Dukes County MA Homes for Sale

/36
$869,000
- 1 Bed
- 1 Bath
- 797 Sq Ft
37 Circuit Ave Unit 5, Oak Bluffs, MA 02557

In the heart of Downtown Oak Bluffs Restless Winds Unit #5 comes with an amazing roof top deck shared with only one other condo (unit #4). You're in the middle of it all with this great location, yet you have easy access to a private and peaceful deck overlooking the town of Oak Bluffs and the surrounding waters. This incredible space takes you to another level of relaxation and a birds eye view

Lisa Lucier

Anchor Realty of Martha's Vineyard

(508) 544-0253

37 Circuit Ave Unit 5, Oak Bluffs, MA 02557
/31
$1,799,999
- 3 Beds
- 2 Baths
- 1,540 Sq Ft
43 N Slope Ln, Chilmark, MA 02535

Set on private 3.5-acre wooded parcel, this 3-bedroom, 2-bath single-family home offers the ultimate Martha’s Vineyard retreat. Nestled among mature trees, the property provides exceptional privacy and a peaceful natural setting, while remaining conveniently located to island villages, beaches, and amenities. The home is thoughtfully positioned to blend into its surroundings, featuring

Barbara O'Hara

NorthStar Real Estate, LLC

(508) 850-0854

43 N Slope Ln, Chilmark, MA 02535
/46
$899,000
- 2 Beds
- 1 Bath
- 990 Sq Ft
37 Circuit Ave Unit 4, Oak Bluffs, MA 02557

In the heart of Downtown Oak Bluffs- Restless Winds Condominium Unit #4 comes with an amazing roof top deck that is only shared with one other condo (#5). This spacious unit just under 1,000 sq. ft. has a ships feel with custom wood features and a ships ladder leading to the roof top deck. This condo packs a lot in with a full kitchen, living and dining area, a guest bedroom, a tiled bathroom

Lisa Lucier

Anchor Realty of Martha's Vineyard

(508) 546-9282

37 Circuit Ave Unit 4, Oak Bluffs, MA 02557
/19
$869,000 Coming Soon
- 1 Bed
- 1 Bath
- 990 Sq Ft
37 Circuit Ave Unit 4, Oak Bluffs, MA 02557

In the heart of Downtown Oak Bluffs- Restless Winds Condominium Unit #4 comes with an amazing roof top deck that is only shared with one other condo (#5). This spacious unit just under 1,000 sq. ft. has a ships feel with custom wood features and a ships ladder leading to the roof top deck. This condo packs a lot in with a full kitchen, living and dining area, a guest bedroom, a tiled bathroom

Lisa Lucier

Anchor Realty of MV

(508) 938-8096

37 Circuit Ave Unit 4, Oak Bluffs, MA 02557
/12
$1,495,000
- 4 Beds
- 4 Baths
- 2,304 Sq Ft
33 Alyssa Ln, Vineyard Haven, MA 02568

Country Living so close to Town! Lovely 4 Bedroom 2,304 sq ft Colonial Cape with Garage and lower level living space . Open kitchen, dining & entertainment area. Sliders open to Large side deck. High Ceilings Wood floors Living Room with additional nook. Half bath. Interior stairs to lower level with office/bedroom, half bath, private exterior entrance and garage. 2nd floor has large primary

Stephanie Burke

Portfolio Properties

(508) 687-6441

33 Alyssa Ln, Vineyard Haven, MA 02568
/26
$1,395,000
- 3 Beds
- 1 Bath
- 1,066 Sq Ft
17 Chapman La, Edgartown, MA 02539

Opportunity Knocks - Located within close proximity to Edgartown Village shops, restaurants, parks, and everyday conveniences, this fixer upper offers the rare chance to renovate in a location that truly shines. This property is full of potential for buyers, investors, or renovators looking to create something special. Bring your vision and transform this property into your signature retreat,

Wendy Harman

Compass

(508) 290-8074

17 Chapman La, Edgartown, MA 02539
/36
$5,325,000
- 6 Beds
- 4 Baths
- 2,890 Sq Ft
4 Canonicus Ave, Oak Bluffs, MA 02557

Overlooking Nantucket Sound and just steps from the vibrant heart of downtown Oak Bluffs, this distinctive compound blends laid-back West Coast style with classic island charm. The light-filled four-bedroom main house has been thoughtfully updated with modern, year-round comforts. Privately set at the rear, the guest house known as The Nest offers a peaceful retreat with a private deck, outdoor

Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

4 Canonicus Ave, Oak Bluffs, MA 02557
/23
$3,988,000
- 7 Beds
- 3.5 Baths
- 2,461 Sq Ft
69 School St, Edgartown, MA 02539

Located in the heart of Edgartown Village, this circa 1840 Greek Revival residence offers a rare opportunity to own a piece of island history on a coveted block. The property features a total of seven bedrooms across the main house and carriage house, making it a superb destination for family and guests. The main house features wide plank hardwood flooring and bright and sunny spaces with five

Peyton Wallace Studio Realty

69 School St, Edgartown, MA 02539
/23
$3,100,000
- 1 Bed
- 1 Bath
- 1,250 Sq Ft
114 Meeting House Way, Edgartown, MA 02539

3 Acre Katama Building Lot with Existing Guest House. This parcel is ready to be developed into a true Edgartown Compound. The last of three private, forested lots to be offered in this part of the Browns Farm Lane subdivision, two of which have already been sold and developed into breathtaking, substantial residences. Located one mile from Edgartown Great Pond and 2 miles from both South Beach

Rose Ryley Wallace & Co. Sotheby's International Realty

114 Meeting House Way, Edgartown, MA 02539
/42
$2,350,000
- 3 Beds
- 2.5 Baths
- 2,630 Sq Ft
81 Whalers Walk, Edgartown, MA 02539

Experience the ease of summer living in your own Martha’s Vineyard beach house. Perched atop a rise with sweeping views, abundant natural light, and star-filled skies, this furnished, move-in-ready home offers over 2,600 sq. ft. across four levels. A dramatic 30-foot vaulted foyer leads to a fully renovated chef’s kitchen with Sub-Zero refrigeration, premium stainless appliances, stone counters,

Dawn Bellante Sandpiper Realty, Inc.

81 Whalers Walk, Edgartown, MA 02539
/36
$4,500,000
- 4 Beds
- 3 Baths
- 2,715 Sq Ft
94 Weaver Ln, Vineyard Haven, MA 02568

Perched high above Lagoon Pond, this exceptional Martha's Vineyard estate offers a rare convergence of natural beauty, refined comfort, and Island living at its finest. Set on 2.25 secluded acres, panoramic views stretch across the shimmering waters, a private haven for kayaking, sailing, and peaceful exploration. Inside, four bedrooms and three full bathrooms are complemented by generous windows

Emma Kennedy Sandpiper Realty, Inc.

94 Weaver Ln, Vineyard Haven, MA 02568
/7
$4,500,000
- 15 Beds
- 12.5 Baths
- 7,250 Sq Ft
11 Macs Ln, Tisbury, MA 02568

A unique opportunity to own a one of a kind property complete with fourteen bedrooms, flanked with large picture windows and water views from all three living levels. Currently being run as a state licensed, private pay, assisted living facility. In addition to the fourteen bedrooms and twelve full baths and one half bath, in the main building, there is a private owners apartment on the first

Madelyn Silvia Wallace & Co. Sotheby's International Realty

11 Macs Ln, Tisbury, MA 02568
/46
$2,400,000
- 5 Beds
- 3.5 Baths
- 3,873 Sq Ft
50 Hidden Cove Rd, Edgartown, MA 02539

Sengekontacket–Walk into a “turn-key” opportunity in the desirable Hidden Cove community, just steps (.3 miles) from Sengekontacket Pond with access to State Beach and Nantucket Sound beyond. The lovingly-maintained 4 bedroom, 2.5 bath, 2 car garage main home sits high on the 1.5 acre property offering an abundance of natural light that flows into the open living and entertaining spaces. The

Sean Federowicz Landmarks at TODAY Real Estate

50 Hidden Cove Rd, Edgartown, MA 02539
/29
$2,600,000
- 3 Beds
- 1 Bath
- 1,336 Sq Ft
23 Circuit Avenue Extension, Oak Bluffs, MA 02557

Rare Opportunity with Endless Possibilities – Unmatched Harbor & Vineyard Sound Views.Location, Location, Location! A truly rare offering in the heart of Oak Bluffs, where properties like this seldom become available. Positioned directly across from the iconic Oak Bluffs Harbor, this property boasts unobstructed harbor views and sweeping vistas of Vineyard Sound—a setting that captures the

Rene Ben David Ocean Park Realty Inc

23 Circuit Avenue Extension, Oak Bluffs, MA 02557
/24
$2,925,000
- 5 Beds
- 4 Baths
- 3,704 Sq Ft
21 Davis St, Vineyard Haven, MA 02568

Ideally located just minutes from the heart of Vineyard Haven, 21 Davis Street offers exceptional island living in this beautifully crafted five-bedroom, four-bathroom home with 3,704 square feet of thoughtfully designed living space. Rich hardwood flooring, custom cabinetry, elegant Restoration Hardware vanities, and custom tilework throughout the bathrooms reflect the care and craftsmanship the

Paul Pertile The Agency

21 Davis St, Vineyard Haven, MA 02568
/39
$2,950,000
- 3 Beds
- 3.5 Baths
- 2,268 Sq Ft
23 Thaxter Ln, Edgartown, MA 02539

OPEN AND AIRY COASTAL RETREAT WITH EASY ACCESS TO SOUTH BEACH and EDGARTOWN VILLAGE. Welcome to this tri-level contemporary home in the heart of KATAMA. This home offers the perfect blend of spacious indoor-outdoor living with three levels of outdoor decking nestled amongst mature vegetation and a quick stroll to South Beach. The home features vaulted ceilings, two first floor bedroom en-suites,

Michele Casavant Vineyard Village Realty

23 Thaxter Ln, Edgartown, MA 02539
/12
$2,950,000
- 3 Beds
- 1 Bath
- 936 Sq Ft
9 N Neck Rd, Edgartown, MA 02539

COMMANDING WATER VIEWS ON CHAPPAQUIDDICK - This beloved fishing cottage rests high above one of the premier fishing areas on the island of Chappaquiddick. Set apart from the hustle and bustle of downtown, but within easy reach of all Edgartown offers, the pristine views over the wilds of Cape Pogue and the outer harbor bring peace and serenity for all who visit. Fishing, clamming, swimming,

Leslie C. Floyd Portfolio Properties

9 N Neck Rd, Edgartown, MA 02539
/42
$2,575,000
- 4 Beds
- 2.5 Baths
- 1,910 Sq Ft
76 Washque Ave, Edgartown, MA 02539

This stunning reverse-contemporary four-bedroom custom home is perfectly situated in one of Chappaquiddick's most sought-after locations. Designed with an expansive open-concept floor plan, the airy and inviting living area flows seamlessly onto a generous wraparound deck, where sweeping, bird's-eye views capture the natural beauty that surrounds you. Thoughtfully renovated, the home blends

Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

76 Washque Ave, Edgartown, MA 02539
/63
$2,999,000
- 8 Beds
- 7.5 Baths
- 3,770 Sq Ft
72 Chappaquiddick Ave, Edgartown, MA 02539

WELCOME to this turn-key CHAPPY COMPOUND! This property offers it ALL, with its Six (6) Bedroom, Five (5) bath Primary Home, Two (2) bedroom, Two (2) bath GUEST HOUSE, expansive POOL HOUSE with a bath, kitchenette, large lounge area topped with a cathedral ceiling, a WORKOUT & GAME BARN, a POOL, a VOLLEY BALL COURT and a TENNIS and PICKLEBALL COURT that has recently been resurfaced with the

Michele Casavant Vineyard Village Realty

72 Chappaquiddick Ave, Edgartown, MA 02539
/2
$2,700,000
- 4 Beds
- 4.5 Baths
- 2,750 Sq Ft
6 Laura's Way, Edgartown, MA 02568

Welcome to the opportunity to own a brand-new, GORGEOUS, custom-built home in Edgartown, set on a one-acre plot with a detached 900 sq ft accessory dwelling. The main residence opens to an inviting two-story foyer, leading to an expansive, living room featuring a wall of glass sliders. The gourmet kitchen is a chef’s dream, boasting Bosch appliances, a large quartz-topped island with seating for

Michele Casavant Vineyard Village Realty

6 Laura's Way, Edgartown, MA 02568
/4
$2,995,000
- 4 Beds
- 4.5 Baths
- 3,024 Sq Ft
9 Hagerty Dr, Tisbury, MA 02568

West Chop Dream Home in the Making! Experience the charm of this brand-new Shingle Style Colonial, currently under construction. Featuring 4 spacious bedrooms, 4 full and one half bath. This thoughtfully designed home offers generous space. Step outside into your private oasis, complete with an in-ground pool (36' x18') — perfect for sun-soaked afternoons and evening gatherings. Situated in a

Lisa Gilberto C McManus Realty Group

9 Hagerty Dr, Tisbury, MA 02568
/31
$2,395,000
- 4 Beds
- 3 Baths
- 1,918 Sq Ft
25 Fulling Mill Rd, Chilmark, MA 02535

Perched atop Fulling Mill Hill this distinctive contemporary main house plus guest house offers mid-century charm and a serene retreat set on 3.3 acres of mature oak and beech forest and bordered by an ancient stone wall. Designed by renowned Yale School of Architecture Dean Paul Mitarachi, the main house features a striking circular entryway framed by mature Asiatic gardens. Step inside to

Thomas Wallace Wallace & Co. Sotheby's

25 Fulling Mill Rd, Chilmark, MA 02535
/28
$2,950,000
- 4 Beds
- 3 Baths
- 2,927 Sq Ft
2 Bold Meadow Rd, Edgartown, MA 02539

Nestled on a private 1.7-acre parcel in the Bold Meadow neighborhood, this classic Cape offers a perfect blend of comfort and Vineyard charm. Surrounded by mature woodlands, association land, and State Forest, the property provides a serene retreat just moments from Edgartown. The main level is thoughtfully designed for both relaxation and entertaining, featuring a formal living room with a

Stacy Ickes Donnelly + Co.

2 Bold Meadow Rd, Edgartown, MA 02539
/65
$2,690,000
- 6 Beds
- 4 Baths
- 2,618 Sq Ft
55 Old House Way, West Tisbury, MA 02575

Lambert’s Cove/West Tisbury- custom-built contemporary farmhouse style. 4 bedrooms & 3 bathrooms in Main & 2 bedrooms & 1 bath Guest Cottage on 3 acres in a private neighborhood. Enter Main house from the covered porch -matching custom arch doors lead you to either the mudroom/laundry room-kitchen entry, or the living room. The kitchen has Mexican tiled floor & granite counters with stainless

Leslie Graham Anchor Realty of Martha's Vineyard

55 Old House Way, West Tisbury, MA 02575
/28
$2,495,000
- 4 Beds
- 3 Baths
- 2,600 Sq Ft
268 Tashmoo Ave, Vineyard Haven, MA 02568

Welcome to this meticulously maintained home which features an attractive open kitchen with an island that seats four. The kitchen has a wall of built in appliances and a walk-in pantry for ease of cooking. The kitchen flows into the open dining area and lounge area with a wall of sliding glass doors that lead to the large outdoor entertaining area which features a lounge area and two eating

Michele Casavant Vineyard Village Realty

268 Tashmoo Ave, Vineyard Haven, MA 02568
/66
$2,395,000
- 4 Beds
- 2.5 Baths
- 2,760 Sq Ft
69 Whalers Walk, Edgartown, MA 02539

EDGARTOWN – Beautifully landscaped property set on a lovely open, cleared lot with exceptional curb appeal, located just minutes from Downtown Edgartown and South Beach. This inviting home features many updates including a Tesla Solar Roof with a Tesla Powerwall, attached to Town Sewer with a SEVEN (7) bedroom sewer connection and an approval for a Two Car Garage with a detached bedroom above.

Alisan Lohan-Conway Alisan Lohan-Conway Properties

69 Whalers Walk, Edgartown, MA 02539
/39
$2,500,000
- 3 Beds
- 4 Baths
- 2,300 Sq Ft
229 Oak Ln, West Tisbury, MA 02575

A hidden gem in West Tisbury! Beautifully manicured, fenced in 2.2 - acre parcel with 100% privacy, and 84 evergreen trees. This modern, contemporary well maintained home is 3-bedroom, 3 bath with two levels of living and a partially finished basement. The first floor is a sunlight filled, open kitchen and dinning room, with hardwood floors throughout. There are multiple decks leading out to a

Doug Burke Cronigs Real Estate

229 Oak Ln, West Tisbury, MA 02575
/39
$3,995,000
- 8 Beds
- 6 Baths
- 4,651 Sq Ft
23 Beetle Swamp Rd, Edgartown, MA 02539

Sweetened Water Farm ~ Just off the main road, past an idyllic horse barn and conserved association land, you’ll find this eight-bedroom residence that sits prominently on 2.4 acres. The sprawling main house, an expanded classic Cape featuring separate living areas, both inside and out, and six bedrooms, including two first-floor en-suites, overlooks the rolling pastures with grazing horses.

Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

23 Beetle Swamp Rd, Edgartown, MA 02539
/30
$2,490,000
- 3 Beds
- 4 Baths
- 2,830 Sq Ft
42 Deacon Vincent Way, Edgartown, MA 02539

Katama ~ Easy Island Living in Edgartown Estates. Welcome to your Katama escape. Tucked away on a quiet, paved road in Edgartown Estates, this easygoing home is all about enjoying the best of Vineyard life. Hop on the bike path and you’re just minutes to South Beach or downtown Edgartown—perfect for beach days, ice cream runs, and everything in between.Inside, the home is bright and

Stephanie Roache Donnelly + Co

42 Deacon Vincent Way, Edgartown, MA 02539
/30
$2,950,000
- 3 Beds
- 2.5 Baths
- 1,845 Sq Ft
33 Ocean Ave, Oak Bluffs, MA 02557

A rare offering on iconic Ocean Park. This beautifully renovated Victorian cottage sits in the heart of historic Oak Bluffs with unencumbered views of Ocean Park and Vineyard Sound. Completely rebuilt in 2024, this 3-bedroom, home blends classic Vineyard charm with modern comforts, featuring a welcoming wraparound porch, a beach-stone wood-burning fireplace, new kitchen, baths, windows, doors and

Marcia Sullivan Garvey Donnelly + Co.

33 Ocean Ave, Oak Bluffs, MA 02557
/40
$2,790,000
- 3 Beds
- 3.5 Baths
- 2,898 Sq Ft
4 Pip'N Rd, Edgartown, MA 02539

Where Chappaquiddick’s natural beauty meets Edgartown sophistication, this impeccably maintained custom home offers thoughtful design and exceptional livability. The professionally styled interior features an inviting foyer, a gracious dining room open to a living room with fireplace and glass doors to the deck, and a gourmet kitchen with island and banquette. A sun porch, wet bar, powder room,

Lesley Heidt Sandpiper Realty, Inc.

4 Pip'N Rd, Edgartown, MA 02539
/32
$560,000
- 1 Bed
- 1.5 Baths
- 590 Sq Ft
21 Island Inn Rd Unit 39G, Oak Bluffs, MA 02568

Own a piece of the Vineyard dream with a fully furnished, beautifully updated condo perfectly designed for comfort and vacation living at the Island Inn Country Club in Oak Bluffs. The location is just off Beach Road, a short distance to beaches, downtown Circuit Ave, and a lovely drive along Beach Road to Edgartown Village. The bike path, public transportation, and a popular restaurant with live

Diana Gilmore Island Real Estate

21 Island Inn Rd Unit 39G, Oak Bluffs, MA 02568
/5
$1,200,000
- Land
- 0.9 Acre
- $1,333,333 per Acre
87 Whalers Walk Unit 113, Edgartown, MA 02539

Rare opportunity to own a buildable .9-acre parcel (Lot#113) with the ability to connect to town sewer, allowing up to seven bedrooms. In a tranquil residential neighborhood, ideally located near Morning Glory Farm, the bike paths to Edgartown Village, South Beach, and up-island. Purchase independently or combine with the neighboring 5-bedroom, 2,630 s/f home on .92 acres(Lot#114), which also has

Dawn Bellante-Holand Sandpiper Realty

87 Whalers Walk Unit 113, Edgartown, MA 02539
/28
$950,000
- 2 Beds
- 2 Baths
- 1,583 Sq Ft
25 Vineyard Meadow Farms Rd, West Tisbury, MA 02575

Prime Martha’s Vineyard location! Nestled on 1.4 acres in the sought-after Vineyard Meadow Farms neighborhood, this property offers an exceptional combination of privacy, convenience, and potential. Ideally situated in West Tisbury, close to Edgartown and Vineyard Haven, residents enjoy easy access to local shops, restaurants, and amenities, as well as the island’s most beautiful

Maranda Post Compass LLC

25 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
/7
$3,100,000
- Land
- 3.04 Acres
- $1,019,737 per Acre
114 Meeting House Way, Edgartown, MA 02539

3 Acre Katama Building Lot with Existing Guest House.This parcel is ready to be developed into a true Edgartown Compound. The last of three private, forested lots to be offered in this part of the Browns Farm Lane subdivision, two of which have already been sold and developed into breathtaking, substantial residences. Located one mile from Edgartown Great Pond and 2 miles from both South

Rose Ryley Wallace & Co. Sotheby's

114 Meeting House Way, Edgartown, MA 02539
/53
$6,750,000
- 5 Beds
- 3.5 Baths
- 4,050 Sq Ft
78 Hammett Rd, Chilmark, MA 02535

Wonderful elevated Chilmark north shore 3.8 acre secure waterfront property with dramatic year round sunset water views to the Gay Head Lighthouse and Elizabeth Islands. The Vineyard Sound expanse enjoys peaceful sailing, fishing and other boating activity to enhance the ocean splendor. The 5 bedroom 3 1/2 bath 4,050 sq ft home is literally in move-in condition. Architect designed and built by

Robert Kenney Tea Lane Associates

78 Hammett Rd, Chilmark, MA 02535
/4
$625,000
- Land
- 0.34 Acre
- $1,815,277 per Acre
0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568

Oak Bluffs Buildable Lot – Prime Location. This flat 2-bedroom building lot is ideally located just moments from the Hudson Avenue access to scenic Lagoon Pond, with easy access to both Farm Neck Golf Club and downtown Oak Bluffs. Situated in a neighborhood of newly constructed homes, this lot presents an excellent opportunity to become part of a growing community in Oak Bluffs. According to the

Andrew McElhinney Compass LLC

0-A California Ave Unit Part lot 79, Oak Bluffs, MA 02568
/9
$2,450,000
- Land
- 5.37 Acres
- $456,238 per Acre
9 Maqua Way, Edgartown, MA 02539

Chappaquiddick: Beautiful 5-acre parcel offering private frontage on Katama Bay. The generous-sized lot affords plenty of development flexibility, with the ability to capture the view from nearly any location. Located on Maqua Way, a quiet subdivision just off the paved road, the property is conveniently situated near all the Chappy favorites: beaches, trails, a community center, and Slip Away

Katherine Donahue Sandpiper Realty Inc

9 Maqua Way, Edgartown, MA 02539
/15
$2,490,000
- Land
- 7.2 Acres
- $345,833 per Acre
3 Jacobs Neck Road (North Lot 1) Unit 2, Edgartown, MA 02539

Build your dream home on the special 7.2 acre North lot 1 private wooded property with 1/2 ownership in the beautiful 4.5 acre meadow in the grand Boldwater Association(BWA) on the glorious Edgartown Great Pond with approx. 3,000 ft of private barrier beach. BWA is 40 homesites on 450 acres with 150 acres of conservation abutting another 1,500 acres of conservation and a few large estates - all

Robert Kenney Tea Lane Associates

3 Jacobs Neck Road (North Lot 1) Unit 2, Edgartown, MA 02539
/43
$14,500,000
- 4 Beds
- 4.5 Baths
- 3,705 Sq Ft
64 Squibnocket Farm Rd, Chilmark, MA 02535

Welcome to an extraordinary waterfront retreat, where luxury meets nature perfectly. This exclusive property offers unparalleled access to breathtaking views, serene landscapes, and the soothing sounds of water lapping against the shore. Squibnocket Farm Road is renowned for its unspoiled beauty and tranquility. This sophisticated gated community offers a sense of seclusion while remaining within

Thomas Wallace Wallace & Co. Sotheby's

64 Squibnocket Farm Rd, Chilmark, MA 02535

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