Is Roxbury, Massachusetts Good for Airbnb Investment?

To start an Airbnb in Roxbury, Massachusetts, begin by researching Boston's short-term rental regulations since 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 buildings with 4+ units in certain areas. Contact Boston's Inspectional Services Department to verify your property meets fire safety codes, obtain necessary permits, and ensure compliance with the 120-day annual rental limit for non-owner occupied units. Find a suitable property in Roxbury by working with local real estate agents familiar with multi-family homes or condos, focusing on areas near public transportation like the Orange Line stations (Roxbury Crossing, Jackson Square) which are popular with visitors. Furnish the space with essential amenities including Wi-Fi, basic kitchen supplies, linens, and safety equipment like smoke detectors and carbon monoxide alarms as required by Boston fire codes. Create your Airbnb listing with professional photos highlighting proximity to downtown Boston (10-15 minutes), local attractions like the Museum of Fine Arts, and neighborhood character, pricing competitively around $80-150 per night based on 2023-2024 market rates. Manage your property by establishing cleaning protocols between guests, maintaining responsive communication, coordinating key exchanges or installing smart locks, and keeping detailed records for tax purposes while monitoring Boston's evolving short-term rental policies and community impact requirements.

To identify profitable short-term rental properties in Roxbury, Massachusetts, focus on locations within walking distance of public transportation like the Orange Line stations (Roxbury Crossing, Jackson Square) and areas near Boston Medical Center, as these attract business travelers and medical professionals. Target properties built after 1900 with 2-3 bedrooms, updated kitchens and bathrooms, parking availability, and strong WiFi infrastructure, as Roxbury's historic brownstones and triple-deckers are particularly appealing to guests seeking authentic Boston experiences. Conduct pricing analysis using AirDNA and Mashvisor to benchmark against similar properties in neighboring Jamaica Plain and South End, aiming for nightly rates between $80-150 depending on size and amenities, while analyzing seasonal demand patterns around Northeastern University and Boston University academic calendars. Research competition by monitoring active Airbnb and VRBO listings within a 0.5-mile radius, identifying gaps in amenities or property types, and studying guest reviews to understand common complaints and desired features. Utilize tools like Rabbu for Boston-specific STR regulations compliance, the City of Boston's property assessment database for purchase price analysis, and partner with local property management companies familiar with Roxbury's ongoing gentrification trends and the area's transformation from an emerging neighborhood to a more established rental market, while ensuring compliance with Boston's short-term rental registration requirements and owner-occupancy rules.

To obtain an Airbnb/STR permit in Roxbury, Massachusetts, you must apply through the City of Boston's Inspectional Services Department since Roxbury is a neighborhood within Boston city limits. Begin by submitting an application online through the City of Boston's official website or in person at 1010 Massachusetts Avenue, and include required documents such as 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), and a signed affidavit confirming compliance with zoning laws. The application fee is typically $200-300 annually, with additional inspection fees of approximately $100-150. You must also obtain a business certificate from the City Clerk's office if operating as a business entity, ensure the property meets all building and fire safety codes, install smoke and carbon monoxide detectors in all required areas, and comply with Boston's short-term rental regulations including maximum occupancy limits and quiet hours. The approval timeline generally takes 4-8 weeks depending on inspection scheduling and document completeness, and you may need to attend a hearing if there are neighborhood objections. Once approved, you must display your permit number in all online listings and renew annually while maintaining compliance with ongoing reporting requirements and tax obligations to both the city and state.

Short-term rentals (STRs) are legal in Roxbury, Massachusetts, but operate under Boston's comprehensive STR regulations established in 2019. The city requires all STR operators to obtain a license, pay annual fees, and comply with safety requirements including smoke and carbon monoxide detectors. STRs are permitted in residential zones but face restrictions including a 120-day annual cap for non-owner-occupied properties, while owner-occupied units can operate year-round. Boston prohibits STRs in certain affordable housing units and requires operators to register with the state, collect occupancy taxes, and maintain liability insurance. Recent enforcement has increased since 2020, with the city actively monitoring compliance through platforms like Airbnb and Vrbo, and violations can result in fines up to $300 per day. Roxbury, as part of Boston, follows these citywide regulations without additional neighborhood-specific restrictions, though community concerns about housing displacement have led to ongoing discussions about potential future limitations in gentrifying areas.

The best areas for Airbnb investment in Roxbury, Massachusetts include Fort Hill, which offers historic charm and proximity to downtown Boston attractions like the Freedom Trail and financial district, making it attractive for both tourists and business travelers. Dudley Square serves as a cultural hub with the Bruce C. Bolling Municipal Building and emerging arts scene, drawing visitors interested in Boston's diverse neighborhoods while being well-connected via public transit. The Roxbury Crossing area near Northeastern University and the Longwood Medical Area attracts medical professionals, researchers, and university visitors, providing steady demand from the healthcare and education sectors. Highland Park offers a more residential feel with Victorian architecture while maintaining easy access to downtown Boston, appealing to travelers seeking authentic neighborhood experiences. Jackson Square benefits from its Orange Line connectivity and ongoing gentrification, positioning it well for future growth as Boston's rental market expands, particularly attracting young professionals and tourists who want affordable alternatives to downtown accommodations while remaining within 15 minutes of major attractions.

Airbnb properties in Roxbury, Massachusetts are subject to multiple lodging taxes including the Massachusetts state room occupancy excise tax of 5.7% and the local option room occupancy excise tax imposed by the City of Boston at 6.5%, for a combined rate of 12.2% on short-term rental stays. These taxes apply to rentals of 31 days or less and are collected by platforms like Airbnb directly from guests at the time of booking, with the platform then remitting payments to the Massachusetts Department of Revenue on a monthly basis by the 20th of the following month. Host operators must register with the state and obtain a room occupancy tax registration certificate, and while platforms handle most collection and remittance, hosts remain ultimately responsible for ensuring proper tax compliance. Exemptions include stays of 32 days or longer, rentals to permanent residents lasting 90+ consecutive days, and accommodations provided to certain government employees or during declared emergencies, though standard vacation and business travelers do not qualify for exemptions.

The total cost to start an Airbnb in Roxbury, Massachusetts is approximately $520,000-$580,000. Property purchase costs around $450,000 based on median home prices in the area as of 2023. 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 amenities total $2,000-$3,000. Boston requires short-term rental registration and permits costing approximately $300-$500 annually, plus potential zoning compliance fees of $1,000-$2,000. Insurance for short-term rentals runs $2,000-$3,000 annually, significantly higher than standard homeowner's insurance. Utility setup and deposits for electricity, gas, water, internet, and cable total $1,500-$2,500. First six months of operating costs including utilities ($1,800), cleaning services ($3,600), supplies and maintenance ($1,200), platform fees to Airbnb and VRBO ($2,400 assuming 60% occupancy), property management software ($300), and marketing expenses ($500) total approximately $9,800. Additional considerations include potential HOA fees, property taxes, and a 3-6 month cash reserve for vacancies and unexpected repairs.

Airbnb properties in Roxbury, Massachusetts typically generate annual revenues between $18,000-$35,000 for entire homes and $8,000-$15,000 for private rooms, with average daily rates ranging from $65-$120 depending on property type and proximity to downtown Boston. Operating expenses generally consume 40-60% 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 ($2,000-$4,000 yearly). Net profit margins typically range from 15-35% for well-managed properties, with higher margins achieved through strategic pricing during peak periods like Boston Marathon week, college move-in seasons, and summer months when demand from tourists visiting nearby attractions increases. Success factors include maintaining high cleanliness standards, responding quickly to guest inquiries, optimizing listings with professional photography, and leveraging Roxbury's growing reputation as an emerging neighborhood with easy access to downtown Boston via public transit. Properties within walking distance of Jackson Square or Roxbury Crossing Orange Line stations command premium rates, while those offering parking spaces can increase occupancy rates by 15-20%. The neighborhood's ongoing gentrification and proximity to major hospitals and universities like Northeastern University create consistent demand, though hosts must navigate Boston's short-term rental regulations including registration requirements and occupancy limits that can impact profitability.

Airbnb investments in 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 gentrifying areas near downtown Boston command average daily rates of $85-120, with occupancy rates of 65-75% annually. Initial investment costs average $350,000-500,000 for suitable multi-family properties, requiring $70,000-150,000 down payments. Monthly gross revenues typically range $2,800-4,200 per unit after accounting for Airbnb fees, cleaning costs, and vacancy periods. Net operating income after expenses including utilities, maintenance, insurance, and property management averages $1,800-2,800 monthly per unit. Most investors achieve break-even within 18-24 months and full profitability by year 3, with properties near Roxbury Crossing and Highland Park showing stronger performance due to proximity to Orange Line transit access. Market appreciation in Roxbury has averaged 4-6% annually since 2020, contributing to total returns of 12-18% when combining rental income and property value increases.

STRSearch is a national platform that specializes in identifying profitable short-term rental investment properties and provides market analysis for Airbnb investments in Roxbury, Massachusetts. Local Boston-area real estate agents like those at Keller Williams Realty, Coldwell Banker Realty, and RE/MAX who focus on investment properties can help identify multi-family homes and condos suitable for Airbnb conversion in Roxbury's emerging neighborhoods. National services include Mashvisor, which offers rental property analysis and ROI calculations, AirDNA for short-term rental market data and performance metrics, and Awning, a real estate investment platform that helps investors find and finance rental properties. Boston-based investment firms like Boston Real Estate Investments and local property management companies such as RedAwning and Vacasa can provide ongoing management services. Additional national platforms include Roofstock for turnkey rental properties, BiggerPockets for investor networking and education, and local Massachusetts-based companies like Boston Pads and Rental Beast that can assist with market research and property identification in the Roxbury area, particularly around the rapidly gentrifying sections near downtown Boston.