
Nantucket's Grandest Historic Homes
Between 1800 and 1850, Nantucket commanded the world's whaling industry. By 1774, the island accounted for sixty percent of the New England whaling fleet, and the wealth generated transformed a modest Quaker settlement into Massachusetts' wealthiest community.
The sea captains and merchants who built Nantucket's prosperity constructed grand homes befitting their status. Today, these magnificent residences represent the pinnacle of Nantucket real estate, offering a rare opportunity to own a monument to American maritime history.
MARITIME HERITAGE
Nantucket's whaling industry reached its peak in the 1840s, when the island was home to the largest whaling fleet in the world. Captains who successfully completed multi-year voyages to the Pacific returned with fortunes in whale oil and spermaceti.
These successful captains built homes that reflected their worldly experience and considerable wealth. Drawing inspiration from architecture they had seen in ports around the globe, they created residences that were the equal of any in America.
The Great Fire of 1846 destroyed much of downtown Nantucket, but the rapid rebuilding in Greek Revival style produced some of the island's most magnificent structures, including the famous Hadwen House.

DISTINCTIVE CHARACTERISTICS
Whaling captain houses are notably larger than typical period homes, with high ceilings (often 10-12 feet), spacious rooms, and generous proportions that conveyed status and success.
Columned porticos, classical pediments, pilasters, and bold geometric proportions characterize many whaling captain houses, reflecting the popular style of the 1830s-1850s.
Elevated granite foundations distinguish grand homes, raising them above the street and emphasizing their importance. Granite was shipped from the mainland at considerable expense.
Front entrances feature fanlights, sidelights, and decorative surrounds that made a statement about the owner's taste and success. Each doorway is uniquely detailed.
Interior details include elaborate crown moldings, carved mantels, paneled doors, and built-in cabinetry executed by skilled craftsmen using techniques rarely seen in new construction.
Rooftop platforms where wives could watch for returning whaling ships are a romantic feature of some captain's homes, offering harbor and ocean views.
PRESTIGIOUS ADDRESSES
The Grandest Address
Main Street is Nantucket's most prestigious thoroughfare, home to the island's finest whaling-era mansions. The upper portion features the famous Three Bricks built by Joseph Starbuck for his sons, and the Two Greeks at 94-96 Main, considered the finest Greek Revival residences on the island.
Captain's Row
Orange Street rivals Main Street for historic significance, lined with grand homes built by successful whaling captains and merchants. The Levi Starbuck House, believed to inspire the character Starbuck in Moby Dick, stands as a testament to the wealth generated by the whaling industry.
Quiet Elegance
Pleasant Street offers a more residential character while featuring excellent examples of whaling-era architecture. Captains who preferred a quieter setting built substantial homes here, away from the commercial bustle of Main Street while remaining close to the harbor.
Historic Parallel
Running parallel to Main Street, Centre Street features significant whaling-era homes in a somewhat more intimate setting. Sea captains and merchants built substantial residences here, many of which retain their original architectural character.
BUYER'S GUIDE
Whaling captain houses rarely hit the open market. Working with a connected agent provides access to off-market opportunities.
Specialized inspectors understand the unique considerations of 19th-century construction methods and materials.
Understanding any pending HDC matters and the process for future exterior changes is essential.
Historic properties may have complex title histories that require thorough review.
Significant whaling captain houses typically range from $7-15 million, with exceptional Main Street properties commanding $15-25 million or more.
Perhaps 30-50 truly significant whaling captain houses exist on Nantucket. Availability in any given year is extremely limited.
When whaling captain houses come to market, they often sell quickly to buyers who have been waiting for the opportunity.
Working with an agent who continuously monitors the market is essential for securing these rare properties.
HISTORIC SIGNIFICANCE
93, 95, 97 Main Street
Built by Joseph Starbuck in 1836-1838 for his three sons, these matching Georgian brick mansions are among Nantucket's most iconic buildings. Their identical facades present a unified statement of family wealth and prominence.
94, 96 Main Street
Designed by Frederick Brown Coleman, these are considered the finest Greek Revival residences on Nantucket. The house at 94 Main features colossal Corinthian columns, dentils, and modillions in a masterful composition.
96 Main Street
Built in 1846 by whaling merchant William Hadwen at the peak of Nantucket's prosperity. Now a museum operated by the Nantucket Historical Association, it offers insight into the grandeur of whaling-era life.
Orange Street
Built in 1838, this Greek Revival masterwork features unique architectural details including flush siding with projecting paneled pilasters. Levi Starbuck is believed by some to have inspired the character Starbuck in Melville's Moby Dick.
FREQUENTLY ASKED QUESTIONS
Whaling captain houses are grand residences built between 1800-1860 by sea captains who commanded whaling vessels during Nantucket's golden age. These homes are typically larger and more ornate than other period homes, reflecting the wealth accumulated through successful whaling voyages. They often feature Greek Revival or Federal architecture with elaborate details like columned porticos, high ceilings, and fine millwork.
Main Street is home to Nantucket's most famous whaling captain houses, including the Three Bricks built by Joseph Starbuck and the Two Greeks at 94-96 Main. Orange Street features equally significant homes, including the Levi Starbuck House. Pleasant Street and Centre Street also have notable examples of captain's residences from the whaling era.
Whaling captain houses represent the most prestigious properties on Nantucket and are priced accordingly. These grand historic homes typically range from $7-15 million for well-preserved examples, with exceptional Main Street properties or those with significant historic provenance commanding $15-25 million or more. Availability is extremely limited.
Yes, you can modernize the interior while preserving the historic exterior. Many owners update kitchens, bathrooms, and mechanical systems while retaining original architectural details like moldings, fireplaces, and millwork. Exterior changes require Historic District Commission approval, which maintains strict standards for these significant properties.
Key considerations include: working with specialists familiar with historic home inspections, budgeting for ongoing maintenance of period features, understanding HDC requirements for any exterior changes, and appreciating that these homes may have quirks typical of 19th-century construction. The reward is owning an irreplaceable piece of American maritime history.
Rarely. These properties represent a finite inventory of perhaps 30-50 significant whaling captain homes on the island, and many have been held by families for generations. When they do come to market, they typically sell quickly to buyers who have been waiting for the opportunity. Working with a connected local agent who monitors the market is essential.
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