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1653 Main Street

South Windsor, Connecticut 06074

ACTIVE$1,450,000
Beds
4
Baths
2 | 1
SqFt
4,480
Acres
5.47
Year Built
1757
Matt Caiola

Matt Caiola

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2-Car Garage7 Fireplaces

About This Home

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.

Key Facts

City/Town
South Windsor
Neighborhood
East Windsor Hill
Property / Style
Single Family · Antique
Year Built
1757
Days on Market
31 days
Beds
4
Baths
2 full · 1 half
Living Area
4,480 sq ft
Lot Size
5.47 acres
Garage / Parking
2 garage · 12 total
Property Taxes
$14,541 / Annually

Market Snapshot

The South Windsor Market

Single Family · trailing 12 months

Median Days on Market

23

24 active listings

Median $ / Sq Ft

$217

24 active listings

Sale-to-List Ratio

103.5%

205 sales

How this home compares

List Price

$1.45M

vs $489,450 median

3.0× the median

Price / Sq Ft

$324

vs $217 median

49.3% above median

Days on Market

31 days

vs 23 days median

8 days longer than median

Based on 24 active and 205 closed sales (trailing 12 mo) of single family in South Windsor. Source: SmartMLS · As of July 28, 2026.

Location

1653 Main Street, South Windsor, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$9,088

per month

  • Principal & Interest$7,393
  • Property Taxes$1,212
  • Insurance$483
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
South Windsor
Neighborhood
East Windsor Hill
County
Hartford

Residence

Property Type
Single Family
Style
Antique
Year Built
1757
New Construction
No/Resale
Living Area
4,480 sq ft

Schools

Elementary
Per Board of Ed
High
Per Board of Ed

Interior

Heating
Hot AirZoned
Heat Fuel
Gas In Street
Cooling
Central AirZoned
Fireplaces
7
Laundry
Upper Level
Appliances
Gas CooktopOven/RangeMicrowaveRange HoodRefrigeratorFreezerDishwasherDisposalWasherGas DryerWine Chiller
Basement
FullFull With Hatchway
Interior Features
Auto Garage Door OpenerSecurity System
Additional Rooms
Laundry Room

Exterior & Lot

Lot Size
5.47 acres
Zoning
A40
Garage / Parking
2 garage spaces12 total parking spacesDetached GarageDrivewayPrivateCrushed Stone
Waterfront Details
Walk to WaterAccess
Water Source
Private Well
Sewer
Septic
Construction
Clapboard
Color
Green
Roof
Slate
Foundation
ConcreteStone
Exterior Features
ShedBarnPatio
Lot Description
Level LotRolling

Listing & Financials

Property Taxes
$14,541 / Annually
Days on Market
31
MLS #
24187374
MLS Status
Active
Financing
FHA,VA,CHFA

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Jacob Wint

(413) 531-1535

William Pitt Sotheby's Int'l

(860) 777-1800

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 7/28/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.

Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.

Data last updated on 7/28/2026 at 6:05 AM UTC.