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$188,500
3 Beds ⋅ 1 Baths ⋅ 26006789 MLS
Property qualifies for USDA zero dollar down financing! Great Opportunity for First-Time Homebuyers! This charming 3-bedroom, 1-bath home features beautiful hardwood floors, an updated kitchen, and a fenced backyard perfect for relaxing, entertaining, or pets. Move-in ready and full of value, this is a wonderful opportunity to own a home with both character and convenience. Schedule your showing today!

41 Hiawatha Trl, Winchester
$110,000
22024072 MLS
Looking for a place to build a Upscale home in Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

150 Duclair Dr, Winchester
$225,000
3 Beds ⋅ 2 Baths ⋅ 26011961 MLS
Remodeled and move-in ready! Conveniently located in downtown Winchester just minutes from Main Street and I-64, this charming home offers the perfect blend of character and modern updates. Major improvements include a near complete replacement of the heating, plumbing, and electrical systems, giving buyers peace of mind for years to come. Inside, you'll find all new flooring throughout, a beautifully updated kitchen featuring stainless steel appliances, a gas range, pantry, and plenty of space for cooking and entertaining. The home offers a primary suite, two additional bedrooms, an additional full bath, and a large utility room with extra storage and functionality. Outside, the 20x24 detached garage with electric is a rare bonus and ideal for carpentry projects, woodworking, hobbies, a workshop, home gym, storage for recreational equipment, or even the perfect space for car enthusiasts and DIYers. Enjoy small-town charm with quick access to shopping, dining, and interstate travel in this thoughtfully updated property ready for its next owner!

14 Cook Ave, Winchester
$67,500
26005958 MLS
Unique triangular shaped lot in a wooded rural setting, interesting opportunities for privacy in a beautiful area of Clark County where you can enjoy the outdoors and create memories galore.

250 Spencer Ln, Winchester
$100,000
22024121 MLS
Looking for a place to build a Upscale home in Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

225 Jacob Ct, Winchester
$515,000
5 Beds ⋅ 3 Baths ⋅ 26007022 MLS
Brick ranch with 3 upstairs bedrooms and 2 bedrooms in your mother in law suite and full finished basement, complete with kitchen. 2 gazebos with one attached to walk out porch over looking almost 3 acres of beautiful land. Attached 2 car garage and detached 2 car garage. Barn/workshop included, along with another metal building for storage.

110 White Conkwright Rd, Winchester
$375,000
3 Beds ⋅ 3 Baths ⋅ 26013780 MLS
Just a 20-second golf cart ride to the Winchester Country Club driving range! Built in 2024 and upgraded throughout, this beautiful 3-bedroom, 2.5-bath home offers modern style, functional living space, and a prime location. The open-concept main level features a spacious living room, kitchen, and dining area designed for both everyday living and entertaining, complete with granite countertops in the kitchen and baths, a deep farmhouse sink, pantry, and stainless appliances. Upstairs, you'll find a generous primary suite with a private bath and walk-in closet, along with two additional bedrooms and a full guest bath. Luxury vinyl plank flooring runs throughout the home, while accent wallpaper in multiple rooms adds warmth, personality, and a custom feel. Recent owner upgrades include a privacy fence, landscape lighting and new shrubs, upgraded stair treads, a concrete sidewalk, and additional attic flooring with a folding attic ladder for convenient storage. The home's attractive exterior combines clean modern lines with shake-style architectural accents, creating great curb appeal. Enjoy nearby golf course views and the convenience of country club living without being directly on the course. Additional features include a 2-car attached garage, crawlspace foundation, and no HOA. With modern construction, quality finishes, and numerous owner-added improvements, this move-in ready home is ready for its next owners to enjoy.

309 Gallahadion Ct, Winchester
$600,000
26008236 MLS
Discover an exceptional opportunity for retail investment in the thriving Winchester area. Zoned B-4, this versatile property offers a wide array of possibilities for retail development, providing a strategic location for businesses seeking to establish a prominent presence. With its prime zoning and desirable position within the Winchester area, this property presents a compelling prospect for retail investors looking to capitalize on the region's commercial potential.

722 Colby Rd Unit #2, Winchester
$1,110,000
25505201 MLS
Corner lot behind Rural King with proximity to the Bypass, multiple area schools, the hospital, Interstate 64, and the Bert T. Combs Mountain Parkway.

440 Shoppers Dr, Winchester
$324,900
3 Beds ⋅ 2 Baths ⋅ 26014053 MLS
If you love to entertain and are looking for a cozy home that is move in ready, you don't want to let the one pass you by! Includes 3 bedrooms and two full baths this home has it all. Equipped with a primary bedroom suite with spacious bathroom and walk in closet. This home has beautiful hardwood floors in kitchen living and dining areas. In the gallery kitchen you will find granite countertops, new stainless steel dishwasher,refrigerator and stove. Great curb appeal, covered back porch, with privacy fencing, two storage sheds, large driveway, lots of updates throughout and more.

8 Monroe Ave, Winchester
$110,000
22024095 MLS
Looking for a place to build a Upscale home in Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

230 Duclair Dr, Winchester
$645,000
4 Beds ⋅ 3 Baths ⋅ 24025577 MLS
Welcome Home to the Claiborne Floor Plan by CP Builders. This stunning 4-bedroom, 2.5-bathroom home offers a luxurious and spacious living experience. The first floor features a magnificent primary suite complete with a spacious ensuite bathroom, a walk-in closet, and direct access to the backyard. The open floor plan seamlessly connects the living, dining, and kitchen areas, creating a warm and inviting atmosphere. The gourmet kitchen boasts a large island, perfect for entertaining, and a walk-in pantry for ample storage. A cozy fireplace with gas logs adds a touch of warmth and ambiance to the living room. The first floor also includes a dedicated dining room, a study perfect for working from home, a separate laundry room, and a convenient half bath for guests. Upstairs, you'll find three additional generously sized bedrooms and a two full bathrooms, providing ample space for family and guests. The two-story living room creates an impressive and airy feel throughout the home. Experience the joy of building your dream home with CP Builders.

106 Bella Shae Way, Winchester
$110,000
22024074 MLS
Looking for a place to build a Upscale home in Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

160 Duclair Dr, Winchester
$413,000
3 Beds ⋅ 3 Baths ⋅ 26009517 MLS
Welcome to this beautiful brick ranch on a basement in Hampton Manor. The double front doors open into a large entry way where you will find a living room with large windows allowing for great lighting. The dining room has a fireplace and exposed beams. The kitchen features updated appliances and granite counter tops with an island and a pantry. The sink overlooks the back yard that backs up to a wooded area. The 2 car garage is right off the kitchen allowing for easy accessibility to bring your groceries in. The primary is on the first floor and has an en-suite with a separate sink area from the shower and toilet. There are two other bedrooms and another full bath on the first floor for guests. In the basement you will find the family room and another gas fireplace. There is enough room to have one corner of the basement be an office if needed. You will also find another half bath and utility room on the lower level. The back side of the basement has a large unfinished area with tons of possibilities. The basement family room has walk up/walk out access to the back yard patio where you will find an above ground pool, greenhouse, play set and trampoline (all can be conveyed if needed).

20 Edgewood Dr, Winchester
$154,900
26013322 MLS
Great opportunity to own a prime lot in the exclusive Thoroughbred Estates, Winchester's most exclusive subdivision. Located between Winchester and Lexington this location is close to shopping, schools, hospitals and interstates. If your tired of living on a postage stamp lot then this lot is for you. Select your dream house plan and select your builder before it's too late.

750 Craig Xing Unit Lot #7, Winchester
$775,000
5 Beds ⋅ 3 Baths ⋅ 26007545 MLS
Dreaming of wide-open spaces and country charm? This beautiful 16-acre property in Clark County offers the perfect blend of comfort and functionality. The stately brick home provides generous living space with classic appeal, offering endless potential. With five bedrooms and three full baths, the home accommodates a variety of living arrangements, whether you need space for guests, a home office, or simply room to spread out. The generously sized living area opens seamlessly into the dining area, creating a natural gathering space for those family gatherings or functional for everyday living. With a 42 x 40 metal barn, open pastures and scenic surroundings, this property is ideal for equestrian enthusiasts, hobby farmers, or anyone looking to escape the hustle without sacrificing convenience. Enjoy peaceful mornings, breathtaking sunsets, and room to roam—all within easy reach of Lexington. The home is ready for its next owner to move in and make it their own, Seller is offering a generous flooring allowance with an acceptable offer providing the opportunity to refinish the existing hardwood floors and replace carpeting. Buyer to verify all aspects of the property and school districts.

465 Morris Rd, Winchester
$550,000
23015569 MLS
Ideally located along the heart of Bypass Road (ADT: 24,801) in Winchester, Kentucky between and surrounding Kroger and Walmart shopping centers. These lots are offered as 1+ acres and may be subdivided. Winchester, KY is the county seat of Clark County, KY and is part of the Lexington-Fayette KY Metropolitan Statistical Area, and is supported by such industries such as Amazon, Ale-8-One, and Catalent Pharmaceuticals. Second Row Lots conveniently located along residential density while being visible from the Bypass. Conceptual Plans have been created which display potential uses of up to 22,800 SF as retail box. Would be a great location for retail, office, storage, and mixed use development. Conceptual Development Plan: https://www.kcrea.com/files/property/6900000/6902843/25814078_2020___Conceptual_Development_Plan_Lots_3.pdf

609 Bullion Blvd Unit 3A, Winchester
$2,750,000
8 Beds ⋅ 8 Baths ⋅ 26009631 MLS
Welcome to 4664 Lexington Road—a magnificent private estate on 35 rolling acres of pristine Kentucky countryside that feels worlds away, yet sits just minutes from the charm of Winchester and the vibrancy of Lexington. A stately stone entry welcomes you down a graceful, winding driveway to a sweeping circular drive, leading to a grand 13,000+ square-foot residence built in 1997 with timeless elegance and generous proportions. Inside, the 8-bedroom, 7.5-bath home offers expansive living spaces bathed in natural light, refined finishes, and classic architectural details—perfect for both intimate family moments and large-scale entertaining. A fully finished basement adds exceptional flexibility for recreation, additional living quarters, or extended gatherings. Outdoors, the property continues to impress with sweeping valley views, open pastures and mature wooded areas. Enjoy the private pool as a true retreat. Additionally, the property is complemented by a classic tobacco barn and additional shop space ideal for storage, hobbies, equestrian use, or agricultural pursuits. Zoned PD (Planned Development), this estate presents rare versatility and significant upside—whether envisioned as a forever family home, a multi-generational retreat, a private equestrian estate, or a thoughtfully planned development opportunity. Privacy is unparalleled, yet convenience is effortless, with easy access to world-class horse farms, bourbon trails, and the cultural amenities of the Bluegrass Region. This is more than a home—it's a legacy property where luxury living, natural beauty, and gracious Kentucky living come together in perfect harmony, delivering exceptional value and endless possibilities.

4664 Lexington Rd, Winchester
$235,000
25501332 MLS
6.08 acres settled in Clark County with access from both Privacy Ln and Little Stoner Rd. This property boasts a 30x56 with 10 foot wall Kentucky Steel Truss building with concrete floors, gas and wood burning heat, full bath, and a car lift. Additionally, there is a barn with a 3 bay shed attached.

190 Privacy Ln, Winchester
$1,350,000
23015568 MLS
Ideally located along the heart of Bypass Road (ADT: 24,801) in Winchester, Kentucky between and surrounding Kroger and Walmart shopping centers. These lots are offered as 1+ acres and may be subdivided. Winchester, KY is the county seat of Clark County, KY and is part of the Lexington-Fayette KY Metropolitan Statistical Area, and is supported by such industries such as Amazon, Ale-8-One, and Catalent Pharmaceuticals. 155 April Way consists of 3 acres positioned along April Way and Colby Rd, two major connector roads within the city of Winchester. Strategically positioned between commercial traffic and uses along Bypass Rd, and high residential density behind.

155 April Way, Winchester
$165,000
2 Beds ⋅ 2 Baths ⋅ 26001738 MLS
Welcome to this charming river front house. Step out your back door and you are immediately at the river. Open floor plan with a wood burning fireplace. Metal cabinets and epoxy floors on the first level are designed to survive in case of a flood. First floor bedroom with enough room for a King sized bed. Upstairs you will find another bedroom and a half bath. Sip your morning coffee on your back patio area or deck over looking the Kentucky River. There is a large carport for your truck and enough room for a boat as well. The large lot will accommodate a fire pit where you can gather with friends and family. This property is in a flood zone. This property was used as a rental and an air b&b. Make it your own or rent it out, the possibilities are endless.

1494 Amster Grove Rd Rd, Winchester
$100,000
22024133 MLS
Looking for a place to build a Upscale home in Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

129 Duclair Dr, Winchester
$724,950
2 Beds ⋅ 3 Baths ⋅ 25507944 MLS
Hunter's Paradise! This beautiful 85 acre farm is nestled in the heart of Clark County. Wildlife is abundant as you travel throughout the property. The home is very spacious with a full mother in law suite. Entertain friends at the full bar, while enjoying the wood burning stove. A functioning greenhouse expands the possibilities for year round gardening. If you are looking for little piece of Heaven in the country this is your place. Only minutes from the Mountain Parkway, downtown Winchester, and Mount Sterling. Restaurants, shopping, golf courses, and several amenities are also just a short drive away.

455 Davis Ln, Winchester
$882,000
26011486 MLS
NOW SELLING PHASE ONE: 7 of the 12 Buildable Lots (minimum lot is 9600+ sqft) of PHASE ONE of Deerlawn's Development located at 2395 Paris Rd (Parent Listing). Earmarked as Winchester, Ky's most anticipated residential development consisting of an ambitious 274+-acre expansion formerly known as the well-established Royal Oaks/Plantation neighborhoods, Phase One has 12 lots ready for you to build your New Kentucky Home. The developer is currently finalizing the restrictions so they are not available for distribution. However, new restrictions will still incorporate the following: 80% brick/stone exterior, Roof pitch requirements, Minimum 1,600 sq ft for a ranch, 1800 for a One-Half Level, 2100 Two Story. Development lot sizes require minimum lot is 9000 sq ft and current development plan has the smallest lot at 9600 sqft. Positioned off I-64 at Exit 96 across from the rapidly expanding Industrial Park, Deerlawn is a master-planned community offering 438 future single-family homes, and additional acreage available for 8 duplexes and 48 townhomes, meeting the region's demand for quality and attainable housing. Phase Two and Three begin in December with 34 buildable lots expected completion by Spring 2026 Approved development plan in place with Clark County. Additional Phases continuously following with additional buildable lots. Located within 20 miles to Lexington's Hamburg area, Deerlawn sits at the center of Clark County's growth corridor. With $100M in infrastructure improvements completed and the EPA Consent Decree lifted in 2024, the path is clear for accelerated residential and economic expansion.

7 Plantations Dr, Winchester
$785,000
4 Beds ⋅ 3 Baths ⋅ 25000149 MLS
Introducing the Highland, an elegant all-brick ranch home offering 4 bedrooms and 2.5 full baths in a thoughtfully designed split-bedroom layout. The spacious primary suite is a true highlight, featuring a luxurious tile shower, separate soaking tub, double vanities, and a large walk-in closet. The open-concept kitchen flows seamlessly into the great room, creating the perfect space for entertaining, with a gas log fireplace, oversized island, and a generous walk-in pantry. This kitchen also features adjacent dining area. The Highland also offers a separate, spacious utility room, and a 2-car attached garage for convenience. Nine-foot ceilings and luxury vinyl plank flooring throughout add to the home's modern appeal. With its stunning double entry doors and stylish curb appeal, the Highland blends comfort, functionality, and timeless design into one perfect home. This desirable lot also includes an unfinished walkout basement, offering endless possibilities for expansion or customization. Experience the perfect blend of style and practicality in the Highland floor plan. Come build the Highland in Mallard Cove with CP Builders!

425 Alexis Way, Winchester
$899,000
3 Beds ⋅ 3 Baths ⋅ 26013217 MLS
MIDNIGHT ON THREE - Luxury Living Meets Convenience in Clark County KY Nestled on 3.054 beautifully maintained acres, this stunning home was thoughtfully designed with quality and elegance in every detail. Just 2 minutes from Exit 10 on the Mountain Parkway, this extraordinary custom-built estate offers a rare combination of privacy, craftsmanship, and accessibility. From the moment you arrive, the striking exterior, expansive covered porches, and picturesque setting create an unforgettable first impression. Inside, soaring ceilings, walls of windows, and abundant natural light showcase the home's exceptional design and create a warm, inviting atmosphere. The open-concept living space is anchored by a floor-to-ceiling stone fireplace and flows seamlessly into a designer kitchen featuring custom cabinetry, premium countertops, upscale fixtures, and a large gathering island perfect for entertaining. The luxurious primary suite offers a private retreat with a spa-inspired bath, oversized walk-in shower, soaking tub, and custom finishes throughout. Every room reflects the superior craftsmanship and attention to detail that set this home apart from ordinary construction. Whether you're enjoying morning coffee on the screened porch, hosting guests in the expansive living areas, or simply taking in the peaceful surroundings, this property delivers a lifestyle of comfort and sophistication. The versatile upper-level loft provides additional living space ideal for a media room, office, or guest retreat. Situated close to one of Eastern Kentucky's most desirable areas, this property offers quick access to Lexington, Winchester, and the Red River Gorge region while maintaining the privacy and serenity of a luxury country estate. Exquisite custom construction. Premium finishes. Exceptional location. For buyers seeking a truly remarkable home where quality, style, and convenience come together, this Clark County masterpiece is a rare opportunity. Luxury, privacy, and craftsmanship—without compromise.

330 Spencer Ln, Winchester
$110,000
22005014 MLS
Lot # 30 contains 2.058 acres of gently rolling land perfect for your new home. This is a rare opportunity to own a piece of western Clark County real estate in the sought-after McClure Road area. Thoroughbred Estates is Winchester's newest upscale development containing 33 lots from 2 acres to nearly 7 acres. Lots are located just minutes from Winchester and Lexington.

1185 Craig Crossing Rd, Winchester
$225,000
26011064 MLS
8+ Acres of Prime land available in the Heart of the Bluegrass! Whether you're looking to design your ideal homestead or simply building your custom country home with plenty of space to roam, this property offers an optimal blend of space, beauty, tranquility, and convenience. Enjoy peaceful rural living with open skies and scenic countryside views, surrounded by picturesque farms and a nearby vineyard that add to the charm of the area. The flat terrain provides some ideal options for building sites with plenty of room for gardens, livestock, barns and recreational use. Located just a short drive from Lexington, Richmond and historic downtown Winchester, you'll enjoy country living without sacrificing city amenities. Bring your plans and make it your own!

5127 Combs Ferry Rd, Winchester
$445,500
3 Beds ⋅ 3 Baths ⋅ 26009944 MLS
This is a perfect home for EVERY season.....enjoy multiple, interior gathering spaces and the glow and warmth of either the L R or Dining Room fireplace on the main level or the coziness of the mesmerizing fireplace in the lower level family room during the winter. Watch the backyard come alive with rich and lush vegetation during the Spring from the large, glass walled sun room. For Summer, tons of options await you with the covered front porch, the partially covered back deck or escape to the seclusion of the covered, separate structure at the back. Both the front and back yards are landscaped with many mature trees and perennials that require little attention during Spring, Summer and Fall. Inside, this expansive floor plan packs a lot of punch with a number of interior spaces with an easy flow. The wide entry hall foretells of large room sizes and fresh, neutral paint throughout. The newly renovated kitchen with light wood cabinets is timeless in it's appeal and the adjacent breakfast area is full of natural light. Another handsome fireplace in the next space, with built in shelves could easily function as a D R or Den and the sunroom gives a panoramic view of the beautiful back yard. Three bedrooms and two baths round out the first floor. The lower level features a massive two car garage, half bath, laundry and a large Family Room/Man Cave space for quiet reading or lively entertaining with a third fireplace. So many beautiful options await you in this wonderful home, located in a quiet, attractive, safe and neighborly enclave.

42 Mockingbird Valley Rd, Winchester
$465,000
3 Beds ⋅ 2 Baths ⋅ 26011126 MLS
This 3 bedroom 2 bath ranch home is tucked away in a beautiful wooded area of Clark County. It is sitting on over 10 acres of land that would be great for livestock or hunting. It is just minutes from historic downtown Winchester. The property is also a short drive to retail shops, restaurants, and other amenities. Come take a look at the beautiful view from the front porch of this home in the country.

287 Logan Lick Rd, Winchester