299 Palisado Avenue
Windsor, Connecticut 06095
- Beds
- 4
- Baths
- 1 | 1
- SqFt
- 2,449
- Acres
- 0.55
- Year Built
- 1798
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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
Active Listings
20
41 under contract
Median List Price
$444,450
20 active listings
Median Closed Price
$385,000
255 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per 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
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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 5:15 AM UTC.