The Northeast of the United States is dotted with enchanting island towns that offer a blend of rich history, stunning landscapes, and unique coastal charm. Whether you’re drawn to quiet fishing villages, bustling summer destinations, or secluded retreats, these islands provide a getaway that’s close to home yet feels worlds apart. Join us as we count down the 20 best island towns in the Northeast, each with its own story and hidden treasures waiting to be discovered.
20. Cranberry Isles, Maine
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Nestled off the coast of Mount Desert Island, the Cranberry Isles are a cluster of five small islands that embody the quintessential Maine island life. Little Cranberry Island, also known as Islesford, hosts the Islesford Artists Gallery, a hidden gem showcasing local art inspired by the surrounding beauty. With rugged coastlines, peaceful villages, and an intimate community, the Cranberry Isles offer a serene escape where time seems to slow down. The average price for a 3-4 bedroom home here ranges from $400,000 to $600,000, making it a picturesque yet affordable island getaway.
19. Deer Isle, Maine
Connected to the mainland by a graceful suspension bridge, Deer Isle captivates visitors with its authentic coastal charm. The island’s scenic harbors are dotted with lobster boats, a testament to its thriving fishing industry. Art enthusiasts will appreciate the Haystack Mountain School of Crafts, a lesser-known institution where artisans from around the world come to hone their crafts amidst breathtaking natural surroundings. For those seeking a home with 3-4 bedrooms, prices range from $350,000 to $600,000, reflecting the island’s mix of charm and accessibility.
18. Long Island, New York
Beyond the hustle of New York City, the eastern towns of Long Island unfold into a landscape of pristine beaches and upscale living. The Hamptons, renowned for their luxury homes and celebrity residents, offer beautiful beaches like Cooper’s Beach in Southampton. At the far tip, Montauk boasts the historic Montauk Point Lighthouse, the oldest in the state. For a hidden treasure, explore the Lavender By the Bay farm in East Marion, where fields of lavender bloom each summer. The average price of a 3-4 bedroom home on Long Island falls between $572,541 and $700,000, reflecting its balance of suburban comfort and metropolitan allure.
17. Islesboro, Maine
A short ferry ride from the mainland brings you to Islesboro, a slender island known for its tranquility and exclusivity. Wealthy summer residents have long cherished this retreat, yet the island maintains a low-key atmosphere. Visit the Grindle Point Sailor’s Museum and Lighthouse, a lesser-known spot where you can delve into maritime history and enjoy panoramic views of Penobscot Bay. For those drawn to its charm, a 3-4 bedroom home on Islesboro typically costs between $495,036 and $699,000.
16. North Haven, Maine
Surrounded by the Fox Islands Thoroughfare, North Haven offers rolling meadows and stunning waterfront vistas. Accessible only by ferry or private boat, this secluded island nurtures an artistic community that thrives in its inspiring setting. The North Haven Arts & Enrichment Center hosts local performances and workshops, a delightful surprise for visitors seeking cultural experiences in a remote locale. Homes with 3-4 bedrooms on North Haven are priced between $531,667 and $715,078, reflecting its exclusivity and natural beauty.
15. Grand Isle, Vermont
Set in the tranquil waters of Lake Champlain, Grand Isle is Vermont’s largest island community. Known for its picturesque landscapes and outdoor activities, it’s a haven for camping, boating, and fishing. Grand Isle State Park is a popular destination, but don’t miss the Hyde Log Cabin, one of the oldest log cabins in the United States, offering a glimpse into 18th-century frontier life. With average home prices ranging from $589,175 to $756,300 for 3-4 bedrooms, Grand Isle offers a balance of historical charm and natural allure.
14. Staten Island, New York
Often overshadowed by its bustling neighbors, Staten Island boasts diverse neighborhoods and rich cultural sites. Take a ride on the free Staten Island Ferry for breathtaking views of the Manhattan skyline and the Statue of Liberty. Explore Historic Richmond Town, a living history village where centuries-old buildings tell the story of early American life. The island’s greenbelt offers extensive trails and parks, a hidden natural oasis within the city. The price of a 3-4 bedroom home ranges from $688,888 to $715,857, reflecting Staten Island’s growing appeal as a suburban enclave within New York City.
13. Cuttyhunk Island, Massachusetts
As the outermost of the Elizabeth Islands, Cuttyhunk is a sanctuary of untouched tranquility. With a population that swells in the summer but remains under 100 residents year-round, it’s perfect for nature lovers seeking solitude. There are no paved roads or tourist traps—just quiet beaches, excellent fishing spots, and the gentle rhythm of island life. Homes with 3-4 bedrooms here are priced between $870,000 and $1,000,000, a reflection of the island’s unique appeal and exclusivity.
12. Fishers Island, New York
Just off the Connecticut coast, Fishers Island is an exclusive retreat known for its pristine beaches and secluded atmosphere. Accessible primarily by ferry from New London, it’s a place where bicycles outnumber cars, and sandy lanes lead to waterfront vistas. The Henry L. Ferguson Museum, a lesser-known attraction, offers insights into the island’s natural history and preservation efforts. For those seeking a 3-4 bedroom home, prices range from $4,900,000 to $5,200,000, emphasizing the island’s exclusivity and prestige.
11. Isles of Shoals, New Hampshire
Shrouded in historical mystique, the Isles of Shoals are a small archipelago steeped in pirate legends and maritime lore. Star Island, one of the few accessible isles, hosts conferences and retreats in its historic Oceanic Hotel. Wander the island to discover hidden cemeteries and tales of Captain Kidd’s buried treasure, all while surrounded by the stark beauty of the sea. A 3-4 bedroom home on these islands typically costs between $1,900,000 and $2,200,000, reflecting their rich history and unparalleled seclusion.
10. Monhegan Island, Maine
Known as an artist’s haven, Monhegan Island has drawn painters and creatives for over a century with its dramatic cliffs and unspoiled landscapes. With no cars on the island, visitors explore by foot along miles of hiking trails. The cliffside trail to Black Head offers stunning ocean views and is a favorite among those seeking both natural beauty and a touch of the wild. The average cost for a 3-4 bedroom home here ranges from $923,000 to $1,100,000, reflecting the island’s exclusive charm and artistic allure.
9. Vinalhaven, Maine
Home to one of Maine’s largest lobster fishing fleets, Vinalhaven offers rugged landscapes and a close-knit community. The island’s granite quarries, once bustling industries, are now serene swimming holes like Lawson’s Quarry—a hidden gem for a refreshing dip. The Vinalhaven Historical Society provides a window into the island’s rich maritime and quarrying history. Homes with 3-4 bedrooms are priced between $349,000 and $456,782, making it a relatively affordable option for island living in Maine.
8. Chebeague Island, Maine
Chebeague Island’s rustic appeal lies in its quiet beaches and traditional New England charm. Accessible by ferry from Portland or Yarmouth, the island is perfect for leisurely bike rides and beachcombing. The Chebeague Island Inn, a beautifully restored 1920s hotel, offers a touch of elegance and a porch with sweeping ocean views—an ideal spot to watch the sunset. A 3-4 bedroom home on Chebeague Island typically costs between $675,911 and $841,762, combining tranquility with convenient mainland access.
7. Peaks Island, Maine
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A short ferry ride from Portland brings you to Peaks Island, a vibrant community with an artistic soul. The island is home to the Umbrella Cover Museum, an offbeat attraction celebrating the mundane in a whimsical way. Rent a golf cart or bicycle to explore the island’s scenic roads, historic battery ruins, and stunning ocean vistas that make it a favorite among locals and visitors alike. For those considering a 3-4 bedroom home, prices range from $530,000 to $830,000, offering a mix of affordability and proximity to Portland.
6. Fire Island, New York
This car-free oasis off Long Island’s south shore is a tapestry of sandy beaches and lively communities. From the bustling boardwalks of Ocean Beach to the serene sands of Watch Hill, Fire Island caters to diverse tastes. Nature enthusiasts will appreciate the Sunken Forest, a rare maritime holly forest hidden behind the dunes—a true natural wonder that few mainlanders know exists. Home prices for 3-4 bedrooms here range from $900,000 to $1,200,000, a testament to its popularity and serene appeal.
5. Shelter Island, New York
Nestled between the North and South Forks of Long Island, Shelter Island lives up to its name with peaceful shores and secluded charm. Nearly one-third of the island is preserved in Mashomack Preserve, a hidden gem of wetlands, woodlands, and coastline that’s perfect for hiking and birdwatching. The island’s tranquil atmosphere makes it a haven for those seeking respite from the hustle and bustle. Homes with 3-4 bedrooms are priced between $1,350,000 and $1,650,000, highlighting its luxurious and private setting.
4. Block Island, Rhode Island
A mere ferry ride from the mainland, Block Island offers miles of pristine beaches and dramatic bluffs. Mohegan Bluffs, with its towering clay cliffs and a challenging staircase to the secluded beach below, is a must-see. The island’s Southeast Lighthouse, perched near the bluffs, adds a historic touch to the stunning landscape. With its laid-back vibe, Block Island is an ideal escape for relaxation. For those drawn to its charm, 3-4 bedroom homes cost between $2,800,000 and $3,000,000, reflecting the island’s upscale allure.
3. Martha’s Vineyard, Massachusetts
Famous for its beautiful beaches and lighthouses, Martha’s Vineyard is a mosaic of diverse and vibrant communities. Explore the colorful Gingerbread Cottages of Oak Bluffs or take a stroll in the serene village of Chilmark. For a lesser-known attraction, visit the Mytoi Japanese Garden on Chappaquiddick Island, a tranquil spot that offers a meditative escape amid manicured landscapes. Homes with 3-4 bedrooms here typically cost $1,500,000 to $1,800,000, emphasizing its reputation as a high-end New England retreat.
2. Nantucket, Massachusetts
With cobblestone streets and classic shingled homes, Nantucket exudes timeless elegance. The Whaling Museum provides a fascinating look into the island’s maritime heritage. For a hidden delight, explore the Coskata-Coatue Wildlife Refuge, a remote sanctuary accessible by four-wheel drive, or a challenging hike, where seals can often be spotted basking on the shorelines. For 3-4 bedroom homes, prices range from $2,100,000 to $2,250,000, solidifying its status as one of the most coveted island locales.
1. Bar Harbor, Maine
Atop our list is the charming seaside town of Bar Harbor on Mount Desert Island. Serving as the gateway to Acadia National Park, it offers breathtaking coastal scenery and a wealth of outdoor activities. Beyond the well-trodden paths, venture to Bubble Rock, a precariously perched glacial erratic offering panoramic views of the park. Bar Harbor’s historic architecture and vibrant downtown make it a destination that captures the heart of every visitor. Homes with 3-4 bedrooms are priced between $630,000 and $797,000, making it a sought-after yet relatively accessible option for island living.
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