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25 Oak Avenue, Oak Bluffs
$1,950,000
2 Beds ⋅ 2 Baths ⋅ 73593599 MLS
Thought to have been moved from the Campgrounds to the Highlands in the early 1900's, the Mary E. Gilkes house has been transformed into a sophisticated and easy-living Island abode. The thoughtful, intentional design and execution of this renovation/addition pays homage to its Victorian roots while adding every modern amenity for year-round or summer use. Every detail has been carefully considered from the mahogany front porch with Vineyard-blue ceilings that typifies the Oak Bluffs cottage history, to the "bonus" room/loft, to infrastructure which meets HERS requirements for energy efficiency. There isn't an inch of wasted space in this little powerhouse and the property offers a wealth of possibilities for expansion. The location is quiet and bucolic, and just up the hill from Circuit Ave., with easy access to East Chop and Eastville Beach. Roll right off the ferry and bring your Vineyard vision to life in this enchanting home where history, style and modern comfort come together!

25 Oak Avenue, Oak Bluffs

20 Hidden Cove, Oak Bluffs
$1,595,000
4 Beds ⋅ 3 Baths ⋅ 73577547 MLS
Set within the sought-after Hidden Cove community, a 65-acre private enclave with direct access to Sengekontacket Pond, this contemporary retreat offers an exceptional Martha’s Vineyard lifestyle. Residents enjoy a private community boat dock, scenic walking trails, pickleball and tennis courts, all just moments from Oak Bluffs and Edgartown.Set on a private, wooded lot, the home blends classic Vineyard character with relaxed coastal living. Cedar siding, an expansive wood deck, screened porch, and outdoor shower create inviting spaces for everything from quiet mornings to long summer evenings and post-beach afternoons.Inside, the home unfolds around a striking two-sided gas and wood-burning fireplace, with large windows bringing the surrounding landscape indoors. Four bedrooms offer comfortable space for family and guests, while a finished lower level adds exceptional versatility — currently configured as a media room and home office, with an unfinished portion ready to become a private gym, wine cellar, or whatever you envision.With water access, exceptional community amenities, and a private setting close to the Island’s favorite towns, Hidden Cove offers a rare combination of active outdoor living, privacy, and quintessential Vineyard ease.

20 Hidden Cove, Oak Bluffs

267 Barnes Road, Oak Bluffs
$4,395,000
3 Beds ⋅ 6 Baths ⋅ 73572956 MLS
Set along 163 feet of Lagoon frontage with its own sandy beach, 267 Barnes Road offers a fresh, contemporary take on waterfront living in Oak Bluffs. Set on 1.25 acres, the 4,046-square-foot home balances privacy with comfortable spaces for entertaining or relaxing. Oversized windows bring Lagoon views into nearly every room. The main level features soaring ceilings, a wood-burning fireplace, wet bar, and an eat-in kitchen opening to a sunny patio. A separate two-room wing with full bath and private deck offers flexible space for an office, den, studio, or guest accommodations. Upstairs, the primary suite includes a fireplace, walk-in closets, ensuite bath, and Lagoon-facing deck. Two additional ensuite bedrooms open to a wraparound deck and 3-season porch. The refinished 2,000-square-foot walk-out lower level includes a full bath, laundry, and space for a gym, media room, or additional living area. Offered fully furnished, this waterfront retreat is ready to enjoy. Whether you are hosting a full house or savoring a quiet weekend, the Lagoon becomes your backdrop: sunrise coffees, afternoon swims, and sunset gatherings right at the water’s edge.

267 Barnes Road, Oak Bluffs

27 Double Ox Rd, 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

7 Ploughshare Lane, Oak Bluffs
$1,399,000
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

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