) at approximately 80-85% occupancy due to Boston's tourism season, university activities, and favorable weather conditions.
  • Winter months (December-February) see the lowest occupancy rates at around 45-55%, while spring and fall maintain moderate levels of 60-70%.
  • Peak demand occurs during Boston Marathon week in April, summer tourist season, and September when colleges resume, driving rates above the annual average.
  • Roslindale's occupancy rates generally align closely with greater Boston area averages but run slightly below Massachusetts state averages of 72-75% due to its residential nature and distance from primary tourist attractions, though they exceed national Airbnb averages of approximately 60-65% because of the strong Boston metropolitan market demand and limited hotel inventory in the area.
Best Neighborhoods

Best Neighborhoods for Airbnb in Roslindale

The strongest opportunities balance visitor demand, nightly rates, and acquisition cost.

  • The best Airbnb investment neighborhoods in Roslindale include the Village Main area near Roslindale Square, which offers excellent walkability to restaurants, shops.
  • The Washington Street corridor presents strong investment potential due to its diverse dining scene, proximity to the Arboretum, and appeal to visitors interested in Boston's multicultural communities.
  • The area near Healy Field and the Roslindale Community Center attracts families and sports enthusiasts.
  • The neighborhoods bordering Jamaica Plain benefit from spillover demand when JP properties are booked, particularly appealing to younger demographics seeking trendy.
  • The residential streets near Belgrade Avenue offer quiet, family-friendly environments that appeal to longer-term stays and visiting academics or medical professionals working at nearby institutions.
  • Properties near the Forest Hills T-station area capture transit-oriented demand from guests wanting easy subway access while staying in a more residential.
  • The Archdale area provides a sweet spot of suburban tranquility with urban accessibility, attracting visitors seeking authentic Boston neighborhood living experiences while maintaining reasonable property acquisition costs and strong rental yields due to the area's growing reputation among savvy travelers.
Regulations

Short-term Rental Regulations in Roslindale

Yes, but only where zoning permits short-term rentals and every required license is current.

  • Short-term rental regulations in Roslindale, Massachusetts are governed by Boston's citywide ordinance implemented in 2019, which requires all short-term rental operators to obtain a license from the city's Inspectional Services Department and register with the state.
  • Occupancy is restricted to two guests per bedroom plus two additional guests, with a maximum of six guests total regardless of property size.
  • All units must pass annual inspections covering fire safety, building codes, and sanitation requirements, and operators must maintain liability insurance of at least $1 million.
  • The registration process involves submitting floor plans, proof of insurance, owner occupancy documentation, and paying annual fees of approximately $200-300.
  • Zoning restrictions prohibit short-term rentals in certain residential districts, and the city has implemented a cap on the total number of licenses issued.
  • Recent changes in 2022 included stricter enforcement mechanisms, increased penalties for violations up to $1,000 per day, and enhanced neighbor notification requirements.
Fees and Taxes

Short-term Rental Fees and Taxes in Roslindale

Tax rates vary by jurisdiction; licensing, inspection, and insurance costs are additional.

  • Short-term rentals in Roslindale, Massachusetts are subject to several fees and taxes including the state lodging tax of 5.7% on all bookings.
  • Property owners must obtain an annual short-term rental registration permit from the City of Boston costing approximately $200-300 per year.
  • Additional requirements include a $25 annual inspection fee, potential fire department inspection fees of $100-150, and operators may need to pay quarterly estimated taxes on rental income to both state and federal authorities.
  • Properties must also maintain liability insurance with minimum coverage requirements, typically costing $500-1,500 annually depending on coverage levels.
Common questions

Roslindale, Massachusetts Airbnb investment FAQs

How to start an Airbnb in Roslindale, Massachusetts?

To start an Airbnb in Roslindale, Massachusetts, begin by researching Boston's short term rental regulations, which require hosts to register with the city, obtain a short term rental license ($200 to 300 annually).

Launch checklist

  • Contact Boston's Inspectional Services Department to obtain necessary permits including a Certificate of Occupancy and ensure compliance with fire safety codes, which may require smoke detectors, carbon monoxide detectors, and emergency egress plans.
  • Find a suitable property in Roslindale's residential neighborhoods, considering proximity to the Orange Line T stops like Forest Hills or Roslindale Village for guest convenience, with typical property costs ranging $400,000 to 600,000 for single family homes.
  • Furnish the space with essential amenities including Wi Fi, linens, kitchen supplies, and local guidebooks highlighting nearby attractions like Arnold Arboretum and local restaurants along Centre Street.
  • Create your listing on Airbnb and VRBO platforms with professional photos, competitive pricing ($80 to 150 per night depending on size and season), and detailed descriptions emphasizing Roslindale's diverse community and easy access to downtown Boston.
  • Manage your property by establishing check in procedures, maintaining cleanliness standards, responding promptly to guest inquiries, and potentially hiring local cleaning services or property management companies like RedAwning or Vacasa if needed.
What's the best way to identify good STR properties in Roslindale, Massachusetts?

To identify profitable short term rental properties in Roslindale, Massachusetts, focus on properties within walking distance of the Forest Hills T station and Roslindale Village, as these areas offer excellent public transit access to downtown Boston and local amenities.

What to prioritize

  • Target 2 to 3 bedroom single family homes or condos built after 1950 with parking spaces, modern kitchens, and outdoor space, as these features command premium rates of $150 to 250 per night in the area.
  • Analyze comparable properties on Airbnb and VRBO within a 0.5 mile radius, noting that successful listings typically achieve 65 to 75% occupancy rates with average daily rates 20 to 30% higher than traditional rentals.
  • Research competition by monitoring active STR listings in zip codes 02131 and nearby Jamaica Plain (02130) to identify gaps in amenities or pricing.
  • Utilize AirDNA for market data specific to Roslindale, Mashvisor for investment analysis, and the City of Boston's short term rental registration requirements, while leveraging local Facebook groups like "Roslindale Moms" and "Roslindale Neighbors".
How to get an Airbnb permit in Roslindale, Massachusetts?

To obtain an Airbnb/STR permit in Roslindale, Massachusetts, you must first register with the City of Boston's Inspectional Services Department since Roslindale is a neighborhood within Boston city limits.

Documents and approvals

  • Begin by visiting the Boston.gov website and navigating to the short term rental registration section, or visit the Inspectional Services Department at 1010 Massachusetts Avenue.
  • Required documents include a completed short term rental registration form, proof of property ownership or lease agreement with landlord consent, certificate of occupancy, floor plan showing maximum occupancy, proof of liability insurance ($1 million minimum).
  • The registration fee is approximately $200 to 300 annually, with additional inspection fees of around $300 to 500.
  • You must also obtain a business certificate from the City Clerk's office ($65 fee) and register with the Massachusetts Department of Revenue for tax collection purposes.
  • Boston requires STRs to be owner occupied or in owner occupied buildings with 3 or fewer units, maintain maximum occupancy limits based on square footage, provide 24/7 contact information to neighbors, and comply with noise ordinances and parking restrictions.
  • The timeline typically takes 4 to 8 weeks from application submission to approval, depending on inspection scheduling and document completeness.
  • Properties must pass a housing inspection before approval, and hosts must collect and remit local occupancy taxes of 6.5% plus state taxes.
Is it legal to operate a short-term rental in Roslindale, Massachusetts?

Short term rentals (STRs) are legal in Roslindale, Massachusetts, but operate under Boston's comprehensive STR regulations implemented in 2019.

Core operating requirements

  • The city requires all STR operators to obtain a license, with different rules for owner occupied versus non owner occupied properties owner occupied units can rent up to 3 bedrooms while non owner occupied properties face stricter limitations and higher fees.
  • All STRs must comply with safety requirements including smoke and carbon monoxide detectors, fire extinguishers, and emergency egress plans, while operators must pay a 6.5% city excise tax plus state and local occupancy taxes.
  • Boston caps the total number of non owner occupied STR licenses citywide and prohibits STRs in certain affordable housing units and rent stabilized properties.
  • Recent enforcement has increased since 2020, with the city actively monitoring platforms like Airbnb and VRBO for compliance, and violations can result in fines up to $300 per day.
  • Roslindale, being a residential neighborhood within Boston, follows these same citywide regulations without additional neighborhood specific restrictions.
What are the best places to invest in Airbnb in Roslindale, Massachusetts?

The best areas for Airbnb investment in Roslindale, Massachusetts include the Village Main Street corridor near Washington Street and South Street, which offers walkability to local restaurants, cafes, and the weekly farmers market, attracting visitors seeking an authentic Boston neighborhood experience. The area near Roslindale Square is particularly attractive due to its proximity to the MBTA Orange Line at Forest Hills station, providing easy access to downtown Boston for business travelers and tourists visiting major attractions like Fenway Park, the Freedom Trail, and Harvard University.

Areas to research

  • The residential streets around Belgrade Avenue and Centre Street are ideal for families and groups visiting Boston Children's Hospital, which is only 15 minutes away, as well as visitors to nearby Franklin Park Zoo and the Arnold Arboretum.
  • Properties near the Roslindale West Roxbury border benefit from proximity to both the bustling Centre Street West Roxbury commercial district and easy highway access via Route 1, making them attractive to medical professionals visiting Brigham and Women's Hospital and other Longwood Medical Area facilities, as well as visitors attending events at Boston College or exploring the Emerald Necklace park system.
Airbnb and lodging taxes in Roslindale, Massachusetts

Airbnb properties in Roslindale, Massachusetts are subject to multiple lodging taxes including the Massachusetts state room occupancy excise tax of 5.7%, Boston's local room occupancy excise tax of 6.5%, and Boston's short term rental tax of 3% specifically for stays under 31 days. These taxes are typically collected by Airbnb directly from guests at the time of booking and remitted to the appropriate tax authorities on behalf of hosts.

Taxes and filing responsibilities

  • The state tax applies to all stays regardless of duration, while Boston's short term rental tax only applies to rentals of less than 31 consecutive days, and there are generally no exemptions for small operators or occasional rentals.
  • Hosts must maintain detailed records of all bookings and tax collections, and may be required to file periodic returns even when Airbnb handles collection, with penalties applying for non compliance including potential fines and interest on unpaid taxes.
Total cost to purchase, furnish and operate an Airbnb in Roslindale, Massachusetts

The total cost to start an Airbnb in Roslindale, Massachusetts is approximately $650,000 to $750,000.

Cost breakdown

  • Property purchase costs around $550,000 to $650,000 based on median home prices in the area as of 2023 to 2024.
  • Furnishing a 2 to 3 bedroom property requires $15,000 to $25,000 for quality furniture, bedding, kitchenware, and decor suitable for short term rentals.
  • Initial setup costs including professional photography, listing creation, smart locks, and welcome materials total $2,000 to $3,500.
  • Boston requires short term rental registration at $200 annually plus potential zoning compliance fees of $500 to $1,000.
  • Insurance specifically for short term rentals costs $2,000 to $3,000 annually.
  • Utility setup and deposits for electricity, gas, water, internet, and cable average $500 to $800 initially.
  • First six months operating costs including utilities ($1,200), cleaning services ($2,400), supplies and maintenance ($1,500), platform fees to Airbnb and VRBO ($3,000 estimated), property management software ($300), and marketing ($500) total approximately $8,900.
  • Additional considerations include potential HOA fees, property taxes, and emergency repair funds which could add $5,000 to $10,000 to initial capital requirements.
Are Airbnb properties in Roslindale, Massachusetts profitable?

Airbnb properties in Roslindale, Massachusetts typically generate annual revenues between $18,000 to $35,000 for entire homes and $8,000 to $15,000 for private rooms, based on average daily rates of $85 to $140 and occupancy rates of 45 to 65%.

Profitability indicators

  • Operating expenses generally consume 40 to 55% of gross revenue, including cleaning fees ($25 to $40 per turnover), utilities ($150 to $250 monthly), property management (10 to 20% of revenue), insurance ($800 to $1,500 annually).
  • Net profit margins typically range from 25 to 40% for well managed properties, with successful hosts in the neighborhood earning $8,000 to $18,000 annually after expenses.
  • Key success factors include proximity to public transportation (particularly the Commuter Rail and bus lines to downtown Boston), competitive pricing 10 to 15% below Jamaica Plain rates, professional photography, consistent 4.8+ star ratings.
  • Properties within walking distance of Roslindale Village's restaurants and shops command premium rates, while three bedroom homes near the Arboretum have shown particularly strong performance with average occupancy rates exceeding 60% and daily rates reaching $160 during peak foliage season.
What is the expected return on investment for an Airbnb in Roslindale, Massachusetts?

Airbnb investments in Roslindale, Massachusetts typically generate annual ROI of 8 to 12% with cash on cash returns ranging from 6 to 10% based on current market conditions.

Return planning figures

  • Properties in this Boston neighborhood, with median home prices around $650,000 to $750,000, can expect gross rental yields of 4 to 6% annually when operated as short term rentals.
  • Initial investment requirements including down payment, renovations, and furnishing typically range from $150,000 to $200,000 for a typical 2 to 3 bedroom property.
  • Most investors achieve profitability within 18 to 24 months, with average daily rates of $120 to $180 depending on property size and amenities.
  • The proximity to downtown Boston via the Orange Line and growing popularity of the neighborhood among visitors seeking authentic local experiences supports occupancy rates of 65 to 75% annually.
  • Cash flow typically becomes positive within 12 to 18 months after accounting for mortgage payments, property management fees, cleaning costs, and maintenance expenses.
What company can help me find and buy a profitable Airbnb in Roslindale, Massachusetts?

STRSearch is a national platform that helps investors identify profitable short term rental properties across markets including Roslindale, Massachusetts.

Companies and resources

  • Local real estate agents specializing in investment properties in the Roslindale area include Coldwell Banker Realty agents, RE/MAX agents, and Keller Williams professionals who focus on multi family and investment properties in Boston's neighborhoods.
  • National services like Awning (formerly RedAwning) provide full service Airbnb property management and investment guidance, while Mashvisor offers market analysis tools for short term rental investments in the Boston metro area.
  • Local Boston based investment firms such as Boston Real Estate Investment Group and New England Real Estate Network often work with investors seeking Airbnb properties in emerging neighborhoods like Roslindale.
  • Additional national platforms include BiggerPockets for networking with local investors, AirDNA for market data analysis, and Roofstock which occasionally features Boston area rental properties suitable for short term rental conversion.

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Success Rate
100% profitable track record
Data Accuracy
Proprietary filters, precise forecasts
Service Scope
End-to-end STR investment support
Risk Mitigation
Only cash-flow-positive matches
Expert Network
Vetted realtors, lenders, designers included
Other Services
Success Rate
Inconsistent ROI, no guarantees
Data Accuracy
Generic metrics, inaccurate estimates
Service Scope
Partial services only
Risk Mitigation
No profitability screening
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