Winchester, KY Office Properties & Spaces for sale

Historical Landmark Multifamily and Office

$1,595,000

26,124 SF

Historical Landmark Multifamily and Office

2 N Main St, Winchester, KY 40391

Turn-key, stabilized investment property in thriving downtown Winchester.

Significant CAPEX investments in 2022 & 2024, including facade transformation and full restoration.
Currently grossing $168,000 annual rent with a $4,000/month upside, exceeding the 1% rule.
Features 20 income‑producing units: 18 LIHTC apartments and 2 renovated ground‑floor offices.
Located in the Kerr Building, the largest downtown historical landmark, with structural repairs and new roofing.
Includes additional space at 4‑10 Main Street, offering potential for tenant improvements and increased cash flow.

Updated: Feb 13

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Mixed-Use Property with Residential Income

$515,000

1,440 SF

Mixed-Use Property with Residential Income

35-37 Hays St, Winchester, KY 40391

Versatile commercial space with separate income-producing residential home.

Income‑producing 3‑bedroom residential home leased through 2027 provides immediate revenue.
Versatile 3,000+ sq ft commercial building suitable for various business types (cafe, retail, office, etc.).
Commercial building includes a full kitchen and laundry area.
Mixed‑use property offers both business and residential opportunities.
Strong visibility and established neighborhood presence.

Updated: Feb 11

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Winchester Office Building with Flex Space

$1,650,000

10,136 SF

Winchester Office Building with Flex Space

10,136 SF office building with conversion potential and pole barn.

273 Shoppers Dr, Winchester, KY 40391

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$825,000

7,200 SF

Winchester Office Building - $825,000

7,200 SF Executive Office, Vacant

920 Bypass Rd, Winchester, KY 40391

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$1,750,000

20,548 SF

The Winchester Opera House

Individual retail properties • 20,548 SF

101 Main St, Winchester, KY 40391

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Based on your search, we've compiled 14 Potential Opportunities for your consideration. Besides 5 Active listings in Winchester, KY, we suggest exploring several alternatives: 4 properties in Nearby Cities, and similar 3 Off-Market properties to explore as potential leads, plus 2 Land Listings that present a potential for development.

Explore Opportunities in Nearby Cities

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

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Hamburg Area Office Condo Available

Office suite for lease in historic Hamburg Place.

1795 Alysheba Way, Lexington, KY 40509

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Contact for pricing

Class A Office Condo

Turn-key office condo in Lexington's Hamburg area.

2704 Old Rosebud Rd, Lexington, KY 40509

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$105,000

1,472 SF

Professional Office Suite For Sale

Commercial office suite suitable for medical or other businesses.

250 Foxglove Dr, Mt Sterling, KY 40353

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Downtown Mt Sterling Commercial Property

$282,500

2,156 SF

Downtown Mt Sterling Commercial Property

Commercial property with reliable income and expansion potential in Mt Sterling.

10-12 Court St, Mt Sterling, KY 40353

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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.

$775,000

3.00 Acres

Winchester Land For Sale

Prime land opportunity in Winchester, Kentucky, near major retailers.

609 Bullion Blvd, Winchester, KY 40391

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$775,000

2.60 Acres

Winchester Land Near Bypass Road

Land available in Winchester, Kentucky, near Kroger and Walmart.

529 Bullion Blvd, Winchester, KY 40391

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Explore Off-Market Properties in Winchester, KY

Consider similar Off-Market properties in Winchester, KY. 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.

10 Court St

Office space • 1,800 SF

Value Estimation by Request

10 Court St, Winchester, KY 40391

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175 Hospital Dr

PROFESSIONAL BUILDING • 45,000 SF

Value Estimation by Request

175 Hospital Dr, Winchester, KY 40391-9591

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1129 Lexington Ave

OFFICE BUILDING • 2,310 SF

Value Estimation by Request

1129 Lexington Ave, Winchester, KY 40391-1134

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Winchester, KY Office Properties & Spaces Investment Opportunities Market Analysis

Explore 8 office properties & spaces for sale in Winchester, KY, showcased through 5 active listings on our real estate platform. These investment opportunities span a total of 70,132 square feet of properties for sale, with an estimated market value of $6,335,000.

Sale prices for office spaces in Winchester, KY start at $515,000, averaging $1,267,000, and reaching up to $1,750,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you stay ahead with the latest data and market trends.

Winchester, KY Office Properties & Spaces for Sale

Historical Landmark Multifamily and Office

Turn-key, stabilized investment property in thriving downtown Winchester.

Mixed-Use Property with Residential Income

Versatile commercial space with separate income-producing residential home.