45 Pleasant Street
Town
$5,170,000
Days on Market: 20
Bed: 11 Bath: 11
An exceptional opportunity situated in the heart of Nantucket Town. A rare offering featuring two fully furnished, independent homes on one lot, just moments to Main Street.
This unique compound includes a 7-bedroom, 4.5-bath home with four finished levels and a 4-bedroom, 4-bath residence with three finished levels, each offering inviting interiors and private patios complete with firepits. Recent upgrades—central air, new roofs, new appliances, and more—make both homes comfortable and carefree. Off-street parking for four cars adds convenience rarely found in town. Perfect for multi-generational living, guest accommodations, and strong rental income. Morning coffee at your favorite café, afternoons wandering through boutiques, evenings dining at your favorite restaurant … all just moments from your doorstep creating the ideal setting for effortless island living.
A proven rental powerhouse, generating over $300K in 2025, with $265K already committed for 2026, largely from repeat guests who return year after year for its comfort and unbeatable location. And it gets even better, a low-mileage 2022 Jeep Wrangler Sahara (4-door) comes with the sale!
Whether you choose to live in one home and rent the other, create a cherished family compound, or enjoy both as high-yield investments, this in-town property delivers unmatched flexibility, lifestyle, and value.
1 Toombs Court (LOT B)
Mid Island
$1,000,000
Days on Market:
Bed: 0 Bath: 0
9,557 sq ft lot in CN zoning.
16A Boynton Lane
Mid Island
$835,000
Days on Market: 132
Bed: 2 Bath: 2
This well-designed 2-bedroom, 1-bath condo offers comfortable living across three levels, conveniently situated near all mid-island amenities and less than two miles from Surfside Beach.
Contact us for more information.