Is West Roxbury, Massachusetts Good for Airbnb Investment?

To start an Airbnb in West Roxbury, Massachusetts, begin by researching Boston's short-term rental regulations since West Roxbury falls under Boston jurisdiction, which requires hosts to register with the city, obtain a short-term rental license ($200-300 annually), and comply with zoning restrictions that limit rentals to owner-occupied properties or those in specific districts. Contact Boston's Inspectional Services Department to obtain necessary permits including a business certificate, occupancy permit, and ensure fire safety compliance with smoke detectors, carbon monoxide detectors, and emergency egress requirements. Find a suitable property in West Roxbury by searching residential areas near Centre Street, the VFW Parkway, or near Millennium Park, considering proximity to public transportation like the Needham Line commuter rail stations, and ensure the property meets Boston's requirement that short-term rentals cannot exceed 120 days annually unless it's your primary residence. Furnish the space with quality basics including comfortable bedding, kitchen essentials, WiFi, and local touches highlighting West Roxbury's suburban charm and proximity to downtown Boston. Create your listing on Airbnb and other platforms like VRBO, emphasizing the neighborhood's family-friendly atmosphere, easy access to Legacy Place shopping, and 20-minute commute to downtown Boston via public transit. Manage your property by maintaining consistent communication with guests, coordinating cleaning services, monitoring reviews, ensuring compliance with Boston's noise ordinances and parking regulations, and keeping detailed records for tax purposes while staying updated on any changes to Boston's evolving short-term rental regulations.

To identify profitable short-term rental properties in West Roxbury, Massachusetts, focus on locations within walking distance of the West Roxbury commuter rail station and near popular areas like Centre Street's restaurant district, as proximity to public transit connecting to downtown Boston significantly increases demand. Target single-family homes or condos with 2-3 bedrooms, dedicated parking spaces, and outdoor areas like patios or yards, as business travelers and families visiting nearby hospitals like VA Boston Healthcare System value these amenities. Conduct pricing analysis using AirDNA and Mashvisor to benchmark against similar properties in neighboring Jamaica Plain and Roslindale, aiming for properties that can generate $150-250 per night during peak seasons while maintaining 65-75% occupancy rates. Research competition by analyzing existing STR listings within a 2-mile radius, identifying gaps in amenities or pricing strategies, and monitor seasonal demand patterns driven by Boston's academic calendar and medical tourism. Utilize tools like Rabbu for market analysis, STR Helper for revenue projections, and connect with local real estate agents familiar with West Roxbury's zoning regulations, as the area's residential character and proximity to Boston's medical district create unique opportunities for investors who understand both local restrictions and guest preferences for quiet, family-friendly neighborhoods with easy city access.

To obtain an Airbnb/STR permit in West Roxbury, Massachusetts, you must apply through the City of Boston's Inspectional Services Department since West Roxbury is a neighborhood within Boston city limits. Submit your application online through the City of Boston's permitting portal or in person at 1010 Massachusetts Avenue, and provide required documents including a completed short-term rental registration form, proof of property ownership or lease agreement with landlord consent, certificate of occupancy, floor plans, proof of liability insurance (minimum $1 million), contact information for a local representative available 24/7, and payment of the $200 annual registration fee plus a $25 processing fee. Boston requires STR operators to limit rentals to no more than 120 nights per year for non-owner occupied units, maintain guest registries, post emergency contact information, ensure compliance with zoning laws, and obtain necessary inspections for fire safety and building code compliance. The approval timeline typically takes 4-6 weeks after submission of complete documentation, and permits must be renewed annually with updated insurance certificates and compliance documentation, while operators must also register with the Massachusetts Department of Revenue for state tax purposes and may need additional permits if the property is in a historic district or requires zoning variances.

Short-term rentals (STRs) are legal in West Roxbury, Massachusetts, but operate under Boston's comprehensive STR regulations implemented in 2019. The city requires all STR operators to obtain a license, pay registration fees, and comply with safety requirements including smoke and carbon monoxide detectors. STRs are permitted in residential zones but face restrictions including a cap on the total number of licenses citywide (approximately 1,400), limits on the number of guests, and requirements for owner occupancy in multi-unit buildings. Properties must be the owner's primary residence if operating year-round, though investment properties can operate as STRs for up to 120 days annually. The regulations also mandate good neighbor agreements, parking provisions, and compliance with zoning laws. Boston's STR ordinance applies uniformly across all neighborhoods including West Roxbury, with enforcement handled through the city's Inspectional Services Department, and violations can result in fines up to $300 per day.

The best areas for Airbnb investment in West Roxbury, Massachusetts include the neighborhoods near the Dedham Line and VFW Parkway corridor, particularly around the West Roxbury Center and Bellevue Hill areas. The West Roxbury Center district is attractive due to its proximity to the commuter rail station providing direct access to downtown Boston, making it ideal for business travelers and tourists wanting affordable alternatives to downtown hotels while maintaining easy transit access. The Bellevue Hill and Parkway area offers appeal to families and groups visiting the Arnold Arboretum (adjacent in Jamaica Plain), one of Boston's premier attractions, as well as those attending events at nearby venues like the West Roxbury Educational Complex. The Spring Street and Centre Street corridors are particularly valuable due to their walkable access to local restaurants, shops, and services, plus proximity to Legacy Place shopping center in Dedham, attracting visitors for retail tourism. Properties near the Millennium Park area benefit from guests visiting for youth sports tournaments and events, while the residential streets between VFW Parkway and Centre Street offer quiet, family-friendly accommodations for visitors to Boston who prefer suburban settings with parking availability and lower costs than downtown options.

Airbnb properties in West Roxbury, Massachusetts are subject to multiple lodging taxes including the Massachusetts state room occupancy excise tax of 5.7%, the Boston local room occupancy excise tax of 6.5%, and the Boston short-term rental tax of 3%, resulting in a combined tax rate of approximately 15.2% on rental income. 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 ensuring compliance. The Massachusetts Department of Revenue requires operators to register for a room occupancy excise tax account and file monthly returns by the 20th of the following month, while the City of Boston requires registration for short-term rental operations and separate monthly filings for local taxes. Exemptions may apply for stays exceeding 90 consecutive days, rentals to the same occupant for more than 30 days, or properties rented fewer than 14 days per year, though specific exemption criteria can vary between state and local jurisdictions and hosts should verify current requirements with both the Massachusetts Department of Revenue and Boston's Office of Consumer Affairs and Licensing.

The total cost to start an Airbnb in West Roxbury, 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 to create an attractive rental space. Initial setup costs including professional photography, listing creation, and basic renovations total $3,000-$5,000. Permits and fees include a $300 short-term rental license from Boston, potential $500-$1,000 in legal/administrative costs, and any required safety inspections costing $200-$500. Insurance premiums for short-term rental coverage run $2,000-$3,500 annually, with the first year paid upfront. Utility deposits and connections for electricity, gas, water, internet, and cable cost approximately $1,000-$1,500. First six months of operating costs including utilities ($200/month), cleaning services ($100-150 per turnover), maintenance reserves ($300/month), property management software ($50/month), and marketing expenses total approximately $4,500-$6,000, bringing the complete startup investment to the $650,000-$750,000 range.

Airbnb properties in West Roxbury, Massachusetts typically generate annual revenues between $25,000-$45,000 for entire home listings, with average daily rates ranging from $85-$140 depending on property size and amenities. Operating expenses generally consume 40-60% of gross revenue, including cleaning fees ($30-50 per turnover), utilities ($150-250 monthly), property management (10-20% of revenue), insurance ($1,200-2,000 annually), and maintenance costs ($2,000-4,000 yearly). Profit margins typically range from 15-35% after expenses, with successful properties achieving higher margins through strategic pricing, professional photography, and consistent 4.8+ star ratings. Properties within walking distance of the West Roxbury commuter rail station or near Millennium Park command premium rates, with some three-bedroom homes generating $50,000+ annually. Success factors include maintaining occupancy rates above 65%, implementing dynamic pricing strategies, providing local guidebooks, and ensuring rapid response times to guest inquiries. A typical two-bedroom property purchased for $450,000 in 2022 with a $2,800 monthly mortgage can achieve positive cash flow of $800-1,500 monthly during peak seasons (May-October), though winter months often see reduced demand and occupancy rates dropping to 40-50%.

Airbnb investments in West Roxbury, 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 achieve gross rental yields of 4-6% annually through short-term rentals, with net returns after expenses (property management, utilities, maintenance, insurance) settling at the 8-12% range. Cash-on-cash returns vary significantly based on down payment amounts, but investors putting down 20-25% can expect 6-10% returns on their actual cash invested. Most West Roxbury Airbnb investments reach profitability within 12-18 months, factoring in initial setup costs, furnishing, and marketing expenses. The neighborhood's proximity to downtown Boston, Longwood Medical Area, and major universities drives consistent demand, particularly from business travelers and medical professionals, supporting occupancy rates of 65-75% annually. Properties near the West Roxbury Center or with easy T access command premium rates of $120-180 per night, while typical single-family homes or condos average $90-140 nightly, contributing to these ROI projections in the current Massachusetts short-term rental market.

STRSearch is a national platform that specializes in identifying profitable short-term rental investment properties across markets including West Roxbury, Massachusetts. Local real estate agents in the area who focus on investment properties include Coldwell Banker Realty agents specializing in multi-family and investment properties, RE/MAX agents with short-term rental expertise, and Keller Williams agents who understand the Airbnb market dynamics in the Greater Boston area. National services that help investors include Awning (property management and investment analysis), Mashvisor (real estate analytics platform), AirDNA (short-term rental data and market analysis), Roofstock (turnkey rental property marketplace), and BiggerPockets (real estate investment community and resources). Local Boston-area companies such as RedfinNow, Boston Real Estate Investors Association members, and specialized investment property brokers at firms like Berkshire Hathaway HomeServices Commonwealth Real Estate also provide services for Airbnb investors. Additional services include STR property management companies like AvantStay, rental arbitrage specialists, and local property scouts who identify off-market opportunities in West Roxbury's residential neighborhoods near public transportation and Boston attractions.