Summer With the Obamas in 2018? 8 Homes For Sale on Martha's Vineyard

Martha’s Vineyard is the Massachusetts island as renowned for its unspoiled beaches and chill, diverse vibe as it is for its vacationing presidents and summering celebs.

Former President Barack Obama made recent headlines when it was rumored he might buy a plot or two of land on the island (although his spokesman, for now, denied it). But you don’t have to be a former leader of the free world to have a place there—it’s a spectacular seasonal respite for any buyer with a love for island life along the East Coast.

And although we’re headed into the offseason, there’s no time like now to plan for a big splash in 2018.

Located just 4 miles off of the mainland, Martha’s Vineyard has a population of a little over 16,000 that swells to 100,000 in the summer season. A little over half the homes owned on the island are seasonally occupied. And one of those homeowners could be you, if you’re inclined to pick up one of the over 250 homes currently for sale on the island.

And you don’t have to pack your bags and close the shutters as the calendar flips into fall. When the summer vacationers clear out, locals include farmers, fishermen, artists, and writers. The picturesque “up island” towns of Chilmark and West Tisbury are more rural, with farms, horses, and ponds. The very tip of the island, Aquinnah, on stunning cliffs overlooking the Atlantic, is home to the Wampanoag tribe.

If you’re looking to journey across the water and—possibly—run into the Obamas, we’ve highlighted eight awesome options for a sensational summer home next year.

Undisclosed address, Edgartown, MA

Price: $1,750,000
Summer lovin’: Built in 1997, this property offers three beds, 3.5 baths, and 2,436 square feet of living space. Just minutes from the beach, the retreat offers an outdoor shower, lush gardens enjoyed from two upper-floor decks, and an open floor plan.

Edgartown, MA
Edgartown, MA


162 New York Ave, Oak Bluffs, MA

Price: $469,000
Summer lovin’: Locals and vacationers alike will be tempted by this charmer with the relatively reasonable price tag. The two-bedroom home built in 1930 has a back deck perfect for entertaining, and is within easy walking distance to town, the Vineyard’s liveliest.

Oak Bluffs, MA
Oak Bluffs, MA


19 Kent Harbor Rd, Edgartown, MA

Price: $2,595,000
Summer lovin’: This modern masterpiece built in 1969 was recently updated “while adhering to the artistic vision of the original architect,” according to the listing. The property includes access to a private beach and dock.

Kent Harbor Rd. Edgartown, MA
Edgartown, MA


63 Harbor View Ln, Tisbury, MA

Price: $3,895,000
Summer lovin’: Set high on a bluff, this vacation house has views of the harbor and Cape Cod. Nearly a century old, the five-bedroom home has been fully restored while preserving its vintage character. We’re in love with the kitchen pantry and wet bar, and the fact that this place is surrounded by mature plantings for optimum privacy.

63 Harbor View in Tisbury, MA
Tisbury, MA


3 Dunes Rd, Edgartown, MA

Price: $5,500,000
Summer lovin’: Just steps from South Beach—yep, site of the terrifying opening scene from “Jaws”—this luxury home offers “resort-style” amenities, including a pool, putting green, and multiple decks. The pristine 4,700-square-foot property has five bedrooms and seven baths.

Resort-like amenities in Edgartown, MA
Edgartown, MA


51 Peases Point Way, Chilmark, MA

Price: $2,470,000
Summer lovin’: This 1,900-square-foot modernist house built in the early ’60s offers 1,800 feet of Menemsha Pond shoreline for swimming, kayaking, paddle boarding, shellfishing, and shallow-water fishing.

Modernist pond-front property in Chilmark, MA
Chilmark, MA


75 Bay View Ave, Edgartown, MA

Price: $2,350,000
Summer lovin’: Located off of Edgartown on Chappaquiddick (“Chappy” to locals), this 1985 contemporary home is just a hundred feet from the harbor. Water views are visible from every level of the home, which comes with indoor-outdoor living spaces.

Close to the water on Chappaquiddick, MA.
Chappaquiddick, MA.


62 Naushon Rd, West Tisbury, MA

Price: $1,495,000
Summer lovin’: Renovated last year, this four-bedroom, three-level home features a sun deck, private master deck, and backyard patio, plus access to a private beach.

West Tisbury, MA
West Tisbury, MA

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