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$320,000
4 Beds ⋅ 3 Baths ⋅ 26009835 MLS
Welcome to this beautiful BRAND NEW HOME in downtown Winchester! The open-concept design flows into a gorgeous kitchen w/granite countertops, gas stove, stainless appliances, and lots of cabinets. A first-floor bedroom w/private bath offers convenience flexibility. Upstairs, you'll find three generously sized bedrooms, each w/large closets, plus motion-activated hallway lighting. A covered back porch is the perfect spot to relax or entertain.

38 N Burns Ave, Winchester
$275,000
3 Beds ⋅ 2 Baths ⋅ 26007260 MLS
Simply the Best! 3 Bedroom, 1 1/2 bath All Brick ranch home located within walking distance to historic downtown Winchester, Country Club, Middle School, great place to live, you will spend most of your time on the Sunporch off the Kitchen, large lot, many updates, floor, bathrooms, new furnace, fresh paint, don't miss looking at this jewel, call today

103 Southern Ct, Winchester
$123,000
25503896 MLS
Discover the perfect blend of privacy, nature, and convenience on this beautiful 11.47-acre tract located along Four Mile Road in Clark County. This unique property adjoins the scenic Four Mile Creek, offering a peaceful, picturesque setting ideal for those seeking a quiet country retreat or a place to build their dream home. The land features a mix of open and wooded areas, providing excellent potential for a permanent homesite, recreational getaway, or hunting retreat. Whether you envision mornings spent listening to the creek or evenings around a campfire surrounded by nature, this property delivers the ideal backdrop. On-site utilities remain from a former residence, making it even easier to bring your vision to life. Enjoy the tranquility of rural Kentucky living while still being within easy reach of Winchester, Lexington, and major highways. Don't miss this opportunity to own a versatile and scenic piece of land with endless possibilities along Four Mile Creek.

7950 Four Mile Rd, Winchester
$175,000
22004991 MLS
Lot # 13 contains 6.588 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.

990 Craig Crossing Rd, Winchester
$400,000
22007107 MLS
Great opportunity to buy and build just off the Winchester Bypass. This property is nicely located in the midst of a great deal of new development including a brand new, state-of-the-art CHI Saint Joseph Health Center. Other new development in the immediate area includes Clean Sweeps and Domino's Pizza. Additionally, Walmart and Kroger are located directly across the Bypass from this site. See enclosed Conceptual Development Plan that shows how a standard-sized fast food restaurant with drive thru would fit on this lot. Property Highlights: - Surrounded by area retail - Could be paired with offering at 205 Codella Dr. - Conceptual development plans illustrate QSR with drive-thru

145 Codella Dr, Winchester
$309,900
3 Beds ⋅ 3 Baths ⋅ 26014026 MLS
Welcome to this well-maintained home located in a quiet, established neighborhood with convenient access to everything Winchester has to offer. The first floor features an open and inviting layout, creating a comfortable space for everyday living and entertaining alike. Upstairs, you'll find a traditional three-bedroom floor plan with generously sized bedrooms, including a spacious primary suite. Recent updates include a brand-new roof, along with manufactured hardwood flooring installed in the living area, foyer, and primary bedroom. Conveniently located near the Winchester Bypass, this home offers quick access to shopping, dining, and everyday amenities, while also providing easy access to I-64, I-75, Lexington, and the Mountain Parkway for commuters and travelers. Offering a desirable combination of space, updates, and location, this home is ready for its next owner to enjoy. Schedule your private showing today!

335 Newcastle Ln, Winchester
$100,000
22024123 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.

215 Duclair Dr, Winchester
$100,000
22024128 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.

155 Duclair Dr, Winchester
$146,900
3 Beds ⋅ 2 Baths ⋅ 26013935 MLS
Lovely older home, located witin waking distance to collage park whice offers Pickle Ball, Pool, Tennis, play gound and Walking Trail, also walking distance to Historic Downtown Winchester, with a little love house brings large rooms and a nostlogic atmosphire, take a look, view today, this a a great price for 3 bedrooms, 1 1/2 baths, nice back yard, with parking, call today! Selling "AS IS", inspections welcome, the are no utilties on at the present, Estate Please make sure all doors are locked when you leave, buyer to verifye size of home & Lot

65 Fitch Ave, Winchester
$700,000
25505199 MLS
Commercial lot with proximity to the Bypass, multiple area schools, hospital, Interstate 64, and the Bert T. Combs Mountain Parkway. Zoned PD, planned development.

1496 Martin Luther King Jr Dr, Winchester
$100,000
22024134 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.

115 Duclair Dr, Winchester
$155,000
2 Beds ⋅ 1 Baths ⋅ 26008307 MLS
Welcome Home! Located across the street from a park with walking trails and 2 dog runs, this home is ready for a new owner. Featuring 2 bedrooms on the first floor and an optional 3rd bedroom or bonus room in the partially finished attic space. The original hardwood floors are located throughout the home. Home features a newer roof and gutters as well as a large fenced backyard. Schedule your private tour today!

13 Maryland Ave, Winchester
$110,000
22024092 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.

200 Duclair Dr, Winchester
$220,000
4 Beds ⋅ 3 Baths ⋅ 26004331 MLS
Turnkey downtown triplex with tenants already in place. An excellent addition to any investor's portfolio. Two units have been recently updated, while the third features a long-term tenant with future value-add potential. Property includes two 1BD/1BA units and one 2BD/1BA unit. Tenants pay all utilities directly except water, which is on a RUB system, keeping operating costs low. Strong income potential in a prime downtown location with continued upside. Selling as-is.

130 E Broadway St, Winchester
$274,500
3 Beds ⋅ 2 Baths ⋅ 26011465 MLS
Welcome to this delightful 1.5-story home perfectly situated on a spacious corner lot just off the Eastern Bypass and only minutes from I-64. Convenience meets comfort in this beautifully maintained property offering 3 bedrooms, 2 full baths, and an inviting layout designed for everyday living. Step inside to an open living area ideal for entertaining, a spacious kitchen and dining space, and plenty of room for family and friends to gather. Natural light fills the home, creating a warm and welcoming atmosphere throughout. Outside, enjoy an oversized backyard complete with a charming white picket fence — perfect for children, pets, gardening, or hosting outdoor entertaining. Whether you're a first time buyer or searching for your forever home, this property offers comfort, convenience, and character all in one. Call today for more information or to schedule your private showing. Note: Offer to Purchase with Contingency and Kick-out Clause. Buyer cannot perform without the sale of current property.

137 Eastridge Dr, Winchester
$399,000
26011689 MLS
11 acres of golf course adjacent land with development plan. Owner/Broker. Road and utility estimates available upon request. A list of individuals interested in lots available upon contract.

Fairholme Way, Winchester
$100,000
22024120 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.

111 Jacob Ct, Winchester
$350,000
26014375 MLS
Looking for land to build your dream home that is private, but convenient? This 7+ acre beautiful lot is located in Clark County, just 15 minutes from Costco, Hamburg and I-75. No HOA or deed restrictions. The perfect place to build or have a small farm. City water and electricity available at the street. No city sewer.

4095 Basin Springs Rd, Winchester
$490,000
25508043 MLS
Discover a rare opportunity in downtown Winchester with this assemblage of four vacant lots being sold together as a single offering. Zoned L1 and totaling approximately 1.53 acres, this property presents exceptional potential for redevelopment, infill housing, multiunit residential, mixeduse, or commercial concepts in a central location. Situated just steps from local shops, restaurants, services, and community amenities, these lots deliver true walkable convenience while providing a sizable footprint rarely available in the heart of Winchester. The level terrain and cleared condition simplify planning and construction, giving developers, builders, and investors flexibility to pursue a range of uses aligned with L1 zoning allowances. Whether you're looking to create new housing opportunities, a boutique retail destination, or a thoughtful mixeduse project that contributes to downtown vitality, this assemblage invites strategic vision and development. With accessible infrastructure and a strong community backdrop, 33-41 Winn Avenue is a compelling site for those ready to build in one of Kentucky's vibrant small towns.

33-41 Winn Ave, Winchester
$50,000
25018185 MLS
Tucked away on a quiet cul-de-sac in Mallard Place, this .41-acre lot is ready for your vision. Imagine your dream home in a neighborhood known for its charm and convenience. Bring your house plans—your future starts here!

308 Duclair Dr, Winchester
$420,000
3 Beds ⋅ 2 Baths ⋅ 26015824 MLS
Welcome to 187 Hawthorne Drive, a beautifully maintained brick home in one of Winchester's most sought-after neighborhoods. Offering convenient one-level living, this 3-bedroom, 2-bath home features an inviting open floor plan that's perfect for everyday living and entertaining. The spacious living room is anchored by a cozy natural gas fireplace with gas logs, creating a warm and welcoming gathering space. The eat-in kitchen features a breakfast bar and includes a brand-new refrigerator and a quiet new garbage disposal. Recent updates throughout the home provide both style and peace of mind. Gorgeous hardwood flooring has been added to all three bedrooms, and tile flooring has been installed to replace the previous vinyl in the laundry room, pantry, and hallway. The private primary suite is thoughtfully situated on its own side of the home and features an updated shower insert. Enjoy relaxing mornings with coffee or peaceful summer evenings on the screened-in back porch, where you can take advantage of the outdoors without the bugs. Plenty of storage is available with an extra garage closet, pull-down attic storage, and an extra-high crawl space that's ideal for storing lawn equipment, seasonal items, or outdoor tools. The sellers have also invested in ensuring the crawl space remains dry and well protected. Additional upgrades include an HVAC system, updated closet shelving throughout the home, and natural gas service installation. If you're searching for a move-in ready home in Winchester, KY with one-level living, modern updates, excellent storage, and a desirable location close to shopping, dining, schools, and everyday conveniences, 187 Hawthorne Drive is one you won't want to miss.

187 Hawthorne Dr, Winchester
$649,000
4 Beds ⋅ 3 Baths ⋅ 26006869 MLS
Fontaine Estates, a great place to call home. This spacious 4 bedroom 3 bath property offers an abundance of storage,, including charming window seats. Enjoy the convenience of an oversized driveway and garage, along with a beautifully designed outdoor setting, feauring a fire pit and a dedicated entertainment space. The thoughtfully planned, custom designed landscaping enhances the home's curb appeal while the finished basement provides the perfect area for both fun and relaxation. Custom built csbinets add charm and functionality throughout the home, complemented by two generous lots offering plenty of space to spread out. The expansive yard features mature, shade giving trees and a unique historical cemetary bordered by distinctive rock fencing creating a property rich in character, privacy and natural beauty.

186 Chardonnay Ct, Winchester
$635,000
4 Beds ⋅ 3 Baths ⋅ 24025583 MLS
Introducing the Denver, a gorgeous all-brick ranch home offering 4 bedrooms and 2.5 baths, designed for both luxury and practicality. With its stunning curb appeal, front porch, and beam accents, this home makes a lasting first impression. Inside, the split-bedroom layout offers privacy and space for everyone, with a large primary suite featuring a walk-in closet, soaking tub, separate shower, and double vanities. The open-concept kitchen and great room are perfect for entertaining, complete with a gas log fireplace, large kitchen island, and walk-in pantry. The home also includes a formal dining room, half bath, and a separate utility room for added convenience. Nine-foot ceilings and luxury vinyl plank flooring throughout create a seamless, modern feel. With ample space, thoughtful design, and beautiful finishes, the Denver is the perfect place to call home. Come custom build the Denver plan with CP Builders in Mallard Cove!

422 Alexis Way, Winchester
$100,000
22024100 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.

270 Duclair Dr, Winchester
$110,000
22024112 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.

135 Jacob Ct, Winchester
$264,900
5 Beds ⋅ 2 Baths ⋅ 26004166 MLS
**Don't miss this exciting opportunity to pick out the new flooring for the basement and kitchen with a full price offer.****New roof (8 months old), one year old AC and heating unit, new large storage shed, and one year old wooden fence All of the expensive upgrades have been done. Come make this home your own. All-brick ranch with a full walk-out basement! This charming home offers excellent potential for the right buyer. The main level features three bedrooms, a full bath, a comfortable living room, and an eat-in kitchen. The walk-out basement expands the living space with two additional bedrooms, full bath, family room with a kitchenette area, utility room, and ample storage with built-in shelving. Step outside to a spacious backyard, fully enclosed with a wooden fence, perfect for pets, play, or outdoor enjoyment.

55 Hillcrest Dr, Winchester
$108,500
25501424 MLS
!!!MAJOR REDUCTION!!! Check It Out! Nature lovers property. There is a rock wall at the top with the Four Mile Creek which runs into the Kentucky River across the road. Nearby are restaurants, boat landings, kayaks and historical sights. The trees will keep it private. Take advantage of this PRICE CHANGE to have a property close to the river!!!

4590 Four Mile Rd, Winchester
$134,900
2 Beds ⋅ 1 Baths ⋅ 26006389 MLS
Charming Fixer-Upper with Endless Potential - Priced to Sell!! This older gem is full of character and opportunity! Featuring solid bones and classic charm, this property is perfect for buyers with a vision who are not afraid to add a little TLC! Whether you're an investor, DIY enthusiast, or someone dreaming of restoring a home to its former glory, this is your chance to build equity and create something special at a price that is hard to beat. Call today to schedule you private showing.

174 Cook Ave, Winchester
$455,000
8 Beds ⋅ 4 Baths ⋅ 26004961 MLS
Great investment opportunity in downtown Winchester! This spacious quadplex has been updated throughout and offers a true turn-key multi-family property. Each unit features two bedrooms, one bathroom, a full kitchen, and its own private laundry area. Utilities are separately metered, allowing tenants to handle their own services and helping keep operating costs manageable. With a total of 8 bedrooms, 4 bathrooms, and approximately 5058 square feet, this property provides strong rental potential in a convenient location close to downtown shopping, dining, and local amenities. The units are clean, well-maintained, and ready for new tenants, making this an excellent option for investors seeking a solid income-producing property. Schedule your showing today before this opportunity is gone!

265 S Highland St, Winchester