Jessamine Homes with Walkout Basement

Jessamine Homes with Walkout Basement

Welcome to Jessamine County, Kentucky, a hidden gem nestled in the heart of the Bluegrass State! Known for its picturesque landscapes, friendly communities, and rich history, Jessamine County offers a unique blend of rural charm and modern convenience. With its rolling hills, lush greenery, and vibrant local culture, it’s no wonder that so many families and individuals are choosing to call this area home.

One of the standout features of homes in Jessamine County is the availability of properties with walkout basements. These versatile spaces not only enhance the functionality of your home but also provide seamless access to the stunning outdoor scenery that this region is famous for. Imagine stepping out of your spacious basement onto a beautifully landscaped yard, perfect for entertaining or simply enjoying a peaceful evening under the stars.

Walkout basements in Jessamine County often come equipped with large windows that flood the space with natural light, creating a warm and inviting atmosphere. Whether you envision a cozy family room, a home gym, or a personal office, the possibilities are endless.

Living in Jessamine County means enjoying a balanced lifestyle—access to top-notch schools, recreational parks, and a close-knit community feel, all while being just a short drive from the bustling city of Lexington. If you're looking for a home that combines comfort, style, and the beauty of nature, Jessamine County's walkout basement properties are the perfect choice. Come explore the charm of this delightful county and discover your dream home today!

Newest Jessamine Homes with Walkout Basement

$899,900
4 Beds ⋅ 4 Baths ⋅ 26020202 MLS
Classic Colonial living on five scenic acres overlooking High Point Golf Course. Perfectly positioned just minutes from Lexington and directly across from world-renowned Taylor Made Farm, this beautifully renovated home has everything you've been looking for. Inside, nearly every room has been thoughtfully updated. The well appointed kitchen showcases quartz countertops with a waterfall edge, refinished cabinetry, new appliances, and custom built-in seating. The family room, with vaulted ceilings, dining room, office, powder room, and laundry room with drop zone complete the main living area. Upstairs, the completely reimagined primary suite features a spa-inspired bath with custom vanities, quartz countertops, a freestanding soaking tub, oversized tiled shower with dual shower heads, and designer finishes throughout. Two other bedrooms, with custom built-ins and generous closets, share an updated Jack and Jill bathroom. The finished walkout basement offers exceptional versatility with a fourth bedroom, updated full bath, and generous living and entertaining space. Step outside to enjoy all seasons on the expansive new deck featuring a screened porch with metal roof, infrared heater, and panoramic golf course views. Major improvements also include a new roof and gutters (2023), HVAC (2024), garage doors, front entry doors, whole-home water filtration and softening system, fresh landscaping, and expanded driveway. Golf enthusiasts will appreciate being a short walk or golf cart ride away from the clubhouse of Thoroughbred Golf Club, featuring brand new Trackman Simulator rooms and a full service restaurant, The Barn. Offering the best of both worlds - peaceful country living with Lexington just minutes away - this truly move-in-ready home is a rare opportunity!

1020 High Point Dr, Nicholasville
$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
$369,900
3 Beds ⋅ 2 Baths ⋅ 26020024 MLS
Welcome to 140 Dawson Pass! Located near City-County Park, this inviting 3-bedroom, 2-bath home offers a desirable split-bedroom floor plan and an open-concept design with a comfortable flow for both everyday living and entertaining. The spacious kitchen, dining, and living areas create the perfect gathering space for morning coffee, family dinners, and hosting friends. Freshly painted ceilings in the living room, kitchen, and primary bedroom, along with freshly painted bedrooms and bathrooms, give the home a fresh and welcoming feel. Plantation shutters throughout add timeless character and charm. Enjoy relaxing evenings and weekend gatherings on the large covered Trex deck, installed in September 2025, overlooking the backyard. Recent updates include a new roof (September 2025), new refrigerator, and new dishwasher, providing peace of mind for the next owner. The expansive 1,599 sq ft walkout basement offers incredible potential with a French door, patio, plenty of windows, and a full bathroom already roughed in. Whether you envision a home gym, media room, hobby space, guest suite, or a comfortable area for multigenerational living, this space allows you to create a home that fits your lifestyle. Sitting on a nice corner lot, this home offers the convenience of nearby parks, outdoor recreation, and everyday amenities while providing room to grow. With thoughtful updates, flexible living space, and a great location, 140 Dawson Pass is ready for its next chapter. Seller is a licensed real estate agent.

140 Dawson Pass, 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
$429,900
4 Beds ⋅ 3 Baths ⋅ 26019703 MLS
Highlights of this home include: * Gorgeous curb appeal with modern board-and-batten accents. * Bright, airy interior with lots of natural light. * Contemporary gray cabinetry with open shelving and stainless appliances. * Family room with fireplace and direct access to the elevated deck. * Raised garden beds already in place for buyers with a green thumb. For the details: Beautiful open-concept home featuring LVP flooring, granite countertops, breakfast bar, eat-in kitchen, dining area, and a spacious family room. A convenient main-level powder room. Upstairs the oversized primary suite offers a double bowl vanity, tiled shower, private water closet, and TWO walk-in closets. You will also find 3 additional spacious bedrooms with ample sized closets to match. The laundry room is conveniently located on the 2nd floor near all of the bedrooms and includes a folding area and cabinetry. (Washer and dryer included!) Enjoy outdoor living on the spacious deck overlooking the fully fenced backyard with a patio below. Gardening enthusiasts will appreciate the thoughtfully planted raised beds filled with herbs and seasonal blooms, including thyme, mint, sunflowers, and more, creating your own backyard garden oasis. The walk-out basement offers endless possibilities for future living space, while the large patio provides even more room to relax and entertain. This home truly offers the perfect blend of modern finishes, outdoor living, and room to grow.

133 Winners Cir, 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
$399,900
4 Beds ⋅ 2 Baths ⋅ 26019332 MLS
Located in the highly sought-after Talbott Subdivision, this beautifully maintained 4-bedroom, 2-bathroom home offers the perfect blend of space, style, and convenience in the heart of Wilmore. Just minutes from Asbury University, local parks, and downtown Wilmore, you'll love the welcoming community and ideal location. Inside, the open-concept living room and kitchen create an inviting space for gathering with family and friends. The updated kitchen features stainless steel appliances, a gas range, and ample cabinet space, while large windows throughout the home flood the interior with natural light. The split-level design provides a functional layout with flexible living space to fit a variety of lifestyles. Outside, the backyard is ready for entertaining or relaxing with an above-ground pool and plenty of room to enjoy the outdoors. Combining thoughtful updates, a desirable floor plan, and an unbeatable location, 516 Talbott Drive is one you won't want to miss.

516 Talbott Dr, Wilmore
$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
$579,900
4 Beds ⋅ 4 Baths ⋅ 26019258 MLS
Tucked away at the end of a quiet cul-de-sac in Nicholasville, 47 Woodbriar Court is the kind of home that feels special from the moment you arrive. Surrounded by mature trees and peaceful views, this property offers a beautiful sense of privacy while still keeping you close to the conveniences of town. The home's charming turret gives it a storybook presence, adding character and architectural interest that makes it stand out in the most memorable way. It creates a feeling of warmth and uniqueness before you ever step through the door. Inside, you'll find spacious, inviting living areas designed for both everyday comfort and meaningful gatherings. The layout offers plenty of room to relax, entertain, and create a home that fits your life beautifully. The finished walkout basement adds even more space and flexibility, perfect for a cozy movie room, guest area, game room, home office, or quiet retreat. Out back, the setting becomes even more special. The deck is ideal for slow mornings with coffee, summer dinners outside, or peaceful evenings overlooking the wooded surroundings. The above-ground pool adds the perfect touch of fun and relaxation, creating a backyard escape where memories can be made all season long. With its wooded lot, private cul-de-sac location, spacious interior, finished walkout basement, deck, pool, and charming turret, 47 Woodbriar Court is more than just a house. It is a place to fall in love with, settle into, and truly call home.

47 Woodbriar Ct, 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
$600,000
4 Beds ⋅ 4 Baths ⋅ 26018900 MLS
ONLINE ONLY ABSOLUTE AUCTION!!! Online BIDDING ENDS Sunday, August 9, 2026 at 7:00PM. Terms & Conditions are as follows: As Is/Non-Contingent/10% earnest money deposit/30 day settlement/buyer's premium applies, see terms & conditions for details. Visit www.HalfhillAuctions.com for more information. Kristin Halfhill-Larimore, Principal Auctioneer, 859-333-1855. **Welcome to 1441 Newman Road, a spacious ranch-style home offering more than 4,000 square feet of finished living space in a beautiful setting surrounded by ±6 acres of greenspace. While the property carries a Lexington address, it is located in Jessamine County. The stone-accented home features 4 bedrooms, with the potential for a 5th bedroom, along with 3 full and 1 half baths. The finished, walk-out basement provides flexible living space for entertaining, recreation, guests, or a home office. Enjoy the outdoors from the large covered back porch overlooking the peaceful greenspace and in-ground pool. Additional amenities include an attached 2-car garage and a detached workshop, offering plenty of space for hobbies, storage, or projects. A rare opportunity to enjoy spacious living, versatile amenities, and a private setting in a convenient location**

1441 Newman Rd, Lexington
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