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Winsted, CT

Residential Income

Winsted, CT Residential Income Properties for Sale

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New Hartford, CT Canton, CT West Simsbury, CT Burlington, CT Torrington, CT Avon, CT Granby, CT Farmington, CT

16 properties

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4-Unit Quadplex with Storage Garage

Updated: Sep 25

4-Unit Quadplex with Storage Garage

99 High Street, Winchester, CT 06098

$575,000

3,012 sqft 0.23 AC lot

Four residential units: one 2‑bedroom, 1.5‑bath apartment and three 1‑bedroom, 1‑bath apartments
3,012 square feet on a 0.23‑acre lot
Separate garage rented to a long‑term tenant, with a large swing‑up door
Garage includes a small office and an interior bathroom
Three of the four apartments have been updated

Restaurant with Five Apartments

Updated: Jun 23

Restaurant with Five Apartments

380 Main Street, Winchester, CT 06098

$999,000

6,200 sqft 0.17 AC lot

6,200 SF restaurant property on 0.17 acres
Dining room seats up to 156 guests
Upstairs bar with 20‑seat capacity
Five apartments; three functioning units and two ready for completion
12‑15 car parking lot plus ample street parking

Two-Unit Duplex

Two-Unit Duplex

48 Center Street, Winchester, CT 06098

$325,000

2,257 sqft 0.08 AC lot

Two rented residences offer a straightforward multifamily configuration in a downtown setting.

Realmo Analytics Monitor Off-market properties and contact owners who are ready to sell. Many signals applied to make quality leads for you. Get Leads

Turnkey Restaurant with Apartments

Turnkey Restaurant with Apartments

380 Main St, Winchester, CT 06098

$999,000

6,200 sqft

Turnkey restaurant with dining, upstairs bar seating, outdoor dining, and five apartments, plus dedicated parking.

Renovated Two-Unit Duplex

Renovated Two-Unit Duplex

77 Hubbard Street, Winchester, CT 06098

$359,900

2,699 sqft 0.28 AC lot

Two updated residences offer three-bedroom layouts, full baths, and refreshed interior finishes.

Two-Unit Duplex with Separate Utilities

Two-Unit Duplex with Separate Utilities

18 Pratt Street, Winchester, CT 06098

$299,900

2,016 sqft 0.17 AC lot

Two residential units offer distinct kitchens, laundry areas, and flexible occupancy options.

Winsted Multifamily Investment Opportunity

Winsted Multifamily Investment Opportunity

150 Oak Street, Winchester, CT 06098

$549,000

5,233 sqft

Charming 5-unit apartment building in residential neighborhood. Fully rented.

Quadplex with Storage Garage

Quadplex with Storage Garage

99 High Street, Winchester, CT 06098

$575,000

3,012 sqft

A small office with an interior bathroom complements the residential units and garage space.

Two-Unit Duplex with Storage

Two-Unit Duplex with Storage

95 Williams Ave, Winchester, CT 06098

$374,900

2,887 sqft

Two residences offer seven bedrooms, three full baths, and separate attic and basement storage.

Two-Unit Duplex Investment Property

Two-Unit Duplex Investment Property

48 Center Street, Winchester, CT 06098

$325,000

2,257 sqft

Downtown duplex with two leased residences, each offering a practical two-bedroom layout and one full bathroom.

Renovated Duplex

Renovated Duplex

77 Hubbard Street, Winchester, CT 06098

$359,900

2,699 sqft

Each unit offers three bedrooms, a full bath, and refreshed interior finishes.

Duplex with Separate Utilities

Duplex with Separate Utilities

18 Pratt Street, Winchester, CT 06098

$299,900

2,016 sqft

Two-story residential income property with distinct laundry areas, a full basement, and one occupied unit.

Mixed-Use Investment Property For Sale

Mixed-Use Investment Property For Sale

45 Elm St, Winchester, CT 06098

$540,000

0.17 AC lot

Seven-unit brick building with residential and commercial spaces.

Multifamily and Office Space Opportunity

Multifamily and Office Space Opportunity

25 Center Street, Winchester, CT 06098

$359,900

2,754 sqft 0.11 AC lot

Multifamily residential property with office space in central location.

MULTI_FAMILY - Winchester, CT

MULTI_FAMILY - Winchester, CT

77 Hubbard St, Winchester, CT 06098

$299,900

2,699 sqft 0.28 AC lot

Two-family residence with modern updates and income potential.

Mixed-Use Building with 12 Apartments

Mixed-Use Building with 12 Apartments

410-416 Main Street, Winchester, CT 06098

$1,100,000

First-floor commercial space is currently configured as one unit and may be divided.

Based on your search, we've compiled 52 Potential Opportunities for your consideration. Besides 16 Active listings in Winsted, CT, we suggest exploring several alternatives: 4 properties in Nearby Cities, and similar 28 Off-Market properties to explore as potential leads, plus 4 Land Listings that present a potential for development.

Opportunities in Nearby Cities

Here are 4 Similar properties we found in Nearby Locations for your consideration.

Multifamily Property with Solar Panels

Multifamily Property with Solar Panels

164 Red Mountain Ave, Torrington, CT 06790

$279,900

1,426 sqft

Fenced grounds, a detached garage, and unfinished third-floor space add practical utility.

Two-Unit Duplex with Separate Parking

Two-Unit Duplex with Separate Parking

33 Terrace View, Norfolk, CT 06058

$369,000

2,596 sqft 0.82 AC lot

Two residential units offer distinct layouts, a front porch, and designated parking areas for each occupant.

Two-Family Home Near Norfolk Center

Two-Family Home Near Norfolk Center

33 Terrace View, Norfolk, CT 06058

$369,000

2,596 sqft

Two-unit property with income potential, close to Norfolk's heart.

Duplex with Garage Apartment

Duplex with Garage Apartment

Torrington, CT 06790

$380,000

1,895 sqft 0.23 AC lot

Two residences offer separate living areas, with a detached garage serving the upper-level apartment.

Potential Development Sites for Consideration

Can't find the perfect fit? These Land listings present an alternative path: the potential to develop a property for your specific goals.

Important: These AI-suggestions are a starting point, not a guarantee of permitted use. All zoning, permitting, and land use information must be independently verified by you with the appropriate local authorities before making any commitments.

Forested Residential/Recreation Land

Forested Residential/Recreation Land

393 Winchester Road, Winchester, CT 06098

$295,000

51.00 AC lot

51 acres of gently rolling, forested land in RU-1 zoning with a former homesite and intermittent streams.

Barkhamsted Land with Valley Views

Barkhamsted Land with Valley Views

28 Fuller Road, Barkhamsted, CT 06063

$99,000

2.07 AC lot

2.07-acre lot with brook, ready for custom home.

Acreage Land with Multiple Frontages

Acreage Land with Multiple Frontages

Meyer Road, Torrington, CT 06790

$425,000

80.04 AC lot

80-acre parcel with four road frontages, including wooded areas, a pond, and owner-hayed farmland.

Torrington Land Ideal for Development

Torrington Land Ideal for Development

Queens Road, Torrington, CT 06790

$299,900

22.58 AC lot

22.58-acre lot zoned for apartment complexes.

Off-Market Properties in Winsted, CT

Consider similar Off-Market properties in Winsted, CT. You may contact the owners directly to inquire about their potential intentions to sell. To help you make a strong first impression, we can assist by reaching out to these owners with compelling proposals created using our AI tool.

169 Prospect St

APARTMENT HOUSE (UNDER 5 UNITS)

169 Prospect St, Winsted, CT 06098-1956

Estimated value:

$550,000

4,848 sqft 0.56 AC lot

91 Torringford St

APARTMENT HOUSE (UNDER 5 UNITS)

91 Torringford St, Winsted, CT 06098-2000

Estimated value:

$730,000

1.54 AC lot

157 Prospect St

APARTMENT HOUSE (UNDER 5 UNITS)

157 Prospect St, Winsted, CT 06098-1955

Estimated value:

$410,000

0.92 AC lot

69 Pleasant Vly Rd

APARTMENT HOUSE (UNDER 5 UNITS)

69 Pleasant Vly Rd, Barkhamsted, CT 06063-4008

Estimated value:

$2,695,000

5.01 AC lot

217 Main St

APARTMENT HOUSE (UNDER 5 UNITS)

217 Main St, Winsted, CT 06098-1282

Estimated value:

$365,000

2,388 sqft 1.13 AC lot

175 Main St

APARTMENT HOUSE (UNDER 5 UNITS)

175 Main St, Winsted, CT 06098-1227

Estimated value:

$355,000

3,823 sqft 0.91 AC lot

7 Chestnut St

APARTMENT HOUSE (UNDER 5 UNITS)

7 Chestnut St, Winsted, CT 06098-1604

Estimated value:

$210,000

3,172 sqft 0.10 AC lot

149 Mdw St, Unit 155

APARTMENT HOUSE (UNDER 5 UNITS)

149 Mdw St, Winsted, CT 06098-1015

Unit 155

Estimated value:

$385,000

4,798 sqft 0.50 AC lot

Winsted, CT Residential Income Properties Market Trends and Statistics

Explore 44 residential income properties for sale in Winsted, CT, showcased through 16 active listings on our real estate platform. These investment opportunities span a total of 45,941 square feet of properties for sale, with an estimated market value of $8,341,300.

Sale prices for residential investment properties in Winsted, CT start at $299,900, averaging $521,331, and reaching up to $1,100,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you stay ahead with the latest data and market trends.

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Top Commercial Asset Segments

Commercial property segments ranked by active listings on the market

Demographics Overview

Population 13K

Population Growth (5Y) -7.4%

Median Household Income $82,614

College Educated 57.2%

Taxes & Financing

Tax Rate (average for all types) 2.65%

Property Tax per SF $43.14 per SF

Average Loan-to-Value 65.0%

Listings Trend

New vs delisted commercial listings in Litchfield County

New Delisted

Total CRE Inventory on Market (SF)

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