Jessamine Homes with Exterior Entry Basement

Jessamine 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 Homes with Exterior Entry 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
$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
$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
$1,488,000
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
$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
$355,000
5 Beds ⋅ 2 Baths ⋅ 26022248 MLS
NEW PRICE IMPROVEMENT PRICED at RECENT APPRAISAL 9/10/26 !!!!!!!! Welcome to 501 Nottaway Drive in Nicholasville, Kentucky! This spacious all-brick ranch offers OVER 3,000 square feet of living space, featuring 5 bedrooms and 2 full bathrooms, including a recently added and beautifully updated primary bedroom suite. The newly renovated kitchen is sure to impress, featuring all-new cabinetry, beautiful granite countertops, and brand-new stainless steel appliances. The spacious kitchen provides plenty of room for cooking, gathering, and entertaining. The primary bedroom suite has been recently updated with fresh paint and all-new luxury vinyl plank flooring. The beautifully refreshed primary bathroom features a new shower, new sink, and new light fixtures, along with a spacious walk-in closet offering excellent storage. The inviting living area features a beautiful brick fireplace with a lovely electric insert, creating a warm and cozy focal point while providing the ambiance and convenience of an electric fireplace. With five bedrooms and a flexible floor plan, this home offers plenty of space for family, guests, a home office, hobbies, or additional living areas. Outside, enjoy a desirable corner lot with a nice, fully fenced backyard, offering plenty of room for pets, children, entertaining, gardening, or relaxing outdoors. Priced very competitively for a quick sale, and the motivated sellers are ready to make a deal! With this much space and so many updates, this house is sure to move quickly—don't miss it! Come see all that 501 Nottaway Drive has to offer. Don't miss your opportunity—come take a look and fall in love!

501 Nottaway Dr, Nicholasville
$475,000
3 Beds ⋅ 3 Baths ⋅ 26022689 MLS
Welcome to this beautifully crafted new construction home, offering 3 bedrooms, 2.5 bathrooms, and a thoughtfully designed open-concept floor plan. 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 an additional bedroom , 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
$429,000
3 Beds ⋅ 3 Baths ⋅ 26022452 MLS
One look and you'll see why this charming ranch with a walk-out basement in Wilmore's desirable Talbott Subdivision checks all the boxes. Tucked away on a quiet dead-end cul-de-sac just minutes from Asbury Seminary and Asbury University, this home offers the perfect blend of comfort, convenience, and curb appeal. From the inviting covered front porch to the mature landscaping, spacious fenced backyard, and brand-new wood deck, the outdoor spaces are made for relaxing and entertaining. Storage is abundant with a walk-in floored attic and additional basement storage. Inside, the open great room features soaring vaulted ceilings, abundant natural light, and a cozy wood-burning fireplace that creates a warm, welcoming atmosphere. The walk-out basement expands your living space with a large family room, beautifully remodeled full bathroom, mudroom, and a versatile bonus room that's perfect for a home office, guest space, workout room, or quiet retreat. Commuters will appreciate being just 15 minutes from the Man o' War and Harrodsburg Road intersection, with most of the drive taking you along the scenic beauty of Harrodsburg Road. Enjoy peaceful small-town living without sacrificing easy access to Lexington's shopping, dining, and amenities.

103 Hager Ct, Wilmore
$900,000
4 Beds ⋅ 4 Baths ⋅ 26021069 MLS
Escape to the countryside in this immaculate 4-bedroom, 3.5-bath home that checks every box. Situated on over 11 acres of lush, secluded land, this property offers the maximum privacy your family craves. Inside, you'll find a freshly painted home featuring a stunning new kitchen remodel—a perfect space with granite counters and premium new appliances. There is plenty of space to host with the large breakfast area and formal dining room. Designed for year-round entertaining, the finished basement boasts a huge recreation room and wet bar, while the expansive covered porches offer the perfect spot to relax on your fully private lot. With a 1st-floor primary suite, three additional bedrooms, and a massive 3-car garage, there is room for everyone. A new roof in the last 4 years and a new HVAC system 7 months ago equal low maintenance for many years to come. Located only 7 minutes from Wilmore and 10 minutes from Nicholasville, this rare find offers a peaceful rural lifestyle without sacrificing proximity to town. The over 11 acre property features maximum privacy at the end of a dead end road, filled with beautiful wooded trails, access to jessamine creek and beautiful waterfalls. The property is filled with abundant wildlife, with deer and turkey frequently sighted out the back door.

405 Lone Oak Rd, Wilmore
$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
$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
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