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Winsted, CT Apartment Buildings for Sale

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6 properties
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
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Turnkey Restaurant with Apartments
Updated: May 3
Turnkey Restaurant with Apartments

380 Main Street, Winchester, CT 06098

$999,000
6,200 sqft
Turnkey restaurant operation with seating for up to 156 guests in the main dining area
Upstairs 20‑seat bar for expanded service and private events
Outdoor dining available with seating for approximately 24 guests
Includes five apartments: three currently functioning units and two additional units ready for completion
Basement is equipped for dough preparation and offers abundant storage for catering operations
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Historic 5-Unit Apartment Building
Historic 5-Unit Apartment Building

150 Oak Street, Winchester, CT 06098

$579,000
5,233 sqft

Fully rented 5-family apartment building with a detached 4-bay garage, updated roof and multiple heating systems.

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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.

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Winsted Multifamily Investment Opportunity
Winsted Multifamily Investment Opportunity

150 Oak St, Winchester, CT 06098

$549,000

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

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Mixed-Use Retail and Apartments
Mixed-Use Retail and Apartments

430 Main St, Winchestr Ctr, CT 06098

Contact for pricing
9,508 sqft

First-floor retail features parking and a rear loading dock, with apartments on the second and third floors.

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Based on your search, we've compiled 37 Potential Opportunities for your consideration. Besides 6 Active listings in Winsted, CT, we suggest exploring several alternatives: 4 properties in Nearby Cities, and similar 27 Off-Market properties to explore as potential leads

Opportunities in Nearby Cities

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

Five-Unit Apartment Building
Five-Unit Apartment Building

243 N Elm Street, Torrington, CT 06790

$975,000
5,755 sqft 0.17 AC lot

Updated multifamily property with separate utilities, basement laundry, storage, and dedicated parking area.

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Six-Unit Multifamily Building
Six-Unit Multifamily Building

291 East Main Street, Torrington, CT 06790

$525,000
4,431 sqft

Well-maintained six-unit multifamily property with separate utilities and off-street parking.

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Downtown Mixed-Use Brick Portfolio
Downtown Mixed-Use Brick Portfolio

411-431 North Main Street, Bristol, CT 06010

Contact for pricing
26,300 sqft 0.92 AC lot

Three contiguous brick buildings combine 32 apartments with six ground-floor retail storefronts and off-street tenant parking.

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Bristol Multifamily Investment Opportunity
Bristol Multifamily Investment Opportunity

444 West St, Bristol, CT 06010

Contact for pricing
6,940 sqft 0.30 AC lot

Value-add 7-unit property with income and appreciation potential.

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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)

169 Prospect St, Winsted, CT 06098-1956

$550,000
Estimated value
4,848 sqft 0.56 AC lot
View details
91 Torringford St
APARTMENT HOUSE (UNDER 5 UNITS)

91 Torringford St, Winsted, CT 06098-2000

$730,000
Estimated value
1.54 AC lot
View details
157 Prospect St
APARTMENT HOUSE (UNDER 5 UNITS)

157 Prospect St, Winsted, CT 06098-1955

$410,000
Estimated value
0.92 AC lot
View details
69 Pleasant Vly Rd
APARTMENT HOUSE (UNDER 5 UNITS)

69 Pleasant Vly Rd, Barkhamsted, CT 06063-4008

$2,695,000
Estimated value
5.01 AC lot
View details
217 Main St
APARTMENT HOUSE (UNDER 5 UNITS)

217 Main St, Winsted, CT 06098-1282

$365,000
Estimated value
2,388 sqft 1.13 AC lot
View details
175 Main St
APARTMENT HOUSE (UNDER 5 UNITS)

175 Main St, Winsted, CT 06098-1227

$355,000
Estimated value
3,823 sqft 0.91 AC lot
View details
7 Chestnut St
APARTMENT HOUSE (UNDER 5 UNITS)

7 Chestnut St, Winsted, CT 06098-1604

$210,000
Estimated value
3,172 sqft 0.10 AC lot
View details
149 Mdw St, Unit 155
APARTMENT HOUSE (UNDER 5 UNITS)

149 Mdw St, Winsted, CT 06098-1015

Unit 155
$385,000
Estimated value
4,798 sqft 0.50 AC lot
View details
6 Brk St
APARTMENT HOUSE (UNDER 5 UNITS)

6 Brk St, Winsted, CT 06098

$340,000
Estimated value
3,400 sqft 0.12 AC lot
View details
14 Wheeler St
APARTMENT HOUSE (UNDER 5 UNITS)

14 Wheeler St, Winsted, CT 06098-1568

$315,000
Estimated value
3,043 sqft 0.07 AC lot
View details
12 Gay St
APARTMENT HOUSE (UNDER 5 UNITS)

12 Gay St, Winsted, CT 06098-1609

$190,000
Estimated value
2,750 sqft 0.12 AC lot
View details
61 Holabird Ave
APARTMENT HOUSE (UNDER 5 UNITS)

61 Holabird Ave, Winsted, CT 06098-1692

$105,000
Estimated value
3,675 sqft 0.36 AC lot
View details
106 Elm St, Unit 112
APARTMENT HOUSE (UNDER 5 UNITS)

106 Elm St, Winsted, CT 06098-1637

Unit 112
$305,000
Estimated value
2,712 sqft 0.12 AC lot
View details
143 Main St
APARTMENT HOUSE (UNDER 5 UNITS)

143 Main St, Winsted, CT 06098-1281

$305,000
Estimated value
2,756 sqft 0.37 AC lot
View details
13 Greenwoods Ave
APARTMENT HOUSE (UNDER 5 UNITS)

13 Greenwoods Ave, Winsted, CT 06098-3001

$300,000
Estimated value
3,600 sqft 0.12 AC lot
View details
5 Home Pl
APARTMENT HOUSE (UNDER 5 UNITS)

5 Home Pl, Winsted, CT 06098-1709

$315,000
Estimated value
2,952 sqft 0.95 AC lot
View details
19 Ctr St
APARTMENT HOUSE (UNDER 5 UNITS)

19 Ctr St, Winsted, CT 06098-1611

$280,000
Estimated value
0.18 AC lot
View details
331 Lk St
APARTMENT HOUSE (UNDER 5 UNITS)

331 Lk St, Winsted, CT 06098-1443

$315,000
Estimated value
3,120 sqft 0.35 AC lot
View details

Winsted, CT Apartment Buildings Market Trends and Statistics

Explore 33 apartment buildings for sale in Winsted, CT, showcased through 6 active listings on our real estate platform. These investment opportunities span a total of 27,141 square feet of properties for sale, with an estimated market value of $3,666,000.

Sale prices for two-family homes in Winsted, CT start at $540,000, averaging $733,200, and reaching up to $999,000 — 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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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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