Winsted, CT Residential Income Properties for Sale

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Victorian Two-Family Home, Winchester CT

$399,000

2,779 SF

Victorian Two-Family Home, Winchester CT

217 Walnut Street, Winchester, CT 06098

Well-maintained Victorian two-family home in a prime location.

Prime in‑town location close to shopping, dining, schools, and major routes.
Two‑family home in exceptional condition with updated kitchens and bathrooms.
Versatile property suitable for investors, owner‑occupants, or multi‑generational living.
Each unit has a private entrance; one unit has 2 bedrooms, the other has 3 bedrooms, both with 1.5 baths.
Features a wrap‑around covered porch, detached 2‑car garage, and additional shed.

Updated: Apr 29

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$579,000

Winsted Multifamily Investment Opportunity

150 Oak St, Winchester, CT 6098

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

Fully rented 5‑family apartment home in a desirable residential neighborhood.
Recent major upgrades including new roof, 4 hot water heaters, and 3 furnaces (2021‑2023).
Features original 1920's charm with original woodwork, high ceilings, and some hardwood floors.
Includes a 4‑bay detached garage, with rental income potential.
Convenient location: walking distance to Northwestern CT Community College and Downtown Winsted.

Updated: Apr 21

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$475,000

Well-Maintained Three-Family Home

Rare, well-maintained three-family home with market rents.

51 Hinsdale Ave, Winchester, CT 6098

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$299,900

2,699 SF

Updated Two-Family Winchester Residence

Two-family residence with modern updates and income potential.

77 Hubbard Street, Winchester, CT 06098

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Mixed-Use Building with Income Potential

$540,000

7,405 SF

Mixed-Use Building with Income Potential

Seven-unit brick building with residential and commercial spaces for sale.

45 Elm Street, Winchester, CT 6098

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$750,000

5,389 SF

Restaurant and Apartments in Winchester

Turnkey restaurant with apartments in high-traffic Litchfield County location.

436 Main Street, Winchester, CT 6098

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Multifamily and Office Space Opportunity

$359,900

2,754 SF

Multifamily and Office Space Opportunity

Multifamily residential property with office space in central location.

25 Center Street, Winchester, CT 6098

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$395,000

1,909 SF

Downtown Winsted Mixed-Use Building

Two-story building with commercial space and renovated apartment.

720 Main Street, Winchester, CT 6098

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$750,000

5,389 SF

Restaurant and Apartments in Winchester

Turnkey restaurant with apartments in high-traffic Litchfield County location.

436 Main Street, Winchester, CT 6098

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Based on your search, we've compiled 45 Potential Opportunities for your consideration. Besides 9 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.

$559,000

2,699 SF

Main Street Mixed-Use Investment

Fully occupied mixed-use property with strong income and recent renovations.

433 Main Street, New Hartford, CT 6061

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$224,900

North End Two-Family Home

Two-family home in North End neighborhood with detached garage.

60 Benham St, Torrington, CT 6790

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$224,900

1,632 SF

North End Two-Family Home

Two-family home in North End neighborhood with detached garage.

60 Benham Street, Torrington, CT 6790

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$349,900

2,248 SF

Downtown Office Building For Sale

Well-maintained office building with potential for mixed-use or residential conversion.

7 Church Street North, New Hartford, CT 6057

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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.

$299,900

63.00 Acres

63 Acres Abutting State Forest

63-acre wooded land parcel abutting Algonquin State Forest.

32 Norfolk Road, Winchester, CT 06098

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$295,000

51.00 Acres

Forested Land in Winchester Center

51 acres of gently rolling, forested land in Winchester.

393 Winchester Road, Winchester, CT 06098

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$158,000

1.18 Acres

Winchester Land with Waterfront Access

1.18 acre Winchester lot with potential for dream home.

843-845 (lots - 10A,10 &1 E wakefield Boulevard, Winchester, CT 06098

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$59,900

0.41 Acres

Winchester Land Near Highland Lake

Contiguous parcels near Highland Lake with potential city sewer access.

105,107 Mountain Road, Winchester, CT 06098

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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) • 4,848 SF

Value Estimation

$550,000

169 Prospect St, Winsted, CT 06098-1956

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91 Torringford St

APARTMENT HOUSE (UNDER 5 UNITS) • 1.54 Acres

Value Estimation

$670,000

91 Torringford St, Winsted, CT 06098-2000

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157 Prospect St

APARTMENT HOUSE (UNDER 5 UNITS) • 0.92 Acres

Value Estimation by Request

157 Prospect St, Winsted, CT 06098-1955

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69 Pleasant Vly Rd

APARTMENT HOUSE (UNDER 5 UNITS) • 5.01 Acres

Value Estimation

$2,450,000

69 Pleasant Vly Rd, Barkhamsted, CT 06063-4008

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217 Main St

APARTMENT HOUSE (UNDER 5 UNITS) • 2,388 SF

Value Estimation by Request

217 Main St, Winsted, CT 06098-1282

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175 Main St

APARTMENT HOUSE (UNDER 5 UNITS) • 3,823 SF

Value Estimation by Request

175 Main St, Winsted, CT 06098-1227

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7 Chestnut St

APARTMENT HOUSE (UNDER 5 UNITS) • 3,172 SF

Value Estimation by Request

7 Chestnut St, Winsted, CT 06098-1604

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149 Mdw St, Unit 155

APARTMENT HOUSE (UNDER 5 UNITS) • 4,798 SF

Value Estimation by Request

149 Mdw St, Winsted, CT 06098-1015

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6 Brk St

APARTMENT HOUSE (UNDER 5 UNITS) • 3,400 SF

Value Estimation by Request

6 Brk St, Winsted, CT 06098

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14 Wheeler St

APARTMENT HOUSE (UNDER 5 UNITS) • 3,043 SF

Value Estimation by Request

14 Wheeler St, Winsted, CT 06098-1568

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12 Gay St

APARTMENT HOUSE (UNDER 5 UNITS) • 2,750 SF

Value Estimation by Request

12 Gay St, Winsted, CT 06098-1609

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61 Holabird Ave

APARTMENT HOUSE (UNDER 5 UNITS) • 3,675 SF

Value Estimation by Request

61 Holabird Ave, Winsted, CT 06098-1692

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106 Elm St, Unit 112

APARTMENT HOUSE (UNDER 5 UNITS) • 2,712 SF

Value Estimation by Request

106 Elm St, Winsted, CT 06098-1637

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143 Main St

APARTMENT HOUSE (UNDER 5 UNITS) • 2,756 SF

Value Estimation by Request

143 Main St, Winsted, CT 06098-1281

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13 Greenwoods Ave

APARTMENT HOUSE (UNDER 5 UNITS) • 3,600 SF

Value Estimation by Request

13 Greenwoods Ave, Winsted, CT 06098-3001

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Winsted, CT Residential Income Properties Investment Opportunities Market Analysis

Explore 37 residential income properties for sale in Winsted, CT, showcased through 9 active listings on our real estate platform. These investment opportunities span a total of 28,324 square feet of properties for sale, with an estimated market value of $3,493,800.

Sale prices for residential income properties in Winsted, CT start at $299,900, averaging $499,114, and reaching up to $750,000 — 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

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 sq ft

Average Loan-to-Value 65.0%

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Winsted, CT Residential Income Properties for Sale

Victorian Two-Family Home, Winchester CT

Well-maintained Victorian two-family home in a prime location.

Winsted Multifamily Investment Opportunity

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

Well-Maintained Three-Family Home

Updated Two-Family Winchester Residence

Mixed-Use Building with Income Potential

Restaurant and Apartments in Winchester

Multifamily and Office Space Opportunity

Downtown Winsted Mixed-Use Building

Restaurant and Apartments in Winchester

Opportunities in Nearby Cities

Main Street Mixed-Use Investment

North End Two-Family Home

North End Two-Family Home

Downtown Office Building For Sale

Potential Development Sites for Consideration

63 Acres Abutting State Forest

Forested Land in Winchester Center

Winchester Land with Waterfront Access

Winchester Land Near Highland Lake

Off-Market Properties in Winsted, CT

169 Prospect St

91 Torringford St

157 Prospect St

69 Pleasant Vly Rd

217 Main St

175 Main St

7 Chestnut St

149 Mdw St, Unit 155

6 Brk St

14 Wheeler St

12 Gay St

61 Holabird Ave

106 Elm St, Unit 112

143 Main St

13 Greenwoods Ave

Winsted, CT Residential Income Properties Investment Opportunities Market Analysis

Top Commercial Asset Segments

Demographics Overview

Taxes & Financing

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