5-Bedroom Homes for Sale in Nantucket, MA

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  /5

  $34,500,000

  • 10 Beds
  • 9 Baths
  • 6,875 Sq Ft

  52 Monomoy Rd, Nantucket, MA 02554

  Commanding one of the most coveted harborfront locations on Nantucket, this extraordinary 1.25-acre estate offers truly unparalleled harborfront views and an unmatched coastal living experience. With sweeping, panoramic vistas stretching from Town across the harbor to Brant Point and Coatue, the property delivers a front-row seat to the island’s most iconic scenery. Enjoy sunsets over the water,

  

  Morgan Winn

  Maury People Sotheby's International Realty

  (508) 731-3567

  52 Monomoy Rd, Nantucket, MA 02554
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  /62

  $9,995,000

  • 9 Beds
  • 10 Baths
  • 6,072 Sq Ft

  21 Quidnet Rd, Nantucket, MA 02554

  Located in one of the most desirable areas of Nantucket, this 3.78 acre estate has it all! Welcome to High Point where two impeccably designed homes seamlessly blend classic architectural details with the sophistication of new construction. Thoughtfully crafted to enhance both everyday comfort and effortless entertaining.Step into sun-drenched interiors anchored by designer chef’s kitchens

  

  Morgan Winn

  Maury People Sotheby's International Realty

  (508) 978-6129

  21 Quidnet Rd, Nantucket, MA 02554
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  /48

  $11,995,000

  • 5 Beds
  • 4.5 Baths
  • 3,344 Sq Ft

  20 N Pasture Ln, Nantucket, MA 02554

  Welcome to 20 North Pasture Lane, a stunningly reimagined estate nestled in the serene Polpis area of Nantucket. Set on 2.75 acres bordering conservation land, this beautifully renovated home offers views of Polpis Harbor and the quiet privacy of one of the island’s most peaceful neighborhoods. In 2024, the property underwent a full, top-to-bottom renovation, enhancing every inch with thoughtful

  

  Morgan Winn

  Maury People Sotheby's International Realty

  (508) 545-9673

  20 N Pasture Ln, Nantucket, MA 02554
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  /56

  $6,995,000

  • 5 Beds
  • 4 Baths
  • 2,388 Sq Ft

  56 Meadow View Dr, Nantucket, MA 02554

  This exquisite hidden gem, surrounded by breathtaking landscaping, offers a serene retreat for your Nantucket dream home. Ideally situated just 1.5 miles from the ferry docks and a half-mile from Nantucket Town's Historic District in the charming Hussey Farm neighborhood, this location provides effortless access to the island’s renowned restaurants, boutiques, and beaches—while ensuring complete

  

  Morgan Winn

  Maury People Sotheby's International Realty

  (508) 593-9769

  56 Meadow View Dr, Nantucket, MA 02554
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  /47

  $17,750,000

  • 6 Beds
  • 5.5 Baths
  • 4,299 Sq Ft

  113 Eel Point Rd, Nantucket, MA 02554

  Welcome to your dream beachfront home! This stunning property features an expansive open-concept living space that seamlessly integrates the kitchen, dining, and living areas, perfect for both entertaining and relaxing. Elegant French doors open to a generous patio with direct access to a private walkway leading to the beach, offering unparalleled views and immediate access to the oceanfront. The

  

  Morgan Winn

  Maury People Sotheby's International Realty

  (508) 719-9965

  113 Eel Point Rd, Nantucket, MA 02554
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  /36

  $7,200,000

  • 5 Beds
  • 8 Baths
  • 4,352 Sq Ft

  2 Old Mill Ct, Nantucket, MA 02554

  Experience the best of summer living on Nantucket with this custom-built five-bedroom home, completely turnkey, close to Town, and available for immediate occupancy. Thoughtfully designed and offered fully furnished, in part by Nantucket Looms, this home features five bedrooms and over 4,300 square feet of living space on three levels. Featuring open concept living/dining/kitchen, as well as a

  Ethan Ulmer Great Point Properties

  2 Old Mill Ct, Nantucket, MA 02554
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  /40

  $11,500,000

  • 6 Beds
  • 7.5 Baths
  • 6,635 Sq Ft

  42 Main St, Nantucket, MA 02564

  Aptly named 'Time Out', this private Sconset Estate with an exquisite five bedroom main house, one bedroom guest house, heated pool and over sized garage is a summer oasis! The property is completely hedged in, abuts acres and acres of Nantucket Conservation Foundation open space and is set back from the street, with mature plantings and a lovely front and rear yard, affording much privacy.

  Jeanne Hicks Lee Real Estate

  42 Main St, Nantucket, MA 02564
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  /11

  $14,500,000

  • 8 Beds
  • 11 Baths
  • 7,653 Sq Ft

  17 Pilgrim Rd, Nantucket, MA 02554

  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

  Brian Fox Hanley Garrette Group LLC

  17 Pilgrim Rd, Nantucket, MA 02554
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  /24

  $10,995,000

  • 8 Beds
  • 10 Baths
  • 6,548 Sq Ft

  12 Derrymore Rd, Nantucket, MA 02554

  Nantucket traditional on the outside meets modern luxury on the inside in this fantastic new build, by Robert Alves of Island Construction LLC, offering a six-bedroom main home, two-bedroom cottage with a garage in the sought-after Cliff area of Nantucket Island, a short distance from North Shore beaches and the historic downtown Nantucket. This home offers spacious, airy living spaces with a

  Dawn Hill Holdgate Great Point Properties

  12 Derrymore Rd, Nantucket, MA 02554
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  /7

  $12,450,000

  • 5 Beds
  • 6.5 Baths
  • 6,951 Sq Ft

  85 Vestal St, Nantucket, MA 02554

  Exceptional Estate-Ready Offering at 85 Vestal Street, NantucketHDC-Approved Compound with Pool, Studio, Cabana & More, June 2026 Occupancy.Ideally located just west of town, this spacious half-acre parcel - offering a seamless path to high-end Nantucket living.Development includes-A gracefully designed main residence with five bedrooms, five full and one half baths,

  Michele Kelsey William Raveis Nantucket

  85 Vestal St, Nantucket, MA 02554
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  /39

  $7,995,000

  • 5 Beds
  • 7 Baths
  • 3,783 Sq Ft

  4 Mariner Way, Nantucket, MA 02554

  4 Mariner Way presents a rare opportunity to own a newly built, expertly designed four-bedroom main residence with a separate one-bedroom guest house offering water views—all in the heart of historic Nantucket. Located within an exclusive enclave of just five homes, this property provides convenient access to Main Street, the Great Harbor Yacht Club, Monomoy’s scenic creeks, and the in-town bike

  Bernadette Meyer Maury People Sotheby's International Realty

  4 Mariner Way, Nantucket, MA 02554
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  /79

  $7,995,000

  • 5 Beds
  • 4 Baths
  • 3,580 Sq Ft

  1 W Sankaty Rd, Nantucket, MA 02554

  Located on the idyllic, tree-lined Main Street in Sconset, this timeless white clapboard residence blends historic charm with contemporary living. Originally built in 1820 and thoughtfully renovated in 2025, this exceptional home now offers a total of 5 bedrooms and 4 bathrooms — ideal for comfortable family living and effortless entertaining. Step inside to discover multiple spacious living

  Chandra Miller Maury People Sotheby's International Realty

  1 W Sankaty Rd, Nantucket, MA 02554
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  /37

  $7,495,000

  • 5 Beds
  • 5.5 Baths
  • 3,354 Sq Ft

  39 Chuck Hollow Rd, Nantucket, MA 02554

  Perched on an expansive 1.51-acre lot in Tom Nevers, every inch of this newly constructed 5-bedroom, 5.5-bathroom retreat is thoughtfully curated to offer both aesthetic excellence and functional luxury—with sweeping second-floor water views and expansive indoor & outdoor living including a private backyard oasis complete with 16x32 gunite pool, 10x10 spa with waterfall, gas firepit and Lynx

  Chandra Miller Maury People Sotheby's International Realty

  39 Chuck Hollow Rd, Nantucket, MA 02554
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  /55

  $8,695,000

  • 6 Beds
  • 9 Baths
  • 5,700 Sq Ft

  115 Surfside Rd, Nantucket, MA 02554

  Spacious, Stylish, and Steps from Surfside BeachThis 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

  Lucie Cristler Maury People Sotheby's International Realty

  115 Surfside Rd, Nantucket, MA 02554
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  /9

  $7,495,000

  • 8 Beds
  • 10 Baths
  • 5,264 Sq Ft

  10 Silver St, Nantucket, MA 02554

  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

  Chandra Miller Maury People Sotheby's International Realty

  10 Silver St, Nantucket, MA 02554
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  /31

  $14,950,000

  • 8 Beds
  • 8 Baths
  • 7,509 Sq Ft

  4 Shawkemo Hills Ln, Nantucket, MA 02554

  Nestled on 2.39 acres in a coveted location on Nantucket, this exceptional five-bedroom, four-full-bath, two-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. Boasting soaring ceilings, abundant natural

  Brian Sullivan Fisher Real Estate

  4 Shawkemo Hills Ln, Nantucket, MA 02554
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  /83

  $7,500,000

  • 7 Beds
  • 5 Baths
  • 3,459 Sq Ft

  45 Brewster Rd, Nantucket, MA 02554

  A RARE and SPECIAL Nantucket Experience awaits you in Monomoy! Tucked behind a tall privet hedge graced with a garden gate lies a serene private oasis. The stunning gardens, mature trees and plantings, thoughtfully manicured lawn and sparkling in-ground pool provide a setting that invites one to experience tranquility, calm and the desire to breathe deeply. With over 1.2 acres (which abut the

  Shellie Dunlap Lee Real Estate

  45 Brewster Rd, Nantucket, MA 02554
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  /39

  $7,225,000

  • 5 Beds
  • 5.5 Baths
  • 3,024 Sq Ft

  6 Mariner Way, Nantucket, MA 02554

  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

  Bernadette Meyer Maury People Sotheby's International Realty

  6 Mariner Way, Nantucket, MA 02554
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  /54

  $8,900,000

  • 5 Beds
  • 7 Baths
  • 6,072 Sq Ft

  2 A Morgan Square, Nantucket, MA 02554

  Located in coveted Surfside and just a quarter-mile from the stunning South Shore beaches, 2A Morgan Sq offers hard to find privacy. Built in 2019 by Bessey Construction, this property spans just under an acre and includes a main house featuring 5 bedrooms and 5.5 baths with over over 5,300 square feet of beautifully appointed living space. Additional amenities include a two-car garage with a

  Chris Kling J Pepper Frazier Co.

  2 A Morgan Square, Nantucket, MA 02554
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  /62

  $8,795,000

  • 5 Beds
  • 7 Baths
  • 4,024 Sq Ft

  4 Westerwick Dr, Nantucket, MA 02564

  No detail has been overlooked in this one of a kind custom newly built five bedroom, four full and three half bath home in Sconset. This property offers privacy while still being close to the quaint Sconset village, restaurants and beaches. The creative intention and thoughtfulness that has gone into each special space of this home is evident from the moment you step into the property. Each

  John Arena William Raveis Nantucket

  4 Westerwick Dr, Nantucket, MA 02564
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  /62

  $7,700,000

  • 5 Beds
  • 7 Baths
  • 3,600 Sq Ft

  8 Chuck Hollow Rd, Nantucket, MA 02554

  Sitting in the serene environment of Tom Nevers East, "Wildflowers" boasts a perfect blend of comfort and luxury. Newly renovated in 2024, each of the four spacious bedrooms in the main house is a private retreat, complete with their own en-suite bathrooms. A gourmet kitchen opens to the dining room and living room with vaulted ceilings. French doors from the dining area lead out to an expansive

  Marybeth Gibson Maury People Sotheby's International Realty

  8 Chuck Hollow Rd, Nantucket, MA 02554
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  /58

  $7,995,000

  • 7 Beds
  • 10 Baths
  • 5,958 Sq Ft

  17 Cannonbury Ln, Nantucket, MA 02554

  17 Cannonbury Lane captures the spirit of a quintessential Nantucket summer—just moments from the beach and a short bike ride to the charm of ’Sconset Village. Morning dips in the Atlantic, ice cream runs to the market, fresh flowers from the community garden, and evenings at The Summer House—all just steps from your door.Tucked into the desirable Cannonbury Lane neighborhood, this

  Bernadette Meyer Maury People Sotheby's International Realty

  17 Cannonbury Ln, Nantucket, MA 02554
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  /53

  $7,995,000

  • 6 Beds
  • 6.5 Baths
  • 2,940 Sq Ft

  45 Easton St, Nantucket, MA 02554

  Situated in stunning Brant Point, this idyllic area boasts picturesque harbor views and is conveniently located across from the iconic White Elephant and next to downtown Nantucket. Both the main house and adjacent cottage are beautifully renovated blending classic Nantucket charm with modern design. The main house is four bedrooms with en-suite baths plus mudroom and powder room and a surprise

  Ty Costa William Raveis Nantucket

  45 Easton St, Nantucket, MA 02554
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  /43

  $7,995,000

  • 6 Beds
  • 6.5 Baths
  • 2,940 Sq Ft

  45 Easton St, Nantucket, MA 02554

  Located front and center in desirable Brant Point. The house and cottage have been meticulously renovated with a modern layout that pairs well thought out spaces with clean lines. Bright light sweeps through the open floor plan playing off the ship lap walls, white rhino marble countertops and solid Vermont Oak floors. The main house features five en suite bedrooms and the sweet but sophisticated

  J Pepper Frazier II J Pepper Frazier Co.

  45 Easton St, Nantucket, MA 02554
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  /15

  $6,950,000

  • 5 Beds
  • 7 Baths
  • 4,112 Sq Ft

  6 Packet Dr, Nantucket, MA 02554

  LAID-BACK LUXURY FOR SUMMER 2025 AWAITS! Tucked away in 'Sconset on a private cul de sac, 6 Packet Drive is turnkey perfection blending classic Nantucket charm with modern sophistication. Built by Chris O’Connell with exceptional craftsmanship, this stunning home features high-quality finishes and fixtures throughout all rooms and baths, including top-tier appliances in a chef’s kitchen replete

  Marybeth Gilmartin-Baugher Compass MA LLC

  6 Packet Dr, Nantucket, MA 02554
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  /67

  $7,995,000

  • 5 Beds
  • 5.5 Baths
  • 6,000 Sq Ft

  12 Upper Tawpawshaw Rd, Nantucket, MA 02554

  Privately nestled at the end of a cul de sac, abutting hundreds of acres of conservation land, laced with walking trails, sits this spectacular family retreat. Exquisitely designed by Shelter 7 and meticulously executed in 2022 by a skilled team of local craftsmen, the 5-bedroom, 6,000 sf property offers the highest quality finish details, state-of-the-art amenities, and wonderful outdoor

  Jim Houghton William Raveis Nantucket

  12 Upper Tawpawshaw Rd, Nantucket, MA 02554
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  /66

  $8,750,000

  • 6 Beds
  • 5.5 Baths
  • 5,101 Sq Ft

  1 Chester St, Nantucket, MA 02554

  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,

  Robert Young William Raveis Nantucket

  1 Chester St, Nantucket, MA 02554
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  /30

  $7,000,000

  • 6 Beds
  • 4.5 Baths
  • 3,699 Sq Ft

  60 Cliff Rd, Nantucket, MA 02554

  Ideally situated, this well-maintained six-bedroom, four-and-a-half-bath home with an attached studio and garage is set back from Cliff Road on a significantly sized double lot allowing for potential subdivision or expansion. The convenient location of 60 Cliff provides access to Steps Beach, the Westmoor Club, and the historic Town of Nantucket. The first floor features a beautifully updated

  Greg McKechnie Great Point Properties

  60 Cliff Rd, Nantucket, MA 02554
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  /65

  $8,795,000

  • 6 Beds
  • 8 Baths
  • 4,437 Sq Ft

  2 Hedgebury Ln, Nantucket, MA 02554

  Oasis nestled on the outskirts of town... this unique compound offers a perfect blend of privacy and convenience, just a short distance from upper Main Street. The property includes a comfortable four bedroom main house, a charming 2-bedroom cottage, and a host of outdoor amenities perfect for both relaxation and entertaining. The main house features an open first floor layout, first and second

  John Arena William Raveis Nantucket

  2 Hedgebury Ln, Nantucket, MA 02554
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  /35

  $7,995,000

  • 5 Beds
  • 3.5 Baths
  • 3,454 Sq Ft

  2 Shore Rd, Nantucket, MA 02554

  Generational Compound opportunity to own 2 contiguous lots, zoned Commercial Neighborhood, with sweeping harbor views, on a private street 1⁄4 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

  Ty Costa William Raveis Nantucket

  2 Shore Rd, Nantucket, MA 02554
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  /64

  $6,595,000

  • 5 Beds
  • 6.5 Baths
  • 3,347 Sq Ft

  4 Crown Ct, Nantucket, MA 02554

  Perched on highly sought after Academy Hill, one of Nantucket's most desirable and historic neighborhoods. 4 Crown Court is a gracious 5 bedroom, 6.5 bath home offering timeless island living just steps from Main Street. Thoughtfully designed for both comfort and function, the home features 3 fireplaces-One in the cozy den, the dining room and the primary suite's private living room with private

  Daniel Barber Maury People Sotheby's International Realty

  4 Crown Ct, Nantucket, MA 02554
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  /59

  $5,800,000

  • 8 Beds
  • 10 Baths
  • 4,761 Sq Ft

  12 & 13 Shimmo Pond Rd, Nantucket, MA 02554

  SHIMMO: Charming 4-Bedroom Home with 2-Bedroom Cottage on expansive grounds in the coveted Shimmo locale.Shimmo Pond Road, where sandy paths wind beneath leafy canopies and Nantucket Harbor beckons in the distance- this exceptional property captures the timeless charm of a countryside residence. Set on an oversized and private parcel, the beautifully proportioned 4-bedroom main house is

  Sheila Carroll Maury People Sotheby's International Realty

  12 & 13 Shimmo Pond Rd, Nantucket, MA 02554
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  /16

  $2,700,000

  • 6 Beds
  • 6 Baths
  • 4,644 Sq Ft

  20 Pine Grove Ln, Nantucket, MA 02554

  Great opportunity for investment or employee housing all new shingles side and roof and new windows. gas heat all metered separate both electric and gas. This is a side by side duplex. Both sides have a first floor bedroom, kitchen, dining and living room.full bath/laundry room. Second floor has two bedrooms and a hall full bath. Both duplexes have separate full lower level living areas and

  Robert F Egan J Pepper Frazier Co.

  20 Pine Grove Ln, Nantucket, MA 02554
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  /62

  $6,795,000

  • 5 Beds
  • 5.5 Baths
  • 3,937 Sq Ft

  55 Orange St, Nantucket, MA 02554

  A piece of history tailored for today's living. This exquisitely restored 1824 four-bay home, built by Captain John C. Gardner, invites us to appreciate an antique gem. A rich texture of history blends seamlessly with elevated updates and modern amenities across four finished levels. It's a joy to experience a classic Nantucket house with refined interiors and two-car off-street parking. Of

  Carolyn Durand Lee Real Estate

  55 Orange St, Nantucket, MA 02554
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  /42

  $2,345,000 Open Sat 10AM - 11AM

  • 5 Beds
  • 4.5 Baths
  • 3,700 Sq Ft

  25 Beach Grass Rd, Nantucket, MA 02554

  Stunning new construction Colonial offering 5 beds and 4.5 baths with exceptional design and flow. The main floor features a primary suite with a luxurious en suite bath, mudroom, and an open-concept layout with a chef’s kitchen, quartz island, and high-end appliances that opens to a spacious family room with double sliders. Upstairs offers three bedrooms, including a second primary suite. The

  Louise Touchette Coldwell Banker Realty - Lynnfield

  25 Beach Grass Rd, Nantucket, MA 02554
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  /29

  $2,895,000

  • 5 Beds
  • 3.5 Baths
  • 2,412 Sq Ft

  19 Cato Ln, Nantucket, MA 02554

  SHOWINGS TO BEGIN AFTER JULY 15TH ... OPEN HOUSE JULY 17TH. This charming and comfortable three bedroom home with an attached two bedroom apartment above the two car garage is ideally located on a spacious half acre lot that offers mature landscaping, a fabulous private back and side yard, living and entertaining areas including a large stone patio, and plenty of parking. Moments to Town, Cisco,

  Jenny Paradis & Roberta White Maury People Sotheby's International Realty

  19 Cato Ln, Nantucket, MA 02554
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  /31

  $4,650,000

  • 7 Beds
  • 4.5 Baths
  • 2,527 Sq Ft

  8 Pitman Rd, Nantucket, MA 02554

  Tucked away on a quiet, charming private lane in the heart of Sconset Village, this exceptional property captures the timeless beauty and simplicity of 'Sconset living. Just moments from the iconic Sconset Bluff Walk and the beach, this cherished summer cottage is nestled on nearly an acre of serene, untouched land—surrounded by mature trees, lush ferns, and thoughtfully planted gardens that

  Chandra Miller Maury People Sotheby's International Realty

  8 Pitman Rd, Nantucket, MA 02554
• 

  

  /27

  $6,495,000

  • 5 Beds
  • 4.5 Baths
  • 3,742 Sq Ft

  2 Shore Rd, Nantucket, MA 02554

  A truly rare opportunity to own a harbor-view property with unmatched development potential — 2 Shore Rd lot is 11,484 ft, 50% ground cover by right for 5 years from purchase (grandfathered from CN conversion). That equates to 5,742 sq ft of buildable ground cover — a scope nearly impossible to find this close to Town, with direct harbor views.The property currently includes:Main

  Ty Costa William Raveis Nantucket

  2 Shore Rd, Nantucket, MA 02554
• 

  

  /64

  $6,195,000

  • 5 Beds
  • 4.5 Baths
  • 4,861 Sq Ft

  5 Upper Tawpawshaw Rd, Nantucket, MA 02554

  Welcome to "Edgemoor", a private island retreat nestled on a quiet cul de sac in Nantucket. This beautifully appointed 5 bedroom residence combines timeless charm with modern amenities, set on a generous lot abutting hundreds of acres of protected conservation land with direct access to walking paths from your own backyard. Natural light pours in the window-filled, designer decorated, living

  Daniel Barber Maury People Sotheby's International Realty

  5 Upper Tawpawshaw Rd, Nantucket, MA 02554
• 

  

  /55

  $3,950,000

  • 6 Beds
  • 5.5 Baths
  • 4,763 Sq Ft

  12 Longwood Dr, Nantucket, MA 02554

  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

  Robert Young William Raveis Nantucket

  12 Longwood Dr, Nantucket, MA 02554

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