Vineyard Haven, MA Houses for Sale

/21
$1,695,000
- 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
/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
/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

Wendy Harman

Compass

(508) 691-8993

27 Chapde Ln, Tisbury, 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
/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
/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
/34
$3,450,000
- 4 Beds
- 3 Baths
- 1,728 Sq Ft
6 Brewster Ave, Oak Bluffs, MA 02557

Enjoy sweeping ocean views from this beautifully updated East Chop Victorian, complete with a timeless guest cottage. Thoughtfully renovated in 2010, the main residence seamlessly blends historic character with modern comfort. The kitchen and bathrooms have been stylishly updated while preserving the home's original charm and character. The guest cottage, tucked to the rear of the property,

Katherine Donahue Sandpiper Realty Inc

6 Brewster Ave, Oak Bluffs, MA 02557
/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
/51
$2,750,000 Open Tue 11AM - 1PM
- 5 Beds
- 4.5 Baths
- 4,982 Sq Ft
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
/42
$2,750,000
- 5 Beds
- 4.5 Baths
- 4,982 Sq Ft
79 David Ave, Vineyard Haven, MA 02568

BEAUTIFUL CUSTOM-BUILT RETREAT – LAMBERT’S COVE This impressive 4,900+ sq ft home offers privacy with easy access to downtown and James Pond Reserve at Lambert’s Cove Beach. Featuring 5 bedrooms, 4.5 baths, and a stunning chef’s kitchen, perfect after trips to local farm stands. Enjoy multiple living areas—oversized family/media room, dining room, sunny living room, and game room. Outdoor

Tina Miller Donnelly + Co.

79 David Ave, Vineyard Haven, MA 02568
/52
$3,750,000
- 5 Beds
- 6.5 Baths
- 4,372 Sq Ft
139 Main St, Vineyard Haven, MA 02568

Nestled just two blocks from Vineyard Haven's working harbor, 139 Main Street is a quietly grand in-town property with the feel of a private estate. Once two separate addresses--now gracefully combined into a single half-acre parcel--this home offers rare space, privacy, and timeless character in one of the island's most approachable villages. From the moment you step through the welcoming

Leslie Floyd Portfolio Properties

139 Main St, Vineyard Haven, MA 02568
/42
$2,125,000
- 3 Beds
- 4 Baths
- 2,558 Sq Ft
35 Tower Ridge Rd, Oak Bluffs, MA 02557

Thoughtfully designed post-and-beam home that blends character with modern comfort and flexible living in Tower Ridge. The open-concept main floor features spacious gathering areas, while the finished basement offers a quiet retreat for work, relaxation, or play. The outdoor living space is just as inviting, with an oversized deck overlooking mature plantings and a generous side yard--perfect for

Katherine Donahue Sandpiper Realty Inc

35 Tower Ridge Rd, Oak Bluffs, MA 02557
/62
$1,895,000
- 4 Beds
- 2 Baths
- 2,462 Sq Ft
129 Beach Rd, Tisbury, MA 02568

Unique, waterfront property with amazing, 180 degree views of the lagoon from one side of the property, and the Vineyard Haven Harbor on the north side of the property. Zoned both residential and commercial, rarely does such a unique property become available. Elevated above Beach Road and the lagoon, there are 2 structures on the property. The first, sited on the lagoon with private access, is

Michele Moore Island Real Estate

129 Beach Rd, Tisbury, MA 02568
/45
$1,899,000
- 4 Beds
- 2.5 Baths
- 2,127 Sq Ft
5 Bayes Hill Cir, Vineyard Haven, MA 02568

Beautiful Bayes Hill Association! Located on a quiet cul-de-sac you will find this charming 4 bedroom colonial-style home. Very well maintained with a new Red Cedar Shingle Roof, a newer 75 Gallon Hot Water Heater, a High Efficiency Furnace and a Freshly Painted exterior. Year round home or wonderful investment property, look no further, THIS IS IT! An idyllic covered porch that overlooks a

Rene Jackson Island Real Estate

5 Bayes Hill Cir, Vineyard Haven, MA 02568
/26
$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
/19
$2,295,000
- 4 Beds
- 5 Baths
- 2,820 Sq Ft
71 Netock Ave, Oak Bluffs, MA 02557

On the doorstep of vibrant Oak Bluffs, discover this exquisitely renovated four bedroom home with separate office or studio space, all ensconced in professionally landscaped grounds. Blending modern comfort with timeless island charm, the house features wide plank white oak floors, beautiful ceiling height and natural light, an open-concept living-dining space with a new kitchen, a first-floor

Ellen Valentgas Sotheby's International Realty

71 Netock Ave, Oak Bluffs, MA 02557
/30
$2,195,000
- 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
/37
$2,150,000
- 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

Mike Sawyer Sawyer Realty Group

33 Lagoon Pond Rd, Vineyard Haven, MA 02568
/37
$2,240,000
- 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
/39
$2,240,000
- 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
/26
$2,100,000
- 3 Beds
- 3.5 Baths
- 2,124 Sq Ft
23 13th St N, Edgartown, MA 02539

This recently constructed home conveniently sits in the center of Edgartown close to Sengekontacket Pond. With 3 bedrooms, 3.5 baths, bright and sunny living areas, and a very spacious and finished lower level, this property is well-designed. Featuring hardwood floors throughout, the open concept on the first floor has modern kitchen with a center island and stainless appliances, a dining area

Cheri Mason Landvest MV

23 13th St N, Edgartown, MA 02539
/64
$2,100,000
- 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
/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
/24
$2,195,000
- 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 Bradley Wallace & Co. Sotheby's International Realty

30 Sengekontacket Rd, Oak Bluffs, MA 02557
/30
$2,195,000
- 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
/51
$2,300,000
- 4 Beds
- 3.5 Baths
- 3,274 Sq Ft
70 Spring St, Vineyard Haven, MA 02568

Storybook setting in the quaint seaside village of Vineyard Haven, the commanding Captain Gilbert L. Smith House, c. 1854, affords an enchanting opportunity for space and privacy within the highly sought after William Street Historic District and just two blocks to all the shops, restaurants, galleries, town beach, tennis, and ferry. The property also has potential for an additional buildable

June Flake Viewpoints

70 Spring St, Vineyard Haven, 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
/24
$2,095,000
- 4 Beds
- 3.5 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
/35
$1,470,000
- 3 Beds
- 2.5 Baths
- 1,620 Sq Ft
26 Winne Ave, Vineyard Haven, MA 02568

Welcome to your dream home just a short walk to the lagoon. This home offers easy access for dropping a kayak or taking a refreshing afternoon dip from a public access point. Discover this charming home nestled on a corner lot within a serene neighborhood. This beach home has an updated kitchen and bathrooms. The kitchen is equipped with new appliances and gorgeous quartz countertops, making it a

Joe & Nicole Holland Vineyard Dream Realty LLC

26 Winne Ave, Vineyard Haven, MA 02568
/19
$795,000
- 4 Beds
- 1 Bath
- 1,154 Sq Ft
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
/41
$14,500,000
- 6 Beds
- 5 Baths
- 4,964 Sq Ft
825 Main St, Vineyard Haven, MA 02568

Set on 1.75 acres this waterfront home features 200+/- feet of sandy beach on the outer harbor in the community of West Chop. Upon entering the home, the stunning view of the outer harbor and Nantucket Sound is breathtakingly beautiful. Perfect for hosting large parties or intimate family gatherings the spacious living room spills onto the large deck through two sets of French doors. Gleaming

Judy Federowicz Landmarks at TODAY Real Estate

825 Main St, Vineyard Haven, MA 02568
/44
$4,695,000 Open Thu 10AM - 12PM
- 3 Beds
- 2 Baths
- 1,716 Sq Ft
16 Frog Hollow, Vineyard Haven, MA 02568

Timeless Water View Home on Vineyard Haven Harbor. Nestled between historic Main Street and the exclusivity of West Chop, this property combines private coastal living with access to the best of Vineyard Haven. With access to the calm waters of the Harbor, the residence sits at the edge of a sweeping meadow with uninterrupted water views. Built in 2015 the three-bedroom, two-bathroom home is a

Rose Ryley Sandpiper Realty Inc

16 Frog Hollow, Vineyard Haven, MA 02568
/7
$765,000
- 3 Beds
- 1 Bath
- 1,168 Sq Ft
10 Putnam Way, Vineyard Haven, MA 02568

Raised ranch style house on a corner lot near the lagoon. This could be the "fixer upper" buyers always ask about. Location is in the Lagoon Pond watershed and BUYER will have to replace the septic system to bring up to latest environmental requirements.

Kathleen Dawson Donnelly + Co.

10 Putnam Way, Vineyard Haven, MA 02568
/33
$839,000
- 2 Beds
- 1 Bath
- 954 Sq Ft
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
/30
$1,800,000
- 3 Beds
- 2.5 Baths
- 1,822 Sq Ft
1 Saddle Club Rd, Edgartown, MA 02539

Welcome to your perfect island retreat in the heart of Edgartown conveniently located in a quiet neighborhood off of Edgartown West Tisbury Road. This charming 3-bedroom, 2.5 bathroom home offers the ideal blend of comfort, and functionality. Nestled on a quiet street, the property features an oversized two-car garage--perfect for storing vehicles, bikes, and beach gear, or even setting up a

Madelyn Silvia Wallace & Co. Sotheby's International Realty

1 Saddle Club Rd, Edgartown, MA 02539
/47
$5,450,000
- 4 Beds
- 5.5 Baths
- 3,300 Sq Ft
8 Paddock Rd, Oak Bluffs, MA 02557

Refined Vineyard Living in The Preserve - Set gracefully on a knoll with sweeping views of a tranquil pond and surrounding grasslands, this beautiful residence offers a masterful blend of traditional coastal architecture and modern luxury. Located in the prestigious enclave of The Preserve, this sprawling home is designed for effortless elegance, privacy, and indoor-outdoor living.At the heart of

Lesley Heidt Sandpiper Realty Inc

8 Paddock Rd, Oak Bluffs, MA 02557
/15
$845,000
- 2 Beds
- 1 Bath
- 624 Sq Ft
60 -R Carol Ln, Oak Bluffs, MA 02557

Charming Ranch-Style Cottage nestled on an 8,438 sq ft lot, this cozy ranch-style cottage offers easy, single-story living, ideal for those seeking the simplicity and charm of island life. The bright and open-concept kitchen and living area features a breakfast bar, creating a warm and welcoming space for everyday living or entertaining. The home includes two comfortable bedrooms and one full

Sheila Morse Island Real Estate

60 -R Carol Ln, Oak Bluffs, MA 02557
/14
$845,000
- 2 Beds
- 1 Bath
- 624 Sq Ft
60R Carol Ln, Oak Bluffs, MA 02557

Charming Ranch-Style Cottage nestled on an 8,438 sq ft lot, this cozy ranch-style cottage offers easy, single-story living, ideal for those seeking the simplicity and charm of island life. The bright and open-concept kitchen and living area features a breakfast bar, creating a warm and welcoming space for everyday living or entertaining. The home includes two comfortable bedrooms and one full

Nora Jardin Island Real Estate

60R Carol Ln, Oak Bluffs, MA 02557
/28
$1,325,000
- 3 Beds
- 2 Baths
- 1,764 Sq Ft
170 Barnes Rd, Oak Bluffs, MA 02557

Calling water and boating enthusiasts. Solid Cape-style home one block from Sailing Camp Park, water access to the Lagoon and one mile to all the excitement that downtown Oak Bluffs has to offer. The first floor offers a spacious eat in kitchen that is open to the dining room. A full bathroom with laundry, a den with French-doors that leads to the living room with a slider opening out to the back

Christine Rose Martha's Vineyard Island-Wide Realty

170 Barnes Rd, Oak Bluffs, MA 02557
/23
$1,149,000
- 3 Beds
- 2 Baths
- 960 Sq Ft
67 12th St S, Edgartown, MA 02539

This ranch style 3 bedroom home centrally located in a quiet neighborhood is close to the bike path with easy access to town and beaches. Sited on a 12,000 square foot parcel with a spacious privately enclosed yard and mature gardens. First floor includes an efficient galley kitchen with a quaint dining area. The living room leads out to a cozy front porch. There is also a spacious side deck that

Brenda Galligan Karen M. Overtoom R.E.

67 12th St S, Edgartown, MA 02539

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Massachusetts Dukes County Vineyard Haven

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In Vineyard Haven, there are currently 133 houses for sale, offering an array of options for potential buyers. Whether you're searching for a single-family residence, exploring single-family detached houses for sale, or considering new construction houses for sale, there are options to cater to different lifestyles. Explore the listings and houses for sale in Vineyard Haven, MA and find the perfect place to call home.

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