Wellesley, MA

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  • Performance
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Key Performance Metrics

Market snapshot

Performance indicators for the Wellesley short-term rental market based on reliable data.

Listings

15 / 68

Reliable / Active

Cap Rate

2%

Middle-Earners Gross Yield

Revenue

$45,375

Middle-Earners Revenue

Occupancy

60%

Middle-Earners Occupancy

Home Value

$2,067,574

Median Home Sale Price

Top Earners

$74,898

Top-Earners Revenue

Wellesley

Market Revenue Seasonality

Top Listings

Highest revenue

The highest-performing listings in Wellesley.

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B

Generally Investor friendly

Wellesley Regulations

Short‑term rentals are legal citywide and there’s no documented local STR licensing for non‑ADU units, but developers must clear state registration, $1M insurance, and verify occupancy; building an ADU triggers building permits, ZBA special permits, a 30‑day minimum, owner‑occupancy, and other zoning constraints. The absence of bans or hard caps is favorable, yet the ADU rules add moderate permitting and cost, keeping the regime friendly but not frictionless.

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About Wellesley

Wellesley is an affluent suburban town in Norfolk County, Massachusetts, located roughly fifteen miles west-southwest of downtown Boston along the western edge of the metropolitan area. With a population of approximately 29,000, the town has the polished, well-manicured feel of a classic New England suburb: tree-lined streets, historic homes, a tidy town center, and a strong sense of community anchored by civic pride and a highly regarded public school system. Wellesley is best known as the home of Wellesley College, one of the country's most prestigious liberal arts colleges, and the town also functions as a convenient gateway to the cultural and economic offerings of greater Boston while retaining a quieter, residential atmosphere of its own.

A defining landmark of the town is Wellesley College itself, whose picturesque campus features rolling lawns, collegiate Gothic architecture, and the serene waters of Lake Waban. The college's art museum, The Davis Museum, houses a notable collection of global art and is open to the public year-round, while the surrounding paths and arboretum offer a peaceful place for a walk. The campus is roughly at the heart of town, only a few minutes' drive from virtually anywhere in Wellesley.

Just a few minutes south of the town center, the Massachusetts Horticultural Society maintains its primary display garden, known as the Gardens at Elm Bank. The property includes formal gardens, a woodland trail, and seasonal displays that draw visitors from across the region, making it one of the most popular outdoor destinations in the immediate area. Its location along the Charles River in neighboring Wellesley and Natick places it within about a ten-minute drive of the town center.

For outdoor recreation, the Broadmoor Wildlife Sanctuary, operated by Mass Audubon, lies just a short drive west in Natick, approximately ten to fifteen minutes from central Wellesley. The sanctuary features more than eight miles of trails winding through fields, woodlands, and along the Charles River, and is a popular spot for birdwatching and quiet nature walks.

Of course, Wellesley's proximity to Boston is one of its most compelling features for visitors. Downtown Boston, with its Freedom Trail, waterfront, museum district, and Fenway Park, is reachable in roughly twenty-five to thirty-five minutes by car or via the commuter rail, which runs from Wellesley's two stations directly into Back Bay and South Station. Fans of the Boston Marathon will also recognize Wellesley as the site of the famous "Scream Tunnel" near the college, where spectators famously cheer runners at the race's halfway point.

Together, the town's leafy residential character, its collegiate and horticultural attractions, easy access to the New England countryside, and quick rail and road connections to Boston make Wellesley a comfortable and versatile base for short-term rental guests seeking a quieter stay within easy reach of one of America's most historic cities.

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