5-Bedroom Homes for Sale in Nantucket County MA

/38
$5,775,000
- 5 Beds
- 5 Baths
- 2,212 Sq Ft
24 Meadow View Dr, Nantucket, MA 02554

Nestled in the desirable Hussey Farm neighborhood, this total reconstruction offers the perfect balance of modern luxury and classic Nantucket charm. Featuring 5 bedrooms and 5 bathrooms, the residence is designed for both comfort and entertaining, with meticulous craftsmanship throughout.Step outside to your private pool, a spacious porch, and an inviting outdoor dining area, creating

Morgan Winn

Maury People Sotheby's International Realty

(508) 715-9351

24 Meadow View Dr, Nantucket, MA 02554
/65
$26,850,000
- 8 Beds
- 10 Baths
- 12,096 Sq Ft
37 Sankaty Head Rd, Nantucket, MA 02554

Commanding a presence high on the Sconset Bluff, this private family compound is inarguably one of the most stunning properties on Nantucket. Sited so as to enjoy sweeping, unobstructed views of the Atlantic Ocean, Sesachacha Pond, and Sankaty Light, the 6-acre estate includes a 12,000 square foot main residence, a 2 bedroom guest house, and a water feature. This water feature is unmatched with a

Morgan Winn

Maury People Sotheby's International Realty

(508) 682-5389

37 Sankaty Head Rd, Nantucket, MA 02554
/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
/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
/48
$10,995,000
- 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
/56
$6,495,000
- 5 Beds
- 4 Baths
- 2,388 Sq Ft
54 & 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) 718-2136

54 & 56 Meadow View Dr, Nantucket, MA 02554
/3
$10,995,000
- 7 Beds
- 8.5 Baths
- 6,586 Sq Ft
7 Moors End Ln, Nantucket, MA 02554

Tucked at the end of a quiet cul-de-sac in Polpis, just five minutes from two pristine beaches, this brand-new, three-level residence offers the ultimate in modern coastal luxury. Designed for gathering and entertaining, the home spans 7 bedrooms, 7.5 baths, three distinct living rooms, each balancing elegance with ease.At the heart of the home, a gourmet kitchen with a spacious island

Chandra Miller Maury People Sotheby's International Realty

7 Moors End Ln, Nantucket, MA 02554
/20
$10,995,000
- 9 Beds
- 7.5 Baths
- 6,750 Sq Ft
85 Orange St, Nantucket, MA 02554

An exceptional in-town compound with limitless possibilities.Set on two lots of record with approved subdivision potential, this thoughtfully designed property offers a rare combination of new construction, historic charm, and income-producing potential all just moments from downtown Nantucket and the Great Harbor Yacht Club.The main residence, a spacious 5-bedroom, 4.5-bath home by

Michele Kelsey William Raveis Nantucket

85 Orange St, Nantucket, MA 02554
/46
$13,995,000
- 5 Beds
- 5 Baths
- 4,224 Sq Ft
105 Low Beach Rd, Nantucket, MA 02554

Private. Peaceful. Pristine. Set on over 6 acres at the end of Low Beach, sits this ultimate retreat. This property enjoys breathtaking views over sand dunes to the ocean beyond, Tom Nevers pond and backs up to 300+ acres of conservation land. Sit on the front porch and take in the sea breeze and calming sounds of the pond and ocean, or relax out back in the private outdoor pool and outdoor

John Arena William Raveis Nantucket

105 Low Beach Rd, Nantucket, MA 02554
/52
$7,495,000
- 6 Beds
- 5.5 Baths
- 4,930 Sq Ft
18 Mill St, Nantucket, MA 02554

A unique offering for in-town living, this well-crafted home blends convenience with quality. The property features three floors of living in the spacious main house, along with a separate studio, a shed, and coveted two-car parking. Outdoor living is exceptional, with a covered porch, outdoor kitchen, gas fireplace, and multiple seating areas for entertaining or relaxing. Inside, timeless

Bernadette Meyer Maury People Sotheby's International Realty

18 Mill St, Nantucket, MA 02554
/48
$8,250,000
- 6 Beds
- 5.5 Baths
- 3,532 Sq Ft
26 Old Tom Nevers Rd, Nantucket, MA 02554

Escape to your private oasis on Nantucket Island. This exceptional property offers the ultimate coastal lifestyle, featuring a stunning upside-down main house, a newly built guest cottage, and a serene, secluded pool—all just steps from the beach. The main house boasts approximately 3,000 square feet of exquisitely finished living space, including four spacious bedrooms, four full bathrooms, and

Chris Kling J Pepper Frazier Co.

26 Old Tom Nevers Rd, Nantucket, MA 02554
/41
$8,495,000
- 8 Beds
- 6 Baths
- 3,814 Sq Ft
42 Chuck Hollow Rd, Nantucket, MA 02554

Situated in Tom Nevers East, just minutes from the Nantucket Golf Club and the village of Sconset, Hollyhock is a five-bedroom residence accompanied by a three-bedroom guest cottage, all set on three rolling acres that offer exceptional privacy, high elevations, and sweeping views from both floors of the Atlantic Ocean, conservation land, and Tom Nevers Pond. Originally constructed in Hanover,

Peter Engen Lee Real Estate

42 Chuck Hollow Rd, Nantucket, MA 02554
/24
$7,995,000
- 5 Beds
- 7 Baths
- 5,600 Sq Ft
36 W Chester St, Nantucket, MA 02554

Anchored between Main Street and Steps Beach, this extraordinary home captures the essence of refined coastal living. Five private ensuite bedrooms provide luxurious comfort for family and guests, while the chef’s kitchen and adjoining dining room invite gatherings both large and intimate. The sun-soaked, south-facing deck extends the living space into a private, landscaped yard, where views of

Jennifer Shalley Allen Fisher Real Estate

36 W Chester St, Nantucket, MA 02554
/53
$9,500,000
- 5 Beds
- 8 Baths
- 5,394 Sq Ft
32 India St, Nantucket, MA 02554

Originally built in the 1800s, this exceptional property has been masterfully reimagined through the collaborative efforts of Main Street Construction and Mark Cutone Architecture. The result is a seamless fusion of historic preservation and modern luxury. Located just moments from Main Street in the heart of Nantucket’s historic district, the home’s front facade maintains its timeless charm,

Robert Young William Raveis Nantucket

32 India St, Nantucket, MA 02554
/35
$7,999,995
- 5 Beds
- 4.5 Baths
- 3,788 Sq Ft
196 Cliff Rd, Nantucket, MA 02554

Ideally located on 1.84 acres near the Tupancy Links and Washing Pond, 196 Cliff Road is a timeless estate offering privacy, space, and an easy approach to Town. A sparkling pool, manicured grounds, and a two-car garage complement the beautifully designed 4-bedroom main house and charming 1-bedroom guest cottage.Just across from Washing Pond Road, enjoy easy public access to a secluded

John McGarr Maury People Sotheby's International Realty

196 Cliff Rd, Nantucket, MA 02554
/46
$7,200,000
- 7 Beds
- 6.5 Baths
- 4,579 Sq Ft
110 Baxter Rd, Nantucket, MA 02554

This family compound is beautifully sited on a nearly one-acre parcel, affording privacy along with a beautiful landscape that provides a stunning panoramic view that includes the iconic Sankaty Light house and Sankaty Golf Course. The large landscaped setting and expansive views create a vista that is a rare find. The four-bedroom main house has three finished floors and enjoys an open floor

Debbie Willett Great Point Properties

110 Baxter Rd, Nantucket, MA 02554
/118
$10,495,000
- 10 Beds
- 12 Baths
- 5,088 Sq Ft
24 Flintlock Rd, Nantucket, MA 02554

Nestled on an expansive 2.45-acre parcel adjoining pristine Nantucket Land Bank conservation land, 24 Flintlock Road offers a private and tranquil retreat for discerning families. The homes on this thoughtfully curated estate create a charming family compound, featuring a generously appointed six-bedroom main residence, complemented by a delightful three-bedroom guest cottage, a stylish pool

Chandra Miller Maury People Sotheby's International Realty

24 Flintlock Rd, Nantucket, MA 02554
/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
/55
$8,195,000
- 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

Lucie Cristler Maury People Sotheby's International Realty

115 Surfside Rd, Nantucket, MA 02554
/90
$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
/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 5,300 square feet of beautifully appointed living space. Additional amenities include a two-car garage with a studio

Chris Kling J Pepper Frazier Co.

2 A Morgan Square, Nantucket, MA 02554
/64
$8,595,000
- 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
/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
/133
$8,250,000
- 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
/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
/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
/32
$8,950,000
- 5 Beds
- 4 Baths
- 3,156 Sq Ft
78 Cliff Rd, Nantucket, MA 02554

Sprawling one-level house and newer 2005-built garage/apartment in a prime Cliff Road location. Located close to all of the amenities of Nantucket Town and minutes to sandy Steps Beach off of Lincoln Circle. The property is offered for sale as as a whole on 3 oversized Land Court registered lots. Should one wish to build a new estate (or three), there is HDC-approved demo/move permits in process

Ed Gillum J Pepper Frazier Co.

78 Cliff Rd, Nantucket, MA 02554
/21
$2,575,000
- 5 Beds
- 5.5 Baths
- 3,985 Sq Ft
10 Beach Grass Rd, Nantucket, MA 02554

New Construction, Now Completed! Nantucket's Best Kept Secret...This neighborhood will consist of 36 single family homes, with a new amenities center, The Landing, featuring an outdoor heated pool, patio, lounge area, putting area, outdoor California kitchen and grilling center, indoor clubhouse space, fitness center and fire pit. This Captain home design features expansive open sun-filled

Janice Dumont JD Advisors, Inc

10 Beach Grass Rd, Nantucket, MA 02554
/64
$6,399,000
- 6 Beds
- 5 Baths
- 4,064 Sq Ft
25 Pond View Dr, Nantucket, MA 02554

Set on a quiet street in a highly desirable location, this special property offers a rare combination of privacy, natural beauty, and versatile living. With distant ocean views and abutting Land Bank conservation land, it provides direct access to trails leading to Miacomet Pond and one of Nantucket’s most pristine beaches.The 4-bedroom, 3-bath main house is designed to maximize light,

Michele Kelsey William Raveis Nantucket

25 Pond View Dr, Nantucket, MA 02554
/34
$16,500,000
- 7 Beds
- 9 Baths
- 4,762 Sq Ft
174 Cliff Rd, Nantucket, MA 02554

Renew with ease at 174 Cliff Road, where acres of conservation land beckon at your front and back doors. Nestled on an exceptionally private one-and-a-half acres, the estate comprises three thoughtfully designed structures, anchored by a pool and landscaped outdoor living spaces. The property blends classic architectural charm with modern sophistication to feel both enduring and effortless. The

Cameron Gammill Fisher Real Estate

174 Cliff Rd, Nantucket, MA 02554
/40
$5,995,000
- 11 Beds
- 8.5 Baths
- 6,005 Sq Ft
45 Pleasant St Unit A&B, Nantucket, MA 02554

45 A & B Pleasant Street offer a rare opportunity to own two distinct homes in the heart of Town, each brimming with modern upgrades and timeless charm. This versatile property provides a multitude of options for potential buyers. Whether you need additional space for extended family, wish to live in one home while renting the other, or prefer to rent both separately or together for events like

Benjamin Lincoln Compass Massachusetts, LLC

45 Pleasant St Unit A&B, Nantucket, MA 02554
/59
$6,795,000
- 5 Beds
- 5.5 Baths
- 3,366 Sq Ft
32 Union St, Nantucket, MA 02554

Beautifully restored and maintained home in the heart of the Old Historic District, with Main St and the waterfront at your doorstep. Built is 1786, the William Coffin House offers 5 bedrooms and multiple indoor and outdoor living spaces over three floors. Historic details blend seamlessly with modern convenience and comfort. Ample roof walk offers stunning harbor views. Private back yard and

Josh Lothian William Raveis Nantucket

32 Union St, Nantucket, MA 02554
/26
$6,495,000
- 6 Beds
- 7 Baths
- 4,457 Sq Ft
33 1/2 Vesper Ln, Nantucket, MA 02554

Welcome to 33 1/2 Vesper – Your Coastal Retreat!Nestled in the heart of Nantucket Island, this charming property offers a perfect blend of modern luxury and traditional island charm. With its prime location, just moments away from pristine beaches and picturesque cobblestone streets, 33 1/2 Vesper promises an unforgettable getaway. With a total of six bedrooms spread out across a three level

Susan Shepherd Shepherd Real Estate

33 1/2 Vesper Ln, Nantucket, MA 02554
/23
$4,275,000
- 5 Beds
- 4.5 Baths
- 3,020 Sq Ft
33 Pine St, Nantucket, MA 02554

Charming Two-Family Home in the Heart of Downtown Nantucket. Nestled in the vibrant heart of downtown Nantucket, 33 Pine Street offers the perfect blend of historic charm and modern versatility. Currently configured as a two-family home, this spacious property features a total of 5 bedrooms and 4.5 bathrooms across multiple levels—ideal for extended family, guests, or rental potential.The

Michael Passaro Douglas Elliman Nantucket

33 Pine St, Nantucket, MA 02554
/14
$5,295,000
- 6 Beds
- 5.5 Baths
- 4,956 Sq Ft
75 Fairgrounds Rd, Nantucket, MA 02554

Thoughtfully designed by J5 Development for modern living and seamless indoor-outdoor flow, 75 Fairgrounds Road will offer six bedrooms and five-and-a-half bathrooms across three finished levels. With an open-plan layout, multiple living areas, and sliding glass doors leading to the pool, deck, and cabana, this newly built home blends sophistication with laid-back island comfort. Ideal for

Brian Sullivan Fisher Real Estate

75 Fairgrounds Rd, Nantucket, MA 02554
/42
$4,200,000
- 6 Beds
- 3 Baths
- 2,011 Sq Ft
2 Lily St, Nantucket, MA 02554

"The Bo'sn's Bunt” captures the charm and historic character of ’Sconset at its finest. This unique property includes two separate dwellings, each reflecting classic ’Sconset-style architecture. The main house is one of the original rental cottages built by Edward Underhill, a devoted ’Sconset enthusiast. The second cottage offers a retreat for visiting guests.With six bedrooms and three

Sarah Maneikis Great Point Properties

2 Lily St, Nantucket, MA 02554
/125
$10,495,000
- 8 Beds
- 9 Baths
- 5,803 Sq Ft
4 Fintry Ln, Nantucket, MA 02554

WELCOME TO DIONIS seclusion ~ Set on 1.84 acres and enveloped by over 700 acres of pristine conservation land, this exceptional eight-bedroom estate in Dionis offers rare privacy and sweeping sunset vistas. The thoughtfully designed six-bedroom main house features expansive indoor and outdoor living spaces ideal for entertaining or relaxing in complete seclusion. A separate two-bedroom garage

Chandra Miller Maury People Sotheby's International Realty

4 Fintry Ln, Nantucket, MA 02554
/45
$11,950,000
- 7 Beds
- 7.5 Baths
- 6,279 Sq Ft
59 Polpis Rd, Nantucket, MA 02554

Experience refined coastal living at 59 Polpis Road, the latest masterpiece by renowned builder Randy Sharp. Set on just under an acre in the prestigious Polpis area, this exceptional 7-bedroom home offers sweeping views over the pastoral fields of Moors End Farm. Thoughtfully designed for modern living, the floor plan features open-concept interiors and three distinct living areas—one on each

Brian Sullivan Fisher Real Estate

59 Polpis Rd, Nantucket, MA 02554
/64
$5,995,000
- 5 Beds
- 6.5 Baths
- 3,900 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
/59
$5,800,000
- 6 Beds
- 6 Baths
- 3,127 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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