Winchester Real Estate

Winchester Real Estate

Welcome to Winchester, a charming city nestled in the heart of Clark County, Kentucky. Known for its rich history and small-town charm, Winchester offers a perfect blend of modern amenities and a strong sense of community.

Winchester boasts a vibrant downtown area with a variety of local shops, restaurants, and cultural attractions. Residents can enjoy leisurely strolls down Main Street, exploring unique boutiques and cozy cafes. The city also hosts regular events and festivals that bring the community together in celebration.

Nature enthusiasts will appreciate Winchester's proximity to outdoor recreation opportunities. With easy access to parks, hiking trails, and scenic countryside, residents can enjoy a range of activities in the great outdoors.

Families are drawn to Winchester for its excellent schools and safe, family-friendly neighborhoods. The city has a strong sense of community pride, with residents actively participating in local events and initiatives.

Whether you're looking to settle down in a peaceful, historic town or seeking a close-knit community to raise a family, Winchester has something to offer everyone. Come discover the beauty and warmth of Winchester, where small-town charm meets modern convenience.

Newest Listings in Winchester

$369,900
3 Beds ⋅ 2 Baths ⋅ 26024780 MLS
If you've been searching for an immaculate ranch home in a great location, this is one you won't want to miss! Let's start with the updates. This beautifully maintained home features newer heating and cooling, a newer water heater, granite countertops, updated kitchen and appliances, a privacy fence, professional landscaping, exterior lighting, and so much more. Now that I have your attention, let's talk about the home itself. Offering three bedrooms, two full bathrooms, and a spacious bonus room that could easily serve as a fourth bedroom, this home has an incredible layout with plenty of flexibility for your lifestyle. Then there's the outdoor living space! You'll find yourself spending countless mornings and evenings relaxing on the large, covered, screened-in back patio, overlooking your private backyard. It's the perfect spot to enjoy your morning coffee, entertain guests, or simply unwind at the end of the day. With its thoughtful updates, fantastic layout, beautiful outdoor space, and move-in-ready condition, this ranch is truly a home you'll want to see for yourself!

327 Primrose Ln, Winchester
$45,000
26024771 MLS
Introducing this 5.59 acre property in Central Kentucky! With city water and electric available at the road, this land offers a seamless transition for your dream home or investment project. Located just 15 minutes from Winchester, 30 minutes from Hamburg, and 30 minutes from Mt. Sterling. You will enjoy easy access to city amenities while relishing the peace of rural living. Don't miss the opportunity to own a piece of prime Kentucky real estate!

199 Midway Rd, Winchester
$855,000
3 Beds ⋅ 3 Baths ⋅ 26024725 MLS
Discover the charm of country living on nearly 15 acres of beautiful, mostly flat to gently rolling farmland, offering picturesque views and plenty of space to enjoy the outdoors. This well-maintained property features a barn, equipment shed, workshop, and an attached three-bay garage, providing exceptional storage and workspace for equipment, hobbies, or farm use. Inside the home, you'll find warm hardwood flooring, modern appliances, and inviting living spaces filled with natural light. Flexible use areas are available inside the house as well as in the out buildings. A sunroom provides the perfect spot to relax and take in the beautiful surroundings, while the porches offer wonderful spaces for enjoying peaceful mornings or evening sunsets. The back porch features durable composite decking for easy outdoor living and entertaining. The basement includes a practical area ideal for canning, food preparation, projects, or additional workspace. With its combination of usable acreage, multiple outbuildings, comfortable living spaces, and beautiful rural views, this property offers a wonderful opportunity to enjoy the best of country living while still having the conveniences of a thoughtfully maintained home.

5960 Van Meter Rd, Winchester
$329,000
3 Beds ⋅ 2 Baths ⋅ 26024503 MLS
This beautiful 3 bedroom 2 bath home has so much to offer. The HVAC is only 1 year old and is still under warranty. Appliances are just 3 years old. The backyard has privacy fence all around that was built last year. The home has an above ground pool with a deck built around it. The pool liner and pump was replaced last year. This home is in an excellent location. Just minutes from retail shops, restaurants, golf courses, and several amenities. It is a short drive to Hamburg and Lexington. The interior is in pristine condition. Schedule a private tour before this one is gone.

358 Hanover Dr, Winchester
$259,900
3 Beds ⋅ 1 Baths ⋅ 26024178 MLS
Welcome to this freshly renovated farmhouse in the heart of Trapp, Kentucky! Blending timeless farmhouse charm with fresh updates, this property is ready for its next chapter. The possibilities are endless—come see all this special home has to offer. An absolute must-see!

11304 Irvine Rd, Winchester
$110,000
26024261 MLS
Discover the perfect setting for your dream home on this beautiful 4.14-acre tract at 3999 Bybee Road, Winchester, KY 40391. Nestled among the rolling hills of Kentucky's Bluegrass region, this picturesque property offers stunning panoramic countryside views and the peace and privacy you've been searching for. The gently rolling terrain provides multiple potential building sites, giving you the flexibility to design the home you've always envisioned while enjoying breathtaking views in every direction. With approximately 4.14 acres of open land, there's plenty of room for a custom home, detached garage, workshop, barn, or hobby farm. Existing fencing is located along portions of the property, and the surrounding landscape creates a quiet, scenic setting that's perfect for enjoying nature, watching wildlife, or simply relaxing after a long day. Located just minutes from downtown Winchester, you'll enjoy the best of both worlds: peaceful country living with convenient access to shopping, dining, schools, and I-64 for an easy commute to Lexington. Whether you're ready to build now or invest in a beautiful piece of Kentucky countryside for the future, this exceptional property offers endless possibilities. Don't miss this rare opportunity to own 4.14 acres in one of Clark County's most desirable rural settings.

3999 Bybee Rd, Winchester
$359,900
3 Beds ⋅ 3 Baths ⋅ 26024212 MLS
Location is prime on the west side of Clark county, close to Lexington, schools, shopping and in a well established neighborhood. Pride shows in the care of this 1-1/2 story brick home. Everything you need can be found on the 1st level - master bedroom with a door leading to a hot tub on the back patio. This home has a large living room, with wood floors and fireplace, kitchen with new major appliances that are all staying with home and granite counter tops, and a dining area with door leading to a covered porch. There are 2 more bedrooms and a full bath upstairs. Lots of hardwood and new carpet. Great closet space offering lots of storage!

420 Calmes Blvd, Winchester
$350,000
3 Beds ⋅ 3 Baths ⋅ 26024167 MLS
Attention Investors! This 3 plex in the heart of Winchester is a great investment. There are 3 apartments that are all currently rented out. The bottom floor has a huge living room, bathroom, and kitchen. The other two upstairs also have a living room, kitchen, bathroom, and bedroom. There is also a huge deck on the back for entertaining. Schedule an appointment to take a look before this one is gone.

135 E Broadway St, Winchester
$150,000
3 Beds ⋅ 1 Baths ⋅ 26024165 MLS
Welcome home to this charming 3-bedroom, 1-bathroom property featuring a comfortable living room, dedicated dining room, and a functional layout with plenty of potential. Outside, you'll find a detached 1-car garage and a long driveway. Whether you're looking for your first home or your next investment opportunity, this property offers a great combination of space, functionality, and potential. Property is being sold AS-IS

5 S Burns Ave, Winchester
$165,000
3 Beds ⋅ 1 Baths ⋅ 26024016 MLS
Conveniently located in Winchester, this one-story home offers three bedrooms, one bath, and plenty of potential for a first-time buyer or investment property. Inside, you'll find laminate and vinyl flooring throughout, a spacious kitchen, and a separate laundry room. The bathroom received new fixtures in 2025, while the roof is approximately 1.5 years old, taking care of two worthwhile updates for the next owner. Gas freestanding heaters provide heat, and the home does not currently have central air. Outside, there's a covered front porch and a nice-sized backyard with an alley running behind the property. Whether you're looking for an affordable place to call your own or an addition to your rental portfolio, this home is ready for its next chapter.

209 E Washington St, Winchester
$235,000
3 Beds ⋅ 1 Baths ⋅ 26023896 MLS
Welcome to 119 Tower Lane! This beautifully remodeled 3-bedroom, 1-bath home offers the perfect combination of modern updates and peaceful country living. Situated on 5 acres, there's plenty of room to enjoy the outdoors, spread out, and make the property your own. Whether you're looking for a move-in-ready home with acreage or a peaceful place to call home, this property is one you won't want to miss! Privately positioned and surrounded by natural beauty, this renovated berm-style residence offers the perfect balance of seclusion and sophistication. Inside, you'll find thoughtfully curated updates including fresh paint, updated flooring, and a bright, inviting interior that feels both modern and timeless. The kitchen has been refreshed with contemporary appliances and stylish finishes, offering a functional and comfortable space for everyday living. Featuring three bedrooms and an updated bath, the home delivers comfort with understated elegance. Energy-efficient berm construction enhances year-round efficiency and quiet living. Outdoors is where this property truly shines. Five unrestricted acres create endless potential for recreation, gardening, animals, or simply enjoying unmatched privacy and open space. A covered carport adds convenience. A distinctive property that combines modern updates, privacy, and opportunity all just minutes from town!

119 Tower Ln, Winchester
$225,000
4 Beds ⋅ 2 Baths ⋅ 26023784 MLS
This move in ready ranch home offering 4 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. The 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!

522 Acadia Way, Winchester
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