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Homes for Sale in 02535

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  • /24

    $4,695,000

    • 5 Beds
    • 2.5 Baths
    • 3,885 Sq Ft

    18 Homeward Way, Chilmark, MA 02535

    Welcome to 18 Homeward Way — a peaceful Chilmark retreat tucked off scenic North Road, just minutes from the storied fishing village of Menemsha. This rare 15-acre offering includes two buildable parcels, creating an extraordinary opportunity for a Vineyard compound.The impeccably maintained residence, built in 1986, radiates classic Vineyard charm. Its thoughtful single-level layout

    Bill Rossi Studio Realty

    18 Homeward Way, Chilmark, MA 02535
  • /28

    $7,450,000

    • 5 Beds
    • 4.5 Baths
    • 5,000 Sq Ft

    7 Clay Pit Ln, Aquinnah, MA 02535

    Stunning waterfront home with panoramic waterviews. The home was designed by Hutker Associates, built by Andrew Flake, and landscaped by Michael Van Valkenburgh - three of the most renowned names in Martha's Vineyard home creation. Little wonder it was featured on the cover of Beautiful Home magazine and has been included in several other home design magazines and books. The 5000 sq ft house

    Mark Jenkins Wallace & Co. Sotheby's

    7 Clay Pit Ln, Aquinnah, MA 02535
  • /42

    $4,250,000

    • 3 Beds
    • 6 Baths
    • 3,171 Sq Ft

    15 Old Farm Rd, Chilmark, MA 02535

    CHILMARK BLISS – Refined Retreat | 15 Old Farm Road. Set on 3+ acres of manicured grounds, this 2020 Peter Breese–redesigned home blends elegance and tranquility. A serene pond, stream, and custom hardscape set the tone. Inside, a dramatic open kitchen/living area boasts high-end appliances, stone countertops, and a striking fireplace, with a pantry leading to a screened porch. The main-level

    Tina Miller Donnelly + Co.

    15 Old Farm Rd, Chilmark, MA 02535
  • /42

    $3,995,000

    • 3 Beds
    • 4 Baths
    • 3,426 Sq Ft

    96 Hammett Ln, Chilmark, MA 02535

    Beautifully designed and built Post & Beam style home is tastefully thought out and meticulously maintained. The open living, dining and kitchen feature custom built-ins, a wood burning fireplace and a fabulous gourmet kitchen with Wolfe 8 burner professional style stove, Sub Zero refrigerator, Boshe dishwasher, soapstone counters and a butlers pantry with extra cupboards, shelving and a wine

    Brenda Galligan Karen M. Overtoom R.E.

    96 Hammett Ln, Chilmark, MA 02535
  • /36

    $4,950,000

    • 5 Beds
    • 4 Baths
    • 3,413 Sq Ft

    122 Old Farm Rd, Chilmark, MA 02535

    An incomparable setting in Chilmark, a beautifully renovated 5-bedroom home, stunning landscape and hardscape, all on three separate building lots totaling almost 14 acres - this is Allerton farm. The historic house has been expanded with new additions to create a thoroughly modern residence that nevertheless retains a charm that could not be achieved without technical expertise, attention to

    Mark Jenkins Wallace & Co. Sotheby's

    122 Old Farm Rd, Chilmark, MA 02535
  • /34

    $4,950,000

    • 5 Beds
    • 4.5 Baths
    • 3,413 Sq Ft

    124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535

    An incomparable setting in Chilmark, a beautifully renovated 5-bedroom home, stunning landscape and hardscape, all on three separate building lots totaling almost 14 acres - this is Allerton farm. The historic house has been expanded with new additions to create a thoroughly modern residence that nevertheless retains a charm that could not be achieved without technical expertise, attention to

    Mark Jenkins Wallace & Co. Sotheby's International Realty

    124 Old Farm Rd Unit 122, 116, Chilmark, MA 02535
  • /46

    $6,750,000

    • 3 Beds
    • 3 Baths
    • 3,432 Sq Ft

    44 Cencelle St, Chilmark, MA 02535

    This private 21-acre Chilmark estate with ocean views, tucked away in the rolling hills and farmlands of Chilmark, offers sweeping ocean views to the south and a rare sense of seclusion and serenity. At the heart of the property is a striking modern style home, thoughtfully designed to bring the outdoors in. Expansive walls of glass flood the interior with natural light and frame panoramic views

    Meg Bodnar Tea Lane Associates

    44 Cencelle St, Chilmark, MA 02535
  • /49

    $6,490,000

    • 6 Beds
    • 8 Baths
    • 5,660 Sq Ft

    60 Meetinghouse Rd, Chilmark, MA 02535

    This spectacular and bright modern american farmhouse is perfectly sited to capture the varied scenic beauty that surrounds the farm. Built in 2021 with great attention to detail and materials, this home was created around gatherings and community with ample space for the extended family. The land has been lovingly curated into a place which can grow, generate and support those who want to have

    Jim Feiner Feiner Real Estate

    60 Meetinghouse Rd, Chilmark, MA 02535
  • /52

    $3,975,000

    • 4 Beds
    • 3 Baths
    • 2,704 Sq Ft

    370 Lighthouse Rd, Aquinnah, MA 02535

    Stunning waterview living with an active view that will never disappoint. Wake up every morning to breathtaking 180 degree water views in this beautifully appointed 4-bedroom, 3-bath coastal retreat. Perfectly situated to capture sunrise to sunset vistas, this home offers a blend of summer vibes with year-round living amenities. Step inside to find an open-concept living space filled with natural

    Jill Napior Tea Lane Associates

    370 Lighthouse Rd, Aquinnah, MA 02535
  • /34

    $4,350,000

    • 3 Beds
    • 2 Baths
    • 1,260 Sq Ft

    131 State Rd, Chilmark, MA 02535

    Magical waterfront Quitsa pond cottage with private dock. This home has the most spectacular views including sunsets and an intimate relationship with the charming and timeless waterfront at Quitsa Pond. Designed with the setting in mind this sublime piece of architecture has wonderful spaces, fantastic detail and so much packed into a smaller home. Landscape design by Edwina von Gal accentuates

    Jim Feiner Feiner Real Estate

    131 State Rd, Chilmark, MA 02535
  • /37

    $4,850,000

    • 5 Beds
    • 3 Baths
    • 3,440 Sq Ft

    146 Quansoo Rd, Chilmark, MA 02535

    Nestled along the beautiful and tranquil shoreline of Tisbury Great Pond and surrounded by a stunning natural environment of water, sand and sky, this is an unparallelled beach house experience on the south shore of Chilmark. The five-bedroom home consists of a three-bedroom main house connected by walkways to a two-bedroom guest wing with studio space above, all with spectacular water views

    Meg Bodnar Tea Lane Associates

    146 Quansoo Rd, Chilmark, MA 02535
  • /16

    $445,000

    • Land
    • 0 Acre

    0 Quansoo Beach Lot Unit 50 43710, Chilmark, MA 02535

    Spectacular beach lot at Quansoo. This is the ultimate amenity. Ownership provides access to one of the most stunning beaches on the entire eastern seaboard. On one side is the majestic Atlantic Ocean and on the other the calm waters of Tisbury Great Pond where kids can catch crabs and play safely as you watch. Skip the lines and crowds at other beaches - come and go as you please for sun, sand,

    Mark Jenkins Wallace & Co. Sotheby's

    0 Quansoo Beach Lot Unit 50 43710, Chilmark, MA 02535
  • /33

    $4,995,000

    • 7 Beds
    • 4.5 Baths
    • 6,921 Sq Ft

    19 Locust Ln, Aquinnah, MA 02535

    This beautifully designed and built home is privately sited on 4.02 acres overlooking a pastoral setting with amazing ocean views and bordered by stone walls. The spacious entry hall steps into a formal living and dining room with oversized windows that take in the amazing North Shore ocean views, tall ceilings, a field stone fireplace and concrete floors heated by radiant heat. French doors take

    Brenda Galligan Karen M. Overtoom R.E.

    19 Locust Ln, Aquinnah, MA 02535
  • /32

    $2,250,000

    • 4 Beds
    • 2.5 Baths
    • 2,522 Sq Ft

    29 Old Nursery Ln, Chilmark, MA 02535

    Modern Cape style home located off Tea Lane could be your special Chilmark retreat. This four bedroom, 2.5 bathroom home needs some updating but is in good condition. Living room with fireplace, dining area and family room provide space for living. Attached two bay garage allows for storage and projects. Wood working area in the basement is a plus. Enjoy the outdoors via the screened porch, large

    Julianna Flanders Flanders Real Estate

    29 Old Nursery Ln, Chilmark, MA 02535
  • /41

    $3,600,000

    • 3 Beds
    • 4 Baths
    • 2,500 Sq Ft

    27 Clambelly Rd, Chilmark, MA 02535

    A place of serenity tucked in the woods of Chilmark. Complete renovation 2017/2018, large fenced in back yard with exquisite fish pond with waterfall and lighting. Kitchen has concrete countertops, sub zero refrigerator, Wolf Oven & Speed Oven. Large open formal dining area and open formal sitting area with fireplace. Beautiful reclaimed wood flooring. LED lighting throughout house, Media

    Julianna Flanders Flanders Real Estate

    27 Clambelly Rd, Chilmark, MA 02535
  • /26

    $3,695,000

    • Land
    • 6.7 Acres
    • $551,493 per Acre

    32 Stonewall Road and 4 Cedar Ln Unit 2.1 and 2.2, Chilmark, MA 02535

    Discover an exceptional opportunity with this rare combination of two abutting parcels spanning more than 6 acres in a coveted location offering water views and Atlantic Ocean private beach access. Surfers and fishermen delight in this location! The Stonewall Association is a beloved area of Chilmark in a supreme location for easy Chilmark living close to the Chilmark Store, the Chilmark

    Jill Napior Tea Lane Associates

    32 Stonewall Road and 4 Cedar Ln Unit 2.1 and 2.2, Chilmark, MA 02535
  • /13

    $1,150,000

    • Land
    • 2.02 Acres
    • $569,307 per Acre

    00 Old Field Rd, Aquinnah, MA 02535

    The nearby roar of the Atlantic can be heard from this pristine two-acre building opportunity in Aquinnah, ideally located at the end of Old Field Road with easy access from Moshup Trail. A storybook walking path through woods and fields over an easement bordering a majestic beetlebung grove and over a bubbling stream, leads directly to the entrance of cherished Philbin Beach. A thoughtfully

    Katherine Donahue Sandpiper Realty Inc

    00 Old Field Rd, Aquinnah, MA 02535
  • /34

    $2,675,000

    • 3 Beds
    • 1.5 Baths
    • 1,540 Sq Ft

    5 Ocean View Farm Rd, Chilmark, MA 02535

    Designed by the famous mid century architect Andrew Geller, this contemporary home is situated at the top of the parcel with ocean views and a glimpse of Chilmark pond. There is ample open space to accommodate family and friends and overlooks the large meadow which follows the stone wall to South Road. Access to walking trails, and Lucy Vincent Beach is a short distance away.

    Natalie Conroy Conroy & Company R.E., Inc.

    5 Ocean View Farm Rd, Chilmark, MA 02535
  • /36

    $3,250,000

    • 4 Beds
    • 3.5 Baths
    • 2,515 Sq Ft

    300 North Rd, Chilmark, MA 02535

    Winding tree lined driveway off North Rd brings you to this commanding, custom designed residence built by a top tier island builder. This home is set on over 4 private acres of rolling meadows and big sky views. Main living space is all on one level which includes primary bedroom with en-suite bath, large living area with fireplace, bright sunroom or second living room, custom kitchen and

    Rebecca V Conroy Conroy & Company R.E., Inc.

    300 North Rd, Chilmark, MA 02535
  • /40

    $1,899,000

    • 4 Beds
    • 3.5 Baths
    • 2,061 Sq Ft

    174 Middle Rd, Chilmark, MA 02535

    Nestled in the heart of Chilmark, this four-bedroom home offers a blend of comfort, convenience, and timeless Vineyard charm. Thoughtfully designed with distinct, well-proportioned rooms, the home centers around an expansive, sunlit, eat-in kitchen featuring dual ovens, elegant granite countertops, and extensive custom cherry wood built-ins that combine beauty and practicality. The welcoming

    Sheila Morse Island Real Estate

    174 Middle Rd, Chilmark, MA 02535
  • /10

    $350,000

    • Land
    • 0 Acre

    0 Moshup Trail Unit 32500206, Aquinnah, MA 02535

    Enjoy coveted access to one of Martha's Vineyard's most stunning sandy beaches, located just off Moshup Trail in Aquinnah. This secluded beach is shared with only seven other members, ensuring a peaceful and private coastal experience. Located near Aquinnah's iconic ''Painted House,'' the property includes use of a private gated parking area and a picturesque stretch of shoreline perfect for

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    0 Moshup Trail Unit 32500206, Aquinnah, MA 02535
  • /10

    $350,000

    • Land
    • 1.26 Acres
    • $277,778 per Acre

    0 Moshup Trail Unit 27 & 146 43498, Aquinnah, MA 02535

    Enjoy coveted access to one of Martha's Vineyard’s most stunning sandy beaches, located just off Moshup Trail in Aquinnah. This secluded beach is shared with only seven other members, ensuring a peaceful and private coastal experience. Located near Aquinnah’s iconic “Painted House,” the property includes use of a private gated parking area and a picturesque stretch of shoreline perfect for

    Alyssa Halisky Wallace & Co. Sotheby's

    0 Moshup Trail Unit 27 & 146 43498, Aquinnah, MA 02535
  • /43

    $1,850,000

    • 3 Beds
    • 3.5 Baths
    • 2,986 Sq Ft

    1 Harpoon Hollow, Aquinnah, MA 02535

    Beautiful, solidly custom built home featuring red oak Post and Beam work throughout. The many unique and attractive features are sure to delight the most discerning buyer. Abuts 5.9 acres of forever protected Landbank property extending the 2 private acres of this property for extraordinary privacy. A brick walk bordered by a lovely boxwood hedge leads to two separate entrances into the home.

    Elaine Vanderhoop Beachcombers of MV

    1 Harpoon Hollow, Aquinnah, MA 02535
  • /20

    $895,000

    • Land
    • 0 Acre

    0 Jeffers Way Unit 73387831, Aquinnah, MA 02535

    This lovely parcel in Aquinnah offers a rare opportunity to own a pristine 3.8 acre parcel on Martha's Vineyard. This elevated, hilly lot is bordered by Classic New England stone walls and surrounded by mature trees, providing both privacy and a serene natural setting. The property is prepared for development, featuring an installed well, a 3-bedroom septic, electric and a completed archeological

    Brenda Galligan Karen M. Overtoom R.E.

    0 Jeffers Way Unit 73387831, Aquinnah, MA 02535
  • /8

    $1,695,000

    • Land
    • 0 Acre

    19A Locust Ln, Aquinnah, MA 02535

    This private 6.19 acres parcel has been approved for sub-division and not yet recorded. Potential to add acreage. Proposed lot lines and designated building envelope. Lovely rolling topography with mature trees. Septic & Well not installed

    Brenda Galligan Karen M. Overtoom R.E.

    19A Locust Ln, Aquinnah, MA 02535
  • /26

    $2,000,000

    • 3 Beds
    • 2.5 Baths
    • 1,784 Sq Ft

    12 Lobsterville Rd, Aquinnah, MA 02535

    12 Lobsterville Rd in Aquinnah is a uniquely designed contemporary home set on 2.6 acres of lush grounds with large tracts of conservation land nearby. Open concept living, dining, kitchen on the second floor with unobstructed ocean views of Vineyard Sound. Spacious deck for sunset viewing and grassy lawn for sundown games. Walking distance to Lobsterville Beach and a short bike ride to the

    Tina Palmer Conroy & Company R.E., Inc.

    12 Lobsterville Rd, Aquinnah, MA 02535
  • /33

    $1,985,000

    • Land
    • 3.58 Acres
    • $554,469 per Acre

    4 Cedar Ln Unit 2.2, Chilmark, MA 02535

    Premier Build-Ready Lot with Private Beach AccessGet to know Stonewall Association, one of Chilmark’s most sought-after enclaves on the South Shore. This sunny, build-ready parcel offers a rare opportunity to own land with deeded private access to Stonewall Beach—a beloved destination for swimming, surfing, excellent fishing and summer memories. Set on beautifully contoured land with

    Jill Napior Tea Lane Associates

    4 Cedar Ln Unit 2.2, Chilmark, MA 02535
  • /21

    $895,000

    • Land
    • 3.8 Acres
    • $235,526 per Acre

    0 Jeffers Way Unit 165 43370, Aquinnah, MA 02535

    This lovely parcel in Aquinnah offers a rare opportunity to own a pristine 3.8 acre parcel on Martha's Vineyard. This elevated, hilly lot is bordered by Classic New England stone walls and surrounded by mature trees, providing both privacy and a serene natural setting. The property is prepared for development, featuring an installed well, a 3-bedroom septic, electric and a completed

    Brenda Galligan Karen M. Overtoom R.E.

    0 Jeffers Way Unit 165 43370, Aquinnah, MA 02535
  • /35

    $13,000,000

    • 5 Beds
    • 4.5 Baths
    • 3,758 Sq Ft

    6 Wakeman Rd, Chilmark, MA 02535

    A 1930s-built home that has been remarkably updated to retain its historic charm while incorporating sophisticated and modern amenities. The house overlooks the Chilmark Great Pond and the Atlantic Ocean beyond. The Main House includes 3 bedrooms, 3 beautifully renovated bathrooms, a walk-in closet, a Pantry, a Library/Media room, a full basement, Outdoor showers, and a screened-in porch. The

    Julianna Flanders Flanders Real Estate

    6 Wakeman Rd, Chilmark, MA 02535
  • /25

    $3,600,000

    • 3 Beds
    • 3 Baths
    • 4,382 Sq Ft

    88 & 90 Quenames Rd, Chilmark, MA 02535

    Make your own Chilmark dream come true!12.6 +/- acres of prime land allows you to create your own familycompound or Island Farm. Enjoy the peacefulness of the Chilmarkwith room to expand. Two separate buildable lots provides you uniqueoptions. The Main house has three bedrooms, three bathrooms, twostudies, multiple living spaces and a large three-car garage

    Julianna Flanders Flanders Real Estate

    88 & 90 Quenames Rd, Chilmark, MA 02535
  • /4

    $1,695,000

    • Land
    • 6.19 Acres
    • $273,829 per Acre

    19A Locust Ln Unit part of lot 175.1, Aquinnah, MA 02535

    This private 6.19 acres parcel has been approved for sub-division and not yet recorded. Potential to add acreage. Proposed lot lines and designated building envelope. Lovely rolling topography with mature trees. Septic & Well not installed

    Brenda Galligan Karen M. Overtoom R.E.

    19A Locust Ln Unit part of lot 175.1, Aquinnah, MA 02535
  • /34

    $1,599,000

    • 5 Beds
    • 2 Baths
    • 1,440 Sq Ft

    393 Lighthouse Rd, Aquinnah, MA 02535

    Ranch style home & Guest camp situated on 1+/- acre lot. The Main House offers distant views of Lobersterville beach and the Vineyard Sound beyond. Located in the desirable Lighthouse Road area, which offers walkable/close-by beach access and quiet roads. The view can be enjoyed from the Kitchen/Living/Dining as well as the wrap-around deck. Enjoy the open concept main living area, two bedrooms,

    Julianna Flanders Flanders Real Estate

    393 Lighthouse Rd, Aquinnah, MA 02535
  • /17

    $1,250,000

    • Land
    • 5.7 Acres
    • $219,298 per Acre

    14 Ridge Rd Unit 94, Aquinnah, MA 02535

    Idyllic gently rolling parcel of mixed hardwoods, meadow and stone walls awaits your vision. A large level building envelope has been cleared. A house and an ADU are permitted by right and a barn(subject to town approval) will fit nicely on this secluded parcel with room for a horse to graze and access nearby Land Bank and Sheriffs Meadow conservation land .It is walking distance to Menemsha

    Jim Wallen Feiner Real Estate

    14 Ridge Rd Unit 94, Aquinnah, MA 02535
  • /40

    $6,395,000

    • 8 Beds
    • 6.5 Baths
    • 6,921 Sq Ft

    19BC Locust Ln, Aquinnah, MA 02535

    This beautifully designed and built home is privately sited on 4.02 acres overlooking a pastoral setting with amazing ocean views and bordered by stone walls. There is also an additional 2.02 acre parcel included with purchase. The spacious entry hall steps into a formal living and dining room with oversized windows that take in the amazing North Shore ocean views, tall ceilings, a field stone

    Brenda Galligan Karen M. Overtoom R.E.

    19BC Locust Ln, Aquinnah, MA 02535
  • /35

    $2,850,000

    • 4 Beds
    • 3 Baths
    • 2,967 Sq Ft

    11 By the Woods, Chilmark, MA 02535

    Dreamlike Chilmark retreat on 4.5+/- acres overlooking the Chilmark Pond & Atlantic Ocean beyond. Uniquely designed with European and medieval history in mind. The House has 3 bedrooms, 3 bathrooms, an atrium dining area, a two-story library, a kitchen, and a pantry/wet bar. Charming garden and plantings surround the home.A must-see to appreciate all the special touches throughout the Main House,

    Julianna Flanders Flanders Real Estate

    11 By the Woods, Chilmark, MA 02535
  • /29

    $2,275,000

    • 2 Beds
    • 1.5 Baths
    • 1,176 Sq Ft

    9 Moshup Trail, Aquinnah, MA 02535

    Spectacular property in Aquinnah, featuring a newly installed and town-approved 6-bedroom septic system, ready to support your vision for expansion and renovation.Located on 4.7 acres filled with rolling meadows and stone walls, this property boasts a truly remarkable barn that was transported from Maine, and rebuilt on the Island. The grandfathered-in barn spans approximately 61' by 45' with

    Patrick McCarthy Grace Hagerty Real Estate Inc

    9 Moshup Trail, Aquinnah, MA 02535
  • /45

    $19,500,000

    • 7 Beds
    • 5.5 Baths
    • 3,344 Sq Ft

    104 & 111 Old Herring Creek Rd, West Tisbury, MA 02535

    This beautiful 2-parcel compound totals 9.5-acre of land and 600 feet of private Vineyard Sound beach. There is a renovated 4-bedroom beach cottage on one of the parcels which includes all modern amenities and offers spectacular views from almost every room. The second parcel has an older 3-bedroom home located high on a ridge. Both parcels offer wonderful walking paths to the sandy beach below.

    Thomas Leclair Landvest MV

    104 & 111 Old Herring Creek Rd, West Tisbury, MA 02535
  • /29

    $6,000,000

    • 3 Beds
    • 2 Baths
    • 2,710 Sq Ft

    35 S Bowl Rd, Chilmark, MA 02535

    This exceptionally elegant and tranquil home in Seven Gates Farm combines contemporary architectural design with timeless high-end features for Vineyard casual, nature-inspired living. Extraordinary and rare, this move-in ready three-bedroom home with six-bedroom septic system sits on an oversized 5.3-acre parcel in Chilmark. This thoughtful layout has an easy flow, soothing tones with cypress

    Meg Bodnar Tea Lane Associates

    35 S Bowl Rd, Chilmark, MA 02535
  • /39

    $1,669,000

    • 3 Beds
    • 4 Baths
    • 2,308 Sq Ft

    453 Lighthouse Rd, Aquinnah, MA 02535

    Aquinnah Retreat set on a private 1.1-acre lot! This beautiful single-family home was lovingly built and cared for by one family, offering peaceful surroundings and ocean views. Now move-in ready, it's the perfect place for new owners to relax and make it their own. The wrap-around deck provides a scenic spot to enjoy the coastal air. Inside, the kitchen and dining area are filled with natural

    We Close Deals Team Lamacchia Realty, Inc.

    453 Lighthouse Rd, Aquinnah, MA 02535
  • /52

    $12,500,000

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

    18 Spruce Gate Rd, Chilmark, MA 02535

    Welcome to an extraordinary ocean view coastal sanctuary set within the exclusive gates of Squibnocket Farm—a 450+ acre private community with access to over 2 miles of oceanfront, 1.5 miles of pond frontage, and 300+ acres of conservation land. Set on a peaceful, pastoral landscape abutting 17 acres of preserved land, this stately home was designed and built by Soikkeli & Company, one of the

    Alyssa Halisky Wallace & Co. Sotheby's

    18 Spruce Gate Rd, Chilmark, MA 02535

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