Jessamine County Real Estate

Jessamine County Real Estate

Located in the state of Kentucky, Jessamine County is a charming and picturesque area that offers a perfect blend of small-town charm and modern amenities. With a rich history dating back to the 1700s, this county is known for its beautiful landscapes, friendly community, and strong sense of community pride.

Jessamine County is home to several vibrant cities and towns, including Nicholasville, the county seat, and Wilmore. These towns offer a wide range of housing options, from historic homes to modern subdivisions, making it an ideal place for families, professionals, and retirees alike.

Nature enthusiasts will find plenty to explore in Jessamine County. The county boasts several parks and nature preserves, including the scenic Jessamine Creek Gorge, where visitors can enjoy hiking, bird-watching, and picnicking. The county is also home to the scenic Bluegrass Scenic Railroad and Museum, which offers train rides through the picturesque countryside.

In addition to its natural beauty, Jessamine County offers a thriving economy with a diverse range of industries. From agriculture and manufacturing to healthcare and education, there are ample job opportunities available in the area.

With its beautiful landscapes, friendly community, and strong economy, Jessamine County is a wonderful place to call home. Whether you're looking for a peaceful retreat or a vibrant community, this county has something for everyone.

Newest Listings in Jessamine County

$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
$224,500
5 Beds ⋅ 2 Baths ⋅ 26020127 MLS
Absolute Auction, Live On-Site Saturday, September 12th. Doors Open at 9:00 am for final preview. Bidding Begins at 10:00 am Sharp. Selling to the Highest Bidder Regardless of Listing Price. Contracted to sell at Absolute Auction Only! Offers Prior to Auction will Not Be Entertained. Please Visit www.bluegrassauction.com for Bidder & Agent Registration Forms and Complete Terms & Conditions. Available for Showings & Inspections Prior to Auction Day. This Fabulous 2 Story Home Boasts Amazing Hardwood Floors In All Rooms except Kitchen & Baths, 10 ft. Ceilings on 1st Floor, 6 Intricately Detailed Fireplaces & Mantles, Formal Living Room, Parlor, Very Large Dining Room with Hallway Access to Large Dine-In Kitchen, 1st Floor Laundry Room, 2 Bedrooms on 1st Floor & 3 Very Large Bedrooms on 2nd Floor. Beautiful Front Living Room Staircase to Spacious 2nd Floor Landing. Rear Staircase with Access to Kitchen. Floored attic and Rear Soffit Storage. Updated Roof in 2024. Only 1/2 Block from Downtown Main Street Shops & Restaurants. Detached Garage with Rear parking Space. Absolute Must See!!! Book Your Showing Today!!! Chuck McKee Auctioneer.

107 Bell Ct, Nicholasville
$180,000
4 Beds ⋅ 2 Baths ⋅ 26020119 MLS
Both sides rented. 24 hour notice to show. Units stay occupied at all times. Great opp

500-502 E 500-502 E Chestnut St Street, Nicholasville
$429,900
4 Beds ⋅ 3 Baths ⋅ 26020117 MLS
The Sutton plan by Houghton Homes is a beautifully crafted two-story home that blends timeless curb appeal with modern, functional living. Designed with comfort in mind, this inviting layout features four spacious bedrooms, including both the primary suite and a second bedroom conveniently located on the main level--perfect for ease of living and flexibility. At the heart of the home, the open-concept kitchen and dining area create a warm and welcoming space for gathering. The kitchen is thoughtfully appointed with 42' soft-close cabinetry, gleaming quartz countertops, a stylish tiled backsplash, a large island for added workspace and seating, and a generous walk-in pantry. A full suite of stainless-steel appliances completes this well-designed space, making it ideal for both everyday living and entertaining. Luxury vinyl plank flooring greets you at the entry and flows seamlessly throughout the main living areas, adding both durability and style. The owner's suite offers a peaceful retreat with a private bath featuring a beautifully tiled walk-in shower, double-bowl vanity with quartz countertops and undermount sinks, and a spacious walk-in closet. Upstairs, you'll find additional bedrooms and an abundance of storage, including a large finished walk-in storage room over the garage. Thoughtful details continue throughout the home with 9-foot ceilings on the main level, 8-foot ceilings upstairs, and ceiling fans in the family room and all bedrooms for added comfort. Step outside to enjoy the 12' x 16' rear patio--perfect for relaxing evenings or hosting guests in your outdoor space. This charming, custom-built home offers the perfect balance of style, comfort, and functionality. Don't miss your chance to make this exceptional Houghton Homes property your own!

417 Krauss Dr, Nicholasville
$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
$483,469
5 Beds ⋅ 3 Baths ⋅ 26020078 MLS
Contract writing period through Thursday, July 30th at NOON. The Greenfield offers a great first floor layout with a large family room opening to a spacious island kitchen and breakfast area. The kitchen features an island design with countertop dining and a corner pantry. The first floor includes a coat closet and full bath, conveniently located off the entry hall, as well as a bedroom at the rear of the home. Upstairs are the primary suite and three additional bedrooms, all with vaulted ceilings. The primary suite includes a large walk-in closet, luxurious bath with double bowl vanity, separate shower, and garden tub. The hall bath features a spacious double bowl vanity. A separate utility room with folding counter is conveniently located on the second floor. Additional primary bath upgrades are possible, and a loft can be configured in lieu of bedroom #4. Job# 46GN

6321 Grey Oak Ln, Nicholasville
$341,677
3 Beds ⋅ 3 Baths ⋅ 26020080 MLS
Contract writing period through Thursday, July 30th at NOON. The Asbury Park, part of the Trend Collection by Ball Homes, is two-story plan with a very open first floor layout with the family room, kitchen, and breakfast area open to one another. The two-car garage is located at the rear of the home and has a side entry. Access to the garage is via a corridor off the kitchen, convenient to the coat closet and the walk-in utility room. The island kitchen offers both a breakfast area and countertop dining, and a large pantry. A covered patio option is available. Upstairs are the primary bedroom suite, and two bedrooms and a hall bath. The primary bedroom suite includes a bedroom with vaulted ceiling, large closet, and spacious bath with tub/shower, and linen storage. Upgrade primary bath options include a garden tub, separate shower, and picture window. Exterior details include a covered entry or front porch, per elevation.

427 Fern Trl, Nicholasville
$369,900
3 Beds ⋅ 2 Baths ⋅ 26020024 MLS
*PROFESSIONAL PICS coming Tuesday* 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.

140 Dawson Pass, Nicholasville
$260,000
4 Beds ⋅ 3 Baths ⋅ 26020053 MLS
Turnkey investment opportunity! FULLY OCCUPIED. $2850 a month income. This newly updated triplex is a strong income-producing asset with updates throughout. Recent renovations minimize deferred maintenance and support long-term performance. The property offers excellent cash-flow with multiple income streams under one roof. Ideal for investors seeking a stabilized or value-add opportunity in a desirable location with convenient access to shopping, dining, and major routes. ** Some photos have been edited to remove tenants personal belongings**

107 Ross St, 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
$935,000
4 Beds ⋅ 3 Baths ⋅ 26020005 MLS
Welcome to the lifestyle you have been dreaming of! Nestled in the desirable Clays Crossing community, this beautiful ranch on almost 3/4 of an acre and a full basement offers over 4,000 sq. ft. of living space. With 3 bedrooms and 2 bathrooms on the main level, and one bedroom with egress and a bathroom in the basement, there is room for everyone to have their own space and walk in closet. The open concept layout is perfect for both everyday living and entertaining, featuring a chef inspired kitchen with a large walk-in pantry and elegant finishes throughout. The majority of the basement is finished with a theater room and wet bar, along with a large gym and luxury sauna. Whether you are hosting game nights, accommodating guests, or want a private space to work out and relax, this basement will provide those unforgeable memories. Located just minutes from Brannon Crossing, South Lexington, shopping, dining, and top amenities, this home delivers the ideal combination of luxury, location, and lifestyle. Don't miss your chance to call 610 Old Coach Rd home!

610 Old Coach Rd, Nicholasville
$340,000
4 Beds ⋅ 3 Baths ⋅ 26019901 MLS
Offering more than 2,200 square feet, this spacious Southbrook home combines standout curb appeal with a comfortable, connected layout. The main level flows easily between the living, dining and kitchen areas, making it well suited for both everyday life and entertaining. New vinyl flooring gives the space a fresh, updated feel, while the kitchen features stainless steel appliances and a newer dishwasher. Upstairs, you'll find all four bedrooms, including a generously sized primary suite with a walk-in closet, plus three additional bedrooms with flexibility for family, guests or a home office. Outside, enjoy a newly replaced upper deck overlooking the privacy-fenced backyard—an inviting space to relax, play or gather. Additional storage, an attached two-car garage and main-level laundry add everyday convenience. Recent improvements also include a rebuilt HVAC system, offering added peace of mind. Located in Nicholasville's established Southbrook neighborhood with convenient access to shopping, dining and Lexington, 404 E Ridge Drive offers the space, updates and functionality that can be difficult to find at this price point.

404 E Ridge Dr, Nicholasville
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