63 Meadow Street
Winchester, Connecticut 06098
- Beds
- 5
- Baths
- 3
- SqFt
- 2,602
- Acres
- 0.25
- Year Built
- 1900
- Property Type
- 3 Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Discover 63 Meadow, a turnkey 3-unit asset where thoughtful updates, strong rental performance, and a prime location come together to prove a high confidence investment opportunity. The property offers three well-proportioned units, a two-car attached garage, off-street parking spaces, and shared outdoor area that tenants appreciate. The current owner continued to elevate the building's value and safety with electrical upgrades, a new sump pump, new hot water tank, and fire marshal approved improvements throughout the walkways and stairways. Rental rates reflect market, further improving ROI. Unit 1 features two bedrooms, full bath, mudroom with laundry, enclosed front porch, side porch, with interior updated in 2024. Unit (2F) spans the footprint of the first floor and now includes in unit laundry, updated in 2024 with carpeting, fresh paint, creating a bright and functional living space with multiple rooms and a generous walk-in closet. Unit 2R is a cozy 1BR with an eat in kitchen, living room, and updated finishes including paint, countertops, flooring, and toilet (2023). All units offer two egresses, one exterior and one through the common area. Tenants enjoy quick access to Route 8, a local university, and everyday conveniences. A short walk to Dunkin', Red Barn, and only a 2 mile walk to Highland Lake. It's combination of location, upgrades and improvements, and strong rental income already in place, it's a standout addition to any portfolio! AS IS.
Key Facts
- City/Town
- Winchester
- Neighborhood
- N/A
- Property / Style
- Multi-Family · Units on different Floors
- Year Built
- 1900
- Days on Market
- 73 days
- Beds
- 5
- Baths
- 3 full
- Living Area
- 2,602 sq ft
- Lot Size
- 0.25 acres
- Garage / Parking
- 2 garage · 5 total
- Property Taxes
- $3,902 / Annually
Market Snapshot
The Winchester Market
Multi-Family · trailing 12 months
Active Listings
6
7 under contract
Median List Price
$524,450
6 active listings
Median Closed Price
$305,000
17 sales
Median Days on Market
16
6 active listings
Median $ / Sq Ft
$191
6 active listings
Sale-to-List Ratio
100.0%
17 sales
How this home compares
List Price
$345,000
vs $524,450 median
34.2% below median
Price / Sq Ft
$133
vs $191 median
30.4% below median
Days on Market
73 days
vs 16 days median
57 days longer than median
Based on 6 active and 17 closed sales (trailing 12 mo) of multi-family in Winchester. Source: SmartMLS · As of July 28, 2026.
Location
63 Meadow Street, Winchester, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$1,759
- Property Taxes$325
- Insurance$115
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Winchester
- Neighborhood
- N/A
- County
- Litchfield
Residence
- Property Type
- Multi-Family
- Subtype
- 3 Family
- Style
- Units on different Floors
- Year Built
- 1900
- New Construction
- No/Resale
- Living Area
- 2,602 sq ft
Schools
- Elementary
- Per Board of Ed
- Middle
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Water
- Heat Fuel
- Natural Gas
- Cooling
- None
- Laundry
- Hook-Up In Unit 1Hook-Up In Unit 2
- Laundry Location
- Units 1 and 2
- Basement
- FullUnfinished
Exterior & Lot
- Lot Size
- 0.25 acres
- Zoning
- R-3
- Garage / Parking
- 2 garage spaces5 total parking spacesAttached GaragePavedOff Street ParkingDrivewaySharedPaved
- Waterfront Details
- Walk to Water
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Vinyl Siding
- Color
- Navy Blue
- Roof
- Asphalt Shingle
- Foundation
- ConcreteStone
- Exterior Features
- Porch-EnclosedSidewalkShedPorchCovered Deck
- Lot Description
- Level Lot
Listing & Financials
- Property Taxes
- $3,902 / Annually
- Days on Market
- 73
- MLS #
- 24175107
- MLS Status
- Under Contract
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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 6:10 AM UTC.