Oak Bluffs Homes with Contemporary Style

Welcome to Oak Bluffs, a charming gem nestled on Martha's Vineyard in Dukes County, Massachusetts. Known for its vibrant atmosphere, Oak Bluffs is a delightful blend of picturesque landscapes, historic architecture, and a lively community spirit. This coastal town boasts stunning beaches, scenic parks, and a bustling harbor, making it an ideal destination for those seeking both relaxation and adventure.

One of the standout features of Oak Bluffs is its unique collection of contemporary-style homes. These modern residences seamlessly blend cutting-edge design with the natural beauty of the island, offering a fresh take on coastal living. With open floor plans, expansive windows, and eco-friendly materials, contemporary homes in Oak Bluffs are designed to maximize space and light, creating an inviting atmosphere that feels both spacious and cozy.

Imagine waking up to the sound of waves crashing against the shore, sipping your morning coffee on a sun-drenched deck, or hosting gatherings in a stylish, airy living room. Many of these homes also feature outdoor spaces that are perfect for entertaining, complete with lush gardens and patios that invite you to enjoy the island's mild climate.

Living in Oak Bluffs means being part of a vibrant community that celebrates art, culture, and the great outdoors. From the renowned Flying Horses Carousel to the stunning Ocean Park, there’s always something to explore. Whether you’re looking for a permanent residence or a vacation retreat, Oak Bluffs offers a unique lifestyle that beautifully marries contemporary living with the charm of island life. Discover your dream home in this enchanting coastal haven today!

Newest Oak Bluffs Homes with Contemporary Style

$3,675,000

4 Beds ⋅ 3 Baths ⋅ 73552922 MLS

Enjoy Spectacular Views From This Chic Island Retreat. Wake up to panoramic Vineyard Sound views, watch the Steamship ferries cross to Woods Hole, and enjoy sunsets stretching down the Lagoon. This turnkey 4-bedroom, 2.5-bath home is designed to embrace its remarkable waterfront setting, with covered decks on both sides capturing ocean breezes and water views from nearly every room. The first floor features three bedrooms, a family room, full bath with laundry, and generous storage. Upstairs, the sun-filled living area includes a gourmet kitchen with Thermador® appliances, Silestone® counters, a gas fireplace, and an open layout that frames stunning Lagoon views. The private primary suite offers vaulted ceilings and a marble bath. High-efficiency heat pumps, central air, solar-ready infrastructure, a strong rental history, and furnishings included make this an exceptional year-round home, vacation retreat, or investment property.

28 Beach Rd, Oak Bluffs

$1,595,000

3 Beds ⋅ 4 Baths ⋅ 73544610 MLS

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.

40 Hidden Cove Road Unit 2 Unit 2, Oak Bluffs

$3,400,000

3 Beds ⋅ 5 Baths ⋅ 73542323 MLS

Set on a private 1.34-acre parcel along a winding paved road in Oak Bluffs, this exceptional to-be-built luxury residence offers the perfect blend of modern sophistication and island charm. The home features over 3,200 square feet of beautifully crafted living space, including a first-floor primary suite, open-concept great room, gourmet kitchen with pantry, and seamless indoor-outdoor living areas. Upstairs are two additional bedroom suites, a loft-style family room/office, dedicated laundry, and flexible bonus room ideal for guests, media, or recreation. A screened porch, covered outdoor living spaces, and attached two-car garage enhance both functionality and lifestyle. Built with high-end finishes and attention to detail throughout, this stunning new construction offering presents an opportunity to own a luxury retreat with easy access to Oak Bluffs' beaches, harbor, restaurants, shops, and all the attractions that make the Vineyard such a sought-after destination.

27 Double Ox Rd, Oak Bluffs

$1,750,000

3 Beds ⋅ 4 Baths ⋅ 22603069 MLS

GORGEOUS NEWER CONSTRUCTION (2023), contemporary farmhouse style home w/ classic wrap around porch & designed w/ Vineyard charm & modern comfort. And yet still there is opportunity to add value to this open concept home, w/ high ceilings, 3 en-suite BRs, laundry on each level, hardwoods throughout. Well designed, fully poured unfinished basement w/ high ceilings, wide open & w/ a separate entrance for an in-law or ADU. 1st FL en suite BR & a common half bath at the foyer entry. Large kitchen w/ full appliances & a 10' stone topped island for large gatherings. Gas fireplace in the family room, sliders to rear yard, a well-designed mudroom area w/ 1st FL laundry, large overflow pantry & a built in bench seating area. The 2nd FL offers 2 en-suite BRs, w/ a large common area. Close to the Lagoon & Sailing Camp Park.Short ride downtown- ideal for year round occupancy and/ or high season rentals. House related plans, professional photos, interior, exterior & aerial video avail upon request.

28 Grovedale Road, Oak Bluffs

$1,750,000

3 Beds ⋅ 4 Baths ⋅ 73540119 MLS

GORGEOUS NEWER CONSTRUCTION (2023), contemporary farmhouse style home w/ classic wrap around porch & designed w/ Vineyard charm & modern comfort. And yet still there is opportunity to add value to this open concept home, w/ high ceilings, 3 en-suite BRs, laundry on each level, hardwoods throughout. Well designed, fully poured unfinished basement w/ high ceilings, wide open & w/ a separate entrance for an in-law or ADU. 1st FL en suite BR & a common half bath at the foyer entry. Large kitchen w/ full appliances & a 10’ stone topped island for large gatherings. Gas fireplace in the family room, sliders to rear yard, a well-designed mudroom area w/ 1st FL laundry, large overflow pantry & a built in bench seating area. The 2nd FL offers 2 en-suite BRs, w/ a large common area. Close to the Lagoon & Sailing Camp Park.Short ride downtown- ideal for year round occupancy and/ or high season rentals. House related plans, professional photos, interior, exterior & aerial video avail upon request.

28 Grovedale Road, Oak Bluffs

$1,599,000

3 Beds ⋅ 3 Baths ⋅ 73527741 MLS

Nestled in a quiet cul-de-sac within the coveted Hidden Cove neighborhood, this delightful property offers an exceptional Island lifestyle. The association delivers rare water access via a private dock on Sengekontacket Pond, plus newly resurfaced tennis and pickleball courts. The open-concept layout flows seamlessly from the fireplaced living room and kitchen through the dining area to an expansive screened porch — ideal for entertaining on warm summer evenings. A welcoming front porch provides additional outdoor living space. The main level is completed by a gracious primary suite with a full bath and a convenient half bath. The walk-out lower level features two additional bedrooms, a full bath, and laundry. A one-car garage offers excellent storage for your car, kayaks, or beach gear. Perfectly positioned between Edgartown and Oak Bluffs. Additional bedrooms possible with septic upgrade per BOH

7 Ploughshare Lane, Oak Bluffs

$1,850,000

4 Beds ⋅ 2 Baths ⋅ 73505800 MLS

Quintessential Waterview Farm! Built as a year-round home with the charm of the original cottages, this well-loved retreat awaits its next chapter. The sunny, open floor plan offers two bedrooms and a full bath on each level, with generous gathering spaces throughout. A skylit kitchen is tucked into a corner of the main living area, where a curved wall of glass opens to a deck and private yard. The sunken living room features a fireplace and stairs to a loft seating area. Built in 1978, the home is fully winterized with oil forced-air heat and a partial basement. The south facing half-acre lot abuts an 8-acre forever-wild meadow. A nearby path leads across wildflower fields to the association beach. Set between Farm Neck and Felix Neck, Waterview Farm offers 22 acres of common land, a sandy beach, dock, boat storage, and possible mooring—ready to enjoy now and enhance over time.

22 Old Harbor Lane, Oak Bluffs

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