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$785,000
5 Beds 3 Baths 26019610 MLS
Escape to the peace and privacy of country living with this spacious brick one-and-a-half story home situated on just over 5 acres. With plenty of room to spread out, the main level offers a welcoming foyer, formal dining room, living room with a wood-burning fireplace, kitchen featuring granite countertops, tile backsplash, breakfast nook, and laundry room, along with the primary suite, three additional bedrooms, and another full bath. The primary suite is a true retreat with exposed wood beams, a sitting area, tiled shower, and marble vanity. Upstairs you'll find a fifth bedroom, while the fully finished basement adds even more flexible living space with a second living area, kitchenette, bonus rooms, half bath, and radon mitigation system already in place. Throughout the home you'll find beautiful shiplap accents and a mix of hardwood, tile, vinyl, and carpet flooring. Step outside to enjoy the covered patio, pergola, fire pit, swing, above-ground pool with deck, and playset, all perfect for entertaining or relaxing. The attached two-car garage is complemented by an additional detached garage with its own upstairs space and separate electric meter, offering endless possibilities for a workshop, storage, or future expansion. Thoughtfully updated over the years and offering the perfect mix of space, comfort, and country charm, this property is ready to welcome you home.

217 Wades Mill 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

$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

$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

$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

$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

$245,000
3 Beds 2 Baths 26018026 MLS
Meticulously maintained 3-bedroom, 2-bath home on a full basement with wonderful curb appeal! Beautiful landscaping and a welcoming covered front porch invite you into this charming home. Inside, you'll find a warm and inviting main level featuring handsome hardwood flooring, a cozy fireplace, and a spacious living area. The adorable kitchen offers plenty of cabinet and counter space, making meal prep and entertaining a breeze. Down the hall are three comfortable bedrooms and a full bath. The finished basement provides an expansive second living area with a propane fireplace and a second full bath. This versatile space could easily serve as a fourth bedroom, home office, recreation room, or guest suite. You'll also appreciate the oversized one-car garage with driveway access, offering abundant room for parking, storage, or workshop space. Outside, enjoy the privacy of the fenced backyard complete with a garden area and a large storage building. The location is price with close proximity to both Winchester and Lexington! Please note: The HVAC system is currently not functioning, and the property is being sold "as is" but all inspections are welcomed. Seller requests a minimum of 24-hour response time on all offers.

216 Robyn Dr, 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

$699,000
4 Beds 4 Baths 26017283 MLS
Sellers will be reviewing offers this evening, Sunday, July 12, 2026 PM Rare Opportunity! Offered for the first time in nearly 50 years, this one-of-a-kind property presents endless possibilities in a breathtaking setting. Nestled on just over 8 private, serene acres with stunning views of Boone Creek, this spacious home offers the perfect blend of privacy, natural beauty, and room to grow. This exceptional property offers a true experience with nature, where peace and tranquility create the perfect private retreat. Conveniently located just minutes from shopping, restaurants, and everyday amenities in Hamburg plus easy access to Hospitals, you'll enjoy the rare combination of secluded country living with the convenience of city access. Inside, you'll find 4 generously sized bedrooms, 3 full baths, and a half bath, along with a welcoming great room designed to showcase the incredible creek views. A large spacious kitchen with a center island with bar space seating and a breakfast area overlooking the pool. The large laundry room and versatile bonus room provide additional space that's perfect for a home office, hobby room, or flex space to fit your lifestyle. The second level offers 2 spacious bedrooms that share access to a full bath, incredible storage options, including a huge walk-in closet and an expansive floored attic area perfect for seasonal items, hobbies, or keeping everything organized. Step outside to enjoy the inground pool, complete with a brand-new liner scheduled for installation on July 20, making it ready for seasons of outdoor entertaining and relaxation. Whether you're looking to update, personalize, or simply enjoy this exceptional property as it is, opportunities like this are truly rare. Don't miss your chance to own a private retreat with spectacular Boone Creek views and unlimited potential. Here is your chance to personalize and make it your own. Home needs a little TLC! This home is in Clark County with a Lexington/Fayette County address. Sellers considered remodeling the home a few years back please see attached documents to view the floor plan that they considered. Check out the Zillow Link https://www.zillow.com/homedetails/5349-Athens-Boonesboro-Rd-Lexington-KY-40509/115282711_zpid/?view=public

5349 Athens Boonesboro Rd, Lexington

$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

$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

$312,000
3 Beds 3 Baths 26008021 MLS
Search no more your dream home just hit the market! You will fall in love with this one as soon as you walk through the front door. Beautiful open concept, very modern new home just built in 2022. You're going to love the open kitchen and living room area with the large kitchen island, beautiful stainless steel appliances and granite countertops. Primary bedroom on the first floor with a full bath and nice walk in closet. Picture hosting your social events on the expansive two-level decks located at the back of your new home. If that is not enough this home is perfectly located within waking distance to Kroger & Walmart, shopping and dining. Come be the first to see this one or your likely to regret it. This home has never flooded but as of 2025 it does require flood insurance. The current owner has the flood insuance through ( The Hartford ) insurance company at a cost of $100 a month. Owner is offering to pay $1200 for the new owners first year of flood insurance.

200 Dubuy Dr, Winchester

$329,000
3 Beds 3 Baths 26016008 MLS
Don't let this charming brick ranch fool you—it's what's waiting out back that will absolutely steal the show! Nestled in the heart of Winchester, this 3BR/3BA home offers an incredible backyard oasis that's perfect for entertaining, relaxing, and making memories all summer long. The sparkling in-ground pool is the centerpiece of this private retreat, surrounded by expansive concrete decking and complemented by a covered pool bar with electricity. An additional freestanding deck provides even more room to relax, while the fixed outdoor movie screen creates unforgettable movie nights from the comfort of your pool float. Gather around the fire pit on cool evenings, shoot hoops on the spacious patio, relax in the hot tub, or enjoy hobbies and extra storage in the outbuilding complete with electricity. The fully fenced backyard truly feels like your own private staycation. Inside, the home offers a comfortable and flexible layout. The fully equipped eat-in kitchen features a breakfast bar with a cozy dining/sitting area with fireplace insert that's perfect for easy cooking and entertaining. The main level includes a private primary suite, an additional bedroom, and a second full bath. The finished walkout basement adds exceptional flexibility with a spacious family room that could easily serve as a third bedroom, a full bath, and a bonus room ideal for a home office, exercise room, hobby space, or even a potential fourth bedroom (no egress). A one-car basement garage provides additional storage and convenience. From the street, this home is modest and unassuming—but step into the backyard and you'll discover one of Winchester's best-kept secrets. If you've been dreaming of a home where every day feels like a vacation with an affordable price tag, this is one you won't want to miss!

13 Bel Air Dr, Winchester

$289,000
3 Beds 2 Baths 26007779 MLS
Opportunity awaits at 54 Locust Drive in Wesleyan Park subdivision. This all-brick ranch on a full unfinished basement offers 3 bedrooms, 2 baths, and 1,692 square feet of finished living space, along with an equally spacious basement ready for storage, hobbies, or future possibilities. Built in 1960, this home features hardwood flooring, a 2-car attached garage, and a fenced backyard with a covered patio. The home retains much of its original character and presents an excellent opportunity for a buyer with vision to update the kitchen, baths, and finishes to match their style. With its solid construction, functional layout, and room to make it your own, this property offers a great blend of value, space, and potential at $299,000.

54 Locust Dr, Winchester

$2,999,000
6 Beds 5 Baths 25507353 MLS
Some properties are special simply because of the story behind them. This 150 acre farm with 3,168 feet of road frontage in Winchester has been cared for by the same family since 1803, and it's now being offered for sale for the very first time. The land is classic Kentucky countryside, rolling pastures, peaceful water, and wide open views in every direction. Four ponds and a gently flowing creek bring both beauty and function to the farm, while four barns and two storage sheds make it ready for cattle, horses, or anyone wanting a true working farm. There are two homes on the property, offering flexibility for extended family, guests, or farm operations. Whether you dream of continuing its farming legacy, creating a private retreat, or investing in a truly special piece of Kentucky land, this is the kind of place that rarely becomes available. Opportunities like this don't come around often. This farm has been part of one family's story for over two centuries, now it's ready for its next chapter.

3049 Ironworks Rd, Winchester

$349,900
4 Beds 3 Baths 26014834 MLS
Updated Price, below Apprisal value...Space, Location, and Great Finishes....4 bedrooms, 2.5 bathrooms, walk in sit down and relax...Dining Room/Living Room or Office welcomes you as you enter from the covered front porch. Guests can use the 1/2 bathroom on the main level...Open Kitchen and Family Room with granite counter tops, breakfast bar, and large pantry making cooking easy, 10 ft ceilings on the mail level offer a more open feel. Upstairs you will find a large laundry room 3 bedrooms a guest bathroom with double vanity! The primary bedroom offers plenty of room, double vanity bathroom, and custom walk-in closet. Outside the yard is fenced with vinyl style fencing, a patio for grilling and 2 car attached garage for your vehicles and storage. This home has all the space and it's priced to sell!

119 Gibson Way, Winchester

$795,000
3 Beds 3 Baths 26012252 MLS
**Click on the Virtual Tour section to see the video walk through!** Nestled in the peaceful countryside of Winchester, this charming property on Van Meter Road offers the perfect blend of privacy, comfort, access and room to roam. Set on 13.74 beautiful, fenced acres and located within minutes of I-64, I-75 and the Mountain Parkway, this unique property offers easy access to Lexington, Winchester, Paris, and all of Central Kentucky. Enjoy wide-open spaces, scenic surroundings, and the tranquility of rural living minutes from city amenities. Designed for ease and functionality, the home features convenient one-level living with the added bonus of a finished basement--perfect for extra living space, entertaining, or hobbies. An inviting all-season room provides the ideal spot to relax year-round and a covered front porch overlooking a neighboring pond offers a tranquil place to enjoy your morning coffee or wind down at the end of the day. The kitchen features brand new stainless appliances, with transferrable warranties to the new owner. Did I mention the new roofs and Geothermal HVAC for efficient inside temperature control? Don't miss the first level primary bedroom with a private bathroom and walk in closet. Outside, the property really shines with a detached 3-car garage and a large barn with three stalls, a tack room and two multipurpose rooms. Also there is an additional metal barn with a tool room and three multipurpose rooms. All of these outbuildings have electricity and the wooden barn also has water with a separate fenced area for animals. Whether you're looking for a quiet retreat, a working or hobby farm, or a place to create lasting memories, this property delivers a warm and welcoming atmosphere you'll love coming home to.

6356 Van Meter Rd, Winchester

$375,000
3 Beds 3 Baths 26013780 MLS
Just a 20-second golf cart ride to the Winchester Country Club driving range! Built in 2024 and upgraded throughout, this beautiful 3-bedroom, 2.5-bath home offers modern style, functional living space, and a prime location. The open-concept main level features a spacious living room, kitchen, and dining area designed for both everyday living and entertaining, complete with granite countertops in the kitchen and baths, a deep farmhouse sink, pantry, and stainless appliances. Upstairs, you'll find a generous primary suite with a private bath and walk-in closet, along with two additional bedrooms and a full guest bath. Luxury vinyl plank flooring runs throughout the home, while accent wallpaper in multiple rooms adds warmth, personality, and a custom feel. Recent owner upgrades include a privacy fence, landscape lighting and new shrubs, upgraded stair treads, a concrete sidewalk, and additional attic flooring with a folding attic ladder for convenient storage. The home's attractive exterior combines clean modern lines with shake-style architectural accents, creating great curb appeal. Enjoy nearby golf course views and the convenience of country club living without being directly on the course. Additional features include a 2-car attached garage, crawlspace foundation, and no HOA. With modern construction, quality finishes, and numerous owner-added improvements, this move-in ready home is ready for its next owners to enjoy.

309 Gallahadion Ct, Winchester

$459,000
4 Beds 3 Baths 26013041 MLS
Welcome to 105 Monet Blvd., located in one of Winchester's most desirable neighborhoods! This beautifully updated home offers the perfect combination of space, style, and future potential. Featuring 4 spacious bedrooms, a dedicated home office, formal dining room, family room, and an eat-in kitchen, this home was designed for both comfortable living and entertaining. The newly remodeled kitchen is the centerpiece of the home and is complemented by brand-new KitchenAid appliances, including a refrigerator, microwave, and dishwasher. Additional updates include fresh paint throughout the entire home and brand-new carpet throughout the upstairs, making this property truly move-in ready. Looking for room to expand? The walk-out basement is already studded and ready to be finished, offering endless possibilities for additional living space, a home theater, gym, recreation room, or guest suite. Situated in one of Winchester's most sought-after subdivisions, this home offers the space you need today with the opportunity to grow tomorrow. Don't miss your chance to make 105 Monet Blvd. your next home!

105 Monet Blvd, Winchester

$445,500
3 Beds 3 Baths 26009944 MLS
This is a perfect home for EVERY season.....enjoy multiple, interior gathering spaces and the glow and warmth of either the L R or Dining Room fireplace on the main level or the coziness of the mesmerizing fireplace in the lower level family room during the winter. Watch the backyard come alive with rich and lush vegetation during the Spring from the large, glass walled sun room. For Summer, tons of options await you with the covered front porch, the partially covered back deck or escape to the seclusion of the covered, separate structure at the back. Both the front and back yards are landscaped with many mature trees and perennials that require little attention during Spring, Summer and Fall. Inside, this expansive floor plan packs a lot of punch with a number of interior spaces with an easy flow. The wide entry hall foretells of large room sizes and fresh, neutral paint throughout. The newly renovated kitchen with light wood cabinets is timeless in it's appeal and the adjacent breakfast area is full of natural light. Another handsome fireplace in the next space, with built in shelves could easily function as a D R or Den and the sunroom gives a panoramic view of the beautiful back yard. Three bedrooms and two baths round out the first floor. The lower level features a massive two car garage, half bath, laundry and a large Family Room/Man Cave space for quiet reading or lively entertaining with a third fireplace. So many beautiful options await you in this wonderful home, located in a quiet, attractive, safe and neighborly enclave.

42 Mockingbird Valley Rd, Winchester

$375,000
4 Beds 3 Baths 26008931 MLS
Built in 1893, this beautifully maintained home is filled with the charm and craftsmanship that's hard to find today, along with the modern updates buyers appreciate. Situated on a corner lot just minutes from historic downtown Winchester, you'll love the walkable location with South Main Grocery & Grill, a local favorite known for its country ham sandwiches and home-cooked meals, right across the street. The Clark County Public Library, College Park, and downtown Winchester's shops, restaurants, and local events are all just a short walk away. Inside, you'll find over 3,300 square feet featuring four bedrooms, three full baths, soaring ceilings, gorgeous hardwood floors, four fireplaces, beautiful original woodwork, and an updated kitchen that complements the home's historic character. Multiple living spaces provide plenty of room for entertaining, working from home, hosting guests, or simply spreading out, plus the convenience of a basement-entry garage. Enjoy your morning coffee or unwind in the evening from the inviting front porch, the perfect spot for a porch swing and visiting with neighbors. Out back, you'll appreciate the screened-in porch overlooking the secluded-feeling backyard, an ideal space for relaxing, grilling, or enjoying a quiet evening outdoors. Homes like this don't come along often. Rich in history, full of character, and ideally located near the heart of downtown, this home offers the perfect mixture of classic architecture, modern updates, and everyday convenience. Enjoy the charm of small-town living while still being an easy commute to Lexington for work, shopping, dining, and entertainment. If you've been dreaming of owning a home with historic charm, modern comforts, and a location that truly lets you enjoy the best of Winchester, this is one you won't want to miss.

382 S Main St, Winchester

$345,000
3 Beds 3 Baths 26013361 MLS
A beautiful designed spacious house that offers 3 bedrooms, 3 full bathrooms, and 2266 sq ft og thoughtfully designed living space. Step inside to discover an open-concept layout perfect for both everyday living and entertaining. The well-appointed kitchen flows seamlessly into the main living areas, creating a warm and inviting atmosphere. Generously sized bedrooms provide comfort and privacy, while the flexible floor plan offers space to fit your lifestyle. Located in a growing Winchester community, you'll enjoy the small-town living with convenient access to shopping, dining, schools, and major roadways. Don't miss your opportunity to own this beautiful home. The home features custom made window blinds as a plus. There is a preschool and two elementary schools within walking distance! Quiet neighborhood.

107 Gibson Way, Winchester