Winchester Real Estate Search

Winchester Homes for Sale

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Newest Winchester Homes for Sale

26019968 MLS ⋅ 1,900 SqFt. ⋅ ACTIVE Status

Located on the very visible corner of Lexington Avenue and Main Street, this property has recently been updated. Wonderful tenants in both the upstairs and downstairs unit makes this a great investment property. The historic Leeds Center for the Arts, numerous other restaurants and shops are in walking distance. This is an ideal location for an investment property or bring your business here. This property is also located in the Opportunity Zone. Lots of 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, Loma's, 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! Property Highlights: -Excellent investment property with Tenants in place -Ideal location in Downtown Winchester -Located in the Opportunity Zone

1 N Main St, Winchester

3 Beds ⋅ 3 Baths ⋅ 26019961 MLS ⋅ 1,769 SqFt. ⋅ ACTIVE Status

Welcome to **236 Buffalo Trace in Winchester, KY**—where thoughtful design meets comfortable, one-level living. This well-maintained **3-bedroom, 2.5-bath** home features a desirable **split-bedroom floor plan**, offering added privacy for the primary suite while keeping family or guest bedrooms conveniently located on the opposite side of the home. The spacious main level is designed for everyday comfort, with all bedrooms located on the first floor. Just off the kitchen, you'll appreciate the convenience of a dedicated laundry room, making daily routines a breeze. One of the home's standout features is the **spacious sunroom**, providing the perfect place to enjoy your morning coffee, unwind with a good book, or take in the peaceful views year-round. Step outside to a backyard framed by a **lush tree line**, creating a private, picturesque setting that's ideal for relaxing or entertaining. The **partially finished basement** offers valuable additional living space with endless possibilities—whether you're looking for a recreation room, home office, fitness area, or hobby space—while still providing room for storage. Conveniently located near shopping, dining, schools, and everything Winchester has to offer, this home combines a functional layout with the tranquility of a beautiful backyard setting. Don't miss your opportunity to make **236 Buffalo Trace** your next home!

236 Buffalo Trce, Winchester

3 Beds ⋅ 2 Baths ⋅ 26019908 MLS ⋅ 1,955 SqFt. ⋅ ACTIVE Status

Welcome to 108 Milwood Drive\! Nestled in one of Winchester's most desirable neighborhoods, this well\-maintained 3\-bedroom, 2\-bath ranch offers a functional floor plan and peaceful backyard setting\. The spacious living room features a gas log fireplace, while the primary suite includes a private en suite bath\. A cozy den opens to a wooden deck overlooking the fenced backyard and wooded views—perfect for relaxing or entertaining\. The semi\-finished walkout basement provides additional living space and a rear\-entry garage for added convenience\. Don't miss this opportunity to own a home that combines comfort, privacy, and a great location\!

108 Milwood Dr, Winchester

26019866 MLS ⋅ ACTIVE Status

Rare opportunity to acquire approximately 120 acres of magnificent, rolling Bluegrass farmland in prime Clark County! This exceptionally versatile property features a ideal blend of cleared pasture and rich wooded land, making it perfectly suited for cattle, horses, recreational pursuits, or building your private dream estate.Equipped with a large pond, barn, and county water available at the road, this land is ready for active agricultural or equestrian use. Enjoy rolling terrain with picturesque countryside views and excellent hunting/recreational opportunities right in your back yard. Conveniently located just minutes from downtown Winchester with quick, seamless access to I-64, I-75, and the Mountain Parkway. Whether you are looking to expand an existing agricultural operation, secure a secluded hunting retreat, or establish a legacy family homestead, this property offers unmatched potential and privacy.

345 Providence Ln, Winchester

4 Beds ⋅ 3 Baths ⋅ 26019848 MLS ⋅ 2,496 SqFt. ⋅ ACTIVE Status

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

2 Beds ⋅ 2 Baths ⋅ 26019713 MLS ⋅ 1,054 SqFt. ⋅ ACTIVE Status

Don't miss this rare quadruplex opportunity in Winchester. Featuring four units (443, 445,447 and 449 Oxford Drive), this property is perfect for investors seeking multiple income streams in one location. Each unit offers a similar layout with approximately 1,054 ft, 2 bedrooms, and 1.5 baths. The photos shown are from one updated unit, and all units have comparable layouts—making this an ideal setup for consistent rental demand. The vacant property (449) can be viewed through scheduling via showing time and sentrikey box is on the back door, the other 3 units are occupied and can be viewed with 48 hours notice given to the tenants.

443 Oxford Unit 443,445,447,449, Winchester

5 Beds ⋅ 3 Baths ⋅ 26019610 MLS ⋅ 4,676 SqFt. ⋅ ACTIVE Status

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

25000480 MLS ⋅ ACTIVE Status

READY TO BUILD OR HUNT? We have the perfect spot for you! Mostly wooded 8.35 acres, tract 2B, of green, treed, Bluegrass Heaven. Close proximity to I 75 and I 64 as well as Lexington, Richmond, and Winchester. Bring your own builder or we can help you find one!

6699 Boonesboro Rd, Winchester

3 Beds ⋅ 2 Baths ⋅ 26019273 MLS ⋅ 2,358 SqFt. ⋅ ACTIVE Status

Welcome to 125 Amiens Boulevard, where quality craftsmanship, thoughtful design, and everyday comfort come together in one exceptional home. Built by respected local builder Marcus Moore, this beautifully maintained all-brick ranch has been lovingly cared for and is truly move-in ready. From the moment you arrive, you'll appreciate the inviting curb appeal, spacious floor plan, and attention to detail throughout.The open-concept living area creates the perfect setting for entertaining or relaxing at home, while the well-designed kitchen offers abundant cabinetry, generous workspace, and appliances that convey with the home, making your move that much easier. Buyer to verify listing details. See attached improvements in documents.

125 Amiens Blvd, Winchester

3 Beds ⋅ 2 Baths ⋅ 26019263 MLS ⋅ 1,990 SqFt. ⋅ ACTIVE Status

This three bedroom home has been updated, new painting interior and exterior, new flooring, new light fixtures, new bath vanities, new granite in kitchen plus much more. Owner/Broker

11 Stoney Brook Dr Unit 1, Winchester

3 Beds ⋅ 2 Baths ⋅ 26019259 MLS ⋅ 1,356 SqFt. ⋅ ACTIVE Status

Welcome home to this beautifully maintained 3 bedroom, 2 bath home offering comfort, style and fantastic outdoor living! The spacious two-car garage provides plenty of room for parking and storage, while the fully fenced backyard with a new privacy fence creates the perfect space to relax or entertain. Step outside to enjoy the inviting covered outdoor entertaining area, complete with lighting and a small refrigerator-ideal for grilling, hosting friends, or enjoying quiet evenings at home. You'll also appreciate the screened-in back patio, offering a peaceful place to unwind while overlooking the beautifully landscaped yard. The property features mature fruit trees, including a peach and apple trees, adding both charm and seasonal enjoyment. With attractive landscaping surrounding the home and thoughtful outdoor amenities, this property is ready for you to move-in and enjoy. Don't miss the opportunity to make this wonderful home yours!

316 Buffalo Trce, Winchester

3 Beds ⋅ 2 Baths ⋅ 26019206 MLS ⋅ 1,297 SqFt. ⋅ ACTIVE Status

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

3 Beds ⋅ 2 Baths ⋅ 26019157 MLS ⋅ 1,512 SqFt. ⋅ ACTIVE Status

Enjoy peaceful country living on this beautiful 2+ acre property featuring a nearly new manufactured home and a spacious barn. Surrounded by scenic countryside views, this property offers plenty of privacy, comfort, and room to enjoy the outdoors. The well-kept home provides a cozy place to relax, while the large barn and open space give you plenty of options for storage, hobbies, gardening, animals, or recreation. Take in quiet mornings, beautiful sunsets, and the charm of wide-open spaces while still being close to nearby amenities. A great opportunity to own a slice of the country and make it your own.

4305 Old Boonesboro Rd, Winchester

3 Beds ⋅ 3 Baths ⋅ 26019133 MLS ⋅ 2,204 SqFt. ⋅ ACTIVE Status

Welcome to this superbly maintained home located in one of the area's most desirable neighborhoods. Offering 11 spacious rooms, this property delivers exceptional comfort, versatility, and charm. A beautiful front wrap around covered porch creates an inviting first impression, perfect for relaxing or greeting guests. The rear of the home features a covered back porch and an adjoining open deck, ideal for outdoor dining, entertaining, or enjoying peaceful evenings. An outbuilding provides valuable additional storage or workspace. Convenience is unmatched—you're just a few minutes from shopping, restaurants, golf courses, and the bypass, making daily living effortless while still enjoying the tranquility of a well established community. This home truly has so much to offer and is a must see for buyers seeking comfort, location, and lifestyle.

322 Calmes Blvd, Winchester

4 Beds ⋅ 2 Baths ⋅ 26017258 MLS ⋅ 3,306 SqFt. ⋅ ACTIVE Status

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

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