77 Hubbard Street
Winchester, Connecticut 06098
- Beds
- 6
- Baths
- 2
- SqFt
- 2,699
- Acres
- 0.28
- Year Built
- 1864
- Property Type
- 2 Family
Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
Discover this versatile two-family residence offering a blend of modern updates and timeless charm. Each unit boasts three bedrooms and a full bath, providing ample space and comfort for tenants or multi-generational living. The first-floor unit has been beautifully renovated, featuring a brand-new kitchen with stylish finishes, updated bath, gleaming hardwood floors, and plush new carpet in the bedrooms. This level offers a fresh, move-in-ready appeal that renters or owners will love. The second-floor unit retains its original character, ideal for those looking to add personal touches or appreciate classic details. With newer siding and a recently updated roof, this property promises low-maintenance living. An attached one-car garage adds convenience, making this home as practical as it is attractive. Perfectly suited for investors or buyers seeking extra income potential, this two-family gem is a fantastic find! 1st floor is under construction and will be finished prior to closing
Key Facts
- City/Town
- Winchester
- Neighborhood
- N/A
- Property / Style
- Multi-Family · Units on different Floors
- Year Built
- 1864
- Days on Market
- 623 days
- Beds
- 6
- Baths
- 2 full
- Living Area
- 2,699 sq ft
- Lot Size
- 0.28 acres
- Property Taxes
- $3,816 / 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
$299,900
vs $524,450 median
42.8% below median
Price / Sq Ft
$111
vs $191 median
41.9% below median
Days on Market
623 days
vs 16 days median
607 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
77 Hubbard Street, Winchester, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$1,529
- Property Taxes$318
- Insurance$100
- 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
- Duplex
- Style
- Units on different Floors
- Year Built
- 1864
- New Construction
- No/Resale
- Living Area
- 2,699 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- BaseboardHot Water
- Heat Fuel
- ElectricNatural Gas
- Cooling
- None
- Laundry
- Hook-Up In Unit 1Hook-Up In Unit 2
- Basement
- Full
Exterior & Lot
- Lot Size
- 0.28 acres
- Zoning
- TCR
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer In Street
- Construction
- Aluminum
- Roof
- Asphalt Shingle
- Foundation
- Stone
- Lot Description
- Level Lot
Listing & Financials
- Property Taxes
- $3,816 / Annually
- Days on Market
- 623
- MLS #
- 24059312
- MLS Status
- Under Contract
Similar Properties
Homes with a close match in area, property type, and price.
Listed By
Amy Rio
Better Homes and Gardens Real Estate Executive Real Estate
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 6:15 AM UTC.