Enjoy a luxurious one-week escape to 28 Pleasant Street - known as "The Pleasant Pearl" - in Nantucket, a beautifully renovated 5-bedroom, 5-bath New England-style home located in the heart of Town. Just steps from Nantucket’s renowned dining, boutique shopping, and historic cobblestone streets — and less than one mile from the nearest beach — this 2,075-square-foot residence offers the perfect blend of classic island charm and modern comfort.
Thoughtfully designed for gathering, the home comfortably accommodates up to 10 guests and features elegant living spaces, a cozy outdoor fireplace, marble-appointed bathrooms, a chef’s kitchen with premium appliances and generous island seating, and a lovely outdoor dining area ideal for crisp coastal evenings.
Your Nantucket experience will be enhanced with a special Caviar Cocktail Evening hosted by Black River Caviar.
Bedroom Layout
1st Floor: King bedroom suite with en suite bath
2nd Floor: Master king suite, one guest queen bedroom, one guest bedroom with two twin beds, plus two bathrooms
3rd Floor: Queen bedroom retreat with en suite bath and space for a crib or toddler bed
The stay is available for one week during either September 5–Thanksgiving 2026 or September 4–Thanksgiving 2027.
Restrictions: The stay is available for one week during September 5–Thanksgiving, 2026 or September 4–Thanksgiving, 2027. Summer 2026 and Summer 2027 are blacked out, and additional blackout dates may apply. Valid only in 2026 or 2027. Cleaning fee and parking are included. No pets allowed. No age restrictions on children. The stay is transferable and may be gifted to someone other than the winner. Winner and guests must be respectful and mindful that this is a privately owned family home and treat it accordingly. Air and ground transportation not included. Caviar Cocktail Evening hosted by Black River Caviar on a mutually agreed upon date and time.
Donated By: Ryan & Lindsay Craig - Park Hollow Mortgage and Black River Caviar
