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1653 Main Street

South Windsor, Connecticut 06074

ACTIVE$1,299,000

Reduced from $1,450,000

Beds
4
Baths
2 | 1
SqFt
3,584
Acres
5.47
Year Built
1757
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

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2-Car Garage7 FireplacesPrice Reduced

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 · Antique
Year Built
1757
Days on Market
102 days
Beds
4
Baths
2 full · 1 half
Living Area
3,584 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

21

28 active listings

Median $ / Sq Ft

$216

28 active listings

Sale-to-List Ratio

104.7%

215 sales

How this home compares

List Price

$1.30M

vs $462,000 median

2.8× the median

Price / Sq Ft

$362

vs $216 median

67.6% above median

Days on Market

102 days

vs 21 days median

81 days longer than median

Based on 28 active and 215 closed sales (trailing 12 mo) of single family in South Windsor. Source: SmartMLS · As of October 7, 2026.

Location

1653 Main Street, South Windsor, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$8,755

per month

  • Principal & Interest$7,110
  • Property Taxes$1,212
  • Insurance$433
  • 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
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 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
102
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 10/7/2026. 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 10/7/2026 at 7:46 PM UTC.