Winchester Real Estate

Winchester Real Estate

Welcome to Winchester, Kentucky, a charming city nestled in the heart of Clark County! Known for its rich history and vibrant community, Winchester is a place where small-town charm meets modern convenience. With a population of just over 18,000 residents, this picturesque city offers a warm, welcoming atmosphere that makes it an ideal place to call home.

Winchester boasts a variety of historical landmarks and attractions that reflect its storied past. One of the most notable is the Clark County Courthouse, a stunning example of 19th-century architecture that stands proudly in the town square. The city's commitment to preserving its heritage is evident in the many well-maintained buildings and sites that dot the landscape, inviting residents and visitors alike to explore its history.

Nature lovers will appreciate the abundance of outdoor activities available in and around Winchester. The nearby Red River Gorge and Daniel Boone National Forest offer breathtaking scenery and numerous hiking trails, perfect for a weekend adventure. Additionally, the city's parks provide ample opportunities for family picnics, sports, and leisurely walks.

Winchester is also home to a thriving local economy, with a diverse range of businesses that cater to residents' needs. From quaint boutiques to delicious dining options, there’s something for everyone. The community is known for its friendly atmosphere and strong sense of belonging, making it easy to meet new friends and build lasting connections.

Whether you’re seeking a peaceful retreat or a place to grow your family, Winchester, KY, is a hidden gem waiting to be discovered. Come and experience the charm and warmth of this delightful city!

Newest Listings in Winchester

843 Ford Hampton Rd, Winchester
$540,000
5 Beds ⋅ 3 Baths ⋅ 26030232 MLS
Enjoy peaceful country living on 9.09 acres, just off Boonesboro Road with convenient access to both Winchester and Richmond! Surrounded by beautiful wooded scenery, this spacious 5-bedroom, 2.5-bath home offers plenty of privacy and room to spread out. The main level features hardwood flooring, a welcoming living room, a kitchen with granite countertops and stainless steel appliances, a dining area, and screened in backporch. You'll also find three bedrooms on the main level, including the primary suite, while upstairs offers two generously sized additional bedrooms and a half bath. Step outside to the covered, screened-in back porch, updated in 2025, where you can relax and enjoy the peaceful wooded surroundings. The finished walkout basement provides even more flexible living space, perfect for a second living area, recreation room, or entertaining. The property also features a detached garage, carport, and a mix of cleared and wooded acreage. Major improvements include a new roof in 2021, HVAC units in 2022, remodeled bathrooms, added insulation, and new carpet in the primary suite and on steps. With its easy access to town, this property offers the space and privacy of rural living without sacrificing convenience!

843 Ford Hampton Rd, Winchester
203 Steve Cir, Winchester
$384,900
3 Beds ⋅ 3 Baths ⋅ 26030140 MLS
Conveniently located in a quiet cul-de-sac in one of Winchester's most desirable, established neighborhoods, this well-maintained 2,000+ sq. ft. home offers a spacious and functional layout. Cozy up by the wood-burning fireplace in the inviting living area, or step outside to enjoy the fully fenced, expansive backyard—perfect for pets, play, or outdoor entertaining. What truly sets this property apart is the ultimate peace of mind provided by a whole-home gas generator, offering seamless protection year-round. Packed with updates including a brand-new water heater, updated pool pump, replaced HVAC system, and an upgraded electrical panel, this turn-key residence is ready for its next chapter. The finished bonus room above the garage could be used as a 4th bedroom, office space, entertainment area—the options are endless! This home truly offers the perfect blend of comfort and functionality. Don't miss this fantastic opportunity—schedule your private tour today! (professional photos coming soon)

203 Steve Cir, Winchester
31 Casa Landa Way, Winchester
$380,000
3 Beds ⋅ 2 Baths ⋅ 26030008 MLS
This lovely white brick home w/black shutters is located in the prestigious Stoney Brook Subdivision. The large covered front porch welcomes you into a large foyer w/a great layout. Large living room opens into a formal Dining Room. Then step up into an efficient kitchen w/a breakfast bar as well as an eating area w/double windows. Family Room is open to the kitchen and features a fireplace and sliding glass doors to the back patio. Off the hallway are 3 bedrooms. The primary bedroom includes a full bath and a spacious walk-in closet. Two additional bedrooms w/nice sized closets and a 2nd full bath at the end of the wide hallway. Fenced backyard with patio across back of house. Large backyard.

31 Casa Landa Way, Winchester
1494 Amster Grove Rd, Winchester
$165,000
2 Beds ⋅ 2 Baths ⋅ 26029929 MLS
Morning coffee overlooking the Kentucky River, evenings around a fire pit, and a riverfront setting to enjoy every day—welcome to 1494 Amster Grove Road! This 2-bedroom, 1.5-bath home offers an open floor plan with a wood-burning fireplace and a first-floor bedroom spacious enough for a king-size bed. Upstairs, a second bedroom and half bath provide additional space. Outside, enjoy river views from the deck and covered patio, a generous yard for gathering, and a large carport with room for a truck and boat. Metal cabinetry and epoxy flooring add practical touches to the first level. Previously used as both a long-term rental and an Airbnb, this property offers options for a full-time home, weekend getaway, or potential rental, subject to applicable requirements. Property is located in a flood zone.

1494 Amster Grove Rd, Winchester
1515 Sewell Shop Rd, Winchester
$565,000
3 Beds ⋅ 2 Baths ⋅ 26029913 MLS
Modern Farmhouse Beauty on 2.83 acres with beautiful farm views! Enjoy the perfect blend of style and country living in this beautiful BRAND NEW CONSTRUCTION home with an amazing view of the peaceful countryside! Offering 3 bedrooms and 2 baths, this home combines stylish finishes, an open inviting great room, functional layout, and room to enjoy the outdoors. The exterior features crisp white board and batten siding, black windows, a dark architectural roof, classic brick skirt accent, creating timeless curb appeal. Inside you will find vaulted ceilings in the great room and primary bedroom, a spacious kitchen, a gas log fireplace, a warm inviting foyer, and massive windows for appreciating the view. The primary suite offers a relaxing retreat complete with a beautiful tile shower and a separate soaking tub with modern fixtures. Two additional bedrooms and a second full bath provide comfortable, versatile living space. Step out back onto the covered porch and check out the outdoor kitchen area! If you have been searching for a brand new home with modern finishes, a functional efficient layout, aesthetic upgrades, quality turn key ready construction, and beautiful country views, this property deserves a closer look!

1515 Sewell Shop Rd, Winchester
2323 Crowe Ridge Rd, Winchester
$120,000
1 Baths ⋅ 26029828 MLS
Opportunity to complete a custom residential build on 1.64 acres in Clark County. The property features a partially constructed home with electric, water, and septic infrastructure already installed on-site. House plans are available upon request; though the build has been modified to include additional square feet. Enjoy a rural setting located 18 minutes from downtown Winchester and 32 minutes from Hamburg. Offered via online auction running November 5 through November 19 OR Pre-Auction offers will be considered. PRE-AUCTION OFFERS: Seller reserves the right to accept a pre-auction offer prior to November 5, 2026, at 5:00 PM . All pre-auction offers must be submitted on a standard purchase agreement accompanied by proof of funds. Submit written offers to listing agent via dotloop.

2323 Crowe Ridge Rd, Winchester
208 Buffalo Trce, Winchester
$149,000
2 Beds ⋅ 3 Baths ⋅ 26029736 MLS
Multiple offers have been received on this property. Please submit your offer before the deadline shown below, or If your buyer would like to make any revisions to their submitted offer, follow the steps below: Navigate to VRM Properties (web address in private remarks) Sign In with Username & Password Click the Menu Icon (the 3 orange bars in the upper right side of the screen) Click "My Offers" and Submit your revisions by clicking on the Next Action: Submit Highest & Best link For detailed instructions, please see the attached Multiple Offers Job Aid attached to this listing. The Highest & Best deadline for revisions is 1:00PM Central Time on 10-30-2026. If no revisions are submitted by the deadline, the existing offer will be considered your final Highest & Best offer. Ranch style home on full, finished, walk out basement. Home features entry foyer, primary bedroom with adjoining bath, second full bath off the foyer, Great room style kitchen and living room area and a formal dining area/den. Lower level is finished with half bath, one bonus room with closet and second bedroom with windows but no closet. as well as a family room area. Additional bonus is the unfinished storage/storm shelter area. Home has off street parking, backyard deck and is ready for a new owner. This property has discoloration, Re-hab or construction loan or cash recommended.

208 Buffalo Trce, Winchester
705 W Lexington Ave, Winchester
$525,000
6 Beds ⋅ 5 Baths ⋅ 26029637 MLS
Welcome to 705 West Lexington Avenue, where historic charm, modern improvements, and exceptional investment potential come together in one remarkable property. Offering approximately 5,427 square feet on a generous approximate 0.61-acre lot, this distinctive Winchester property presents a rare opportunity to capitalize on substantial renovations already underway while bringing your own vision to life. Behind its timeless architectural character, you'll discover an impressive transformation in progress. Significant improvements have already been made, including updated kitchen and bathrooms, giving the next owner a valuable head start toward completing this extraordinary property. Generously proportioned rooms, distinctive architectural details, and an expansive floor plan create an exceptional canvas for a spectacular private residence or potential investment venture. While additional renovations and finishing touches remain, the groundwork has been laid for something truly special. An added bonus? An attached one-and-a-half-bedroom apartment offering exciting rental income potential! Whether you're seeking supplemental income, accommodations for extended family, or additional flexibility, this unique feature adds another dimension of value and opportunity. Previously identified as B-3 (Highway Business) zoned, the property may also present possibilities for commercial or mixed-use applications, subject to verification and applicable approvals. Its prominent location along West Lexington Avenue, convenient to downtown Winchester and Lexington, further enhances its appeal. Opportunities with this combination of size, character, improvements, income potential, and versatility are not easily found! For the visionary homeowner, savvy investor, or entrepreneur seeking their next project, 705 West Lexington Avenue offers the chance to finish an exciting transformation and unlock exceptional possibilities. The vision has begun. The opportunity is yours. Schedule your private showing and discover what this remarkable property could become!

705 W Lexington Ave, Winchester
103 Southern Ct, Winchester
$260,000
3 Beds ⋅ 2 Baths ⋅ 26029550 MLS
There's a lot to appreciate about this three-bedroom, one-and-a-half-bath brick ranch in Winchester! Inside, you'll find an eat-in kitchen, a comfortable living room, and a large sunroom with space to spread out, entertain, or enjoy a quiet afternoon. The owners have made plenty of updates over the past year, including a new furnace, laminate flooring, fresh interior paint, updated kitchen cabinets, and a new kitchen sink and faucet. Both bathrooms have been refreshed with new vanities, toilets, faucets, lighting, and exhaust fans. Other improvements include new interior doors and baseboards, outlets and switches, diffusers, lighting, and a new front door and storm door. Outside, there's landscaping, a patio, an attached carport, and a storage shed. If you're looking for one-level living with many of the updates already taken care of, come take a look!

103 Southern Ct, Winchester
117 Colonial Park Dr, Winchester
$209,000
3 Beds ⋅ 1 Baths ⋅ 26029492 MLS
Really Nice all Brick 3 bedroom, 1 Bath Ranch with large garage and a fully enclosed covered back patio in desireable Colonial Valley Neighborhood. Low Electric bills, HVAC 2 years old, Water Heater 3 years. Most comparable homes in this neighborhood don't have a garage or enclosed porch. Picture of Range and refrigerator are for illustration only. Seller will give a $1,000 allowance for appliances

117 Colonial Park Dr, Winchester
307 Mcdowell Dr, Winchester
$285,000
3 Beds ⋅ 2 Baths ⋅ 26029425 MLS
Enjoy Southern living in this charming Cape Cod-style home featuring three bedrooms, two full bathrooms, and a dedicated office. The main level includes the primary bedroom, office, full bathroom, laundry room, and a kitchen with a breakfast bar and dining area. Upstairs are two additional bedrooms and a second full bathroom. A spacious, level yard provides plenty of room for entertainment. Come enjoy today.

307 Mcdowell Dr, Winchester
48 Bon-Haven Ave, Winchester
$249,000
3 Beds ⋅ 2 Baths ⋅ 26029418 MLS
This charming Cape Cod home is tucked away in an established Winchester neighborhood only 14 miles to Hamburg and less than 5 minutes to I64. You will love the short walk to Legacy Park! Yes, it does have a 1st floor Primary bedroom. This cute home has lots of character throughout with a spacious living room and an inviting dining room. The roof is only 2 years old; the heating and cooling has been well maintained, and the exterior of the home has been recently painted. The upstairs area offers 2 additional bedrooms and a full bathroom. The basement has additional storage space and a laundry area. There is so much private outdoor space to enjoy! The huge backyard is fenced and backs up to greenspace. There is a large patio perfect for friends and family gatherings. If you need extra storage space, you will enjoy the detached 2 car garage for all your outdoor toys. For convenience the property also has two separate driveways. Don't wait on this one! Schedule your private tour today.

48 Bon-Haven Ave, Winchester
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