Real estate & homes for sale in Nantucket, MA

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.

A once in a lifetime opportunity to own a bespoke, custom compound on historic Main Street Nantucket. 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.

Stunning and meticulously maintained five-bedroom home on a significantly oversized lot just off Main Street. This proper antique with alluring curb appeal has been fully restored from bottom to top, offering four finished floors of impeccable curation, warm and welcoming spaces for entertaining both inside and out, a state-of-the-art, multi-zoned geothermal heating and cooling system, and flawless attention to every detail. This one-of-a-kind stately and historic offering with double parking areas and room for expansion does not come to market often and is ready for the next mindful steward.

This is an opportunity to own a "like-new home" in the heart of Town. Nestled on Nantucket's iconic Upper Main Street, this stunning Greek Revival home, originally built between 1830-1840, has been exquisitely renovated to blend timeless charm with modern luxury. Nearing the completion of a masterful 6-bedroom, 6-bathroom "back-to-studs" renovation, every detail has been thoughtfully designed to balance classic elegance with contemporary comfort. The light-filled interior seamlessly marries original architectural elements with sleek, high-quality finishes, while the expansive West-facing deck wraps around to a private yard and an enchanting English garden awaiting your personal touch. Complemented by a rare private garage and abundant off-street parking, this property is a true gem in a coveted location. Outfitted with brand-new, top-of-the-line appliances and cutting-edge media, this Nantucket retreat offers the ultimate in modern living within a storied and iconic setting.

WELCOME HOME! No detail has been overlooked in the stunning renovation of this historic house, ideally located in the heart of Nantucket Town. With thoughtful design and the highest standards of construction, this property is poised to endure for the next century and beyond. Spanning over 5,000 square feet across three beautifully finished levels, it boasts multiple living areas, six ensuite bedrooms, exquisite custom cabinetry, paneling, and newly built fireplaces throughout. The top floor features a fully contained suite complete with a living room, a bedroom with a full bath, five ship’s bunks, and second full bath. Enjoy easy access to the roof walk, where you can take in panoramic views of Nantucket Harbor and Coatue. Interior design by Nantucket Looms, this remarkable residence is now ready for occupancy, offered fully furnished.

With a vacation home like this, you’ll never want to leave Nantucket or this house! Recently constructed, you’ll be hard-pressed to find missing amenities in this seven-bedroom, seven-bathroom property sited conveniently near the heart of Town. It offers three finished levels of living space, an in-ground pool with a separate spa, a fire pit, an elevator, and numerous decks and porches. Abutting conservation space and close to Town and nearby beaches, this property provides the ideal locale from which to enjoy endless quality time on your favorite island. With existing leases in place amounting to over $500k in income, this property could also be your next best investment.

Location, Location, Location. Rare opportunity to reimagine the historic, 16 bedroom Ayers Guest House. Transformed in 2000 to house Force 5 Watersports and The Hydrangea Inn, 6 Union Street has become an iconic Downtown landmark. The two attached buildings located a block from Main Street with 8,592 sqft of GLA offer a myriad of mixed-use options .It could also be a great private home.The property has potential for 75% ground coverage. 3,344 sf on ground now. 2,236 sf remaining.

Discover the epitome of luxury living with this stunning home at 10 White Elephant Way, part of the latest White Elephant project. Ideally located in the heart of Nantucket, just across from the White Elephant residences and the renowned Lola 41 restaurant, this home offers unparalleled convenience to all the amenities of Town. Blending historic charm with contemporary elegance, this meticulously designed residence features five bedrooms and an open-plan living area perfect for entertaining. Experience the union of historic charm and modern luxury in this exceptional new home on Nantucket.

Generational Compound opportunity to own 3 contiguous lots, zoned Commercial Neighborhood, with sweeping harbor views, on a private street ¼ mile from town. Assemblage looks over town pier and Francis Street beach kayak rentals, with the soon to be moved Senior Center between it. Great Harbor Yacht Club borders to the East. Rare to see a Commercially zoned, water view, walk to town, with 8600 sq ft of ground cover allowed on 18,723 sq ft of land. Current parcels include a beautiful 4/3.5 main house, a garage with 1 bedroom apartment above it, and two structures to be moved or taken down on independent buildable lots on Union Street side to either merge into a family compound, or develop into a water view hotel by right. Property viewshed already has 14 properties that have been acquired by the town or the Land Bank, with well publicized plans for enhancements.

One Chester Street is an exceptional residence that perfectly blends historic charm with modern luxury. Situated at the edge of Nantucket's historic district where the Cliff area meets Brant Point, this home offers a prime location that provides easy access to the best of island living. This 18th-century ship captain’s home has been meticulously restored, preserving its original details, including five working fireplaces, while integrating contemporary amenities for today's lifestyle. Sold fully furnished with interior design by The Nantucket Looms, the home boasts four levels of living space, with six bedrooms and five and a half baths, it comfortably accommodates large groups, offering ample room for relaxation and privacy. The spacious open kitchen features the original 6' walk-in fireplace, breakfast area, adjoining a bright family/TV room that opens directly onto the rear deck, patio, and garden. The formal dining room features a beautiful lacquered finish. The outdoor space is equally impressive, with a unique artist-built gazebo and fire pit—a perfect spot for evening gatherings. The home’s renovations are top of the line, including all new plumbing, electrical, and HVAC systems, with high-end finishes throughout. The lower level is dedicated to entertainment, with a fully equipped game room including a combination ping pong/pool table, three TVs, a separate seating area, and a kitchenette. For quieter moments, the third-floor guest suite provides access to the roof walk with panoramic views of Nantucket Sound and Harbor, making it a wonderful spot to unwind. One Chester Street is the perfect combination of historic elegance and modern comfort.

Spectacularly reimagined, meticulously renovated, and thoughtfully expanded, this circa-1765 five-bay antique home in the heart of Town has been transformed into a modern masterpiece. Every detail has been carefully considered to achieve a seamless blend of historic character and contemporary luxury, creating a sanctuary that is as timeless as it is exceptional. Thoughtfully designed with an emphasis on natural elements—color, light, and texture—the home blends historic charm with modern tranquility. Every detail showcases pure craftsmanship and attention to detail, brought to life through the collaboration of Coastal Nantucket, Sandcastle Construction, and Jardins International. Positioned on picturesque cobblestone Ash Street, with convenient rear access via Ash Lane, this rare offering is a perfect retreat for those who appreciate exceptional quality and timeless design all in the heart of Town. Access the property from the rear via Ash Lane, where parking for two cars is conveniently provided side by side. From the parking area, enter through a gate that opens to a private side garden, or take the opposite entrance through a charming gated archway, leading to a side patio with expansive Goshen stone and beautifully crafted stone walls, surrounded by lush gardens. Both gardens are bathed in sunlight, offering privacy and stunning landscaping, enhanced by ambient lighting and exquisite stonework. Per ROH zoning, there is just under 500 SF of additional groundcover remaining.

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.

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.

6 Mariner Way stands as one of the island’s only HARBOR VIEW, new construction, turn-key properties with immediate access to both Town and the harbor. Perfectly positioned within Mariner Way, an exclusive enclave of just five luxury residences, this home places you steps from Main Street, the Great Harbor Yacht Club, and the in-town bike path—while offering rare proximity to the pristine creeks of Monomoy, one of Nantucket’s most serene and protected natural settings. This unique shoreline provides harbor access for launching a small boat, stand-up paddleboard, or kayak, with calm waters and a sandy beach—ideal for swimming and enjoying the island lifestyle right outside your door. Boasting five bedrooms and elegant living space this is the perfect backdrop for relaxation and entertaining. This is Nantucket living at its best—new construction, an unbeatable location, and no compromise. 6 Mariner Way is not just a home; it’s an opportunity to own one of the island’s most compelling and complete offerings.

Discover an exceptional lifestyle opportunity with 45 Pleasant Street, where TWO distinct homes in the heart of Town offer modern upgrades and timeless charm. This unique property is designed for those who appreciate both elegance and convenience, providing a seamless blend of residential comfort and investment potential. Imagine the possibilities: whether you're accommodating extended family, choosing to reside in one home while enjoying rental income from the other, or renting both for events like weddings and large gatherings, this property adapts to your vision. Thoughtfully renovated in 2016, both residences seamlessly blend historic charm with modern living. Recent upgrades, including a new roof and copper gutters installed in 2022, ensure durability and aesthetic appeal. With new central HVAC units and hot water tanks also added in 2022, these homes offer a worry-free and energy-efficient living experience. The property's prime location, just steps away from Main Street, enhances its appeal, promising a vibrant lifestyle with easy access to shops, dining, and community events. The spacious back patios are perfect for outdoor gatherings, making entertaining a delight. Offered fully furnished, this property is the epitome of a turn-key rental investment. With a proven rental history generating over $300k and with over $345k already secured for 2025, it stands as a testament to its desirability and income potential. Step into a lifestyle of convenience and sophistication with 45 Pleasant Street, where the charm of Town living meets the ease of rental income. Don’t miss this chance to own a piece of history and a future of possibilities.

2 Mariner Way stands as one of the island’s only new construction, turn-key properties with immediate access to both Town and the harbor. Perfectly positioned within Mariner Way, an exclusive enclave of just five luxury residences, this home places you steps from Main Street, the Great Harbor Yacht Club, and the in-town bike path—while offering rare proximity to the pristine creeks of Monomoy, one of Nantucket’s most serene and protected natural settings. This unique shoreline provides harbor access for launching a small boat, stand-up paddleboard, or kayak, with calm waters and a sandy beach—ideal for swimming and enjoying the island lifestyle right outside your door. Inside, the floor plan delivers with an expansive open-concept kitchen, living, and dining area complete with a custom bar, and a first-floor suite. The second level features a luxurious primary suite, two additional en-suite bedrooms, and a secondary living room. This is Nantucket living at its best—new construction, an unbeatable location, and no compromise. 2 Mariner Way is not just a home; it’s an opportunity to own one of the island’s most compelling and complete offerings.

Modern Elegance in the Heart of Historic Nantucket. Located on picturesque Candle House Lane this newly constructed home is thoughtfully designed across three finished levels. The residence features five bedrooms, five bathrooms, and two half baths, offering spacious and beautifully detailed interiors. Now being offered furnished, the home is ready for effortless coastal living. Perfect for both everyday comfort and entertaining, the property includes a private outdoor space with a deck, patio, and outdoor shower and a beautiful brick driveway accommodating 2 cars. Every detail—from the curated finishes to the inviting layout—has been carefully selected to create a residence that is as functional as it is refined.

This newly constructed home at 22 Vestal Street is perfectly positioned in town proper, just a short distance from historic downtown Nantucket and the island’s pristine beaches. Built by one of Nantucket’s premier builders, this stunning residence spans over 4,000 square feet and features six bedrooms and four-and-a-half baths. Designed and styled by LTW Design, the home offers a sophisticated yet functional living space, ideal for families and friends to create lasting summer memories. An open floor plan seamlessly blends indoor and outdoor living, featuring a gourmet kitchen with top-of-the-line appliances, stone countertops, and wide-plank oak floors throughout. Additional highlights include a masonry fireplace, contemporary tile and lighting fixtures, and beautifully manicured landscaping, all thoughtfully curated to enhance this exceptional island retreat.

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!

Four sunset hill is a home that breathes history tucked into the heart of Nantucket town and perched on a high point. This home tells the story of a full scale renovation where heritage meet soft, sculptural finishes, and history holds hands with modern ease. Restored with a fabulous floor plan incorporating an open living concept, 5 bedrooms, 5 ensuite baths, and several living areas to enjoy mornings lit by salt air and afternooons that harness the western sunset skies. Not to be missed; the 7 window sun porch, cozy and private den with gas fireplace, custom built-ins throughout infusing every space with warmth and intention. High level elements include gorgeous marble tile baths and stunning custom cabinetry. Offered turn-key and fully furnished this property ultimately provides for quiet luxury, tailored textures, and the effortless comfort of knowing everything is exactly where it should be. Not to mention that you can pop out your front door and only a short jaunt away you will find the best shopping, Nantucket's finest resaurants, and premier beaches.

Authentic historic restoration in 2024 of a 1790 home with arguably one of the best expansive views of the Lily Pond. History and the 21st century blend together to create a unique offering. Originally the 1790 Coopers shed used to make the rims for whale oil barrels and subsequent 1800 addition is transformed into a 4 bedroom, 4 en-suite bath home. A large deck has peaceful views of the Lily Pond. The original beams, floors, windows have all been refurbished, the walls plastered and hardware updated. 27 North Liberty was the winner of this year's 2024 historical renovation award, presented by the Nantucket Preservation Trust. Designed garage with studio above currently pending HDC approval.

"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 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.

This beautifully restored and well-maintained federal-style home from the 1830s, located on historic Orange Street, offers a perfect blend of antique charm and modern comforts. It's an ideal property for someone who values both historical character and contemporary upgrades. The home features three finished levels of living space with four bedrooms and four-and-a-half baths. Additionally, it boasts meticulously cared-for gardens, stone walls and a patio area for seating, offering both functional living space and outdoor enjoyment. The home is complete with historic details such as 6 working fireplaces, uncommonly high ceilings, classic mortgage button in newel post and NHC designated exterior plaque.

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.

2 charming and sophisticated cottages (4 bedrooms total) side by side with harbor views that provide a wonderful opportunity for a variety of uses. Ideal as a family compound for multi-generations or use one and rent the other. Located in the heart of Nantucket's historic village, one block from the harborfront with its sandy beach and a moment's walk to Main Street. Featuring off-street parking, high end appliances, central A/C, beautiful furnishings and top of the line finishes including walnut trim, quartz counter tops and ship lap paneling throughout. Approximate 300 sf ground cover remaining in each unit. Unit D is available for separate purchase at $2,895,000.

Built in 1831 by Philip Folger, 19 Orange Street is the gracious center residence in the Folger Row House Block. Exquisitely renovated to embrace its historic architecture, this sophisticated home features three levels of living space highlighted by two elegant parlors with fireplaces, formal dining room, kitchen, four bedrooms, 3.5 baths, and a small office. The magical and private courtyard garden, walled on two sides, features espaliered pear and apple trees, roses and a rose covered pergola. Original architectural details include wide pine floors, crown molding, carved fireplace mantels and arched bookcases, carved newel post, beveled glass picket doors separating the two parlors and five fireplaces. One car parking at rear of house.

Three bedroom antique home and garage nestled between West Chester Street and Sunset Hill Road. Set on an oversized lot this property has almost 2,000 square feet of remaining ground cover. Near Lily Pond Park and the Oldest House, it offers a level of privacy that is rare for properties in the Residential Old Historic District. The house is located within the highest portion of the lot, approximately 40 feet, along Sunset Hill Road, offering a nice view toward Lily Pond Park. The garage is situated just off West Chester at approximately 20 feet.

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.

Originally built in 1761 in the old town of Sherburne, The Thomas Starbuck House found its new home at 11 Milk Street in 1790. 11 Milk Street is a beautifully restored Quaker-style home that blends historic charm with modern comforts. Ideally situated in a prime location, this turnkey residence offers four bedrooms, three full baths, and one-half bath. The light-filled kitchen is a true standout, featuring a wet bar, pantry, and ample storage—perfect for both everyday living and entertaining. Many of the home’s original details, including an inglenook fireplace and pine floors, have been thoughtfully preserved, creating a warm and inviting atmosphere. The outdoor space includes a private patio and parking space, making this historic gem as functional as it is charming.

15 Old North Wharf, a comfortable 2 bedroom cottage, is on the residential oasis of Old North Wharf. It enjoys beautiful harbor views looking across a lawn to Easy Street boat basin. This is a rare opportunity to own an in town hideaway steps from Main Street.

Tucked away on a quiet side street just moments from the heart of downtown Nantucket, this well maintained four-bedroom, three-bath Federal style home blends historic charm with modern comfort. Sunlight pours through numerous windows and glass doors, creating a seamless indoor-outdoor connection to the deck and stone patio. Six fireplaces, original wood floors, and preserved architectural details speak to its rich history, while central air conditioning and off-street parking provide contemporary convenience. A true gem in an unbeatable location.

Antique house located in the Residential Old Historic District of Town with four+ bedrooms and 3.5 baths. Historic details intact, six fireplaces, raised panelling, original doors and wide pine floors throughout. Patio, off-street parking, large easily accessed shed and potential for expansion on spacious third floor. Excellent location, close to all that Town has to offer. New cedar roof, interior and exterior painting and oil tanks. Furnished and ready for summer occupancy.