13 Derrymore Road
Cliff
$4,700,000
Days on Market: 135
Bed: 5 Bath: 5
Ideally located in the sought-after Cliff neighborhood, this turnkey five-bedroom home is just moments from North Shore beaches, The Westmoor Club, Something Natural, and downtown Nantucket. Offered fully furnished, the property features three levels of living space, a first-floor primary suite, two inviting living areas, and ensuite guest bedrooms—making it the perfect island retreat.
33 Pleasant Street
Town
$3,490,000
Days on Market: 121
Bed: 5 Bath: 5
Welcome to 33 Pleasant Street, a hidden gem in a prime in-town location. Set back from one of Nantucket’s most prominent streets, this beautifully private, multi-tiered sanctuary is accessed via a charming cobblestone path and surrounded by lush, terraced landscaping and mature trees. The main residence is a classic two-story clapboard home offering four bedrooms and four and one half bathrooms across four thoughtfully designed levels, including a stunning glass atrium that floods the interior with natural light and frames views up toward an outdoor gazebo. The detached one-bedroom, one-bathroom cottage with its own living space is perfectly sited for privacy, making it ideal for guests, extended family, or flexible use as a rental or studio space. A Juliet terrace overlooks the garden, completing the scene. This extraordinary property must be seen in person to fully appreciate its unique combination of space, serenity, and proximity to downtown.
78 Cliff Road
Cliff
$8,750,000
Days on Market: 363
Bed: 5 Bath: 5
Sprawling one-level house and newer 2005-built garage/apartment in a prime Cliff Road location. Located close to all of the amenities of Nantucket Town and minutes to sandy Steps Beach off of Lincoln Circle. The property is offered for sale as as a whole on 3 oversized Land Court registered lots. Should one wish to build a new estate (or three), there is HDC-approved demo/move permits in process for both structures. There is also a Sewer Department permit for a sewer system extension for up to 3 connections.
1 Brier Patch Road
Quidnet
$3,375,000
Days on Market: 8
Bed: 4 Bath: 4
Welcome to this spectacular private retreat on the edge of Quidnet Village. This attractive home offers 4 spacious bedrooms, 3.5 baths, and 2 cozy fireplaces within an open floor plan. The interior is thoughtfully designed with two primary suites—one conveniently located on the main floor and another on the second floor. Multiple common rooms provide ample space for relaxation and entertainment indoors. Enjoy the naturally landscaped outdoor areas, featuring a large wisteria-covered front porch, a pergola-shaded rear patio, and an expansive backyard perfect for outdoor activities. There’s ample room for a pool and cabana, the possibilities for customization are endless. The large open full basement offers great potential for additional living space or storage. The property is a true sanctuary, abutting over 40 acres of NCF conservation land, ensuring privacy and a connection to nature.
10 New Lane
Town
$5,300,000
Days on Market: 62
Bed: 4 Bath: 4
“Winds Aloft” 5 Bedrooms | 4 Baths | Private Pool | Two-Car Garage with Guest Suite.
Tucked away on a peaceful and generously sized 20,000 sq ft lot, “Winds Aloft” is an exceptional Nantucket residence that blends timeless design with effortless coastal living.
The sun-drenched, open-concept main house features three bedrooms plus a flexible den space, and gracious layout designed for both comfort and entertaining. Expansive windows frame picturesque views of the beautifully landscaped yard, lush gardens, and a private swimming pool, creating a seamless connection between indoor and outdoor living.
Perfect for hosting guests or working remotely, the detached two-car garage includes a fully equipped one-bedroom guest suite above—offering flexible space for extended family, visitors, or a private office retreat.
Located in R-1 zoning, this oversized parcel allows for 30% ground cover, leaving generous square footage for future expansion or a potential subdivision (with appropriate approvals). Just 0.8 miles from the center of downtown Nantucket and with easy access to bike paths and Nantucket’s pristine beaches, “Winds Aloft” offers exceptional lifestyle and investment potential.
Whether as a personal retreat or a high-performing rental, this distinctive property presents a rare opportunity to enjoy—and grow into—one of the island’s most desirable locations.
126 Main Street
Town
$14,500,000
Days on Market: 197
Bed: 5 Bath: 5
A once in a lifetime opportunity to own a bespoke, custom compound on historic Main Street Nantucket built by renowned design/build firm, The Stahl Group. Over the course of three years, three generations of luxury designers and builders came together to reimagine an historic home, situated on a rare double lot on upper Main Street. With the utmost attention to detail and high end craftsmanship, 126 Main Street is a true passion project that is ready for its next steward. A total of five en suite bedrooms and en suite sleeping loft provide plenty of space to entertain family and friends or enjoy true multigenerational family living. Every detail imaginable has been thought of, including and especially in the kitchen where a Lacanche range and hood, hand selected in Burgundy, offer a stunning focal point. The wet bar and butler’s pantry lend themselves to beautiful entertaining reminiscent of the most high end homes, only to be outdone by the custom mahogany wine cellar. Generous and gracious living, dining, and entertaining spaces offer many options for an elegant, in town Nantucket life.
A full lower level with two exterior access points offers its own self sufficient guest suite comprising two en suite bedrooms, kitchenette, living, dining, outdoor shower, powder room, and laundry suite.
Multiple dining and entertaining spaces flow into the oversized garden and rear lot, which can be fully customized to suit your needs. With approved hardscaping and landscaping plans, as well as HDC approval to build a custom 3000sf guest house, the rear lot can be crafted into the perfect complement to elevate your lifestyle. The possibilities are endless to put the finishing touches on an in town Nantucket dream home.
38 Monohansett Road
Surfside
$3,200,000
Days on Market: 273
Bed: 6 Bath: 6
Six bedrooms, six full baths of new construction in Surfside on over 1.8 acres with a pool, wraparound porch and close proximity to South Shore beaches. Open floor plan with gas fireplace, high end appliances, center island and french doors leading out to the pool area. Three floors of finished living space with shiplap walls and custom built ins. A 18′ x 36′ pool with bluestone patio and large yard help to complete this offering. There is approximately 1500 sq/ft of ground cover remaining and HDC approved plans for a cabana/outdoor kitchen to be added adjacent to the pool.
137 Surfside Road
Surfside
$2,600,000
Days on Market: 112
Bed: 4 Bath: 4
If your ideal island summer includes the sound of the surf, starlit nights, easy access to Nantucket’s favorite ocean beach, and a bike path leading to town, then 137 Surfside Road is the perfect match. Ideally located just ½ mile from Surfside Beach and 2 miles from downtown Main Street, this home blends beachside serenity with island convenience. Located on a peaceful lane shared by only five other homes it offers a quiet retreat while keeping you effortlessly connected. With the Surfside Road bike path and The Wave bus route just outside your door, getting to town, the beach, and other island destinations couldn’t be easier. Set on a spacious half-acre lot, the home features a total of four bedrooms: three bedrooms and three baths in the main house, plus a studio and bathroom above the attached garage. Zoning allows for an in-ground pool so whether you’re looking for a vacation escape or a year-round home, 137 Surfside Road puts you just moments from the ocean while keeping you connected to all that Nantucket has to offer. Whether you’re looking to restore or reimagine, this property presents a rare opportunity to create something truly special.
2 Towaddy Lane
Sconset
$2,700,000
Days on Market: 78
Bed: 3 Bath: 3
This well maintained three bedroom, two bath home with a loft is located on the corner of a quiet cul-de-sac in ‘Sconset. The partially furnished property offers a spacious yard and deck to enjoy outdoor entertaining. This charming home has lovely mature landscaping, an outdoor shower, oversized shed and off-street parking. The property is in close proximity to ‘Sconset Center and all the village has to offer.
3B Yawkey Way
Mid Island
$1,425,000
Days on Market: 135
Bed: 2 Bath: 2
Step into this stunning, sun-drenched home offering four beautifully finished floors of living space. Featuring reclaimed oak floors and custom-built cabinetry, this home combines warmth with a thoughtful design. Enjoy a built-in entertainment area perfect for cozy nights or hosting guests, a convenient laundry closet, and generous storage options. The private deck and landscaped yard provide an outdoor escape, while the two-car parking space adds convenience. A true blend of charm, functionality, and comfort. 3 Yawkey Way is move-in ready.
12 Oak Hollow Lane
Hummock Pond
$3,400,000
Days on Market: 265
Bed: 3 Bath: 3
Sub division possibilities! Welcome to 12 Oak Hollow Lane located in the sought-after Hummock Pond area of Nantucket. This charming 1970s home features 3 bedrooms and 2 baths, offering a cozy foundation to make your island dreams come true. With ample space for expansion, you can personalize and enhance this property to suit your unique vision. Town sewer available on the street, Nestled in a prime location, you’ll be just moments away from the south shore Cisco beaches, the popular Cisco Brewery, and the local delights of Bartlett Farm and 167 Fish Market. Whether you’re seeking a summer retreat, a year-round residence, or an investment opportunity, this property provides endless possibilities, including doing a two lot sub division.
17 Pilgrim Road
Cliff
$6,825,000
Days on Market:
Bed: 8 Bath: 8
*Recorded sale is for land only, accompanied by separate $7m construction contract. Welcome to Cliff living at its finest! 17 Pilgrim is a rare opportunity to own a brand new home on a fabulous oversized property within walking distance to Town, north shore beaches and the Westmoor Club. Hanley Development has partnered with Sophie Metz Design to create a magnificent 7,600+ square foot compound featuring a 6 BR main house with garage, 2 BR guest house and pool/spa. The spacious main house has over 5,800 sq ft of finished living space with an attached garage and fully finished basement. The 2-story guest house offers an additional 1,826 sq ft of finished area with downstairs living space including full kitchen and two bedrooms upstairs. All bedrooms in both main and guest house are en-suite! The outdoor living is highlighted by the 16×30 pool with raised spa, outdoor kitchen and dining and a covered patio with fireplace off of the guest house. Construction is underway with completion scheduled for fall of 2026. Buyers now would have the ability to customize finishes or sit back and await full turnkey delivery of their dream home on the Cliff!
7 Lily Street
Sconset
$5,050,000
Days on Market: 42
Bed: 4 Bath: 4
Nestled in the historic Actors Colony, established in the 1800s, 7 Lily Street beautifully blends coastal living with classic Sconset charm. Located in the heart of Sconset Village, this thoughtfully designed home features four bedrooms and four-and-a-half bathrooms. From its architectural style to the interior finishes, this home boasts superior craftsmanship, with shiplap walls and rich wood floors. The gourmet kitchen boasts custom cabinetry and high-end appliances, making it an ideal space for both everyday living and entertaining. Outside, the property has a stone patio surrounded by meticulously manicured gardens. The patio seamlessly blends indoor and outdoor spaces, creating an inviting area for dining and relaxing. The property also includes a private driveway and a one-car garage. This charming Sconset home is not to be missed!
2 White Elephant Way
Town
$7,600,000
Days on Market: 374
Bed: 4 Bath: 4
Welcome to 2 White Elephant Way, a stunning corner lot home in one of Nantucket’s most coveted in-town locations. As one of the first two homes offered by this prestigious company, the property boasts a prime spot just across from Lola 41 restaurant, providing effortless access to the town’s vibrant shops and restaurants. With a design that beautifully marries modern luxury and Nantucket charm, the home features a wrap-around porch perfect for leisurely watching the world go by. Inside, it includes four bedrooms and four and a half bathrooms, all within an open-plan living space ideal for entertaining family and friends.
50 Burnell Street
Sconset
$2,250,000
Days on Market: 27
Bed: Bath:
This ‘Sconset sanctuary abuts nine acres of preserved Sconset Trust land, affording one the opportunity to build your dream family compound in a quiet, tranquil setting. Mature vegetation throughout the property provides privacy with room to build, while still maintaining an abundance of space for a large yard. *Part of lot 167 new sub-division identified as lot 35.
8R Union Street
Town
$1,800,000
Days on Market:
Bed: 1 Bath: 1
8R Union Street presents a rare opportunity to own a quintessential Nantucket cottage in a premier downtown location. This one-bedroom, one-bath residence combines historic charm with thoughtful updates. Distinctive barn doors and classic cedar shingles create appealing curbside character. The second floor captures glimpses of the harbor, enhancing the home’s in-town allure. A private back patio and enclosed outdoor shower offer a quiet retreat, ideal for relaxing or entertaining. With two deeded off-street parking spaces, this property is a truly uncommon in-town find.
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