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Vineyard Haven, MA Homes for Sale

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  • 34 Massasoit Ave, Oak Bluffs, MA 02568
    34 Massasoit Ave, Oak Bluffs, MA 02568
    34 Massasoit Ave, Oak Bluffs, MA 02568
    /28

    $2,999,000

    • 6 Beds
    • 2.5 Baths
    • 1,666 Sq Ft

    34 Massasoit Ave, Oak Bluffs, MA 02568

    This is the last B1 undeveloped commercial property on Circuit Avenue's main strip. Previous development plans included mixed use with commercial store front and condos above. Located on the corner of Circuit Ave and Massasoit this property has an existing Victorian home with 6 bedrooms, and 3.5 bathrooms, perfect for a weekly rental or employee housing. Right in the heart of Oak Bluffs walk to

    Agent Photo

    Lisa Lucier

    Anchor Realty of MV

    (508) 348-7972

    34 Massasoit Ave, Oak Bluffs, MA 02568
  • 70 Carol Ln, Oak Bluffs, MA 02557
    70 Carol Ln, Oak Bluffs, MA 02557
    70 Carol Ln, Oak Bluffs, MA 02557
    /45

    $1,250,000

    • 2 Beds
    • 3 Baths
    • 1,500 Sq Ft

    70 Carol Ln, Oak Bluffs, MA 02557

    Oak Bluffs location that is central to everything down Island. Situated on a 1/3 acre lot this ranch home with a finished basement has been recently renovated. The first floor has 1500 sq feet with of a large open kitchen, dining area, and living room with plenty of room for large gatherings. The primary bedroom has a bathroom on suite. Another bedroom has easy access to the hall bath. The

    Agent Photo

    Lisa Lucier

    Anchor Realty of Martha's Vineyard

    (508) 456-5742

    70 Carol Ln, Oak Bluffs, MA 02557
  • 62 Jernegan Ave, Edgartown, MA 02539
    62 Jernegan Ave, Edgartown, MA 02539
    62 Jernegan Ave, Edgartown, MA 02539
    /27

    $1,250,000

    • 3 Beds
    • 2 Baths
    • 1,512 Sq Ft

    62 Jernegan Ave, Edgartown, MA 02539

    Charming 3-Bedroom, 2-Bath Ranch in Edgartown – Spacious, Private, and Conveniently Located Discover this inviting 3-bedroom, 2 full bath ranch-style home set on a generous .5 acre lot in a quiet, private area of Edgartown. Featuring an open-concept layout, this home offers seamless flow between the living, dining, and kitchen spaces—ideal for both everyday living and entertaining. The spacious

    Agent Photo

    Nicholas Silvestri

    Keller Williams Realty Evolution

    (508) 290-4981

    62 Jernegan Ave, Edgartown, MA 02539
  • 385 Barnes Rd, Vineyard Haven, MA 02568
    385 Barnes Rd, Vineyard Haven, MA 02568
    385 Barnes Rd, Vineyard Haven, MA 02568
    /42

    $5,995,000

    • 3 Beds
    • 6 Baths
    • 3,608 Sq Ft

    385 Barnes Rd, Vineyard Haven, MA 02568

    Indulge in luxurious living at this exquisite waterfront retreat featuring a private 125-foot sandy beach. Over 5,400 sq ft on three floors blend elegance with indoor-outdoor living. The grand foyer leads to dramatic interiors with high ceilings and floor-to-ceiling windows showcasing stunning water views. Highlights include a striking stone fireplace, custom built-ins, gourmet kitchen with stone

    Agent Photo

    Wendy Harman

    Compass

    (508) 274-5363

    385 Barnes Rd, Vineyard Haven, MA 02568
  • 174 Tashmoo Ave, Vineyard Haven, MA 02568
    174 Tashmoo Ave, Vineyard Haven, MA 02568
    174 Tashmoo Ave, Vineyard Haven, MA 02568
    /38

    $2,495,000

    • 5 Beds
    • 4.5 Baths
    • 3,213 Sq Ft

    174 Tashmoo Ave, Vineyard Haven, MA 02568

    Welcome to your dream home! The perfect blend of comfort and luxury awaits you in this custom-designed 5-bedroom, 4.5-bathroom residence. With over 3200 square feet of spacious living, upscale furnishings, finished basement with entertainment bar, and all the right touches to make every day feel like a retreat. Conveniently located under a half mile from downtown Vineyard Haven, where you will

    Agent Photo

    Lisa Lucier

    Anchor Realty of MV

    (508) 901-2347

    174 Tashmoo Ave, Vineyard Haven, MA 02568
  • 31 The Blvd, Edgartown, MA 02539
    31 The Blvd, Edgartown, MA 02539
    31 The Blvd, Edgartown, MA 02539
    /37

    $2,995,000

    • 3 Beds
    • 2 Baths
    • 1,350 Sq Ft

    31 The Blvd, Edgartown, MA 02539

    Waterfront Charmer on Sengekontacket Pond - Perched on the shoreline, this contemporary cottage is enveloped by stone walls, lush gardens, and stunning water views. Inside, a bright, airy living space features an open dining area and a well-appointed kitchen. The all-white interior is complemented by hardwood floors, vaulted ceilings, skylights, air conditioning, and ceiling fans. Three sliding

    Agent Photo

    Wendy Harman

    Compass

    (508) 301-9323

    31 The Blvd, Edgartown, MA 02539
  • 27 Chapde Ln, Tisbury, MA 02568
    27 Chapde Ln, Tisbury, MA 02568
    27 Chapde Ln, Tisbury, MA 02568
    /27

    $1,695,000

    • 3 Beds
    • 2.5 Baths
    • 1,740 Sq Ft

    27 Chapde Ln, Tisbury, MA 02568

    Classic Style Meets Timeless Charm - Located at the end of a lightly traveled lane and surrounded by stunning gardens and stone retaining walls, this residence provides a modern and spacious environment for comfortable island living. The home welcomes you with an open and bright layout, featuring sleek finishes and an abundance of natural light. The gourmet kitchen is a chef's delight that

    Agent Photo

    Wendy Harman

    Compass

    (508) 691-8993

    27 Chapde Ln, Tisbury, MA 02568
  • 37 Circuit Ave Unit 4, Oak Bluffs, MA 02557
    37 Circuit Ave Unit 4, Oak Bluffs, MA 02557
    37 Circuit Ave Unit 4, Oak Bluffs, MA 02557
    /32

    $985,000

    • 2 Beds
    • 1 Bath
    • 990 Sq Ft

    37 Circuit Ave Unit 4, Oak Bluffs, MA 02557

    Downtown Oak Bluffs Located right in the heart of town. Unit #4 A penthouse condo with a semi-private rooftop deck (shared with unit 5 only). This spacious condo has a panoramic view of the town and surrounding waters sitting high above it all with outdoor seating and separate entrances from either condo. This solid deck adds a whole other dimension to this already desirable unit.The interior

    Agent Photo

    Lisa Lucier

    Anchor Realty of Martha's Vineyard

    (508) 514-5238

    37 Circuit Ave Unit 4, Oak Bluffs, MA 02557
  • 37 Circuit Ave Unit 5, Oak Bluffs, MA 02557
    37 Circuit Ave Unit 5, Oak Bluffs, MA 02557
    37 Circuit Ave Unit 5, Oak Bluffs, MA 02557
    /24

    $935,000

    • 1 Bed
    • 1 Bath
    • 797 Sq Ft

    37 Circuit Ave Unit 5, Oak Bluffs, MA 02557

    Downtown Oak Bluffs centrally located in the heart of Oak Bluffs. Steps from ferries, shops, restaurants and beaches from this penthouse condo. Escape the hustle and bustle on your semi private rooftop deck shared only with (unit 4 also for sale). Panoramic views of the Nantucket and Vineyard Sounds await you while you relax on the deck or enjoy dinner al fresco. The condo features all wood

    Agent Photo

    Lisa Lucier

    Anchor Realty of MV

    (508) 422-4131

    37 Circuit Ave Unit 5, Oak Bluffs, MA 02557
  • 56 Bridle Path Rd, Vineyard Haven, MA 02568
    56 Bridle Path Rd, Vineyard Haven, MA 02568
    56 Bridle Path Rd, Vineyard Haven, MA 02568
    /52

    $2,200,000

    • 3 Beds
    • 3 Baths
    • 2,526 Sq Ft

    56 Bridle Path Rd, Vineyard Haven, MA 02568

    COMING SOON: Showing can begin June 8th. POOL AND LUSH GARDENS Situated on three acres and abutting nearly 25 acres of conservation land, this well-crafted home offers the perfect blend of tranquility and convenience.Step inside to discover over 2,500 square feet of thoughtfully designed living space, filled with natural light. The bright and inviting living room, complete with a cozy fireplace,

    Tina Miller Compass | Point B

    56 Bridle Path Rd, Vineyard Haven, MA 02568
  • 5 Bayes Hill Cir, Vineyard Haven, MA 02568
    5 Bayes Hill Cir, Vineyard Haven, MA 02568
    5 Bayes Hill Cir, Vineyard Haven, MA 02568
    /46

    $2,150,000

    • 4 Beds
    • 2.5 Baths
    • 2,855 Sq Ft

    5 Bayes Hill Cir, Vineyard Haven, MA 02568

    On a quiet cul-de-sac in the Bayes Hill neighborhood is this spacious traditional Colonial-style home adorned with charm. As you enter the home from the idyllic covered porch, you are welcomed into the foyer. The home is filled with intimate spaces while offering the opportunity for larger parties to gather. The living room has built-in shelving that flank the gas fireplace and it is connected to

    Michele Moore Island Real Estate

    5 Bayes Hill Cir, Vineyard Haven, MA 02568
  • 5 Pine Tree Ln, Vineyard Haven, MA 02568
    5 Pine Tree Ln, Vineyard Haven, MA 02568
    5 Pine Tree Ln, Vineyard Haven, MA 02568
    /32

    $2,395,000

    • 4 Beds
    • 3 Baths
    • 2,730 Sq Ft

    5 Pine Tree Ln, Vineyard Haven, MA 02568

    Blending 1920s charm with modern luxury, this beautifully renovated home is tucked away in the sought-after West Chop area of Vineyard Haven. Just steps from the neighborhood beach on the pristine shores of Vineyard Sound, this elegant seaside retreat offers the perfect mix of historic character and contemporary comfort.Inside, a thoughtfully designed floor plan welcomes you with generous living

    Alyssa Halisky Wallace & Co. Sotheby's

    5 Pine Tree Ln, Vineyard Haven, MA 02568
  • 15 Crowell Ln, Tisbury, MA 02568
    15 Crowell Ln, Tisbury, MA 02568
    15 Crowell Ln, Tisbury, MA 02568
    /25

    $3,390,000

    • 3 Beds
    • 2.5 Baths
    • 1,514 Sq Ft

    15 Crowell Ln, Tisbury, MA 02568

    Hickory Hollow is one of the most enchanting parcels of land in Seven Gates Farm. You enter the property and feel as if you have stepped back in time. The cozy antique farmhouse is the centerpiece of the 6.8-acre property which includes rolling lawns, lichen-covered stone walls and boulders, numerous specimen trees, and no fewer than 3 ponds. In addition to the main house there are 3 additional

    Mark Jenkins Wallace & Co. Sotheby's International Realty

    15 Crowell Ln, Tisbury, MA 02568
  • 16 Atlantic Ave, Oak Bluffs, MA 02557
    16 Atlantic Ave, Oak Bluffs, MA 02557
    16 Atlantic Ave, Oak Bluffs, MA 02557
    /39

    $2,495,000

    • 4 Beds
    • 1.5 Baths
    • 2,577 Sq Ft

    16 Atlantic Ave, Oak Bluffs, MA 02557

    East Chop - Tucked away on a quiet lane just moments from the iconic East Chop Lighthouse and breathtaking bluff views, this timeless retreat invites you to embrace the slower pace of island life. The main residence is a stately four-bedroom, classic summer home, rich in character and nostalgic charm. At the rear of the property, a one-bedroom guest house provides privacy and, perhaps most

    Katherine Donahue Sandpiper Realty Inc

    16 Atlantic Ave, Oak Bluffs, MA 02557
  • 111 Eastville Ave, Oak Bluffs, MA 02557
    111 Eastville Ave, Oak Bluffs, MA 02557
    111 Eastville Ave, Oak Bluffs, MA 02557
    /41

    $2,748,000

    • 6 Beds
    • 4 Baths
    • 2,400 Sq Ft

    111 Eastville Ave, Oak Bluffs, MA 02557

    Not to be missed!! Steps to the beach- Minutes to downtown Oak Bluffs and Vineyard Haven. This is a perfect location.FULLY FURNISHED, TURNKEY, with an impressive rental history. Situated on an oversized lot that is two parcels away from the beach. This home offers six bedrooms and four

    Ed Charter Arrowhead Homes

    111 Eastville Ave, Oak Bluffs, MA 02557
  • 23 Circuit Avenue Extension, Oak Bluffs, MA 02557
    23 Circuit Avenue Extension, Oak Bluffs, MA 02557
    23 Circuit Avenue Extension, Oak Bluffs, MA 02557
    /28

    $3,100,000 Open Sat 11AM - 2PM

    • 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 very

    Rene Ben David Ocean Park Realty Inc

    23 Circuit Avenue Extension, Oak Bluffs, MA 02557
  • 10 Wood Duck Way, Oak Bluffs, MA 02557
    10 Wood Duck Way, Oak Bluffs, MA 02557
    10 Wood Duck Way, Oak Bluffs, MA 02557
    /42

    $2,500,000

    • 4 Beds
    • 3.5 Baths
    • 1 Sq Ft

    10 Wood Duck Way, Oak Bluffs, MA 02557

    Perched on a hill, this waterfront house encompasses three levels of living. Thoughtfully designed and well cared for, this home provides calming water views and direct access to Wiggy's freshwater Pond from almost every room. The main level boasts a kitchen fitted with high-end appliances and opens to the dining room, deck, and airy living room with exposed beams, a gas fireplace, and large

    Marcia Sullivan Garvey Donnelly + Co.

    10 Wood Duck Way, Oak Bluffs, MA 02557
  • 47 E East Chop Dr Unit 5, Oak Bluffs, MA 02557
    47 E East Chop Dr Unit 5, Oak Bluffs, MA 02557
    47 E East Chop Dr Unit 5, Oak Bluffs, MA 02557
    /16

    $1,495,000

    • 1 Bed
    • 1 Bath
    • 650 Sq Ft

    47 E East Chop Dr Unit 5, Oak Bluffs, MA 02557

    East Chop Waterfront Luxury Cond -- This 1-BR, 1st floor, waterfront condominium, the ''Captain's Quarters'', features outstanding water views of the harbor and sound beyond, private entrance, cathedral ceilings and is just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown. In pristine condition, the unit includes new kitchen with Bosch appliances, living

    Perry Patterson MV Luxury Homes, LLC

    47 E East Chop Dr Unit 5, Oak Bluffs, MA 02557
  • 47 E Chop Dr Unit 2, Oak Bluffs, MA 02568
    47 E Chop Dr Unit 2, Oak Bluffs, MA 02568
    47 E Chop Dr Unit 2, Oak Bluffs, MA 02568
    /13

    $1,495,000

    • 1 Bed
    • 1 Bath
    • 736 Sq Ft

    47 E Chop Dr Unit 2, Oak Bluffs, MA 02568

    East Chop Water Front Luxury Condominium -- This 1-bedroom, waterfront condominium, ''Cottage City'', features outstanding water views of the harbor and sound beyond, a cozy propane fireplace and is just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown. In pristine condition, this 1st-floor unit includes new kitchen with Bosch appliances, living room with

    Perry Patterson MV Luxury Homes, LLC

    47 E Chop Dr Unit 2, Oak Bluffs, MA 02568
  • 47 E Chop Dr Unit 1, Oak Bluffs, MA 02568
    47 E Chop Dr Unit 1, Oak Bluffs, MA 02568
    47 E Chop Dr Unit 1, Oak Bluffs, MA 02568
    /12

    $1,495,000

    • 1 Bed
    • 1 Bath
    • 731 Sq Ft

    47 E Chop Dr Unit 1, Oak Bluffs, MA 02568

    East Chop Water Front Luxury Condominium -- This 1-bedroom, 1st floor, waterfront condominium, ''Oak Bluffs'', features outstanding water views of the harbor and sound beyond. Located just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown, this unit includes new kitchen with Bosch appliances, living room, dining area and a private covered front porch

    Perry Patterson MV Luxury Homes, LLC

    47 E Chop Dr Unit 1, Oak Bluffs, MA 02568
  • 4 Dempster Park, Oak Bluffs, MA 02568
    4 Dempster Park, Oak Bluffs, MA 02568
    4 Dempster Park, Oak Bluffs, MA 02568
    /30

    $2,285,000

    • 4 Beds
    • 2.5 Baths
    • 1,825 Sq Ft

    4 Dempster Park, Oak Bluffs, MA 02568

    This handsome, meticulously maintained 4-bedroom gambrel roof house, nestled in one of the prime locations of East Chop, has had substantial renovations and upgrades over the years since 2017. First floor includes large living room with dining area and Rumford wood burning fireplace that opens out to a front porch and deck running the length of the house and which wraps around to the rear patio.

    Perry Patterson MV Luxury Homes LLC

    4 Dempster Park, Oak Bluffs, MA 02568
  • 22 Greenleaf Ave, Oak Bluffs, MA 02557
    22 Greenleaf Ave, Oak Bluffs, MA 02557
    22 Greenleaf Ave, Oak Bluffs, MA 02557
    /37

    $2,390,000

    • 3 Beds
    • 2 Baths
    • 1,608 Sq Ft

    22 Greenleaf Ave, Oak Bluffs, MA 02557

    Tucked away on one of Oak Bluffs' most sought-after streets, Fairview on Greenleaf Avenue offers an extraordinary location with stunning views of Sunset Lake, Oak Bluffs Harbor, and Nantucket Sound. From the highest point on Greenleaf, enjoy vibrant sunrises and a front-row seat to the town's iconic fireworks.This home blends classic Vineyard character with thoughtful design by Island architect

    Jennifer O'hanlon Compass

    22 Greenleaf Ave, Oak Bluffs, MA 02557
  • 47 E Chop Dr Unit 5, Oak Bluffs, MA 02568
    47 E Chop Dr Unit 5, Oak Bluffs, MA 02568
    47 E Chop Dr Unit 5, Oak Bluffs, MA 02568
    /17

    $1,495,000

    • 1 Bed
    • 1 Bath
    • 650 Sq Ft

    47 E Chop Dr Unit 5, Oak Bluffs, MA 02568

    East Chop/Oak Bluffs waterfront -- The ultimate in waterfront living experiences, this 1-bedroom, waterfront condominium unit, the "Captain's Quarters", features outstanding water views of the harbor and sound beyond, private entrance, cathedral ceilings and is just steps from the tennis club, beaches, restaurants, ferries to the mainland and downtown. In pristine condition, the unit includes new

    Perry Patterson MV Luxury Homes

    47 E Chop Dr Unit 5, Oak Bluffs, MA 02568
  • 22 Greenleaf Ave, Oak Bluffs, MA 02539
    22 Greenleaf Ave, Oak Bluffs, MA 02539
    22 Greenleaf Ave, Oak Bluffs, MA 02539
    /39

    $2,390,000

    • 3 Beds
    • 2 Baths
    • 1,608 Sq Ft

    22 Greenleaf Ave, Oak Bluffs, MA 02539

    Tucked away on one of the most sought-after streets in Oak Bluffs, Fairview on Greenleaf Avenue offers an extraordinary location steeped in history and charm. With unparalleled views stretching across Sunset Lake, Oak Bluffs Harbor, and Nantucket Sound, this property captures the essence of coastal living on Martha’s Vineyard. From the highest vantage point on Greenleaf, enjoy sunrises that fill

    Jen O'Hanlon Compass | The O'Hanlon Group

    22 Greenleaf Ave, Oak Bluffs, MA 02539
  • 10 Bridge Ln, Vineyard Haven, MA 02568
    10 Bridge Ln, Vineyard Haven, MA 02568
    10 Bridge Ln, Vineyard Haven, MA 02568
    /43

    $2,195,000

    • 3 Beds
    • 4 Baths
    • 2,512 Sq Ft

    10 Bridge Ln, Vineyard Haven, MA 02568

    This thoughtfully designed post and beam home blends craftsmanship with character, featuring artistic touches throughout that make it truly one-of-a-kind. The kitchen flows beautifully between the main living areas and an inviting dining space surrounded by windows offering access to one of several outdoor decks for effortless indoor-outdoor living. On the first floor, the primary suite includes

    Jill Napior Tea Lane Associates

    10 Bridge Ln, Vineyard Haven, MA 02568
  • 79 Circuit Ave, Oak Bluffs, MA 02557
    79 Circuit Ave, Oak Bluffs, MA 02557
    79 Circuit Ave, Oak Bluffs, MA 02557
    /57

    $2,300,000

    • 4 Beds
    • 4 Baths
    • 3,076 Sq Ft

    79 Circuit Ave, Oak Bluffs, MA 02557

    Wonderful opportunity to reimagine this historic classic Victorian home located at the gateway to the Oak Bluffs Business district with a gorgeous, secluded garden and 5 off street parking spaces the property lends itself to a single-family home or conversion to a multi-family. The home has been both of these configurations in previous years. The current layout offers incredible opportunities

    kyle Neyer Tea Lane Associates

    79 Circuit Ave, Oak Bluffs, MA 02557
  • 2 Farm Path, Oak Bluffs, MA 02557
    2 Farm Path, Oak Bluffs, MA 02557
    2 Farm Path, Oak Bluffs, MA 02557
    /37

    $1,995,000

    • 4 Beds
    • 3 Baths
    • 3,058 Sq Ft

    2 Farm Path, Oak Bluffs, MA 02557

    "Turn-key" offering! This custom cape design with a delightful farmer's porch provides ample opportunities to entertain. Set upon nearly an acre of level and landscaped land with irrigation, it abuts the State Forrest, has an open floor plan with cathedral ceilings and skylights. The three bedroom main, has A/C, a finished basement rec room, a large rear deck that spills forth onto a large yard

    Sean Federowicz Landmarks at TODAY Real Estate

    2 Farm Path, Oak Bluffs, MA 02557
  • 30 Sengekontacket Rd, Oak Bluffs, MA 02557
    30 Sengekontacket Rd, Oak Bluffs, MA 02557
    30 Sengekontacket Rd, Oak Bluffs, MA 02557
    /22

    $2,295,000

    • 4 Beds
    • 3 Baths
    • 2,262 Sq Ft

    30 Sengekontacket Rd, Oak Bluffs, MA 02557

    Secluded island retreat nestled above the trees! Located in the desirable Sengekontacket Association, this four-bedroom, three-bathroom home offers stunning views of acres of conservation land, Sengekontacket Pond, and Nantucket Sound. Perched on a hillside, the house provides utmost privacy from all rooms while being just a short walk from the Association boat ramp and kayak storage.The main

    Cassie Courtney Wallace & Co. Sotheby's

    30 Sengekontacket Rd, Oak Bluffs, MA 02557
  • 126 Border Rd, Vineyard Haven, MA 02568
    126 Border Rd, Vineyard Haven, MA 02568
    126 Border Rd, Vineyard Haven, MA 02568
    /31

    $2,000,000

    • 3 Beds
    • 3 Baths
    • 2,251 Sq Ft

    126 Border Rd, Vineyard Haven, MA 02568

    Designed and built by the owner's architect father, Nembhard N. Culin in 1975. The unique mid-century style house is perfectly sited on a knoll overlooking the head of Lagoon Pond. Follow the private path to the sandy beach for walking, swimming, kayaking or boating. The property includes a permitted boat mooring and the beach is perfect for launching small boats. The house was built as a

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

    126 Border Rd, Vineyard Haven, MA 02568
  • 5 Pine Tree Ln, Vineyard Haven, MA 02568
    5 Pine Tree Ln, Vineyard Haven, MA 02568
    5 Pine Tree Ln, Vineyard Haven, MA 02568
    /30

    $2,395,000

    • 4 Beds
    • 3 Baths
    • 2,730 Sq Ft

    5 Pine Tree Ln, Vineyard Haven, MA 02568

    Blending 1920s charm with modern luxury, this beautifully renovated home is tucked away in the sought-after West Chop area of Vineyard Haven. Just steps from the neighborhood beach on the pristine shores of Vineyard Sound, this elegant seaside retreat offers the perfect mix of historic character and contemporary comfort. Inside, a thoughtfully designed floor plan welcomes you with generous living

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    5 Pine Tree Ln, Vineyard Haven, MA 02568
  • 30 Franklin Ave, Oak Bluffs, MA 02568
    30 Franklin Ave, Oak Bluffs, MA 02568
    30 Franklin Ave, Oak Bluffs, MA 02568
    /24

    $2,150,000

    • 2 Beds
    • 2.5 Baths
    • 2,137 Sq Ft

    30 Franklin Ave, Oak Bluffs, MA 02568

    Welcome to your dream home! This stunning new construction boasts a coastal feel throughout and is situated on a spacious corner lot. Inside, you'll find luxurious finishes, including Thermador appliances and quartz countertops in the gourmet kitchen including a large pantry with beverage refrigerator. The elegance continues with white oak floors throughout the home. With 2 bedrooms and 2.5

    Stacy Ickes Donnelly + Co.

    30 Franklin Ave, Oak Bluffs, MA 02568
  • 46 Red Buoy Ln, Tisbury, MA 02568
    46 Red Buoy Ln, Tisbury, MA 02568
    46 Red Buoy Ln, Tisbury, MA 02568
    /24

    $2,095,000

    • 4 Beds
    • 4 Baths
    • 2,413 Sq Ft

    46 Red Buoy Ln, Tisbury, MA 02568

    Nestled in Vineyard Haven, 46 Red Buoy Lane is an exquisite and sophisticated home completed in 2022. This residence offers 4 bedrooms and 3.5 bathrooms and spans a generous 1,816 square feet. The property's unique offering of a one-bedroom apartment in the basement is noteworthy, providing an additional 597 square feet of living space. The main level boasts a thoughtfully designed floor plan

    Andrew McElhinney Compass LLC

    46 Red Buoy Ln, Tisbury, MA 02568
  • 30 Franklin Ave, Oak Bluffs, MA 02568
    30 Franklin Ave, Oak Bluffs, MA 02568
    30 Franklin Ave, Oak Bluffs, MA 02568
    /26

    $2,150,000 New Construction

    • 2 Beds
    • 3 Baths
    • 2,137 Sq Ft

    30 Franklin Ave, Oak Bluffs, MA 02568

    Welcome to your dream home! This stunning new construction boasts a coastal feel throughout and is situated on a spacious corner lot. Inside, you'll find luxurious finishes, including Thermador appliances and quartz countertops in the gourmet kitchen including a large pantry with beverage refrigerator. The elegance continues with white oak floors throughout the home. With 2 bedrooms and 2.5

    Stacy Ickes Donnelly + Co

    30 Franklin Ave, Oak Bluffs, MA 02568
  • 33 Lagoon Pond Rd, Vineyard Haven, MA 02568
    33 Lagoon Pond Rd, Vineyard Haven, MA 02568
    33 Lagoon Pond Rd, Vineyard Haven, MA 02568
    /38

    $2,295,000 New Construction

    • 3 Beds
    • 3 Baths
    • 1,680 Sq Ft

    33 Lagoon Pond Rd, Vineyard Haven, MA 02568

    Discover this stunning newly contructed single-family home in the heart of downtown Vineyard Haven. This beautifully crafted 3-bedroom, 3-bathroom residence offers high-end finishes and thoughtful design throughout.The modern kitchen and bathrooms feature elegant quartz countertops, while tile showers with custom glass enclosures add a touch of luxury. Each bedroom includes spacious walk-in

    Mike Sawyer Sawyer Realty Group

    33 Lagoon Pond Rd, Vineyard Haven, MA 02568
  • 118 William St, Vineyard Haven, MA 02568
    118 William St, Vineyard Haven, MA 02568
    118 William St, Vineyard Haven, MA 02568
    /52

    $4,495,000

    • 4 Beds
    • 5 Baths
    • 2,792 Sq Ft

    118 William St, Vineyard Haven, MA 02568

    The Captain George Harding Home sits gracefully on the westerly side of iconic William Street overlooking Vineyard Haven village with distant views of the harbor. This immaculate and re-imagined Gothic Revival offers both timeless elegance and modern luxury. Completed in 2024, the comprehensive down-to-the-studs renovation includes all new systems like central air and dehumidification. Every

    Alexis Holden Tea Lane Associates

    118 William St, Vineyard Haven, MA 02568
  • 150 E Chop Dr, Oak Bluffs, MA 02557
    150 E Chop Dr, Oak Bluffs, MA 02557
    150 E Chop Dr, Oak Bluffs, MA 02557
    /42

    $12,400,000

    • 8 Beds
    • 9 Baths
    • 8,560 Sq Ft

    150 E Chop Dr, Oak Bluffs, MA 02557

    Big Bluff. The crown jewel of East Chop. Timeless elegance and unmatched craftsmanship on the shores of Martha’s Vineyard. Renowned architect M. Hutker and preeminent builder J.G.Early teamed up to create this magnificent waterfront estate. 8,500 Sq. ft. of pure luxury. Open-concept living with large picture windows, a chef’s kitchen with island, high-end appliances, wet bar, and sunlit breakfast

    Moira Lown Coldwell Banker Realty - Wellesley

    150 E Chop Dr, Oak Bluffs, MA 02557
  • 208 Irenes Way, Tisbury, MA 02568
    208 Irenes Way, Tisbury, MA 02568
    208 Irenes Way, Tisbury, MA 02568
    /18

    $1,525,000

    • 4 Beds
    • 3 Baths
    • 2,961 Sq Ft

    208 Irenes Way, Tisbury, MA 02568

    Welcome to this 4 bedroom 3 bathroom 2,961 square foot home! Enjoy the open, first floor layout, finished walk out basement, beautiful hardwood flooring and a quality kitchen with new granite countertops. Just off of the kitchen there is a convenient first floor bedroom, bathroom and laundry room, as well as a lovely bonus space currently enjoyed as a sunroom with a sliding door to the large

    Emma Kiley Bryant Landmarks at TODAY Real Estate

    208 Irenes Way, Tisbury, MA 02568
  • 20 James Pond Way, Vineyard Haven, MA 02568
    20 James Pond Way, Vineyard Haven, MA 02568
    20 James Pond Way, Vineyard Haven, MA 02568
    /37

    $3,995,000

    • 5 Beds
    • 3 Baths
    • 2,791 Sq Ft

    20 James Pond Way, Vineyard Haven, MA 02568

    Nestled on a serene 4.5-acre parcel of land off Lambert's Cove Road, this exquisite property offers unparalleled privacy, views and direct access to James Pond and beyond to the Land Bank's Lambert's Cove Beach property. In addition to the custom heated Gunite pool, the expansive yard provides space for many outdoor activities while relishing the tranquility of the location. The residence

    Sheila Morse Island Real Estate

    20 James Pond Way, Vineyard Haven, MA 02568
  • 7 Candlemaker Cir, Edgartown, MA 02539
    7 Candlemaker Cir, Edgartown, MA 02539
    7 Candlemaker Cir, Edgartown, MA 02539
    /3

    $1,795,000

    • 3 Beds
    • 4 Baths
    • 2,312 Sq Ft

    7 Candlemaker Cir, Edgartown, MA 02539

    3 bedroom 2.5 bath main house consisting of 2 separate living spaces. First unit has 1st floor with livingroom, kitchen and bathroom. The second floor has an additional livingroom with two bedrooms. The second unit has 1st floor living area with kitchenette and bathroom, bedroom is in basement with walkout egress. 2 Car Garage has a permitted finished living space above with livingroom, full

    Roy Cutrer Jr Laer Realty Partners

    7 Candlemaker Cir, Edgartown, MA 02539
  • 7 Candle Maker Cir, Edgartown, MA 02539
    7 Candle Maker Cir, Edgartown, MA 02539
    7 Candle Maker Cir, Edgartown, MA 02539
    /3

    $1,795,000

    • 3 Beds
    • 3.5 Baths
    • 2,311 Sq Ft

    7 Candle Maker Cir, Edgartown, MA 02539

    3 bedroom 2.5 bath main house consisting of 2 separate living spaces. First unit has 1st floor with livingroom, kitchen and bathroom. The second floor has an additional livingroom with two bedrooms. The second unit has 1st floor living area with kitchenette and bathroom, bedroom is in basement with walkout egress. 2 Car Garage has a permitted finished living space above with livingroom, full

    Roy Cutrer LAER Realty Partners

    7 Candle Maker Cir, Edgartown, MA 02539

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