Winchester Homes with On Site Parking Features

Winchester Homes with On Site Parking Features

Welcome to Winchester, Kentucky – a charming city nestled in the heart of Clark County, where southern hospitality meets vibrant community living. With its rich history, picturesque landscapes, and a welcoming atmosphere, Winchester is an ideal place for families, young professionals, and retirees alike. Known for its historic downtown area, Winchester boasts beautifully preserved architecture, delightful local shops, and a variety of dining options that cater to every palate.

One of the standout features of homes in Winchester is the abundance of properties equipped with on-site parking. In a city where convenience and accessibility are paramount, having dedicated parking spaces can significantly enhance your living experience. Whether you’re returning from a day of exploring the scenic parks or enjoying the local arts and culture scene, knowing that your vehicle is safely parked just steps from your front door adds a layer of comfort to your daily routine.

Winchester is also home to several community events and festivals throughout the year, fostering a strong sense of community and connection among residents. With easy access to major highways and nearby cities, Winchester serves as a perfect base for those who want to enjoy both the tranquility of small-town living and the excitement of urban amenities.

If you’re considering a move to this delightful city, you’ll find a variety of homes that not only offer on-site parking but also embody the warmth and charm that Winchester is known for. Come discover the perfect blend of comfort, convenience, and community in Winchester, Kentucky!

Newest Winchester Homes with On Site Parking Features

$499,000
26023469 MLS
Very unique commercial property located in the heart of downtown Winchester! This versatile property consists of two separate buildings, a large private parking lot, and convenient rear alley access, offering numerous possibilities for an owner-user or investor. The front building has been nicely up-fitted and is currently configured as professional office space. However, the building's original character and functionality remain hidden above the drop ceiling, including tall ceilings and exposed metal trusses. Previously used as warehouse space, the building once featured a dock door for deliveries, making it a great candidate for conversion back to warehouse, showroom, flex, or mixed office/warehouse use. The rear building features a concrete floor, tall ceilings, and excellent potential. It is currently divided into two separate warehouse spaces, providing flexibility for multiple tenants, storage, business operations, or future redevelopment. With two buildings, ample on-site parking, alley access, and flexible commercial space, this downtown Winchester property offers a unique opportunity with a variety of potential uses. Property Highlights: -Large warehouse space in convenient location -Professional office space -Buyers could parcel this property separately -Adjacent to Downtown Winchester, ample retail, and high-density residential

26 N Highland St, Winchester
$450,000
26022173 MLS
Prime commercial opportunity in an ideally located area of Winchester! This versatile commercial building offers an excellent location for an established business, growing company, or investor seeking a property with strong potential. Conveniently situated with easy access to major roadways and surrounding communities, the property provides excellent visibility and accessibility for customers and clients. The building offers flexible space that can be adapted to a variety of business uses. Whether you're looking to establish your business, expand your operations, or add to your investment portfolio, 1320 Fulton Road presents an outstanding opportunity in a desirable Winchester location. Don't miss the chance to make this well-positioned commercial property your next business venture or investment!

1320 Fulton Rd, Winchester
$495,000
2 Beds ⋅ 2 Baths ⋅ 26019713 MLS
Don't miss this rare quadruplex opportunity in Winchester. Featuring four units (443, 445,447 and 449 Oxford Drive), this property is perfect for investors seeking multiple income streams in one location. Each unit offers a similar layout with approximately 1,054 ft, 2 bedrooms, and 1.5 baths. The photos shown are from one updated unit, and all units have comparable layouts—making this an ideal setup for consistent rental demand. The vacant property (449) can be viewed through scheduling via showing time and sentrikey box is on the back door, the other 3 units are occupied and can be viewed with 48 hours notice given to the tenants.

443 Oxford Unit 443,445,447,449, 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
$340,000
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.

502 W Lexington Ave, 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
An excellent opportunity to own a fully leased, income-producing property in the heart of Downtown Winchester, Kentucky. This beautifully renovated 2,310 SF retail storefront is being offered at a 10% cap rate, making it an attractive turnkey investment from day one. The building may be old, but nearly everything inside is new! Recent improvements include a new roof, four new skylights, exposed beams, new hardwood flooring throughout, updated electrical and plumbing, and HVAC. The space is plumbed for four bathrooms and also includes a laundry room and private back office with a window overlooking the main retail area. This property boasts a large rear parking lot—one of the largest in Downtown Winchester—providing convenient parking for tenants, customers, and employees. The location is surrounded by continued downtown growth. Seven new high-end apartments across the street, while the same block is already home to five restaurants, numerous shops, and the Leeds Center for the Arts. Property Highlights: -Recently renovated with a new roof, 4 new skylights, exposed beams, new hardwood floors, new plumbing and new electrical. -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, a bonus for staff and customer accessibility. -Downtown Winchester, KY is booming - everyone wants to be Downtown, introducing shops, restaurants, and new apartment living options. Winchester, KY is conveniently situated just 18 miles east of Lexington and, with proximity to I-64, provides quick access to the larger city's amenities. Downtown Winchester is home to a variety of beloved local establishments, including the historic Leeds Center for the Arts, La Trattoria, The Hall Coffee & Social Club, and several small shops. Over 30 new, high-end apartments are coming to Downtown Winchester - residents and tourists want to be Downtown!

16 N Main St, Winchester
$250,000
26013923 MLS
Exciting opportunity for congregations, investors, or visionaries seeking a one-of-a-kind property! This spacious one-level property offers over 2,500 sq ft with 2 bathrooms, a roof that is approximately 6 years old, and endless possibilities for renovation or repurposing. Situated on a quiet street, this unique space provides the perfect canvas to bring your vision to life. Property is being sold as-is. Buyers to verify square footage and lot size.

3150 Waterworks Rd, Winchester
$239,000
4 Beds ⋅ 4 Baths ⋅ 26000922 MLS
Duplex. Both units are being sold together. Great income-producing potential. Each side offers a nice sized vaulted Great room that opens to the kitchen, 2 bedrooms, 1.5 baths, a laundry room, and a 1-car garage. Nice private backyard for side with lots of trees. 1130 has a new HVAC. Selling As Is Inspections Welcome.

1128-1130 Dale Dr, Winchester
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