Jessamine County Homes with Walkout Basement

Jessamine County Homes with Walkout Basement

Welcome to Jessamine County, Kentucky—a hidden gem nestled in the heart of the Bluegrass region. Known for its picturesque landscapes, friendly communities, and rich history, Jessamine County offers a perfect blend of rural charm and modern conveniences. With its rolling hills, lush pastures, and vibrant local culture, it’s no wonder that families and individuals alike are drawn to this enchanting area.

One of the standout features of Jessamine County is the variety of homes available, particularly those boasting walkout basements. Imagine having a spacious lower level that seamlessly connects to your backyard, providing easy access to outdoor living spaces. Whether you envision a cozy family room, an entertainment area, or even a guest suite, walkout basements offer endless possibilities for customization and expansion.

The homes in Jessamine County with walkout basements are designed to maximize both comfort and functionality, providing ample natural light and a seamless flow between indoor and outdoor spaces. These properties often feature stunning views of the surrounding countryside, allowing you to enjoy the beauty of nature right from your own home.

Living in Jessamine County means enjoying a slower pace of life while still being just a short drive from the vibrant cities of Lexington and Nicholasville. With top-notch schools, beautiful parks, and a strong sense of community, it’s an ideal place to call home. Explore the charm of Jessamine County and discover the perfect home with a walkout basement that suits your lifestyle today!

Newest Jessamine County Homes with Walkout Basement

105 Orange Blossom Dr, Nicholasville
$359,900
3 Beds ⋅ 3 Baths ⋅ 26029898 MLS
Welcome to 105 Orange Blossom Drive, a spacious and flexible ranch-style home in Nicholasville's Orchard neighborhood offering thoughtful updates, multiple living areas, and room to spread out. The main level features approximately 1,737 square feet of above-grade living space with a welcoming front foyer, an office/flex room, an updated kitchen with added cabinetry, appliances, and quartz countertops, plus an open dining area and additional flex space. Down the hall, you will find two bedrooms, a full bathroom, and a first-floor primary suite with a fully renovated private bath. The lower level adds approximately 1,300 square feet of additional basement/lower-level space and offers even more versatility with a separate rear entry, access from the two-car garage, a second kitchen area, separate laundry, a full bathroom, a large living room, and two bonus rooms currently used as bedrooms. Whether you need guest space, work-from-home areas, hobby rooms, recreation space, or multi-generational flexibility, this layout offers options that are hard to find at this price point. Recent improvements include a new roof, new windows, new gutters, new dual-fuel HVAC, updated kitchen finishes, and a renovated primary bath. Outside, the property offers generous parking, two sheds, and a porch off the dining area for enjoying the backyard. With three full bathrooms, multiple flex spaces, a two-car garage, approximately 1,737 square feet above grade, and approximately 1,300 square feet of additional basement/lower-level space, this home offers a strong combination of space, updates, and functionality in an established Nicholasville location close to local shops, restaurants, schools, and everyday conveniences.

105 Orange Blossom Dr, Nicholasville

2109 Chrisman Mill Rd, Nicholasville
$1,495,000
6 Beds ⋅ 6 Baths ⋅ 26028791 MLS
Set on 5 beautiful acres in Jessamine County, this brand-new home, built in 2026, offers the perfect blend of contemporary and traditional design. Experience the privacy and tranquility of country living with convenient access to Lexington and Central Kentucky. This stunning two-story residence pairs a striking brick exterior with over 6,000 finished square feet of thoughtfully designed living space. No detail has been overlooked. From the striking exterior to the meticulously designed interior, this home showcases exceptional craftsmanship, timeless architecture, and sophisticated modern finishes. Beautiful white pine hardwood flooring, elegant arched openings, extensive custom millwork, decorative wainscoting, detailed trim, and designer lighting create an impressive atmosphere throughout. A long driveway leads to a covered front porch and an inviting foyer, where soaring ceilings, elegant chandeliers, and abundant natural light set the tone. There are 10 ft ceilings the 1st and 2nd floor and 9 ft ceiling in the lower level. The main level offers elegant formal spaces featuring custom wainscoting and beautiful architectural woodwork. The living room showcases a gorgeous stacked-stone gas-log fireplace with custom accents. Enjoy a chef's kitchen complete with an oversized island, gas range, double ovens, and an eat-in breakfast area. Don't miss the ceiling-height cabinetry and additional lighting. Coffee and beverage bar with sink off the kitchen with additional storage close by. A convenient butler's pantry with a sink and additional dishwasher. Nearby mudroom drop zone makes everyday living effortless while maintaining an elegant atmosphere. The first-floor primary suite is a true retreat, featuring a spa-inspired bathroom with a freestanding soaking tub, tiled shower, and generous walk-in closet. Ease of access to the deck from the primary bedroom and home office flex space. Both a half bath and laundry on the 1st floor. Upstairs, an exceptionally spacious bonus room accompanies three additional bedrooms and two and a half bathrooms. This oversized recreation room is perfect for a pool table, movie room (with the nearby media closet), or entertaining, with a conveniently located half bath. The finished walk-out lower level features its own kitchen and wet bar with third dishwasher, a large recreation area, two additional bedrooms with egress windows, and a bathroom. This versatile space is ideal for guests, entertaining, a workout room or a potential in-law suite. Outdoors, enjoy a covered patio with beautiful ceiling, deck, front porch, and sweeping rural views. Attached three-car side-entry garage. -Construction Quality, Energy Efficiency & Everyday Comfort- Beyond the impressive architectural details and luxury finishes, this home incorporates a number of construction and mechanical features designed to enhance comfort, functionality, and long-term enjoyment. Additional insulation and air-sealing measures were incorporated into the exterior wall construction, including flash-foam insulation at key framing and sheathing connections to help minimize unwanted airflow and pest intrusion. Sound-dampening insulation was also installed in selected interior walls and floor assemblies, including areas adjoining bedrooms, bathrooms, and shared living spaces. These thoughtful construction details help reduce sound transmission and create a more comfortable indoor environment. A whole-home mechanical ventilation system provides controlled fresh-air exchange, while additional humidity-management equipment supports indoor comfort. The home also features a whole-house hot-water recirculation system designed to reduce the wait for hot water at fixtures throughout the residence. Three large-capacity water heaters serve the property, providing substantial hot-water capacity for a home of this size. Be sure to view the Video Tour, Virtual Floorplan Tour and Home Details sheet.

2109 Chrisman Mill Rd, Nicholasville

104 Deerfield Cir, Nicholasville
$1,250,000
5 Beds ⋅ 5 Baths ⋅ 26028944 MLS
Tucked among the trees in sought-after Barkley Woods, this exceptional 1.5 story home on an acre blends luxury, comfort, and thoughtful design throughout. A soaring two-story foyer welcomes you, where stunning bamboo hardwood floors lead to an open-concept living space overlooking the private wooded backyard. The chef's kitchen features custom glazed cabinetry, bar top for 2, premium Electrolux Icon appliances, including a 66-inch refrigerator/freezer, gas cook top, range hood, and built in combo convection microwave/oven. Vaulted ceilings and shaker wall paneling complete the dining room. The first-floor primary suite offers private access to the covered deck and a spa-inspired bath with dual granite vanities, an oversized marble shower with dual shower head system with the best water pressure ever and toilet closet. A rare first-floor guest suite with a full bath adds flexibility for family and visitors. Additional bonus 1/2 bath. Upstairs, you'll find 3 bedrooms (2 with vaulted ceilings) a bonus room/possible 6th bedroom, office space, large walk in attic, and a Juliet balcony overlooking the great room. The beautifully remodeled walk-out basement is an entertainer's dream. Featuring a stoned, gas fireplace with wood mantle sourced from a KY barn from the 1800s, home theater area, full bath, and area to add a bar/kitchenette. A hidden bourbon-style room behind custom Murphy doors with rustic, barn wood shelving system is sure to excite. The large patio includes a stone retention wall, wood burning fireplace with the same beam mantle, and LED string lights. The bird watching is phenomenal!! Extra bonuses: pantry, aux garage, 2 car garage, double front door, large, covered front porch, foam insulation throughout, Arlo security cameras, roof and gutters 2023, laundry room, coat closet, custom switch plates, meticulously maintained, and on a cul-de-sac in a mature neighborhood complete with a walking trail and green space.

104 Deerfield Cir, Nicholasville

202 Canvasback Dr Unit Lot 73, Nicholasville
$1,695,000
4 Beds ⋅ 5 Baths ⋅ 26028797 MLS
PROPOSED New Construction Opportunity in Drakes Landing! This is your chance to be one of the final homeowners in the highly sought after and exclusive Drakes Landing neighborhood. The lucky buyer will have the first opportunity to choose from Madewell Homes' remaining lot selections in the final phase of this premier community and create a home designed specifically around their lifestyle. Madewell Homes is a fully custom home builder with a passion for bringing each client's vision to life. With a family-owned foundation and over 40 years of combined experience, their team works closely with homeowners through every step of the process to create a truly one of a kind home with exceptional craftsmanship, thoughtful design, and quality that stands the test of time. The possibilities are endless with a custom build -- from architectural details and finishes to layouts tailored for the way you live and entertain. Drakes Landing offers the perfect setting with its established charm, desirable location, and the rare opportunity to build in one of the area's most exclusive neighborhoods. Please note: Photos shown are from a previously completed Madewell Homes project in a similar neighborhood and are provided as examples of the builder's quality, craftsmanship, and design capabilities. Don't miss this rare opportunity to build your dream home in the final phase of Drakes Landing with one of the area's most trusted custom builders

202 Canvasback Dr Unit Lot 73, Nicholasville

101 Kensington Pl, Nicholasville
$1,455,000
4 Beds ⋅ 4 Baths ⋅ 26028635 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

300 Morgan Leigh Ln, Nicholasville
$690,000
4 Beds ⋅ 3 Baths ⋅ 26028563 MLS
Welcome to this stunning, newly built 2025 home in Halfhill Estates, where modern style, thoughtful design, and everyday functionality come together beautifully! Featuring 4 bedrooms, 2.5 baths, and a desirable open floorplan, this home offers a refreshing color palette, abundant natural light, and a pleasing layout designed for comfortable living and effortless entertaining. The amazing kitchen is truly the heart of the home, showcasing beautiful cabinetry, a gas range, a large island, and a spacious pantry to keep everything organized. The adjoining dining area overlooks the backyard, creating a lovely setting for everyday meals and special gatherings alike. Just off the garage, a convenient drop zone provides the perfect place to keep daily essentials neatly tucked away. Even the utility room combines beauty and function with thoughtful details that make everyday routines a little easier. The first-floor primary suite offers a private retreat, complete with an amazing walk-in closet and a well-appointed en-suite bath featuring a relaxing soaking tub and separate stand-up shower. Upstairs, additional bedrooms provide flexibility for family, guests, or a home office. Enjoy outdoor living from the covered back porch, overlooking a fully fenced, tree-lined backyard that offers privacy and room to relax, play, or entertain. The unfinished walk-out basement provides excellent potential for future expansion and is already plumbed for a bathroom, offering an opportunity to customize the space to fit your needs. With its fresh, modern finishes, abundant natural light, functional spaces, and inviting indoor-outdoor flow, this home checks all the boxes. Conveniently located near shopping, schools, and everyday amenities, this beauty is ready to welcome you home!

300 Morgan Leigh Ln, Nicholasville

419 Nottaway Dr, Nicholasville
$250,000
4 Beds ⋅ 2 Baths ⋅ 26027564 MLS
Interest rates come and go but quality built, affordable homes in great, established neighborhoods are like Bigfoot sightings, alien encounters and the Bengals winning the Super Bowl. You believe, you just haven't seen it yet. Welcome to 419 Nottaway, your "too good to be true" address. You could easily move into this all brick ranch on a basement and make updates over time. You will be surprised at what a little paint can do. With minimal work you can pull up carpet and expose hardwood floors or update hinges and door knobs. With next year's tax return you can update the kitchen. At this price, the margins are there for an investor to come in and make some slight cosmetic updates, install new windows and rest easy knowing you are improving a home in an established neighborhood that offers a sure return on investment. If you are the homeowner who opts to purchase and renovate over time, you can rest easy knowing that the full basement means you won't outgrow this great home and the metal roof is there for a lifetime. This unicorn is equipped with a living room, dining room and kitchen on the main level along with 3 additional bedrooms and 1 full bath. The basement is currently set up into 2 areas. To the left at the bottom of the stairs is a great workshop area, the laundry area with an abundance of shelving and a full bath. The right side of the basement has a large den with a fireplace. Imagine the Bengals Super Bowl party you could host. There is a bedroom without windows in the basement. Off the bedroom is a bonus room that would make an amazing craft room or home office. There is also a large storage space as well. The large, level backyard is fully fenced and has ample space for your telescope, so you can check in on your extra-terrestrial friends. There is a storage shed with electric that conveys, so there are no worries about where to store your trail cameras and 'Squatching equipment. The back patio is completely covered, allowing you to enjoy cook outs with friends, family gatherings, gardening or quiet nights balancing your budget so you are ready when rates fall. That's something you can ABSOLUTELY believe in, because they WILL fall and YOU will be ready. Ignore all those non believers !! Call today and see this one for yourself !!

419 Nottaway Dr, Nicholasville

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