Jessamine County Homes with Detached Parking Features

Jessamine County Homes with Detached Parking Features

Welcome to Jessamine County, Kentucky—a hidden gem that beautifully blends the charm of small-town living with the convenience of modern amenities. Nestled just south of Lexington, Jessamine County boasts picturesque landscapes, rich history, and a vibrant community spirit that makes it an ideal place to call home.

As you explore the diverse neighborhoods of Jessamine County, you'll discover an array of homes that cater to every lifestyle. Among the most sought-after features are homes with detached parking. These properties often come with spacious garages or carports, providing not only convenience but also a touch of elegance to your living space. Imagine the ease of parking your vehicle just steps away from your front door, while still enjoying the privacy and aesthetics of a beautifully landscaped yard.

The county's real estate market is thriving, offering a variety of homes that range from charming historic properties to modern builds. With detached parking options, you can enjoy the benefits of additional storage space for tools, recreational vehicles, or even a workshop—making it a perfect choice for hobbyists and families alike.

Living in Jessamine County means having access to excellent schools, beautiful parks, and a strong sense of community. Whether you're taking a stroll through the quaint downtown area or enjoying a weekend at one of the local festivals, you'll quickly find that this county offers a welcoming atmosphere.

If you’re searching for a home that combines comfort, practicality, and a sense of belonging, Jessamine County is the place for you. Explore the possibilities today and discover your dream home with detached parking features in this enchanting part of Kentucky!

Newest Jessamine County Homes with Detached Parking Features

1895 Clear Creek Rd, Nicholasville
$1,295,000
4 Beds ⋅ 3 Baths ⋅ 26028309 MLS
Exceptional 24-acre equestrian property in Nicholasville offering the best of Bluegrass country living! The spacious, custom-built 3,295-square- foot home features 4 bedrooms, 2.5 baths, and a versatile first-floor office that could serve as a 5th bedroom. A lovely two-story foyer welcomes you into the home, with hard wood floors continuing into the dining room, accented by classic wainscoting. The family room's focal point is a stunning stacked-stone fireplace with gas logs and built-ins. The kitchen features Corian countertops, loads of cabinetry space, and newer stainless-steel appliances. The first- floor primary suite offers a private retreat with an en-suite bath featuring dua| vanities, a separate shower, and a relaxing jacuzzi tub. Three generously sized bedrooms and a full guest bath complete the second floor. Enjoy outdoor living from the covered porch and covered patio. Equestrian amenities include an impressive 10-stall barn with water and electricity, laundry room and feed room, fenced paddocks, and a picturesque pond. A 2-car attached garage, 2- car detached garage (both oversized), and covered 40' x 41' carport provide exceptional parking, storage, and space for farm equipment or trailers. A whole-house generator and lightning rods protection add peace of mind. With 24 acres offering endless possibilities for equestrian pursuits, farming, recreation, or simply enjoying the tranquility of the Kentucky countryside, this remarkable property is a rare opportunity near Nicholasville and Lexington!

1895 Clear Creek Rd, Nicholasville
217 S Main St, Nicholasville
$599,700
5 Beds ⋅ 5 Baths ⋅ 26026997 MLS
Completely Renovated 5BR/5BA Luxury Home — 4,600+ Sq Ft in the Heart of Nicholasville! Welcome to 217 South Main Street — a stunning luxury home offering over 4,600 square feet of beautifully renovated living space, right in the heart of Nicholasville, Kentucky. This 5-bedroom, 5-bathroom home has been completely transformed from top to bottom, delivering a true turnkey experience with high-end finishes throughout, including a convenient first floor primary bedroom. The kitchen shines with gorgeous quartz countertops and a stylish tile backsplash, while the bathrooms feature luxury tile finishes that elevate every detail. Refinished flooring flows throughout the home, bringing a fresh, polished feel to every room. Outside, you'll love the massive back deck — perfect for entertaining or simply relaxing — along with a newly fenced-in backyard offering privacy and space to enjoy the outdoors. With this much space, style, and quality craftsmanship, this home truly has it all. Don't miss your chance to own this one-of-a-kind luxury home in the heart of Nicholasville — schedule your showing today!

217 S Main St, Nicholasville
215 Danville Loop 1 Rd, Nicholasville
$499,800
3 Beds ⋅ 2 Baths ⋅ 26026498 MLS
PROFESSIONAL PHOTOS being taken soon. Looking for that hard-to-find rural oasis? With nearly 3 acres, this charming, updated all-brick farmhouse offers the perfect opportunity to create your own mini-farm sanctuary, conveniently located to Nicholasville, Lexington and Danville and just a short drive to Herrington Lake! The covered front porch welcomes you with plenty of space to sit, relax and gather. Inside, the bright and cheerful renovated interior features gorgeous hardwood floors throughout, along with an updated kitchen boasting generous cabinetry, quartz countertops, stainless appliances and a large movable island. The main level also includes a bedroom and versatile additional room—perfect for a home office, hobby room or potential bedroom. Upstairs, you'll find two exceptionally spacious bedrooms, each approximately 400 sq. ft., with generous walk-in closets. Both full baths have been updated with new vanities, flooring and tile. The sellers have roughed in two rooms and added electrical sources, giving you a great head start on future finished space and now ready for your ideas. The infrared sauna conveys with the home. Outside, enjoy a wonderfully flat yard with firepit, pergola, gardens and chicken coop (chickens are being rehomed), plus approximately 400 sq. ft. of covered porch space across three porches. The 700+ sq. ft. garage/workshop provides plenty of room for vehicles, tools, hobbies and more. Sellers have not use the third structure that needs repair, and note: the two outbuildings currently do not have power. UPDATE: With an acceptable contract, Sellers will add or provide credit for 200 amp service to be run to detached garage/workshop. Replacement windows and new exterior doors add to the updates. Bring your vision and enjoy the space, privacy and simple pleasures of country living—all within easy reach of town!

215 Danville Loop 1 Rd, Nicholasville
1730 Woods Rd, Nicholasville
$739,000
3 Beds ⋅ 2 Baths ⋅ 26019682 MLS
Experience refined country living on approximately 5 picturesque acres in one of Jessamine County's most desirable areas. Surrounded by beautiful farms and rolling countryside, this stately Bedford stone residence offers 3 bedrooms, 2 bathrooms, a sun-filled sunroom, and an unfinished basement providing exceptional potential for future living space, a wine cellar, home gym, or additional storage. Equestrian and agricultural amenities include two fenced pastures, an impressive barn with stalls, multiple storage buildings, and a detached garage perfectly suited for horses, livestock, equipment, or a private hobby farm. Public water is available in the area; however, the property currently enjoys crystal-clear water from a 68-foot well. Ideally located near Champion Trace Golf Club and just minutes from Lexington, Versailles, and Nicholasville, this exceptional property offers the rare opportunity to enjoy peaceful, private country living without sacrificing convenience. Create your own elegant equestrian retreat, luxury mini farm, or timeless Kentucky estate. Bedford stone homes are classic homes built with (or faced in) Indiana limestone, commonly called Bedford stone because it comes from the quarries around Bedford, Indiana. This durable limestone became extremely popular throughout Kentucky and the Midwest from the 1940s through the 1970s. They are known for: * Thick limestone exterior that is exceptionally durable and can last for generations. * Excellent curb appeal with a timeless, stately appearance. * Superior fire resistance and low exterior maintenance. * Ranch-style, split-level, and traditional two-story designs are the most common.

1730 Woods Rd, Nicholasville
2419 Shun Pike, Nicholasville
$799,900
4 Beds ⋅ 4 Baths ⋅ 26019626 MLS
Hobby Farm on 5± Acres | Privacy, Charm & Modern Updates Welcome to 2419 Shun Pike, a stunning French Country brick colonial nestled on approximately 5 picturesque acres in an exceptional location. Offering timeless curb appeal, quality craftsmanship, and thoughtfully updated interiors, this one-of-a-kind property is the perfect blend of classic elegance and comfortable country living. Inside, you'll find 4 spacious bedrooms, (an office that coud be used as a 5th bedroom) including 2 spacious ensuite bedrooms, 4 full bathrooms, 2 inviting living areas on the main level, 2 laundry rooms, and an expansive sunroom filled with natural light. The beautifully renovated kitchen features quartz countertops, custom cabinetry, stainless steel appliances, a huge center island and is designed for both everyday living and entertaining. Recent improvements include new flooring, updated lighting and ceiling fans throughout, fresh landscaping, electrical outlets/covers, Radon mitigation system installed and a newly constructed one-car garage completed in 2025. Outside, the property truly shines. The fully functional barn is ideal for a hobby farm, horses, livestock, or equipment storage, while the impressive 5-car detached garage offers abundant space for vehicles, recreational toys, or workshop needs. And as a bonus you can cool off, relax and take in the views from the above ground pool. Set back from the road for exceptional privacy, this beautiful property offers the tranquility of country living with the convenience of shopping, dining, and everyday amenities just minutes away. Whether you're dreaming of a hobby farm, need room to spread out, or simply want a beautifully updated home on acreage, 2419 Shun Pike is a rare opportunity you won't want to miss. Pool can be removed at buyers request.

2419 Shun Pike, Nicholasville
504 Barberry Ln, Nicholasville
$365,000
4 Beds ⋅ 2 Baths ⋅ 26018833 MLS
Welcome to this beautifully renovated 4-bedroom, 2-bath ranch in the desirable Edgewood subdivision of Nicholasville. Thoughtfully updated from top to bottom, this home offers the feel of new construction with the charm of an established neighborhood. Inside, you'll find stylish new flooring, updated lighting, and modern ceiling fans throughout. The kitchen is a true highlight, featuring brand-new cabinetry, sleek appliances, and eye-catching blue accents that add just the right amount of character. Both bathrooms have been fully refreshed with contemporary vanities, mirrors, and lighting for a clean, polished look. The living room showcases a striking accent wall, creating a warm and inviting focal point. Outside, the oversized two-car garage and dual driveways provide plenty of space for extra parking—perfect for a boat, camper, or RV. Move-in ready and designed with both style and function in mind, this home is one you won't want to miss.

504 Barberry Ln, Nicholasville
515 Pinoak Dr, Nicholasville
$316,900
4 Beds ⋅ 2 Baths ⋅ 26017351 MLS
Welcome home to this beautifully maintained 4-bedroom, 2-full-bath residence that combines modern updates with spacious living. The heart of the home features custom cabinetry and granite countertop, offering both style and functionality for everyday living. Enjoy peace of mind with numerous recent improvements, including a roof that's only 2 years old, replacement windows installed in 2020, brand-new gutters (2025), and a new stamped stone concrete front porch and concrete driveway (2025). The fully finished basement provides abundant additional living space, perfect for a family room, home office, recreation area, or guest accommodations. Outside, you'll find a large, fully fenced backyard with a chain-link fence—ideal for children, pets, gardening, or entertaining. Located in a quiet, established neighborhood, this home offers the perfect balance of tranquility and convenience, with restaurants, shopping, and everyday amenities just minutes away. Large 2 car detached brick garage and new stamped stone concrete front porch and large concrete driveway. With its generous living space and generous storage, quality updates, and excellent location, this move-in-ready home is one you won't want to miss!

515 Pinoak Dr, Nicholasville
1395 Dix Dr, Wilmore
$344,000
2 Beds ⋅ 3 Baths ⋅ 26011589 MLS
Kentucky Palisades at High Bridge retreat on 3 wooded lots featuring a beautifully maintained elevated home and an exceptional 1800+ sq. ft. detached shop. Perfect for hobbyists, collectors, or workshop space. The insulated outbuilding includes HVAC, full bath & 3 bonus rooms, The home offers 2 bedrooms, 1.5 baths plus a sleeping loft, with vaulted ceilings, hardwood floors, skylights, granite countertops, custom cabinetry walk-in closet, and a full-height masonry fireplace with wood stove. Enjoy peaceful river views from the expansive screened porch. Offered fully equipped, including stackable washer and dryer. A rare waterfront property combining comfort, privacy, and incredible versatility. Boat ramp nearby for the community . Breathtaking views for the fun summer family gatherings. Lots 42, 43 & 44.

1395 Dix Dr, Wilmore
1224 Hall Rd, Nicholasville
$825,000
3 Beds ⋅ 4 Baths ⋅ 26012726 MLS
A charming and truly exceptional retreat in Nicholasville and will be a great place to call home. On a total 3.75 picturesque acres, this stunning ranch on a full basement is a modern escape while remaining conveniently close to town. From the moment you step inside, the home makes a statement. Natural light and Kentucky sky. Every space has been thoughtfully done with a sophisticated design that blends contemporary elegance and livability. Show stopping kitchen is straight from the pages of a luxury design magazine, featuring custom cabinetry. Granite Counter tops and island, premium appliances, and expansive gathering spaces ideal for entertaining. The hardwood floors elevate the rooms. Offering 3 bedrooms and 3 1/2 baths, the layout provides both comfort and flexibility.Spacious,first floor primary suite is a peaceful sanctuary. While the full basement opens endless possibilities for hobbies, work spaces,entertaining,or multi-generational living. Perfect for a studio. A detached garage/workshop building adds functionality, outdoor living. Equally impressive with a patio designed to soak in the extraordinary scenery and sunsets.Elegant,private,and unforgettable-this is a once-in -a-lifetime opportunity to own a property that feels both luxurious and deeply connected to its natural surrondings.Inspections welcome. Home is in Jessamine County. Please schedule a private showing today.

1224 Hall Rd, Nicholasville
521 N Lexington Ave, Wilmore
$239,900
7 Beds ⋅ 6 Baths ⋅ 26013301 MLS
Calling all restoration enthusiasts, preservationists, and seasoned investors! Opportunities like this don't come around often. Situated on a generous 0.69-acre lot in the heart of Wilmore, this historic Colonial-style home is waiting for the right buyer to bring it back to life. This is not a cosmetic fixer-upper. The property requires extensive renovation and is best suited for those with the vision, resources, and expertise to undertake a significant restoration project. For the right person, however, the result could be extraordinary. Inside, you'll find over 6 bedrooms, 3 full bathrooms, 1 half bathroom, and an additional vanity room, along with a massive living room, spacious eat-in kitchen, abundant storage, original wood trim, historic architectural details, and multiple bedrooms featuring ensuite baths. A screened-in porch offers additional space to enjoy the property's peaceful setting. Adding to the property's appeal is a separate 1-bedroom, 1-bath dwelling located on the lot, providing additional possibilities for future use. Conveniently located near downtown Wilmore, Asbury University, and Asbury Theological Seminary, with easy access to Nicholasville and approximately 15 minutes from Lexington, this property combines small-town charm with accessibility. Whether your vision is restoring a grand historic residence, creating a multi-generational living arrangement, or undertaking a one-of-a-kind investment project, this property offers a rare opportunity to preserve a piece of Wilmore's history. Property is being sold as-is. Please allow 7 days to be listed before reviewing offers.

521 N Lexington Ave, Wilmore
1368 Keene South Elkhorn Rd, Nicholasville
$2,795,000
3 Beds ⋅ 5 Baths ⋅ 26013315 MLS
Welcome to 1368 Keene South Elkhorn Road, a rare opportunity to own a truly turn key 20 acre horse farm! Conveniently located near Versailles and Lexington, it has been home to multiple stakes winners and Arkansas and Kentucky Derby contenders! Located at the end of a quiet country lane, you'll appreciate the curb appeal of the home from the second you drive up. Step on to the wrap around porch and enter in to the airy two story foyer. To your left, you'll find the poplar paneled study with built-ins and fireplace. To your right, the spacious formal living room opens to the formal dining room. The kitchen boasts reclaimed hardwood floors from Hamburg Place, two refrigerators, walk in pantry, two sinks, breakfast nook, massive center island with cooktop and an Aga stove. A lovely screened porch, half bath and laundry room are off the kitchen. The first floor primary suite is generously sized and offers an en-suite bath and walk-in closet. Upstairs, you will find two large bedrooms, each with en-suite bathrooms and walk-in closets. The lower level features a bar area, theater room, sauna, guest quarters, spa like bathroom, home gym, office and plenty of storage space. The two car detached garage is at the rear of the home and has a staircase leading to storage above. There is also a 16x16 heated and cooled dog kennel building behind the garage. The 12 stall Amish built metal barn with 40x40 arena offers a tack room, tankless water heater, 2 wash/grooming stalls, hay loft and covered concrete pad for equipment storage. Other outdoor features include 7 paddocks, new 4 board fencing, recently paved driveway, Varnan waterers, and a small vineyard with multiple fruit trees including apple, pear, pawpaw, peaches, figs, apricots and plums. You'll love the location, just minutes from grocery stores, restaurants and Keeneland, and close to prestigious farms like Darley, Shadwell and Mill Ridge.

1368 Keene South Elkhorn Rd, Nicholasville
305 1/2 S 3rd St, Nicholasville
$238,900
3 Beds ⋅ 2 Baths ⋅ 26016173 MLS
Priced below recent appraisal. Welcome home to this adorable, beautifully updated 3-bedroom, 2-bath ranch offering timeless character and exceptional storage. Original hardwood floors in excellent condition flow throughout much of the home, while the updated kitchen blends modern convenience with classic charm, featuring granite countertops, a tile backsplash, and the home's original wainscoting that has been lovingly preserved. Both bathrooms have been tastefully updated, and replacement windows provide added efficiency and comfort. The convenient main-level utility room includes the washer and dryer. Storage is abundant with an unfinished basement, an incredible floored attic with pull-down stairs, and multiple outbuildings. Outside, you'll find an attached carport with a storage shed, plus a second detached carport complete with a storage closet and workshop--perfect for hobbies, tools, or extra vehicles. Enjoy relaxing on the covered back patio or flat, partially fenced backyard. This move-in-ready home offers the perfect combination of character, updates, and functionality.

305 1/2 S 3rd St, Nicholasville
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