Vineyard Haven, MA Homes

/27
$1,200,000
- 2 Beds
- 2.5 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

Lisa Lucier

Anchor Realty of Martha's Vineyard

(508) 456-5742

70 Carol Ln, Oak Bluffs, MA 02557
/21
$9,500 per month plus fees
- 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
/35
$1,500,000 Sold Sep 22, 2025
- 2,336 Sq Ft
- $642/SF
- 277 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1980
8 Schoolhouse Village, Oak Bluffs, MA 02557

Located in a desirable Oak Bluffs neighborhood, surrounded by mature plantings and attractive, colorful landscaping, this property offers a pleasantly appointed 3-bedroom, 2.5-bath home and a recently renovated 1-bedroom, 1-bath apartment above the 2-car garage. The first floor features a spacious living room with a pellet stove and a fabulous great room with a wood-burning stove. French doors

Stephanie Roache Donnelly + Co.

8 Schoolhouse Village, Oak Bluffs, MA 02557

/3
Est $1,634,299 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

/39
$2,645,000 Pending
- 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

Wendy Harman

Compass

(508) 301-9323

31 The Blvd, Edgartown, MA 02539
/41
$13,500 per month plus fees
- 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
/2
$3,500,000 Sold Sep 12, 2025
- 3,656 Sq Ft
- $957/SF
- 0 Days On Market
- 8 Beds
- 3 Baths
- Built 1974
214 State Rd, Vineyard Haven, MA 02568

Not Listed in LINK.

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214 State Rd, Vineyard Haven, MA 02568

/36
Est $2,660,448 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

/32
$1,550,000 Pending
- 4 Beds
- 1.5 Baths
- 1,304 Sq Ft
11 John Wesley Ave, Oak Bluffs, MA 02568

East Chop Living in this 4 Bedroom Victorian home perched near the shoreline in Oak Bluffs-just a short stroll to the harbor, the shores of East Chop beaches, and the shops and restaurants of downtown Oak Bluffs. Built in 1905, and updated throughout the years, with its Victorian architecture softened by time and salt air, giving it an inviting, warm charm.The exterior features a wide

Lisa Lucier

Anchor Realty of Martha's Vineyard

(508) 682-5574

11 John Wesley Ave, Oak Bluffs, MA 02568
/41
$8,750 per month plus fees
- 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
/26
$1,450,000 Sold Sep 12, 2025
- 3,352 Sq Ft
- $433/SF
- 8 Days On Market
- 5 Beds
- 3 Baths
- Built 1975
48 Brewster Ave, Oak Bluffs, MA 02557

EAST CHOP - LOCATION- LOCATION . A RENOVATOR'S DREAM - A 5 bedroom multi-level home with an approved Title 5 septic system for 5 bedrooms - and just 1/2 mile to the harbor and town center. One lot from the East Chop Association Tennis Club. "You can change your house - but not your neighborhood" and this is a very special neighborhood. House needs much TLC - to be sold AS IS. Priced well

Patti Dean Wiggy's Pond Real Estate

48 Brewster Ave, Oak Bluffs, MA 02557

/21
Est $1,128,075 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

/22
$1,250,000
- 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
/14
$8,400 per month plus fees
- 4 Beds
- 3 Baths
- 2,148 Sq Ft
- House for Rent
39 Old Coach Rd, West Tisbury, MA 02568

Summer weekly rental only! June weekly rate is $8,400 and July weekly rate is $10,000/week - Sunday to Saturday. Recently renovated 4 bedroom, 3 bathroom home that sits on a private 2 acre lot in West Tisbury MA! This large cape house has just been update with new stainless steel appliances, new kitchen cabinets and countertops. Other updates include, new bathroom vanities and hardware,

Joseph D'Amico Dee Development Company

39 Old Coach Rd, West Tisbury, MA 02568
/21
$500,000 Sold Sep 12, 2025
- 604 Sq Ft
- $828/SF
- 58 Days On Market
- 1 Bed
- 1 Bath
- Built 1870
21 Rock Ave, Oak Bluffs, MA 02557

Experience the charm of 21 Rock Avenue, nestled in the Historic Martha's Vineyard Camp Meeting Association. This year-round cottage features 1 bedroom and 1 bath, and is just moments away from Oak Bluffs Harbor, ferry ports, sandy beaches, art galleries, and delightful restaurants. Recent exterior enhancements include cedar fencing, refreshed house trim, new paint, and an upgraded roof. Please

Marilyn Moses Ocean Park Realty Inc

21 Rock Ave, Oak Bluffs, MA 02557

/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

/21
$1,595,000
- 3 Beds
- 1 Bath
- 1,033 Sq Ft
9 Brunswick Ave, Oak Bluffs, MA 02557

PRIME LOCATION! LESS THAN A 5-MINUTE WALK TO OAK BLUFFS HARBOR! Beautifully Renovated in Oak Bluffs! This move-in ready home at 9 Brunswick Ave has been thoughtfully and extensively updated inside and out. Enjoy peace of mind with a new septic system, siding, windows, water line from the street, and upgraded electrical and plumbing. The interior boasts new flooring, insulation, fresh paint, a

Alice Pierce

Coldwell Banker Realty - Hingham

(508) 715-6242

9 Brunswick Ave, Oak Bluffs, MA 02557
/27
$21,700 per month plus fees
- 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
/40
$650,000 Sold Sep 10, 2025
- 759 Sq Ft
- $856/SF
- 251 Days On Market
- 2 Beds
- 0.5 Baths
- Built 1900
25 Oak Ave, Oak Bluffs, MA 02557

WALK TO THE HARBOR from this level 10,100 sq.ft. quarter acre lot set down a winding avenue off New York Avenue. Currently there's a very cute Victorian Era two story cottage which could be renovated. Alternatively, you have the choice to add on to the existing building or build a new FIVE (5) BEDROOM home - Possibly more than FIVE (5) bedrooms as it’s not in a Board of Health area of concern -

Alisan Lohan-Conway Alisan Lohan-Conway Properties

25 Oak Ave, Oak Bluffs, MA 02557

/37
Est $1,449,634 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

/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
/20
$14,000 per month plus fees
- 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
/18
$4,250,000 Sold Sep 09, 2025
- 4,125 Sq Ft
- $1,030/SF
- 21 Days On Market
- 5 Beds
- 3 Baths
- Built 1900
420 Lamberts Cove Rd, Vineyard Haven, MA 02568

Charming West Tisbury Estate with Waterfront on Seth's Pond. This stunning property offers the perfect blend of vintage charm and modern convenience, set against the tranquil backdrop of Seth's Pond. Featuring a main house, guest house, boathouse, and barn/workshop, this property provides a rare opportunity for both relaxation and recreation. The main house, a well maintained farmhouse dating

Alyssa Halisky Wallace & Co. Sotheby's International Realty

420 Lamberts Cove Rd, Vineyard Haven, MA 02568

/38
Est $1,035,943 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

/27
$1,649,000
- 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

(508) 691-8993

27 Chapde Ln, Tisbury, MA 02568
/30
$28,500 per month plus fees
- 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
/20
$1,295,000 Sold Sep 05, 2025
- 1,584 Sq Ft
- $818/SF
- 5 Days On Market
- 4 Beds
- 2 Baths
- Built 1988
2 Upper Douglas Ln, Oak Bluffs, MA 02557

Are you still looking for a year-round, island home for your family and only finding homes that are either not in your price range or are badly in need of renovation? Look no further because all that work has been done for you with this property. Just move in and enjoy the convenient location -- close to town, schools, hospital and public transportation. This low-maintenance, 4 bedroom, 2 bath

Lynn Buder Sandpiper Realty

2 Upper Douglas Ln, Oak Bluffs, MA 02557

/17
Est $1,589,900 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

/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

Lisa Lucier

Anchor Realty of Martha's Vineyard

(508) 514-5238

37 Circuit Ave Unit 4, Oak Bluffs, MA 02557
/10
$20,000 per month plus fees
- 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
/26
$965,000 Sold Sep 04, 2025
- 1,512 Sq Ft
- $638/SF
- 78 Days On Market
- 3 Beds
- 2 Baths
- Built 1998
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 1/2 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

Jason Parisella Keller Williams Realty Beverly

62 Jernegan Ave, Edgartown, MA 02539

/12
Est $1,304,936 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

/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

Lisa Lucier

Anchor Realty of MV

(508) 422-4131

37 Circuit Ave Unit 5, Oak Bluffs, MA 02557
/10
$8,500 per month plus fees
- 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
/35
$1,295,000 Sold Sep 02, 2025
- 1,814 Sq Ft
- $714/SF
- 3 Days On Market
- 3 Beds
- 2 Baths
- Built 1980
35 7th St N, Edgartown, MA 02539

Welcome to this charming Cape-style home, just a short distance from the Village. Set on a spacious half-acre lot, this delightful property has been lovingly maintained. The home features an open layout that seamlessly blends comfort and functionality, making it perfect for both everyday living and entertaining. A sun-filled living room with cathedral ceilings and sliders opens to a multi-level

Stephanie Roache Donnelly + Co.

35 7th St N, Edgartown, MA 02539

/13
Est $1,256,744 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

/34
$2,500,000
- 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

Lisa Lucier

Anchor Realty of MV

(508) 348-7972

34 Massasoit Ave, Oak Bluffs, MA 02568
/8
$11,800 per month plus fees
- 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
/28
$1,320,000 Sold Aug 29, 2025
- 1,450 Sq Ft
- $910/SF
- 6 Days On Market
- 3 Beds
- 2 Baths
- Built 1987
10 Eagles Nest, Edgartown, MA 02539

Nestled in the serene setting of the Dodger's Hole community, this home is brimming with natural light, soaring ceilings and clean architectural lines.The open-concept layout features a generous living area with a seamless flow to the dining, kitchen and entertaining spaces, ideal for both everyday living and hosting guests.Kitchen has brand new stainless steel appliances! The spaces are

Jennifer B. DaSilva Compass

10 Eagles Nest, Edgartown, MA 02539

/14
Est $999,034 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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