205 Old New Hartford Road
Winchester, Connecticut 06098
- Beds
- 6
- Baths
- 5
- SqFt
- 2,864
- Acres
- 1.00
- Year Built
- 1900
- Property Type
- 5+ Family

Matt Caiola
Luxury Real Estate Advisor
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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
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
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per 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
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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 7/29/2026. 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.