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$299,900
4 Beds ⋅ 3 Baths ⋅ 26015653 MLS
Very motivated sellers, Get here first, make an offer on this 4 bedroom, 3 bath, 1 1/2 story home, 2 car garage, showroom fresh condition, vaulted ceiling, hardwood floors, tile, carpet, deck, nice back yard, call today to view.

209 Connie Ln, Winchester
$270,000
20111867 MLS
Visibility, Access, Utilities on site per seller/per plat buyer to verify, zoned B-3. .84 acres located and visible at I-64 exit 96, buyer to verify and satisfy themselves to all aspects and information on property and or inspections sold as is. Buyer to verify water, gas, and electric locations and availability.

800 Interstate Dr, 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
$300,000
20111875 MLS
Easy Location, Metal/Pole Barn approx 1675sqft, type garage on site with three 10x10 garage doors, two 8ft doors and 2 entrances, currently split access to each side, Utilities on site per seller/per plat, water and gas is not hooked up to building, zoned B-3. .58 acres located at I-64 exit 96, buyer to verify and satisfy themselves to all aspects and information on property sold As Is buyer to verify all information and access to water, gas, electric and locations. Per seller egress and ingress rights down Holiday Drive to building.

1045 Early Dr, Winchester
$249,500
26007074 MLS
Discover the perfect blend of beauty, privacy, and opportunity with this stunning 14.511-acre tract on Irvine Road. Featuring gently rolling hills, this property offers multiple ideal building sites to bring your dream home to life, whether you're envisioning a modern farmhouse, barndominium, or private country retreat. A barn is already in place, adding immediate functionality for storage, livestock, or future homesteading plans. The property also includes partial fencing, making it even more appealing for those looking to accommodate animals or create a mini-farm setup. One of the standout features is the picturesque creek that runs through the property, adding both natural beauty and a peaceful setting you'll enjoy year-round. With a balance of open space and scenic landscape, this land offers the kind of tranquility that's getting harder to find while still being conveniently located near town. Looking for even more space? The adjoining 11.362-acre tract (MLS #26007067) is also available, creating a rare opportunity to own over 25 acres of contiguous land. perfect for a private estate, multi-generational living, or future investment potential. Whether you?re ready to build now or invest for the future, this property checks all the boxes for Kentucky land buyers seeking space, scenery, and flexibility. Don't miss your chance to own a slice of Kentucky countryside! RESTRICTIONS MAY BE REMOVED BY SELLER IF BOTH TRACTS 2996 AND 3056 ARE PURCHASED. Schedule your showing today.

3056 Irvine Rd, Winchester
$250,000
26013923 MLS
Exciting opportunity for congregations, investors, or visionaries seeking a one-of-a-kind property! This spacious one-level property offers over 2,500 sq ft with 2 bathrooms, a roof that is approximately 6 years old, and endless possibilities for renovation or repurposing. Situated on a quiet street, this unique space provides the perfect canvas to bring your vision to life. Property is being sold as-is. Buyers to verify square footage and lot size.

3150 Waterworks Rd, Winchester
$258,900
2 Beds ⋅ 1 Baths ⋅ 26013194 MLS
Newly renovated Cabin sitting on +- 5 acres. Renovations began in 2024 and were completed in 2026. An ideal property for a first-time home buyer or anyone looking for a remote quiet location located within 20 minutes of downtown Winchester.

955 Right Angle Rd, Winchester
$239,000
4 Beds ⋅ 4 Baths ⋅ 26000922 MLS
Duplex. Both units are being sold together. Great income-producing potential. Each side offers a nice sized vaulted Great room that opens to the kitchen, 2 bedrooms, 1.5 baths, a laundry room, and a 1-car garage. Nice private backyard for side with lots of trees. 1130 has a new HVAC. Selling As Is Inspections Welcome.

1128-1130 Dale Dr, Winchester
$239,900
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. All this in a great location, just minutes from Lexington, the horse capital of the world, with beautiful Kentucky horse farms! And just 45 minutes from the famous Red River Gorge! This home is right in the center of it all, city life and the beautiful outdoors! Don't miss this wonderful opportunity to make this charming home your own!

377 Crescent Ave, Winchester
$280,000
3 Beds ⋅ 3 Baths ⋅ 26011097 MLS
Space, updates, and charm all come together in this spacious 2,260 square foot 1.5-story home located in the heart of Winchester! Recently updated and full of character, this property offers a flexible layout with room for everyone. The main level offers a welcoming living room, large family room, dining area, kitchen, laundry room, full guest bath, and a spacious primary suite complete with a private bath. Upstairs you'll find two additional generously sized bedrooms along with a convenient half bath. Enjoy relaxing mornings on the covered front porch made for rocking chairs or unwind on the covered rear porch overlooking the backyard. Additional features include two carports, storage building, rear drive access, fresh paint, some new flooring, central heat and air, and much more! Don't miss your opportunity to own this move-in ready home with space, updates, and charm throughout. Schedule your showing today! This is a Fannie Mae HomePath property.

209 Boone Ave, Winchester
$275,000
3 Beds ⋅ 2 Baths ⋅ 26007260 MLS
Simply the Best! 3 Bedroom, 1 1/2 bath All Brick ranch home located within walking distance to historic downtown Winchester, Country Club, Middle School, great place to live, you will spend most of your time on the Sunporch off the Kitchen, large lot, many updates, floor, bathrooms, new furnace, fresh paint, don't miss looking at this jewel, call today

103 Southern Ct, Winchester
$220,000
4 Beds ⋅ 3 Baths ⋅ 26004331 MLS
Turnkey downtown triplex with tenants already in place. An excellent addition to any investor's portfolio. Two units have been recently updated, while the third features a long-term tenant with future value-add potential. Property includes two 1BD/1BA units and one 2BD/1BA unit. Tenants pay all utilities directly except water, which is on a RUB system, keeping operating costs low. Strong income potential in a prime downtown location with continued upside. Selling as-is.

130 E Broadway St, Winchester
$274,500
3 Beds ⋅ 2 Baths ⋅ 26011465 MLS
Welcome to this delightful 1.5-story home perfectly situated on a spacious corner lot just off the Eastern Bypass and only minutes from I-64. Convenience meets comfort in this beautifully maintained property offering 3 bedrooms, 2 full baths, and an inviting layout designed for everyday living. Step inside to an open living area ideal for entertaining, a spacious kitchen and dining space, and plenty of room for family and friends to gather. Natural light fills the home, creating a warm and welcoming atmosphere throughout. Outside, enjoy an oversized backyard complete with a charming white picket fence — perfect for children, pets, gardening, or hosting outdoor entertaining. Whether you're a first time buyer or searching for your forever home, this property offers comfort, convenience, and character all in one. Call today for more information or to schedule your private showing. Note: Offer to Purchase with Contingency and Kick-out Clause. Buyer cannot perform without the sale of current property.

137 Eastridge Dr, Winchester