Is Roslindale, Massachusetts Good for Airbnb Investment?

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 ($200-300 annually), and comply with zoning restrictions that typically limit rentals to owner-occupied properties or buildings with fewer than four units. 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 $400,000-600,000 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 ($80-150 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, while keeping detailed records for tax purposes and ensuring compliance with Massachusetts lodging taxes of 5.7% plus local option taxes.

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. Target 2-3 bedroom single-family homes or condos built after 1950 with parking spaces, modern kitchens, and outdoor space, as these features command premium rates of $150-250 per night in the area. Analyze comparable properties on Airbnb and VRBO within a 0.5-mile radius, noting that successful listings typically achieve 65-75% occupancy rates with average daily rates 20-30% 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" to understand neighborhood dynamics and seasonal demand patterns driven by nearby Arnold Arboretum visitors and Boston medical professionals seeking temporary housing.

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. 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), and contact information for a local representative if you're not local. The registration fee is approximately $200-300 annually, with additional inspection fees of around $300-500. 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 4-8 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.

Short-term rentals (STRs) are legal in Roslindale, Massachusetts, but operate under Boston's comprehensive STR regulations implemented in 2019. 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, though community concerns about housing availability and neighborhood character continue to influence policy discussions at the city level.

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. 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 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, resulting in a combined tax rate of approximately 15.2% for short-term rentals. 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, though hosts remain ultimately responsible for compliance and may need to register with the Massachusetts Department of Revenue and Boston's Treasury Department. 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.

The total cost to start an Airbnb in Roslindale, Massachusetts is approximately $650,000-$750,000. Property purchase costs around $550,000-$650,000 based on median home prices in the area as of 2023-2024. Furnishing a 2-3 bedroom property requires $15,000-$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-$3,500. Boston requires short-term rental registration at $200 annually plus potential zoning compliance fees of $500-$1,000. Insurance specifically for short-term rentals costs $2,000-$3,000 annually. Utility setup and deposits for electricity, gas, water, internet, and cable average $500-$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-$10,000 to initial capital requirements.

Airbnb properties in Roslindale, Massachusetts typically generate annual revenues between $18,000-$35,000 for entire homes and $8,000-$15,000 for private rooms, based on average daily rates of $85-$140 and occupancy rates of 45-65%. Operating expenses generally consume 40-55% of gross revenue, including cleaning fees ($25-$40 per turnover), utilities ($150-$250 monthly), property management (10-20% of revenue), insurance ($800-$1,500 annually), and maintenance costs averaging $2,000-$4,000 yearly. Net profit margins typically range from 25-40% for well-managed properties, with successful hosts in the neighborhood earning $8,000-$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 10-15% below Jamaica Plain rates, professional photography, consistent 4.8+ star ratings, and targeting the growing demand from visitors to nearby Arnold Arboretum and patients accessing Brigham and Women's Hospital. 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.

Airbnb investments in Roslindale, Massachusetts typically generate annual ROI of 8-12% with cash-on-cash returns ranging from 6-10% based on current market conditions. Properties in this Boston neighborhood, with median home prices around $650,000-$750,000, can expect gross rental yields of 4-6% annually when operated as short-term rentals. Initial investment requirements including down payment, renovations, and furnishing typically range from $150,000-$200,000 for a typical 2-3 bedroom property. Most investors achieve profitability within 18-24 months, with average daily rates of $120-$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 65-75% annually. Cash flow typically becomes positive within 12-18 months after accounting for mortgage payments, property management fees, cleaning costs, and maintenance expenses.

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