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$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
$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
$296,000
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
$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
$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
$1,695,000
3 Beds ⋅ 3 Baths ⋅ 26011538 MLS
Not sure what you are looking for, but see if this property checks enough boxes for you. This beautiful 33± acre estate offers the perfect blend of country charm, modern comfort, and endless opportunity. The stately historical home, built in 1919, offers a rare opportunity to own a true piece of Kentucky history . Enjoy stunning mountain views — perched at one of the highest points in Clark County, where you can see the panoramic views stretching all the way to the dormitories at EKU in Richmond and the mountains near Berea, KY. Relax by the newly lined in-ground pool with a new cover, and unwind in the hot tub while taking in the beautiful sunrise and sunset views — perfect for family gatherings or quiet evenings under the stars. The property features a two-level barn with horse stalls, a tack room, and a spacious open arena — ideal for equestrian enthusiasts. The upper level of the barn provides versatile space for auto storage or a workshop, while the fenced pastures and horse ring make it ready for boarding or training horses. This property also includes a stocked pond, adding to the tranquil landscape, and 2 gated driveways with a security system for peace of mind. The land features mature trees, including fig, pear, and apple. This is the first property on Colby Road out of Winchester with agricultural zoning, a very private estate, and the first time in 40 years this remarkable property has been for sale. Conveniently located just one mile to Kroger, Lowe's, and Walmart, and approximately 20 min. from Man O War via Todds Rd. Lexington. This property offers both peaceful seclusion and easy access to amenities. With potential for income from horse boarding and a rental home on the property, this exceptional farm is more than a home- it's a lifestyle, an investment, and a place to create lasting memories for generations to come.

3166 Colby Rd, Winchester
$115,000
3 Beds ⋅ 1 Baths ⋅ 26014899 MLS
Welcome to 25 Oliver Street, an affordable 3 bedroom, 1 bathroom ranch home in Winchester offering a practical blend of charm and investment potential. With 900 sq ft of first-floor living space, this home features a comfortable layout with vinyl flooring and a manageable single-level design that works well for homeowners, renters, or buyers looking to build equity. The unfinished basement with interior and exterior access adds valuable storage, utility space, and future potential. With under-utilized *R-4 Zoning*, an intelligent investor may uncover additional return on investment. The front porch and rear deck create simple outdoor spaces to relax and enjoy. This property offers the everyday essentials buyers look for at an approachable price point. Whether you are searching for a personal home, a rental property, or your next value-add opportunity in Winchester, this Oliver Street home is worth a closer look.

25 Oliver St, Winchester
$329,900
26014051 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
$699,000
26004697 MLS
Operated for over 20 years as a physician's office this two-story building features a "ready to go" office on the main floor with two large apartments on the second floor with walkup, outside entry. The entire structure is on an unfinished basement perfect for storage and access to the mechanical systems. There is also a detached 3-bay garage for parking and storage as well as an asphalt parking lot with more room for more than 25 vehicles.

218 S Maple St, Winchester
$825,000
3 Beds ⋅ 3 Baths ⋅ 24025579 MLS
Welcome Home to the Park Place Floor Plan by CP Builders. This elegant ranch home features all-brick construction and a thoughtfully designed split bedroom layout for maximum privacy. The open floor plan seamlessly connects the living, dining, and kitchen areas, creating a warm and inviting atmosphere. The spacious kitchen is a chef's dream, boasting a large island, a convenient pantry, and a cozy breakfast nook. The luxurious primary suite offers a private retreat with an ensuite bathroom and a walk-in closet. Every bedroom in this home features a walk-in closet, providing ample storage space for the whole family. Additional features on the first floor include a formal dining room, a dedicated study perfect for working from home, a half bath for guests, and an additional full bathroom. This desirable lot also includes an unfinished walkout basement, offering endless possibilities for expansion or customization. Make the Park Place your dream home. Reach out today to schedule a consultation with our experienced team and bring your vision to life.

111 Bella Shae Way, Winchester
$670,000
3 Beds ⋅ 2 Baths ⋅ 24025580 MLS
Introducing the Hampton, a beautiful all-brick ranch home. This 3-bedroom, 2-bath split-bedroom design offers both privacy and comfort. The spacious primary suite is a true retreat, featuring a luxurious ensuite with double vanities, a walk-in shower, and dual walk-in closets. The open-concept kitchen and great room are perfect for entertaining, highlighted by a gas log fireplace, a large kitchen island, and a generous walk-in pantry, along with a convenient butler's pantry for added storage and prep space. Nine-foot ceilings and luxury vinyl plank flooring throughout add a touch of elegance, while the separate utility room offers practicality. The additional two bedrooms also include walk-in closets. With a formal dining room, unfinished walkout basement, and a two-car garage, this home combines stunning curb appeal with modern functionality. Come build your dream home in Mallard Cove neighborhood!

113 Bella Shae Way, Winchester
$188,500
3 Beds ⋅ 1 Baths ⋅ 26006789 MLS
Property qualifies for USDA zero dollar down financing! Great Opportunity for First-Time Homebuyers! This charming 3-bedroom, 1-bath home features beautiful hardwood floors, an updated kitchen, and a fenced backyard perfect for relaxing, entertaining, or pets. Move-in ready and full of value, this is a wonderful opportunity to own a home with both character and convenience. Schedule your showing today!

41 Hiawatha Trl, Winchester
$189,900
2 Beds ⋅ 1 Baths ⋅ 25506124 MLS
Brick ranch in the College Park neighborhood. Large living area and kitchen with updated appliances and mechanicals (water heater and heat pump). The previous owner water proofed the basement and a new garage door has been installed. Bonus room could be utilized as an additional living room or bedroom.

605 College St, 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
$785,000
4 Beds ⋅ 3 Baths ⋅ 25000149 MLS
Introducing the Highland, an elegant all-brick ranch home offering 4 bedrooms and 2.5 full baths in a thoughtfully designed split-bedroom layout. The spacious primary suite is a true highlight, featuring a luxurious tile shower, separate soaking tub, double vanities, and a large walk-in closet. The open-concept kitchen flows seamlessly into the great room, creating the perfect space for entertaining, with a gas log fireplace, oversized island, and a generous walk-in pantry. This kitchen also features adjacent dining area. The Highland also offers a separate, spacious utility room, and a 2-car attached garage for convenience. Nine-foot ceilings and luxury vinyl plank flooring throughout add to the home's modern appeal. With its stunning double entry doors and stylish curb appeal, the Highland blends comfort, functionality, and timeless design into one perfect home. This desirable lot also includes an unfinished walkout basement, offering endless possibilities for expansion or customization. Experience the perfect blend of style and practicality in the Highland floor plan. Come build the Highland in Mallard Cove with CP Builders!

425 Alexis Way, 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
$99,900
3 Beds ⋅ 2 Baths ⋅ 26011430 MLS
If your looking for a fixer upper, this is it. House on 2 acres in the country with lots of potential. Laundry is off the kitchen, but floor is soft from a water leak. From the kitchen you will see a guest bath, dining and living area. To the left is a hallway that leads to 2 bedrooms, drywalled just needs to be finished. To the right of the living area is your master bedroom and bath. With some muscle and creativity, could make a great home.

2799 Pine Ridge Rd, Winchester
$340,000
4 Beds ⋅ 2 Baths ⋅ 26008225 MLS
Full of history and charm, this 1905 home sits on one of Winchester's most beloved and cherished streets, a place where homes like this are held onto for generations. It offers a rare opportunity to own a piece of the past while creating something truly your own. The inviting, oversized front porch sets the tone, perfect for quiet mornings, evening conversations, and the simple moments that make a house a home. Out back, the large, lush yard provides a peaceful setting with plenty of space to gather, garden, or unwind. Inside, the main level offers generous and flexible living space, including a first-floor bedroom, formal living room, den, dining room, kitchen, full bath, and utility area. The standout sunroom is a bright and airy retreat, heated and cooled, with vaulted ceilings, skylights, and beautiful views of the backyard year-round. Upstairs features three bedrooms and a full bath, continuing the home's classic layout (note: no central heat and air on the second floor). An oversized one-car attached garage and ample driveway parking add everyday practicality, something not often found in homes of this era. Being offered as an estate sale, this home has been lovingly cared for over the years and reflects a lifetime of memories. It now awaits its next chapter, someone who will appreciate its history, honor its character, and bring new vision to what it can become.

443 S Maple St, Winchester
$265,000
3 Beds ⋅ 2 Baths ⋅ 26012820 MLS
Beautifully updated and move-in ready, this 3-bedroom, 2-bath home offers comfort, style, and versatility throughout. Inside, you'll find a spacious living room, an updated kitchen with ample cabinetry, tile showers, original hardwood, modern LVP, and thoughtful finishes throughout. A large utility room offers flexible space for a home office, playroom, or extra storage. The unfinished basement, two-car detached garage, fully fenced backyard, patio, and covered front porch add even more function and charm. Recent updates include HVAC/furnace, roof shingles, windows, vinyl siding, flooring, kitchen cabinetry, bathroom vanities, light fixtures, doors, and hardware. With so much already done, all that's left to do is move in and enjoy.

20 Jackson St, Winchester
$700,000
3 Beds ⋅ 2 Baths ⋅ 24025582 MLS
Introducing the Merango, a classic all-brick ranch home designed for both comfort and style. With stunning double front doors and a 2-car attached garage, this home offers incredible curb appeal and modern living. The spacious 3-bedroom, 2-bath layout features a split-bedroom design for added privacy, along with a dedicated study perfect for a home office. The open-concept kitchen is ideal for entertaining, featuring a large island, walk-in pantry, and seamless flow into the great room, complete with a cozy gas log fireplace. The luxurious primary suite offers a walk-in closet, double vanities, and a tile shower with a soaking tub for ultimate relaxation. Nine-foot ceilings and luxury vinyl plank flooring throughout enhance the home's bright, airy feel. Additional highlights include a separate utility room and an unfinished walkout basement, providing endless possibilities for expansion. The Merango offers the perfect blend of functionality, elegance, and comfort. Let's customize your dream home in Mallard Cove with CP Builders!

415 Alexis Way, Winchester
$247,500
3 Beds ⋅ 2 Baths ⋅ 26013350 MLS
"Motivated sellers—bring your offers!" Step into this charming 3-bedroom, 2-bath home that's full of character and timeless appeal. From the beautiful hardwood floors to the inviting living spaces, this older home offers warmth and personality you simply don't find in newer construction. The spacious living room provides plenty of room to relax or entertain, while the separate dining room is perfect for family meals and special gatherings. The large kitchen offers abundant space for cooking, storage, and everyday living. Outside, you'll enjoy a fully fenced backyard that's ideal for children, pets, gardening, or outdoor entertaining. Sip your morning coffee on the welcoming covered front porch or unwind on the back deck overlooking the private yard. This home offers the perfect combination of classic charm, generous living space, and inviting outdoor areas. Don't miss this wonderful opportunity to make this charming home your own!

377 Crescent Ave, Winchester
$359,000
3 Beds ⋅ 3 Baths ⋅ 26015128 MLS

608 Colby Rd, Winchester
$1,349,000
4 Beds ⋅ 5 Baths ⋅ 26013734 MLS
Discover elevated living on 2.5 acres! This 3,350 sqft custom masterpiece boasts 4 bedrooms, 4.5 bathrooms with an open 2,670 sqft main level. Featuring custom solid oak cabinetry not only in kitchen, but master closets, pantry and utility areas. Custom Showers and tile in each bathroom throughout the home. Gas and electric fireplaces located in great room as well as primary first floor bedroom. Head upstairs to the spacious 680sqft recreation room with its own full bathroom and attic storage access. Step outside to your large, spacious covered patio, personal inground pool with spa and sunken inground fire pit for endless entertaining. 3-Car garage offers ample storage. The 2670sqft Walk-out basement is a blank canvas with endless opportunities. Basement can be finished by builder at buyer's discretion. Some additional selections may be available. LUXURY, SPACE and PRIVACY just minutes from town.

1200 Craig Xing, Winchester
$299,999
3 Beds ⋅ 3 Baths ⋅ 26004053 MLS
This beautiful 1.5-story home offers all the charm of downtown in a small town, with a library, park, and restaurants nearby. Plus, just minutes to Lexington when the city is calling your name. This home has been remodeled for modern living, featuring an open floor plan. There is plenty of room for entertaining with a beautiful, well-equipped kitchen and a large island open to both the dining space and the living room. The first floor features all the luxuries, including a primary suite with an ensuite bathroom and a large walk-in closet, a dedicated laundry/mud room, and a powder room. Upstairs, you'll find two spacious bedrooms and an additional bathroom. The entertaining doesn't have to stop inside, as there is also a covered patio and a large fenced-in backyard ready for play. There's so much to this charmer, including a covered parking spot and an unfinished basement for additional storage.

322 S Burns Ave, Winchester