Winchester Homes for Sale

Winchester Homes for Sale

Welcome to Winchester, Kentucky, a charming city nestled in the heart of Clark County. Known for its rich history, friendly community, and picturesque landscapes, Winchester offers a unique blend of small-town charm and modern amenities. As one of Kentucky's hidden gems, this city boasts a vibrant downtown area filled with delightful shops, local eateries, and cultural attractions that reflect its deep-rooted heritage.

Winchester is not only a great place to live but also a fantastic community for families, retirees, and professionals alike. With its excellent schools, numerous parks, and recreational facilities, residents enjoy a quality of life that is both fulfilling and affordable. The city's convenient location, just a short drive from Lexington, provides easy access to a larger metropolitan area while maintaining the tranquility of suburban living.

For those considering a move to this beautiful city, there are a variety of homes for sale that cater to diverse tastes and budgets. From charming historic houses with character to modern new builds that offer the latest in design and technology, Winchester's real estate market has something for everyone. Whether you’re looking for a cozy family home, a spacious property with land, or a low-maintenance townhouse, you’ll find an array of options that make it easy to settle down in this welcoming community.

Explore the homes for sale in Winchester today and discover why so many are choosing to call this delightful city their new home. With its warm community spirit and beautiful surroundings, Winchester is not just a place to live; it’s a place to thrive.

Newest Winchester Homes for Sale

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. Will be REHAB type loan

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
654 Pine Rdg, Winchester
$275,000
4 Beds ⋅ 2 Baths ⋅ 26029056 MLS
Picture slow mornings with coffee and a quiet tree line, evenings with a fishing pole at the pond, and the convenience of town still close by. 654 Pine Ridge Road sits on 8 acres in Winchester, giving you the space and privacy of country living without giving up easy access to everyday errands. Two acres are fully cleared and ready for your vision, while the remaining 6 wooded acres offer natural privacy and room to explore. A pond shared with a neighbor means fishing is part of everyday life here. The lightly updated mobile home by Clayton Homes features 4 bedrooms and 2 full baths, so the comfort inside matches all the room outside. Seller has replaced roof, water heater, installed a new sidewalk, new flooring & multiple light fixtures. If you've been looking for land, quiet, and convenience in one place, this property delivers all three. Call today to schedule your private showing.

654 Pine Rdg, 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
121 Ralston Ln, Winchester
$56,700
3 Beds ⋅ 1 Baths ⋅ 26029234 MLS
INVESTMENT OPPORTUNITY — BUILD YOUR VISION! The existing home is in poor condition and may be suitable for renovation or a tear-down project. The property consists of almost 1/2 Acre (.45 acre) with a newer metal building 20 X 25. An excellent opportunity for investors, builders, or buyers looking to create something new! This could be an excellent place for storing equipment, boats, RVs, or other recreational toys! 1,000-gallon septic system installed in 2023.

121 Ralston Ln, Winchester
7440 Bybee Rd, Winchester
$519,900
5 Beds ⋅ 3 Baths ⋅ 26029059 MLS
*Owner Agent Welcome to this spacious 2023-built, manufactured home situated on 6.54 beautiful acres in Winchester, Kentucky. Offering 5 bedrooms and 3 full bathrooms, this home provides plenty of space for family, guests, and comfortable everyday living. The property combines the convenience of a newer home with the beauty and privacy of acreage. The land features a natural spring, adding a unique country-living feature and providing an additional natural water resource on the property. A detached one-car garage provides valuable space for parking, storage, hobbies, or a workshop. With 6.54 acres, there's plenty of room to enjoy the outdoors, garden, hobby farm, animals such as horses, goats, chickens or turkeys, have recreational space, or simply take in the peaceful surroundings. The property also offers very limited restrictions. The only known restriction is that no obstruction may be placed across the easement located along the rear of the property such as gate, fence etc., giving the new owner considerable flexibility in enjoying and utilizing the land. If you've been searching for a newer 5-bedroom home on acreage with a natural spring, detached garage, privacy, and limited restrictions, this property offers a rare combination of features in the Winchester area. Within 20 minutes of Richmond and 30 minutes of Lexington. Driveway easement at very rear of property. Utility easement for water through property with water meter near road. LISTING AGENT OWNS PROPERTY

7440 Bybee Rd, Winchester
314 Botts Ct, Winchester
$299,900
3 Beds ⋅ 2 Baths ⋅ 26028838 MLS
This stunning remodeled 3 bedroom 2 bathroom all brick ranch in Verna Hills subdivision is a must see! From the moment you walk in, your only concern is moving in. The following items have been done: new drywall in 50%+ of the home done to completely remove all wallpaper, new roof, soffit, gutters (2025), new hot water heater, new custom back sliding glass door, crawlspace completely waterproofed with vapor barrier and newly installed sump pump, brand new privacy fence, all new vinyl flooring and paint, completely upgraded kitchen with custom cabinetry, backsplash, quartz countertops, and stainless steel appliances, 2 custom designed bathrooms with custom tile and trim work and all new custom light fixtures. Schedule a showing soon to see this great home!

314 Botts Ct, Winchester
13 Euclid Ave, Winchester
$250,000
3 Beds ⋅ 2 Baths ⋅ 26028494 MLS
Welcome to 13 Euclid, a rare find that keeps the original charm of an older downtown home without the upkeep that usually comes with one. This beautiful one-level, 3-bedroom, 2-bath home still has its character, including soaring 12-foot ceilings and original features. Both full bathrooms have been updated, and a fresh neutral color palette runs throughout. Most importantly, the systems and functional items have been updated, allowing for a more maintenance-free lifestyle, which is truly rare in an older home. The home has a dimensional shingle roof, HVAC, water heater, and sewer line that have all been updated within the past five years. The crawlspace vapor barrier and extra attic insulation were updated as well. Low-maintenance white vinyl siding and 200-amp electrical service complete the impressive improvements. A covered front porch welcomes you into the formal foyer, which is flanked by two bedrooms. One is currently used as a sitting area. From the foyer, you'll flow into the living room and adjacent dining room. Just off the dining space, the primary bedroom has a large closet and a private bath. The spacious kitchen is the heart of the home, equipped with all appliances, and a perfect setting for holiday meals. A home office is ready for working from home, and a mudroom and a large laundry room/pantry add everyday convenience. Step outside to the park-like backyard, which is fully fenced with large mature trees, a wide gate, and a parking pad. It's a gardener's dream, with daffodils, tulips, hyacinths, daylilies, and more blooming through the seasons. Park off the rear lane behind the home or on the street out front for easy access. Please note: All updates per seller, and there are 3 beautiful fireplaces in the home for aesthetic purposes only (non-functional).

13 Euclid Ave, Winchester
131 Teal Ln, Winchester
$617,000
3 Beds ⋅ 4 Baths ⋅ 26028684 MLS
If you're looking for space, character, and a home with plenty of possibilities, this one deserves a look! This beautiful ranch-style home offers a full basement, two garages, and an inviting floor plan with impressive architectural details throughout. Step inside and you'll immediately notice the gorgeous hardwood flooring, detailed trim work, and spacious living areas. The great room features a vaulted ceiling, brick fireplace, and beautiful custom built-in cabinetry. The kitchen offers an abundance of rich wood cabinetry, granite countertops, stainless steel appliances, double ovens, and a breakfast area. A formal dining room showcases elegant wainscoting, crown molding, and a beautiful chandelier, adding character and charm. The screened-in porch provides another great space to relax and enjoy the outdoors. The full basement offers additional space and flexibility, while the two garages provide plenty of room for vehicles, storage, or hobbies. With its generous living spaces, beautiful woodwork, and thoughtful design, this home has so much to offer. Come see the possibilities for yourself! Rony Jo Ballou Broker Auctioneer.

131 Teal Ln, Winchester
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