Vineyard Haven, MA Homes

/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

Wendy Harman

Compass

(508) 205-8817

385 Barnes Rd, Vineyard Haven, MA 02568
/21
$9,500 total monthly price
- 4 Beds
- 2 Baths
- 1,579 Sq Ft
- House for Rent
155 Skiff Ave, Vineyard Haven, MA 02568

**SUMMER RENTAL ONLY** RATE IS WEEKLY** Enjoy the serenity of a four bedroom, two full bathroom peaceful oasis complete with private in-ground pool. Close to lively dining and boutiques of downtown Vineyard Haven. Unwind at neighborhood beaches; Eastville, Owen Park, Tashmoo beaches all just a few minutes drive from your vacation retreat.This lovely home spread over 1600ft of living area provides

Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

155 Skiff Ave, Vineyard Haven, MA 02568
/28
$1,400,000 Sold Nov 26, 2025
- 1,592 Sq Ft
- $879/SF
- 126 Days On Market
- 4 Beds
- 1.5 Baths
- Built 1968
5 Scottys Ln, Vineyard Haven, MA 02568

BUYER PAID FOR NEW SEPTIC AND BUYER BROKER FEE. Attention Developers and Island Lovers! Take note of this rare opportunity in a prime West Tisbury Location. This mid-century home with excellent bones fronts on Seth's Pond, a beloved locale perfect for swimming, paddle-boarding, and kayaking. 5 Scotty's Lane has an existing 4-bedroom main house with the first floor and lower walk-out level

Idalyn Macchia Gilstad Wallace & Co. Sotheby's

5 Scottys Ln, Vineyard Haven, MA 02568

/3
Est $1,637,771 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,329 Sq Ft
18 Towanticut Ave, Oak Bluffs, MA 02557

18 Towanticut Ave, Oak Bluffs, MA 02557

/34
$2,250,000
- 6 Beds
- 2.5 Baths
- 1,666 Sq Ft
34 Massasoit Ave, Oak Bluffs, MA 02568

Downtown Oak Bluffs an investment opportunity awaits at the top of Circuit Ave. Dual zoned this is two properties in one. An existing 6 bedroom 3.5 bath Victorian home in the popular Copeland District a couple blocks to the beach even closer to restaurants shops and entertainment. On town sewer it's ideal for weekly rentals. The other side of the property facing Circuit Ave. is zoned Commercial

Lisa Lucier

Anchor Realty of MV

(508) 715-8624

34 Massasoit Ave, Oak Bluffs, MA 02568
/41
$13,500 total monthly price
- 5 Beds
- 5.5 Baths
- 3,000 Sq Ft
- House for Rent
14 Bernard Cir, Vineyard Haven, MA 02568

** SUMMER WEEKLY RATE ** Private and luxurious BRAND NEW contemporary chic 5 BED 5.5 BATH home perfectly situated close to downtown Vineyard Haven yet set amongst a rural and peaceful WEST CHOP adjacent neighborhood. Indulge and unwind in the PRIVATE HEATED SALTWATER IN-GROUND POOL surrounded by opulent outdoor living and dining area highlighted by covered al-fresco kitchen, BBQ grill and bar -

Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

14 Bernard Cir, Vineyard Haven, MA 02568
/23
$1,575,000 Sold Nov 24, 2025
- 1,666 Sq Ft
- $945/SF
- 223 Days On Market
- 4 Beds
- 2 Baths
- Built 1997
60 Windsor Dr, Edgartown, MA 02539

Welcome to your ideal Edgartown retreat! This stunning classic cape-style home features four bedrooms and two baths. Built and cared for by a contractor, this residence exudes quality and attention to detail at every turn. Nestled on a picturesque half-acre lot in the Westminster Acres neighborhood, privacy abounds in this tranquil setting. Situated on a quiet paved dead-end street, enjoy easy

Alyssa Halisky Wallace & Co. Sotheby's International Realty

60 Windsor Dr, Edgartown, MA 02539

/36
Est $2,458,974 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 3,470 Sq Ft
28 Woodhaven Dr, Edgartown, MA 02539

28 Woodhaven Dr, Edgartown, MA 02539

/27
$1,200,000
- 2 Beds
- 2.5 Baths
- 1,500 Sq Ft
70 Carol Ln, Oak Bluffs, MA 02557

Charming Renovated Ranch in the Heart of Oak Bluffs Discover the perfect blend of comfort, convenience, and coastal charm in this beautifully renovated ranch home, ideally located in a central Oak Bluffs neighborhood close to everything down-Island. Set on a spacious 1/3-acre lot, this property offers both privacy and proximity — just minutes from the Oak Bluffs School, town center, and all the

Lisa Lucier

Anchor Realty of Martha's Vineyard

(508) 456-5742

70 Carol Ln, Oak Bluffs, MA 02557
/41
$8,750 total monthly price
- 4 Beds
- 2.5 Baths
- 1,811 Sq Ft
- House for Rent
11 High Meadow Ln, Vineyard Haven, MA 02568

**SUMMER WEEKLY RATE ** INQUIRE FOR LONG TERM OFFSEASON RATE**Discover the perfect summer retreat in this beautifully updated Meadow View Farms home. Nestled on a private hilltop and minutes from beaches, bike paths, Farm Neck Gand Downtown Oak Bluffs, this home offers a serene escape close to the island’s best attractions. 4 spacious bedrooms, first floor primary ensuite, shared secondary floor

Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

11 High Meadow Ln, Vineyard Haven, MA 02568
/51
$2,500,000 Sold Nov 21, 2025
- 4,982 Sq Ft
- $502/SF
- 83 Days On Market
- 5 Beds
- 4.5 Baths
- Built 1987
79 David Ave, Vineyard Haven, MA 02568

BEAUTIFUL CUSTOM-BUILT RETREAT- LAMBERT'S COVE This impressive property offers the perfect blend of privacy and convenient access to downtown and the picturesque James Pond Reserve at Lambert's Cove Beach. Step inside to discover over 4,900 sq ft of recently renovated living space. The home boasts 5 bedrooms and 4.5 bathrooms, including a stunning chef's kitchen that will ignite your culinary

Tina Miller Donnelly + Co

79 David Ave, Vineyard Haven, MA 02568

/21
Est $1,080,742 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,176 Sq Ft
10 Lagoon Rd, Oak Bluffs, MA 02557

10 Lagoon Rd, Oak Bluffs, MA 02557

/20
$1,100,000 Pending
- 2 Beds
- 2.5 Baths
- 2,128 Sq Ft
1 Jessie Leigh Mitchell Way, Oak Bluffs, MA 02557

Welcome to this spacious and well-appointed home offering 2,128 square feet of comfortable living space, nestled on a generous 0.49-acre lot. Perfect for both everyday living and entertaining, this residence features beautiful hardwood floors throughout the first floor, with wall to wall carpet in the second floor bedrooms adding warmth and timeless appeal. The large open-concept kitchen is the

Lisa Lucier

Anchor Realty of Martha's Vineyard

(508) 827-6851

1 Jessie Leigh Mitchell Way, Oak Bluffs, MA 02557
/27
$21,700 total monthly price
- 5 Beds
- 3 Baths
- 2,168 Sq Ft
- House for Rent
97 3rd St N, Edgartown, MA 02539

YOUR VINEYARD ESCAPE AWAITS! This sizable vintage rental with water views of Sengekontacket Pond and beyond is ideal for your island getaway. Boasting multiple levels of living and porches that take advantage of views, the main floor is awash in seaside tones. Display a raw bar on the center island and top off beverages in the kitchen before relaxing in the sunroom as you enjoy the painterly sky

Fine Homes Group Keller Williams Realty Boston-Metro | Back Bay

97 3rd St N, Edgartown, MA 02539
/39
$2,495,000 Sold Nov 20, 2025
- 2,694 Sq Ft
- $926/SF
- 161 Days On Market
- 4 Beds
- 6 Baths
- Built 2016
16 Mockingbird Dr, Edgartown, MA 02539

Experience the ultimate Vineyard getaway in this custom Colonial that perfectly balances sophistication with Island charm. This thoughtfully designed property features soaring 9-foot ceilings, authentic Heart Pine flooring, and a show-stopping gourmet kitchen complete with professional-grade Viking appliances, handcrafted soapstone countertops, and a statement Carrara marble island. The spacious

Emma Kennedy Sandpiper Realty Inc

16 Mockingbird Dr, Edgartown, MA 02539

/31
Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,754 Sq Ft
12 Fairway Dr, Vineyard Haven, MA 02568

12 Fairway Dr, Vineyard Haven, MA 02568

/27
$1,615,000
- 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

Wendy Harman

Compass

(774) 515-4591

27 Chapde Ln, Tisbury, MA 02568
/22
$20,000 total monthly price
- 5 Beds
- 3 Baths
- 3,000 Sq Ft
- House for Rent
55 Samoset Ave, Oak Bluffs, MA 02557

Modernized 5 bed, 3 full bath Victorian in the heart of Downtown Oak Bluffs. Steps to restaurants, shopping, harbor, ferries and beaches. Accommodates 10 guests. Easy breezy outdoor living, dining, bluestone patio and BBQ grill. Relax on the covered porch surrounded by a lush flower garden or unwind in the outdoor shower. Updated stone and stainless kitchen. Formal dining for eight. A/C, WIFI and

Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

55 Samoset Ave, Oak Bluffs, MA 02557
/13
$2,237,500 Sold Nov 19, 2025
- 2,299 Sq Ft
- $973/SF
- 120 Days On Market
- 4 Beds
- 3 Baths
- Built 1974
26 Chappaquiddick Avenue and Passamaquoddy Ave, West Tisbury, MA 02575

Discover the rare opportunity to build your dream home in one of the island’s most sought-after locations off Lamberts Cove Road. This parcel offers year-round waterfront living with the ultimate blend of privacy, beach access, and design potential, without the usual coastal erosion concerns. Approved architectural plans by Moskow Linn Architects are in place for a four-bedroom main residence, a

Jill Napior Tea Lane Associates

26 Chappaquiddick Avenue and Passamaquoddy Ave, West Tisbury, MA 02575

/37
Est $1,464,307 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,754 Sq Ft
12 Fairway Dr, Oak Bluffs, MA 02557

12 Fairway Dr, Oak Bluffs, MA 02557

/22
$1,199,000
- 2 Beds
- 1 Bath
- 742 Sq Ft
47 Winemack St, Oak Bluffs, MA 02557

Oak Bluffs -East Chop-Close to the ocean. Two cottages on one lot. Stay in one and rent the other, the possibilities are great with this amazing opportunity to own close to the beach and just a mile to Oak Bluffs center. The front house is two bedrooms 1 bath: freshly painted with new flooring. The second home nestled in the back of the lot is an open floor plan with one bedroom, one bath, and a

Lisa Lucier

Anchor Realty of MV

(508) 403-9601

47 Winemack St, Oak Bluffs, MA 02557
/30
$28,500 total monthly price
- 9 Beds
- 6.5 Baths
- 3,500 Sq Ft
- House for Rent
9 Tuckernuck Ave, Oak Bluffs, MA 02557

**SHORT TERM ONLY - WEEKLY RATE ADVERTISED ** Water view Victorian fronting Waban Park, steps to Inkwell Beach. Newly restored 9-bed, 6+ bath Main and Guest House houses 18 guests. Internet, A/C and cable TV. Coastal chic interior with all new furnishings. Large open floor plan, ample gathering and relaxation spaces. Dining for 10, Wet Bar, gourmet kitchen, gas range, stainless appliances and

Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

9 Tuckernuck Ave, Oak Bluffs, MA 02557
/34
$3,746,925 Sold Nov 14, 2025
- 2,861 Sq Ft
- $1,310/SF
- 114 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1974
39 Sengekontacket Rd, Edgartown, MA 02539

SPECTACULAR WATERFRONT home with stunning water views from every room. Situated in a private location in the Sengekontacket Association, this is an exceptional property in a rare setting. Completely renovated in 2014. In addition to the breathtaking water view of Major's Cove and of Felix Neck throughout the home, the front of the property faces serene pastoral views. This home offers four

Jayne Isford Ocean Park Realty Inc

39 Sengekontacket Rd, Edgartown, MA 02539

/38
Est $975,891 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,120 Sq Ft
287 County Rd, Vineyard Haven, MA 02568

287 County Rd, Vineyard Haven, MA 02568

/46
$1,299,000
- 3 Beds
- 3 Baths
- 1,750 Sq Ft
185 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568

Experience sun-drenched living in one of Tashmoo Woods’ mostdesirable floor plans. This beautifully maintained 3-bedroom, 3-bath home offers full accessto the coveted Tashmoo Woods amenities, including a pristine pool andpool house, multiple tennis courts, a children’s play area, a privatelaunch on Lake Tashmoo, and a beautiful Association beach on theSound. Inside, soaring

Candy DaRosa Feiner Real Estate

185 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568
/10
$20,000 total monthly price
- 5 Beds
- 3 Baths
- 2,352 Sq Ft
- House for Rent
55 Samoset Ave Unit 1, Oak Bluffs, MA 02557

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Newly renovated, Great for Family Gatherings, Corporate Retreats, Central Air & Heat, very close to Circuit Ave and Beach, 5 Bedrooms, 3 full baths, galley kitchen, new appliances, dining room, family room, Flat Screen TV, FREE Wifi, washer & dryer, bay window breakfast nook, Oak and Pine wood flooring, outdoor shower, wrap around porch, blue stone

Karen Overtoom Karen M. Overtoom R.E.

55 Samoset Ave Unit 1, Oak Bluffs, MA 02557
/30
$815,000 Sold Nov 14, 2025
- 907 Sq Ft
- $899/SF
- 100 Days On Market
- 3 Beds
- 1 Bath
- Built 1870
17 Siloam Ave, Oak Bluffs, MA 02557

PRISTINE YEAR ROUND COTTAGE RENOVATED THROUGHOUT ~Welcome to 17 Siloam Avenue, a delightful cottage nestled in the historic Martha’s Vineyard Camp Meeting Association, offering spectacular sunset views of Sunset Lake and the distant harbor from its inviting porches. The current owners have cherished this home year-round for 13 years, and it’s easy to see why. This spacious residence features an

Marilyn Moses Ocean Park Realty Inc

17 Siloam Ave, Oak Bluffs, MA 02557

/17
Est $1,518,651 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,298 Sq Ft
19 Quantapog Rd, Vineyard Haven, MA 02568

19 Quantapog Rd, Vineyard Haven, MA 02568

/50
$1,900,000
- 4 Beds
- 3 Baths
- 2,056 Sq Ft
20 Brook Hollow Rd, Vineyard Haven, MA 02568

This spacious custom designed home is well sited to offer maximum privacy in the lush area of Long View. A short bike ride to Lambert's Cove beach, it's also about a 20-minute walk down a quiet private road. The home lays out well for family and extended guests with a roomy living room boasting vaulted ceilings and large windows. The house is designed to have an intimate relationship with the

Jim Feiner Feiner Real Estate

20 Brook Hollow Rd, Vineyard Haven, MA 02568
/8
$17,500 total monthly price
- 8 Beds
- 4.5 Baths
- 3,876 Sq Ft
- House for Rent
550 Chappaquonsett Rd Vh424 Unit 1, Tisbury, MA 02568

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!!!!!! Classic vineyard cottage with large open indoor and outdoor spaces to choose from while you and your family create memories to last a lifetime. Enjoy creating appetizers or three course meals in the newly renovated kitchen, bask in the light filled sun room or one of several covered porches while you take in the smell of fresh ocean air and

Karen Overtoom Karen M. Overtoom R.E.

550 Chappaquonsett Rd Vh424 Unit 1, Tisbury, MA 02568
/9
$160,000 Sold Nov 14, 2025
- 381 Sq Ft
- $420/SF
- 0 Days On Market
- 1 Bed
- 1 Bath
- Built 1958
60 Beach Rd Unit 105, Vineyard Haven, MA 02568

Not Listed in LINK

Nantucket CompLINK LINK

60 Beach Rd Unit 105, Vineyard Haven, MA 02568

/12
Est $1,158,830 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,997 Sq Ft
3 Carole Ave, Vineyard Haven, MA 02568

3 Carole Ave, Vineyard Haven, MA 02568

/3
$2,100,000
- 3 Beds
- 3.5 Baths
- 2,019 Sq Ft
2 Hope's Way, Oak Bluffs, MA 02557

ESTEEMED BUILDER READY to BREAK GROUND! Purchase this exceptional lot in Lagoon Ridge and start building your ISLAND DREAM 3 BR 3.5 home today! Purchase lot ($700,000)& Execute a BUILDING CONTRACT ($1,400,000 )or choose your own builder... Call for details and schedule a tour! Welcome to Oak Bluffs’ newest and most sought-after neighborhood, where you can construct your 3-bedroom home on a lofty

Marilyn Moses Ocean Park Realty Inc

2 Hope's Way, Oak Bluffs, MA 02557
/10
$8,500 total monthly price
- 3 Beds
- 2 Baths
- House for Rent
29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575

THIS IS A WEEKLY RENTAL PROPERTY!! Red Farm, Off Lambert's Cove Road West Tisbury. This newly built Contemporary Home is privately sited overlooking a peaceful meadow and wooded setting. The spacious floor plan features an open living, dining and a well equipped chef's kitchen, cathedral ceilings, wood floors and sliders that lead to a nicely landscaped yard. Three spacious bedrooms, the primary

Karen Overtoom Karen M. Overtoom R.E.

29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575
/33
$839,000 Sold Nov 14, 2025
- 939 Sq Ft
- $894/SF
- 12 Days On Market
- 2 Beds
- 1 Bath
- Built 1870
16 Cottage Park, Oak Bluffs, MA 02557

Just steps from the iconic Tabernacle and Trinity Park, this charming cottage is nestled in the heart of the historic Martha's Vineyard Camp Meeting Association—a designated National Historic Landmark District. Surrounded by colorful gardens and picturesque pedestrian walkways, it offers an easy stroll to Oak Bluffs Harbor, beaches, ferries, art galleries, restaurants, and all the vibrant charm

Marilyn Moses Ocean Park Realty Inc

16 Cottage Park, Oak Bluffs, MA 02557

/13
Est $1,166,677 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,428 Sq Ft
33 Menahan St, Vineyard Haven, MA 02568

33 Menahan St, Vineyard Haven, MA 02568

/28
$2,295,000
- 4 Beds
- 3.5 Baths
- 2,690 Sq Ft
151 Tashmoo Ave, Vineyard Haven, MA 02568

The Colonial Style home with wrap around porch is beautifully maintained and nicely sited on almost a half acre. The first floor is thoughtfully designed and offers an open floor plan that includes an ample mudroom with half bath and is just off the side porch that takes you into the well equipped kitchen with a center island, stainless appliances, custom cabinetry and dining room with sliders to

Brenda Galligan Karen M. Overtoom R.E.

151 Tashmoo Ave, Vineyard Haven, MA 02568
/8
$11,800 total monthly price
- 4 Beds
- 4 Baths
- 2,612 Sq Ft
- House for Rent
46 Buttonwood Farm Rd Unit 1, West Tisbury, MA 02575

THIS IS A WEEKLY RENTAL PROPERTY!! Beautifully updated contemporary home with impeccably landscaped lawns and gardens, a swimming pond and hot tub with two outdoor showers - one enclosed and one open to the hot tub and patio area on the side of the house. Gorgeous back deck with outdoor dining accessible through sliding glass doors from the dining room. Inside, enjoy the fully equipped and

Karen Overtoom Karen M. Overtoom R.E.

46 Buttonwood Farm Rd Unit 1, West Tisbury, MA 02575
/19
$750,000 Sold Nov 07, 2025
- 1,154 Sq Ft
- $650/SF
- 14 Days On Market
- 4 Beds
- 1 Bath
- Built 1867
41 Trinity Park, Oak Bluffs, MA 02557

Step back in time with this quintessential Martha’s Vineyard Campground Cottage, nestled in the heart of Wesleyan Grove. The cottage captures the spirit of the Island’s rich history, with its storybook architecture, vibrant community setting, and proximity to all that Oak Bluffs has to offer. The cottage features classic Victorian-era details, starting with its inviting front porch. The

Stacy Ickes Donnelly + Co.

41 Trinity Park, Oak Bluffs, MA 02557

/14
Est $971,167 Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,024 Sq Ft
51 Manchester Ave, Vineyard Haven, MA 02568

51 Manchester Ave, Vineyard Haven, MA 02568

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Massachusetts Dukes County Vineyard Haven

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