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30 Virginia Ave, Winchester
$229,000
3 Beds ⋅ 1 Baths ⋅ 26013434 MLS
Welcome to a well maintained 3 bedroom 1 full bath home that has been lovingly cared for by only two owners since 1962. Recent updates include new flooring and completed repairs, makiing this property ready for a new owner, while preserving its timeless character. Beautiful hardwood floors add warmth and charm throughout the home. Enjoy relaxing or entertaining on the comfortable spacious patio perfectly sized for gatherings. The brick fireplace with gas logs, located in the living room, adds a cozy ambience on cool evenings. One of the property's standout features is its prime location backing directly to Legacy Grove Park complete with a private gate providing conveninent park access. This unique setting offers addttiional outdoor space, scenic views and a peaceful atmosphere right in your own backyard. . This is a wonderful opportunity to call a well cared for property with an abundance of charm your very own.

30 Virginia Ave, Winchester

414 Alexis Way, Winchester
$665,000
3 Beds ⋅ 3 Baths ⋅ 24025581 MLS
Introducing the Alexis, a stunning all-brick ranch home with incredible curb appeal and a charming front porch. This thoughtfully designed 3-bedroom, 2.5-bath home features a desirable split-bedroom layout, offering privacy and comfort. The spacious primary suite includes a luxurious ensuite with double vanities, a walk-in closet with direct access to the separate utility room for added convenience. The open-concept kitchen flows seamlessly into the great room, which is highlighted by a gas log fireplace and built-in cabinetry. The kitchen is a chef's dream, featuring a large island, a cozy breakfast area, and a walk-in pantry for ample storage. The Alexis also includes a formal dining room, perfect for entertaining, along with a convenient drop zone with a bench for everyday use. With 9-foot ceilings and luxury vinyl plank flooring throughout, this home combines modern elegance with functionality. A 2-car attached garage completes this exquisite floor plan. Let'c customize your dream home in Mallard Cove with CP Builders!

414 Alexis Way, Winchester

1015 Old Stone Church Rd, Winchester
$1,500,000
25502084 MLS
Right off of Boonesboro Road lies 60.65± acres of Kentucky history waiting for its next chapter! This remarkable property sits along historic Howard's Creek and is located on the site of the original Bush Settlement—one of the earliest settlements in Kentucky. Formerly a working tobacco farm, this versatile acreage offers opportunities for cattle, hay, or crops, with timber and mineral rights conveying. Wildlife is abundant, with wild turkey and deer frequently spotted across the land. A rare stone fence surrounds the property, adding to its timeless character. The land neighbors Old Providence Church—now known as Old Stone Church—Kentucky's 11th oldest standing building, dating back to 1793, where legendary frontiersman Daniel Boone was once a member. Whether you're seeking farmland, recreation, or an investment in Kentucky's past, this property offers a chance to own a genuine piece of Bluegrass history. Schedule a showing today and experience it for yourself! Buyer to satisfy themselves with survey and all property information. More Photos Coming Soon!

1015 Old Stone Church Rd, Winchester

16 N Main St, Winchester
$299,999
25001584 MLS
An excellent opportunity to own a fully leased, income-producing property in the heart of Downtown Winchester, Kentucky. This beautifully renovated 2,310 SF retail storefront is being offered at a 10% cap rate, making it an attractive turnkey investment from day one. The building may be old, but nearly everything inside is new! Recent improvements include a new roof, four new skylights, exposed beams, new hardwood flooring throughout, updated electrical and plumbing, and HVAC. The space is plumbed for four bathrooms and also includes a laundry room and private back office with a window overlooking the main retail area. This property boasts a large rear parking lot—one of the largest in Downtown Winchester—providing convenient parking for tenants, customers, and employees. The location is surrounded by continued downtown growth. Seven new high-end apartments across the street, while the same block is already home to five restaurants, numerous shops, and the Leeds Center for the Arts. Property Highlights: -Recently renovated with a new roof, 4 new skylights, exposed beams, new hardwood floors, new plumbing and new electrical. -The property is located directly across from a brand-new apartment building and is surrounded by retail and restaurants. -The property boasts the largest back parking lot in the downtown area, a bonus for staff and customer accessibility. -Downtown Winchester, KY is booming - everyone wants to be Downtown, introducing shops, restaurants, and new apartment living options. Winchester, KY is conveniently situated just 18 miles east of Lexington and, with proximity to I-64, provides quick access to the larger city's amenities. Downtown Winchester is home to a variety of beloved local establishments, including the historic Leeds Center for the Arts, La Trattoria, The Hall Coffee & Social Club, and several small shops. Over 30 new, high-end apartments are coming to Downtown Winchester - residents and tourists want to be Downtown!

16 N Main St, Winchester

107 Hibiscus Ln, Winchester
$369,900
4 Beds ⋅ 3 Baths ⋅ 26015608 MLS
Welcome to 107 Hibiscus, where thoughtful updates, quality craftsmanship, and exceptional maintenance come together in this spacious 4-bedroom, 2.5-bath home. Offering a versatile floor plan with generous living spaces, this move-in-ready property has benefited from approximately nearly $70,000 in improvements over the past several years, providing peace of mind and modern finishes throughout. Major mechanical updates include replacement heat pumps (downstairs in 2020 and upstairs in August 2024), all new energy-efficient windows installed in 2025 with a transferable 10-year warranty, a new three-panel sliding back door, recently cleaned ductwork, spray-foam insulated crawl space, additional attic insulation, a roof replaced approximately 8-10 years ago, and garage doors replaced approximately two years ago. Inside, you'll appreciate the beautiful ¾-inch solid oak hardwood flooring throughout the main level, fresh interior paint, updated light fixtures, ceiling fans, new door hardware, elegant crown molding, a cozy gas log fireplace, and renovated bathrooms featuring updated tile, mirrors, lighting, faucets, and refreshed cabinetry. The beautifully updated kitchen is designed for both everyday living and entertaining, offering new granite countertops, freshly painted cabinetry, all-new stainless steel appliances including a gas range, dishwasher, microwave, and refrigerator, plus a convenient coffee bar that adds both style and functionality. Outdoor living is just as impressive with a large deck, a freshly painted front porch, and a high-quality custom-built storage shed constructed with 12-inch studs for exceptional durability. If you're searching for a meticulously maintained home where many of the major updates have already been completed, 107 Hibiscus deserves a place at the top of your list. Buyer to verify all aspects of the property, including but not limited to square footage, schools, boundaries, and any information deemed important to the purchase. Schedule your showing today!

107 Hibiscus Ln, Winchester

443 S Maple St, Winchester
$325,000
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

101 Alabama St, Winchester
$155,900
1 Beds ⋅ 2 Baths ⋅ 26007407 MLS
Step back in time and discover the possibilities in this classic 1930-built home full of character and opportunity! With solid bones and vintage details, this property is the perfect canvas for investors, renovators, or anyone dreaming of restoring a piece of history. Featuring spacious rooms, original architectrual touches, and a layout just waiting to be reimagined. This home offers incredible potential to create something truly special. While its in good condition it is ready for some TLC, the price reflects the opportunity to build equity and customize to your taste. Whether you're looking to flip, rent, or make this your forever home, this property is packed with promise. Bring your vision and make it shine again! Opportunities like this don't come around often, so schedule your showing today!!!

101 Alabama St, Winchester

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