Jessamine Homes with Garage Faces Side Parking Features

Jessamine Homes with Garage Faces Side Parking Features

Welcome to Jessamine County, Kentucky—a hidden gem that beautifully blends small-town charm with modern amenities. Nestled just south of Lexington, Jessamine County boasts a rich history, stunning landscapes, and a vibrant community spirit. With its rolling hills, picturesque farms, and serene lakes, this area is perfect for those seeking a peaceful lifestyle without sacrificing convenience.

One of the standout features of homes in Jessamine County is the availability of properties with side-facing garages. This thoughtful design not only enhances the curb appeal of your home but also maximizes your driveway space, providing ample room for parking and outdoor activities. Imagine pulling into your driveway and being greeted by a welcoming façade that showcases your home’s unique character while keeping your vehicles neatly tucked away.

Residents of Jessamine County enjoy a variety of recreational activities, from hiking and fishing in local parks to exploring charming downtown Nicholasville, where you’ll find delightful shops and eateries. The community is also known for its excellent schools, making it an ideal place for families to grow and thrive.

Whether you’re a first-time homebuyer or looking to upgrade, Jessamine County offers a diverse selection of homes that cater to every lifestyle. With side-facing garage options, you can enjoy the practicality of easy access while maintaining the aesthetic appeal of your property. Discover the perfect home in Jessamine County, where comfort meets convenience, and community thrives. Come experience the charm of this beautiful region today!

Newest Jessamine Homes with Garage Faces Side Parking Features

$1,375,000
5 Beds ⋅ 4 Baths ⋅ 26020148 MLS
Ten acres and a beautiful 2 story brick home with walk out basement in Nicholasville. Yours for horses, hobby farm, or country romp about. Barn, fenced and gated driveway. Great room, large eat at island, formal dining room and gathering room! First floor bedroom. Massive primary suite with soaking tub and walk in closet. Unfinished basement ready for potential recreational dream rooms. One of kind!

1581 Wilmore Rd, Nicholasville
$1,375,000
4 Beds ⋅ 4 Baths ⋅ 26020099 MLS
Set on a private one-acre lot adorned with beautiful, mature trees, this exceptional custom home, one owner home offers privacy, space, and timeless elegance in a Jessamine County golf course setting. A majestic drive welcomes you to the property, creating a striking first impression and a true sense of arrival. Situated on Hole 7, the home is spacious, refined, and thoughtfully designed for both everyday comfort and upscale entertaining. The primary suite is a serene retreat featuring a large, luxurious bath with heated floors. Three additional bedrooms, 4.5 baths, nicely sized closets and generous living spaces provide room for family and guests alike. The home showcases a custom kitchen with Viking professional stainless steel appliances. The butler's pantry is complete with a glass refrigerator, dishwasher and ice machine and there is a wet bar with built-ins and wine cooler. A beautifully appointed office with exquisite trim work, tray ceilings, and lovely chandelier is an ideal place for work or study. A large bonus room and finished space above the garage add flexibility for recreation, guests, or a private retreat. Partially finished basement has a gas fireplace, bar area, half bath, a 100" TV and large home gym. There is plenty of additional storage space in an unfinished area as well. Car enthusiasts and hobbyists will appreciate the 4.5 garage spaces, offering exceptional storage and functionality. The layout flows effortlessly, making the home equally suited for relaxed living or hosting on a grand scale. The resort-style outdoor living area is a true sanctuary, featuring a 20 X 40' salt pool, firepit, covered entertaining space with a television, and a dedicated pool half bath, all surrounded by mature trees that provide privacy, shade, and a tranquil natural backdrop—perfect for both lively gatherings and peaceful evenings overlooking the golf course. While undeniably a luxury home, it is also perfectly suited for children, offering expansive indoor and outdoor spaces to play, gather, and grow—making it as comfortable for family life as it is impressive for entertaining. Located near one of the region's most prestigious and picturesque horse farm, this property offers the serenity of country living while remaining just approximately 9 minutes from Tates Creek Road and Man O' War Boulevard, providing quick access to shopping, dining, and everyday conveniences. A rare opportunity to own a home that blends luxury craftsmanship, natural beauty, family-friendly design, privacy, and prime location in the heart of the Bluegrass.

1056 High Point Dr, Nicholasville
$1,995,500
5 Beds ⋅ 6 Baths ⋅ 26020008 MLS
Discover exceptional craftsmanship in this newest estate by Mike Kerwin Homes, beautifully situated on a one-acre in the rolling hills of Vine Grove, surrounded by more than 200 acres of pristine green space. Thoughtfully designed and masterfully built, this exceptional new plan brings together the most sought-after features from Mike Kerwin's latest custom homes—blending timeless quality with inspired, modern living. Inside, the open-concept floor plan is perfect for entertaining with a chef's kitchen, accented in quartz and Kitchen Concept cabinetry, flowing seamlessly into the great room and complemented by a fully equipped scullery pantry—perfect for housing everything from your pasta maker to sous vide machine. Dining is next level with the dedicated bourbon wet bar, complete with a stunning quartz backsplash with glass shelving designed for memorable evenings with friends. Peak into the powder room to see the hand painted walls that will impress. The luxurious primary suite offers a serene retreat, while a private second-story in-law suite ensures comfort for extended family. The finished walkout basement expands your living space with a wet bar, recreation room, and an additional bedroom and bath—ideal for guests or a nanny suite. Outdoor living is just as impressive. The covered back porch, featuring a masonry fireplace and cathedral bead board ceiling, opens to an adjacent patio overlooking breathtaking views of rolling green space and farmland—an idyllic backdrop for year-round enjoyment. For outdoor enthusiasts and hobbyists alike, the oversized three-car garage includes an auxiliary door for easy access, plus a thoughtfully designed drop zone just inside to keep daily life organized. This is more than a home—it's a statement of craftsmanship, comfort, and Kentucky beauty. You won't be surprised this is a First Prize winner in the Grand Tour of Homes.

128 Doe Vly, Nicholasville
$935,000
4 Beds ⋅ 3 Baths ⋅ 26020005 MLS
Welcome to the lifestyle you have been dreaming of! Nestled in the desirable Clays Crossing community, this beautiful ranch on almost 3/4 of an acre and a full basement offers over 4,000 sq. ft. of living space. With 3 bedrooms and 2 bathrooms on the main level, and one bedroom with egress and a bathroom in the basement, there is room for everyone to have their own space and walk in closet. The open concept layout is perfect for both everyday living and entertaining, featuring a chef inspired kitchen with a large walk-in pantry and elegant finishes throughout. The majority of the basement is finished with a theater room and wet bar, along with a large gym and luxury sauna. Whether you are hosting game nights, accommodating guests, or want a private space to work out and relax, this basement will provide those unforgeable memories. Located just minutes from Brannon Crossing, South Lexington, shopping, dining, and top amenities, this home delivers the ideal combination of luxury, location, and lifestyle. Don't miss your chance to call 610 Old Coach Rd home!

610 Old Coach Rd, Nicholasville
$799,999
3 Beds ⋅ 2 Baths ⋅ 26019873 MLS
Private 5-Acre Sanctuary Just Minutes from Downtown Lexington! Welcome to your private retreat nestled within the exclusive gated community of Village on the Green. Situated on 5 serene acres, this meticulously cared-for, mostly brick home offers over 2,100 square feet of polished, light-filled living space designed for effortless everyday living and entertaining. Inside, you'll discover a thoughtfully laid-out floor plan featuring 3 spacious bedrooms and 2 full bathrooms. The current owners have lovingly maintained and updated the property, offering complete turnkey confidence. Standout upgrades include a whole-home generator, ensuring continuous peace of mind and comfort regardless of the weather. Beyond your private lot, take advantage of the expansive communal green space professionally maintained by the HOA—offering all the benefits of a sprawling park-like setting without the upkeep. Enjoy the best of both worlds: ultimate privacy and acreage in a quiet setting, paired with the convenience of being just a 15-minute drive to downtown Lexington's top dining, shopping, and entertainment options.

17 Olde Village Dr, Nicholasville
$1,750,900
5 Beds ⋅ 6 Baths ⋅ 26019640 MLS
Rare opportunity to purchase a large ranch with a basement on 5 acres and within 10 minutes of Man O' War Blvd!! This lovely ranch has been recently updated and offers tons of upgrades. The first floor greets you with a nice large open living area w/ Great Room, Kitchen, Dining Room and Living Room. In addition, the first floor offers a huge master suite that boasts a renovated bathroom with tile shower/dual vanities/custom WIC and soaking tub, two guest bedrooms (both have their own bathrooms connected), rec room on the rear of the home and walk in laundry room w/ custom cabinetry!! Need more space? This property has it all with a full finished basement that offers a gigantic family room w/ gas fireplace/custom ceiling, second kitchen w/ full complement of appliances, 2nd laundry room, two guest bedrooms w/ full baths connected, cedar storage closet, rec/bonus room, recently added 1/2 bath and storage/mechanical room. This property has tons of nice outdoor space including multiple waterfalls, updated trex deck, covered patio, stocked pond and expansive landscaping/brick fences and stone retaining walls. Other upgrades/updates include: recently updated heating/cooling, new paint throughout, new windows throughout, updated exterior/interior railing, new garage doors/openers, some updated lighting and plumbing, new flooring throughout, new fridge/ice maker in main kitchen and recently painted exterior brick among many others. The property has many upgraded features including heated floors, two koi ponds, solid core doors, granite window ledges, irrigation system with Well water, three gas fireplaces, two tankless water heaters, basement kitchen and an oversized three car garage. Schedule your showing today and experience luxury at its finest in one of Nicholasville's most desirable subdivisions at Emerald Estates.

151 Pearl Ln, Nicholasville
$1,498,000
4 Beds ⋅ 4 Baths ⋅ 26019589 MLS
The Willett of Kensington is an Award Winning Grand Tour of Homes property built by Mitch Canup Homes is now available for purchase. This stunning custom ranch seamlessly blends luxury, functionality, and resort-style living. From its beautifully curated interior finishes to the breathtaking backyard retreat, every detail has been thoughtfully designed to impress. Step outside and enjoy your own private oasis featuring a heated, saltwater pool with a splash pad/ tanning ledge and an automatic cover--perfect for effortless relaxation and entertaining with safety and security in mind. The oversized, vaulted 3-car garage offers incredible versatility, currently serving as an exceptional flex space complete with a wall-mounted basketball goal for year-round fun. With its extra ceiling height, the garage is also lift-ready, making it ideal for car enthusiasts. A rear glass garage door creates a seamless connection to the pool area, transforming the space into a unique indoor-outdoor entertainment hub with endless possibilities. The floor plan is nearly flawless! The Willett has great flow and no wasted space. The efficiency of this open concept split bedroom ranch is practical and impressive. The level of finish and craftsmanship is obvious! Appliances, Flooring, Lighting, Cabinetry and Countertops are all on point. The current owners not only finished the basement beautifully but they mirrored the main floor by using. the same high end finishes to create a space that is equally attractive and inviting. Please take a moment to watch the video that really does show off this amazing property. No fancy gimmicks or explosions needed to show off this show stopper. However, you really must see the home in person to truly appreciate all that it offers. Luxury, recreation, and thoughtful design come together in one remarkable property - welcome home to The Willett of Kensington.

101 Kensington Pl, Nicholasville
$775,000
3 Beds ⋅ 3 Baths ⋅ 26019313 MLS
Rare opportunity to own a meticulously crafted property spanning 5 acres of lush, private land. This residence features a thoughtfully designed 3-bedroom, 3-full-bathroom layout that maximizes natural light and provides a sophisticated retreat from the everyday. The exterior features are equally impressive, anchored by a high-quality 2-stall barn complete with two designated tack rooms, ideal for equestrian pursuits or flexible storage needs. This turn-key property represents the perfect combination of residential comfort and functional outdoor space, ready to welcome its next owner.

1208 Clear Creek Rd, Nicholasville
$900,000
3 Beds ⋅ 3 Baths ⋅ 26019031 MLS
This home doesn't just welcome you in--it draws you in. Set on just over an acre beside the neighborhood water feature, this stunning one-level retreat delivers a quiet, intoxicating kind of luxury where everything feels slower, softer, and more intentional. With over 2,700 square feet under roof, space unfolds effortlessly, inviting you to relax and linger. The split-bedroom design creates privacy where it matters, featuring three bedrooms plus a flex room that adapts beautifully as a fourth bedroom, office, playroom, or formal dining space. The open-concept living area is the heart of the home--perfect for late nights, low lighting, good music, and conversations that stretch on without ever checking the clock. The primary suite is pure escape. Tucked away and quietly indulgent, it offers a spa-inspired ensuite bathroom, a huge walk-in closet, and a private deck made for slow mornings and even slower evenings. Step outside, breathe deep, and let the stillness wrap around you--the water nearby, the air calm, the world just far enough away. A side-entry garage keeps the focus on the home's clean lines and peaceful setting. This is the kind of place where you pour a drink, step outside barefoot, and realize... you're exactly where you're meant to be. Calm, confident, and undeniably alluring--this home is a whole mood.

200 Maple Lawn Cir, Nicholasville
$2,090,000
4 Beds ⋅ 5 Baths ⋅ 26018896 MLS
Experience timeless design and refined Kentucky living in Vine Grove, a beautiful new construction opportunity set on a one-acre lot surrounded by picturesque horse farm views. This thoughtfully designed home blends classic architecture with elevated modern function, featuring a stunning stone entry, warm wood front door, board-and-batten exterior accents, soft green shutters, and a charming French-inspired roofline. The main level offers an exceptional floor plan with a spacious living room, open kitchen, dining area, lounge, private office, mud room, laundry, and a beautifully appointed primary suite. The primary wing includes a generous bedroom, spa-inspired bath, large closet, shoe closet, and direct access to the laundry area. Additional main-level bedrooms and baths provide comfort and flexibility for family, guests, or work-from-home living. The plan also includes a four-car garage, motor court, and elegant porte-cochère, creating a grand arrival experience while adding everyday function. Thoughtful indoor-outdoor flow is designed for both daily living and entertaining. The lower level will be delivered unfinished, offering the future owner flexibility to finish the space at an additional expense based on their preferred design and lifestyle needs. See the floor plan for a sample lower-level layout. Potential options may include a family room, exercise room, safe room, fifth bedroom, full bath, storage, or custom entertaining space, subject to final design, pricing, and builder approval. Located in Vine Grove subdivision and surrounded by rolling horse farm views, this home offers the rare combination of luxury design, privacy, acreage, and convenience. A truly special opportunity to customize a beautiful home in a scenic Central Kentucky setting.

232 Doe Run Rd, Nicholasville
$1,500,000
4 Beds ⋅ 4 Baths ⋅ 26018823 MLS
Nestled among mature trees in the prestigious Barkley Woods community, this one-owner custom-built ranch offers a rare combination of exceptional craftsmanship, timeless design, and an unforgettable natural setting. Backing to a mature tree-lined backdrop and surrounded by a fully fenced backyard, the property offers a level of privacy and tranquility rarely found in today's market. Encompassing 5,228 finished square feet and nearly 6,900 square feet under roof, the thoughtfully designed floor plan is filled with natural light and refined architectural details. Soaring 11-foot ceilings, elegant 8-foot interior doors throughout the main level, rich hardwood flooring, extensive custom millwork, and expansive windows create warm, inviting spaces that seamlessly connect to the picturesque landscape beyond. Designed for effortless entertaining and everyday living, the chef's kitchen is the heart of the home. An oversized quartz island anchors the space, complemented by custom cabinetry, a generous walk-in pantry, and an adjoining butler's pantry with wet bar. Expansive sliding glass doors open to the covered outdoor living area, where peaceful views of the mature trees create the perfect backdrop for morning coffee, family gatherings, or quiet evenings at home. Built by its original owners with an uncompromising commitment to quality, the home features 2x6 exterior wall construction, a four-zone HVAC system for exceptional comfort and efficiency, and an impressive 1,100-square-foot garage with an oversized door that easily accommodates a boat, oversized vehicles, or even a recreational vehicle. Every space has been thoughtfully designed to balance elegance with everyday livability, but it is the setting that truly distinguishes this home. Whether entertaining guests or simply enjoying the peaceful surroundings from your own backyard, this is a property that offers a lifestyle as remarkable as its craftsmanship.

202 Deerfield Cir, Nicholasville
$879,000
4 Beds ⋅ 5 Baths ⋅ 26018565 MLS
Welcome to 337 Hawthorne Drive, an exceptional custom-built home nestled in the highly sought-after Hawthorne subdivision. Offering approximately 5,850 square feet of beautifully designed living space, this impressive residence combines timeless elegance, quality craftsmanship, and modern comfort. Set on one of the neighborhood's most desirable lots, this home offers an uncommon sense of privacy with no neighboring home on the left, direct access to a scenic walking path, and a tranquil pond just steps away. The backyard also backs to picturesque farmland, creating a peaceful, country-like setting while remaining just minutes from Lexington. Inside, you'll find room for everyone to live, work, and entertain in style. A breathtaking two-story great room is filled with natural light and highlighted by custom built-ins and a gas fireplace. The spacious kitchen is a chef's dream, featuring granite countertops, stainless steel appliances, a large center island, and an adjoining sunroom that's perfect for morning coffee while taking in the serene surroundings. The first-floor primary suite serves as a private retreat with a spa-inspired bath featuring a tiled walk-in shower, soaking tub, and oversized walk-in closet. Upstairs, you'll find three generously sized bedrooms, including one with a private balcony, along with two additional full baths. The finished lower level provides exceptional flexibility with expansive recreation and entertainment spaces, guest accommodations, and an additional full bath. Outdoor living is just as impressive. Enjoy the large rear deck overlooking the private backyard, where mature landscaping, open farmland, and the adjacent walking trail create a setting that's both peaceful and picturesque. Whether you're enjoying an evening stroll around the pond or relaxing at home with no immediate neighbor to the left, this property offers a level of privacy that's rarely available in a neighborhood setting. Additional highlights include a 3-car garage, irrigation system, Generac backup power system, and meticulous attention to detail throughout. This is a rare opportunity to own a truly remarkable home in one of Jessamine County's premier neighborhoods. Schedule your private showing today and experience the exceptional lifestyle that 337 Hawthorne Drive has to offer.

337 Hawthorne Dr, Nicholasville
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