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955 Right Angle 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
935 Stoner-Ephesus Rd, Winchester
$515,000
3 Beds ⋅ 2 Baths ⋅ 26009385 MLS
Picture this: over five acres of Kentucky countryside, a handsome ranch-style home, and enough elbow room to finally breathe. This stunning 2,563 square foot retreat delivers the rare combination of refined interior finishes and genuine rural charm, all without sacrificing modern convenience. Inside, discover a generous family room anchored by a striking stone fireplace — the kind of space that practically begs for cozy evenings and lively gatherings alike. The kitchen shines with quartz countertops, stainless steel appliances, and classic shaker cabinetry, while a large pantry keeps everything organized and within reach. Elegant wood plantation blinds frame the views throughout, adding warmth and character to every room. Three bedrooms and two full bathrooms provide comfortable living for any household. The primary suite features a beautifully tiled shower that transforms your daily routine into something a little more luxurious. A bonus room situated above the garage offers flexible space perfect for a home office, playroom, or creative studio. Outside, the screened-in porch invites you to enjoy peaceful mornings surrounded by nature, and a detached workshop stands ready for projects big and small. The oversized utility room, complete with a mop sink, makes tackling life's messier moments refreshingly simple. Nearby Buffalo Ridge Ranch adds even more outdoor adventure to your doorstep. Properties like this — where thoughtful craftsmanship meets wide-open acreage — simply do not come along every day. Schedule your private showing and discover what country living at its finest truly feels like.

935 Stoner-Ephesus Rd, Winchester
7950 Four Mile Rd, Winchester
$123,000
25503896 MLS
Discover the perfect blend of privacy, nature, and convenience on this beautiful 11.47-acre tract located along Four Mile Road in Clark County. This unique property adjoins the scenic Four Mile Creek, offering a peaceful, picturesque setting ideal for those seeking a quiet country retreat or a place to build their dream home. The land features a mix of open and wooded areas, providing excellent potential for a permanent homesite, recreational getaway, or hunting retreat. Whether you envision mornings spent listening to the creek or evenings around a campfire surrounded by nature, this property delivers the ideal backdrop. On-site utilities remain from a former residence, making it even easier to bring your vision to life. Enjoy the tranquility of rural Kentucky living while still being within easy reach of Winchester, Lexington, and major highways. Don't miss this opportunity to own a versatile and scenic piece of land with endless possibilities along Four Mile Creek.

7950 Four Mile Rd, Winchester
990 Craig Crossing Rd, Winchester
$175,000
22004991 MLS
Lot # 13 contains 6.588 acres of gently rolling land perfect for your new home. This is a rare opportunity to own a piece of western Clark County real estate in the sought-after McClure Road area. Thoroughbred Estates is Winchester's newest upscale development containing 33 lots from 2 acres to nearly 7 acres. Lots are located just minutes from Winchester and Lexington.

990 Craig Crossing Rd, Winchester
4095 Basin Springs Rd, Winchester
$350,000
26014375 MLS
Looking for land to build your dream home that is private, but convenient? This 7+ acre beautiful lot is located in Clark County, just 15 minutes from Costco, Hamburg and I-75. No HOA or deed restrictions. The perfect place to build or have a small farm. City water and electricity available at the street. No city sewer.

4095 Basin Springs Rd, 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
9999 Portersburg Rd, Manchester
$319,900
26026402 MLS
Beautiful 76.97 Acre Clay County Kentucky Farm. Offering a versatile combination of rolling land, lush pastures, wooded acreage, and a large pond. The property provides excellent setting for cattle, horses, farming, recreation, and hunting, abundant wildlife abounds. Multiple open pasture areas offer plenty of room for livestock and agricultural use, while the wooded portions provide privacy and excellent wildlife habitat. The large pond adds both beauty and functionality to the property. Enjoy peaceful country living with abundant opportunities for outdoor recreation, hunting and making this property your own. A rare opportunity to own a substantial tract of productive and recreational land with lots of possibilities, just a few miles from London Kentucky and I 75.

9999 Portersburg Rd, Manchester
Hogskin Rd, Manchester
$199,000
26023296 MLS
Discover 140+/- beautiful acres nestled in a scenic valley just 8 miles from Manchester, Ky. This property offers approximately 1,000 feet of road frontage with two separate entrance roads providing convenient access. A beautiful homesite offers the perfect setting to build your dream home while enjoying the privacy and natural beauty of the surrounding land. Outdoor enthusiasts will appreciate the excellent hunting opportunity, with abundant deer and turkey throughout the property. Mineral rights and timber rights convey with the sale. A rare opportunity to own a large versatile tract of Kentucky land with endless possibilities.

Hogskin Rd, Manchester
6 Toby Rd, Manchester
$64,900
26022882 MLS
Secluded 46.46-acre wooded property featuring rolling hills, abundant wildlife, and excellent hunting opportunities. Includes harvestable timber and multiple potential building sites. Ideal for recreation, residential use, or investment. Enjoy a private setting with endless possibilities--conveniently located less than 10 minutes from Manchester, KY. Bring your vision and make it your own.

6 Toby Rd, Manchester
99 Jackson Rd, Manchester
$480,000
26022733 MLS
Privacy Abounds! this Approx. 240 acre tract of land offers the peaceful setting of country living. It has two beautiful creeks (one is Goose Creek ) that run through the property , and some clearing of good bottom land that can be used for growing crops, or for farm animals. Several areas for that beautiful home site to suit your needs. This mostly wooded hills has some marketable timber that also offers coal and hunting for you hunters out there. The recently cleared land offers a beautiful setting to call this place your on private get away.

99 Jackson Rd, Manchester
9999 Tanyard Rd, Manchester
$100,000
26019117 MLS
Are you ready to own a substantial piece of the beautiful Appalachian foothills? this 72 acres parcel of undeveloped, wooded land in the scenic Tanyard area of Clay County Ky is a rare find offering seclusion, natural beauty, and endless possibilities. This is a blank slate for your vision whether a cabin or a retreat! No zoning!

9999 Tanyard Rd, Manchester
48 Crescent Rd, Manchester
$129,900
3 Beds ⋅ 1 Baths ⋅ 26015780 MLS
Welcome home to this "cute as a button" remodeled 3-bedroom, 1-bath ranch offering the convenience of one-level living in a fantastic location! From the moment you arrive, you'll appreciate the inviting covered front porch—perfect for relaxing with your morning coffee or unwinding in the evening. Inside, you'll find a bright, updated interior featuring a remodeled kitchen with fresh painted cabinets and counter space, making meal preparation a breeze. The functional floor plan provides comfortable living with three bedrooms and a welcoming atmosphere throughout. Conveniently located just minutes from schools, shopping, dining, and other everyday amenities, this home offers the perfect combination of comfort and convenience. Whether you're searching for your first home, looking to downsize, or wanting an investment opportunity, this property checks all the boxes. Move-in ready and waiting for its new owners—don't miss your chance to see this wonderful home. Schedule your showing today!

48 Crescent Rd, Manchester
1153 Pawpaw Rd, Manchester
$270,000
3 Beds ⋅ 2 Baths ⋅ 26012539 MLS
Enjoy country living on 14.71 surveyed acres with this well-kept 2021 manufactured home offering 3 bedrooms, 2 full bathrooms, and approximately 1,860 sq. ft. of comfortable living space. This doublewide sits on a permanent foundation and features a metal roof with avalanche bracing, leaf guard gutter system, electric heat and cooling, underground electric, and a screened front porch perfect for relaxing and taking in the peaceful surroundings. The property includes a 40x30 detached insulated metal garage with 12-foot doors, RV hookups, and plenty of room for equipment, storage, hobbies, or workshop space. The acreage offers room to roam with four-wheeler trails, wildlife, and additional potential building sites. This property provides privacy, space, and flexibility. Appliances, washer/dryer, security system, and select furnishings may remain. Mineral rights convey per seller. A great opportunity for those looking for acreage, garage space, and quiet country living!

1153 Pawpaw Rd, Manchester
9999 Buzzard Rd, Manchester
$65,000
25504077 MLS
Escape the noise and discover the peace and freedom that comes with owning your own piece of Kentucky's natural beauty! This 17-acre tract of wooded land offers the perfect blend of seclusion, scenic views, and untapped potential. Whether you're an outdoor enthusiast, a weekend explorer, or someone dreaming of a private getaway, this property has something special to offer. With mature trees, rolling terrain, and abundant wildlife, it's an ideal spot for hunting, off-roading with ATVs, setting up a rustic campsite or cabin, or simply enjoying a quiet place to unplug and reconnect with nature. There's no HOA and no restrictions (buyer to verify), just raw, beautiful land ready for your vision. Whether you're looking for recreational use today or planning for future development, this 17-acre parcel is a rare find in the heart of Kentucky. Don't miss your chance to own a slice of the outdoors! *Boundary Lines in photo are not precise.*

9999 Buzzard Rd, Manchester
Colony Rd Unit Lot # 2/ Section C, Manchester
$34,500
26004409 MLS
Building lot ( .9216 acres) available in Liberty Hills Subdivision- Section C/ Lot # 2 Located within couple of miles from Hal Rogers Parkway, hospital, restaurants, shopping, etc.

Colony Rd Unit Lot # 2/ Section C, Manchester
687 H M Garrison Rd Rd, Manchester
$380,000
26017604 MLS

687 H M Garrison Rd Rd, Manchester
213 E Broadway St, Winchester
$200,000
3 Beds ⋅ 1 Baths ⋅ 26027397 MLS

213 E Broadway St, Winchester
107 S Burns Ave, Winchester
$367,700
4 Beds ⋅ 2 Baths ⋅ 26027372 MLS
Timeless character, thoughtful updates, and a walkable downtown location define this distinctive Winchester residence. From the original front door to the beautifully preserved architectural details within, 107 S Burns Avenue reflects the craftsmanship of an earlier era, with original hardwood floors, cherry wood wainscoting, coffered ceilings, custom brick fireplaces and mantels, and original built-ins throughout. Offering four bedrooms and two full baths, the home has been carefully updated while preserving the details that make it unique. The fully renovated upper level provides a private fourth bedroom, full bath, built-in workspace, generous knee-wall storage, and a dedicated heating and cooling system. In the kitchen, custom cabinetry complements an original double-drainboard cast-iron sink, while the main-level bath retains a beautifully reglazed original clawfoot tub. Outdoors, an eight-foot privacy fence creates a secluded backyard setting with an above-ground pool and ample space for relaxing and entertaining. An original carriage-door garage adds another layer of historic character, complemented by off-street parking for up to three vehicles. Located just two blocks from Main Street, the home offers convenient access to downtown Winchester's locally owned restaurants, boutiques, theater, festivals, and community events. College Park and the public library are also just a few blocks away. Beautifully maintained and rich with architectural detail, 107 S Burns Avenue offers an uncommon combination of historic craftsmanship, modern updates, and downtown convenience in the heart of Winchester.

107 S Burns Ave, Winchester
506-513 N Main St, Winchester
$249,900
26027255 MLS
UPDATE: ADDITIONAL PARCEL ADDED. Along with the description below, seller is including 513 N Main which has some buildings in need of repair (thus they were not added to the total square footage). Buy and repair the buildings, or demo the buildings and create additional parking. Has your small business officially outgrown the garage, basement, spare bedroom- or possibly all three? It might be time for a space of its own! This versatile property offers approximately 550 square feet of finished office space plus approximately 1100 square feet of shop/warehouse space. The office area gives you plenty of flexibility for a private office, reception/waiting area, additional workspace or storage, plus one restroom. Out back, the shop/warehouse is ready to work with a gas heater, new LED lighting and two 14' x 14' overhead doors with openers- perfect for vehicles, equipment, inventory or whatever your business needs to keep moving. Most of the work has already been done for you! You'll find fresh paint inside and out, new flooring throughout, and a brand-new blacktop parking lot. Convenient to I-64, Lexington and surrounding Central Kentucky communities, this could be a great fit for a contractor, service-based business or small business owner who simply needs more room to work, store, and grow. Because eventually, your kitchen table would probably like to go back to just being a kitchen table. Listing agent is related to seller.

506-513 N Main St, Winchester
8 Monroe Ave, Winchester
$299,900
3 Beds ⋅ 2 Baths ⋅ 26027106 MLS
Welcome to one of Winchester's best-kept secrets! This beautifully updated 3-bedroom home is truly move-in ready and packed with upgrades inside and out. From the moment you arrive, the beautifully landscaped yard sets the tone for what's waiting inside. Thoughtful updates throughout give the home a fresh, modern feel, while a new roof provides added peace of mind. Step outside and enjoy the large fenced backyard, offering plenty of room for entertaining, pets, play, or relaxing in your own private outdoor space. And it's the little extras that make this home stand out—even the bathroom features Bluetooth connectivity for an added touch of modern convenience! With upgrades around every corner and all the work already done, this is the kind of home you can simply move into and enjoy. Stylish, updated, and full of unexpected extras—this Winchester gem may not stay a secret for long!

8 Monroe Ave, Winchester
330 Spencer Ln, Winchester
$769,900
3 Beds ⋅ 3 Baths ⋅ 26026365 MLS
Beautiful custom home built in 2024 with high-end upgrades throughout. Surrounded by mature trees on over 3 acres with mountain views, this home offers a beautiful mix of privacy, quality, and convenience. From the moment you walk up, you can see the quality of craftsmanship. A large front porch welcomes you with double front doors. Once inside, you're immediately drawn to the soaring ceilings, wood-planked ceiling, wall of black-framed windows, and abundant natural light. The open loft overlooking the great room adds to the unique design and makes the space feel even more impressive. The quality and craftsmanship throughout this home truly stand out and are increasingly hard to find in today's market. You'll find solid wood doors, engineered hardwood floors, custom cabinetry, quartz countertops, designer lighting, and thoughtful details throughout. The primary suite is located on the first floor and features a large walk-in closet and spa-like bathroom. The primary bath includes a beautiful marble tile wet room and freestanding soaking tub, creating a relaxing retreat. The setting is one of the things that makes this property so special. Mature trees surrounding the home give it a peaceful, private feel while still keeping you within an easy drive of Lexington. Outdoor living is just as impressive, with approximately 815 square feet of covered porches, including a screened porch accessible directly from both the primary bedroom and great room. It's the perfect place for morning coffee, quiet evenings, or gatherings with friends. The home is just 1.5 miles from Exit 10 on the Mountain Parkway, approximately 29 minutes from Hamburg Pavilion, 22 minutes from the Red River Gorge, and about 19 minutes from Kroger in Winchester. The oversized 24x30 garage, built in 2026, provides plenty of room for vehicles, storage, a workshop, or recreational equipment. Outside, the 3+ acre lot offers plenty of room to enjoy the property as it is or create your own outdoor space, with room for a future pool and entertaining area. If you've been looking for a newer home with acreage and privacy without feeling too far removed from everything, this is one you'll want to see. If you're tired of seeing the same cookie-cutter homes, this one is refreshingly different. The home has even been selected by Architectural Designs to be featured in a client album on their website.

330 Spencer Ln, Winchester
19 Victory Ave, Winchester
$285,000
3 Beds ⋅ 2 Baths ⋅ 26026938 MLS
Welcome home to 19 Victory Ave in Winchester's! This single-family residence offers 1,780 sq ft of flexible living space, featuring 3 bedrooms, 2 bathrooms, and handsome hardwood flooring. Enjoy cooking and entertaining with the included kitchen appliances, and take advantage of the detached garage and off-street parking. Situated on a spacious lot under half an acre, this property provides convenient access to local Winchester dining, shopping, and everything this city has to offer!

19 Victory Ave, Winchester
326 W Lexington Ave, Winchester
$225,000
3 Beds ⋅ 1 Baths ⋅ 26026771 MLS
ABSOLUTE AUCTION — SELLS TO THE HIGHEST BIDDER REGARDLESS OF PRICE! Offered at Live On-Site Absolute Auction with Simulcast Internet Bidding. Auction is on Thursday, October 15, 2026 at 6:00 PM (EST). Buyers premium will be added to the final bid price and non-refundable earnest money required. Property sells AS-IS, WHERE-IS with no contingencies. 3 Bedrooms, 1 Bathroom with separate dining room, standalone kitchen, and living room featuring a fireplace. Full unfinished basement with ample potential for storage or expansion. Investment Potential: Major DIY/fixer-upper opportunity—ideal for investors or buyers looking to customize and add value

326 W Lexington Ave, Winchester
14 Shelley Dr, Winchester
$215,000
3 Beds ⋅ 1 Baths ⋅ 26026596 MLS
This brick ranch offers three bedrooms, a full bath and luxury vinyl flooring throughout. The spacious living room opens into the kitchen, and the unfinished basement gives you plenty of extra room for storage with space to use however you need it. Sitting on a corner lot, this home is a great option for anyone looking for an affordable home with room to make it their own. Plus, you're close to shopping and restaurants and just a few minutes from I-64 for an easy commute.

14 Shelley Dr, Winchester
600 College St, Winchester
$225,000
3 Beds ⋅ 2 Baths ⋅ 26026485 MLS
Welcome to 600 College Street! Offering over 1,700 square feet, this versatile Winchester home features 3 bedrooms, 2 full bathrooms, plus an additional room ideal for a 4th bedroom, home office, or flex space. Inside, you'll find a spacious living room and a dining room with plenty of room to create additional living or entertaining space. The kitchen offers a walk-in pantry and conveniently located laundry area. An unfinished basement provides ample storage and walkout access, while the attached one-car garage adds everyday convenience. Outside, enjoy a covered front porch and a peaceful back porch surrounded by mature trees for added privacy. Conveniently located near Downtown Winchester, College Park, Legacy Grove, local shopping, dining, and everyday amenities, with easy access to I-64 for a straightforward commute toward Lexington. Improvements, including a roof replacement, LVP flooring, renovated kitchen and baths, and updated plumbing all done in 2024. Schedule your private showing today!

600 College St, Winchester
609 W Barlow Dr, Winchester
$375,000
4 Beds ⋅ 2 Baths ⋅ 26026446 MLS
Welcome to your new home. Move-in ready inside and out, this 4-bedroom, 2-full-bath home offers comfortable living, plenty of finished space, and a backyard that truly feels like your own private retreat! The home has been well cared for and thoughtfully updated, including new flooring throughout the entire finished portion of the basement, new toilets, and a new dishwasher and stove. Step outside and you'll quickly see what makes this property special. The in-ground pool and surrounding outdoor living space are an absolute dream, with extensive improvements completed to make it ready for years of enjoyment. All-new concrete was installed around the pool in 2025, along with a new pool liner and gas pool heater, plus a newer pool pump. A new privacy fence installed in 2023 creates a secluded setting, while the gazebo—complete with electricity—provides the perfect spot to relax, entertain, or spend summer evenings by the pool. The improvements continue with a brand-new back porch completed in May 2026 and a new concrete driveway in 2026, adding even more value and curb appeal. Whether you're entertaining friends around the pool, enjoying a quiet evening under the gazebo, or taking advantage of the additional finished basement space, this home offers a lifestyle that's hard to duplicate. Move in, unpack, and start enjoying it from day one!

609 W Barlow Dr, Winchester
335 Newcastle Ln, Winchester
$304,900
3 Beds ⋅ 3 Baths ⋅ 26026107 MLS
Welcome to this well-maintained home located in a quiet, established neighborhood with convenient access to everything Winchester has to offer. The first floor features an open and inviting layout, creating a comfortable space for everyday living and entertaining alike. Upstairs, you'll find a traditional three-bedroom floor plan with generously sized bedrooms, including a spacious primary suite. Recent updates include a brand-new roof, along with manufactured hardwood flooring installed in the living area, foyer, and primary bedroom. Conveniently located near the Winchester Bypass, this home offers quick access to shopping, dining, and everyday amenities, while also providing easy access to I-64, I-75, Lexington, and the Mountain Parkway for commuters and travelers. Offering a desirable combination of space, updates, and location, this home is ready for its next owner to enjoy. Schedule your private showing today!

335 Newcastle Ln, Winchester
6 French Ave, Winchester
$319,900
4 Beds ⋅ 2 Baths ⋅ 26025571 MLS
SPACE, CHARACTER & LOCATION—THIS HOME HAS IT ALL! Step inside and discover a home filled with charm, character, and plenty of room to make your own. Featuring 4 generously sized bedrooms and 2 bathrooms, this home offers space for everyone to spread out. Beautiful original wood floors throughout the home add warmth and timeless character you just can't recreate. Enjoy the charm of the beautiful front porch, perfect for morning coffee or relaxing at the end of the day. Out back, the privacy-fenced yard provides a wonderful space for entertaining, pets, play, or simply enjoying the outdoors. Add in the convenience of a great location, and this home has so much to offer. Spacious rooms, original character, and a location you'll love—this is one you'll want to see in person!

6 French Ave, Winchester
317 Vanover Way, Winchester
$249,900
3 Beds ⋅ 2 Baths ⋅ 26025070 MLS
Welcome to 317 Vanover Way! This beautiful, well-maintained 3-bedroom, 2-bath home is move-in ready and waiting for its next owner. Step inside to a spacious living room with the bedrooms conveniently located just off the main living area. Coming in from the garage, you'll find a functional mudroom and laundry area that leads directly into the kitchen. Outside, enjoy a nice-sized fenced backyard and a deck that's perfect for entertaining, relaxing, or enjoying time outdoors. A comfortable, well-care-for home with a layout that makes everyday living easy!

317 Vanover Way, Winchester
420 Calmes Blvd, Winchester
$349,900
3 Beds ⋅ 3 Baths ⋅ 26024212 MLS
Location is prime on the west side of Clark county, close to Lexington, schools, shopping and in a well established neighborhood. Pride shows in the care of this 1-1/2 story brick home. Everything you need can be found on the 1st level - master bedroom with a door leading to a hot tub on the back patio. This home has a large living room, with wood floors and fireplace, kitchen with new major appliances that are all staying with home and granite counter tops, and a dining area with door leading to a covered porch. There are 2 more bedrooms and a full bath upstairs. Lots of hardwood and new carpet. Great closet space offering lots of storage!

420 Calmes Blvd, Winchester