Winchester Homes with Paved Parking Features

Winchester Homes with Paved Parking Features

Welcome to Winchester, Kentucky – a charming city that beautifully blends history with modern living. Nestled in Clark County, Winchester is known for its rich heritage and vibrant community spirit. With its picturesque landscapes and friendly neighborhoods, it’s no wonder that many are choosing to call this delightful city home.

Winchester boasts a variety of amenities, including local shops, restaurants, and parks that cater to all ages. The area is steeped in history, with numerous historic sites and landmarks that tell the story of its past. The city is also conveniently located, providing easy access to larger urban centers while maintaining a peaceful, small-town atmosphere.

One of the standout features of homes in Winchester is the availability of properties with paved parking. This practical feature adds both convenience and aesthetic appeal, making it easier for residents to park their vehicles securely and accessibly. Whether you’re hosting friends or simply coming home after a long day, having paved parking ensures that your experience is hassle-free.

The housing market in Winchester offers a diverse range of options, from charming historic homes to modern new builds, all equipped with the comforts of paved parking. This thoughtful addition not only enhances the overall value of the property but also contributes to a well-maintained neighborhood aesthetic.

If you're looking for a welcoming community with beautiful homes and the convenience of paved parking, Winchester, KY is the perfect place to start your next chapter. Embrace the charm of this lovely city and discover the ideal home that meets all your needs!

Newest Winchester Homes with Paved Parking Features

$270,000
6 Beds ⋅ 4 Baths ⋅ 26019498 MLS
Outstanding opportunity for investors or owner-occupants! This beautifully updated duplex is located in Winchester's desirable Stuarts Addition and offers two spacious units, each featuring approximately 1,545 square feet with 3 bedrooms and 2 full bathrooms. Both units have been thoughtfully renovated and feature hardwood flooring throughout the main living areas with tile in the wet areas for style and durability. Major improvements include newer HVAC systems, roof, stainless steel appliances, windows, doors, vinyl siding, and fresh interior paint, providing true move-in-ready convenience and low-maintenance ownership. Ideally located within walking distance of College Park and historic downtown Winchester, this property also offers quick access to I-64, shopping, restaurants, schools, and everyday amenities. Whether you're looking to expand your investment portfolio or live in one unit while generating rental income from the other, this well-maintained duplex offers the perfect combination of modern updates, strong income potential, and an exceptional location.

21 Beckner St, Winchester
$374,000
25508602 MLS
Turn Key Ready! This well established business is equipped and ready for someone to live out their dream. All equipment stays. Two pool tables, barstools, tables, televisions, pool sticks, dartboard, and all inventory stays. HVAC unit, walk in compressors, and cooler recently replaced. Great location in historic downtown Winchester. One of the very few liquor stores in Kentucky that can serve mixed drinks and open liquor. The business has a very well established clientele. Call to schedule a private tour while this one last.

137 E Broadway St, Winchester
$1,950,000
26018115 MLS
Located directly across from the Clark County Hospital this 12,042 office building has been occupied by the Clark County Board of Education since 1969. There is an additional 4,092 sf building located behind the main office that has been finished with office and storage space. This incredible location could be the right site for a multi-tenant renovation, single-use office, or a new beginning.

1600 W Lexington Ave, Winchester
$515,000
26002170 MLS
This versatile mixed-use property offers a rare opportunity to combine business potential with built-in residential income. Formerly operated as a neighborhood market, the commercial building spans over 3,000 square feet and is thoughtfully equipped with a full kitchen and laundry area, making it ideal for a wide range of business concepts. Whether you envision a café, restaurant, retail shop, office space, event venue, service-based business, or creative studio, the layout and infrastructure provide a flexible foundation ready to be reimagined. With strong visibility and a neighborhood presence, this property is well-positioned for an owner-operator or investor seeking adaptability and long-term value. Adding to its appeal is the separate 3-bedroom residential home located at 35 Hays, which is currently income-producing and leased through 2027. This creates an immediate revenue stream while you develop, occupy, or lease the commercial space a powerful advantage for offsetting costs or maximizing returns. Opportunities like this offering commercial flexibility, residential income, and long-term potential are increasingly rare. Whether you're expanding a business, launching something new, or investing with vision, this property delivers the space, structure, and upside to make it happen.

35-37 Hays St, Winchester
$350,000
4 Beds ⋅ 5 Baths ⋅ 26010324 MLS
Investment opportunity in the heart of Winchester! Brick Triplex featuring a main level, high visibility commercial space with Lexington Avenue frontage and two apartments on the upper level! Each apartment has two bedrooms, one bath. One unit has been recently remodeled, the other has potential for value add. The flexible commercial space contains 3 half baths. Laundry hook-ups in all 3 units! Basement for extra storage room with freight elevator. Two new HVAC units and a new roof within the last 2 years! Approximately 16 parking spaces. All 3 units are currently occupied.

502 W Lexington Ave, Winchester
$1,599,900
26012007 MLS
**Click on the Virtual Tour section to see the video walk through!** Prime 20,252 SQFT Industrial Facility -- Exceptional Location & Turnkey Ready This well-maintained 20,000 sqft industrial warehouse offers the ideal combination of location, functionality, and flexibility. Built in 2004, the metal building features a clean, open span layout designed to accommodate a wide range of industrial, storage, logistics, or manufacturing uses. Strategically positioned 1 minute from I-64, 5 minutes from the Mountain Parkway, and 15 minutes from I-75, this property delivers unmatched regional connectivity and fast access across Central and Eastern Kentucky. Inside, the warehouse includes 2 offices, 2 bathrooms, and a break room (approx. 150 sqft total), with the remaining space wide-open for maximum operational efficiency. Loading and distribution are made easy with 2 dock-height doors and 5 drive-in automatic bay doors, offering excellent flow for semi-trucks, box trucks, and fleet operations. A top-of-the-line industrial racking system--valued at over $40,000--has been professionally installed and will convey with the sale. 16' Tall Racks with 8' between uprights, this system is purchased from Toyota Handling Systems and the racks are bolted to the concrete slab. It may be removed or rearranged to meet the buyer's needs, making this a rare turnkey opportunity for businesses requiring optimized warehouse organization. With its incredible highway access, versatile layout, and significant included infrastructure, this property is perfectly suited for logistics operations, distribution, storage, trades, manufacturing, or an expanding local business seeking high-quality industrial space.

599 Blt Way, Winchester
$699,000
26004697 MLS
Operated for over 20 years as a physician's office this two-story building features a "ready to go" office on the main floor with two large apartments on the second floor with walkup, outside entry. The entire structure is on an unfinished basement perfect for storage and access to the mechanical systems. There is also a detached 3-bay garage for parking and storage as well as an asphalt parking lot with more room for more than 25 vehicles.

218 S Maple St, Winchester
$1,200,000
16 Beds ⋅ 16 Baths ⋅ 26007993 MLS
You won't want to miss adding this income-producing apartment complex to your portfolio. This property is comprised of 16 one-bedroom/one-bathroom apartments with 100% occupancy. Complex is conveniently located in downtown Winchester and only 20 minutes from Lexington via easy highway access. The building sits on a 0.34 acre lot with 20+ parking spaces. Property has several updates including roof replacement in 2022, new siding in 2023, and 6 of the AC units were replaced in the last three years. The main electrical service mast was replaced in 2023, and all 100-amp breakers were replaced in 2025. Most units have been updated with LVP flooring.

16 Linden Ave, Winchester
$825,000
26015570 MLS
308 West Lexington has been renovated recently as an office space for a medical practice. The main space consists of a bright reception area, large office, file room, 5 exam rooms and kitchen area. The back of the building has two suites that could be leased out separately or incorporated into the main space. The basement area is unfinished but could be up-fitted for additional office space. The parking lot is generous in size and has access to a back alley way. This property could also be leased. Gateway to the downtown district, close to the Bypass and I-64. Very accessible area. Property Highlights: -Recently renovated -Great location -Multiple Opportunities

308 W Lexington Ave, Winchester
$299,999
25001584 MLS
The building may be old, but everything about it is new! That includes a new roof, 4 new skylights, exposed beams, new hardwood floors throughout, plumbed for 4 bathrooms, laundry room and back office with a window looking into the main space. All of the electrical and plumbing has been done as well. This property boasts the largest back parking lot in the Downtown area making parking for customers and staff a dream. There are numerous grants available as well for this property. Winchester wants your business! 7 new, high-end apartments are going in across the street, there are 5 delicious restaurants on this block, and numerous shops, and the Leeds Center for the Arts is also across the street. Property Highlights: -Recently renovated with a new roof, 4 new skylights, exposed beams, new hardwood floors, new plumbing and new electrical. -Winchester periodically offers numerous building and business grants to kick start your new business. -The property is located directly across from a brand-new apartment building and is surrounded by retail and restaurants. -The property boasts the largest back parking lot in the downtown area

16 N Main St, Winchester
$200,000
26001995 MLS
Business / Investment Opportunity!! 2 commercial units zoned B-3 in the heart of Winchester just off of Lexington Ave. Currently an indoor self storage mini warehouse business with the ability to easily convert to many other options. 10' ceiling height, newer roof, motion sensor lighting, security system, code entry door, parking in front and rear. Units are deeded individually, this listing is for both units (103 & 105 Talbott). 1,404 sq ft each unit, currently no interior dividing wall. Build this business or convert to storefront, salon, larger warehouse space, church, etc.

103 Talbott Ave Unit 2,3, Winchester
$389,900
8 Beds ⋅ 5 Baths ⋅ 26011905 MLS
Here is a chance to own a fully leased fourplex with multiple long term tenants. Located across from a very nice park with plenty of parking. Tenants pay their own utilities. Gross rents are currently $3110/month. Please allow 48 hours to notify tenants for a showing. Showings can be scheduled with proof of funds or a lender pre-approval letter from potential buyers.

23 Wheeler Ave, Winchester
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