1653 Main Street
South Windsor, Connecticut 06074
- Beds
- 4
- Baths
- 2 | 1
- SqFt
- 3,584
- Acres
- 5.47
- Year Built
- 1757
- Neighborhood
- East Windsor Hill
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
Turn-key luxury on nearly 6 private acres meets irreplaceable New England character. This fully renovated historic estate delivers modern comfort with zero compromises - new structural beams, all-new electrical, plumbing, complete HVAC, and a Generac hookup, so every major system is already done. The chef's kitchen is the showpiece: professional BlueStar appliances, a Miele espresso machine, a two-zone wine fridge, and a butler's pantry. The deluxe primary suite includes reclaimed wood flooring and its own new full bath, and a custom office with built-ins makes working from home effortless. Every room simply feels right - high ceilings, grand millwork, and seven working fireplaces set the tone throughout, perfect for hosting or quiet nights in. A one-of-a-kind central staircase, with its original spiral-turned balusters, anchors the home as a true architectural centerpiece. Set back from quiet, historic Main Street, an expansive stone terrace and retaining walls against landscaped, private grounds - just minutes from town, Bradley airport, and access to NYC / Boston. A rare bonus: this move-in-ready National Register Georgian Colonial (c. 1757-58) is a celebrated Grant family home, connecting it to the family of Ulysses S. Grant. With its own dedicated Wikipedia page, original wood paneling, and one of the finest surviving CT River Valley doorways, it remains an important piece of New England architecture - modern luxury layered over genuine, documented American history.
Key Facts
- City/Town
- South Windsor
- Neighborhood
- East Windsor Hill
- Property / Style
- Single Family · Colonial,Antique
- Year Built
- 1757
- Days on Market
- 0 days
- Beds
- 4
- Baths
- 2 full · 1 half
- Living Area
- 3,584 sq ft
- Lot Size
- 5.47 acres
- Garage / Parking
- 2 garage · 8 total
- Property Taxes
- $14,541 / Annually
Market Snapshot
The South Windsor Market
Single Family · trailing 12 months
Active Listings
24
37 under contract
Median List Price
$486,950
24 active listings
Median Closed Price
$500,000
203 sales
Median Days on Market
20
24 active listings
Median $ / Sq Ft
$209
24 active listings
Sale-to-List Ratio
104.1%
203 sales
How this home compares
List Price
$1.45M
vs $486,950 median
3.0× the median
Price / Sq Ft
$405
vs $209 median
93.8% above median
Days on Market
0 days
vs 20 days median
20 days fresher than median
Based on 24 active and 203 closed sales (trailing 12 mo) of single family in South Windsor. Source: SmartMLS · As of August 11, 2026.
Location
1653 Main Street, South Windsor, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 6, 2026per month
- Principal & Interest$7,478
- 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
- Colonial,Antique
- Year Built
- 1757
- New Construction
- No/Resale
- Living Area
- 3,584 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot AirZoned
- Heat Fuel
- Gas In Street
- Cooling
- Central Air
- Fireplaces
- 7
- Laundry
- Upper Level
- Laundry Location
- Laundry Room Upstairs
- Appliances
- Gas RangeOven/RangeMicrowaveSubzeroIcemakerDishwasherCompactorWasherDryerWine Chiller
- Basement
- FullFull With Hatchway
Exterior & Lot
- Lot Size
- 5.47 acres
- Zoning
- A40
- Garage / Parking
- 2 garage spaces8 total parking spacesDetached GarageDrivewayPrivateCrushed Stone
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Clapboard
- Roof
- Slate
- Foundation
- BlockBrick
- Exterior Features
- TerracePatio
- Lot Description
- Level Lot
Listing & Financials
- Property Taxes
- $14,541 / Annually
- Days on Market
- 0
- MLS #
- 24198321
- 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 8/11/2026. 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 8/11/2026 at 8:50 PM UTC.