Historic Nantucket Homes

Historic · Greek Revival · Town

94 Main Street

The Hadwen-Wright House

The Hadwen-Wright House, one of Nantucket’s celebrated “Two Greeks,” paired a monumental Corinthian portico with preserved nineteenth-century craftsmanship, a domed former ballroom adapted as a primary suite, a belvedere and an original brick-lined well. The sellers selected Bernadette Meyer following her representation of 72 Main Street and because of the Sotheby’s affiliation, which held personal significance for one owner. Before public launch, she approached a small circle of trusted agents; one introduced a buyer who submitted an offer after a single hour-long visit. A Mary Bergman feature and a Storied Streets video also formed part of the property’s presentation, conveying its architectural and cultural history beyond the usual listing details.

5 BD | 6.5 BA | 6,106 SQ.FT.

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Historic · Coastal Compound · Ocean Views

1 Ocean Avenue

Built in 1920, this established Sconset estate combined an early-twentieth-century main residence with three distinct guest and recreational dwellings: The Rec Cottage, The Stable and The Chauffeur’s Cottage. Set across three parcels overlooking the Atlantic, the compound retained the character of a longstanding summer retreat while providing independent accommodation for family and guests. Its generous grounds, panoramic water views and unusually flexible four-building arrangement were distinctive attractions for a buyer seeking a multigenerational Nantucket property.

12 BD | 11 BA | 11,564 SQ.FT.

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Historic · Town · Distant Harbor Views

13 Orange Street

Dating to approximately 1800, 13 Orange Street paired preserved historic details with modern living across three finished levels. Its light-filled kitchen opened onto a stone patio and an unusually deep, private garden for a Town address. Formal and informal gathering rooms, two off-street parking spaces and a roof walk with distant harbor views added to its flexibility. The combination of architectural character, outdoor space and potential for additional improvements made this an especially adaptable in-town residence.

5 BD | 5 BA | 3,390 SQ.FT.

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Historic · Renovated · Town

32 Pine Street

Built in 1841, this renovated antique home on Pine Street preserved the atmosphere of historic Nantucket while accommodating contemporary daily life. Original architectural features and a traditional staircase sat alongside an updated kitchen, a comfortable living and dining area and French doors leading to a private garden and patio. A first-floor room with a fireplace could function as either a bedroom or study. The quiet location close to Main Street, off-street parking and flexible layout offered strong appeal for year-round or seasonal use.

3 BD | 3 BA | 2,028 SQ.FT.

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Historic · Greek Revival · Town

72 Main Street

Constructed in 1822, 72 Main Street stood as one of Nantucket’s prominent historic Main Street residences. Its portico with Ionic columns, formal parlors, original details and richly finished interiors reflected the island’s early-nineteenth-century architectural heritage. The house had been carefully preserved while discreet modern updates supported contemporary living. A private garden and outdoor entertaining spaces added to the appeal of this substantial in-town property, allowing a buyer to acquire a distinguished historic residence without sacrificing comfort or convenience.

6 BD | 6.5 BA | 6,804 SQ.FT.

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Historic · Sconset · Ocean Views

23 Front Street

Dating to around 1820, 23 Front Street was a traditional Sconset summer cottage overlooking Codfish Park and the Atlantic Ocean at the beginning of the Bluff Walk. The property’s history was described as including early use as a fish house and boathouse, and it retained the unpretentious character of a much-loved seasonal home. A covered porch, simple historic interiors and exceptional coastal outlook created an unusual opportunity for a buyer drawn to Sconset’s early cottage tradition and close relationship with the sea.

4 BD | 2 BA | 1,344 SQ.FT.

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Historic · Restored · Town

21 Milk Street

Originally dating to 1750, this Milk Street residence had undergone a careful restoration by Twig Perkins that retained its historic character while introducing substantial modern improvements. Six fireplaces, multiple living spaces and original architectural elements were complemented by a new kitchen with double islands and a cathedral ceiling, together with a first-floor primary suite. Its position a short distance from Main Street, landscaped grounds and combination of period craftsmanship with updated amenities made the home particularly compelling for comfortable in-town living.

4 BD | 4 BA

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Historic · Renovated · Town

8 Gull Island Lane

Built around 1740, this historic home occupied a notably private setting on Gull Island Lane. Extensive renovation had modernized the interior while preserving the scale and atmosphere of an early Nantucket residence. Living and dining rooms, a generous family room and an updated kitchen with a large island supported everyday use, while garden and patio spaces offered quiet outdoor living. The property’s combination of eighteenth-century character, modern convenience and seclusion within walking distance of Town was a distinctive strength.

3 BD | 4 BA | 2,487 SQ.FT.

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Historic · Restored · Town

24 Fair Street

Dating to 1800, 24 Fair Street had been carefully restored while retaining a remarkable collection of original Nantucket details. Eight wood-burning fireplaces, wide pine floors, exposed beams and built-in cabinetry conveyed the character of an early Town residence. At the same time, updated mechanical systems, outdoor space and dedicated parking supported practical ownership. The roof walk’s water views added another distinctive feature, making the property appealing to a buyer seeking architectural authenticity together with modern convenience.

4 BD | 2.5 BA | 2,802 SQ.FT.

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Historic · Town · Conservation Setting

21 Lily Street

Built in 1830, 21 Lily Street offered the familiar proportions and character of an older Nantucket home in a quiet in-town location. The property sat opposite the Lily Pond conservation area and its walking trails, while shops and restaurants were only a short walk away. Its flexible living areas, first-floor bedroom, patio, air conditioning and two off-street parking spaces suited both seasonal visits and year-round use. The combination of protected open space, easy access to Town and private parking offered a practical distinction for buyers considering a historic in-town residence.

4 BD | 3 BA | 2,128 SQ.FT.

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Historic · Restored · Town

8 Ash Street

Built in 1765, this restored five-bay antique residence occupied a quiet cobblestoned street in Nantucket Town. Its traditional double-entry staircase, historic parlors, wood-burning fireplaces and original interior details reflected the craftsmanship of the period, while the updated kitchen and comfortable living spaces supported modern use. Frontage on both Ash Street and Ash Lane provided separate access to a generous lot with gardens, stone walls, a patio and parking for two cars. The potential for expansion or a cottage/garage, subject to applicable approvals, offered a further option beyond the restored residence.

5 BD | 3.5 BA | 4,260 SQ.FT.

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