Jessamine County Homes with Exterior Entry Basement

Jessamine County Homes with Exterior Entry 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 suburban convenience. With its rolling hills, lush pastures, and serene lakes, this area is not just a place to live but a lifestyle to embrace.

Jessamine County is home to several vibrant towns, including Nicholasville, which serves as the county seat, and Wilmore, known for its quaint downtown and strong sense of community. Residents enjoy a variety of recreational activities, from hiking and biking in the scenic parks to exploring local shops and dining establishments that showcase the best of Southern hospitality.

For those searching for their dream home, Jessamine County presents an exciting opportunity with its selection of homes featuring exterior entry basements. These thoughtfully designed properties offer the perfect blend of functionality and style. An exterior entry basement provides easy access to additional living space, making it ideal for guests, a home office, or a recreational area. Imagine enjoying the convenience of a separate entrance while still being connected to the main living areas of your home.

Whether you’re a first-time homebuyer or looking to upgrade, Jessamine County’s real estate market is thriving. With a range of properties available, you’re sure to find a home that meets your needs and fits your lifestyle. Explore the charm of Jessamine County today and discover why so many are proud to call this beautiful region home!

Newest Jessamine County Homes with Exterior Entry Basement

225 Golf Club Dr, Nicholasville
$1,800,000
6 Beds ⋅ 6 Baths ⋅ 26029563 MLS
Experience exceptional custom-home living in this stunning residence nestled within the gated community of Cambridge East Estates. Situated on approximately one acre with a picturesque setting backing to the Golf Club of the Bluegrass, this beautifully designed home offers an impressive blend of elegance, space, privacy, and versatility. From the striking steel entry door to the soaring ceilings accented by authentic wood beams, rich hardwood floors, and a dramatic stone fireplace, the home showcases distinctive architectural details throughout. The expansive great room, complete with built-in bookshelves, creates a warm yet sophisticated gathering space. The gourmet kitchen features custom cabinetry, granite countertops, an oversized island, and a butler's pantry, making it ideal for everyday living and entertaining. With four spacious bedrooms, private en-suite bathrooms, generous walk-in closets, and two primary suite options on both the first and second floors, the thoughtfully designed layout offers flexibility for a variety of living arrangements. Enjoy dinners on your back covered porch, overlooking the landscaped yard and golf course! Additional highlights include a recently finished lower level, offering a dedicated exercise room, recreation room with kitchenette. There is abundant storage, a 3-car garage, plus a lower level golf cart garage. Enjoy the peaceful surroundings, wooded views, and exceptional setting that make this property truly special. With its combination of custom craftsmanship, generous living spaces, and desirable golf-course location, 225 Golf Club Drive presents a rare opportunity to enjoy an elevated lifestyle in the heart of Jessamine County. Located just a short drive from shopping, restaurants, and downtown Lexington, Discover the possibilities and make this extraordinary property your own.

225 Golf Club Dr, Nicholasville
526 N 3rd St, Nicholasville
$375,000
5 Beds ⋅ 2 Baths ⋅ 26029162 MLS
Looking for lots of space, multi generation home? This is the ONE! Five bedroom brick ranch on full finished basement. Two kitchens one on main level and second in basement. Spacious floor plan with lots of storage. Main level offers large living room with fireplace, primary bedroom and three other bedrooms. Eat-in kitchen with lots of cabinet, counter top space, breakfast bar and walk in pantry. The basement with B Dry system installed in 2019 features the large family room, 2nd kitchen, bedroom and utility room. The backyard with custom steel post privacy fence and 2 entry gates is perfect for enjoying the outdoor and entertaining family and guest. Easy access to the covered deck from main level and patio from the basement walkout right into the large backyard. This is one you don't want to miss. This fantastic home with 3840 finished square footage had roof replaced 2019, new AC 2023 and is conveniently located close to S 27 Bypass , shopping and dining. Property Sold AS IS Inspection welcome

526 N 3rd St, Nicholasville
165 Bernie Trl, Nicholasville
$539,000
5 Beds ⋅ 4 Baths ⋅ 26028651 MLS
Space, flexibility, and room to grow -- this 5-bedroom home at 165 Bernie Trail checks every box! Featuring a rare basement en-suite bedroom perfect for guests, multi-generational living, or a private retreat, this home offers the layout today's buyers are searching for. Step outside to enjoy the covered deck, ideal for relaxing evenings, morning coffee, or entertaining rain or shine. A versatile bonus room adds even more flexibility and could easily serve as a playroom, home office, workout space, media room, or hobby area. The finished basement also includes a large utility garage with endless possibilities for storage, hobbies, lawn equipment, or a workshop setup. With generous living space and functional extras throughout, this is the kind of home that truly fits real life.

165 Bernie Trl, Nicholasville
420 Krauss Dr, Nicholasville
$469,000
3 Beds ⋅ 3 Baths ⋅ 26028639 MLS
Stop scrolling you found the one!! Welcome to this beautifully crafted new construction home, offering 3 bedrooms, 2.5 bathrooms, and a thoughtfully designed open-concept floor plan on a finished walk out basement. With luxury finishes throughout, this home blends modern style, comfort, and functionality. The spacious main level features an inviting living room that flows seamlessly into the dining area and chef-inspired kitchen, guest bathroom, laundry, complete with quality finishes and plenty of space for entertaining. The primary suite provides a private retreat with a luxurious bath and walk-in closets. The finished walk-out basement expands the living space with TWO additional bedrooms , full bathroom ,open great room—perfect for a media area, recreation room, home office, or entertaining. Step outside to enjoy the back patio and take in the lovely views overlooking peaceful green space. With its modern design, spacious living areas, luxury finishes, and desirable indoor-outdoor living, this exceptional new construction home is ready for its new owner!

420 Krauss Dr, 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
1603 West Ln, Nicholasville
$985,000
4 Beds ⋅ 4 Baths ⋅ 26027951 MLS
1603 West Lane presents a rare opportunity to own a private 32-acre retreat in the heart of Jessamine County. Tucked away in a peaceful country setting, this property combines open space, water views, and the comfort of a spacious home... offering the kind of lifestyle that's increasingly hard to find in Central Kentucky. Inside, the home features just under 4,000 square feet with 4 bedrooms and 3.5 bathrooms, designed to accommodate both everyday living and easy entertaining. Generous living areas provide room to spread out, while the layout supports flexibility for family, guests, or multi-purpose use. Outdoors, the acreage is the true standout. Rolling land, a pond, barn, and endless potential for recreation, livestock, gardening, or simply enjoying the quiet of your own private escape. All of this while still maintaining convenient access to Nicholasville, Lexington, and nearby city amenities, making it the ideal balance of country living without compromise. Don't miss this opportunity!

1603 West Ln, Nicholasville
136 Lake Country Rd, Nicholasville
$495,000
3 Beds ⋅ 3 Baths ⋅ 26027903 MLS
Absolute Auction -----POSTPONED! The Auction for this Property has been postponed and a new date will be announced in the future. **During this time Serious Offers made under Auction Terms Will be Considered. Please Visit www.Bluegrassauction.com for Complete Terms & Conditions, Bidder & Agent Registration Forms. A Fabulous Opportunity to own this Sprawling Ranch Home Nestled on 5 Beautiful Acres. Enjoy peaceful rural living with the convenience of being just minutes from town. This lovely ranch home with finished basement offers 3 spacious bedrooms, 3 bathrooms, main level laundry room, dining room, dine-in kitchen, a large den with fireplace, formal living room, Large screened in rear deck/porch overlooking fields and trees. The basement offers a generous home office, full bath, family room with fireplace and access to attached double garage with additional laundry. Home Updates Include: New Roof 2023, New HVAC System 2023 & New Gutters & Downspouts 2024. Located behind the home is a very generous, detached garage/workshop and large field with back tree line. Don't Hesitate....Book Your Showing Today!! Chuck McKee - Auctioneer.

136 Lake Country Rd, Nicholasville
125 Doe Vly, Lexington
$1,599,000
4 Beds ⋅ 5 Baths ⋅ 26026523 MLS
Welcome to 125 Doe Valley, where luxury living meets sweeping farmland views in Vine Grove! Currently under construction just across the Fayette County line in Nicholasville, this stunning new home offers over 3,500 square feet of finished living space, a three-car garage, and a full unfinished walkout basement with room for future expansion. Thoughtfully designed with four bedrooms, each featuring a dedicated bathroom and walk-in closet, the home includes a first-floor primary suite and luxury finishes throughout. Customization options are still available, offering the opportunity to make this home your own. Stunning views of protected farmland create a scenic backdrop, while Brannon Crossing and Tates Creek Centre are less than 10 minutes away. An exceptional opportunity to enjoy new construction, beautiful surroundings, and convenient access to Lexington.

125 Doe Vly, Lexington
201 Appaloosa Trl, Wilmore
$1,685,000
3 Beds ⋅ 4 Baths ⋅ 26026018 MLS
Experience luxury country living in this striking, brand-new custom home situated on five scenic Bluegrass Kentucky acres. Boasting approximately 4,000 square feet and three master suites on the main first floor, plus another 4000 sf of unfinished walkout basement and a 500 sf bonus room above the garage, this thoughtfully designed residence combines an open, upscale floor plan with the privacy and beauty of the Kentucky countryside. The exterior showcases light brick and stone, dramatic black-and-white architectural accents, a three-car side-entry garage, a circular front walkway feature, and an impressive, curved concrete driveway. Inside, the first-floor primary suite, spacious gathering areas, cozy gas fireplace, and carefully selected premium finishes create a comfortable yet refined setting. A walkout lower level and covered upper and lower outdoor-living spaces provide exceptional opportunities for relaxing and entertaining while enjoying calm and serene surrounding views. Final interior finish work, grading, and landscaping are currently underway. The five-acre setting offers room to enjoy the outdoors, with horses, farm animals, and outbuildings permitted. Public water, underground electric, and fiber-optic service add modern comfort and convenience. Peaceful and private, yet conveniently connected to Wilmore, Nicholasville and Lexington via US 68, this distinctive luxury estate delivers space, style and country living without sacrificing accessibility. The list of details is so long that we can't include everything here. Breathtaking views of the Kentucky countryside all around. Don't miss this one-of-a-kind gem. Call now for more details; you still could be able to pick your finishes!

201 Appaloosa Trl, Wilmore
221 Doe Run Rd, Nicholasville
$1,356,000
3 Beds ⋅ 4 Baths ⋅ 26025661 MLS
Proposed new construction by Steven Poor Custom Homes in beautiful and convenient Vine Grove on a scenic 1 acre lot. Great split bedroom ranch design with 10'and 12' ceilings, full unfinished basement, 3 car garage and premium features throughout. Open to building your plan at this time!

221 Doe Run Rd, Nicholasville
202 The Backstretch, 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
103 Hidden Meadow Ln, Nicholasville
$989,000
5 Beds ⋅ 3 Baths ⋅ 26024294 MLS
Incredible New Price Due to Relocation- 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
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