1653 Main Street
South Windsor, Connecticut 06074
- Beds
- 4
- Baths
- 2 | 1
- SqFt
- 4,480
- Acres
- 5.47
- Year Built
- 1757
- Neighborhood
- East Windsor Hill
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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
Active Listings
24
35 under contract
Median List Price
$489,450
24 active listings
Median Closed Price
$495,000
205 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per 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
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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.