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$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

$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 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

$1,499,000
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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