Winchester, KY Residential income properties for sale

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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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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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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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

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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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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Mixed-Use Property with Income Home

35-37 Hays Street, Winchester, KY 40391

$435,000

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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Realmo Analytics Monitor Off-market properties and contact owners who are ready to sell. Many signals applied to make quality leads for you. Get Leads

Renovated Retail Storefront

16 N Main Street, Winchester, KY 40391

$299,999

2,310 sqft 0.18 AC lot

Fully leased retail space with updated building systems, customer parking, and a private rear office.

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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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Land, Winchester, KY

2323 Crowe Ridge Road, Winchester, KY 40391

$120,000

1.64 AC lot

Residential land & home lots · 1.64 Acres

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9 active listings match your search: Residential Income for sale in Winchester, KY. Based on your search, we've also compiled 8 Potential Opportunities for your consideration: 4 properties in nearby cities and 4 land listings with development potential.

Opportunities in Nearby Cities

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

Ranch-Style Residential Property

617 Durning Rd, Lexington, KY 40509

$510,000

1,906 sqft

Single-level living includes a private garage, updated interior finishes, and access to community recreation amenities.

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Triplex with Updated HVAC

119 Fifth Avenue, Clay City, KY 40312

$360,000

2,784 sqft 0.15 AC lot

Three-unit multifamily property with central air, forced-air heat, and blacktop tenant parking.

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Three-Unit Triplex

119 Fifth Avenue #ABC, Clay City, KY 40312

$360,000

2,784 sqft

Two residences are leased, while the third is available for showings.

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Land, Lexington, KY

3703 Winchester Road lot: 2D, 2E, And 2F, Lexington, KY 40509

$385,000

2.12 AC lot

Residential land & home lots · 2.12 Acres

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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.

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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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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Winchester Land Development Opportunity

155 Spring Ridge Way, Winchester, KY 40391

$188,500

12.10 AC lot

12+ acres for development in Winchester, Kentucky.

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Winchester, KY Land For Sale

270 Duclair Drive, Winchester, KY 40391

$100,000

1.10 AC lot

Residential land for upscale home in Central Kentucky.

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Winchester, KY Residential Income Properties Market Trends and Statistics

Explore 9 residential income properties for sale in Winchester, KY, showcased through 9 active listings on our real estate platform. These investment opportunities span a total of 38,874 square feet of properties for sale, with an estimated market value of $3,837,999.

Sale prices for residential investment properties in Winchester, KY start at $120,000, averaging $479,749, 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.

Neighborhood	Average Price
40391	$511.5K

Neighborhood

Average Price

40391

$511.5K

Featured Winchester Real Estate Agencies

Realmo connects you with licensed Winchester CRE brokers providing property specifications, local market pricing, and commercial transaction underwriting support.

Steven D Adams Real Estate Services, LLC

12 Court St, Ste #1 Winchester, KY

Phone: (859) 744-1080

www.kyappraisals.com/

HomeFirst Real Estate

27 Wheeler Ave Winchester, KY

Phone: (859) 749-7400