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$234,900
3 Beds ⋅ 2 Baths ⋅ 26018492 MLS
*NEW ROOF!* Welcome home to this well-maintained 3-bedroom, 2-bath brick ranch offering easy one-level living in a convenient location close to shopping, dining, parks, and the community pool. The spacious open family room flows into the kitchen, featuring bamboo wood flooring, a large granite island, newer stainless steel appliances, and a gas range—perfect for everyday living and entertaining. Step outside and enjoy your own Aurora above-ground pool, just in time for summer fun! The partially fenced backyard also includes an oversized storage/tool shed, providing plenty of room for hobbies and extra storage. Enjoy peace of mind with major updates, including a newer HVAC system, water heater, Window World windows (approximately 5 years old), and a new roof with a 5-year warranty. As an added bonus, the seller is offering up to a $2,500 flooring allowance with an acceptable offer. Please include the flooring allowance in any written offer. Don't miss the opportunity to make this inviting home yours!

528 Estes Dr, Winchester
$524,900
3 Beds ⋅ 3 Baths ⋅ 26018460 MLS
OK! WOW!!! Location is yes, yes, yes! This house is located in a quiet residential neighborhood and in minutes you can be at the I-64 or I-75 interstate corridors. OK enough about location. This house is pristine! The owners have improved the property with new dimensional style roof shingles in 2025 along with new gutters. They have freshly painted the interior. They have added a new refrigerator, stove, microwave and a washer and dryer. The owners have meticulously maintained this house throughout. From the entrance foyer note the gleaming wood flooring and the fresh paint on the 9' foot ceiling walls, the vaulted great room and the crown molding. The split bedroom concept is great for guests or a home office. And above the garage is a bonus room measuring 420 sq ft. Entertaining or relaxing on the covered back patio that overlooks the beautiful Kentucky Bluegrass is a must. And bonus, the property is adjacent to a church property that is mowed for a walking path. Make an appointment to see this house today, it may be your new home.

275 Runnymeade Dr, Winchester
$286,000
3 Beds ⋅ 2 Baths ⋅ 26018346 MLS
Welcome home to this beautifully renovated home in the desirable Bon Haven subdivision! From the moment you step inside, you'll appreciate the bright and inviting living room that flows seamlessly into the updated kitchen, creating a warm and functional space for everyday living. The main level features two spacious bedrooms and two full bathrooms, while the second floor offers a private third bedroom; perfect for a guest room, home office, or primary retreat. The unfinished 780-square-foot basement provides endless possibilities for additional living space, a recreation room, or extra storage. Located within walking distance of the popular Legacy Grove Park, you'll enjoy easy access to walking trails, green space, and outdoor recreation. Move-in ready and thoughtfully renovated, this home is ready for its next owner.

33 Bon-Haven Ave, Winchester
$235,000
2 Beds ⋅ 2 Baths ⋅ 26018337 MLS
Country living with the convenience of being in the city! This rare find offers over an acre of land inside the Winchester city limits with beautiful views of surrounding farmland. Relax on the spacious partially covered back deck, entertain family and friends, or enjoy plenty of room for gardening, pets, and play. The home features 2 bedrooms, 1.5 baths, and approximately 1,039 square feet of living space on the main level. The finished upstairs adds approximately 385 square feet divided into two bonus rooms currently cooled with a window A/C unit. With the addition of a permanent heat source, this space could easily serve as additional bedrooms, a home office, hobby room, or flex space. Outside you'll find an impressive detached 3-car garage with plenty of room for vehicles, a workshop, or storage, plus a separate storage building for even more space. A remote-controlled gated driveway adds convenience, privacy, and security. If you've been searching for a property that offers the feel of the country while enjoying the convenience of city living, this one checks all the boxes. Potential for second home site! Schedule your private showing today!

47 Hughes Ave, Winchester
$294,900
5 Beds ⋅ 3 Baths ⋅ 26018116 MLS
If you've been looking for an amazing "light" renovation opportunity, this is it! Over 3300 sq ft w tons of character situated on an acre of land w gorgeous mature trees. *Seller's are contributing $5,000 towards buyer's prepaids/closing costs.* Flooring, roof, HVAC heat pumps are under 6 years old. New windows & gutters installed May 2026. Under 5 minutes to 64. Don't let this one pass you by. Come check this property out for yourself!

4603 Paris Rd, Winchester
$147,900
3 Beds ⋅ 1 Baths ⋅ 26017859 MLS
Charming and move-in ready! This freshly renovated 3-bedroom, 1-bath home in downtown Winchester offers all-new flooring and fresh paint throughout. The spacious eat-in kitchen provides plenty of room for gathering, and the in-unit washer/dryer hookup adds everyday convenience. Situated on a quiet street directly across from a park and within walking distance of the elementary school, this home offers a peaceful, family-friendly location. Enjoy the fully fenced backyard and central heat and air for year-round comfort. Ready for immediate occupancy! schedule your private tour today!

118 Park Ave, Winchester
$1,950,000
26018115 MLS
Located directly across from the Clark County Hospital this 12,042 office building has been occupied by the Clark County Board of Education since 1969. There is an additional 4,092 sf building located behind the main office that has been finished with office and storage space. This incredible location could be the right site for a multi-tenant renovation, single-use office, or a new beginning.

1600 W Lexington Ave, Winchester
$749,900
3 Beds ⋅ 3 Baths ⋅ 26017698 MLS
Welcome to peaceful country living on 7.14 beautiful acres in Winchester! Built in 2022, this custom one-level home offers 3 bedrooms, 2.5 bathrooms, and 2,735 square feet of thoughtfully designed living space. The open floor plan features hardwood flooring, a spacious great room with a gas fireplace, and a stylish kitchen with a large island and ample cabinetry. The split-bedroom layout provides privacy, while the primary suite offers a spa-like bath and walk-in closet. Enjoy scenic views from the covered porch and the convenience of an attached two-car garage, all while being just a short drive to Winchester, Paris, and Lexington. This is the perfect blend of modern comfort and peaceful country living. Schedule your showing today!

2180 Big Stoner Rd, Winchester
$319,900
5 Beds ⋅ 2 Baths ⋅ 26017629 MLS
Welcome to 128 Cherokee Drive, where space, versatility, and convenience come together! This all-brick split-foyer home offers 5 bedrooms, 2 full bathrooms, and over 2,000 square feet of comfortable living space, making it ideal for growing families, multi-generational living, or anyone needing extra room. The main level features a bright and inviting living room, while the finished lower level offers a second spacious living area—perfect for a family room, game room, home office, or guest retreat. An exterior entrance to the basement adds flexibility and convenience. Situated in an established neighborhood just minutes from shopping, dining, schools, and other everyday amenities, this home combines a desirable location with a functional layout that's ready to fit your lifestyle. Don't miss your opportunity to make this Winchester home your own! Updates include new furnace, new kitchen appliances (7/17 delivery) and additional kitchen cabinets, additional insulation, and first floor bathroom plumbing updates.

128 Cherokee Dr, Winchester
$225,000
3 Beds ⋅ 4 Baths ⋅ 26017061 MLS
This beautifully maintained 3 bedroom, 3.5 bath townhouse offers the perfect blend of comfort, convenience, and low-maintenance living. Ideally situated in a desirable location, this spacious home features a functional floor plan with generous living areas, well appointed bedrooms, and a bathroom for each bedroom, providing comfort and privacy for family and guests alike. Enjoy the benefits of townhouse living with less exterior maintenance, all while being just minutes from shopping, restaurants, schools, and everything Winchester has to offer. Whether you're a first time homebuyer, or searching for an investment opportunity, this move in ready home is one you won't want to miss!

128 Abbeywood Ct, Winchester
$515,000
26002170 MLS
This versatile mixed-use property offers a rare opportunity to combine business potential with built-in residential income. Formerly operated as a neighborhood market, the commercial building spans over 3,000 square feet and is thoughtfully equipped with a full kitchen and laundry area, making it ideal for a wide range of business concepts. Whether you envision a café, restaurant, retail shop, office space, event venue, service-based business, or creative studio, the layout and infrastructure provide a flexible foundation ready to be reimagined. With strong visibility and a neighborhood presence, this property is well-positioned for an owner-operator or investor seeking adaptability and long-term value. Adding to its appeal is the separate 3-bedroom residential home located at 35 Hays, which is currently income-producing and leased through 2027. This creates an immediate revenue stream while you develop, occupy, or lease the commercial space a powerful advantage for offsetting costs or maximizing returns. Opportunities like this offering commercial flexibility, residential income, and long-term potential are increasingly rare. Whether you're expanding a business, launching something new, or investing with vision, this property delivers the space, structure, and upside to make it happen.

35-37 Hays St, Winchester
$780,000
25015685 MLS
This money making car wash has three drive in bays and one automatic wash. Included with the sale is a vibrant oil change business which occupies two bays.

126 Shoppers Dr, Winchester
$229,900
3 Beds ⋅ 2 Baths ⋅ 26017144 MLS
Welcome home to this charming 3-bedrooms, 2-bath ranch perfectly situated in the heart of Winchester! Offering the convenience of one-level living, this inviting 1200 sq ft home combines comfort, functionality, and an unbeatable location. Primary bedroom is en suite and offers plenty of closet space. Additional 2-bedrooms and 1-bath provide plenty of space. Enjoy easy access to schools, shopping, restaurants, parks, and local amenities—all just minutes from your front door. Inside, you'll find a spacious and welcoming open floor plan with comfortable living areas, generously sized bedrooms, and plenty of natural light throughout. Whether you're a first-time home buyer, looking to downsize, or searching for the perfect home, this property offers endless potential to make it your own. Don't miss this opportunity to own a well-located home that puts everything you need within reach.

491 Hidden Hills Way, Winchester
$326,000
26017069 MLS
Escape to the peace and privacy of this beautiful 48.54-acre unimproved property in a remote rural setting. Featuring a mix of rolling pasture and wooded acreage with gentle slopes, this versatile tract is ideal for farming, cattle, horses, recreation, hunting, or building your dream country retreat. Whether you're looking for productive agricultural land or a private getaway, this property offers endless possibilities in a scenic countryside setting. Call to schedule your private viewing!

380 Howard Creek Rd Unit 380, Winchester
$364,900
3 Beds ⋅ 2 Baths ⋅ 26016576 MLS
Welcome to this beautifully maintained all-brick home nestled in one of Winchester's most established and desirable neighborhoods. Offering over 2,200 square feet of living space, this 3-bedroom, 2-bath home blends timeless character with thoughtful updates. The main level features a spacious family room with a cozy fireplace, custom cabinetry and new granite countertops in the kitchen, and a versatile dining room that can also serve as a home office. Don't miss the relaxing all-seasons room overlooking the professionally leveled and graded yard—perfect for morning coffee or evening gatherings. Upstairs, the private primary suite offers a generous bedroom, full bath, and three walk-in closets. An unfinished basement provides abundant storage or the opportunity to expand your living space. Conveniently located just minutes from historic downtown Winchester, the bypass, shopping, dining, and I-64, this move-in ready home offers comfort, charm, and exceptional convenience.

15 Moundale Ave, Winchester
$409,500
3 Beds ⋅ 2 Baths ⋅ 26016762 MLS
215 Delaplain Road is the kind of home where pride of ownership is easy to see. Inside, you'll find 3.25-inch hand-scraped hardwood flooring throughout, travertine tile in both bathrooms, updated vanities, newer light fixtures, and a beautifully tiled walk-in shower with a custom glass door in the primary bath. The kitchen offers added cabinetry/wet bar space, a newer refrigerator, and a gas line already in place if you'd like to convert the stove to gas. One of the best features of the home is the custom 4-seasons sunroom, complete with Eze-Breeze four-track windows, ceramic tile flooring, recessed lighting, a tray ceiling, a ceiling fan, and a cabana door overlooking the backyard. The lot is a true highlight, with outdoor lighting, low-maintenance landscape rock, a concrete walkway, and a shop/outbuilding that stays with the property. Major system ages include the roof, replaced in 2018, and the HVAC, installed in 2017. Additional updates include replacement windows throughout, a custom front door, a double garage door with an opener and keypad entry, gas logs, and updated laundry room cabinetry with pull-out shelving. Thoughtfully cared for and improved over the years, this home offers comfortable everyday living with spaces you'll enjoy in every season.

215 Delaplain Rd, Winchester
$219,900
26016689 MLS
Discover the possibilities with this unique dual-property offering at 3686 & 3688 Crowe Ridge Road. Enjoy the peace and privacy of a beautiful country setting with room to spread out and endless potential. Whether you're looking for a primary residence with additional living space, an investment opportunity, or housing for extended family, this property offers versatility that's hard to find. Conveniently located just minutes from Winchester off the Mountain Parkway, exit 10, and an easy commute to Lexington.

3686 Crowe Ridge Rd, Winchester
$139,000
2 Beds ⋅ 2 Baths ⋅ 26005794 MLS
Ready to Stop Renting? Your Opportunity Is Here Step into the comfort and freedom of homeownership with this spacious, well maintained 2-bedroom, 2-bath modular home — and yes, the lot is included. An attached room addition provides even more flexibility, easily adaptable into a third bedroom, home office, hobby room, or bonus space to suit your lifestyle. --- Interior Highlights • 2 full bathrooms • Large walk in shower • Wheelchair ramp for easy accessibility • Generous closet space throughout • Ample kitchen counter space • Clean, comfortable, and truly move in ready --- Exterior Features • Large corner lot offering extra privacy • Parking for up to 4 vehicles • Outbuilding for additional storage • Equipped with a Generac backup generator for peace of mind during outages --- This home offers affordable living without compromise—space, accessibility, convenience, and the security of owning your own land. $149,000

404 Mount Vernon Dr, Winchester
$1,200,000
25502866 MLS
 Prime I-1 Zoned Industrial Property - Winchester, KY Unlock the potential of this exceptional 3.9-acre parcel located in the heart of Winchester's thriving industrial corridor. Zoned I-1 (Clean Industrial), this property offers flexibility for a wide range of uses—from manufacturing and warehousing to logistics and tech operations. Property Highlights: * 3.9 Acres of flat, usable land * 7,800 Sq Ft Building with high ceilings and open layout * Power Garage Doors for easy access and loading * Utility-Ready with ample power supply * Strategic Location with quick access to major highways and local infrastructure Whether you're expanding your business, launching a new venture, or investing in a high-potential asset, this property delivers the space, zoning, and location to make it happen. The possibilities are endless—don't let this opportunity pass you by!

101 Jefferson St, Winchester
$199,000
26009146 MLS
Escape to your own private retreat with this stunning 41.6± acre wooded tract nestled in the scenic countryside of Winchester, Kentucky. This expansive property offers a rare opportunity to own a secluded slice of nature, perfect for a private estate, recreational getaway, or hunting retreat. With rich with mature timber, this land presents a lot of natural beauty. A network of cleared trails and old roadbeds provides easy access throughout the property, making it ideal for exploring, hiking, or ATV use. Whether you're looking to build your dream home tucked among the trees or create a peaceful weekend escape, this property delivers the privacy and tranquility you've been searching for. A small barn adds utility, while the location offers convenient access to the Mountain Parkway, making travel to Winchester and surrounding areas simple and efficient. Don't miss this opportunity to own a versatile piece of Kentucky land with endless possibilities—recreation, investment, or your future homesite all in one.

2697 Pine Ridge Rd, Winchester
$365,900
3 Beds ⋅ 2 Baths ⋅ 24018286 MLS
New Construction, come view, great house plan, ranch on a crawl space, 3 bedrooms, 2 bath, you will love this inviting neighborhood, plan shown on line could vary, this is a spec home, all the colors have been decided, fixtures, flooring, brick, siding, cabinets, countertops have been ordered, restrictions apply, no HOA, buyer to verify sq ft of home and lot. This home is close to I-64, I-75, Lexington, Richmond, shopping, churches, hospital and schools, pictures to follow as home is being constructed.

206 Jett Dr, Winchester
$124,500
2 Beds ⋅ 1 Baths ⋅ 26000228 MLS
Investment Opportunity or Perfect Starter Home This charming 2-bedroom, 1-bath property is full of potential! With a strong rental history and an excellent lease track record, it's ideal for investors or first-time buyers. The home requires only light maintenance, and the seller is even willing to fund minor repairs. Don't miss your chance to own a property with great value and endless possibilities! Property is AS IS! Bring me a offer.

122 Callaway Street Se Callaway Street, Winchester
$329,900
5 Beds ⋅ 4 Baths ⋅ 26012369 MLS
Whether you're looking for a large residential home, investment opportunity, business potential, or a combination of uses, this property is ready to fit your vision. Featuring 5 bedrooms, 4 baths, soaring 10 foot ceilings, and a welcoming front porch, this unique property blends character, space and versatility. Generous room sizes, timeless charm, and flexible living spaces make it ideal for multi-generational living, rental income opportunities, or for a great work setup. Opportunity with unlimited potential.

410 W Lexington Ave, Winchester
$265,000
3 Beds ⋅ 1 Baths ⋅ 26012905 MLS
Come Home to Sunset!!!! Brick Ranch home, with 2 driveways, 3 bedrooms, 1 bathroom, Open Living Room, Dining Room and Kitchen Area, Spacious Laundry Room, Covered back patio for outdoor living! Beautiful Hardwood floors, updated bathroom and kitchen, exceptional location, building out back for he shed or she shed or storage, move in and enjoy the sunset!

119 Sunset Hts, Winchester
$1,500,000
4 Beds ⋅ 3 Baths ⋅ 26016393 MLS
Welcome to a truly one-of-a-kind Kentucky estate where luxury, craftsmanship, and country living come together on 27 breathtaking acres in Clark County—just 10 minutes from the interstate for an easy commute while still enjoying complete privacy. Built with exceptional quality and thoughtfully designed by its original owner, this custom home offers over 7,000 square feet of living space with 4 spacious bedrooms, 3 full bathrooms, and two additional finished rooms in the walkout basement that provide incredible flexibility for guest space, a home gym, office, hobby rooms, or other uses. From the moment you step inside, you'll appreciate the attention to detail. Brazilian Tigerwood flooring flows throughout the main level, while engineered flooring extends through the basement. The inviting living room is anchored by a gas fireplace, creating the perfect gathering space, while the home's two full kitchens make multigenerational living, entertaining, or hosting guests effortless. The custom bar showcases beautiful copper accents, including a stunning copper backsplash that adds warmth and character. The primary suite serves as a private retreat with a luxurious soaking tub and its own sunroom—a peaceful space to enjoy your morning coffee while overlooking the surrounding countryside. Built for both comfort and efficiency, this home features geothermal heating and cooling, an in-home dehumidifier, a security system, automated gated entry, and robust 2x12 floor joists, reflecting the superior craftsmanship found throughout. Outside, the opportunities are endless. A massive 50' x 64' insulated shop and a 14-foot garage door is ideal for equipment, RV storage, business operations, or workshop space. The above-ground pool provides the perfect place to unwind during the summer months, while the fully fenced property is currently home to cattle but offers endless possibilities for horses, farming, recreation, or simply enjoying your own private slice of Kentucky. Whether you're searching for a luxury family estate, an equestrian property, a working farm, or a private retreat with room to grow, this remarkable property delivers a rare combination of quality construction, thoughtful amenities, and unmatched versatility—all within minutes of modern conveniences.

351 Benton Road Mt, Mt Sterling
$165,000
4 Beds ⋅ 3 Baths ⋅ 26008701 MLS
Investor special with historic charm on corner lot! Opportunity awaits with this spacious 5 bedroom, 3 full bath home offering 3,462 sq ft of potential. Situated on a corner lot and walkable to downtown, this classic 2 story property is rich in character, featuring original hardwood floors, detailed woodwork, a welcoming front porch with columns, and a striking staircase with stained glass accents. The home has been partially gutted, with the kitchen, bathrooms, and several rooms ready for renovation, making it an ideal project for investors, flippers, or buyers looking to customize their dream home. With solid bones and timeless architectural details throughout, this property is primed to be transformed into a true showpiece. Cash or renovation financing required. Inspections welcome but selling AS-IS. Bring your vision and unlock the full potential of this one of a kind property.

229 S Highland St, Winchester
$225,000
26005737 MLS
Wonderful 24 acre retreat with gentle sloping land, and a creek bed running thru part of the front portion of the lots (6.1 acre parcel & 18.4 acre parcel at the rear). Build your dream home or just use as recreational or farm land until you do. 1 1/2 miles to the first exit on the Mountain Parkway exit #10. 12 miles to I-64 at Winchester. See attached pictures & plat/overhead pictures.

3934 Trapp-Goffs Corner Rd, Winchester
$225,000
4 Beds ⋅ 1 Baths ⋅ 26013563 MLS
Nestled in a well-established neighborhood filled with charm and character, this inviting all-brick home offers the warmth and comfort you've been looking for. Featuring 4 bedrooms and 1 bath, the thoughtfully designed layout includes a primary bedroom and second bedroom on the main floor, with two additional bedrooms upstairs, providing flexibility for family, guests, or a home office. Beautiful hardwood floors add timeless character throughout much of the home, while the kitchen is equipped with stainless steel appliances and plenty of space for preparing meals and gathering with loved ones. The solar panels help keep utility costs low, making this home as efficient as it is welcoming. Outside, you'll find a wonderful fenced backyard that feels like a private retreat, complete with a chicken coop, storage shed, and plenty of room for gardening, pets, play, or relaxing evenings outdoors. A 1-car garage provides additional storage and convenience. With its classic all-brick construction, cozy atmosphere, mature surroundings, and practical updates, this home offers a perfect blend of comfort, character, and everyday living in one of Winchester's quaint established neighborhoods.

120 Windsor Dr, Winchester
$575,000
23015571 MLS
Ideally located along the heart of Bypass Road (ADT: 24,801) in Winchester, Kentucky between and surrounding Kroger and Walmart shopping centers. These lots are offered as 1+ acres and may be subdivided. Winchester, KY is the county seat of Clark County, KY and is part of the Lexington-Fayette KY Metropolitan Statistical Area, and is supported by such industries such as Amazon, Ale-8-One, and Catalent Pharmaceuticals. Second Row Lots conveniently located along residential density while being visible from the Bypass. Conceptual Plans have been created which display potential uses of up to 22,800 SF as retail box. Would be a great location for retail, office, storage, and mixed use development. Conceptual Development Plan: https://www.kcrea.com/files/property/6900000/6902843/25814078_2020___Conceptual_Development_Plan_Lots_3.pdf

529 Bullion Blvd Unit 3B, Winchester
$549,900
3 Beds ⋅ 2 Baths ⋅ 26010352 MLS
Nearly new French country ranch that has been gently lived in. This classy home has magnificent curb appeal. When you walk through the front door you are welcomed by a tasteful foyer area. Stroll into the wide-open space of the great room with a towering, coffered ceiling and tons of natural light. The gas fireplace adds a nice focal point to the living space. The kitchen space is equipped with all stainless appliances including a gas range for cooking those delicious meals. The large kitchen overlooking the great room offers the convenience of an eat in bar area, delightful dining space, a huge hidden pantry and a unique kitchen niche to make it your own unique space for a possible coffee bar. This home is all about convenience and privacy with the split bedroom concept. Lots of space in the primary bedroom for your king size bed plus a nice sitting area. You will love the huge primary bath with stylish custom tile and the adjoining generous sized closet for the fashionista. In edition there are two guest bedrooms with a full bathroom. There is an additional flex room that makes a great office space or a 4th bedroom. The large laundry area and drop zone is an added convenient feature to the home. From enjoying your morning coffee, evening relaxation or outdoor gatherings the large covered back patio is the place to be with the outdoor fireplace. You will love the large 2-car oversized garage. This home has so much to offer! Convenient to local shopping, restaurants, I64, 17 miles to Man o' War Blvd Lexington and 28 miles to Bluegrass Airport. Schedule your tour today to check out this beautiful home. Now is your chance to own this nearly new home.

108 Bella Shae Way, Winchester