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Rare opportunity to own a piece of Connecticut history. Built c. 1757-58 by Ebenezer Grant, with a 1695 rear ell, this National Registered Georgian Colonial sits on nearly 6 pristine acres in South Windsor's Main Street Historic District. The celebrated CT River Doorway is among the finest in the state. The property's history includes the Revolutionary War confinement of British Gen. Richard Prescott and Loyalist NJ Gov. William Franklin. Structurally saved and engineered with new beams throughout, the 4,480 SF residence flawlessly unites 18th-century soul with 21st-century luxury. The home features seven fireplaces, original Georgian wood paneling, and a one-of-a-kind central staircase with original spiral-turned balusters. Hand-hewn beams remain exposed from 1685, complemented by reclaimed wood flooring in the kitchen and the deluxe primary suite, which boasts its own new full bath. A custom office features built-ins crafted from beautiful reclaimed wood. A spectacular chef's kitchen boasts professional BlueStar appliances, a Miele espresso machine, a two-zone wine fridge, and a butler's pantry. Outside, the property offers landscaped grounds, an expansive stone terrace with retaining walls, an authentic tobacco barn, and historic outbuildings. With all-new electrical, plumbing, full HVAC, and a Generac hookup, this tasteful renovation is fully complete-allowing you to simply move in and enjoy an impeccably modernized piece of history.

Source: Smart MLS, MLS#: 24187374

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  • Property Type
    Residential
  • Lot
    5.47 acres

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Craig Milton

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Owning this Home

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* All calculations are estimates and provided by Reliance Network, for informational purposes only. Actual amounts may vary. ** Assumes 6.50% APR, 20% down payment, and conventional 30-year fixed rate first mortgage. Rates cited are for instructional purposes only; current rates are subject to change at any time without notice. You should not make any decisions based simply on the information provided. Additional required amounts such as taxes, insurance, homeowner association dues, assessments, mortgage insurance premiums, flood insurance or other such required payments should also be considered. Contact your mortgage company for current rates and additional information. Any mortgage broker or insurance agent that may appear is independent and is not affiliated with, endorsed by, or provided by the MLS.

Life at 1653 Main Street


Schools


School data courtesy of LiveBy, Inc.
Ratings are based on a scale of 1-5, with 5 being the highest rating and 1 being the lowest rating. The schools displayed on this website are for informational purposes only and may not represent a complete or up-to-date list. School assignments are subject to change and should be verified directly with the local school district. Please contact the appropriate school district to confirm school zoning and enrollment eligibility for this property.

History

Date Event Value Agent
6/27/2026Source: Smart MLS Added to Database
June 27, 2026
6/28/2024Source: Smart MLS Status Change
Closed
6/28/2024Source: Smart MLS Status Change
Under Contract
5/20/2024Source: Smart MLS Status Change
Under Contract - Continue to Show
5/14/2024Source: Smart MLS Price Reduction
$399,000 -16.0%
4/12/2024Source: Smart MLS Price Reduction
$475,000 -4.8%
4/4/2024Source: Smart MLS Status Change
Active
4/3/2024Source: Smart MLS Added to Database
April 03, 2024
Listing provided courtesy of William Pitt Sotheby's Int'l- MLS# 24187374MLS ProviderContact Information: (413) 531-1535