Vintage homes for sale & real estate in Jefferson County, KY

Vintage Home for sale in Jefferson County, KY:

Welcome to this freshly remodeled brick ranch in the heart of Ashby Acres! This cozy 3-bedroom, 1-bath home has been thoughtfully updated for easy, low-maintenance living. The kitchen features a warm butcher block countertop, new gas stove, and a comfortable flow into the dining and living areas. Enjoy morning coffee on the covered front porch and unwind in the spacious backyard with a detached garage and a handy lean-to for extra storage or hobbies. A large built-in storage closet at the back of the home adds even more functionality. With one-level living, a level lot, and updates already done for you—this home blends comfort, simplicity, and value in one great package.

Vintage Home for sale in Jefferson County, KY:

Discover a rare park-side opportunity in the heart of the Highlands. Located on a corner site steps from Cherokee Park, this listing spans two parcels and offers two buildings, five units, and a garage in total. Fully vacant and ready for its next chapter, this property is ideal for investors seeking strong rental potential or for someone looking to renovate and restore it into a remarkable single-family home. With its prime location, historic charm, and unmatched flexibility, this one-of-a-kind property presents endless possibilities in one of Louisville's most desirable neighborhoods. Sold as package only with 1706 Cowling, immediately behind property. Cowling Apartment is 384 sqft.

Vintage Home for sale in Jefferson County, KY:

The year-long renovation is nearing completion on this incredible brick painted lady in the Original Highlands. A brand new 2 bedroom, 2 bathroom 1000+ sf carriage house (not included in listing square footage) sits atop a 3-car garage with plenty of room for the owner and tenant to park. Separate meters allow tenants to pay their own electric and the rent will make a huge dent in a monthly mortgage payment. The main house is simply astounding. Enter this picturesque home through the large foyer. On your right is a grand living room that can be closed off with beautiful doors to make a private guest space or office. You will next notice the incredible woodwork indicative of turn of the cent

Vintage Home for sale in Jefferson County, KY:

1425 Debarr St, Louisville, KY - Versatile Highlands Gem with Multigenerational Appeal Nestled in the heart of Louisville's iconic Highlands neighborhood, this stunning 3-story property at 1425 Debarr St offers incredible flexibility for modern living. Perfectly suited for multigenerational or multi-occupant owners, or as a lucrative income-producing duplex, it's currently configured and fully furnished for successful short-term rentals with guests in place. Short-term tenants can vacate quickly if you'd prefer to make it your own personal residence. Just moments from the bustling Bardstown Road corridor—Louisville's original ''Restaurant Row''—you're steps away from eclectic b