Winchester Real Estate | Winchester Waterfront Properties for Sale

NOW SELLING SFH Buildable Lots of PHASE ONE: 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. New restrictions will 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.

Lot 4 Plantations, Winchester

$128,800

26008587 MLS

This exceptional 2.3 acre homesite offers the perfect canvas to bring your vision to life. With ample space, a prime cul-de-sac setting, and stunning surroundings, it's an ideal opportunity to create the custom home you've always wanted. Located in The Reserve, one of Winchester's premier subdivisions, this property boasts scenic daytime views and unforgettable sunsets each evening. Enjoy the perfect blend of privacy and convenience with quick access to shopping, dining, schools, and I-64. Don't miss your chance to own the largest lot in the neighborhood. Schedule your visit today!

110 Knox Ct, Winchester

$340,000

4 Beds ⋅ 5 Baths ⋅ 26010324 MLS

Investment opportunity in the heart of Winchester! Brick Triplex featuring a main level, high visibility commercial space with Lexington Avenue frontage and two apartments on the upper level! Each apartment has two bedrooms, one bath. One unit has been recently remodeled, the other has potential for value add. The flexible commercial space contains 3 half baths. Laundry hook-ups in all 3 units! Basement for extra storage room with freight elevator. Two new HVAC units and a new roof within the last 2 years! Approximately 16 parking spaces.

502 W Lexington Ave, Winchester

$325,000

26014051 MLS

******PRICED BELOW APPRAISAL & MOTIVATED SELLERS****** Whether you're looking for a large residential home, investment opportunity, business potential, or a combination of uses, this property is ready to fit your vision. Featuring 5 bedrooms, 4 baths, soaring 10 foot ceilings, and a welcoming front porch, this unique property blends character, space and versatility. Generous room sizes, timeless charm, and flexible living spaces make it ideal for multi-generational living, rental income opportunities, or for a great work setup. Opportunity with unlimited potential.

410 W Lexington Ave, Winchester

$355,000

1 Beds ⋅ 2 Baths ⋅ 26012322 MLS

Home listed as one bedroom while unofficially has 3 but 2 of them are interior rooms without windows. ( Owners Now Offering to pay up to $5,000 in closing cost and pre-paids on behalf of buyers). Tired of the honking horns , congested traffic, sirens of town living and dreaming of country living, your own slice of paradise? Maybe raising your own garden , owning chickens , goats, horses , whatever you always dreamed of. Maybe just kicking back on the wrap around porch watching the chickens peck. This really is an amazing property and you will fall in love with all the bells and whistles like the beautiful soaking tub, 2 walk in showers, huge kitchen island, large primary bedroom and bath, stainless steel appliances. It practically a new house , the front portion of the house where the living room , hall, primary bedroom were all built new in 2020 . All the wiring , plumbing , insulation, flooring , drywall has been replaced since 2020. Home is also very conveniently placed just minutes from exit 10 on the Mountain Parkway between, Winchester and Clay City. Dont let anyone beat you to it , this is a real jewel. Porch swing belonged to owners great grandmother and does not convey.

3359 Trapp-Goffs Corner Rd, Winchester

$550,000

3 Beds ⋅ 3 Baths ⋅ 24025578 MLS

Welcome Home to the Winchester Floor Plan by CP Builders. This elegant ranch home features all-brick construction, a welcoming front porch, and a two-car garage. Step inside and be greeted by soaring 9-foot ceilings and a spacious open floor plan. The split bedroom design offers privacy and comfort, with a luxurious primary suite boasting an ensuite bathroom and a walk-in closet. Enjoy easy maintenance with luxury vinyl plank flooring throughout the home. The heart of the home is the spacious great room, complete with a cozy gas log fireplace, perfect for gathering with loved ones. The well-appointed kitchen features a large island, ideal for both cooking and entertaining. Additional features on the first floor include a full bathroom, a convenient half bath, and a separate laundry room for added convenience. Step outside onto the back patio and enjoy the fresh air and sunshine. Let's build your dream home and make the Winchester Floor Plan yours!

107 Bella Shae Way, Winchester

$699,000

26004697 MLS

Operated for over 20 years as a physician's office this two-story building features a "ready to go" office on the main floor with two large apartments on the second floor with walkup, outside entry. The entire structure is on an unfinished basement perfect for storage and access to the mechanical systems. There is also a detached 3-bay garage for parking and storage as well as an asphalt parking lot with more room for more than 25 vehicles.

218 S Maple St, Winchester

$2,999,000

6 Beds ⋅ 5 Baths ⋅ 25507353 MLS

Some properties are special simply because of the story behind them. This 150 acre farm with 3,168 feet of road frontage in Winchester has been cared for by the same family since 1803, and it's now being offered for sale for the very first time. The land is classic Kentucky countryside, rolling pastures, peaceful water, and wide open views in every direction. Four ponds and a gently flowing creek bring both beauty and function to the farm, while four barns and two storage sheds make it ready for cattle, horses, or anyone wanting a true working farm. There are two homes on the property, offering flexibility for extended family, guests, or farm operations. Whether you dream of continuing its farming legacy, creating a private retreat, or investing in a truly special piece of Kentucky land, this is the kind of place that rarely becomes available. Opportunities like this don't come around often. This farm has been part of one family's story for over two centuries, now it's ready for its next chapter.

3049 Ironworks Rd, Winchester

$78,500

26011487 MLS

NOW SELLING SFH Buildable Lots of PHASE ONE: 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. New restrictions will 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.

Lot 3 Plantations, Winchester

$825,000

3 Beds ⋅ 3 Baths ⋅ 24025579 MLS

Welcome Home to the Park Place Floor Plan by CP Builders. This elegant ranch home features all-brick construction and a thoughtfully designed split bedroom layout for maximum privacy. The open floor plan seamlessly connects the living, dining, and kitchen areas, creating a warm and inviting atmosphere. The spacious kitchen is a chef's dream, boasting a large island, a convenient pantry, and a cozy breakfast nook. The luxurious primary suite offers a private retreat with an ensuite bathroom and a walk-in closet. Every bedroom in this home features a walk-in closet, providing ample storage space for the whole family. Additional features on the first floor include a formal dining room, a dedicated study perfect for working from home, a half bath for guests, and an additional full bathroom. This desirable lot also includes an unfinished walkout basement, offering endless possibilities for expansion or customization. Make the Park Place your dream home. Reach out today to schedule a consultation with our experienced team and bring your vision to life.

111 Bella Shae Way, Winchester

$150,000

26008075 MLS

Parcel 4 in the photos. This 2.774 acre lot is available on Colby Road just 1.5 miles from the Winchester Bypass. No building restrictions other than no manufactured housing and a paved driveway must be completed within a year of finishing a residence.

3385 Colby Rd, Winchester

$670,000

3 Beds ⋅ 2 Baths ⋅ 24025580 MLS

Introducing the Hampton, a beautiful all-brick ranch home. This 3-bedroom, 2-bath split-bedroom design offers both privacy and comfort. The spacious primary suite is a true retreat, featuring a luxurious ensuite with double vanities, a walk-in shower, and dual walk-in closets. The open-concept kitchen and great room are perfect for entertaining, highlighted by a gas log fireplace, a large kitchen island, and a generous walk-in pantry, along with a convenient butler's pantry for added storage and prep space. Nine-foot ceilings and luxury vinyl plank flooring throughout add a touch of elegance, while the separate utility room offers practicality. The additional two bedrooms also include walk-in closets. With a formal dining room, unfinished walkout basement, and a two-car garage, this home combines stunning curb appeal with modern functionality. Come build your dream home in Mallard Cove neighborhood!

113 Bella Shae Way, Winchester

$110,000

22024065 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.

120 Duclair Dr, Winchester

$137,500

26006848 MLS

Build your dream home in the stunning ESKIPPAKITHIKI OVERLOOKS! Looking for your next investment? This 3.940 acre parcel offers unlimited potential-whether you dream of building or simply holding land as it grows in value. Offering unparalleled views of a serene, natural setting. Perfect for a private retreat or family estate, this property invites you to design your ideal lifestyle surrounded by the beauty and tranquility. Don't miss your opportunity to own prime land with unmatched potential

150 Spencer Ln, Winchester

$1,850,000

20101924 MLS

17.87 Acre farm available for sale. Ideal location for redevelopment. Gently rolling topography. Corner lot with excellent visibility. Water, electric, sewer, gas and telecommunications available. Conveniently located near RD Campbell Junior High School, George Rogers Clark High School & Winchester Country Club. Located 3 miles south of Interstate 64. Signalized corner lot at Boonesboro Rd. & Bypass Rd. Easily accessible to nearby retailers, restaurants & residential. Winchester is the county seat of Clark County, KY. This growing city is part of the Lexington-Fayette, KY MSA. Local employers include Amazon, Ale-8-One, and Alltech.

1509 Boonesboro Rd, Winchester

$1,200,000

16 Beds ⋅ 16 Baths ⋅ 26007993 MLS

You won't want to miss adding this income-producing apartment complex to your portfolio. This property is comprised of 16 one-bedroom/one-bathroom apartments with 100% occupancy. Complex is conveniently located in downtown Winchester and only 20 minutes from Lexington via easy highway access. The building sits on a 0.34 acre lot with 20+ parking spaces. Property has several updates including roof replacement in 2022, new siding in 2023, and 6 of the AC units were replaced in the last three years. The main electrical service mast was replaced in 2023, and all 100-amp breakers were replaced in 2025. Most units have been updated with LVP flooring.

16 Linden Ave, Winchester

$42,500

26005419 MLS

105 Bella Ct, Winchester

$110,000

22024114 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.

125 Jacob Ct, Winchester

$139,900

3 Beds ⋅ 1 Baths ⋅ 26007798 MLS

3BR/1BA | Winchester, KY Affordable single-family homes are hard to come by at this price — here's your chance. This cozy 3-bedroom, 1-bath home in Winchester sits on a generous lot with a large backyard, long driveway with plenty of parking, a welcoming covered front porch, and accessible front entry with both steps and a ramp. it's efficient and easy to maintain — and don't let the square footage fool you. A huge walk-in crawl space underneath the home offers exceptional storage that most homes twice the size don't have. The big-ticket items are handled: a brand new roof was installed in 2024, giving you peace of mind for years to come. Currently tenant occupied — ideal for an investor looking for immediate cash flow, or a future owner-occupant planning ahead.

19 3rd St, Winchester

$1,750,000

23021742 MLS

101 S. Main Street is a fully-restored historic Opera House in the heart of Downtown Winchester. Now functioning in a multiple use capacity, including gallery space, 7-years-running successful restaurant space, wedding event and reception space, and office space. No detail was overlooked in this extensive renovation, now inclusive of multiple commercial kitchens, interior elevator, gracious entertainment spaces, and an abundance of old-world charm through hardwood floors, large windows, exposed brick, and functioning fireplaces. In fact, the Opera House renovations earned the Clyde Carpenter Adaptive Reuse Award from the Bluegrass Trust Historic Preservation Comm. This offering is extremely flexible in that a new owner can step in and operate the same uses already in place, including Lease Back potential from Loma's which is owner occupied, or use the flexible layouts for its own preferences. It is also in the Opportunity Zone, and Downtown Winchester KY offers numerous grants for both renovations and business development should a buyer wish to participate. *Business purchase is not included in the real estate offering. Property Highlights: -Home of the successful and delicious Loma's at the Opera House restaurant and bar, and The Winchester Opera House Ballroom -Ideally located in the heart of Downtown Winchester -The property benefits from the City of Winchester's investment in neighboring High Side Improvement Project with included $5.5 million invested in new angled parking, new sidewalks and added ramps, making the downtown area more accessible as well as 13 new high-end apartments with 10 more in development.

101 S Main, 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

$219,000

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

$359,000

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

$319,900

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

$42,500

26005320 MLS

The restictions state that if it is a ranch plan, there is a minimun of 1300 sq ft. It it is a 1 1/2 story or two story then 1800 sq ft will be required. A two car garage must be attached. Developer will need to approve plans before starting construction This lot is ideal for a walkout basement. Perfect setting for watching the sunsets

108 Dorset Ln, 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

$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

$699,000

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

$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

$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

$435,000

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

$925,000

1805484 MLS

Great location just off exit 96 on I-64 and easy access to the Mountain Parkway. Only 15 minutes from I-75. Located near the entrance to the Winchester Kentucky Industrial Park. 3.774 flat acres to build your next business location.

300 Rolling Hills Ln, Winchester

$2,999,000

6 Beds ⋅ 5 Baths ⋅ 25507142 MLS

Some properties are special simply because of the story behind them. This 150-acre farm with 3,168 ft of road frontage in Winchester has been cared for by the same family since 1803, and it's now being offered for sale for the very first time. The land is classic Kentucky countryside, rolling pastures, peaceful water, and wide open views in every direction. Four ponds and a gently flowing creek bring both beauty and function to the farm, while four barns and two storage sheds make it ready for cattle, horses, or anyone wanting a true working farm. There are two homes on the property, offering flexibility for extended family, guests, or farm operations. Whether you dream of continuing its farming legacy, creating a private retreat, or investing in a truly special piece of Kentucky land, this is the kind of place that rarely becomes available. Opportunities like this don't come around often. This farm has been part of one family's story for over two centuries, now it's ready for its next chapter.

3049 Ironworks Rd, Winchester

$49,500

25005098 MLS

Choose your preferred builder to construct your dream home in Mallard Place. Located in a quiet cul-de-sac at the rear of the subdivision. Only a 20 minute drive to Hamburg/Lexington and only a 5 minute drive to the Winchester Bypass. Enjoy the serenity of living in a private setting AND the convenience of being close to schools, shopping and I-64 and I-75.

204 Wigeon Ct, Winchester

$150,000

22004993 MLS

Lot # 14 contains 4.21 acres of gently rolling land with small stream 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.

1030 Craig Crossing Rd, Winchester

Winchester Waterfront Properties for Sale

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Amanda Marcum - MARCUMsold

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