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1480 Irvine 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

418 David Ln, Winchester
$629,000
6 Beds ⋅ 5 Baths ⋅ 25014801 MLS
This impeccable house is a Buyer's Delight. Located in the most desirable residential neighborhood, Stoney Brook. Discover a serene retreat in this beautifully appointed home, offering spacious interiors and breathtaking outdoor spaces. Step into the front door and discover the soaring ceilings with beautifully appointed crown molding. The flowing space from the dining room to the great room to the custom kitchen featuring a double oven and cooktop, microwave, and dishwasher. The utility room is convenient to the kitchen and the garage. The private first floor primary bedroom features a completely renovated bathroom and massive closet/storage space. On the second level you will find second primary suite, 2 more bedrooms and a separate bath. The lower level of the house features a recreation room, 2 bedrooms, a full bath and an office and a storage area for you outdoor equipment. The patio and deck, overlooking a beautifully manicured lot provide lots of space for entertaining family and friends. So much more to see so make an appointment today to see this house that may be your next home.

418 David Ln, Winchester

5865 Van Meter Rd, Winchester
$615,000
3 Beds ⋅ 3 Baths ⋅ 26010445 MLS
Experience the perfect balance of peaceful country living and modern comfort at 5865 Van Meter Road. Situated on 5.05 scenic acres with breathtaking farmland views, this spacious ranch-style home offers more than 2,700 square feet of thoughtfully designed living space with privacy, versatility, and charm throughout. A brand-new roof installed in May 2026 adds even more value and peace of mind. Inside, you'll find beautiful hardwood and tile flooring, a warm and inviting living room with fireplace, and an updated kitchen featuring abundant cabinetry, breakfast bar seating, and a cozy eat-in dining area. The spacious primary suite serves as a relaxing retreat with heated bathroom floors, towel warmer, and custom closet organization. The partially finished walk-out and walk-up basement provides flexible additional living space perfect for a recreation room, home office, guest quarters, or entertaining area. A wood-burning fireplace adds character and comfort, while the gas furnace with built-in humidifier enhances year-round efficiency and convenience. Outdoor amenities make this property truly stand out. Enjoy the large double rear deck overlooking rolling farmland, a massive 44x30 workshop/outbuilding, partial fencing, and a 50-amp RV hookup. Whether you need room for hobbies, equipment, animals, or simply want space to enjoy the outdoors, this property offers endless possibilities. The newly constructed pond is approximately 90% owned by the property owner and 10% shared with the neighboring property. Conveniently located with quick access to I-64 and I-75, this exceptional property delivers the serenity of rural Kentucky living while remaining only 15 minutes from Hamburg and approximately 25 minutes from UK Hospital. Acreage, updates, functionality, and stunning views come together in this rare opportunity.

5865 Van Meter Rd, Winchester

6595 Mt Sterling Rd, Winchester
$609,000
5 Beds ⋅ 4 Baths ⋅ 26011548 MLS
Welcome to 6595 Mount Sterling Rd. offering the perfect blend of space, convenience, and flexibility on 2.59 acres. Ideally located just off I 64 between Winchester and Mount Sterling, this property provides easy interstate access while still offering privacy and room to spread out. This custom home features 5 bedrooms, 3 full baths, and a versatile floor plan. The main level includes a vaulted family room, open eat in kitchen, primary suite, and two additional bedrooms. Upstairs you'll find a second private primary suite complete with an oversized walk in closet and ensuite bath. The finished walkout basement adds even more functional living space with a 5th bedroom, two bonus rooms, full bath, laundry area, storage, and an additional one car garage. Outdoor features include a vaulted covered deck overlooking the property and a brand new oversized detached garage ideal for RV storage, boats, workshop space, hobbies, or additional vehicles. Back on market through no fault of the sellers. Property has already completed inspections and has a recent appraisal available. Move in ready with quick access to I 64 and convenient to both Winchester and Mount Sterling.

6595 Mt Sterling Rd, Winchester

433 Fairholme Way, Winchester
$600,000
3 Beds ⋅ 4 Baths ⋅ 25015409 MLS
This elegant ranch on a basement offers refined main-level living with upscale finishes throughout. The chef's kitchen is a standout featuring double ovens, custom soft-close cabintry, granite countertops, a large island with seating, a spacious walk-in pantry for entertaining and everyday ease. Primary bedroom has Amish cutom built closet. Enjoy quiet evenings on the covered front porch with brick and stone accents, and a low maintenance PVC back deck overlooking serene views. The spacious unfinished basement offers endless potential and already includes a full bath, home gym (which could serve as 4th bedroom) and utility garage. Tucked just behind the Winchester Country Club golf course, this home blends comfort, craftsmanship, and future flexibility in a truly prime location.

433 Fairholme Way, Winchester

905 Pretty Run Rd, Winchester
$600,000
3 Beds ⋅ 4 Baths ⋅ 26008251 MLS
Welcome to this elevated farmhouse classic-refined yet unpretentious, elegant yet entirely inviting. The kind of home that feels just as suited for quiet family life as it does for hosting gatherings that spill effortlessly from indoors to out with the wrap around porch, deck, outdoor kitchen & grill, POOL and hot tub spa, firepit & so much more...Welcome to 905 Pretty Run Road! Greeted by a two-story foyer & rich hardwood floors throughout the first floor you will want to see more. Make your way to the heart of the home- the beautiful kitchen and hearth room with a wood burning fireplace. 3 Bedrooms & 3.5 baths along with a full finished basement w/LVP flooring that has space to relax, game, or work! Option for a 4th bedroom in the basement as it has a connected full bath and access to the back making it a great flexible space. Outside the landscaping consists of low manicured shrubs and soft flowering plants that add texture & color. The green lawn stretches over 2 acres reinforcing the homes sense of space and privacy while offering picture-perfect views of the nearby horse farm. Come see why this home will check all of your boxes! Easy access to the Interstate and just a 30-minute drive to downtown Lexington

905 Pretty Run Rd, Winchester

104 Bella Shae Way, Winchester
$595,090
3 Beds ⋅ 3 Baths ⋅ 26000264 MLS
Welcome Home to the Winchester Floor Plan by CP Builders. This elegant ranch home features all-brick construction, a welcoming front porch, and a two-car garage. Step inside and be greeted by soaring 9-foot ceilings and a spacious open floor plan. The split bedroom design offers privacy and comfort, with a luxurious primary suite boasting an ensuite bathroom and a walk-in closet. Enjoy easy maintenance with luxury vinyl plank flooring throughout the home. The heart of the home is the spacious great room, complete with a cozy gas log fireplace, perfect for gathering with loved ones. The well-appointed kitchen features a large island, ideal for both cooking and entertaining. Additional features on the first floor include a full bathroom, a convenient half bath, and a separate laundry room for added convenience. Step outside onto the back patio and enjoy the fresh air and sunshine. Let's build your dream home and make the Winchester Floor Plan yours!

104 Bella Shae Way, Winchester

180 Casa Landa Way, Winchester
$584,900
4 Beds ⋅ 4 Baths ⋅ 25017032 MLS
This stately yet inviting residence in the highly desirable Stoney Brook subdivision offers the perfect blend of elegance and comfort. Thoughtfully designed for everyday living and entertaining, the home features generously sized rooms throughout. The main level includes formal living and dining spaces, a convenient half bath, and a beautifully appointed kitchen with granite countertops, stainless steel appliances, an island, two pantries, and a casual dining area that flows into the family room featuring a masonry gas-log fireplace. Upstairs, the expansive primary suite includes a sitting area, a spa-like bath, and an oversized walk-in closet. Two additional bedrooms, a full guest bath, and a laundry room complete the second floor. The finished basement provides exceptional flexibility with a large recreation room, full bath, guest bedroom, and direct access to the backyard. Outdoor living is equally impressive: enjoy the partially covered deck, 16x36 in-ground pool with maintenance-free vinyl privacy fence, lush flower gardens, open lawn space with a swing set, & a cozy fire pit area. This home offers location, lifestyle and luxury in one perfect package!

180 Casa Landa Way, Winchester

101 S Burns Ave Unit 1,2,3,4, Winchester
$580,000
8 Beds ⋅ 4 Baths ⋅ 25505825 MLS
Step into a rare investment opportunity in the heart of downtown Winchester! This beautifully renovated 4-plex offers charm, space, and convenience — all within a fully restored historic building. Each of the four spacious units boasts approximately 1,296 sq ft, blending timeless character with modern updates. The entire property has been thoughtfully renovated in 2021, including a brand-new roof, updated interiors, and a clean, professional aesthetic ideal for long-term tenants with all the appliances included. Additional features include: Prime downtown location — walkable to shops, dining, and local attractions, 4 parking spots ( 1 for each unit), as well as, off street parking available. Strong rental potential in a growing market Zoned and ready for investment use

101 S Burns Ave Unit 1,2,3,4, Winchester

7919 Mt Sterling Rd, Winchester
$550,000
4 Beds ⋅ 4 Baths ⋅ 26012124 MLS
Don't miss the opportunity to own this stunning 3,431 sq. ft. custom-built brick home featuring 4 bedrooms, 3 full baths, and situated on 3 beautiful acres overlooking Stoner Creek. Nestled in a serene, park-like setting, this remarkable property combines the peace of country living with the convenience of nearby amenities. From the moment you step into the dramatic two-story entryway, you'll be welcomed by custom cabinetry, detailed craftsmanship, and timeless finishes throughout. One of the home's most breathtaking features is the sunroom, offering tranquil views of the wooded landscape and flowing creek beyond. The finished basement includes a private in-law suite, providing added flexibility and comfort for guests or extended family. In addition, the property features an impressive custom builder's workshop with over 1,250 sq. ft. of space — ideal for hobbies, storage, or projects. Fresh updates and a fresh new price make this home even more appealing! Brand new paint and carpet throughout create a move-in ready feel, while the recent price improvement offers exceptional value. A rare opportunity to enjoy space, privacy, craftsmanship, and elegance all in one extraordinary property.

7919 Mt Sterling Rd, Winchester

556 Earlymeade Dr, Winchester
$550,000
4 Beds ⋅ 5 Baths ⋅ 26006630 MLS
As you walk in the front door of this house you will immediately be thrilled because the owners have loved this house and this is evident from the gleaming hardwood floors to the fresh coats of paint. This house is located in the most desirable neighborhood of Earlymeade. It is near lots of popular destinations, including Hamburg in Lexington and the I-64 and I-75 corridors so you can be in Richmond in minutes also. This 11 year old home is just like new because the owners have beautifully maintained with lots of updates, including paint and replacing primary bathroom tile and most recently finished 1700 feet of the basement. The basement has a bedroom and a full bath and also a wet bar. The basement is a walkout and has a full one car garage/lots of storage space. The main level features the primary bedroom and 2 bedrooms with their own private bathrooms. The kitchen is well equipped with appliances and has lots of cabinets. The utility room is also well equipped with cabinets. From the kitchen walk out to a serene setting on a covered porch with a view of Kentucky Bluegrass. The inviting front porch also is very cozy with ample space for a porch swing. This house provides lots of space for entertaining family and friends. Make your appointment to see this house today, it may be your new home!

556 Earlymeade Dr, Winchester

445 Lynnway Dr, Winchester
$545,000
4 Beds ⋅ 4 Baths ⋅ 25502127 MLS
For only the second time ever, this remarkable Colonial home is being offered for sale in the coveted Stoney Brook subdivision. From the moment you step into the welcoming entry hall, gleaming hardwood floors and timeless details set the stage for a home filled with warmth, tradition, and charm. The main level is designed for both everyday comfort and memorable gatherings. A gracious primary suite with a large walk-in closet provides the perfect retreat, while the formal living room—complete with a grand piano—and elegant dining room invite you to host in style. The heart of the home is the family room, where a cozy gas log fireplace frames sweeping views of the covered porch and picturesque backyard. In the kitchen, rich cherry cabinetry and an inviting eat-in space promise countless shared meals and memories. Upstairs, three spacious bedrooms offer comfort for family and guests—one with its own private bath, and the other two sharing a full bath. Access the unfinished attic space with 895 SF of endless potential to create another bedroom, bonus room and more. This space is also accessible from a back stairway that leads to the hallway from the garage entrance. The finished basement extends the home's living potential with two recreation areas anchored by a classic wood-burning fireplace. An unfinished storage room with roughed-in plumbing awaits your vision for an additional bathroom, making this space as practical as it is full of opportunity. With 4 bedrooms, 3.5 baths, and a two-car garage with extra storage, this home is more than just a place to live—it's a chance to own a unique home to create a lifetime of cherished moments.

445 Lynnway Dr, Winchester

108 Bella Shae Way, Winchester
$539,000
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

2100 Stoner-Ephesus Rd, Winchester
$535,000
2 Beds ⋅ 2 Baths ⋅ 26003590 MLS
Beautiful 44.21 acre farm has so much to offer. The main residence features 2 spacious bedrooms and 2 full bathrooms, offering inviting living spaces and peaceful views of the surrounding countryside. The separate guest quarters has 1 bedroom and 1 bathroom and is ideal accommodations for visitors, extended family or staff. You will appreciate the thoughtfully designed facilities, including two barns and lower one with electric and water , dedicated tack room, seven stalls and ample room for hay storage in part of lower barn and a larger amount in upper barn. The property also includes a dedicated office with electric, an outdoor riding arena, four paddocks with water, five lush fields with four of them having water, and plank fencing. An outdoor riding arena offers the perfect space for training, lessons, or daily exercise. The farm is great for horses and the potential for boarding income, this turnkey property combines rural charm with exceptional functionality. Whether you're an avid rider, trainer, or simply seeking a peaceful county lifestyle, this remarkable farm is ready to welcome you home.

2100 Stoner-Ephesus Rd, Winchester

146 Hawthorne Dr, Winchester
$529,000
5 Beds ⋅ 4 Baths ⋅ 26010893 MLS
Remarkable Custom Built Home! Stunning 5 bedroom, 3.5 bath with lots of storage built in 2021. This home is sure to please as it is in excellent condition with well appointed features in a convenient setting. The custom work throughout this home is amazing! Upon entering a large foyer you will embrace an open setting that flows into a cozy family room and spacious kitchen. The family room is flanked by ship lap accent walls, floating shelves and fireplace. The kitchen boasts custom white cabinets, granite countertops, stainless appliances (wifi ovens), large island, and a formal dining room. The huge primary suite is also on the main level with a primary bath that you will love (his and her separate vanities, walk-in shower and tub, wifi speakers and a large walk-in closet). Additionally on the main level, are 3 bedrooms, another full and a half bath, and a large utility room with a sink. The upper level opens to an additional primary bedroom (or could be a recreation area) with a full bath and a newly added mini split heating and cooling unit. This home has lots of curb appeal with nice landscaping, large front porch, and well coordinated colors. A covered back deck and patio area, side garage door to unfinished storage/crawl space (partial concrete floor), and a newly installed fence complete this unique setting. Current owners have also extended the back patio with new landscaping. In addition to these improvements, an extra parking space was added, the entire home was painted. All of this within just a couple of minutes to shopping and dining. This is a MUST SEE!

146 Hawthorne Dr, Winchester

1953 Cabin Creek Rd, Winchester
$525,000
6 Beds ⋅ 5 Baths ⋅ 25500498 MLS
***Click on the Virtual Tour section to see the video walk through!*** This unique property includes not only one, but two beautiful homes in the heart of Kentucky Bluegrass country. The first home is a brick ranch with a covered front porch and back patio that overlook this beautiful piece of farm land. This 2046 sq ft home contains 3 bedrooms and 2 full baths with a large great room in the middle featuring a central stone fireplace and an updated kitchen with gleaming granite countertops. The second home is a 1400 single story on top of a full basement that includes ample garage space for a workshop including its own bathroom. On the main floor are 3 bedrooms and a full bath, but the crowning glory of this home is the oversized, covered back patio that provides a lovely view of the countryside and ample space for outdoor living. This would make an excellent property for two families that need to be close, but not in the same house. Schedule your private showing today and see if this beauty might work for your needs.

1953 Cabin Creek Rd, Winchester

665 Lillies Ferry Rd, Winchester
$525,000
26014623 MLS
You do not want to sleep on this one, it is a beautiful working farm with multiple building sites and amazing views and tranquility. Two farms are selling together for a total of 91.28 acres that is already a very productive cattle farm. The fencing, gates, waterers and infrastructure is already in place to move right in and produce income. There are multiple possible building sites with amazing views. An existing hunting cabin is also onsite for recreation or possible renovation. Since there are two separate parcels being sold, there is the possibility of multigenerational living with two separate homesites. The current owner has been thoughtful with how the fields are arranged so they all lead into a main ally/driveway for ease in moving livestock to and from pastures and to working pens. There are two barns on the property, a 4 bent tobacco barn and a barn used for hay storage. Three automatic waterers are already in place to supplement the existing 7 ponds. 665 Lillies Ferry and 295 Cottman Lane are selling together.

665 Lillies Ferry Rd, Winchester

160 Agawam Rd, Winchester
$524,000
3 Beds ⋅ 3 Baths ⋅ 25015815 MLS
Welcome to this beautifully maintained brick ranch home set on a spacious and private 5-acre fenced lot. This versatile property offers the perfect blend of comfort, functionality, and rural charm - ideal for families, hobby farmers, or equestrian enthusiasts. Inside, you'll find 3 bedrooms and 3 bathrooms with a fully finished basement that offers ample space for additional bedrooms, a home gym, or a rec room. There is plenty of storage throughout, making organization a breeze. Step outside and you'll find a detached 2-car garage featuring a finished office space that could easily be converted into a mother-in-law suite, guest quarters, or home business setup. Horse lovers will appreciate the large metal barn with multiple stalls, and there is plenty of room for gardening with established garden beds ready for your green thumb. Multiple fruit trees on the property as well! This is a rare opportunity to own a peaceful slice of the countryside with modern conveniences and room to grow. Don't miss your chance to make this unique property your forever home! Agent /Owner Property. Option to sell furnished! Wanting more than 5 acres? Adjoining 7.44 acres available!

160 Agawam Rd, Winchester

838 Bypass Rd, Winchester
$520,000
25015909 MLS
Own a highly visible, freestanding retail building in one of Winchester's busiest commercial corridors. This 2,906-square-foot property offers turn-key potential for your next business or investment. The interior features a wide-open layout, ready for your vision, along with two restrooms. Located less than a mile from I-64 and just two miles from downtown, the property is surrounded by established retailers and benefits from prominent signage opportunities and visibility from approximately 30,000 vehicles per day. Per deed restrictions, no restaurant or bar may operate at this location until April 12, 2027. Zoned B-3 (Highway Business), this flexible space is ideal for a variety of retail or service-based uses. Property is being sold AS-IS.

838 Bypass Rd, Winchester

919 Elkin Station Rd, Winchester
$498,325
3 Beds ⋅ 2 Baths ⋅ 26020312 MLS
Enjoy country living on approximately seven acres at 919 Elkin Station Road! A welcoming wraparound front porch sets the tone for this spacious three-bedroom, two-bath home featuring beautiful hardwood floors throughout. The kitchen is enhanced by granite countertops, while a charming sunroom offers a cozy place to relax and enjoy the surrounding views. A versatile bonus room is perfect for a home office, playroom, guest space or potential fourth bedroom. The partially finished basement provides even more room to relax and entertain, featuring a bar, pool-table area, separate den area and spacious built-in wall gun safe. Outside, spend summer days by the above-ground pool and surrounding deck, then unwind in the hot tub. A detached two-car garage provides additional parking and storage. The property also includes a 2,880-square-foot barn equipped with electricity and a cistern providing a convenient water source, making it ideal for equipment, storage, hobbies or agricultural use. With abundant indoor and outdoor living space, acreage and exceptional outbuildings, this property offers the privacy and versatility of country living while remaining convenient to Winchester.

919 Elkin Station Rd, Winchester

808 Bypass Rd, Winchester
$485,000
1 Baths ⋅ 26008729 MLS
Mixed-use commercial opportunity with income potential in a high-visibility location just minutes from I-64. This versatile property offers a fully equipped commercial space currently operating as a bakery, complete with kitchen area, service counter, dining/event space, drive-thru window, outdoor seating, and on-site parking. Attached to the commercial space is a private-entry apartment, ideal for rental income, owner occupancy, or employee housing. An additional unfinished area already plumbed for a second one-bedroom apartment provides future expansion and added investment potential. With strong traffic exposure along the bypass and flexible layout options, this property could accommodate a variety of uses including café, bakery, restaurant, retail, office, or other service-based businesses. Excellent opportunity for an owner-operator, investor, or entrepreneur looking for a live/work setup or multi-income property. Business is not included in the sale. Select equipment may be negotiable.

808 Bypass Rd, Winchester

414 Fairholme Way, Winchester
$484,900
4 Beds ⋅ 3 Baths ⋅ 26011136 MLS
Step into a lifestyle where modern luxury and brand-new construction come together seamlessly. This home is perfectly positioned with golf course views and unforgettable sunset skies, this newly built home offers the kind of setting that turns ordinary evenings into your favorite part of the day—without sacrificing style, comfort, or convenience. Inside, soaring vaulted ceilings and a warm fireplace create an inviting centerpiece for the open-concept living space—designed for both effortless entertaining and cozy nights at home. The timeless kitchen is equal parts beautiful and functional, featuring quartz countertops, a spacious walk-in pantry, and a dedicated coffee bar nook ready to elevate your morning routine. Just beyond, a dedicated dining area creates the perfect backdrop for weeknight dinners, holiday gatherings, and lingering conversations with family and friends. The primary suite feels like a private retreat, offering a spa-inspired en-suite complete with a soaking tub, tiled walk-in shower, dual vanities, and an expansive custom closet designed with luxury in mind. A split-bedroom floor plan provides ideal privacy with three additional bedrooms and two full bathrooms, creating flexibility for guests, family, or a home office setup. Outdoor living provides a screened back patio made for slow mornings, relaxing evenings, and enjoying the peaceful views. Whether you're gardening, unwinding after a long day, or gathering on the front porch with friends as the sun sets over the golf course, this space was designed to be enjoyed. And the location? Exceptional. Nestled just minutes from charming downtown Winchester's local shops, restaurants, and small-town charm, with quick access to I-64 for an easy commute. Plus, the oversized tall garage offers incredible vertical storage opportunities for hobbies, equipment, and all of life's extras. A rare opportunity to enjoy the ease of new construction, elevated design, and a lifestyle centered around comfort, connection, and beautiful surroundings. This isn't just a home—it's your next chapter.

414 Fairholme Way, Winchester

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