Winchester, KY Residential Income Properties for Sale

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Updated: Mar 7

Triplex with Two Updated Units

130 E Broadway Street, Winchester, KY 40391

$235,000

2,445 sqft 0.17 AC lot

Two 1BD/1BA units plus one 2BD/1BA unit
Tenants pay utilities except water on a RUB system
Two units recently updated; third unit has a long‑term tenant
Sold as‑is with tenants already in place
0.17‑acre lot and 2,445 SF total building area

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This listing looks promising.

Here's a quick look at some key insights for

130 E Broadway Street, Winchester, KY 40391

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Est. Cap Rate

8.9%
Above avg (5.9%)
Est. NOI

$21K
Annual
Price @ 7% Cap

$298K
Above asking
Property Type

Single Family Residence
Built 1940

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Updated: Jul 24

Four-Unit Quadplex Opportunity

443 Oxford Drive, Winchester, KY 40391

$529,000

1,054 sqft 0.31 AC lot

Quadruplex with four units at 443, 445, 447 and 449 Oxford Drive in Winchester
Each unit offers approx. 1,054 SF, 2 bedrooms, and 1.5 baths
Year built 1970 with forced air heating and natural gas service
Electric cooling and composition/shingle roof
Unit 449 is vacant; view by scheduling with showing time, sentrikey box on the back door

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Two-Story Office Building with Apartments

218 S Maple Street, Winchester, KY 40391

$699,000

6,110 sqft 0.70 AC lot

Main-floor office space with two upstairs apartments, plus an unfinished basement, detached 3-bay garage, and parking for 25+ vehicles.

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Updated Corner Duplex with Tenants

1 N Main Street, Winchester, KY 40391

$225,000

1,900 sqft 0.02 AC lot

Updated duplex on a highly visible downtown corner with tenants in place on both levels.

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Turn a Listing Into an Investment Snapshot Cap Rate, Potential NOI, Demand score for every listing. Go To Analytics Center

Historic Mixed-Use Rental Building

5 W Broadway St, Winchester, KY 40391

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Historic building built in 1889 with 18 rental units and about 9,000 sq ft of commercial space.

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Residential Income Property with Porch

410 W Lexington Avenue, Winchester, KY 40391

$329,900

4,456 sqft 0.52 AC lot

5-bedroom, 4-bath home with 10-foot ceilings and a front porch, suited for residential income or mixed-use planning.

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Mixed-Use Triplex with Storefront

502 W Lexington Avenue, Winchester, KY 40391

$340,000

4,798 sqft 0.18 AC lot

Brick property offers a street-facing commercial space and two upstairs two-bedroom apartments.

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Ranch Duplex with Attached Garage

408 Colby Ridge Boulevard, Winchester, KY 40391

$207,000

948 sqft 0.12 AC lot

Ranch-style duplex with an attached garage, privacy fencing, and public water and sewer service.

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Mixed-Use Downtown Corner Property

2 N Main St, Winchester, KY 40391

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Mixed-use building with renovated, fully occupied apartments above ground-floor retail space on a downtown corner.

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Updated Duplex with Two Units

21 Beckner Street, Winchester, KY 40391

$270,000

3,090 sqft 0.21 AC lot

Renovated duplex in R-1C zoning featuring two sizable 3-bedroom, 2-bath units with modern interior finishes.

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Two-Unit Duplex For Sale

1128-1130 Dale Drive, Winchester, KY 40391

$239,000

2,072 sqft 0.15 AC lot

Duplex with two paired units, each featuring vaulted great rooms, 2 bedrooms, 1.5 baths, and a 1-car garage.

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Mixed-Use Property with Income Home

35-37 Hays Street, Winchester, KY 40391

$498,000

1,440 sqft 0.13 AC lot

Mixed-use building with a kitchen and laundry area plus a separate 3-bedroom residence leased through 2027.

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Fully Leased Fourplex

23 Wheeler Avenue, Winchester, KY 40391

$389,900

4,687 sqft 0.23 AC lot

Fully leased fourplex with long-term tenants and utilities paid by residents, positioned across from a park with ample parking.

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Triplex With Carport and Storage

221 S Highland Street, Winchester, KY 40391

$239,000

3,007 sqft 0.16 AC lot

Triplex in R-1C zoning with three separate living areas, plus a back parking area, carport, and storage building.

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Based on your search, we've compiled 22 Potential Opportunities for your consideration. Besides 14 Active listings in Winchester, KY, we suggest exploring several alternatives: 4 properties in Nearby Cities, 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.

Wooded Apartment Property

1429 Brush Creek Road, Clay City, KY 40312

$1,400,000

11,378 sqft 32.00 AC lot

Multi-structure property with apartment units, a guest house, office space, and a finished basement.

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Wooded Mixed-Use Property

1429 Brush Creek Road, Clay City, KY 40312

$1,400,000

11,378 sqft 32.00 AC lot

Mixed-use property with apartments, office areas, a guest house, and a finished basement on a wooded site.

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Fully Leased Duplex

412 Woodview Drive, Lexington, KY 40515

$399,000

3,560 sqft 0.26 AC lot

Fully leased duplex zoned R-3 with two 3-bedroom, two-bath units; remodeled in 2021.

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Multifamily Property with Unit Upgrades

305 Lindenhurst Dr, Lexington, KY 40509

Contact for pricing

280-unit apartment community has a mix of classic and upgraded units, with ownership improvements completed since 2018.

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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.

Residential Lot in Winchester, KY

75 4th Street, Winchester, KY 40391

Contact for pricing

0.06 AC lot

0.06-acre residential lot, ideal for new construction or investment.

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Downtown Winchester Land Assemblage

33-41 Winn Avenue, Winchester, KY 40391

$490,000

1.53 AC lot

1.53 acres of vacant land in downtown Winchester, Kentucky.

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Winchester Land Investment Opportunity

1395 Two Mile Road, Winchester, KY 40391

$550,500

20.78 AC lot

20+ acre residential land tract near Winchester Country Club.

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Winchester, KY Land Opportunity

1395 Two Mile Road, Winchester, KY 40391

$1,200,000

24.15 AC lot

24-acre residential land in Winchester, zoned for planned development.

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Winchester, KY Residential Income Properties Market Trends and Statistics

Explore 14 residential income properties for sale in Winchester, KY, showcased through 14 active listings on our real estate platform. These investment opportunities span a total of 36,007 square feet of properties for sale, with an estimated market value of $4,200,800.

Sale prices for residential income properties in Winchester, KY start at $207,000, averaging $350,066, and reaching up to $699,000 — 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	$370.7K

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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