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205 Old New Hartford Road

Winchester, Connecticut 06098

ACTIVE$499,900
Beds
6
Baths
5
SqFt
2,864
Acres
1.00
Year Built
1900
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
Higgins Group Private Brokerage

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About This Home

Charming Multi-Family Property with steady income potential! Welcome to your next lucrative investment venture! Nestled on an expansive 1-acre lot, this multi-family property features 5 distinct living spaces, making it an ideal addition to your real estate portfolio. This property comprises 4 studio apartments and a spacious 2-bedroom apartment, catering to a variety of tenants and maximizing rental income. With a current monthly gross income of $4,200, you can enjoy steady cash flow while benefiting from an increasingly competitive rental market. Located in a desirable neighborhood with public water and access to public sewer, this property is perfectly positioned to attract long-term tenants. Its proximity to local amenities, schools, and public transportation enhances its appeal, ensuring high occupancy demand. Each unit boasts separate electrical meters, providing tenants with individual control over their utilities. The common laundry facilities in the basement offer added convenience for residents, further enhancing the livability of the space. Recently paved parking enhances accessibility for both residents and guests, while dual heating units ensures comfort during colder months. This property is not only inviting but also functional, providing a hassle-free living experience for tenants. It also comes with established tenants, solid rental history, and a reliable mechanicals, allowing you to step into a well-oiled investment without the headaches of initial setup.

Key Facts

City/Town
Winchester
Neighborhood
N/A
Property / Style
Multi-Family · Other
Year Built
1900
Days on Market
65 days
Beds
6
Baths
5 full
Living Area
2,864 sq ft
Lot Size
1.00 acres
Garage / Parking
10 total
Property Taxes
$4,519 / Annually

Market Snapshot

The Winchester Market

Multi-Family · trailing 12 months

Median Days on Market

17

6 active listings

Median $ / Sq Ft

$191

6 active listings

Sale-to-List Ratio

100.0%

17 sales

How this home compares

List Price

$499,900

vs $524,450 median

In line with median

Price / Sq Ft

$175

vs $191 median

8.4% below median

Days on Market

65 days

vs 17 days median

48 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 29, 2026.

Location

205 Old New Hartford Road, Winchester, Connecticut

Property + 10 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$3,093

per month

  • Principal & Interest$2,549
  • Property Taxes$377
  • Insurance$167
  • 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
5 Family+
Style
Other
Year Built
1900
New Construction
No/Resale
Living Area
2,864 sq ft

Schools

Elementary
Per Board of Ed
Middle
Per Board of Ed
High
Per Board of Ed

Interior

Heating
Hot Air
Heat Fuel
Oil
Cooling
Window Unit
Laundry
Common Laundry Area
Laundry Location
Basement
Basement
FullStoragePartially FinishedWalk-outFull With Walk-Out

Exterior & Lot

Lot Size
1.00 acres
Zoning
R-1
Garage / Parking
10 total parking spacesPavedOff Street ParkingDrivewayPaved
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Public Sewer In StreetSeptic
Flood Zone
No
Construction
Aluminum
Color
White
Roof
Asphalt Shingle
Foundation
ConcreteStone
Exterior Features
Gutters
Lot Description
Sloping Lot

Listing & Financials

Property Taxes
$4,519 / Annually
Days on Market
65
MLS #
24178149
MLS Status
Active

Similar Properties

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Listed By

TK Krumm

(860) 370-9473

Berkshire Hathaway NE Prop.

(860) 653-4507

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 7/29/2026. 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 7/29/2026 at 11:45 AM UTC.