Is Sherborn, Massachusetts Good for Airbnb Investment?

To start an Airbnb in Sherborn, Massachusetts, begin by researching local zoning laws and regulations through the Sherborn Planning Board and Building Department, as the town requires short-term rental operators to obtain a business license and comply with residential zoning restrictions that may limit rentals to owner-occupied properties or require special permits. Contact the Sherborn Board of Health for health and safety inspections, fire department for smoke detector and egress compliance, and ensure you meet Massachusetts state tax requirements including collecting 5.7% state excise tax and 6.25% sales tax. Find a suitable property that meets zoning requirements, preferably in residential areas where short-term rentals are permitted, and consider properties near Sherborn's conservation areas or within reasonable distance to Boston (about 20 miles) to attract guests. Furnish the space with quality essentials including comfortable bedding, kitchen supplies, WiFi, and safety equipment like smoke detectors and fire extinguishers as required by Massachusetts fire codes. Create your Airbnb listing with professional photos highlighting Sherborn's rural charm and proximity to Boston, setting competitive rates based on similar properties in nearby towns like Natick or Wellesley. Manage your property by establishing clear house rules, maintaining regular cleaning schedules, responding promptly to guest inquiries, and keeping detailed records for tax purposes while ensuring ongoing compliance with Sherborn's local ordinances and any homeowners association restrictions if applicable.

To identify profitable short-term rental properties in Sherborn, Massachusetts, focus on location criteria including proximity to Boston (30 miles southwest), access to major highways like Route 16 and I-95, and nearness to attractions such as Sherborn Town Forest and Farm Pond. Target property features like 3-4 bedroom single-family homes with modern amenities, outdoor spaces, parking, and historic New England charm that appeals to families and business travelers seeking suburban retreats. Conduct pricing analysis using AirDNA and Mashvisor to evaluate average daily rates ($150-250 range estimated), occupancy rates (60-75% projected), and seasonal demand patterns, particularly during fall foliage and summer months. Research competition by analyzing existing STR listings within 5-mile radius, studying their pricing strategies, amenities, and guest reviews to identify market gaps. Utilize tools like Rabbu, STR Helper, and local resources including Sherborn Planning Board regulations, Massachusetts STR laws, Norfolk County property records, and connect with local real estate agents familiar with the Dover-Sherborn area to understand zoning restrictions and neighborhood dynamics that could impact profitability.

To obtain an Airbnb/STR permit in Sherborn, Massachusetts, you must first contact the Sherborn Building Department at Town Hall located at 19 Washington Street to initiate the application process, as the town requires short-term rental operators to obtain a lodging house license under state regulations. Required documents typically include a completed application form, proof of property ownership or lease agreement, floor plans of the rental space, certificate of occupancy, proof of liability insurance (minimum $1 million coverage), fire safety inspection certificate from the Sherborn Fire Department, and a site plan showing parking arrangements and septic system details if applicable. The application fee is estimated at $200-400 annually, with additional inspection fees of approximately $100-200 for fire and building safety reviews. You must also register with the Massachusetts Department of Revenue for room occupancy tax collection and obtain a business certificate from the Town Clerk if operating under a business name. The timeline for approval typically takes 4-8 weeks from submission of a complete application, depending on scheduling of required inspections and any necessary corrections. Sherborn-specific requirements include compliance with the town's zoning bylaws which may restrict STRs in certain residential districts, adherence to septic system capacity limits for additional occupancy, maintaining adequate off-street parking (typically 2 spaces minimum), and ensuring the rental meets all building and fire codes including proper egress windows, smoke and carbon monoxide detectors, and maximum occupancy limits based on square footage and septic capacity.

Short-term rentals (STRs) in Sherborn, Massachusetts operate under state regulations as the town has not enacted specific local ordinances governing STRs as of 2023. Under Massachusetts state law, STRs are generally legal but must comply with state tax requirements including collecting and remitting state and local taxes through platforms like Airbnb and Vrbo. Sherborn, being a small residential town of approximately 4,000 residents in MetroWest Boston, has not implemented the restrictive zoning bylaws that some neighboring communities have adopted, meaning STRs can typically operate in residential areas provided they meet basic safety and tax compliance requirements. However, operators must still adhere to local building codes, health regulations, and any applicable homeowners association restrictions. The town has not designated any specifically prohibited areas for STRs, though properties must comply with standard residential use regulations. Recent trends in Massachusetts show increasing local regulation of STRs, but Sherborn has maintained a relatively permissive stance compared to communities like Boston or Cambridge which have implemented caps, registration requirements, and zoning restrictions since 2019-2022.

The most attractive areas for Airbnb investment in Sherborn, Massachusetts include the historic town center near the Sherborn Community Center and Town Hall, which draws visitors interested in New England colonial architecture and local events like the annual Dover Sherborn Boosters Road Race. The neighborhoods around Farm Pond and Powisset Farm offer scenic waterfront and rural experiences that appeal to nature enthusiasts and families seeking peaceful retreats from Boston, just 45 minutes away. Properties near the Charles River Recreation Area attract outdoor recreation tourists for kayaking, fishing, and hiking activities year-round. The residential areas along South Main Street and Woodland Road are ideal due to their proximity to both Wellesley College events and corporate travelers visiting nearby Natick's business district, including companies like MathWorks and Boston Scientific. Additionally, homes near the Sherborn Inn area benefit from overflow demand during peak foliage season (September-October) and graduation periods at nearby prestigious institutions, with properties typically commanding premium rates during these high-demand periods.

In Sherborn, Massachusetts, Airbnb hosts are subject to the state's 5.7% short-term rental excise tax on rentals of 31 days or less, which applies to properties rented for fewer than 14 days per year or more than 14 days annually. Additionally, hosts must collect the state's 6.25% sales tax on short-term rentals. Sherborn does not impose a separate local lodging tax beyond state requirements. The state excise tax is collected by hosts from guests and remitted quarterly to the Massachusetts Department of Revenue, while sales tax follows standard Massachusetts sales tax remittance procedures. Airbnb may collect and remit these taxes directly on behalf of hosts through their platform for eligible listings. Properties rented for 14 days or fewer per year are exempt from the short-term rental excise tax but may still be subject to sales tax depending on circumstances, and rentals of 31 days or longer are exempt from both the excise tax and sales tax requirements.

To start an Airbnb in Sherborn, Massachusetts, expect total costs around $850,000-$950,000. Property purchase represents the largest expense at approximately $800,000 based on Sherborn's median home price as of 2023. Furnishing costs typically range $15,000-$25,000 for a complete home setup including beds, linens, kitchen essentials, and living room furniture. Initial setup costs including professional photography, listing creation, and basic renovations average $3,000-$5,000. Permits and fees in Massachusetts include short-term rental registration ($200-$500), potential local licensing fees ($100-$300), and tax registration which is typically free. Insurance costs increase by $1,000-$2,000 annually for short-term rental coverage. Utility setup and deposits average $500-$800 for electricity, gas, water, internet, and cable. First six months operating costs include utilities ($1,200-$1,800), cleaning services ($2,400-$3,600 assuming $40-60 per cleaning), maintenance and supplies ($1,000-$1,500), platform fees to Airbnb averaging 3% of bookings, and marketing expenses ($500-$1,000). Property taxes in Sherborn average 0.7-0.9% annually, adding approximately $5,600-$7,200 for six months.

Airbnb properties in Sherborn, Massachusetts typically generate annual revenues between $25,000-$45,000 for whole-home listings, with average daily rates ranging from $150-$280 depending on property size and amenities. Operating expenses generally consume 40-50% of gross revenue, including cleaning fees ($75-$125 per turnover), property management (15-25% of revenue), utilities ($200-$400 monthly), insurance ($1,200-$2,000 annually), and maintenance costs ($2,000-$4,000 yearly). Net profit margins typically range from 15-25% for well-managed properties, with successful hosts achieving higher margins through strategic pricing, excellent guest experiences, and efficient operations. Properties within walking distance of Sherborn's town center or featuring luxury amenities like pools, hot tubs, or scenic views command premium rates and achieve 70-85% occupancy rates during peak seasons (May-October). A typical 3-bedroom colonial in Sherborn generating $35,000 annually might incur $18,000 in expenses, yielding approximately $17,000 in net profit (49% margin), while properties requiring significant renovations or lacking distinctive features often struggle with occupancy rates below 50% and profit margins under 10%. Success factors include professional photography, responsive communication, consistent 5-star ratings, competitive pricing strategies, and proximity to Boston (20 miles) which attracts business travelers and weekend visitors seeking suburban retreats.

Airbnb investments in Sherborn, Massachusetts typically generate annual ROI of 8-12% with cash-on-cash returns ranging from 6-10%, based on the town's proximity to Boston (25 miles west) and appeal to visitors seeking suburban retreats near metropolitan amenities. Properties in Sherborn, with median home values around $1.2-1.5 million, can command nightly rates of $200-350 depending on size and amenities, with occupancy rates averaging 60-70% annually due to seasonal demand from leaf-peepers, business travelers, and families visiting the area's historic sites and nature preserves. Initial profitability typically occurs within 18-24 months after accounting for startup costs, furnishing, and local regulations, while properties near Sherborn's town center or with unique features like historic charm or large lots tend to achieve the higher end of ROI projections at 10-12% annually, with some investors reporting cash-on-cash returns reaching 12-15% in peak performance years when occupancy exceeds 75%.

STRSearch is a leading national platform that specializes in identifying profitable short-term rental properties for investors looking in Sherborn, Massachusetts. Local real estate agents like those at Coldwell Banker Realty and William Raveis Real Estate have extensive knowledge of the Sherborn market and can identify properties suitable for Airbnb investments. National services include Mashvisor, which provides rental property analytics and market data, and BiggerPockets, which offers investment property search tools and investor networking. AirDNA provides short-term rental market analysis and revenue projections for the Sherborn area. Local property management companies like Vacasa and RedAwning can help investors identify and manage profitable Airbnb properties in the region. Real estate investment firms such as Roofstock and Fundrise also offer services for finding rental properties, though their Sherborn inventory may be limited. Additionally, local real estate agents at Compass and RE/MAX have experience working with investors seeking vacation rental properties in the greater Boston suburbs including Sherborn.