Jessamine Homes with Garage Faces Side Parking Features

Jessamine Homes with Garage Faces Side Parking Features

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 unique blend of rural charm and suburban convenience. With its rolling hills, lush farmland, and vibrant local culture, this area is perfect for families, professionals, and anyone looking to enjoy a peaceful yet connected lifestyle.

One of the standout features of homes in Jessamine County is the popular side-facing garage parking. These thoughtfully designed homes not only enhance curb appeal but also provide practical benefits. Side garage entries allow for a more aesthetically pleasing façade, keeping the front of the home open and inviting. This design choice maximizes your driveway space and contributes to a neater streetscape, making your property stand out in the neighborhood.

Living in Jessamine County means you’ll enjoy easy access to a variety of amenities, including parks, shopping centers, and top-rated schools. The county is known for its strong sense of community, with numerous events and festivals that bring residents together throughout the year. Whether you’re an outdoor enthusiast exploring the scenic trails or a food lover indulging in local cuisine, Jessamine County has something for everyone.

If you’re considering a move to this charming area, the homes with side-facing garages offer a blend of style, functionality, and convenience that is hard to beat. Discover your dream home in Jessamine County and experience the warmth and beauty of Kentucky living!

Newest Jessamine Homes with Garage Faces Side Parking Features

$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
$449,500
3 Beds ⋅ 3 Baths ⋅ 26024258 MLS
Hard to find ranch home with this much square footage. Extra large side entry garage plus extra side drive for you RV, boats or other toys. Lots of remodeling in 2021 includes new roof, HVAC, all baths and kitchen. 5 x 21 above ground pool added with all accessories in last couple of years for the grandkids. Large corner lot in desirable Keene-Land subdivision

600 Keene Way, 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
$875,000
3 Beds ⋅ 3 Baths ⋅ 26023809 MLS
This home doesn't just welcome you in--it draws you in. Set on just over an acre beside the neighborhood water feature, this stunning one-level retreat delivers a quiet, intoxicating kind of luxury where everything feels slower, softer, and more intentional. With over 2,700 square feet under roof, space unfolds effortlessly, inviting you to relax and linger. The split-bedroom design creates privacy where it matters, featuring three bedrooms plus a flex room that adapts beautifully as a fourth bedroom, office, playroom, or formal dining space. The open-concept living area is the heart of the home--perfect for late nights, low lighting, good music, and conversations that stretch on without ever checking the clock. The primary suite is pure escape. Tucked away and quietly indulgent, it offers a spa-inspired ensuite bathroom, a huge walk-in closet, and a private deck made for slow mornings and even slower evenings. Step outside, breathe deep, and let the stillness wrap around you--the water nearby, the air calm, the world just far enough away. A side-entry garage keeps the focus on the home's clean lines and peaceful setting. This is the kind of place where you pour a drink, step outside barefoot, and realize... you're exactly where you're meant to be. Calm, confident, and undeniably alluring--this home is a whole mood.

200 Maple Lawn Cir, 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
$1,595,000
5 Beds ⋅ 4 Baths ⋅ 26023646 MLS
Luxury new construction with elevated quality in prestigious Drakes Landing! Sophisticated modern 5 bedroom 3 1/2 bath ranch with a 3-car garage on a full finished basement with a well thought out plan. The living room will capture your attention with the towering ceiling, hardwood flooring, natural light, and a beautiful fireplace with wainscoting and lovely built-ins. This home is adorned with elegant crown molding, 8-foot doors, tiled bathrooms and timeless design throughout. You will enjoy cooking in the spacious chef's kitchen with CAFE appliances, custom cabinetry, quartz countertops and a huge walk-in pantry. The kitchen range is the CAFE Gas Double-Oven Range with convection. Relax in the primary bedroom suite with a tremendous amount of closet space plus a custom tiled bathroom with a rain shower two lovely vanities. The two guest bedrooms on the main level are spacious, and the guest bathroom is furnished with a custom double bowl vanity with a quartz countertop. There is also a beautiful half bath on the main level adjacent to the drop zone area. You may actually enjoy doing laundry in the beautiful laundry room conveniently located adjacent to the primary closet. The finished basement is a great retreat with a wet bar and lots of cabinetry plus a huge recreation/family room. The basement offers 2 flex rooms with custom Murphy doors. For added convenience there are 2 guest bedrooms in the basement with a lovely guest bathroom which has a double bowl vanity. The home has a tremendous amount of storage throughout plus a huge, finished storage room in the basement. Enjoy the outdoors on the covered patio with a cozy fireplace patio and a private fenced in backyard. The yard has professional landscaping with a complete irrigation system. You will have comfort in knowing this home is equipped with a whole home generator. This beauty has adequate space for an inground pool as well. Don't delay schedule your personal tour today. Open house Sunday September 6th 1-4 pm.

112 Pintail Ct, 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
$609,900
4 Beds ⋅ 3 Baths ⋅ 26023336 MLS
Stunning Custom-Built Home by MCC Construction - A Must See! This beautifully crafted home by MCC Construction is sure to impress from the moment you arrive. The grand entry features an arched mahogany door and a barrel-vaulted ceiling, setting the tone for the elegance that awaits inside. Step into a spacious Great Room with gleaming hardwood floors, a cozy fireplace, and a true open-concept layout--ideal for both everyday living and entertaining. The expansive eat-in kitchen showcases custom-built cabinetry, including 48' upper cabinets, soft-close doors and drawers, and a walk-in pantry. The painted wood cabinetry is complemented by quartz countertops, a large entertaining island, and stylish plumbing fixtures. The thoughtfully designed Mud Room, located off the fully insulated 2-car garage (complete with garage door opener and remotes), provides a practical space for everyday essentials. The conditioned and insulated crawl space adds to the home's efficiency and durability. Offering 4 spacious bedrooms and 3 full bathrooms, this home delivers both comfort and functionality. The luxurious Owner's Suite features views of the backyard, a spa-like bathroom with a double vanity, tiled walk-in shower, soaking tub, private toilet room, and a generous walk-in closet. Additional bedrooms are well-sized with ample closet space, perfect for family or guests. Situated on a large corner lot--over 1/3 of an acre--this property boasts a handsome brick exterior with HardiePlank accents. Buyers may still have the opportunity to make selections on finishes not yet finalized. Located in desirable Halfhill Estates, just minutes from the US-27 Bypass, this hard-to-find new construction home offers convenience, craftsmanship, and comfort. Don't miss your chance to own this exceptional home--schedule your showing today!

134 Zane Ln, Nicholasville
$277,000
2 Beds ⋅ 2 Baths ⋅ 26022395 MLS
Opportunity Knocks! Rare chance to own a maintenance free condo in this perfect community of Bethal Pointe. Located in the quaint town of Wilmore KY this property checks all the boxes. Boasting an outstanding HOA that covers so much and pays for your outside maintenance, lawn care, blacktop roads, swimming pool, club house, exterior insurance, sewer, water, trash and snow removal that way you can enjoy the worry-free lifestyle that you have always wanted. This specific condo is in an outstanding location, and you will love the private front patio that's shaded even on those hot summer days. Inside the owner has added all new luxury vinyl flooring, fresh paint and it's in move-in-condition. This unit is the perfect size and features nice white cabinets, 9-0 ceilings and even a gas fireplace for those cold winter nights. If you're dreaming about living in an outstanding community where neighbors look out for each other, you might have just found it. Enjoy the neighborhood swimming pool just steps away from your condo and then share some food at the clubhouse with some neighbors at one of the community potluck dinners. This place is truly a gem and offers easy access to the heart of Wilmore and a very short distance from Asbury University and Seminary! Hurry do not miss this Rare Opportunity! See Today!

110 Academy Dr, Wilmore
$424,900
3 Beds ⋅ 2 Baths ⋅ 26021292 MLS
This is your opportunity to have it ALL ! All brick and all one level. Welcome to your new home. Built in 2025, this home is practically brand new. Immediately you are welcomed into the great room, which allows you to enjoy both the kitchen and the living room. The kitchen has an incredible kitchen featuring cabinets with soft close drawers, granite counter tops, a tile backsplash, kitchen island with an overhang and a huge pantry. The living room is large enough for any sectional you could want. The primary suite is large with an ensuite bathroom. The primary bath offers a double bowl vanity and a tile shower. The split bedroom design offers 2 remaining bedrooms on the opposite side of the house with a bathroom in the hall to share. This home was custom built by the owner who made several adjustments to fit his needs, which will be passed on to you. The garage is oversized and will allow you to park almost any vehicle. There is also additional driveway space allowing for more parking and turning around in the driveway. If you are looking for the most affordable home in Halfhill Estates, you have found it. This is your opportunity and it won't last long. Call immediately to see this one for yourself.

2031 Shun Pike, Nicholasville
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