Multi Family Home For Sale in Oak Bluffs #43290

Property For Sale Description

Two Historic Oak Bluffs Cottages - Prime Location – Deeded Separately
Perched atop a gentle hill, surrounded by lush, established gardens in one of the island’s most storied neighborhoods, these two charming 1909 twin cottages offer a rare opportunity to own a piece of local history—just a short distance to the harbor, downtown, and the beloved Winston’s takeout.
Built at a time when automobiles were rare, these homes were sited with ease of access in mind. Though they have no driveways, convenient on-street parking is always available—local residents often find it easier to stroll, or bike, into town than drive.
Both homes are separately deeded, giving you the flexibility to own them jointly or individually, and the ability to create a compound with rental options. They are fully furnished and move-in ready, with a long history of use as rentals and community housing. Whether you're looking for a full-time residence, income-generating property, or a flexible retreat for extended family or friends, these cottages provide a unique and practical setup—ideal for dual living or multi-generational use.
Set against a backdrop of cool breezes and peaceful surroundings, these modest yet solidly built mirror image cottages feature warm, weatherproof interiors, ground-level entries, and ensuite bathrooms. While they may not compare in size to modern builds, their simplicity is part of their charm—and their history is unmatched.
The Hughes family, who once lived here, famously hand-dug full basements in both homes in the late 1920s—a remarkable feat in a neighborhood where most homes sit on crawl-spaces. This added space offers valuable storage, office, or expansion options rarely found in similar homes of the era.
With a strong local school system, a welcoming neighborhood, and the charm of yesteryear combined with present-day comfort, these homes are an ideal place to put down roots, invest in community, or create a home-away-from-home.
Keep them as they are, or add your own touches.

Floor 1: 4 bedrooms with ensuite full baths. Open kitchen, living and dining area in each cottage. #12 has a small office as well. Each cottage also has a a stone fireplace, outdoor shower and private patio.

Basement: Full basements in both cottages - VERY rare for antique cottages in this neighborhood. Fully ducted propane hot air system as well as the mini split.

Other Buildings:

Second Dwelling: ESd

Lot: Lush, established gardens and raised decks