Off the coast of Massachusetts lie two of America’s most prestigious island destinations: Nantucket and Martha’s Vineyard. While both islands share a rich maritime heritage and command some of the most coveted real estate in New England, each possesses its own distinct character and allure for the discerning homebuyer.
Distinctive Island Personalities
Nantucket, often referred to as “The Grey Lady” due to its frequent fog and weathered grey-shingled homes, epitomizes refined isolation and preserved history. This smaller, more intimate island maintains strict architectural guidelines that have preserved its whaling-era charm, creating an exclusive atmosphere that attracts those seeking pristine beaches and understated luxury.
Martha’s Vineyard, by contrast, offers a more diverse landscape and social scene. The island’s six towns each present unique characteristics, from the bustling sophistication of Edgartown to the bohemian charm of Oak Bluffs, providing varied lifestyle options for luxury homeowners.
Premier Downtown Destinations
Nantucket Town’s cobblestone streets and gas-lit lanes create an ambiance that transcends time. The historic downtown district, centered around Main Street, features exclusive boutiques, esteemed dining establishments, and impeccably maintained Federal-style mansions.
On Martha’s Vineyard, Edgartown stands as the crown jewel of island sophistication. Its elegant harbor, lined with meticulously maintained captain’s homes, hosts some of New England’s finest restaurants and luxury retailers.
Prestigious Beaches
Nantucket’s Cisco Beach attracts the island’s most affluent residents with its pristine sand and excellent surfing conditions. The exclusive Steps Beach, accessible through private paths from some of the island’s most valuable properties, offers spectacular sunsets and intimate gathering spaces.
Martha’s Vineyard’s Lambert’s Cove Beach, requiring resident passes, provides a secluded haven for homeowners. The private beaches of Chilmark, particularly those along Squibnocket, offer the ultimate in exclusivity and natural beauty.
Prime Real Estate Locations
On Nantucket, the most sought-after properties are found in:
Brant Point: Offering proximity to town and harbor views, with properties regularly commanding over $10 million.
Cliff Road: Featuring expansive waterfront estates with private beaches.
Dionis: Known for its new construction opportunities and spectacular sunsets.
Polpis and Shimmo: Providing luxurious estates with stunning harbor and nature views.
Martha’s Vineyard’s premier locations include:
Katama: A highly desirable Edgartown neighborhood featuring beachfront estates and access to South Beach.
Seven Gates Farm: A private community in West Tisbury known for its expansive acreage and historic charm.
Chilmark’s Squibnocket Farm: Renowned for its oceanfront properties and extensive privacy.
East Chop: Presenting dramatic water views and proximity to Oak Bluffs amenities.
The luxury real estate market on both islands maintains exceptional value due to strict building restrictions and limited inventory. Current entry points for luxury properties start at approximately $3 million, with premier estates ranging from $15 million to over $50 million.
