luxury houses for sale Vineyard Haven, United States

Nestled at 5 Pinetree Lane, Vineyard Haven, MA, this single-family residence in Dukes County presents a unique opportunity to own a piece of classic American architecture. Built in 1927, this home offers a blend of vintage charm and comfortable living. The residence features three full bathrooms, providing convenience and privacy for all occupants. Imagine mornings where everyone can prepare for the day without the rush, and evenings where relaxation is never compromised. The thoughtful design ensures that personal space is always readily available. With four bedrooms, this home provides ample space for rest and rejuvenation. Envision each room becoming a personalized sanctuary, tailored to individual preferences and needs. Whether it's a tranquil space for sleep, a vibrant area for hobbies, or a practical room for remote work, these bedrooms offer the flexibility to adapt to any lifestyle. The 2730 square feet of living area unfolds to provide a comfortable and inviting environment.

Set on a generous 0.3-acre lot in desirable Oak Bluffs, this property offers exceptional potential just moments from Vineyard Sound. A newly installed 6-bedroom septic system opens the door to a variety of expansion opportunities. The home is thoughtfully designed with two separate living areas, ideal for guests or rental possibilities. The main living space features hardwood floors throughout, a spacious living room with a fireplace, kitchen, sunroom, and a primary bedroom with a full bath. An additional shared living room serves as the central gathering space between the two wings of the home, creating a seamless and functional layout. The secondary living area includes a kitchenette, dining space, guest bedroom, and bathroom. The bathroom is currently unfinished, providing the next owner the opportunity to customize it to their taste. Upstairs, the second level boasts high ceilings, abundant natural light, a guest bedroom, and a private office space. Additional highlights include a two-car garage, a large rear deck, and a private backyard setting. An excellent investment or renovation opportunity in Oak Bluffs, offered as-is.

Recently updated Oak Bluffs ranch-style home ideally located near Downtown and Oak Bluffs Harbor. Step inside to discover vaulted ceilings and an airy open floor plan that seamlessly connects the living room, dining area, and a spacious kitchen featuring granite countertops and updated appliances. The private primary suite is thoughtfully positioned off the main living area and offers a full bath with in-suite laundry, plus its own separate exterior entrance, perfect for added privacy or guest flexibility. Two additional guest bedrooms and a full hall bath complete the interior layout. Outdoor living is equally inviting, with a charming front deck featuring built-in bench seating, a stone patio for entertaining, and a convenient storage shed. Recent upgrades include a new roof, updated flooring, and energy-efficient mini-split systems for heating and cooling. Move-in ready and perfectly suited for enjoying the Vineyard lifestyle.

Enjoy timeless summers at this Hidden Cove condo, where days begin with a paddle on Sengekontacket Pond, afternoons are spent between the pool and tennis courts, and evenings end on the deck after a day spent exploring the island. This three-bedroom unit has distant water views and offers an easy, multi-level floor plan with open living spaces, a private primary suite, two guest bedrooms, a detached garage, and exclusive access to Hidden Cove's sought-after amenities, including a private boat launch. Just minutes from Oak Bluffs, Farm Neck Golf Club, beaches, and the bike path, this is a place where generations return to create the kind of Martha's Vineyard summers that never go out of style.

Move-in ready 3-bedroom, 1.5-bathroom house with a warm and welcoming interior. The main level includes an efficient kitchen, living room, dining room with sliders to the mahogany deck and outdoor shower, 1 bedroom, laundry, and convenient half-bath. A one car garage is attached to the main level. The 2 large bedrooms and a full bath are located upstairs. Enjoy the private backyard with its well established perennial gardens, complete with a she shed which is perfect for relaxing or entertaining. Great location on a paved road with easy access to kayaking, the bike path, Felix Neck, and Town.Title V has passed. Owner occupied- 24 hrs notice to show please.

Nestled within the prestigious Nats Farm Association this beautifully crafted West Tisbury home offers a quintessential Martha’s Vineyard retreat. Designed for comfortable island living, the first floor features a bright, open floor plan with a well-appointed kitchen, dining area, and inviting living room, perfect for gathering with family and friends. The generously sized primary suite is thoughtfully positioned on the main level and includes a private office and a spa-like bath with soaking tub and separate shower. French doors open to a lovely stone patio surrounded by established perennial gardens, an ideal setting for morning coffee or summer evenings under the stars. Upstairs are two welcoming guest bedrooms, while a detached bedroom suite provides exceptional flexibility and privacy for visitors. Tucked quietly in the backyard, a charming cottage creates yet another cozy retreat space for guests, creative pursuits, or peaceful relaxation. Surrounded by mature trees and lush landscaping, the meticulously maintained grounds offer an inviting backdrop for outdoor entertaining and quiet enjoyment alike. As a West Tisbury resident, you’ll also enjoy access to the highly coveted Lamberts Cove Beach. Whether you’re seeking a year-round home or the perfect Vineyard getaway, this special property captures the very best of island living.

House & Guesthouse near Long Point Beach! The Island's coveted south shore is just minutes from this charming West Tisbury compound, where the connection to nature is seamless. The main house sits high atop the trees and overlooks a park-like, fenced-in backyard, perfect for kids and dogs. The yard also encompasses a sweet vegetable garden, a storage shed, and outdoor shower. Inside, find an open floor plan with natural light streaming in from windows and skylights. The kitchen flows to the dining area, which flows to the spacious living room anchored by a wood-burning stove for cozy ambience. Also on this level is the primary bedroom with two closets, and a large full bathroom with a soaking tub and separate tiled shower. The larger, open loft upstairs offers versatile living space perfect for reading, television, or spillover guests. Downstairs on ground level is another full bathroom and two bedrooms plus a light-filled home office with a convenient exterior access. Other features for the main house are a new furnace and 4 mini splits for air conditioning. Last but not least, adding tremendous value to the property, is a beautiful, spacious guesthouse with every detail curated for comfort and style; central air and heat, a living room with a gas fireplace, a full eat-in kitchen, a bedroom with two closets, a full bathroom, a bonus attic room, and a deck perfect for bird watching while listening to the distant rhythm of the Atlantic! This property is not to be missed! Note: At closing Seller will credit Buyer for 4-bedroom septic system upgrade. See design by VLSE in documents.

Nestled within Seven Gates Farm, one of Martha's Vineyard's most storied and scenic communities, this 26.5-acre estate offers a beautifully renovated farmhouse that seamlessly blends modern comforts with historic charm. Surrounded by ancient stone walls, mature trees, and lush gardens, the property includes a charming guest house, scenic walking paths, and a peaceful hilltop retreat with a stone bench, offering stunning water views of Vineyard Sound and the Elizabeth Islands. Ideally located just steps from Gray's Beach and dock, this is one of the most picturesque properties in Seven Gates Farm. The Seven Gates Farm community consists of 45 homesites on 1,600 acres with 1,000 acres of protected conservation land, open fields, woodlands, ponds, and miles of trails for walking and horseback riding. Residents of Seven Gates Farm also enjoy exclusive access to 1.5 miles of private beach, two piers, and two tennis courts. This rare opportunity allows you to become part of a remarkable community, once an assembly of farms, that remains dedicated to the preservation and stewardship of the land.

Directly across from the iconic Heights Beach, sits this beautifully appointed Cape style residence offering the quintessential Falmouth coastal lifestyle. Perfectly positioned to capture sparkling water views and cooling ocean breezes, the home enjoys a front-row seat to one of Cape Cod's most beloved beaches, known for its expansive sandy shoreline, Vineyard Sound vistas, and vibrant summer atmosphere. Inside, sun-filled living spaces are designed for comfort and gathering, while classic architectural details create a timeless coastal retreat. Expansive windows frame water views, and the inviting ocean view porch is the perfect place to enjoy morning coffee, afternoon sea breezes, or spectacular evening sunsets. Just moments from Falmouth Village, the Island Queen ferry to Martha's Vineyard, restaurants, shops, and the finish line of the renowned Falmouth Road Race, this exceptional property places the very best of Cape Cod at your doorstep. Enjoy the celebrated 4th of July fireworks from the comfort of your front porch. Whether as a year-round residence, summer getaway, or investment opportunity, this is a rare chance to own a home in one of Falmouth's most coveted locations.

A rare opportunity to create a premier in-town compound in one of Edgartown’s most desirable locations. Set on High Street, just moments from downtown Edgartown, this exceptional 16,000+ square foot lot offers tremendous potential to create a substantial five-bedroom residence while enjoying the convenience and charm of village living. The property currently features a 4 bedroom main house, attached 1 bedroom apartment, and an oversized garage with an attached 556-square-foot barn. The property provides a unique foundation for expansion, renovation, or a thoughtfully designed new build. With its generous lot size and coveted location, 49 High Street presents a rare opportunity to create a legacy property within walking distance of Edgartown’s shops, restaurants, harbor, and village amenities.

Spectacular water views from nearly every room! Breathtaking sunrises and sunsets overlooking Vineyard Sound, Bristol and Falmouth Heights Beaches, and Little Pond. This home offers one of the finest vantage points in town for enjoying the Fourth of July fireworks. Offered for the first time in over 100 years, this exceptional property combines timeless character with comfortable living. Rebuilt in 1992, two properties were combined and the structure was raised 14 ft., providing for a garage and basement. The convenience of one floor living is provided with an elevator, first-floor bedroom suite, and first floor laundry. Multiple living spaces are provided for entertaining family and friends. The sun-filled sunroom is the perfect place to start your morning. Additional features include a two-car garage, wrap-around deck, and a private yard ideal for summer enjoyment. Mechanicals on first and second floors. New 2000-gallon septic tank installed in 2026. Passing Title V in hand.

A rare legacy offering in the heart of Edgartown Village, this extraordinary in-town compound is among the largest of its kind on Martha’s Vineyard. Originally built in 1835 and masterfully renovated by renowned architect Patrick Ahearn, the estate seamlessly blends historic character with refined modern luxury. Just moments from Edgartown Harbor and the island’s premier dining and shopping, the property spans two lots and offers an extraordinary compound featuring 10 bedrooms and 14 baths. Designed for both elegant entertaining and comfortable everyday living, the main residence showcases refined architectural details and modern technology. Beautiful oak floors run throughout the home, complemented by sophisticated hardware, premium appliances, and walls tastefully finished with nickel board. A gracious living room with fireplace opens to a patio with retractable screens, creating effortless indoor-outdoor flow. The chef’s kitchen is impeccably appointed with dual dishwashers, a plumbed miele coffee bar, refrigerator drawers, and a wine refrigerator. A custom brass and glass bar is equipped with an ice maker and refrigerated drawers and can easily be converted into a secondary kitchen. Two private bedrooms with en-suite tile baths anchor opposite wings of the main level, providing both privacy and balance. The main floor also includes an inviting secondary living room with a gas fireplace, an elegant dining room wrapped in seagrass wallpaper, a generous walk-in pantry, and a spacious mudroom thoughtfully designed for effortless island living. Upstairs a spectacular primary suite serves as a retreat, complete with private balcony and a bonus two full spa-inspired baths. Three additional en-suite guest rooms and a spacious laundry room complete the second floor. The third level features a charming nautical-themed bunk room with four built-in beds and full bath. The finished lower level includes two bedrooms with en-suite baths, a media room, wine cellar, and additional laundry. Beyond the main house is a beautifully finished two-car garage with brick floors and wood-paneled walls. The carriage house above the garage offers a private guest suite with a balcony overlooking the pool. The outdoor setting is unparalleled for in-town living. Lush hydrangeas surround a resort-style pool and spa, complemented by a built-in grill, firepit, and an exceptional cabana with kitchenette, half bath, laundry, heating and air conditioning. This Edgartown estate offers privacy, scale, and sophistication rarely found within steps of Main Street. An iconic Martha’s Vineyard property reimagined for modern coastal living.

Located in the highly sought-after Nora’s Meadow community in Edgartown, this exceptional coastal property offers the rare combination of privacy, acreage, and close proximity to downtown Edgartown, South Beach, and the Katama bike path. Set on 1.8 beautifully landscaped acres, this custom home was built in 2014 and features over 4,000 square feet of thoughtfully designed living space across three levels. A welcoming mudroom, ideal for beach living, opens into a bright and expansive main living area featuring a spacious dining room, gourmet kitchen, and comfortable living room with oversized French doors leading to the pool patio. The first floor primary suite offers a luxurious spa-inspired bath and private French doors opening to a serene outdoor sitting area surrounded by lush landscaping. Four additional guest bedrooms are all generously sized, providing ample accommodations for family and friends. The finished lower level includes a media room, pool table area, and abundant storage space. Designed for effortless indoor-outdoor living, the backyard is a true Vineyard retreat featuring an oversized pool, outdoor kitchen, expansive stone patio, and a pool cabana complete with a full bath. A two-car garage includes unfinished space above with the unique potential to create a guest house, an exclusive feature permitted only for this property within the Nora’s Meadow association. A charming barn-style shed provides additional storage for kayaks, bikes, and boating equipment. This rare offering combines luxury, privacy, and exceptional outdoor living in one of Edgartown’s most desirable neighborhoods, creating the ultimate Martha’s Vineyard retreat for generations to enjoy.