27 Wigwam Road
Madequecham
$4,995,000
Bed: 5 Bath: 4.5
Tucked near one of Nantucket’s most beloved South Shore beaches, this 5-bedroom, 4.5-bath upside-down beach house is a true coastal gem. Designed for both comfort and style, the home features soaring wood-beamed ceilings, an intricately inlaid compass rose in the hardwood floors, and a classic widow’s walk offering panoramic ocean views. With three distinct living areas—one on each level—plus a loft, there’s room for everyone to spread out or come together. The well-appointed kitchen opens seamlessly to the dining area and sunny second-floor decks, perfect for entertaining. With room for a pool, stunning ocean-facing vistas, and exceptional character inside and out, this home offers the ultimate Nantucket lifestyle.
Maury People Sotheby’s International Realty
1 Weetamo Road
Pocomo
$8,995,000
Bed: 5 Bath: 4.5
The property is described by its views.The views of Polpis Harbour, Nantucket Harbour and all the way into Nantucket Town. The home designed by Botticelli & Pohl was built take advantage of these views. The home has large rooms that all have great light. The kitchen has top of the line gourmet appliances. The 5 bedrooms are all of ample size. The primary has two adjioning rooms for relaxation or work. The pool house affords more options.
William Raveis Nantucket
41 Monomoy Road
Monomoy
$16,250,000
Bed: 6 Bath: 7
Spend your Nantucket summer in this turn-key, spacious and special home, nestled in the heart of Monomoy. The professionally decorated property completed by Kathleen Hay Designs is available for July and August 2025 occupancy. The 16×38 infinity edge pool and spa is surrounded by two spacious porches and a patio with a gas fire pit. The thoughtful landscaping features a cutting garden, enhanced privacy screening, deer fencing and a variety of outdoor seating areas.The home is adjacent to a 4+acre parcel of Nantucket Conservation Foundation land affording privacy and boasts second floor water views of Nantucket harbor.
Atlantic East Nantucket Real Estate
334 Madaket Road
Madaket
$1,895,000
Bed: 3 Bath: 3
THIS IS THE ULTIMATE Madaket beach house, the two structures were RECENTLY RELOCATED on the lot with a new 8-foot foundation, still with the most breathtaking unobstructed panoramic ocean views from almost every window! Enjoy front row seats to watch & experience the most epic & unforgettable sunsets on the East Coast. Well-maintained and spacious, the sun-drenched interior features an updated gourmet kitchen, an open-concept living area with a loft, three bedrooms, and three full bathrooms (two bedrooms with private full bathrooms on the 1st & 2nd floors). The private office or den can also be used for extra sleeping. A stone’s throw to Millies, some of the island’s best beaches, and easy access to Hither Creek for boating & fishing. You won’t want to leave this coastal paradise. It also offers a ROBUST RENTAL HISTORY, generating over 100k a year in income.
J Pepper Frazier Co.
3 Whitetail Circle
Tom Nevers
$3,495,000
Bed: 3 Bath: 2.5
Nestled on a high ridge in Tom Nevers, this beautifully crafted 3-bedroom, 2.5-bathroom home sits on 2.75 acres, offering breathtaking views across the Atlantic Ocean, Sankaty Lighthouse, and three of Nantucket’s renowned golf courses—Sconset, Sankaty, and Skinners. Built by the legendary Chris Holland, the home has been meticulously maintained and serves as the perfect base for quintessential Nantucket summers, just a short distance from the charming village of Sconset. With over two-thirds of the property still undeveloped, there is ample potential for future expansion. The property currently has a 4-bedroom septic system, with the possibility to increase septic capacity to support 10+ bedrooms and the potential to add an additional home. This unique property is a rare offering with endless possibilities, making it the perfect Nantucket retreat for today and a blank canvas for tomorrow.
Fisher Real Estate
10 Silver Street
Town
$7,495,000
Bed: 8 Bath: 9
Modern Elegance in the Heart of Town- 10 Silver Street presents a rare opportunity to own a newly constructed retreat in one of Nantucket’s most coveted neighborhoods. Thoughtfully designed and impeccably built, this exquisite property features a gracious main residence and a fully equipped guest cottage—each offering the perfect balance of form and function. The main house boasts 5 en suite bedrooms, including a flexible 3rd floor complete with a full bath—ideal as an overflow bedroom, home office, or playroom. White oak flooring and handcrafted oak stairwells elevate the interiors with natural warmth and understated sophistication. Soaring 12-foot ceilings in the lower level create a remarkable sense of space and light, enhancing the home’s brownstone-inspired floorplan. Tucked just behind, the guest cottage offers a fully independent cottage with 3 sleeping cabins thoughtfully situated on the lower level, allowing for an open living concept on the first floor with cathedral ceilings, full kitchen, living room, and 2.5 baths, the cottage is perfect for guests and entertaining. Located moments from downtown Nantucket’s shops, dining, and harbor, 10 Silver Street is a modern classic—a turnkey estate offering refined living in the heart of the island. Property slated for completion July 15th, 2025.
Maury People Sotheby’s International Realty
4 Lilac Court
Sandpiper
$2,195,000
Bed: 4 Bath: 4
4 Lilac Court offers three finished levels of living space with a total of 4 bedrooms, 4 full baths, 2 additional rooms that can be utilized as an office or playroom, 2 laundry rooms, and 2 full kitchens. Above ground, the home offers 3 bedrooms and 3 full baths with an additional office/playroom. In the lower level, with access from both an interior and exterior stair, is a basement apartment with 1-bedroom, an office, and a full kitchen and laundry. This home is new, modern, and bright. The complete package, this property has 2 off-street parking spaces and the option for a new owner to build a one-car garage with studio space above. Buyers may inquire about joining the new, resort-style clubhouse with an outdoor heated pool, and gym.
Maury People Sotheby’s International Realty
4 Shawkemo Hills Lane and 2 Wingspread Lane
Shawkemo
$21,400,000
Bed: 8 Bath: 7
Nestled in a coveted location on Nantucket, this exceptional 5-bedroom, 4-full-bath, 2-half-bath residence offers both grand living and thoughtful design. With expansive views of Nantucket Harbor and Nantucket Sound, this home features a generous layout, dramatic architectural details, and an oversized deck that is truly unique for the island. Perfect for both relaxation and entertaining, the main house boasts soaring ceilings, abundant natural light, and a seamless blend of indoor and outdoor living spaces. In addition to the main residence, the property includes a non-contiguous adjacent 2.84-acre lot, bringing the total acreage to an impressive 5.23 acres. With this extra land, the possibilities are endless—whether you envision creating a grand estate with additional structures, enhancing privacy, or preserving the beauty of this rare location for future generations. This estate offers a rare combination of luxurious living spaces, expansive views, and unbeatable Nantucket charm, making it an ideal retreat for both relaxation and entertaining.
Fisher Real Estate
4 Shawkemo Hills Lane
Shawkemo
$14,950,000
Bed: 8 Bath: 7
Nestled on 2.39 acres in a coveted location on Nantucket, this exceptional 5-bedroom, 4-full-bath, 2-half-bath residence offers both grand living and thoughtful design. With expansive views of Nantucket Harbor and Nantucket Sound, this home features a generous layout, dramatic architectural details, and an oversized deck that is truly unique for the island. Perfect for both relaxation and entertaining, the main house boasts soaring ceilings, abundant natural light, and a seamless blend of indoor and outdoor living spaces. This estate offers a rare combination of luxurious living spaces, expansive views, and unbeatable Nantucket charm, making it an ideal retreat for both relaxation and entertaining.
Fisher Real Estate
158 Madaket Road
Madaket
$2,750,000
Bed: Bath:
A rare and exceptional opportunity to own a prime 2-acre building lot on Nantucket Island. This expansive parcel is high, dry, and free of wetlands—an ideal canvas for your dream compound. Surrounded by acres of pristine conservation land, the setting offers unmatched privacy, tranquility, and natural beauty.
With approximately 3,470 square feet of available ground cover, the lot provides ample space for a main residence, guest house, garage, pool, and even a tennis court if desired. Town water is accessible at the street, and an approved 8-bedroom septic design will convey with the sale.
Create a legacy property tailored to your vision in one of the island’s most serene and protected environments. A unique opportunity to build your Nantucket dream estate.
Berkshire Hathaway HomeServices Island Properties Nantucket
11 Trotts Hill Road
Dionis
$4,250,000
Bed: Bath:
Fantastic Dionis location! This newly configured two-plus-acre parcel, which abuts Land Bank property, is nestled into a special enclave where vacant land rarely becomes available. This property is located down rural Trotts Hill Road, providing a terrific walking and biking network along the lightly traveled dirt roads. Access to North Shore beaches is a bike ride away. The site has wetlands, and the owners hired Nantucket Surveyors to create a site plan with footprints for a main house, guest house, pool, and an area for a six-bedroom septic system. The wetland delineations are recent, soil tests have been completed, and NHESP has reviewed the property.
Great Point Properties
12 Shimmo Pond Road
Shimmo
$5,800,000
Bed: 6 Bath: 6
Quintessential Nantucket Retreat: Enchanting 4-Bedroom Home with 2-Bedroom Cottage on expansive grounds in the prestigious Shimmo location.
Shimmo Pond Road, where sandy paths wind beneath leafy canopies and Nantucket Harbor beckons, this idyllic estate evokes the timeless charm of a countryside residence. Set on an oversized and private parcel, the beautifully proportioned 4-bedroom main house is accompanied by a delightful 2-bedroom guest cottage, both enveloped by lush gardens and mature trees that create a sense of intimacy and seclusion.
Perfectly suited for hosting family and friends or enjoying private retreat spaces, the property offers peace, comfort, and enduring character. Meandering garden paths, sunny terraces, and shady nooks lend a sense of magic, while the thoughtful layout allows for both quiet solitude and welcoming gatherings.
Just a stone’s throw from the shimmering waters of Nantucket Harbor and a short drive from the cobblestone streets of Nantucket Town, this rare offering marries countryside calm with coastal refinement. With over 2,000 square feet of allowable ground cover, the possibilities for expansion are plentiful.
A true jewel in the heart of one of Nantucket’s most serene and sought-after enclaves.
Maury People Sotheby’s International Realty
256 Polpis Road
Polpis
$33,000,000
Bed: 12 Bath: 13.5
256 Polpis Road is an exceptional 6.42-acre legacy estate that offers stunning views and direct water access to Polpis Harbor. This sprawling enclave has been refined and reimagined with the help of Botticelli & Pohl Architects and masterfully executed by Hehir Group Custom Builders. This rare offering is ready for immediate enjoyment for those seeking luxury living and the best that Nantucket has to offer. 256 Polpis Road boasts over 15,000 square feet of living space with sweeping vistas and panoramic views of the water, surrounded by lush natural landscape guided by Ahearn Landscape Design. At the heart of the property stands a spectacular main house boasting 10 bedroom suites, 3 floors of finished living space, floor to ceiling windows throughout highlighting the exceptional scenery, an 18X48′ infinity-edge swimming pool with superior water features including a spa, cabana, two-car garage, gym, movie theatre, and a billiard room.
Winding trails lead directly to the harbor, offering access to cherished Nantucket pastimes like kayaking, clamming, and waterfront exploration. At the heart of this exceptional estate is a historically significant, iconic boathouse—a rare and irreplaceable amenity that’s every skipper’s dream. The property also presents the potential to secure an estate-side mooring, further elevating its appeal.
Meticulously designed and curated by SLC Interiors, the residence is offered fully furnished, with no detail overlooked. Additionally, buyers have the opportunity to bring their vision to life with a custom two-bedroom carriage house. This is more than a home—it’s a Nantucket experience not to be missed.
Great Point Properties
31 Flintlock Road
Tom Nevers
$2,975,000
Bed: 3 Bath: 2.5
This Tom Never’s East private three bedroom 2.5 bath home is on a beautiful 1.3 acre lot. The high elevation offers a peek of the ocean. Lush landscaping and beautifully maintained gardens overlook a wonderful entertaining area with in-ground pool and multiple patio and deck spaces.
Atlantic East Nantucket Real Estate
19 Ahab Drive
Cisco
$3,495,000
Bed: 3 Bath: 2
This private property is ideally situated, approximately half a mile from Cisco Beach, with easy access to the bike path leading to Bartlett Farm, Cisco Brewery, and 167 Fish Market. This charming three-bedroom, two-bath home is located in a quiet and desirable Cisco neighborhood. The outdoor living space is south-facing, offering incredible light throughout the day, and features a separate garage. The property is 0.64 acres and features a four-bedroom septic system in place for potential expansion, should a buyer desire it.
Fisher Real Estate
103 Main Street
Town
$19,995,000
Bed: 6 Bath: 8
Cobble’s End sits at the crown of one of America’s most historic and picturesque streets—Main Street, Nantucket—where cobblestones meet brick. Nestled between iconic landmarks like the Tupancy mansion, the Three Bricks, and the island’s second-oldest home, this gracious Federal-style residence places you in the heart of town. Shops, banks, restaurants, churches, the post office, Marina Stop & Shop, and the in-town farmer’s market are just a short stroll away—no parking or driving needed. Enter from a covered portico into a light-filled home featuring four wood-burning fireplaces and a full-house generator. The grand walnut staircase spans three levels, anchoring a thoughtfully designed floor plan. To the right, a cozy library awaits. Straight ahead, an open kitchen, dining, and family room create a welcoming space for gathering. A piano room with French doors opens to a private brick patio with dining and lounge seating. Down a few steps, you’ll find a firepit, three chaise loungers, a seating area, and Nantucket’s last-approved in-town plunge spa. The property includes a charming historic studio cottage featuring original Queen’s Board planks, a fireplace, full bath with shower, wet bar, microwave, and Sub-Zero mini fridge—ideal for guests or a private retreat. Upstairs, a second-floor sitting room leads to the first guest bedroom with a queen bed and elegant ensuite bath. A large laundry room with double washers and dryers sits at the landing. Further on, a spacious office with a Vladimir Kagan chaise adjoins another guest room with ensuite bath. At the end of the hall, the VIP suite offers vaulted ceilings, expansive closets, and a spa-like bathroom with soaking tub, jetted shower, double vanity, and TV.
The lower level features two additional ensuite bedrooms, a second laundry area, wet bar, wine storage, and a fully equipped fitness room with SoulCycle bike and Precor elliptical.
Maury People Sotheby’s International Realty
2B Yawkey Way
Mid Island
$1,595,000
Bed: 2 Bath: 2.5
Spacious and well built duplex by local high-end contractor with 30 years experience building on the island. The left half has three floors of finished space. Only the highest quality materials were used in construction, with reclaimed oak floors, custom-built cabinetry, built-in entertainment center and ample storage throughout. A large deck in the rear offers private outdoor entertainment with a small yard and two-car off-street parking spaces. Red cedar roof, red cedar trim and Andersen 400 series windows provide the closest thing to exterior maintenance free living. Currently, there is a tenant with lease in Place until January 15, 2026, but there may be flexibility in ending lease early. The owners prefer to close anytime before December 31, 2025.
Maury People Sotheby’s International Realty
25C Pine Street
Town
$5,195,000
Bed: 4 Bath: 4
Situated on historic Pine Street, just off the cobblestones of Main, offering the opportunity to live in the heart of downtown Nantucket. This quiet, one-way street is just moments from award-winning restaurants, boutique shopping, and the ferries, placing the best of Town just moments from your door. Its location on one of Nantucket’s most iconic streets makes it a standout opportunity for those seeking convenience, charm, and nearby proximity to the island’s beloved historic landmarks.
Great Point Properties
7 Dooley Court
Mid Island
$2,795,000
Bed: 4 Bath: 4.5
State forest vibes and tall pine trees surround this inviting and spacious 4 bedroom house on 31,908 sq ft oversized lot at the end of a peaceful cul-de-sac. Recent improvements include the installation of central air, and the addition of three new bathrooms. With approximately 1856 sq ft of building footprint available, this property presents a multitude of options for the visionary buyer.
The cleared, buildable portion of the lot allows (pending approvals) for the expansion of the current dwelling, the addition of a second dwelling, and a pool. There’s also potential to finish the basement and add a studio above the garage.
The centrally located neighborhood is experiencing much new construction and growth, and gaining attention for its serene but vibrant energy and increasing property values. It is easily accessible to shopping, dining, fitness studios, bike paths, and multiple beaches, with Town just a short ride away. This is an exceptional opportunity to invest, enjoy, and build for the future. Conditionally approved HDC plans for the second dwelling are available.
J Pepper Frazier Co.
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