12 Longwood Dr
Tom Nevers
$3,950,000
Bed: 6 Bath: 5.5
12 Longwood Dr. is a magical property surrounded by manicured lawns and mature natural vegetation. The long winding driveway passes the 2 bedroom Guest Cottage before continuing down a slight grade to the expansive 4 bedroom Main House site. The Main House has an open floor plan with a cathedral ceiling living room, connected to a long hallway, creating privacy for the bedrooms. At the end of the hallway is the TV room. Two outdoor decks, a fire pit, and an apple orchard that produces different varieties, as well as a fruit-bearing pear tree, add to the special ambience of this property. A private path leads to the milestone bicycle path and easy access to Sconset Village. Across Milestone road are hundreds of acres of conservation land, cranberry bogs and miles of trails to walk or bike. Multiple locations available for a pool and a pool cabana.
William Raveis Nantucket
9 Millbrook Road (Portion)
Hummock Pond
$3,300,000
Bed: 0 Bath: 0
This two-acre vacant lot is located in the Hummock Pond area, on the edge of Cisco. This area is highly sought after for its proximity to South Shore beaches, Hummock Pond Road bike path, Cisco Brewery, 167 Seafood, and Bartlett’s Farm. The property benefits from abutting and nearby conservation lands that will ensure open space and provide walking trails. This setting offers a rural feel and abuts Land Bank property along two boundary lines. The property allows 3,200 square feet of ground cover.
Great Point Properties
2 York Street
Town
$2,550,000
Bed: 4 Bath: 3
Nestled in a quiet corner of Nantucket’s Historic District, 2 York Street offers a rare and captivating opportunity, just moments from the heart of downtown. This quintessential antique property features a 3-bedroom, 2-bathroom main house and a charming detached 1-bedroom, 1-bath studio—ideal for guests, extended family, or rental income. The main house sits on a 4,356± square foot lot, surrounded by mature gardens and tranquil yard, complete with a garden shed and off-street parking. Inside, you’ll find original wide-plank pine floors, four fireplaces, and a lightly refreshed kitchen and bathrooms. The open-concept kitchen, dining, and living area is filled with natural light and offers a seamless flow for entertaining or relaxed everyday living. The living room features a sunny bay window and an original wood-burning fireplace, providing a cozy space to unwind. The first-floor bedroom serves as a versatile overflow den or guest area, offering additional room for relaxation or entertainment. Upstairs, two generously sized bedrooms—one with a skylight and each with its own fireplace—offer antique charm and ambiance and share a spacious, well-appointed bath. Subdivision Potential This property may qualify for a potential 81L subdivision, offering the possibility to create two conforming lots (subject to approval). A rare chance to expand or reimagine this delightful home. A true Nantucket gem, rich in history and full of potential. Just blocks from Main Street, Great Harbor Yacht Club, the harbor, and the island’s renowned beaches, this home combines antique charm with modern possibilities—ready for you to make it your own. .
William Raveis Nantucket
41 Quidnet Road
Quidnet
$7,495,000
Bed: 3 Bath: 6
Tucked just moments from Quidnet Village and sheltered behind high hedges, this special property blends timeless Nantucket charm with thoughtful modern updates. Renovated and significantly expanded in 2008/9, the home features an open floor plan that seamlessly marries classic style with contemporary living. Nearly every room opens onto a beautifully landscaped, fenced-in lawn and garden, creating a natural connection between indoor and outdoor spaces. Highlights include a pergola-covered terrace, rolling green lawns, a covered kitchen-side patio, and a stunning outdoor fireplace perfect for gathering with friends and family on cool island evenings. Quidnet is unique to the island with a mature landscape, proximity to ocean and pond beaches, and low density
Maury People Sotheby’s International Realty
19 Boynton Lane
Mid Island
$6,795,500
Bed: 5 Bath: 4.5
Discover a one-of-a-kind opportunity at 19 Boynton Lane, Nantucket, MA, where commercial meets residential in an unrivaled setting. Situated in the heart of Nantucket and nestled within RC-2 zoning, this expansive property boasts 6,423 square feet of versatile space which can easily be described as “enormous”. This property is ideal for your entrepreneurial vision. With a fully equipped commercial kitchen, this property is primed for transformation into a multi-use structure; restaurant, market, bakery, florist, or more, offering a unique blend of business and residential potential.
Step into a world of possibilities with an open floor plan that welcomes a flood of natural light through large windows, creating a warm and inviting atmosphere. The property extends across a generous 27,442 square foot lot, presenting a private canvas for your outdoor commercial oasis, perfect for hosting guests or expanding your business operations.
Benefit from 24 parking spaces, a dedicated loading dock, and a convenient load-in area servicing both levels. The inclusionary housing provision facilitates a streamlined approval process with the Nantucket Planning Board, enhancing the ease of developing this blank slate to suit your aspirations, there is ample potential to transform the space to meet your specific needs.
This property also provides for 2 fully equipped 2nd floor apartments and a studio. The main apartment is a two level 2 BR 2 Full BA with an open kitchen living room, loft space and private outside deck. The middle apartment in split level with a separate main bedroom and spaces for additional twin beds for more capacity and full bath. The open studio has its own private entrance and bathroom. These living spaces are filled with natural light. The 2 bedrooms are fully equipped with full kitchens.
Seize this unique chance to own a versatile property loaded with potential. Contact me today to explore how 19 Boynton Lane can be a perfect location to initiate your commercial dream. This property should be seen to fully appreciate it capacity. Please book an appointment to see this property in person.
Compass MA LLC
27 Fair Street
Town
$5,995,000
Bed: 15 Bath: 14.5
Sitting high on Fair Street on a oversized rolling lot, 27 Fair Street was originally built as a single family home and then later converted to an inn with an annex building at the rear of the lot. There are approvals to reconfigure the existing inn into a six key inn and build three, free-standing two-story suites where the annex building currently exists. Or, convert back to a single family home with plenty of room for a guest house as the expansive lot has over 178′ of frontage on Hillers Lane.
J Pepper Frazier Co.
29 Fair Street
Town
$3,995,000
Bed: 9 Bath: 6.5
Originally built in 1709 for the George Bunker family. The property was converted to the Woodbox Inn in 1931. Located at the top of the hill, on one of Nantucket’s most charming streets, 29 Fair Street is a rare opportunity to restore a piece of Nantucket’s architectural heritage that’s steeped in history. Many original features are still intact. Approvals exist to keep as an inn with five keys (six bedrooms) or convert back to a single family home with opportunity for a guest house. Potential for sub-division.
J Pepper Frazier Co.
12 New Street
Town
$1,350,000
Bed: Bath:
Build your dream home on this unique parcel of land located in the Residential Old Historic District. Enjoy the charm of historic surroundings with freedom of new construction. One has the ability to bring together both character and comfort. Located on a quiet one way street between Pleasant Street and Orange Street, there is approximately 1,364 sqft of available ground cover with potential second floor harbor views. The high flat land is complimented by the surrounding mature trees. There is an existing 224 sqft structure located in the Eastern rear setbacks.
J Pepper Frazier Co.
1 East Hallowell Lane
Cliff
$6,900,000
Bed: 2 Bath: 3
A timeless classic off Cliff Road. Poised on a rise of land between Hinckley Lane and Gosnold Road close to Nantucket Sound beaches and convenient to Town. Authenticity is part of the allure. True to the character of a classic summer cottage, “Sachem Corner” sits on a on 14,300 sqft lot with room for expansion.
Lee Real Estate
167R Orange Street
Mid Island
$1,695,000
Bed: Bath:
Situated across from Land Bank property, which includes the Creeks Preserve and the Ottison family property, this lot offers water views and access to the Monomoy Creeks and features commercial zoning for mixed-use development (CMI). The CMI allows for mixed-use buildings to have one apartment per 2,000 square feet of land. Alternatively, the CMI allows one apartment per 1,250 square feet for a building with no commercial use. The lot has access to municipal utilities and pedestrian and bike paths. It is conveniently located near Town and other commercial centers, including Stop & Shop, Marine Home Center, the Mid-Island Post Office, and local banks. This prime location offers a variety of potential uses as well as natural amenities.
Fisher Real Estate
8 Skyline Drive 8R Skyline Drive & 46 Lovers Lane
Surfside
$14,850,000
Bed: 3 Bath: 3.5
Welcome to Serenity Farm, an exceptional 11.5 acre estate on picturesque Skyline Drive. Designed by Botticelli & Pohl and masterfully renovated in 2019 by Michael Sweeney Construction, this stunning retreat offers unparalleled privacy and space and recreation. The beautifully crafted main house features three bedrooms and three and a half bathrooms, complemented by an expansive barn originally built as an indoor riding arena. Now offering incredible versatility, the barn includes finished spaces such as a gym, a spacious barndominium, and outstanding recreation or equine opportunities. A heated saltwater pool, hot tub and a charming cabana provide the ultimate outdoor relaxation.
Thoughtfully designed outdoor spaces include a large, manicured lawn, mature trees, protected gardens with deer fencing, paddocks, and expansive fields, creating an enchanting landscape to host your family friends and community. A picturesque flower meadow attracts abundant songbirds, while the property’s direct border with the State Forest ensures lasting tranquility. Porches and patios connect indoor and outdoor spaces seamlessly, providing the perfect setting for entertaining or a quiet retreat. Despite its secluded ambiance, Serenity Farm remains just minutes from private aircraft access, as well as south-facing Surfside beaches and mid-island shops. With breathtaking pastoral views, refined amenities, and an unmatched connection to nature, this estate offers the ultimate Nantucket retreat.
Fisher Real Estate
8 Milk Street
Town
$6,250,000
Bed: 4 Bath: 4.5
Located in the heart of the desirable Old Historic District, this beautiful turn-key, antique home with 4 bedrooms suites has been mindfully renovated with no detail overlooked. This exceptional property sits on an oversized lot which includes off street parking, an oversized one car garage, a magnificent spacious rear yard with mature landscaping and beautiful front and side gardens – all hedged in to offer much privacy. There are many custom details throughout the house making for a timeless and stunning interior. The home features an eat-in kitchen area, extra wide antique wood floors, a gracious dining room, and two separate light filled sitting areas – ideal for family gatherings and entertaining. Prominently located just moments from Main Street, this is an ideal location for summer and/or year round living. 8 Milk Street is a unique offering with expansion possibilities and is not to be missed!
Lee Real Estate
33 Bartlett Road
South of Town
$3,595,000
Bed: 3 Bath: 3
Centrally Located Nantucket Retreat with Backyard Oasis.
Discover the perfect blend of custom and comfort in this newly renovated Nantucket home, ideally located with close proximity to Miacomet Golf Club, Surfside Beach and Town. Thoughtfully designed and currently configured as a five-bedroom, three-bath residence, this property offers exceptional versatility and a seamless indoor-outdoor lifestyle.
Step inside to an open-concept first floor featuring a custom chef’s kitchen with high-end appliances, flowing effortlessly into the bright living and dining areas—ideal for entertaining. Two spacious bedrooms on this level share a beautifully updated full bath with a stall shower.
Upstairs, the private primary suite offers a serene escape with a cozy sitting area and a custom-designed bathroom featuring a double vanity and oversized walk-in shower. The finished lower level expands the living space with a galley kitchen, TV/sitting area, two additional bedrooms, and a full bath—perfect for guests or future rental income.
The highlight of this property is the beautifully landscaped backyard oasis. Enjoy summer days around the 14×28 in-ground pool, host gatherings at the outdoor kitchen and wet bar with seating, and unwind by the wood-burning firepit under the stars.
Whether you’re seeking a year-round residence, a summer getaway, or an investment opportunity, this turnkey home offers limitless potential.
William Raveis Nantucket
155 Surfside Road
Surfside
$3,995,000
Bed: 4 Bath: 6
Escape to your own slice of paradise just moments from the shores of iconic Surfside Beach. Nestled in one of Nantucket’s most sought-after neighborhoods, this comfortably appointed 3 bedroom, 5 bathroom main house with a 2 story cottage offers the perfect blend of classic island charm and modern comfort.
Step inside to discover first floor 2 ensuite bedrooms, a den, and a hall bathroom. Upstairs is a light-filled open floor plan living room with vaulted ceilings, a fireplace, hardwood floors, and thoughtfully designed living spaces ideal for entertaining or relaxing after a day in the surf. The kitchen features granite countertops, and a large island that seats up to 10— perfect for gathering with friends and family. French doors lead to a deck overlooking a lush backyard, surrounded by mature landscaping for privacy and tranquility. The primary suite is a peaceful retreat with a spa-like en-suite bath. Additional bedrooms are generously sized with ample closet space. The home also includes a finished basement with a bonus room, sitting area, bathroom, laundry room, and 800+ bottle wine cave!
The large patio is perfect; whether you’re grilling out, lounging with a book, or hosting a sunset dinner, the outdoor living space offers a true extension of coastal life. In addition, there are multiple decks and plenty of shared and separate outdoor spaces.
Located just a short stroll or bike ride to Surfside Beach’s soft sand and rolling waves, and only minutes from downtown Nantucket’s world-class dining, shopping, and historic charm — this home is a rare opportunity to enjoy the best of island living year-round or as a summer getaway.
William Raveis Nantucket
10 New Lane
Town
$5,200,000
Bed: 4 Bath: 4
“Winds Aloft” | 5 Bedrooms | 4 Baths | Pool | Two-Car Garage with Guest Suite
Tucked away on a serene and generously sized half-acre parcel, Winds Aloft is an exceptional Nantucket residence that blends timeless design with effortless coastal living.
The open-concept main house features four bedrooms and is filled with natural light, thanks to expansive windows that frame views of the beautifully landscaped yard, vibrant gardens, and inviting swimming pool. Designed with entertaining in mind, the home offers a seamless balance of indoor and outdoor living, with thoughtfully curated spaces that invite connection and relaxation.
A separate two-car garage is enhanced by a fully appointed one-bedroom guest suite above—ideal for extended family, guests, or use as a private home office.
With ample remaining ground cover for future expansion and a premier location offering convenient access to bike paths, pristine beaches, and just .08 miles to the heart of downtown Nantucket, “Winds Aloft” presents a rare opportunity. Whether for personal enjoyment or as a high-performing rental, it offers the perfect combination of lifestyle and long-term value in a sought-after island setting.
William Raveis Nantucket
30 West Sankaty Road
Sconset
$4,995,000
Bed: 5 Bath: 4.5
Designed by Botticelli & Pohl, this beautiful 5-bedroom, 4.5-bath home is ideally located just moments from Sconset Village, the beach, and the Bluff Walk. Set on the corner of West Sankaty Road and Lincoln Street, the property offers three levels of finished living space, including a first-floor guest suite, a custom chef’s kitchen, and a lower level with a gym area and additional guest accommodations. High-end features include hardwood floors throughout, fully tiled bathrooms, a cedar roof, and detailed millwork. Additional amenities include a single-car attached garage with built in storage, off-street parking, and a private fenced in yard. Offered turnkey furnished excluding artwork.
Berkshire Hathaway HomeServices Island Properties Nantucket
1 Brier Patch Road
Quidnet
$3,375,000
Bed: 4 Bath: 3.5
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.
William Raveis Nantucket
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
Exceptional Nantucket Compound with Breathtaking Harbor Views designed by Botticelli & Pohl.
Set high above Pocomo with sweeping views of Polpis Harbor and Nantucket Town beyond, this exceptional five-bedroom, three full and one half bath main house captures the essence of coastal charm and island living. Thoughtfully designed compound for both relaxation and entertaining, the home features traditional first-floor open-concept living with a gourmet kitchen equipped with granite countertops, stainless appliances, a large island, and seamless flow into the dining and living areas.
Two comfortable guest bedrooms on the main level offer privacy and convenience with a shared bath, while the second floor is dedicated to the primary suite and two additional bedrooms with a Jack and Jill bath. The primary bedroom features a serene sitting room, private study, luxurious bath with jacuzzi tub and separate stall shower, and a private deck to take in the panoramic views.
The exterior is just as compelling—anchored by a sparkling private infinity pool and charming cabana with a bedroom studio and full bath. The large, landscaped yard offers peace and privacy with the natural beauty of Nantucket all around.
A rare opportunity to own a stunning island retreat with unforgettable views.
William Raveis Nantucket
2A Forrest Avenue
Mid Island
$2,395,000
Bed: 2 Bath: 2
This unique property offers exceptional versatility and functionality, featuring an oversized three-bay garage is ideal for vehicle storage. Above the garage, you’ll find a spacious 2-bedroom, 2-bathroom apartment with a well-designed layout, perfect for comfortable living. The full basement provides ample storage space and offers potential for future finish-out as additional living area, office space, or recreation room.
This versatile property is ideal for homeowners seeking additional space and functionality, especially for those with residences in Brant Point or in-town locations lacking garage space. This opportunity provides ample room for winter vehicle storage.
Agent is related to seller.
Maury People Sotheby’s International Realty
2B Forrest Avenue
Mid Island
$2,395,000
Bed: 2 Bath: 2
This unique property offers exceptional versatility and functionality, featuring an oversized three-bay garage is ideal for vehicle storage. Above the garage, you’ll find a spacious 2-bedroom, 2-bathroom apartment with a well-designed layout, perfect for comfortable living. The full basement provides ample storage space and offers potential for future finish-out as additional living area, office space, or recreation room.
Agent is related to seller. Seller is a MA licensed real estate broker.
This versatile property is ideal for homeowners seeking additional space and functionality, especially for those with residences in Brant Point or in-town locations lacking garage space. This opportunity provides ample room for winter vehicle storage.
Maury People Sotheby’s International Realty
22 New Street
Town
$3,395,000
Bed: 5 Bath: 3.5
Just moments from the heart of Nantucket town, this beautifully updated antique offers the perfect blend of classic island charm and modern amenities. The main home features 3 bedrooms and 2.5 baths, which could easily function as a year round or summer retreat. A thoughtfully renovated kitchen and primary bedroom anchors the main level, perfect for entertaining and everyday comfort.
Tucked away behind the main residence is a lovely 2-bedroom, 1-bath cottage—ideal for guests, extended family, or rental income. It features its own renovated kitchen and a private deck, creating a serene escape within your own grounds.
Outdoors, the property delights with manicured gardens, stone patios, and quiet spaces to relax or gather. The entire yard was reimagined in 2018, offering a seamless indoor-outdoor lifestyle in a coveted location near shops, restaurants, and island beaches. Complete with an outdoor shower!
Whether you’re seeking a family compound, investment opportunity, or private getaway, this turnkey Nantucket gem has it all.
Seller is a licensed Massachusetts Real Estate agent.
William Raveis Nantucket
115 Surfside Road
Surfside
$8,695,000
Bed: 6 Bath: 8
Spacious, Stylish, and Steps from Surfside Beach
This thoughtfully designed home offers expansive landscaped grounds with a pool, hot tub, and a separate cabana featuring a loft—ideal for guests or added entertaining space. Inside, large windows throughout flood the home with natural light and offer uninterrupted views of the pool and surrounding gardens.
The main living room impresses with a vaulted ceiling, clerestory windows, and a dry-stacked stone fireplace. A true gourmet kitchen is the centerpiece, built for serious cooking and seamless entertaining.
Spread across three levels, the home includes two primary suites—one conveniently located on the main floor—plus a lower-level media and game room. Every room is well proportioned, with quality materials and finishes throughout. The layout is both functional and elegant, with an effortless flow between indoor and outdoor living areas.
A rare combination of space, quality, and location.
Maury People Sotheby’s International Realty
72 Baxter Road
Sconset
$4,300,000
Bed: 4 Bath: 3
Tucked In is a hidden jewel box with four bedrooms and three baths located at the corner of the beautiful Baxter Road and Bayberry Lane. Entering the gate to the flower-filled front yard, the front door welcomes you to the one-floor living/dining/kitchen space with cathedral ceilings. Many windows fill the space with abundant light and allow ocean breezes to cool you in the summer. There is a fireplace to make you cozy on chilly mornings and nights. French doors lead to a dreamy garden in the very private backyard with a swimming pool and guest cottage across the patio. Dine in the garden under the portico. Store your bikes in the garden shed. Enjoy the outdoor shower under the sun. Park two cars in the driveway.
Great Point Properties
3B Park Circle
Mid Island
$1,295,000
Bed: 3 Bath: 2.5
Tucked away and centrally located three bedroom, two and a half bath townhouse with a private outdoor area. The location is ideal for summer or year round living with close proximity to mid-island amenities and south shore beaches, as well as a short distance to town, the bus stop and bike paths. An unfinished basement provides ample room for additional living space if needed. The updated interior is light and bright and ready to be enjoyed by its next owner!
Lee Real Estate
Contact us for more information.