4 Bedroom homes for sale & real estate in Vineyard Haven, MA

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ABOUT THIS HOME
4 Bedroom Homes for Sale in Vineyard Haven, MA
Impressive four-bedroom home with a distinctive floor plan that combines privacy, comfort, and convenience in one of Oak Bluffs' most desirable locations. The main living area, filled with natural light and soaring ceiling, offers an open layout that is warm and inviting. A third floor den and exterior decks on all levels provide ample living space both indoors and out. Set within the sought-after Meadow View Farms community, residents enjoy access to beautifully maintained common meadows, as well as association tennis and pickleball courts. The neighborhood's peaceful setting fosters a true sense of community, while its prime location, just off the bike path, places Farm Neck Golf Club and

$1,825,000

4 beds3 baths3,142 sq ft

7 South Meadow Ln, Oak Bluffs, MA 02557

Third floor den • Exterior decks • 0.66 acre lot

ABOUT THIS HOME
4 Bedroom Homes for Sale in Vineyard Haven, MA
Your private oasis with a POOL awaits in this beautifully updated Lagoon Hills retreat on over 1.5 acres. Enjoy a carefree, single-level lifestyle featuring an open-concept kitchen and dining area, spacious living room, office and exercise room — all thoughtfully designed for comfort and flow. Step outside to a stunning backyard anchored by a sparkling pool, surrounded by decks, patios, and lush landscaping with stone walls, specimen trees, and a goldfish pond with a waterfall. Additional amenities include a pool house, a detached one-car garage/workshop, an oversized two-car garage, and a full basement—perfect for extra storage or hobbies. With private access to Lagoon Pond, th

$2,499,000

4 beds2.5 baths2,544 sq ft

47 Tiffany Dr, Oak Bluffs, MA 02557

Pool house • Private oasis • Full basement

ABOUT THIS HOME
4 Bedroom Homes for Sale in Vineyard Haven, MA
This move-in ready four-bedroom, being offered fully furnished, delivers effortless living, simply bring your swimsuit and settle in. Featuring an open and inviting layout, the living space seamlessly extends to the large deck and heated pool, perfect for relaxing or entertaining. Conveniently located just one mile from the shops and restaurants of downtown Vineyard Haven and less than two miles from the sandy shores of Tashmoo public beach. With a strong rental history, it's perfectly suited as a year-round residence, vacation retreat, or investment property. The property is located within the Tashmoo Watershed District, and the septic system will require upgrades to comply with denitrific

$1,300,000

4 beds2 baths1,566 sq ft

344 Greenwood Ave, Vineyard Haven, MA 02568

Large deck • One mile from shops • Heated pool

ABOUT THIS HOME
4 Bedroom Homes for Sale in Vineyard Haven, MA
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 a peaceful and private deck. Living room offers a comfortable space for TV and relaxing. There is also nice size first floor primary with walk-in closet and spacious en-suite bathroom. The grand entryway takes you to the second floor which offers a second primary bedroom with walk-in closet and en-

$2,295,000

4 beds3.5 baths2,690 sq ft

151 Tashmoo Ave, Tisbury, MA 02468

Wrap around porch • Open floor plan • Stainless appliances

ABOUT THIS HOME
4 Bedroom Homes for Sale in Vineyard Haven, MA
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 the home lies an expansive great room with soaring cathedral ceilings, rich paneling, and detailed millwork. Flooded with natural light from an array of dormers and oversized windows, the space is warm and welcoming. Three sets of French doors open to a bluestone terrace, complete with multiple se

$5,450,000

4 beds5.5 baths3,300 sq ft

8 Paddock Rd, Oak Bluffs, MA 02557

Bluestone terrace • Sweeping views • Tranquil pond

Property at 6 Brewster Ave, Oak Bluffs, MA 02557, 4 beds, 3 baths

$3,250,000

4 beds3 baths1,728 sq ft

6 Brewster Ave, Oak Bluffs, MA 02557

Property at 113 Leonard Cir, Vineyard Haven, MA 02568, 4 beds, 2 baths

$1,099,000

4 beds2 baths1,306 sq ft

113 Leonard Cir, Vineyard Haven, MA 02568

Property at 40 Scotchmans Ln, West Tisbury, MA 02575, 4 beds, 2 baths

$1,495,000

4 beds2 baths1,332 sq ft

40 Scotchmans Ln, West Tisbury, MA 02575

Property at 157 Ben Chase Rd, West Tisbury, MA 02575, 4 beds, 2.5 baths

$2,250,000

4 beds2.5 baths2,982 sq ft

157 Ben Chase Rd, West Tisbury, MA 02575

Property at 5 Pinetree Ln, Vineyard Haven, MA 02568, 4 beds, 3 baths

$1,999,999

4 beds3 baths2,730 sq ft

5 Pinetree Ln, Vineyard Haven, MA 02568

Property at 12 & 14 Maple Ave, Oak Bluffs, MA 02557, 4 beds, 4 baths

$1,830,000

4 beds4 baths1,600 sq ft

12 & 14 Maple Ave, Oak Bluffs, MA 02557

Property at 21 Woodlawn Ave, Vineyard Haven, MA 02568, 4 beds, 3 baths

$2,495,000

4 beds3 baths2,562 sq ft

21 Woodlawn Ave, Vineyard Haven, MA 02568

Property at 7 Upper Meadow Ln, Oak Bluffs, MA 02557, 4 beds, 2.5 baths

$1,850,000

4 beds2.5 baths3,268 sq ft

7 Upper Meadow Ln, Oak Bluffs, MA 02557

Property at 4 High Meadow Ln, Oak Bluffs, MA 02557, 4 beds, 3.5 baths

$2,260,000

4 beds3.5 baths2,810 sq ft

4 High Meadow Ln, Oak Bluffs, MA 02557

Property at 63 Bayes Hill Rd Rd, Oak Bluffs, MA 02557, 4 beds, 4 baths

$3,150,000

4 beds4 baths5,165 sq ft

63 Bayes Hill Rd Rd, Oak Bluffs, MA 02557

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ABOUT THIS HOME
4 Bedroom Homes for Sale in Vineyard Haven, MA
Edgartown Village Opportunity – Main House & New Guest Cottage Tucked just off Upper Main Street, this unique Edgartown property offers exceptional flexibility with two dwellings—perfect for personal use, rental income, or a combination of both. The main house has been thoughtfully updated with numerous improvements, including a new kitchen, renovated bath, upgraded electrical, and HVAC system for year-round comfort. The guest house, newly built in 2025, provides a fresh, turnkey space ideal for guests or rental potential. With a total of four bedrooms between both structures—and the ability to expand to six bedrooms thanks to town water and sewer connection—th

$1,600,000

4 beds3 baths1,738 sq ft

10 Dory Cir, Edgartown, MA 02539

New kitchen • Turnkey space • Upgraded electrical

ABOUT THIS HOME
4 Bedroom Homes for Sale in Vineyard Haven, MA
Private, yet close to town. Located at the end of a paved road on a cul-de-sac that abuts 25 acres of conservation land. Enjoy miles of walking/bike trails and ancient roads just out the door. The first floor has an open floor plan with comfortable living / dining area / kitchen areas. There is also a first-floor bedroom/office, new sun room and 1/2 bathroom. Upstairs, there is a large primary bedroom en suite with relaxing soaking tub. The two additional spacious bedrooms share a bathroom with a walk-in shower. The basement has been remodeled to include a recreation, art and laundry rooms. There is also an owner's closet. The house is hooked up to town water and sewer so there are expansio

$2,150,000

4 beds2.5 baths2,547 sq ft

8 Old Purchase Way, Edgartown, MA 02539

Open floor plan • Walking bike trails • New sun room

ABOUT THIS HOME
4 Bedroom Homes for Sale in Vineyard Haven, MA
KATAMA BEACH HOUSE - This turnkey Katama retreat blends coastal charm with modern comfort, offering a rare combination of location, amenities, and style. A 19-foot heated swim spa with current, and beautiful wooden deck, lets you swim year-round or unwind in the attached Jacuzzi. The property comes fully furnished, making it an effortless purchase, and boasts a strong rental history for investment potential. Recent upgrades include a new roof in 2024, a beautifully renovated tile bath in 2025, new maple floors upstairs, refreshed interiors, and updated landscaping. Inside, the sun-filled kitchen and dining area with cathedral ceilings create an inviting space for gatherings. Stainless appli

$1,750,000

4 beds2 baths1,342 sq ft

58 Road to The Plns, Edgartown, MA 02539

0.5 acre lot • Pool • Built 1981

ABOUT THIS HOME
4 Bedroom Homes for Sale in Vineyard Haven, MA
Nestled in the heart of Chilmark, this four-bedroom home offers a blend of comfort, convenience, and timeless Vineyard charm. Thoughtfully designed with distinct, well-proportioned rooms, the home centers around an expansive, sunlit, eat-in kitchen featuring dual ovens, elegant granite countertops, and extensive custom cherry wood built-ins that combine beauty and practicality. The welcoming living room, anchored by a pristine Vermont Castings wood stove, opens seamlessly to a covered porch and spacious deck--perfect for morning coffee or evening gatherings. The spacious first-floor primary suite provides a private retreat with two en-suite baths and two walk-in closets. Upstairs, you'll fi

$1,895,000

4 beds3.5 baths2,061 sq ft

174 Middle Road Rd, Chilmark, MA 02535

Covered porch • Spacious deck • Eat-in kitchen

ABOUT THIS HOME
4 Bedroom Homes for Sale in Vineyard Haven, MA
Nestled on a generous corner lot in one of Edgartown’s sought-after neighborhoods, this beautifully maintained 4BD, 3.5BA home offers the perfect blend of comfort, convenience, and classic Vineyard charm. The home features a spacious and versatile floor plan, ideal for both year-round living and summer getaways. The light-filled living areas, anchored by a floor to ceiling wood burning fireplace, flow seamlessly into a well-appointed kitchen and dining area, perfect for entertaining. Step into the inviting screen porch-an ideal spot to enjoy your morning coffee or unwind with evening breezes. A partially finished basement and two-car garage provides ample storage, while the associatio

$2,750,000

4 beds3.5 baths2,566 sq ft

28 Martha's Rd, Edgartown, MA 02539

Expansive yard • Corner lot • Screen porch

NEW CONSTRUCTION

ABOUT THIS HOME
4 Bedroom Homes for Sale in Vineyard Haven, MA
Contemporary Farmhouse, NEW CONSTRUCTION in EDGARTOWN, a short distance from the VILLAGE, with a heated POOL. This home features an open floor plan with casual coastal living in mind. The outdoor pool/entertaining area flows with ease into the home's interior space. A thoughtful mudroom offers quick bathroom and pantry access to and from the pool area. The sliding glass doors in the great room and dining area open to the outdoor living space; a smart design. The kitchen/dining and great room combine together as one large gathering area with the fireplace acting as a focal point to gather around. Four bedroom en-suites offer privacy for its guests. A 1st floor bedroom en-suite is offered alo

$4,800,000

4 beds5 baths4,280 sq ft

7 Clark Dr, Edgartown, MA 02539

Open floor plan • Mudroom • Private bathroom

Property at 135 The Boulevard &110 Pilgrim Rd, Edgartown, MA 02539, 4 beds, 3.5 baths

$5,999,000

4 beds3.5 baths2,995 sq ft

135 The Boulevard &110 Pilgrim Rd, Edgartown, MA 02539

Property at 99 Old Purchase Rd, Edgartown, MA 02539, 4 beds, 2.5 baths

$1,895,000

4 beds2.5 baths2,064 sq ft

99 Old Purchase Rd, Edgartown, MA 02539

Property at 25 Fulling Mill Rd, Chilmark, MA 02535, 4 beds, 3 baths

$2,395,000

4 beds3 baths1,918 sq ft

25 Fulling Mill Rd, Chilmark, MA 02535

Property at 4 Boldwater Rd, Edgartown, MA 02539, 4 beds, 3.5 baths

$4,150,000

4 beds3.5 baths3,552 sq ft

4 Boldwater Rd, Edgartown, MA 02539

4 Bedroom Homes for Sale in Vineyard Haven

There are currently 15 4 bedroom homes in Vineyard Haven. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Vineyard Haven stay on the market for 122 days. Popular neighborhoods include Martha's Vineyard. This map is refreshed with the newest listings in Vineyard Haven every 15 minutes.

In the past month, 1 home has been sold in Vineyard Haven. In addition to houses in Vineyard Haven, there were also 3 condos, 0 townhouses, and 1 multi-family unit for sale in Vineyard Haven last month. Find your dream home in Vineyard Haven using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Vineyard Haven are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Vineyard Haven. Our Vineyard Haven real estate stats and trends will give you more information about home buying and selling trends in Vineyard Haven. If you're looking to sell your home in the Vineyard Haven area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Vineyard Haven with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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