On nearly an acre in the Borough of Litchfield, the 1775 Benjamin Tallmadge House is a rare offering in the Litchfield Historic District. A decade of museum-quality stewardship under the current owners has produced one of the most thoughtful restorations ever undertaken on a North Street residence, with every original architectural detail preserved. This antique Colonial blends preserved character with thoughtful updates, including original wide-board pine floors, plaster walls, refurbished Indian shutters, 10 fireplaces, and a chef's kitchen with soapstone counters, La Cornue range, butler's pantry, and built-in banquette. Four bedrooms are joined by a third-floor den currently configured as a 5th bedroom.The primary suite features a 2026 expanded glass-and-tile shower, walk-in dressing room, and cedar closets. Grounds by Michael Trapp include a 44-foot gunite pool, planted rooftop deck with 10-foot spa, tea house, gazebo, gas fire pit, and attached 3-car garage. This is the rare offering where architecture, national history, and daily livability all carry equal weight - a Georgian landmark with Revolutionary War provenance, museum-quality restoration, and a Trapp landscape compound, presented in turnkey condition for its next generation of stewardship. The Benjamin Tallmadge House is one of Connecticut's most historically significant residences and a rare opportunity to own a direct link to the founding of the American Republic. Built by Thomas Sheldon (possibly with builder Giles Kilbourn) and home, beginning in 1782, to Colonel Benjamin Tallmadge - George Washington's chief of military intelligence and the organizer of the legendary Culper Spy Ring - the house carries provenance that few American homes can claim. After Tallmadge's visit to Mount Vernon, he added the two elegant columned porches on the north and south facades, a personal architectural homage from one patriot to another that still defines the home's silhouette today.
Sold for $2,600,000
Zillow last checked:
Listing updated:
Bought with:
David P. Gallitto, RES.0766298
Huntsman,Meade & Partners Comp
Source: Smart MLS,MLS#: 24166876
Price history
| Date | Event | Price |
|---|---|---|
| 6/30/2026 | Sold | $2,600,000-5.5%$380/sqft |
Source:  Smart MLS #24166876 Report a problem | ||
| 5/20/2026 | Pending sale | $2,750,000$402/sqft |
Source: Smart MLS #24166876 Report a problem | ||
| 5/1/2026 | Listed for sale | $2,750,000+182.1%$402/sqft |
Source: Smart MLS #24166876 Report a problem | ||
| 5/22/2014 | Sold | $975,000+225%$143/sqft |
Source:  BCMLS #205059 Report a problem | ||
| 10/25/2011 | Sold | $300,000+136.2%$44/sqft |
Source: Public Record Report a problem | ||
| 2/15/2008 | Sold | $127,000-74.3%$19/sqft |
Source: Public Record Report a problem | ||
| 9/13/1999 | Sold | $495,000$72/sqft |
Source: Public Record Report a problem | ||
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