52 Pleasant Street
Town
$2,495,000
Bed: 4 Bath: 2.5
Pleasant Breeze is situated on a 5,000+ square foot lot in the Old Historic District and just moments from Main Street. This welcoming and well-maintained c. 1930 Cape Cod home, thoughtfully renovated in 2002, offers a blend of historic character and modern comfort. With four bedrooms and 2.5 bathrooms, the open floor plan is perfect for island living and entertaining, featuring a bright kitchen, dining, and living area enhanced by vaulted ceilings that flood the space with natural light.
Step outside to enjoy outdoor living on a spacious deck overlooking mature gardens and a generous yard, with ample parking for convenience. Additional highlights include a detached shed/workshop—perfect for storage or creative pursuits—and a backup generator for peace of mind.
This timeless property, nestled in one of the island’s most desirable neighborhoods, is ready to welcome its next chapter.
Berkshire Hathaway HomeServices Island Properties Nantucket
26 Old Tom Nevers Rd
Tom Nevers
$8,250,000
Bed: 6 Bath: 5.5
Escape to your private oasis on Nantucket Island. This exceptional property offers the ultimate coastal lifestyle, featuring a stunning upside-down main house, a newly built guest cottage, and a serene, secluded pool—all just steps from the beach. The main house boasts approximately 3,000 square feet of exquisitely finished living space, including four spacious bedrooms, four full bathrooms, and a powder room. Thoughtfully designed to capture breathtaking Atlantic Ocean views, the home showcases a beautifully curated interior with timeless coastal details and designer lighting throughout. The state-of-the-art kitchen is equipped with top-of-the-line
appliances and elegant finishes, seamlessly flowing into open living and dining spaces ideal for entertaining. Set on over an acre of professionally landscaped grounds, the property offers a peaceful and private pool area perfect for unwinding after a day by the sea. This is a rare opportunity to own a refined and inviting coastal retreat that perfectly blends luxury, comfort, and Nantucket charm.
Douglas Elliman Nantucket
26 Old Tom Nevers Rd
Tom Nevers
$8,250,000
Bed: 6 Bath: 5.5
Escape to your private oasis on Nantucket Island. This exceptional property offers the ultimate coastal lifestyle, featuring a stunning upside-down main house, a newly built guest cottage, and a serene, secluded pool—all just steps from the beach. The main house boasts approximately 3,000 square feet of exquisitely finished living space, including four spacious bedrooms, four full bathrooms, and a powder room. Thoughtfully designed to capture breathtaking Atlantic Ocean views, the home showcases a beautifully curated interior with timeless coastal details and designer lighting throughout. The state-of-the-art kitchen is equipped with top-of-the-line appliances and elegant finishes, seamlessly flowing into open living and dining spaces ideal for entertaining. Set on over an acre of professionally landscaped grounds, the property offers a peaceful and private pool area perfect for unwinding after a day by the sea. This is a rare opportunity to own a refined and inviting coastal retreat that perfectly blends luxury, comfort, and Nantucket charm.
J Pepper Frazier Co.
3 North Gully Road
Sconset
$3,895,000
Bed: 2 Bath: 2.5
Enjoy spectacular views of sunrise or sunset from all rooms of this exquisite beach home. Located in Codfish Park this cottage offers direct beach access and privacy from the adjacent conservation land to its north. Renovations in 2009 and numerous updates in the past 10 years including: new heat pumps in 2025, new hot water tank in 2020, redid bedroom off porch, added ac, added windows to porch, custom made bunk beds in loft, added barn door in basement, re-did countertops in mudroom/laundry/storage area, painted floors, and new boiler 2020, make this cottage move-in ready.
Coldwell Banker Res Brokerage Nantucket
42 Chuck Hollow Road
Tom Nevers
$8,995,000
Bed: 8 Bath: 5
Situated in Tom Nevers East, just minutes from the Nantucket Golf Club and the village of Sconset, Hollyhock is a five-bedroom residence accompanied by a three-bedroom guest cottage, all set on three rolling acres that offer exceptional privacy, high elevations, and sweeping views from both floors of the Atlantic Ocean, conservation land, and Tom Nevers Pond. Originally constructed in Hanover, Massachusetts in 1840, the distinctive barn-style main house was relocated to Nantucket in 1979. Both the main house and cottage were thoughtfully reimagined by Victoria Hagan. She has become renowned for her intelligent integration of architecture and interior design and her refined use of materials. The current owner also has an acclaimed design background and has brought the property to a new level with enhanced indoor and outdoor spaces. New bluestone patios, outdoor fireplace and dramatic gardens all within a totally fenced in perimeter. A large 60′ x 20′ heated saline pool with retractable cover creates a backdrop for an expansive lawn.
Lee Real Estate
65B Surfside Road
Mid Island
$849,000
Bed: Bath:
Opportunities abound on this vacant lot located in an established area of Surfside. R-5 zoned with 2,000 square feet of allowable ground cover to build your dream home or investment property. Property is conveniently situated near mid-island shopping, Town and Surfside Beaches. Utilities (water, sewer and conduits for electric) have all been brought to and stubbed at the property.
William Raveis Nantucket
3D Windy Way
Mid Island
$895,000
Bed: 2 Bath: 1
This sunny second-floor unit with two bedrooms and one bath is conveniently located in the building behind Brix and was thoroughly renovated in 2017. It offers 745 square feet of living space with an open floor plan, hardwood floors, central air conditioning, and a radiant heat bathroom floor. The updated kitchen, ample storage/closet spaces, and an exclusive two-story deck for Unit D are standout features. The condominium also includes one designated parking space. Its prime location offers easy access to the WAVE and the Surfside Road bike path, The Muse, 45 Surfside, schools, and South Shore beaches. It’s move-in ready!
Fisher Real Estate
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