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Winchester, CT Apartment Buildings for Sale

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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: Jun 28
Turnkey Restaurant with Apartments

380 Main St, 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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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.

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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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Based on your search, we've compiled 8 Potential Opportunities for your consideration. Besides 4 Active listings in Winchester, CT, we suggest exploring several alternatives: 4 properties in Nearby Cities

Opportunities in Nearby Cities

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

Updated 5-Unit Apartment Building
Updated 5-Unit Apartment Building

243 North Elm St, Torrington, CT 06790

$975,000
5,755 sqft

Five-unit multifamily property with separate utilities, tenant laundry, storage, and a dedicated parking lot.

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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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Bristol Multifamily Investment Opportunity
Bristol Multifamily Investment Opportunity

444 West St, Bristol, CT 06010

$350,000
4,860 sqft 0.30 AC lot

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

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Mixed-Use Building Assemblage
Mixed-Use Building Assemblage

45-81 North Main St, Bristol, CT 48043

Contact for pricing
42,000 sqft

Three-building assemblage combining retail and residential uses, with on-site paved parking, city water/sewer, and central HVAC.

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Winchester, CT Apartment Buildings Market Trends and Statistics

Explore 4 apartment buildings for sale in Winchester, CT, showcased through 4 active listings on our real estate platform. These investment opportunities span a total of 17,633 square feet of properties for sale, with an estimated market value of $3,087,000.

Sale prices for two-family homes in Winchester, CT start at $540,000, averaging $771,750, 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 14K
Population Growth (5Y) -2.6%
Median Household Income $85,212
College Educated 77.5%

High-Yield Neighborhoods for Investment

Identify Winchester submarkets with the highest inventory density on the market and evaluate the average listing prices of real estate assets

Neighborhood Average Price
Winsted - 06098 $733.2K

Listings Trend

New vs delisted commercial listings in Litchfield County

New Delisted

Total CRE Inventory on Market (SF)

Average Property Price per SF

For-sale pricing trends across core commercial property types in Litchfield County

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