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$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
$219,000
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
$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
$188,500
26005457 MLS
Great opportunity to develop/ build on 12+ acres. The property has three street stubs adjoining it. Three different concepts are included under documents. They are- R-1E, 4000 sq. Ft lots for 80 lots R-4- 14 Duplexes and 6 4plexes for 52 units R-1D - 6000 sq. Ft. Lots for 41 lots. Utilities are to the property and sewer availability should not be an issue.

155 Spring Ridge Way, Winchester
$42,500
26005413 MLS
Wowser! Looking for a lot that backs up to greenspace and will NOT have another home on one side? Here it IS! This may be just what you're looking for. Originally, the street was supposed to connect, but due to the changes in grade, this won't be happening! Plus, with the way the lot sits, you can enjoy many beautiful sunsets. It's a hidden gem just waiting for you to find it! The home to be built here must have a minimun of 1000 sq ft. with a two car garage attached. Developer will need to approve plans before starting construction

113 Mayfair Ct, Winchester
$10,000
25501219 MLS
Discover the potential of this spacious 0.17-acre residential property nestled in a neighborhood community on clear and level vacant lot located in a Cul-de-sac of Lincoln Park Subdivision. This could be an investment opportunity as well, for ideal savvy investors looking to diversify your portfolio this property would be perfect for building a custom home, holding for future value, or develop now.

117 4th St, Winchester
$229,000
3 Beds ⋅ 1 Baths ⋅ 26013434 MLS
Welcome to a well maintained 3 bedroom 1 full bath home that has been lovingly cared for by only two owners since 1962. Recent updates include new flooring and completed repairs, makiing this property ready for a new owner, while preserving its timeless character. Beautiful hardwood floors add warmth and charm throughout the home. Enjoy relaxing or entertaining on the comfortable spacious patio perfectly sized for gatherings. The brick fireplace with gas logs, located in the living room, adds a cozy ambience on cool evenings. One of the property's standout features is its prime location backing directly to Legacy Grove Park complete with a private gate providing conveninent park access. This unique setting offers addttiional outdoor space, scenic views and a peaceful atmosphere right in your own backyard. . This is a wonderful opportunity to call a well cared for property with an abundance of charm your very own.

30 Virginia Ave, Winchester
$299,900
4 Beds ⋅ 3 Baths ⋅ 26015653 MLS
Very motivated sellers, Get here first, make an offer on this 4 bedroom, 3 bath, 1 1/2 story home, 2 car garage, showroom fresh condition, vaulted ceiling, hardwood floors, tile, carpet, deck, nice back yard, call today to view.

209 Connie Ln, Winchester
$270,000
20111867 MLS
Visibility, Access, Utilities on site per seller/per plat buyer to verify, zoned B-3. .84 acres located and visible at I-64 exit 96, buyer to verify and satisfy themselves to all aspects and information on property and or inspections sold as is. Buyer to verify water, gas, and electric locations and availability.

800 Interstate Dr, Winchester
$500,000
20111871 MLS
Visibility, Access, Utilities on site per seller/per plat-buyer to verify, zoned B-3. 1.52 acres located at I-64 exit 96, Right in front of the Hampton Inn, buyer to verify and satisfy themselves to all aspects and information on property. and inspections sold as is. Buyer to Check with all utilities companies to very water electric and gas availability and locations on all utilities.

1005 Early Dr, Winchester
$665,000
3 Beds ⋅ 3 Baths ⋅ 24025581 MLS
Introducing the Alexis, a stunning all-brick ranch home with incredible curb appeal and a charming front porch. This thoughtfully designed 3-bedroom, 2.5-bath home features a desirable split-bedroom layout, offering privacy and comfort. The spacious primary suite includes a luxurious ensuite with double vanities, a walk-in closet with direct access to the separate utility room for added convenience. The open-concept kitchen flows seamlessly into the great room, which is highlighted by a gas log fireplace and built-in cabinetry. The kitchen is a chef's dream, featuring a large island, a cozy breakfast area, and a walk-in pantry for ample storage. The Alexis also includes a formal dining room, perfect for entertaining, along with a convenient drop zone with a bench for everyday use. With 9-foot ceilings and luxury vinyl plank flooring throughout, this home combines modern elegance with functionality. A 2-car attached garage completes this exquisite floor plan. Let'c customize your dream home in Mallard Cove with CP Builders!

414 Alexis Way, Winchester
$100,000
22024126 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.

165 Duclair Dr, Winchester
$29,000
24022901 MLS
This is a beautiful area to build your dream home. Backs up to a golf course for a magnificent view. Just minutes from Fort Boonesborough National Park.

102 Augusta Dr, Winchester
$825,000
26015570 MLS
308 West Lexington has been renovated recently as an office space for a medical practice. The main space consists of a bright reception area, large office, file room, 5 exam rooms and kitchen area. The back of the building has two suites that could be leased out separately or incorporated into the main space. The basement area is unfinished but could be up-fitted for additional office space. The parking lot is generous in size and has access to a back alley way. This property could also be leased. Gateway to the downtown district, close to the Bypass and I-64. Very accessible area. Property Highlights: -Recently renovated -Great location -Multiple Opportunities

308 W Lexington Ave, Winchester
$1,500,000
25502084 MLS
Right off of Boonesboro Road lies 60.65± acres of Kentucky history waiting for its next chapter! This remarkable property sits along historic Howard's Creek and is located on the site of the original Bush Settlement—one of the earliest settlements in Kentucky. Formerly a working tobacco farm, this versatile acreage offers opportunities for cattle, hay, or crops, with timber and mineral rights conveying. Wildlife is abundant, with wild turkey and deer frequently spotted across the land. A rare stone fence surrounds the property, adding to its timeless character. The land neighbors Old Providence Church—now known as Old Stone Church—Kentucky's 11th oldest standing building, dating back to 1793, where legendary frontiersman Daniel Boone was once a member. Whether you're seeking farmland, recreation, or an investment in Kentucky's past, this property offers a chance to own a genuine piece of Bluegrass history. Schedule a showing today and experience it for yourself! Buyer to satisfy themselves with survey and all property information. More Photos Coming Soon!

1015 Old Stone Church Rd, Winchester
$99,500
2 Beds ⋅ 2 Baths ⋅ 26012893 MLS
Affordable housing! Check out this newly remodeled and updated home! 2 bedroom, 2 full bath! All new flooring, cabinets, vanities, and so much more! No lot rent here! You will own the lot as well, making this a great option for starter, downsizing, investment property (previously rented for $925), or just an affordable home. Nice covered porch, 2 storage sheds, brand new metal roof! $150 per month HOA fee covers your water, sewer, trash, and common area maintenance.

563 Constitution Dr, Winchester
$1,800,000
26008233 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 #1, Winchester
$299,999
25001584 MLS
An excellent opportunity to own a fully leased, income-producing property in the heart of Downtown Winchester, Kentucky. This beautifully renovated 2,310 SF retail storefront is being offered at a 10% cap rate, making it an attractive turnkey investment from day one. The building may be old, but nearly everything inside is new! Recent improvements include a new roof, four new skylights, exposed beams, new hardwood flooring throughout, updated electrical and plumbing, and HVAC. The space is plumbed for four bathrooms and also includes a laundry room and private back office with a window overlooking the main retail area. This property boasts a large rear parking lot—one of the largest in Downtown Winchester—providing convenient parking for tenants, customers, and employees. The location is surrounded by continued downtown growth. Seven new high-end apartments across the street, while the same block is already home to five restaurants, numerous shops, and the Leeds Center for the Arts. Property Highlights: -Recently renovated with a new roof, 4 new skylights, exposed beams, new hardwood floors, new plumbing and new electrical. -The property is located directly across from a brand-new apartment building and is surrounded by retail and restaurants. -The property boasts the largest back parking lot in the downtown area, a bonus for staff and customer accessibility. -Downtown Winchester, KY is booming - everyone wants to be Downtown, introducing shops, restaurants, and new apartment living options. Winchester, KY is conveniently situated just 18 miles east of Lexington and, with proximity to I-64, provides quick access to the larger city's amenities. Downtown Winchester is home to a variety of beloved local establishments, including the historic Leeds Center for the Arts, La Trattoria, The Hall Coffee & Social Club, and several small shops. Over 30 new, high-end apartments are coming to Downtown Winchester - residents and tourists want to be Downtown!

16 N Main St, Winchester
$575,000
26005455 MLS
This 1.7+/- acre parcel represents an excellent opportunity for almost any commercial application. The property has 397 feet of frontage along busy Colby Road (9,170 AADT, 2015) near its intersection with the Winchester Bypass (23,200 AADT, 2011). Located in the main shopping corridor of Clark County, this property receives tons of exposure and traffic from the adjacent Walmart Super-center, various banks, restaurants, gyms and other successful businesses, along with several heavily-populated residential developments which surround it. This is an absolutely great opportunity for almost any business or developer. Seller has included preliminary development plan for self storage units approved in 2022.

1025 Colby Rd, Winchester
$189,900
3 Beds ⋅ 2 Baths ⋅ 26011564 MLS
This move in ready ranch home offering 3 bedrooms and 2 full bathrooms is ready for a new owner. This home is in an income restricted community, 80% of LIHTC for Clark County. Property offers brand new cabinets, countertops, appliances, flooring, fresh painting and more. Contact listing agent to receive the income limits for buyers to qualify to purchase property. Set up your showing today!

225 Buffalo Trce, Winchester
$204,900
3 Beds ⋅ 2 Baths ⋅ 26004000 MLS
Ranch with covered porch, new roof, new appliances and countertops, new bath vanity, new professional paint job. Vaulted ceiling in the living room. Clean and ready for occupancy.

500 Hidden Hills Way, Winchester
$52,000
25501428 MLS
Property Has been REDUCED!!! Nature lovers property. Four Mile Creek which runs into the Kentucky River is across the road. Nearby are restaurants, boat landings, kayak rentals, and historical sights. Don't miss your chance to have a chance to be "on the river"!!!

4700 Four Mile Rd, Winchester
$300,000
20111875 MLS
Easy Location, Metal/Pole Barn approx 1675sqft, type garage on site with three 10x10 garage doors, two 8ft doors and 2 entrances, currently split access to each side, Utilities on site per seller/per plat, water and gas is not hooked up to building, zoned B-3. .58 acres located at I-64 exit 96, buyer to verify and satisfy themselves to all aspects and information on property sold As Is buyer to verify all information and access to water, gas, electric and locations. Per seller egress and ingress rights down Holiday Drive to building.

1045 Early Dr, Winchester
$100,000
22024124 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.

169 Duclair Dr, Winchester
$379,000
4 Beds ⋅ 3 Baths ⋅ 26015608 MLS
Welcome to 107 Hibiscus, where thoughtful updates, quality craftsmanship, and exceptional maintenance come together in this spacious 4-bedroom, 2.5-bath home. Offering a versatile floor plan with generous living spaces, this move-in-ready property has benefited from approximately nearly $70,000 in improvements over the past several years, providing peace of mind and modern finishes throughout. Major mechanical updates include replacement heat pumps (downstairs in 2020 and upstairs in August 2024), all new energy-efficient windows installed in 2025 with a transferable 10-year warranty, a new three-panel sliding back door, recently cleaned ductwork, spray-foam insulated crawl space, additional attic insulation, a roof replaced approximately 8-10 years ago, and garage doors replaced approximately two years ago. Inside, you'll appreciate the beautiful ¾-inch solid oak hardwood flooring throughout the main level, fresh interior paint, updated light fixtures, ceiling fans, new door hardware, elegant crown molding, a cozy gas log fireplace, and renovated bathrooms featuring updated tile, mirrors, lighting, faucets, and refreshed cabinetry. The beautifully updated kitchen is designed for both everyday living and entertaining, offering new granite countertops, freshly painted cabinetry, all-new stainless steel appliances including a gas range, dishwasher, microwave, and refrigerator, plus a convenient coffee bar that adds both style and functionality. Outdoor living is just as impressive with a large deck, a freshly painted front porch, and a high-quality custom-built storage shed constructed with 12-inch studs for exceptional durability. If you're searching for a meticulously maintained home where many of the major updates have already been completed, 107 Hibiscus deserves a place at the top of your list. Buyer to verify all aspects of the property, including but not limited to square footage, schools, boundaries, and any information deemed important to the purchase. Schedule your showing today!

107 Hibiscus Ln, Winchester