Winchester, KY Multifamily Properties for Sale

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12 properties

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Updated: Mar 2

Two-Story Mixed-Use Building

218 S Maple Street, Winchester, KY 40391

$699,000

6,110 sqft 0.70 AC lot

6,110‑square‑foot two‑story mixed‑use building on 0.697 acres
Main level configured as a physician’s office
Two large second‑floor apartments with separate exterior walk‑up access
Unfinished basement for storage and mechanical‑system access
Detached 3‑bay garage plus asphalt parking for more than 25 vehicles

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Updated: Sep 2

3-Unit Triplex with Rear Deck

135 E Broadway Street, Winchester, KY 40391

$350,000

2,592 sqft 0.29 AC lot

Three apartments, all currently rented
2,592‑square‑foot brick triplex on a 0.29‑acre lot
Ground‑floor apartment with living room, kitchen, and bathroom
Two upper apartments, each with a bedroom, living room, kitchen, and bathroom
Large rear deck

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Brick Triplex with Commercial Space

502 W Lexington Avenue, Winchester, KY 40391

$340,000

4,798 sqft 0.18 AC lot

Mixed-use property with Lexington Avenue frontage, two upstairs apartments, and a flexible commercial area on the main level.

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See hot listings in Winchester

Scored against comparables nationwide. These are worth a look.

Cap Rate available after sign in

Est. NOI available after sign in

Local Demand available after sign in

Three-Unit Triplex with Rear Deck

135 E Broadway St, Winchester, KY 40391

$350,000

2,592 sqft

Fully rented residential property with separate living areas, kitchens, bathrooms, and a large rear deck.

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Four-Unit Quadplex

443 Oxford Drive, Winchester, KY 40391

$495,000

1,054 sqft 0.31 AC lot

Four-unit residential income property with two-bedroom, 1.5-bath layouts and R zoning.

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Two-Unit Duplex with Garages

1128-1130 Dale Drive, Winchester, KY 40391

$239,000

2,072 sqft 0.15 AC lot

Side-by-side duplex offering matching layouts, private wooded backyards, and separate one-car garages.

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Three-Unit Property with Carport

221 S Highland Street, Winchester, KY 40391

$239,000

3,007 sqft 0.16 AC lot

Three separately configured residences include kitchens, living areas, laundry space, and rear parking with additional storage.

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16-Unit Apartment Building

16 Linden Ave, Winchester, KY 40391

$1,200,000

7,480 sqft 0.34 AC lot

Fully occupied apartments feature recent exterior, electrical, HVAC, and interior updates.

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Downtown Triplex with Updated Units

130 E Broadway Street, Winchester, KY 40391

$220,000

2,445 sqft 0.17 AC lot

The property combines two refreshed residences with an existing long-term tenancy.

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Quadplex with Similar Layouts

443 Oxford Dr, Winchester, KY 40391

$495,000

1,054 sqft

Comparable floor plans create a consistent configuration across this four-unit residential property.

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Partially Converted Multifamily Building

60 N MAIN ST, Winchester, KY 40391

Contact for pricing

23,296 sqft

Two renovated upper levels provide a substantial start toward apartment conversion, with furniture and finished interiors included.

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148 Acres Planned Development Land

1395 Two Mile Road, Winchester, KY 40391

$1,200,000

148.00 AC lot

148 acres of land zoned for planned development.

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Based on your search, we've compiled 17 Potential Opportunities for your consideration. Besides 12 Active listings in Winchester, KY, we suggest exploring several alternatives: 4 properties in Nearby Cities, plus 1 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.

2023-Built 15-Unit Apartment Building

2007 S Main Street, Paris, KY 40361

$2,890,000

16,950 sqft 0.64 AC lot

Newly constructed multifamily property with uniform two-bedroom layouts and public sewer service.

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15-Unit Apartment Building

2007 S Main St, Paris, KY 40361

$2,890,000

16,950 sqft

Newly constructed multifamily property with uniform two-bedroom, one-bath layouts.

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Remodeled 2-Unit Duplex

412 Woodview Drive A&b, Lexington, KY 40515

$399,000

3,560 sqft

Fully leased duplex with two three-bedroom residences and updated interiors for established rental occupancy.

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Multifamily Property

3532 Brookewind Way, Lexington, KY 40515

$325,000

1,162 sqft

Built in 1996 and marketed within a three-property residential rental portfolio.

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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.

Acre Lot in Country Subdivision

23-23 Outlook Dr, Owingsville, KY 40360

Contact for pricing

1.00 AC lot

Acre lot suitable for residential use, mobile homes allowed.

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Winchester, KY Multifamily Properties Market Trends and Statistics

Explore 12 multifamily properties for sale in Winchester, KY, showcased through 12 active listings on our real estate platform. These investment opportunities span a total of 56,500 square feet of properties for sale, with an estimated market value of $5,827,000.

Sale prices for multifamily properties in Winchester, KY start at $220,000, averaging $529,727, and reaching up to $1,200,000 — 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 37K

Population Growth (5Y) +3.5%

Median Household Income $67,910

College Educated 15.1%

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
40391	$523.5K

Taxes & Financing

Tax Rate (average for all types) 0.91%

Property Tax per SF $10.57 per SF

Average Loan-to-Value 65.0%

Listings Trend

New vs delisted commercial listings in Clark County

New Delisted

Total CRE Inventory on Market (SF)

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