luxury seaside house for sale Oak Bluffs, United States

Rare Downtown Vineyard Haven Compound Offering! An exceptional opportunity to own two separate properties being offered together in the heart of Vineyard Haven. Just moments from the ferry terminal, restaurants, shops, and the harbor, this unique package offers the ideal blend of luxury living, investment potential, and an amenity that is nearly impossible to find in town with expansive parking. 33 Lagoon Pond Road is a newly constructed, thoughtfully designed three bedroom, three bathroom home where luxury meets sophisticated coastal charm. Featuring an open floor plan, a designer kitchen with quartz countertops, custom tile bathrooms, and seamless indoor-outdoor living, the home enjoys water views from the living room, bedrooms, and inviting front porch. A private backyard, spacious rear deck, and attached two car garage provide both privacy and convenience, while the property's impressive rental history adds outstanding investment appeal. Complementing the main residence is 29 Lagoon Pond Road, a beautifully renovated two bedroom, one bath cottage offering its own private retreat with a charming rear patio and outdoor shower. Ideal for extended family, guests, employee housing, or additional rental income, the cottage provides flexibility for a variety of ownership opportunities. A true standout feature of this offering is the oversized rear parking lot at 29 Lagoon Pond Road, accommodating approximately ten vehicles. Parking of this scale is exceptionally rare in downtown Vineyard Haven and significantly enhances the property's versatility. Whether you're seeking a family compound, an income producing investment, or a premier in town property with unmatched flexibility, 29 & 33 Lagoon Pond Road represent a truly one of a kind opportunity in downtown Vineyard Haven.

Step into a piece of Martha's Vineyard history with this exceptionally charming antique Cape, originally dating back to 1808. While the home proudly retains its authentic historical character, boasting exquisite period details, rich moldings, and wide-pine floorboards, it has been thoughtfully updated to offer the ultimate in contemporary living. There are 5 total bedrooms: 2 on the first floor and 3 on the second floor. Two bedrooms are en suite: 1 on the 1st floor and 1 on the 2nd floor. There are 4 full bathrooms (3 renovated), and a light-filled, spacious kitchen, designed to blend old world charm with modern needs. Additional updates include central AC, 3 lined chimneys, and an upgraded septic system. A bluestone patio is ideal for al fresco dining, and a lovely, professionally maintained backyard and garden complete the storybook picture. Perfectly positioned across from picturesque Owen Park, this property places you at the very heart of Vineyard Haven culture and coastal convenience. Take in water views and boat activity on scenic Vineyard Haven Harbor. Enjoy the newly built town dock and the historic bandstand where you can enjoy the Vineyard Haven Band play on Sunday evenings in the summer. Schedule your tour today and experience the magic of Vineyard Haven living.

Expanded cottage with in-law suite, garage, and detached studio. On the way to West Chop, it is equidistant to Downtown Vineyard Haven, the flagpole at West Chop, Mink Meadows Golf Club, and Vineyard Haven Yacht Club. This 4 bedroom, 4 bathroom property offers a flexible floor plan, including a private inlaw wing complete with its own entrance, kitchen, living room, full bathroom, and bedroom—perfect for extended family or guests. There are two driveways. The home also features a garage and a finished basement offering excellent storage or future expansion potential. A detached studio at the rear of the property provides wonderful overflow space for a home office, art studio, or guests. The property is only 2/10ths of a mile to the town beach at the end of Grove Ave, and half a mile to the town beach on Owen Little Way. Ready for a new owner's vision and updates, this well-located property presents an exceptional opportunity to enjoy the convenience and charm of this desirable neighborhood. This property is being offered "as-is."

House & Apartment Near Lagoon! Discover a rare opportunity in a convenient Vineyard Haven neighborhood. This clean, bright, move-in-ready property features a 3 BR, 1 BA main house plus a legal 1 BR, 1 BA accessory apartment, offering the perfect setup for multi-generational living or a high-demand rental to offset the mortgage. The main house, featuring a wonderful sunroom, an efficient kitchen, and a comfortable living room anchored by a beautiful stone fireplace, has been emptied and awaits the new owner's touch (please refer to images showing digital staging). Both the main house and the apartment have been freshly painted throughout. Situated on a spacious corner lot, and located a short distance to down town and public Lagoon access, this property is a super value. Seller will credit the buyer the cost of a brand new septic system at closing.

Tashmoo Farm, one of Martha’s Vineyard’s iconic properties, a take-your-breath-away landmark on Lamberts Cove Road! This country estate of over 10 acres is within close proximity of the village of Vineyard Haven with its boutiques and bourgeoning restaurant scene, and yet feels secluded and remote. For 3 centuries it has been a beloved year-round residence and at times a sought-after vacation home for a client list that included Lady Diana Spencer. The historic main house has been completely modernized. There are 6 bedrooms spread out over almost 6000 square feet, a detached pool house, swimming pool, and Har-Tru tennis court. Wherever you are in this gracious home you will be blessed with sweeping views of the open fields, stone walls, and horses in the neighboring farm, a scene as if from a painting done in a previous century. Included within the 10 acres is a separate 3.3-acre parcel of land that will accommodate a full-size home. The property is part of the Tashmoo Farm Association which includes deeded access to the association dock on Lake Tashmoo and tennis courts.

Charming four bedroom property set on 0.88 acres along Codman Spring Road, offering a convenient location with easy access to Edgartown Village, Morning Glory, South Beach and all other island towns. Surrounded by beautiful gardens, the home features an expansive wraparound deck ideal for outdoor living and entertaining, as well as a garden shed for additional storage. Inside, two wood-burning fireplaces and a wood stove add warmth and character, while abundant natural light and a highly functional floor plan create a welcoming and comfortable home well suited to a variety of lifestyles. Connected to town sewer, the property offers the potential for up to seven bedrooms with town approval, providing exciting possibilities for future expansion. A partially finished walk-out basement adds flexible additional space. Whether enjoyed as a year round residence or seasonal Island retreat, this property offers space, convenience, and potential. To add to this well rounded offering, this property is also being offered turnkey!

Introducing a landmark property in Edgartown’s Starbuck Neck enclave, just one tenth of a mile to Fuller Street Beach. Included in this sale is an adjoining vacant buildable lot. 14 STARBUCK NECK features a 7-bedroom house with 5 full bathrooms, garage, and plunge pool. Known as the Tower House, this home offers delightful views of the harbor from the first and second floors. The views from the bedroom and office located in the tower are stunning. 23 THAYER STREET is an extremely rare vacant lot in the heart of the Starbuck Neck neighborhood. With well over a third of an acre of land, the lot will comfortably accommodate a 5-bedroom house with guesthouse and pool.

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.

Set on over a half an acre in Edgartown’s desirable Island Grove neighborhood, this three-bedroom, two-bath classic Cape offers an exceptional expansion opportunity in a convenient Katama location. The existing 1,560-square-foot home can be enjoyed as-is while plans are developed for a renovation, expansion, or new construction. With a connection to town sewer, the property can support up to seven bedrooms, creating potential for a substantial residence, pool, and accessory dwelling unit. Surrounded on two sides by common land, this lot offers a unique level of privacy. Association tennis courts are located nearby, with Morning Glory Farm, Edgartown Village, South Beach, shops, restaurants, and the harbor all within easy reach. A rare opportunity to create a custom Vineyard retreat in an established neighborhood.

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.

A compelling opportunity to own in one of Falmouth's most desirable coastal locations. Welcome to 205 Grand Avenue, where the best of Cape Cod living is right outside your door. Ideally positioned in sought-after Falmouth Heights, this distinctive property offers the location buyers dream about—close to the beach, harbor, restaurants, and all the energy of Falmouth's vibrant seaside community. Enjoy morning walks along the shore, afternoons at the beach, and summer evenings taking in everything this iconic neighborhood has to offer. Whether envisioned as a year-round residence, Cape Cod retreat, or investment opportunity, 205 Grand Avenue offers exceptional versatility in a location that is increasingly difficult to replicate. Now offered at $2,400,000, this significant price adjustment creates a fresh opportunity for buyers who have been waiting for the right Falmouth Heights property. Come take another look—the value and possibilities may surprise you.

Tucked along the water's edge in one of Mashpee's most scenic settings, this rare coastal retreat offers the quintessential Cape Cod boating lifestyle with a private sandy beach area, deepwater dock and sweeping water views. Comprised of two waterfront parcels at 22 & 23 Samoset Road, the property blends the charm of a classic Cape retreat with exceptional potential to renovate, reimagine or enjoy as-is. The light-filled interior features vaulted ceilings with exposed beams, wide pine floors and walls of glass framing the water beyond. An expansive waterfront deck creates seamless indoor-outdoor living, while the spacious living room with dramatic brick hearth and wood stove flows to the dining area, kitchen and water-facing gathering spaces. The adjoining waterfront parcel provides added privacy and exciting possibilities for expanded outdoor living or other future improvements, subject to applicable approvals. With conservation land beyond, sandy frontage, deepwater access and remarkable potential, this is a truly special opportunity to own a legacy Cape Cod waterfront property. Credit being provided for new septic & roof.

Expect the unexpected as you enter into this totally recreated property. The past has been replaced with a clean, sleek and contemporary feel both on the interior and exterior. The entranceway showcases the handsome modern stairway which complements the new design within. The lower level contains an open family room, recreation area and kitchenette, separate guest ensuite as well as office space, laundry and mudroom. Ascending the stairway to the main level, expanses of glass capture the great natural lighting. The open floor plan provides an extensive living area combining the kitchen, dining area and living room with a beautiful wood fireplace as a lovely centerpiece, and a new half bath has been added. The primary suite as well as two other sizable bedrooms and bath complete this level. There are multiple points within the home granting easy access to several decks offering wonderful opportunities for entertaining or enjoying private time outdoors. The spacious 2 car garage offers great storage and shelter for vehicles, and the newly added driveway adds to the abundance of parking, Located on a quiet street, this location offers easy access to all the local amenities.

This charming Nantucket-style villa offers the perfect blend of coastal elegance and modern upgrades. Featuring two inviting brick patios, two storage sheds, and beautiful wide pine floors, the home has been thoughtfully updated throughout and is being sold fully turn-key, including high-quality appliances. Located in the highly desirable seaside village of Maushop, you'll enjoy access to a private sandy beach just steps from your door. The first floor boasts an open-concept layout, with a bright living room flowing seamlessly into a stylish kitchen complete with granite bar seating and upscale stainless steel appliances. Relax or entertain on the elevated front brick patio, or take a short stroll to the nearby Popponesset Marketplace, where you'll find boutique shops, restaurants, mini golf, and the popular Raw Bar. Mashpee Commons is also just a short distance away, offering even more dining and shopping options. For those seeking an enhanced lifestyle experience, inquire about membership at The Club at New Seabury, featuring a private beach and cabana club, tennis and pickleball courts, swimming pools, a state-of-the-art athletic center, and more.

Sited in the desirable Greensward Village of New Seabury, this delightful contemporary ranch welcomes you. Mature trees surround the residence w/ garden paths and multiple patio areas creating your private, tranquil retreat. This well maintained home is designed in 2 wings w/abundant windows & sliding glass doors to bring the lovely outdoors inside. The main wing features an inviting living room w/gas fireplace, dining area & updated kitchen w/ granite counters & stainless appliances and primary bedroom w/ walk in closet & en suite bath. Down the hall is a stairway to the loft/office space, washer/dryer and entrance to an attached 2 car garage. The left wing includes a comfortable family room, guest bedroom, 2 single 'bunk' rooms & full bath. This special property is conveniently located to the Popponesset Marketplace & Inn, New Seabury Clubs (available by membership) and nearby Mashpee Commons. Call for appointment - Easy to show.

Best value in gated sought-after Ockway Village! Similar floor plans have closed over $1,900,000.00. Forsythia style Cottage home is located off the main road, behind the gates, in a quiet interior setting. Dramatic vaulted ceiling adds an airy sunlit flooded space. Stunning heart of the home kitchen, fabulous light fixtures complete this flexible, indoor-outdoor flow, kitchen & dining space perfect for entertaining. Deeper foundation pour prepped for a future finished media, full bath & egress for a future 4th bedroom. Finishing this lower level could add another 1,000 + square feet! Need an office, gym or theatre room? One of only five gated neighborhoods in New Seabury, Ockway Village was thoughtfully designed to have airy light filled spaces, low maintenance, sophisticated finishes and design, all while still offering a quiet neighborhood with private heated pool, easy access to maintained walking paths. You are never far from the many amenities offered in New Seabury!

A truly exceptional estate offering unparalleled luxury and resort-style living. This custom-built, 3-bedroom home boasts a captivating open-concept floor plan highlighted by soaring vaulted ceilings, gleaming hardwood floors, creating a bright and expansive atmosphere. The exquisite primary suite offers a private sanctuary on the 1st level as well as 2 other large, carpeted bedrooms both with ensuite bath. Beyond the main house, discover a 3-car garage with a private, fully appointed guest suite above, ideal for visitors or extended family. Step outside to your personal oasis, featuring a heated in-ground pool and bubbling hot tub, all nestled within a meticulously landscaped .7-acre lot adorned with charming stone walls and mature planting for extra privacy. A separate pool house provides ultimate convenience, complete with a kitchenette, full bath, laundry & AC. For the avid golfer or entertainer, the lower level reveals a professional 9-hole putt-putt course offering endless enjoyment. Adjacent to this unique amenity, a dedicated TV/ping pong playroom provides additional recreation space. Schedule your private tour today to experience this remarkable find. Total square footage includes lower level, Guest Suite over garage and pool house.

Treasure the beauty and joy of Popponesset ownership while also capturing the uniqueness of this wonderful home! It is a rare opportunity to find a spacious 4 bedroom home, 2 of the bedrooms with private baths and the other two with connecting bath; a full basement with a finished great room, half bath, walk out, and direct access to one car garage. The home is out of the flood zone, has a whole house generator, open living/dining/ family room area, laundry room, and drenched in natural light! All these features in one home is quite unusual in Popponesset! With easy access to private Poppy beaches and the beautiful Popponesset Spit, as well as the Community House for children and adult activities - there is little left to be desired! Don't miss the opportunity to own this unique property, and transform it into your perfect Popponesset Paradise! The Poppy Marketplace and Mashpee Commons are nearby for shopping, eating, mini-golf, etc

Welcome to 15 Periwinkle Lane, a beautifully remodeled Cape-style home in the desirable Summersea village of New Seabury. Offered turnkey and tucked away on a peaceful dead-end street abutting protected green space, this exceptional property offers the perfect blend of privacy, comfort, and coastal living. Ideally located just 0.3 miles from the New Seabury Marina and approximately 1 mile from the coveted Popponesset Spit Beach. Designed for both everyday living and entertaining, this home features 3 finished levels with 4 bedrooms, 3 full bathrooms, and central air conditioning throughout. The designer kitchen is beautifully appointed with custom cabinetry and shelving, Silestone countertops, Bosch appliances including electric wall oven, gas cooktop, and dishwasher as well as a Fisher & Paykel refrigerator. These premium finishes blend style, functionality, and modern sophistication. The adjoining dining room features custom built-ins and a wine refrigerator, creating an inviting space for entertaining family and friends. The 1st floor primary suite offers a beautifully renovated bathroom featuring a glass-enclosed walk-in rain shower with hand held and wall jets. The 2nd floor includes 2 additional bedrooms with ample storage and a full bathroom with tub/shower including sliding glass door. The spacious walkout lower level provides exceptional flexibility with a private bedroom, full bathroom including 6' walk-in shower, laundry room, and a 2nd living room with wood burning fireplace, making it ideal for guests, extended family, or multigenerational living. This meticulously maintained home has been thoughtfully updated: new roof, Azek front deck with pergola, mahogany front door, 2 new asphalt driveways, new paver walkways trimmed in cobblestone, landscaping, a new water heater, and a natural gas house Generac generator, providing comfort and peace of mind year-round. Additional highlights include oak flooring, natural gas heat, town water, an outdoor shower, and a 2-bay carport. Outdoor living is just as impressive, with a tranquil backyard designed for relaxing and entertaining. Enjoy multiple patios, a side deck, and an outdoor bar, all surrounded by mature landscaping and peaceful green space. Move right in and experience the best of Cape Cod living in one of New Seabury's most sought-after villages, just moments from the marina, beaches, golf, dining, and everything this exceptional coastal community has to offer. Passing title 5 Septic system!

Waterfront home with Deep-Water dock on Popponessett Island, within New Seabury! Rare opportunity to own an exceptional contemporary with sweeping views of Nantucket Sound & Popponesset Creek. Thoughtfully designed to showcase this spectacular setting, the sun-filled open floor plan features a dramatic floor-to-ceiling wall of glass that frames the breathtaking water views. The large kitchen flows seamlessly into the living room w/a wood-burning FP. The dining area with multiple sliders opens to a spacious deck perfect for outdoor dining, entertaining or taking in the ever-changing scenery. In addition, there is a primary bedroom w/private bath, plus a bedroom and bath. The lower level features a bedroom, bath, den & home office offering flexible living space for family and guests. The generous family room with a bar area has direct access to a waterfront patio and a lush lawn ideal for all your summer gatherings. This home is located at the end of a quiet cul-de-sac surrounded by water. Enjoy easy access to a sandy ocean beach on Nantucket Sound, spend the day boating to Martha's Vineyard, kayaking or simply relax taking in the cool summer breezes & endless water views.

Waterfront South Shore Retreat with Private Dock and Water Views. Set on the edge of Chilmark Pond, this exceptional waterfront residence offers rare privacy, refined design, generous water views and easy pond access. Thoughtfully renovated in 2018, the home blends contemporary sophistication with the calm beauty of its natural surroundings. A private dock on the property provides direct pond access. A beautifully manicured path, leads from the house to the dock, where you can launch across the pond to your own private South Shore beach lot. Of course the new owner also has access to iconic Lucy Vincent and Squibnocket beaches. The property is surrounded by over seven acres of abutting conservation land. The grounds are meticulously designed, with mature landscaping and gardens that feel both timeless and intentional. This is more than a residence. It's the key to your Chilmark lifestyle defined by privacy, water access, and understated elegance.

Place Where Dreams Are Made! Elevated coastal living awaits in this extraordinary waterfront residence nestled within the exclusive enclave of Daniels Island. Perfectly positioned to capture sweeping views of Popponesset Bay and Nantucket Sound, this exceptional home offers an unparalleled blend of elegance, comfort, and the timeless beauty. With impeccable attention to detail, this inviting home provides stunning views from nearly every room while having undergone extensive and tasteful remodeling throughout, as well as tremendous improvements to the outdoor living space, providing endless opportunity for entertaining family and friends. The main level offers an open kitchen/dining and sitting area with adjoining living room, a cozy den area as well as a guest ensuite. Meander to the upper level to discover a sun drenched family room, primary suite including a sitting room and new enlarged primary bath as well as two other spacious bedrooms with bath. The spacious renovated guest area over the garage offers a private retreat for those visiting. Perfectly manicured grounds frame an array of outdoor spaces. A shared dock offers convenient access to all your boating pleasures!

Set high on the north shore with panoramic waterviews of Vineyard Sound and deeded private beach access, this secluded 9.8-acre property occupies a rare setting bordered by conservation land and the Menemsha Hills trail network. The spacious, meticulously maintained residence features a reverse floor plan that accentuates the natural light, soaring ceilings, and breathtaking views. The upper level includes an open-concept kitchen, dining, and living area, along with a private primary suite and dedicated office space. There is a large open deck and a screened porch o n this level, as well as a deck off the primary bedroom suite. Thoughtfully designed for both everyday living and entertaining, the home includes amenities such as air conditioning, a whole-house generator, an integrated sound system, outdoor lighting, and more. Outside, the grounds are equally impressive, featuring a tennis court, landscaped gardens with a water feature, and a large open meadow spanning several acres, all surrounded by mature woodland for exceptional privacy. No neighboring homes are visible from the property. There is ample room to add a swimming pool, and the parcel may offer subdivision opportunities. Ownership also includes rights to Brickyard Beach.

A rare offering on a storied West Falmouth lane, where classic Cape Cod homes meet the beauty of Buzzards Bay with a private sandy association beach only two homes from your door. This exceptional property captures the essence of coastal waterfront living with stunning fresh water pond and ocean views. Lovingly held by the same family for over forty years, this custom-built residence offers more than 3,800 square feet of thoughtfully designed living space, set among peaceful surroundings with sweeping water views and unforgettable sunset skies. Expansive living and gathering areas are oriented to embrace the ever-changing seascape, creating a seamless backdrop for both entertaining and quiet retreat. The home features four generous bedrooms and four full baths, along with a spacious kitchen and dining area, sunroom, formal dining room, and living room, all positioned to take advantage of the scenic vistas. A walkout lower level and attached garage provide excellent storage, game room and flexibility for beach gear, bicycles, and paddleboards. An exceptional opportunity to create your Cape Cod lifestyle in the coveted village of West Falmouth, where coastal charm and natural beauty define everyday living, create your own legacy coastal escape.