143 Holabird Avenue
Winchester, Connecticut 06098
- Beds
- 8
- Baths
- 4 | 1
- SqFt
- 4,800
- Acres
- 0.64
- Year Built
- 1925
- Neighborhood
- Winsted
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
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About This Home
One of the finest grand classic Colonial homes where timeless charm and beautiful details can still be found throughout. Features include elegant crown molding, rich wood paneling, wide baseboard molding, gleaming hardwood floors, and a sweeping grand staircase-all adding to the warmth and character of this truly special home. This home features formal dining room, sitting room with fireplace, remolded kitchen offering two sinks, granite counter large palladium windows allowing in natural light a main floor study with fireplace /built in bookshelves. On second floor are 6 bedrooms and 3 full baths, primary bedroom has unique alcove with sink /dressing area. Vintage Blue stone patio is for quiet times to enjoy watching the wildlife, or you can play a game of billiards on the standard size table in the game room. Only three families have lived in this elegant 101 year young home. A home filled with elegance, history and warmth All this elegance can be yours. Wonderful home for extended family or possible Bed & Breakfast. There is many possibilities with this property. Minutes from Rt 8, easy drive to Bradley Airport, enjoy recreation at Highland lake.
Key Facts
- City/Town
- Winchester
- Neighborhood
- Winsted
- Property / Style
- Single Family · Colonial
- Year Built
- 1925
- Days on Market
- 25 days
- Beds
- 8
- Baths
- 4 full · 1 half
- Living Area
- 4,800 sq ft
- Lot Size
- 0.64 acres
- Garage / Parking
- 2 garage · 6 total
- Property Taxes
- $11,876 / Annually
Market Snapshot
The Winchester Market
Single Family · trailing 12 months
Active Listings
21
9 under contract
Median List Price
$389,900
21 active listings
Median Closed Price
$340,000
95 sales
Median Days on Market
25
21 active listings
Median $ / Sq Ft
$231
21 active listings
Sale-to-List Ratio
100.0%
95 sales
How this home compares
List Price
$629,000
vs $389,900 median
61.3% above median
Price / Sq Ft
$131
vs $231 median
43.3% below median
Days on Market
25 days
vs 25 days median
In line with median
Based on 21 active and 95 closed sales (trailing 12 mo) of single family in Winchester. Source: SmartMLS · As of September 15, 2026.
Location
143 Holabird Avenue, Winchester, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 10, 2026per month
- Principal & Interest$3,267
- Property Taxes$990
- Insurance$210
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Winchester
- Neighborhood
- Winsted
- County
- Litchfield
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1925
- New Construction
- No/Resale
- Living Area
- 4,800 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Radiator
- Heat Fuel
- Oil
- Cooling
- None
- Fireplaces
- 3
- Laundry
- Main Level
- Appliances
- Oven/RangeRange HoodRefrigeratorDishwasher
- Basement
- FullPartially FinishedPartial With Walk-Out
- In-Law Apartment
- PossibleUpper Level
- Interior Features
- Security System
Exterior & Lot
- Lot Size
- 0.64 acres
- Zoning
- res
- Garage / Parking
- 2 garage spaces6 total parking spacesDetached GaragePavedDrivewayPrivatePaved
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Wood
- Color
- White
- Roof
- Asphalt ShingleOther
- Foundation
- MasonryStone
- Exterior Features
- GuttersPatio
- Lot Description
- Lightly WoodedLevel Lot
Listing & Financials
- Property Taxes
- $11,876 / Annually
- Days on Market
- 25
- MLS #
- 24200869
- MLS Status
- Active
Similar Properties
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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 9/15/2026. 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 9/15/2026 at 8:00 PM UTC.