Winchester Homes with On Site Parking Features

Winchester Homes with On Site Parking Features

Welcome to Winchester, Kentucky—a charming city nestled in Clark County, where Southern hospitality meets rich history and vibrant community life. Known for its scenic beauty and small-town charm, Winchester offers a perfect blend of modern amenities and historical significance. With a population that embraces its heritage, this city is a delightful place to call home.

Winchester is steeped in history, with its roots tracing back to the 18th century. The city boasts a variety of architectural styles, from quaint cottages to spacious family homes, each telling a story of its own. Residents enjoy access to excellent schools, beautiful parks, and a range of local shops and restaurants that cater to diverse tastes. The community hosts numerous events throughout the year, fostering a warm and welcoming atmosphere for families and newcomers alike.

When it comes to finding your dream home, Winchester offers a selection of properties equipped with on-site parking features—an essential convenience in today’s busy lifestyle. Imagine coming home after a long day, knowing you have a dedicated space waiting just for you. These homes not only provide the ease of parking but also enhance your overall living experience, allowing you to enjoy the freedom of having your own space.

Whether you’re a first-time homebuyer or looking to settle down in a peaceful environment, Winchester, KY, has something for everyone. Explore the charming neighborhoods and discover the perfect home that fits your lifestyle, complete with the convenience of on-site parking. Welcome to your future in Winchester—where comfort meets community!

Newest Winchester Homes with On Site Parking Features

$389,900
9 Beds ⋅ 6 Baths ⋅ 26020069 MLS
Exceptional investment opportunity! This fully occupied triplex is a turnkey addition to any investment portfolio, offering three spacious units, each with approximately 1,116 square feet, 3 bedrooms, and 1.5 bathrooms. With strong rental potential and separately metered utilities paid by the tenants, this property provides an excellent income-producing opportunity. Each unit features a well-designed two-story floor plan with a welcoming foyer, spacious living room, kitchen, utility area, and half bath on the main level. Upstairs, you'll find three generously sized bedrooms and a full bathroom, creating a comfortable layout that appeals to long-term tenants. Additional features include private decks, ceiling fans, window blinds, ample off-street parking, and generously sized yards. Conveniently maintained and fully leased, this multifamily property offers immediate cash flow with minimal owner responsibilities. Showings are available by appointment only with advance notice to accommodate the tenants.

341-345 Carolina Ave, Winchester
$529,000
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. All 3 units are currently occupied.

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
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
$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
$199,000
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
$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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