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63 Meadow Street

Winchester, Connecticut 06098

PENDING$345,000
Beds
5
Baths
3
SqFt
2,602
Acres
0.25
Year Built
1900
Matt Caiola

Matt Caiola

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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

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

Property + 11 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$2,199

per 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

Similar Properties

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

Listed By

Lauren Hill

(203) 927-3411

Mark Tavares Realty, LLC

(203) 720-7172

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.