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299 Palisado Avenue

Windsor, Connecticut 06095

PENDING$389,900
Beds
4
Baths
1 | 1
SqFt
2,449
Acres
0.55
Year Built
1798
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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2 Fireplaces

About This Home

Own a piece of Windsor's living history. The rear of this remarkable home dates to 1780, with a Greek Revival addition built around 1835 by the Thrall family. In 1874, it was purchased as a summer residence by Joseph Rainey of South Carolina - elected to the U.S. House of Representatives. This 2,500 sq. ft. eclectic home has evolved gracefully through the centuries while honoring its origins: wide-board wood floors, unique built-ins, and two staircases tell the story. The layout flows beautifully for entertaining - from the welcoming front foyer into the generous living room with fireplace insert, past the powder room alcove, through the spacious dining room and butler's pantry, and into the large eat-in kitchen with center island, gas stove, and more built-ins. A step-down den with fireplace opens to a private brick patio out back. Upstairs, the primary bedroom offers an impressively sized closet - a rare luxury in a home of this era. Three additional bedrooms complete the floor, one with a connected office and back-staircase access to the kitchen. A full bathroom and walk-up attic round out the second floor. The home is oil-heated with natural gas already connected for the stove and water heater. Roof replaced just two years ago.

Key Facts

City/Town
Windsor
Neighborhood
N/A
Property / Style
Single Family · Antique
Year Built
1798
Days on Market
50 days
Beds
4
Baths
1 full · 1 half
Living Area
2,449 sq ft
Lot Size
0.55 acres
Garage / Parking
4 total
Property Taxes
$6,825 / Annually

Market Snapshot

The Windsor Market

Single Family · trailing 12 months

Median Days on Market

48

20 active listings

Median $ / Sq Ft

$215

20 active listings

Sale-to-List Ratio

103.2%

255 sales

How this home compares

List Price

$389,900

vs $444,450 median

12.3% below median

Price / Sq Ft

$159

vs $215 median

26.0% below median

Days on Market

50 days

vs 48 days median

In line with median

Based on 20 active and 255 closed sales (trailing 12 mo) of single family in Windsor. Source: SmartMLS · As of July 28, 2026.

Location

299 Palisado Avenue, Windsor, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$2,687

per month

  • Principal & Interest$1,988
  • Property Taxes$569
  • Insurance$130
  • HOA$0

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

Location

City/Town
Windsor
Neighborhood
N/A
County
Hartford

Residence

Property Type
Single Family
Style
Antique
Year Built
1798
New Construction
No/Resale
Living Area
2,449 sq ft

Schools

Elementary
Oliver Ellsworth
High
Windsor

Interior

Heating
Hot Water
Heat Fuel
Natural GasOil
Cooling
Window Unit
Fireplaces
2
Laundry
Main Level
Laundry Location
Laundry closet in den
Appliances
Gas RangeRefrigeratorDishwasherWasherElectric Dryer
Basement
FullUnfinishedFull With Hatchway
In-Law Apartment
No

Exterior & Lot

Lot Size
0.55 acres
Zoning
AA
Garage / Parking
4 total parking spacesDrivewayCrushed Stone
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Septic
Construction
Clapboard
Roof
Asphalt Shingle
Foundation
Masonry
Exterior Features
ShedPatio
Lot Description
TreedLevel Lot

Listing & Financials

Property Taxes
$6,825 / Annually
Days on Market
50
MLS #
24179838
MLS Status
Under Contract - Continue to Show
Financing
FHA,VA,CHFA

Similar Properties

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

Listed By

Mary Beth Welsh

(860) 995-5649

Century 21 AllPoints Realty

(860) 521-0021

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 5:15 AM UTC.