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$335,000

Some houses have a little more personality than others. 108 First Street is one of them. Start your morning on the front porch with a cup of coffee and the sounds of Simpsonville waking up around you. Church bells across the street, a short walk to the farmers market, and Simpsonville Park just down the road give this home a location that is hard to duplicate. Inside, the character continues. This well-maintained older home has the details you hope to find, including beautiful original trim, solid-core doors, and a story-and-a-half layout that gives the home plenty of personality without sacrificing function. The kitchen has been renovated, the laundry is conveniently located on the main floor, and there are three bedrooms and two full bathrooms spread across approximately 1,788 square feet. The roughly .3-acre lot gives you just enough room to enjoy the outdoors without spending your weekends maintaining a huge yard. Garden, entertain, let the kids play, or simply sit on the porch and watch the neighborhood go by. And then there's the location. You're right in the heart of old-town Simpsonville, close enough to walk to some of the town's favorite spots while still being only minutes from I-64. If you like homes with character, a little history, and a location that lets you actually enjoy small-town living, 108 First Street deserves a look.

3 Beds ⋅ 2 Baths ⋅ 1729967 MLS

108 1st St, Simpsonville

$985,000

This 4-bedroom, 2-bath historic farmhouse is situated on 5 scenic acres (with an additional adjoining 5-acre tract available for purchase and possible owner financing) in the heart of Simpsonville and offers a rare combination of residential comfort, equestrian functionality, income potential, and Kentucky character. The property includes two barns, seven fenced paddocks, a pond, a detached garage with a finished apartment, and picturesque views across the surrounding countryside. Built in 1938, the farmhouse blends timeless charm with thoughtful modern updates. Rich hardwood floors, elegant crown molding, two fireplaces, and an abundance of natural light create a warm and inviting atmosphere throughout the home. Large windows capture sweeping views of the pastures, pond, rolling landscape, and memorable Kentucky sunsets. The spacious kitchen offers stainless steel appliances, a beautiful bay window, generous workspace, and an open layout designed for both everyday living and entertaining. A classic front porch provides the perfect place to enjoy peaceful mornings, while the expansive screened-in covered rear deck overlooks the property and creates an ideal setting for relaxing, dining, or hosting guests. Designed with equestrian use in mind, the 13-stall main barn features 12-by-12 stalls, built-in hay racks, wide aisles, a dedicated wash area, and a well-appointed tack room. The farm also includes seven fenced paddocks with run-in sheds and automatic waterers, creating an efficient and functional setup for horses and livestock. Adding to the property's unique equestrian history, the farm was once home to the owner's beloved horse, a granddaughter of the legendary Secretariat. A second historic dairy barn adds even more versatility and future potential. Its size, setting, and distinctive character make it suitable for agricultural use, storage, a creative space, a private gathering venue, or a future event or wedding destination. The detached garage provides additional value with an oversized heated and cooled space below and a finished studio apartment above. The apartment includes a full bath and kitchenette, making it ideal for guests, extended family, farm staff, tenants, a private office, or potential rental income. Located just minutes from Interstate 64 and moments from the Simpsonville outlet mall, the property offers the peace and beauty of rural Kentucky without sacrificing convenience. Its central location between Louisville and Lexington also provides easy access to many of the region's premier equestrian destinations, including Churchill Downs, Keeneland, and the Kentucky Horse Park. The home, barns, pond, and approximately 5 acres are being offered together, with the additional adjoining 5-acre tract available separately. Contact the listing agents for details regarding purchase options and possible owner-financing terms. Opportunities offering this level of historic character, usable acreage, equestrian infrastructure, scenic beauty, income potential, and flexibility are increasingly difficult to find in Simpsonville.

4 Beds ⋅ 2 Baths ⋅ 1723903 MLS

1219 Taylor Wood Rd, Simpsonville