Winchester Real Estate Search

Winchester Properties for Sale

With an incredible location and the distinction of being known as the Horse Capital of the World, Winchester, Kentucky, is a great place to live just minutes from Lexington. Winchester offers unique experiences, many that originated in the city. For example, “Kentucky’s Official Soft Drink,” Ale-8-One was founded in Winchester, and the city hosts the country’s only annual Beer Cheese Festival and only Beer Cheese Trail to celebrate the creamy concoction that was created in Winchester.

Similarly, Winchester was a commercial hemp leader hundreds of years ago, and has been leading the re-emergence, too. Beyond these fun facts, Winchester has many other advantageous features, including an incredible location just fifteen miles west of Mt. Sterling and eighteen miles east of Lexington. The community is also only thirty-six minutes from rappelling, rock climbing, camping, hiking, and other opportunities for outdoor adventures at Red River Gorge. Additionally, the city boasts a long list of exciting entertainment options, cultural and historical points of interest, and fabulous restaurants. A few examples include, Harkness Edwards Vineyards, Fort Boonesborough State Park, Mt. Folly Farm, Bluegrass Heritage Museum, Leeds Center for the Arts, Wildcat Willy’s Distillery, Red Fern Coffee Company, Gaune’s Deli and Cafe, Frank’s Donuts, and Abettor Brewing Company, to name a few.

In a city with so much to offer, the variety also includes its housing options. Winchester real estate is extraordinarily diverse and includes a vast array of detached single-family homes, semi-detached townhomes, and lower-maintenance attached apartments and condos. Likewise, real estate in Winchester consists of properties of many different floor plans, architectural designs, ages, and square footage. The diversity of Winchester properties is evident in the broad range of listing prices for Winchester homes. We look forward to sharing specific details about the homes for sale in Winchester, Kentucky, so please contact us today so we can help you with your home search.

Our website features the best Winchester real estate search for homes, condos, land and foreclosure properties available. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes. 

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Newest Winchester Properties for Sale

$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
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