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5-Bedroom Homes for Sale in Nantucket County MA

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  • /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

    $3,900,000

    • 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
  • /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
  • /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
  • /17

    $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 some 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

    Robert F Egan J Pepper Frazier Co.

    20 Pine Grove Ln, Nantucket, MA 02554
  • /40

    $10,500,000

    • 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
  • /27

    $6,250,000

    • 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
  • /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
  • /39

    $6,895,000

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

    4 Mariner Way, Nantucket, MA 02554

    Enjoy harbor views from the expansive deck off the 2nd floor of 4 Mariner Way. Newly built four-bedroom main residence with a separate one-bedroom guest house, located within an exclusive enclave of just five homes. Convenient access to Main Street, the Great Harbor Yacht Club, Monomoy’s scenic creeks, and the in-town bike path. The thoughtfully designed guest house is a private space for

    Bernadette Meyer Maury People Sotheby's International Realty

    4 Mariner Way, Nantucket, MA 02554
  • /55

    $3,950,000

    • 6 Beds
    • 5.5 Baths
    • 6,066 Sq Ft

    12 Longwood Dr, Nantucket, MA 02554

    Minutes away from NGC, and including 2 complete homes. 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

    Robert Young William Raveis Nantucket

    12 Longwood Dr, Nantucket, MA 02554
  • /3

    $5,995,000

    • 15 Beds
    • 14.5 Baths
    • 5,643 Sq Ft

    27 Fair St, Nantucket, MA 02554

    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 plans 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

    Dalton Frazier J Pepper Frazier Co.

    27 Fair St, Nantucket, MA 02554
  • /4

    $3,995,000

    • 9 Beds
    • 6.5 Baths
    • 4,988 Sq Ft

    29 Fair St, Nantucket, MA 02554

    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. Potential for sub-division.

    Dalton Frazier J Pepper Frazier Co.

    29 Fair St, Nantucket, MA 02554
  • /50

    $4,750,000

    • 5 Beds
    • 4.5 Baths
    • 3,788 Sq Ft

    27 Wigwam Rd, Nantucket, MA 02554

    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

    Chandra Miller Maury People Sotheby's International Realty

    27 Wigwam Rd, Nantucket, MA 02554
  • /31

    $12,950,000

    • 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 main residence and cottage/garage with additional 3 bedrooms and 2 bathrooms 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

    Brian Sullivan Fisher Real Estate

    4 Shawkemo Hills Ln, Nantucket, MA 02554
  • /31

    $19,400,000

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

    4 Shawkemo Hills Ln, Nantucket, MA 02554

    Nestled in a coveted location on Nantucket, this exceptional five-bedroom, four full-bath, two half-bath main residence and cottage/garage with additional 3 bedrooms and 2 bathrooms, 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

    Brian Sullivan Fisher Real Estate

    4 Shawkemo Hills Ln, Nantucket, MA 02554
  • /89

    $33,000,000

    • 12 Beds
    • 15 Baths
    • 15,561 Sq Ft

    256 Polpis Rd, Nantucket, MA 02554

    256 Polpis Road is an exceptional 6.42-acre legacy estate that offers stunning views and direct water access to Polpis Harbor. Botticelli and Pohl Architects, and Hehir Group Custom Builders have spent two years thoughtfully and completely reimagining this grand and refined historic home. This rare offering is ready for immediate enjoyment for those seeking luxury living and the best that

    Greg McKechnie Great Point Properties

    256 Polpis Rd, Nantucket, MA 02554
  • /70

    $3,275,000

    • 6 Beds
    • 5.5 Baths
    • 3,778 Sq Ft

    24 MacYs Ln, Nantucket, MA 02554

    Welcome to this exceptional custom-built residence offering 3,778 sq ft under air plus a massive basement with soaring 10-foot ceilings—a rare find with endless potential for expansion or customization.This meticulously crafted home showcases premium finishes throughout, including rich walnut floors, a brand-new A/C system, and a spacious second-level deck perfect for outdoor living. The

    Robert Sarkisian Berkshire Hathaway HomeServices Island Properties Nantucket

    24 MacYs Ln, Nantucket, MA 02554
  • /75

    $18,875,000

    • 10 Beds
    • 6 Baths
    • 5,373 Sq Ft

    35 Shell St, Nantucket, MA 02564

    For the first time in nearly 100 years, the iconic Wade Cottages—a cherished cornerstone of ’Sconset history—is being offered for sale. Originally acquired in 1929 as a family estate, this storied property has since served as both an inn and a beloved single-family home. Rich in character, steeped in history, and unrivaled in location, this is truly a once-in-a-lifetime opportunity. The listing

    Liza Ottani Lee Real Estate

    35 Shell St, Nantucket, MA 02564
  • /20

    $6,395,000

    • 5 Beds
    • 7 Baths
    • 4,460 Sq Ft

    86 Cliff Rd, Nantucket, MA 02554

    Discover the ultimate Nantucket getaway at 86 Cliff Road—a stunning, newly constructed home nestled in the heart of the coveted Cliff neighborhood. Thoughtfully designed across three finished levels, this fully furnished five-bedroom residence combines refined craftsmanship and modern comforts, creating the perfect setting for memorable island living. Offered fully furnished, this gorgeous

    Jennifer Shalley Allen Fisher Real Estate

    86 Cliff Rd, Nantucket, MA 02554
  • /77

    $10,995,000

    • 6 Beds
    • 8 Baths
    • 5,100 Sq Ft

    15 N Water St, Nantucket, MA 02554

    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

    Penny Dey Atlantic East Nantucket Real Estate

    15 N Water St, Nantucket, MA 02554
  • /66

    $10,995,000

    • 5 Beds
    • 4.5 Baths
    • 5,301 Sq Ft

    9 Pleasant St, Nantucket, MA 02554

    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

    Nicole Bousquet Great Point Properties

    9 Pleasant St, Nantucket, MA 02554
  • /58

    $11,950,000

    • 6 Beds
    • 6.5 Baths
    • 7,968 Sq Ft

    11 Eel Point Rd, Nantucket, MA 02554

    As you pass through the allee created by the canopy of mature cherry trees over the winding shell driveway and through the electric gates, you will arrive at this private, estate-like home located in one of the most coveted areas on Nantucket. Completely and tastefully renovated from the ground up in 2025, this exceptional property includes the large main residence with an exceptional floor plan

    J Pepper Frazier II J Pepper Frazier Co.

    11 Eel Point Rd, Nantucket, MA 02554
  • /90

    $22,995,000

    • 6 Beds
    • 9 Baths
    • 6,694 Sq Ft

    3 Beacon Ln, Nantucket, MA 02554

    Waterfront living at its best, fronting directly onto Sesachacha Pond in a very private part of Quidnet, with views of the ocean and Sankaty Lighthouse. If you are looking for a "one of a kind" Nantucket estate, this is it! Tucked behind a gate down a long hedge lined drive you will find this gem of a property. Designed by Workshop APD and built by Reid Builders of Nantucket, this property

    Dawn Hill Holdgate Great Point Properties

    3 Beacon Ln, Nantucket, MA 02554
  • /11

    $5,950,000

    • 5 Beds
    • 5.5 Baths
    • 3,556 Sq Ft

    4 Sunset Hill Ln, Nantucket, MA 02554

    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

    Chandra Miller Maury People Sotheby's International Realty

    4 Sunset Hill Ln, Nantucket, MA 02554
  • /49

    $22,750,000

    • 12 Beds
    • 10.5 Baths
    • 11,564 Sq Ft

    1 Ocean Ave, Nantucket, MA 02564

    A legacy estate in the heart of ’Sconset, One Ocean Avenue is one of Nantucket’s most iconic offerings. Spanning three parcels and perched above the Atlantic, this storied coastal compound includes four dwellings — the grand main house, The Rec Cottage, The Stable, and The Chauffeur’s Cottage — each thoughtfully preserved to honor its early 20th-century origins.Steeped in history, each

    Bernadette Meyer Maury People Sotheby's International Realty

    1 Ocean Ave, Nantucket, MA 02564
  • /41

    $6,145,000

    • 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

    Edward Doherty EW Doherty Real Estate

    6 Mariner Way, Nantucket, MA 02554
  • /31

    $5,500,000

    • 8 Beds
    • 5.5 Baths
    • 3,789 Sq Ft

    13 Parson Ln, Nantucket, MA 02554

    Welcome to True North, an extraordinary 2.94-acre estate on Nantucket that captures the essence of island living. With two stunning homes and approx. 2,000 SF of ground cover, this rare offering combines serene privacy, sophisticated design, and breathtaking views of the Atlantic Ocean and Sankaty Head Lighthouse. Whether you’re seeking a private retreat or the ideal family compound, True North

    Nicole Tirapelli Douglas Elliman Real Estate - Nantucket

    13 Parson Ln, Nantucket, MA 02554
  • /23

    $2,250,000

    • 5 Beds
    • 3.5 Baths
    • 3,739 Sq Ft

    6 Dovekie Ct, Nantucket, MA 02554

    Spacious and sun-filled 5-bedroom, 3.5-bathroom home is privately tucked away in the corner of a cul-de-sac in the charming Naushop neighborhood. With a flowing open floor plan and thoughtfully designed spaces, this property offers the perfect blend of comfort, functionality, and classic Nantucket charm.This home gives you access to beautifully maintained amenities, including tennis

    Robert Sabelhaus Great Point Properties

    6 Dovekie Ct, Nantucket, MA 02554
  • /67

    $4,940,000

    • 5 Beds
    • 6 Baths
    • 4,871 Sq Ft

    15 Skyline Dr, Nantucket, MA 02554

    Enjoy tremendous privacy and close proximity to south shore beaches in this 5 bedroom, Surfside Estate. At 3.23 acres it is one of the largest residential properties currently available. A serpentine driveway winds through the pines to this handsome professionally landscaped home. You enter into a spacious living room with fire place, soaring ceilings open to the dining area and new kitchen. A

    Cynthia Lenhart William Raveis Nantucket

    15 Skyline Dr, Nantucket, MA 02554
  • /42

    $3,549,000

    • 5 Beds
    • 5 Baths
    • 3,251 Sq Ft

    8 Grey Lady Ln, Nantucket, MA 02554

    Welcome to the epitome of modern living at Grey Lady Lane! This meticulously crafted 5 bedroom, 5 bath new construction home boasts three floors of exquisite living space, offering the perfect blend of style, comfort, and convenience. Located in a charming community of just 12 homes, residents will enjoy exclusive access to a sparkling community pool and cabana, creating the perfect setting for

    Jessica Newman Maury People Sotheby's International Realty

    8 Grey Lady Ln, Nantucket, MA 02554
  • /20

    $1,119,000

    • 7 Beds
    • 7 Baths
    • 6,800 Sq Ft

    11 Meadow Ln, Nantucket, MA 02554

    New co-ownership opportunity: Own one-eighth of this turnkey home by Pacaso. Cedar Isle blends classic design with modern finishes, a rare find in Nantucket. The home includes a 3-story main house and guest house. Enjoy bike paths, beaches, and a vibrant downtown waterfront scene. The main house features an open plan with glass doors opening to a pool, spa, and landscaped backyard. A gourmet

    Jason Saphire www.HomeZu.com

    11 Meadow Ln, Nantucket, MA 02554
  • /64

    $13,995,000

    • 6 Beds
    • 9 Baths
    • 6,325 Sq Ft

    14 Correia Ln, Nantucket, MA 02554

    Luxury Estate in Surfside - Your Dream Home Awaits!Introducing a brand new exquisite construction in the heart of Surfside! This magnificent property offers a 5 bedroom main house, a 1 bedroom cottage, and an oversized garage, all nestled on a private 1 acre compound. The main house boasts five spacious bedrooms, each designed with luxurious finishes. The separate one- bedroom cottage

    Marybeth Gibson Maury People Sotheby's International Realty

    14 Correia Ln, Nantucket, MA 02554
  • /30

    $14,995,000

    • 6 Beds
    • 9 Baths
    • 5,693 Sq Ft

    10 Maxey Pond Rd, Nantucket, MA 02554

    Sublime Coastal Retreat – 10 Maxey Pond nestled on 3.07 acres, just 5 minutes from downtown, this stunning estate, designed by Lucas Velle of Outside-In By design & Chip Webster Architecture, offers ultimate privacy with sweeping views of Maxey Pond and the ocean. Spanning 5600+ sq. ft., it features 6 bedrooms, 6 full baths, and 3 half baths. Sustainable luxury defines this home, powered by solar

    Nicole Tirapelli Douglas Elliman Real Estate - Nantucket

    10 Maxey Pond Rd, Nantucket, MA 02554

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