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$209,000
3 Beds ⋅ 1 Baths ⋅ 26020135 MLS
This beautiful home is located just minutes from historic downtown Winchester. It has 3 spacious bedrooms and 1 full bath. The home has a new roof. When you walk out back you will find an oversized garage. The huge backyard is all fenced in. Make an appointment to tour this one before it's gone.

32 Jackson St, Winchester
$498,000
4 Beds ⋅ 3 Baths ⋅ 26019848 MLS
Discover the perfect blend of privacy, comfort, and country elegance on nearly 6 acres of beautiful Kentucky land. This stunning 4 bedroom, 2.5 bath home offers the lifestyle buyers dream of — complete with a sparkling inground pool, generous outdoor space, and thoughtful updates throughout. Set in a peaceful rural setting yet conveniently located just 8 minutes from the Winchester Bypass and 15 minutes from Mt. Sterling, this property delivers the best of both worlds: tranquility and accessibility. From the inviting living spaces to the expansive grounds ideal for relaxing, entertaining, or simply enjoying the view, this home is truly one of a kind. Opportunities like this don't come often — this one will move fast. Don't miss your chance. Call today to schedule your private showing.

1780 Stoner-Ephesus Rd, Winchester
$380,000
3 Beds ⋅ 2 Baths ⋅ 26019273 MLS
Welcome to 125 Amiens Boulevard, where quality craftsmanship, thoughtful design, and everyday comfort come together in one exceptional home. Built by respected local builder Marcus Moore, this beautifully maintained all-brick ranch has been lovingly cared for and is truly move-in ready. From the moment you arrive, you'll appreciate the inviting curb appeal, spacious floor plan, and attention to detail throughout.The open-concept living area creates the perfect setting for entertaining or relaxing at home, while the well-designed kitchen offers abundant cabinetry, generous workspace, and appliances that convey with the home, making your move that much easier. Buyer to verify listing details. See attached improvements in documents.

125 Amiens Blvd, Winchester
$369,000
3 Beds ⋅ 2 Baths ⋅ 26019263 MLS
This three bedroom home has been updated, new painting interior and exterior, new flooring, new light fixtures, new bath vanities, new granite in kitchen plus much more. Owner/Broker

11 Stoney Brook Dr Unit 1, Winchester
$272,900
3 Beds ⋅ 2 Baths ⋅ 26019259 MLS
Welcome home to this beautifully maintained 3 bedroom, 2 bath home offering comfort, style and fantastic outdoor living! The spacious two-car garage provides plenty of room for parking and storage, while the fully fenced backyard with a new privacy fence creates the perfect space to relax or entertain. Step outside to enjoy the inviting covered outdoor entertaining area, complete with lighting and a small refrigerator-ideal for grilling, hosting friends, or enjoying quiet evenings at home. You'll also appreciate the screened-in back patio, offering a peaceful place to unwind while overlooking the beautifully landscaped yard. The property features mature fruit trees, including a peach and apple trees, adding both charm and seasonal enjoyment. With attractive landscaping surrounding the home and thoughtful outdoor amenities, this property is ready for you to move-in and enjoy. Don't miss the opportunity to make this wonderful home yours!

316 Buffalo Trce, Winchester
$229,000
3 Beds ⋅ 2 Baths ⋅ 26019206 MLS
Charming 3 bedroom, 2 bath home situated on a large, level lot! Relax and enjoy the inviting covered front porch, perfect for morning coffee or evening unwinding. Inside, you'll find a spacious living room and dining room featuring beautiful hardwood floors that add warmth and character. The generous yard offers plenty of space for outdoor entertaining, gardening, play or future possibilities. Don't miss the opportunity to make this delightful property your new home!

13 Long Ave, Winchester
$315,000
3 Beds ⋅ 2 Baths ⋅ 26019157 MLS
Enjoy peaceful country living on this beautiful 2+ acre property featuring a nearly new manufactured home and a spacious barn. Surrounded by scenic countryside views, this property offers plenty of privacy, comfort, and room to enjoy the outdoors. The well-kept home provides a cozy place to relax, while the large barn and open space give you plenty of options for storage, hobbies, gardening, animals, or recreation. Take in quiet mornings, beautiful sunsets, and the charm of wide-open spaces while still being close to nearby amenities. A great opportunity to own a slice of the country and make it your own.

4305 Old Boonesboro Rd, Winchester
$429,000
3 Beds ⋅ 3 Baths ⋅ 26019133 MLS
Welcome to this superbly maintained home located in one of the area's most desirable neighborhoods. Offering 11 spacious rooms, this property delivers exceptional comfort, versatility, and charm. A beautiful front wrap around covered porch creates an inviting first impression, perfect for relaxing or greeting guests. The rear of the home features a covered back porch and an adjoining open deck, ideal for outdoor dining, entertaining, or enjoying peaceful evenings. An outbuilding provides valuable additional storage or workspace. Convenience is unmatched—you're just a few minutes from shopping, restaurants, golf courses, and the bypass, making daily living effortless while still enjoying the tranquility of a well established community. This home truly has so much to offer and is a must see for buyers seeking comfort, location, and lifestyle.

322 Calmes Blvd, Winchester
$410,000
4 Beds ⋅ 2 Baths ⋅ 26017258 MLS
Classic Williamsburg inspired home with charming dormers, timeless character, and an exceptional location that's a short walk to historic downtown Winchester. This spacious 4-bedroom , 2 bath home offers a flexible floor plan with 2 main-level bedrooms and a full bath, plus two additional bedrooms and a full bath upstairs. Enjoy elegant formal living and dining rooms, a large home office, and a bright Florida room overlooking established flower gardens. The spacious eat-in kitchen features abundant cabinetry, a butler's pantry, and plenty of room for family gatherings and entertaining. Beautiful original hardwood floors flow throughout much of the home. The main level bathroom showcases distinctive brick flooring, adding unique character. Custom window treatments and ceiling fans throughout the home are included. You will love the abundant storage throughout the home! Four walk-in closets, including one oversized space that could be used as a nursery or dressing area. The unfinished basement offers endless possibilities for additional living space, a workshop, or recreation and inclues a storm shelter for added peace of mind. This home is just minutes from I-64, country clubs, schools, shopping, dining and everyday conveniences. Combining classic Williamsburg architecture, generous living spaces and original details, this is a rare opportunity to own a truly special home.

351 Boone Ave, Winchester
$209,900
3 Beds ⋅ 1 Baths ⋅ 26019005 MLS
Welcome to this charming newer construction home nestled on a quiet dead-end street in Winchester! Offering 3 bedrooms and 1 full bath, this move-in-ready home features a bright, functional layout with modern finishes throughout. A standout feature is the spacious crawlspace, providing an abundance of storage for seasonal items, tools, or outdoor equipment. Enjoy the peace and privacy of low-traffic living while still being conveniently located near shopping, dining, and local amenities. Whether you're a first-time homebuyer, downsizing, or looking for an investment opportunity, this home is one you won't want to miss!

30 Hughes Ave, Winchester
$239,995
3 Beds ⋅ 2 Baths ⋅ 26018986 MLS
Enjoy small town living! This 3-bedroom 2 bath budget friendly home is ready and waiting for new owners. The unique loft space adds additional space to make it your own. Sitting on just under a third of an acre which will provide a lot of outdoor space to enjoy with friends and family. The backyard is fenced for convenience and privacy. Run from the routine of renting and enjoy home ownership in this cute home. Less than 5 minutes to I64 and close to Winchester dining and shopping.

22 Apache Trl, Winchester
$465,000
3 Beds ⋅ 2 Baths ⋅ 26018911 MLS
Nestled on 8.9 picturesque acres just off Boonesboro Road, this one-of-a-kind property offers the perfect blend of character, privacy, and endless potential. Whether you're dreaming of a horse farm, hobby farm, or simply room to roam, this beautiful property provides plenty of space for horses, livestock, gardening, or enjoying peaceful country living. Inside, you'll find a spacious open-concept kitchen that flows into a stunning vaulted-ceiling living room, where a floor-to-ceiling rock fireplace creates a warm and inviting focal point. Expansive windows fill the home with natural light while framing beautiful views of the surrounding acreage. The thoughtfully designed layout features 3 bedrooms and 2 full bathrooms, including a private second-floor primary suite that offers a peaceful retreat from the rest of the home. Just off the back of the home, the sunroom is the perfect place to enjoy your morning coffee or relax while taking in the sunset over your property. The basement offers over 1,350 square feet of unfinished space and is already plumbed for an additional full bathroom, providing endless possibilities for future expansion. Whether you envision additional bedrooms, a second living area, a game room, home gym, or the ultimate entertaining space, it's ready for your personal touch. If you've been searching for a property that offers acreage, character, and room to grow, this rare opportunity is one you won't want to miss. Schedule your private showing today!

1024 Flanagan Station Rd, Winchester
$789,000
3 Beds ⋅ 2 Baths ⋅ 26018078 MLS
**Drone video and outside pictures available.** Enjoy the space and privacy you've been searching for at 6500 Mount Sterling Rd. Situated on a beautiful rural setting, this property offers the tranquility of country living while remaining conveniently close to Winchester and Lexington. Located less than a minute off exit 101 on I-64. The gorgeous property offers plenty of room for horses, gardening, recreation, or simply taking in the scenic views, this property is ready for you to make it your own! The detached garage has a second floor office area. There are four other outbuildings for horses, hobbies, or equipment storage. Plenty of fenced areas for horses or other farm animals. The gated entrance provide privacy and security. A rare opportunity to enjoy Kentucky living at its best!

6500 Mount Sterling Rd, Winchester
$179,900
3 Beds ⋅ 2 Baths ⋅ 26017853 MLS
Welcome to 76 Clay Street in Winchester—a beautifully remodeled 3-bedroom, 2-bath home that combines modern style with everyday comfort. Completely renovated and move-in ready, this home offers quality updates throughout. Inside, you'll find durable luxury vinyl plank flooring, abundant natural light from all-new windows, and a beautifully updated kitchen featuring butcher block countertops, a farmhouse sink, and stainless steel appliances. The spacious primary suite includes a stunning tiled walk-in shower, creating the perfect private retreat. Major mechanical updates provide added peace of mind, including a new HVAC system and a new water heater. Outside, enjoy relaxing on the inviting covered front porch or entertaining guests on the back deck. This stunning home offers the perfect blend of modern updates, quality craftsmanship, and comfortable living spaces. With everything already completed, 76 Clay Street is truly move-in ready and waiting for you to call it home. Schedule your showing today and experience all this beautifully renovated property has to offer!

76 Clay St, Winchester
$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
$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
$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
$374,900
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
$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
$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