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$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
$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
$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
$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
$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
$329,900
4 Beds ⋅ 2 Baths ⋅ 26006679 MLS
Back on the market at no fault of the sellers. Don't miss your chance to own this beautifully updated split-level home in Holiday Hills! Featuring 4 bedrooms and 2 full baths, this home offers a bright, open-concept kitchen and living area perfect for both everyday living and entertaining. Thoughtfully updated in recent years, the home features newer flooring, fresh paint, updated cabinets and countertops, modern electrical and plumbing fixtures, a newer driveway, and more giving you a move-in ready feel from day one. Enjoy outdoor living with a spacious backyard, newer deck and beautiful landscaping. This home offers the perfect blend of space, style, and convenience. Schedule your private showing today!

228 Holiday Rd, Winchester
$499,000
5 Beds ⋅ 3 Baths ⋅ 26013305 MLS
First time on the market! This one-owner, all brick home offers 5 bedrooms, 2.5 baths, and sits on a spacious 0.6-acre lot. The well-designed floor plan provides plenty of room for family living and entertaining. The finished basement features a dedicated office and recreation room, offering flexible space for work, hobbies, or play. Enjoy the quality and durability of brick construction, a large yard, and the pride of ownership that shines throughout this well-maintained property. Don't miss this rare opportunity to make this exceptional home your own!

182 Chardonnay Ct, Winchester
$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
$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
$499,900
4 Beds ⋅ 3 Baths ⋅ 26010312 MLS
One Time Homeowner! Beautiful fieldstone ranch on full finished basement. 4 Bedrooms, 3 full bathrooms. This home has a very large great room, perfect for entertaining! Home has a new roof and siding as of 2024, new windows as of 2025. Home has tons of storage and tons of character. Come see this wonderful house and make it your forever home!

16 Manor Dr, Winchester
$268,900
4 Beds ⋅ 3 Baths ⋅ 26011798 MLS
Spacious and well - maintained 4 bedroom home featuring 2 full bathrooms, one half bath which is ready to be upgraded with the addition of a shower to function as an additional full bathroom. This home offers a comfortable layout with replacement windows, a cozy wood burning fireplace and updated stainless steel appliances incuding the range, refrigerator, dishwasher and microwave. Enjoy outdoor living on the rear covered deck overlooking the well - tended backyard. A drain system efficiently carries water to the end of the property for added peace of mind. With thoughtful updates and solid upkeep throughout, this property is move-in ready and is full of charm

311 Geronimo Ct, Winchester
$515,000
5 Beds ⋅ 3 Baths ⋅ 26007022 MLS
Brick ranch with 3 upstairs bedrooms and 2 bedrooms in your mother in law suite and full finished basement, complete with kitchen. 2 gazebos with one attached to walk out porch over looking almost 3 acres of beautiful land. Attached 2 car garage and detached 2 car garage. Barn/workshop included, along with another metal building for storage.

110 White Conkwright Rd, Winchester
$775,000
5 Beds ⋅ 3 Baths ⋅ 26007545 MLS
Dreaming of wide-open spaces and country charm? This beautiful 16-acre property in Clark County offers the perfect blend of comfort and functionality. The stately brick home provides generous living space with classic appeal, offering endless potential. With five bedrooms and three full baths, the home accommodates a variety of living arrangements, whether you need space for guests, a home office, or simply room to spread out. The generously sized living area opens seamlessly into the dining area, creating a natural gathering space for those family gatherings or functional for everyday living. With a 42 x 40 metal barn, open pastures and scenic surroundings, this property is ideal for equestrian enthusiasts, hobby farmers, or anyone looking to escape the hustle without sacrificing convenience. Enjoy peaceful mornings, breathtaking sunsets, and room to roam—all within easy reach of Lexington. The home is ready for its next owner to move in and make it their own, Seller is offering a generous flooring allowance with an acceptable offer providing the opportunity to refinish the existing hardwood floors and replace carpeting. Buyer to verify all aspects of the property and school districts.

465 Morris Rd, Winchester
$2,750,000
8 Beds ⋅ 8 Baths ⋅ 26009631 MLS
Welcome to 4664 Lexington Road—a magnificent private estate on 35 rolling acres of pristine Kentucky countryside that feels worlds away, yet sits just minutes from the charm of Winchester and the vibrancy of Lexington. A stately stone entry welcomes you down a graceful, winding driveway to a sweeping circular drive, leading to a grand 13,000+ square-foot residence built in 1997 with timeless elegance and generous proportions. Inside, the 8-bedroom, 7.5-bath home offers expansive living spaces bathed in natural light, refined finishes, and classic architectural details—perfect for both intimate family moments and large-scale entertaining. A fully finished basement adds exceptional flexibility for recreation, additional living quarters, or extended gatherings. Outdoors, the property continues to impress with sweeping valley views, open pastures and mature wooded areas. Enjoy the private pool as a true retreat. Additionally, the property is complemented by a classic tobacco barn and additional shop space ideal for storage, hobbies, equestrian use, or agricultural pursuits. Zoned PD (Planned Development), this estate presents rare versatility and significant upside—whether envisioned as a forever family home, a multi-generational retreat, a private equestrian estate, or a thoughtfully planned development opportunity. Privacy is unparalleled, yet convenience is effortless, with easy access to world-class horse farms, bourbon trails, and the cultural amenities of the Bluegrass Region. This is more than a home—it's a legacy property where luxury living, natural beauty, and gracious Kentucky living come together in perfect harmony, delivering exceptional value and endless possibilities.

4664 Lexington Rd, Winchester
$724,950
2 Beds ⋅ 3 Baths ⋅ 25507944 MLS
Hunter's Paradise! This beautiful 85 acre farm is nestled in the heart of Clark County. Wildlife is abundant as you travel throughout the property. The home is very spacious with a full mother in law suite. Entertain friends at the full bar, while enjoying the wood burning stove. A functioning greenhouse expands the possibilities for year round gardening. If you are looking for little piece of Heaven in the country this is your place. Only minutes from the Mountain Parkway, downtown Winchester, and Mount Sterling. Restaurants, shopping, golf courses, and several amenities are also just a short drive away.

455 Davis Ln, 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
$649,900
3 Beds ⋅ 4 Baths ⋅ 26007244 MLS
Beautifully remodeled farmhouse on 10 fenced acres! This 3 bedroom, 3.5 bath home with a fully finished basement offers the perfect blend of modern upgrades and country living. Inside, you'll find refinished hardwood floors and fresh paint throughout. The custom kitchen is designed to impress with new cabinetry, granite countertops, glass subway tile backsplash, double ovens, two dishwashers, and a built-in walk-in pantry. Bathrooms have been completely updated with new tub surround, tiled showers, and custom vanities. Step outside to enjoy wide open, fenced acreage and a barn, making this property ideal for farming, animals, or simply enjoying peaceful rural living. Conveniently located close to I-64, downtown, restaurants, shopping and more. Schedule your showing today.

1480 Irvine Rd, Winchester
$284,900
4 Beds ⋅ 2 Baths ⋅ 26009371 MLS
Conveniently located, this charming well kept home features a functional floor plan offering space that can be tailored for those who love to entertain or the growing family. On the main level you'll find the living room, an eat in kitchen, 3 bedrooms and a full bathroom. Off of the kitchen is a large deck that's perfect for get togethers with family or friends. Downstairs has a second living area/flex space as well as an additional bedroom and bathroom. The fenced in backyard features plenty of shade and a 12'x24' storage shed. Don't miss out on this great move in ready home! Seller is offering $3,000 BUYER CREDIT!

618 Westmeade Dr, Winchester
$289,999
3 Beds ⋅ 3 Baths ⋅ 26008330 MLS
PRICE DROP and a MOTIVATED SELLER!! Currently priced below 2026 Clark County Department of Revenue Property Assessment valuation. Turn-key, dialed-in, and ready to impress! This Craftsman-style stunner delivers the space, flow, and finishes today's buyers are chasing. With 3 oversized bedrooms, 2.5 baths, and a fully finished walk-out basement, this home lives large and shows even better. The main level hits immediately with an open, airy layout that connects living, dining, and kitchen into one seamless entertaining hub anchored by sleek stainless steel appliances and clean, modern finishes. Upstairs, the primary suite feels like a true retreat with a full bath and walk-in closet, while two additional bedrooms, a second full bath, and a dedicated laundry room keep everyday living effortless. From top to bottom, you'll love the cohesive design; neutral tones, plush carpet, and durable hardwood-look LVP that's as stylish as it is practical. And then there's the backyard! Fully fenced, private, and backing to scenic farmland for wide-open views you rarely find. Quiet, peaceful, and a perfect place to unwind or entertain. Homes with this combination of layout, finish, and setting don't sit. Schedule your showing and bring your buyers before it's gone. Seller is related to Listing Agent.

414 Pueblo Ct, Winchester
$749,900
4 Beds ⋅ 4 Baths ⋅ 26015372 MLS
Escape to your own private retreat on 10+ breathtaking acres featuring a stunning 4-bedroom, 4-bath ranch home with over 4,000 square feet of living space and a full basement with unforgettable panoramic views. The bright, open kitchen offers granite countertops, abundant natural light, and a view you'll never tire of, along with an eat-in area and formal dining room. The spacious primary suite features a spa-like bathroom, and a dedicated home office provides the perfect space to work from home. Designed for the convenience of one-level living, the basement offers a full bath, generous storage, and endless possibilities for additional living or entertaining space. Outside is where this property truly shines—complete with a 6-stall barn, five fenced paddocks, and water lines to both the barn and each paddock, making it ideal for horses. This property has it all. Less than 3 miles to downtown Winchester and Lykins Park . This property is ready for entertaining, family gatherings, or simply enjoying the beauty and privacy this property offers.

2509 Mount Sterling Rd, Winchester
$539,500
4 Beds ⋅ 5 Baths ⋅ 26013378 MLS
Step into the timeless elegance of this stunning Southern antebellum-style home, where classic charm meets modern luxury. Boasting four spacious bedrooms and five beautifully appointed bathrooms, this grand residence offers an unparalleled level of sophistication and comfort. A breathtaking foyer and entryway welcome you with a sweeping staircase, and exquisite architectural details, setting the tone for the elegance that flows throughout the home. The formal living room exudes Southern charm, featuring intricate moldings, and large windows that bathe the space in natural light. The formal dining room is perfect for hosting memorable gatherings, with ample space for entertaining in style. Designed for both beauty and function, this home seamlessly blends historic inspiration with modern amenities, creating a warm and inviting atmosphere. Whether you're enjoying a quiet evening on the spacious screened in porch or hosting lavish celebrations, this extraordinary estate is a true embodiment of Southern grace and hospitality.

600 Boone Ave, Winchester
$599,000
4 Beds ⋅ 4 Baths ⋅ 26014796 MLS
The perfect amount of land and a fully renovated home rarely arrive together. This 12.64-acre property between Mt. Sterling and Winchester delivers both, minutes from Lexington. Built in 2006 and taken down to the studs in an extensive 2024 renovation, this wonderful farmhouse now reads as new construction with the presence of something more established. Hardiplank siding and a metal roof give it a durable, low-maintenance exterior, and a wraparound deck of more than 1,100 square feet extends the living space overlooking the rolling countryside. The land features a stocked pond for fishing, an old tobacco barn for workshop or hobby-farm use, and a row of thornless blackberries alongside two producing pear trees. The main level centers on a new designer kitchen finished in Taj Mahal quartzite, custom cabinetry outfitted with Frigidaire Professional appliances, double ovens, and two dishwashers. A gas cooktop is in place, with electric already run for a seamless swap should the next owner prefer it. Beneath a vaulted ceiling, the living spaces flow off the kitchen with abundant light and scratch-resistant LVP flooring chosen to stand up to country living without sacrificing finish. On the main level is a primary suite with walk-in closet and full bathroom, a secondary bedroom and another full and a half bathroom. One of two laundry rooms is just off the rear mudroom. The walkout lower level adds two more bedrooms, a full bath, a second kitchen, and its own laundry, all with private access if desired. It flexes easily to an in-law suite or extended-stay guest quarters. Systems match the renovation's recency: all-new 2024 HVAC, dual-source heat, and spray foam insulation throughout for year-round efficiency. Gas has been run for a permanent outdoor grill, extending the kitchen onto the wraparound deck. All this results in an exceptional Bluegrass homestead, renovated and built to last for generations.

8586 Wades Mill Road Mt, Mt Sterling
$312,000
3 Beds ⋅ 3 Baths ⋅ 26008794 MLS
Welcome to this beautifully maintained 5-year-old home nestled on a quiet cul-de-sac in the desirable Ft. Estill area of Winchester. This charming property offers 3 bedrooms and 2.5 baths, a spacious and functional layout with comfortable living areas perfect for both everyday living and entertaining. Enjoy low-maintenance flooring throughout all the main living areas and plenty of natural light The kitchen offers ample cabinet and counter space, a full array of SS appliances and a functional layout that flows seamlessly into the main living area and breakfast area. Just off the breakfast area is a generously sized deck overlooking the peaceful creek and farmland of adjacent property. The second-floor primary suite includes LPV flooring, a private en-suite bath with double bowl vanity and a generously sized walk-in closet, while two additional bedrooms provide flexibility for guests, a home office or hobbies. The dedicated second floor laundry area is conveniently located to all bedrooms. The finished, walk-out basement offers LPV flooring and can be used for additional living space, theater room, playroom...the possibilities are endless. The home also includes a 1-car attached garage, and energy-efficient systems (solar panels) for added convenience and large reduction on energy bills. Located just minutes from the bypass, commuting to Lexington is easy, while nearby shopping, dining and schools add to the home's appeal. Don't miss this opportunity to own a comfortable, well-located home at an excellent value. Whether you're a first-time buyer, downsizing or looking for a solid investment opportunity, this property delivers comfort, convenience and value in a growing area.

412 Pueblo Ct, Winchester
$264,900
5 Beds ⋅ 2 Baths ⋅ 26004166 MLS
**Don't miss this exciting opportunity to pick out the new flooring for the basement and kitchen with a full price offer.****New roof (8 months old), one year old AC and heating unit, new large storage shed, and one year old wooden fence All of the expensive upgrades have been done. Come make this home your own. All-brick ranch with a full walk-out basement! This charming home offers excellent potential for the right buyer. The main level features three bedrooms, a full bath, a comfortable living room, and an eat-in kitchen. The walk-out basement expands the living space with two additional bedrooms, full bath, family room with a kitchenette area, utility room, and ample storage with built-in shelving. Step outside to a spacious backyard, fully enclosed with a wooden fence, perfect for pets, play, or outdoor enjoyment.

55 Hillcrest Dr, Winchester