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 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 Homes with Walkout Basement

$399,900
4 Beds ⋅ 3 Baths ⋅ 26024961 MLS
This is the kind of property that feels like home the moment you arrive! Full of character and warmth, this wonderful one-level home on a walkout basement offers three spacious bedrooms and two full baths on the main level, along with two finished bedrooms/rooms (no window in one) & full bath in the partially finished basement. The heart of the home is a large eat-in kitchen you won't find anywhere else. Warm, welcoming and wonderfully unique, it features a cozy fireplace with attractive built-in pantry cabinets on either side, kitchen has beautifully updated cabinetry, pantry cabinets and granite counters, a five-burner gas range, double oven, updated single bowl sink, plus a second prep sink in the island. Outside you'll discover nearly .40 acres of space backing to green space, lots of privacy and beautiful established landscaping. This property is filled with mature trees and colorful perennials, including a magnificent blooming magnolia, a saw tooth oak and a gorgeous catalpa tree. There's room to play, swings for the kids & porch swings for the adults, a spacious deck off the main level, and an above-ground swimming pool surrounded by a built-in deck along with a recently installed privacy fence. Parking and storage are exceptional, with a two-car carport, drive-around driveway, two-car garage - room for your boat or camper plus abundant storage throughout the home. Improvements in recent years include the roof (2022), HVAC (2025), gutters, siding, soffits (2026), most windows and fresh interior paint, updated kitchen and baths. Two laundry options with a laundry room in the basement and a stackable laundry closet in the primary bath (laundry closet is also plumbed for shower). Character, space, privacy, beautiful grounds and thoughtful updates all come together in a property with so much to offer. Don't miss this one!

202 Natchez Trce, Nicholasville
$579,000
3 Beds ⋅ 3 Baths ⋅ 26024929 MLS
PRICED $20,000+ UNDER APPRAISAL! This exceptional 5-acre property offers space, versatility, and convenience just minutes from town. This nearly 2,000 square foot ranch home features 3 bedrooms and 3 full baths with a spacious living room and large dining room perfect for hosting family and friends. Need more space? The partial basement is ready for your finishing touches and could easily become a 4th bedroom, recreation room, or additional living area. Outside you will find a versatile barn just steps from the home, complete with stalls and two additional garages added to the original structure — ideal for horses, a workshop, or all your hobbies and equipment. Both the barn and field are equipped with underground irrigation and the barn has its own electrical service. With acreage, outbuildings, and endless possibilities, this one-of-a-kind property has everything you've been looking for and more!

1115 Jessamine Station Rd, Nicholasville
$1,625,000
5 Beds ⋅ 5 Baths ⋅ 26024599 MLS
Live where the golf cart becomes your second car! This exceptional home in highly sought-after Equestrian Estates offers more than 5,000 square feet of finished living space on 1.13 acres, with beautiful views of the surrounding farmland. The open floor plan offers first-floor living, including a spacious primary suite spanning the entire left side of the home with two walk-in closets. Five total bedrooms provide plenty of space, while a flexible main-level room can be used as a home office or formal dining room. The finished walk-out lower level features a large family room, two of the bedrooms, 1.5 baths, and a kitchenette—perfect for guests, entertaining, or multigenerational living. Enjoy outdoor living with four separate covered patios located along the back and side of the home. A front-facing garage, spacious circle drive, and convenient drive-through garage add both curb appeal and functionality. And the location is hard to beat! Take a short golf cart ride to Keene Trace Golf Club, offering an 18-hole golf course, par-3 course, resort-style pool, fitness facilities, and upscale dining and bar options. Luxury, space, convenience, and the golf-cart lifestyle—all in one exceptional Equestrian Estates home. Garage orientation was reversed from last time the house was listed. Seller added a circle drive with front entry. New sod where old side driveway was located is being installed 9/8/2026 and the garage doors are being installed on 9/9/2026. Sellers/Builder are Licensed KY Broker/Realtors.

202 The Backstretch, Nicholasville
$329,900
4 Beds ⋅ 2 Baths ⋅ 26024418 MLS
If your family is in need of space, this home has it! This updated home has 4 bedrooms and 2 baths. There is an abundance of extra parking for all your vehicles, recreational vehicles and toys. Plenty of space for entertaining and space for children to play and ride their toys safely in the huge backyard. The kitchen has been upgraded with a stainless steel farmhouse sink, leather granite countertops and stainless steel appliances. New paint and flooring through out the home. The primary bedroom is a nice size; the primary bathroom has been updated and the shower has new glass doors. The walkout basement has the laundry/bonus room area along with another bedroom. There is room to add another bathroom downstairs which means equity! The large 2 car garage is located in the basement off the extra, extra big driveway at the rear of the home. A large storage shed provides extra storage and room for lawn equipment. Homes in this area, with this much yardage does not come by often. This home is eligible for the 0% down, 100% financing through the USDA program. Come see this spacious, updated home and lot today!

800 Pinoak Dr, Nicholasville
$697,000
5 Beds ⋅ 4 Baths ⋅ 26024342 MLS
Incredible opportunity to own this expertly designed and custom-built 5-bedroom, 3.5-bath Ranch home, beautifully situated on 5.12 picturesque acres with breathtaking views and a perfectly positioned pond (Windmill is aerator for the pond)—all conveniently located just minutes from downtown Nicholasville. The exceptional open-concept floor plan is ideal for both everyday living and entertaining, featuring 3/4 inch solid oak flooring (on main level), Hardie board and batten exterior, impressive volume ceilings and an abundance of natural light. The Chef's Kitchen offers stainless steel appliances, a large center island and beautiful quartzite countertops. The first-floor primary suite features an impressive bath and spacious walk-in closet, while a private home office and inviting sunroom provide additional flexibility. Enjoy the warmth and character of two fireplaces, along with a covered front porch and expansive partially covered rear deck overlooking the scenic property. The partially finished walkout lower level features 9-foot ceilings, additional living space, ample storage and a safe room. A detached custom 2-car carport (36 X 24) with storage area (12 X 24) and a large driveway complete this exceptional property. Don't miss the opportunity to experience the privacy, quality and peaceful setting this fabulous home has to offer.

3072 Sugar Creek Pike, Nicholasville
$1,095,000
5 Beds ⋅ 3 Baths ⋅ 26024294 MLS
Refined Country Living in Holloway Estates. Beautifully situated on a one-acre corner lot bordered along the side and rear by deed-restricted farmland, this custom five-bedroom home offers an exceptional combination of privacy, space, and timeless views. From lush pastures and mature trees to breathtaking sunsets, the setting is truly something special—best enjoyed from the expansive vaulted covered deck. Thoughtfully refreshed with new interior paint, lighting, kitchen appliances, and updated landscaping, the home is beautifully presented and move-in ready. Inside, the main level features a spacious kitchen with stainless appliances, designer countertops and a large hidden pantry, along with a striking stone fireplace and generous living spaces designed for both everyday comfort and entertaining. A main-level guest suite with full bath provides flexibility for visitors or multigenerational living, while the formal dining room can easily transition to a private home office, as its currently functioning. A mudroom, dedicated laundry room with utility sink, geothermal system, and large three-car garage complete the main level. Upstairs, the impressive primary suite offers a large walk-in closet, private bath and stunning views, accompanied by three additional bedrooms and another full bath. The full unfinished walkout basement presents an incredible opportunity to create additional living, entertaining, fitness, or recreational space tailored to your lifestyle. Basement has several rooms framed out including a dedicated bathroom that is stubbed out and ready to finish, completed the home would total over 5,100 finished square feet. Offering the serenity of the countryside with the comfort and sophistication of a custom home, this special Holloway Estates property delivers room to breathe, beautiful views, and a setting that's increasingly hard to find.

103 Hidden Meadow Ln, Nicholasville
$1,949,000
6 Beds ⋅ 5 Baths ⋅ 26022718 MLS
An exceptional offering by acclaimed builder Michael Childers, 216 Doe Run is a stunning 2026 Parade of Homes residence showcasing thoughtful design, exceptional craftsmanship, and sophisticated finishes throughout. Offering an impressive 6,508 square feet with 6 bedrooms and 4.5 baths, this newly completed home pairs timeless architecture with the comfort, scale, and functionality of modern living, and was awarded for exterior design landscaping, and superior lighting. From the moment you enter, beautifully curated interiors, quality materials, and impressive architectural details create a home that feels both refined and inviting. Generous living spaces provide plenty of room for both everyday living and effortless entertaining, while six bedrooms offer exceptional flexibility for family, guests, home offices, or additional living spaces. Carefully selected finishes and thoughtful details throughout give the home a distinctive, custom feel. The expansive open floor plan features a Great Room with vaulted ceilings, fireplace, and a wall of glass doors opening to a large covered porch. There is a columned Dining Room with a tray ceiling and beautiful hardwood floors throughout. The chef's kitchen offers white cabinetry, Thermador appliances, and quartz countertops. The finished walkout basement features a Rec Room with an amazing wet bar, two bedrooms, and a full bath. Backing to a large treed green space and on a one-acre lot, the side entry 3-car garage rounds out this very livable home.

216 Doe Run Rd, Nicholasville
$1,488,000
4 Beds ⋅ 4 Baths ⋅ 26023720 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
$260,000
4 Beds ⋅ 2 Baths ⋅ 26023551 MLS
Welcome home to this spacious four-bedroom brick ranch situated on a finished walkout basement! The main level features an inviting living room, kitchen, three bedrooms, and a full bath. Downstairs, you'll find a comfortable den and a generously sized bedroom with a private ensuite, perfect as a primary suite, guest quarters, or multigenerational living space. Enjoy the large, fenced backyard with plenty of room to relax, play, or entertain. Recent updates include a new roof and gutters in 2023 and replacement windows in 2020. Conveniently located near everything Nicholasville has to offer!

228 Laurel Ln, Nicholasville
$2,150,000
5 Beds ⋅ 6 Baths ⋅ 26023508 MLS
Experience luxury living at its finest in the coveted Harrods Ridge neighborhood. Set on a one-acre looking and overlooking the seventh fairway of Golf Club of the Bluegrass (Widow's Watch), this gorgeous, all-brick-and-stone residence offers more than 7,500 finished square feet, five bedrooms, and five and a half bathrooms. Beautiful architectural details and distinctive character are found around every corner! Each upstairs bedroom features a private en suite bathroom and walk-in closet, while one also includes an adjoining bonus or playroom. The expansive primary suite is a private retreat, with dual, oversized walk-in closets and a spa-inspired bathroom, featuring heated tile floors, a soaking tub, and a luxurious, tiled shower. The finished basement is designed for recreation and entertaining, with a massive gathering room, full kitchen and wet bar, theater room, workout room, and guest quarters with built-in queen-and-twin bunk beds. A dedicated golf cart garage provides additional convenience for when it's time to hit the links. Outside, the property truly feels like a private resort. A heated, gunite, saltwater pool steals the show and is accompanied by beautiful, travertine hardscaping. The rest of the property features tasteful landscaping, an irrigation system, and extensive outdoor lighting. A spacious artificial turf area, just beyond the basement doors, provides additional room for entertaining and play without the mess of real grass. Just off the kitchen, a vaulted, covered porch area, with a fireplace, built-in grill, and television creates an inviting outdoor living space just a few steps from the pool. Additional highlights include a three-car garage, stunning golf-course and rural views, and an exceptional combination of privacy, space, craftsmanship, and indoor-outdoor living. Best of all, this peaceful retreat is conveniently located just minutes from the area's premier shopping, dining, and entertainment destinations—offering remarkable accessibility without sacrificing privacy or tranquility.

207 Eagle Dr, Nicholasville
$1,235,000
4 Beds ⋅ 4 Baths ⋅ 26023022 MLS
Special Open House this SATURDAY from 2-4pm * Luxury meets peaceful country living in this exceptional custom-built home on a picturesque 1-acre lot in the sought-after Jewell Pointe community. Built in 2022, this thoughtfully designed residence offers over 4,500 square feet with the convenience of main-level living and upscale finishes throughout. The chef's kitchen features an oversized island that opens to the stunning vaulted great room filled with natural light. The spacious primary suite is a true retreat with a spa-inspired bath, soaking tub, oversized tiled shower, and dual walk-in closets. Upstairs, a finished loft provides flexible living space while an expansive floored attic offers endless possibilities for future expansion. The walkout basement includes a large recreation room, an additional bedroom, and abundant storage. Nearly 800 square feet of covered outdoor living space overlooks breathtaking farmland, creating the perfect setting for entertaining or relaxing. Enjoy the privacy and tranquility of country living while remaining just minutes from downtown Wilmore, Nicholasville, and Lexington. This one-of-a-kind property offers luxury, functionality, and unforgettable views.

108 Peaceful Lndg, Wilmore
$132,000
3 Beds ⋅ 1 Baths ⋅ 26023002 MLS
Rare Investment Opportunity in Edgewood Estates! This approximately 1075 SF Brick home offers 3 bedrooms/ 1 bath, and a full basement. THIS PROPERTY IS BEING SOLD AS-IS IN A LIVE ONSITE AND IN PERSON AUCTION WITH ONLNE PRE-BIDDING AND LIVE SIMULCAST BIDDING. PRICE DOES NOT REFLECT ACTUAL LISTING PRICE. THIS PROPERTY IS BEING SOLD AT ABSOLUTE AUCTION AND WILL SELL TO THE HIGHEST BIDDER. AUCTION IS TUESDAY, SEPTEMBER 15, 2026, AT 7PM. 10% BUYERS PREMIUM ADDED TO FINAL BID TO DETERMINE CONTRACT PURCHASE PRICE. 10% DOWN DUE WITHIN 24 HOURS OF AUCTION ENDING. CLOSE WITHIN 30 DAYS OF AUCTION ENDING.

511 Pinewood Dr, Nicholasville
Start Your Search