attractions List of Famous Winchester Buildings & Structures

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List of the famous landmarks that make up the Winchester skyline, listed alphabetically with photos when available. Winchester architectural landmarks as well as other major buildings, dwellings, and other structures in Winchester are included on this list. Information about these Winchester buildings is included on this list, such as when the building first opened and what architectural style it falls under. List includes both new buildings in Winchester and older historic landmarks.

Buildings here include everything from Skillings Estate House to Cole House.

This list answers the question, "What are the most famous buildings in Winchester?"

This is a good reference for research into the historical architecture in Winchester. Famous architectural houses within the city of Winchester are included as well, sometimes by address, other times listed by the name of the original home owner.
Abijah Thompson House is listed (or ranked) 1 on the list List of Famous Winchester Buildings & Structures
Photo: Freebase/GNU Free Documentation License
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Abijah Thompson House


The Abijah Thompson House is an historic house at 81 Walnut Street in Winchester, Massachusetts. The 1.5 story wood frame house was built sometime between 1835 and 1850, and is a fine local example of Gothic Revival style. Its first documented owner, Abijah Thompson, was the first president of the ...more

City/Town: Winchester, Massachusetts, USA

Opened: Jan 01 1835

Style: Gothic Revival architecture

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Abram's Delight


Abram's Delight is a historic home located in Winchester, Virginia. Built in 1754, it is the oldest house in the city. It was owned by the Hollingsworth family for almost 200 years and is typical of the Shenandoah Valley architecture of the Scotch-Irish settlers. The property was added to the ...more

City/Town: Winchester, Virginia, USA

Style: American Colonial

Albert Ayer House is listed (or ranked) 3 on the list List of Famous Winchester Buildings & Structures
Photo: Freebase/GNU Free Documentation License
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Albert Ayer House


The Albert Ayer House is a historic house at 8 Brooks Street in Winchester, Massachusetts. The 2.5 story wood frame house was built c. 1865, and is a conservative but detailed example of early Italianate architecture. It has wide corner boards, and its porch, which spans the main facade, has ...more

City/Town: Winchester, Massachusetts, USA

Opened: Jan 01 1865

Style: Italianate architecture

Alfred Vinton House is listed (or ranked) 4 on the list List of Famous Winchester Buildings & Structures
Photo: Freebase/GNU Free Documentation License
4

Alfred Vinton House


The Alfred Vinton House is a historic house at 417 Main Street in Winchester, Massachusetts. Gardner Symmes, a local builder, built the Italianate house c. 1854, and may have lived in it before Alfred Vinton, a local lawyer who married into the Symmes family, bought it in 1862. The house is a fine ...more

City/Town: Winchester, Massachusetts, USA

Opened: Jan 01 1854

Style: Italianate architecture