Refine Search
Map
Sort by
$205,000
3 Beds ⋅ 3 Baths ⋅ 26019961 MLS
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
$369,000
3 Beds ⋅ 2 Baths ⋅ 26019263 MLS
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
$429,000
3 Beds ⋅ 3 Baths ⋅ 26019133 MLS
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
$209,900
3 Beds ⋅ 1 Baths ⋅ 26019005 MLS
Welcome to this charming newer construction home nestled on a quiet dead-end street in Winchester! Offering 3 bedrooms and 1 full bath, this move-in-ready home features a bright, functional layout with modern finishes throughout. A standout feature is the spacious crawlspace, providing an abundance of storage for seasonal items, tools, or outdoor equipment. Enjoy the peace and privacy of low-traffic living while still being conveniently located near shopping, dining, and local amenities. Whether you're a first-time homebuyer, downsizing, or looking for an investment opportunity, this home is one you won't want to miss!

30 Hughes Ave, Winchester
$789,000
3 Beds ⋅ 2 Baths ⋅ 26018078 MLS
**Drone video and outside pictures available.** Enjoy the space and privacy you've been searching for at 6500 Mount Sterling Rd. Situated on a beautiful rural setting, this property offers the tranquility of country living while remaining conveniently close to Winchester and Lexington. Located less than a minute off exit 101 on I-64. The gorgeous property offers plenty of room for horses, gardening, recreation, or simply taking in the scenic views, this property is ready for you to make it your own! The detached garage has a second floor office area. There are four other outbuildings for horses, hobbies, or equipment storage. Plenty of fenced areas for horses or other farm animals. The gated entrance provide privacy and security. A rare opportunity to enjoy Kentucky living at its best!

6500 Mount Sterling Rd, Winchester
$234,900
3 Beds ⋅ 2 Baths ⋅ 26018492 MLS
*NEW ROOF!* Welcome home to this well-maintained 3-bedroom, 2-bath brick ranch offering easy one-level living in a convenient location close to shopping, dining, parks, and the community pool. The spacious open family room flows into the kitchen, featuring bamboo wood flooring, a large granite island, newer stainless steel appliances, and a gas range—perfect for everyday living and entertaining. Step outside and enjoy your own Aurora above-ground pool, just in time for summer fun! The partially fenced backyard also includes an oversized storage/tool shed, providing plenty of room for hobbies and extra storage. Enjoy peace of mind with major updates, including a newer HVAC system, water heater, Window World windows (approximately 5 years old), and a new roof with a 5-year warranty. As an added bonus, the seller is offering up to a $2,500 flooring allowance with an acceptable offer. Please include the flooring allowance in any written offer. Don't miss the opportunity to make this inviting home yours!

528 Estes Dr, Winchester
$524,900
3 Beds ⋅ 3 Baths ⋅ 26018460 MLS
OK! WOW!!! Location is yes, yes, yes! This house is located in a quiet residential neighborhood and in minutes you can be at the I-64 or I-75 interstate corridors. OK enough about location. This house is pristine! The owners have improved the property with new dimensional style roof shingles in 2025 along with new gutters. They have freshly painted the interior. They have added a new refrigerator, stove, microwave and a washer and dryer. The owners have meticulously maintained this house throughout. From the entrance foyer note the gleaming wood flooring and the fresh paint on the 9' foot ceiling walls, the vaulted great room and the crown molding. The split bedroom concept is great for guests or a home office. And above the garage is a bonus room measuring 420 sq ft. Entertaining or relaxing on the covered back patio that overlooks the beautiful Kentucky Bluegrass is a must. And bonus, the property is adjacent to a church property that is mowed for a walking path. Make an appointment to see this house today, it may be your new home.

275 Runnymeade Dr, Winchester
$235,000
2 Beds ⋅ 2 Baths ⋅ 26018337 MLS
Country living with the convenience of being in the city! This rare find offers over an acre of land inside the Winchester city limits with beautiful views of surrounding farmland. Relax on the spacious partially covered back deck, entertain family and friends, or enjoy plenty of room for gardening, pets, and play. The home features 2 bedrooms, 1.5 baths, and approximately 1,039 square feet of living space on the main level. The finished upstairs adds approximately 385 square feet divided into two bonus rooms currently cooled with a window A/C unit. With the addition of a permanent heat source, this space could easily serve as additional bedrooms, a home office, hobby room, or flex space. Outside you'll find an impressive detached 3-car garage with plenty of room for vehicles, a workshop, or storage, plus a separate storage building for even more space. A remote-controlled gated driveway adds convenience, privacy, and security. If you've been searching for a property that offers the feel of the country while enjoying the convenience of city living, this one checks all the boxes. Potential for second home site! Schedule your private showing today!

47 Hughes Ave, Winchester
$294,900
5 Beds ⋅ 3 Baths ⋅ 26018116 MLS
If you've been looking for an amazing "light" renovation opportunity, this is it! Over 3300 sq ft w tons of character situated on an acre of land w gorgeous mature trees. *Seller's are contributing $5,000 towards buyer's prepaids/closing costs.* Flooring, roof, HVAC heat pumps are under 6 years old. New windows & gutters installed May 2026. Under 5 minutes to 64. Don't let this one pass you by. Come check this property out for yourself!

4603 Paris Rd, Winchester
$147,900
3 Beds ⋅ 1 Baths ⋅ 26017859 MLS
Charming and move-in ready! This freshly renovated 3-bedroom, 1-bath home in downtown Winchester offers all-new flooring and fresh paint throughout. The spacious eat-in kitchen provides plenty of room for gathering, and the in-unit washer/dryer hookup adds everyday convenience. Situated on a quiet street directly across from a park and within walking distance of the elementary school, this home offers a peaceful, family-friendly location. Enjoy the fully fenced backyard and central heat and air for year-round comfort. Ready for immediate occupancy! schedule your private tour today!

118 Park Ave, Winchester
$749,900
3 Beds ⋅ 3 Baths ⋅ 26017698 MLS
Welcome to peaceful country living on 7.14 beautiful acres in Winchester! Built in 2022, this custom one-level home offers 3 bedrooms, 2.5 bathrooms, and 2,735 square feet of thoughtfully designed living space. The open floor plan features hardwood flooring, a spacious great room with a gas fireplace, and a stylish kitchen with a large island and ample cabinetry. The split-bedroom layout provides privacy, while the primary suite offers a spa-like bath and walk-in closet. Enjoy scenic views from the covered porch and the convenience of an attached two-car garage, all while being just a short drive to Winchester, Paris, and Lexington. This is the perfect blend of modern comfort and peaceful country living. Schedule your showing today!

2180 Big Stoner Rd, Winchester
$350,000
4 Beds ⋅ 3 Baths ⋅ 26017601 MLS
Professional Pictures coming 7/11. Welcome home to this spacious corner-lot property in a highly desirable neighborhood! Designed with family living in mind, this home features two distinct living spaces, perfect for a formal living room and a separate kids' playroom or cozy den. Everyone gets their own space with four generous bedrooms, offering plenty of room for sleep, study, and storage. Enjoy quiet mornings or bug-free evenings on the screened-in porch, which overlooks a nice-sized yard with endless room for kids and pets to play. Don't miss this perfect blend of space, comfort, and functionality for your family! *Buyer to verify all aspects of the listing.

411 Skylark Dr, Winchester
$699,000
4 Beds ⋅ 4 Baths ⋅ 26017283 MLS
Sellers will be reviewing offers this evening, Sunday, July 12, 2026 PM Rare Opportunity! Offered for the first time in nearly 50 years, this one-of-a-kind property presents endless possibilities in a breathtaking setting. Nestled on just over 8 private, serene acres with stunning views of Boone Creek, this spacious home offers the perfect blend of privacy, natural beauty, and room to grow. This exceptional property offers a true experience with nature, where peace and tranquility create the perfect private retreat. Conveniently located just minutes from shopping, restaurants, and everyday amenities in Hamburg plus easy access to Hospitals, you'll enjoy the rare combination of secluded country living with the convenience of city access. Inside, you'll find 4 generously sized bedrooms, 3 full baths, and a half bath, along with a welcoming great room designed to showcase the incredible creek views. A large spacious kitchen with a center island with bar space seating and a breakfast area overlooking the pool. The large laundry room and versatile bonus room provide additional space that's perfect for a home office, hobby room, or flex space to fit your lifestyle. The second level offers 2 spacious bedrooms that share access to a full bath, incredible storage options, including a huge walk-in closet and an expansive floored attic area perfect for seasonal items, hobbies, or keeping everything organized. Step outside to enjoy the inground pool, complete with a brand-new liner scheduled for installation on July 20, making it ready for seasons of outdoor entertaining and relaxation. Whether you're looking to update, personalize, or simply enjoy this exceptional property as it is, opportunities like this are truly rare. Don't miss your chance to own a private retreat with spectacular Boone Creek views and unlimited potential. Here is your chance to personalize and make it your own. Home needs a little TLC! This home is in Clark County with a Lexington/Fayette County address. Sellers considered remodeling the home a few years back please see attached documents to view the floor plan that they considered. Check out the Zillow Link https://www.zillow.com/homedetails/5349-Athens-Boonesboro-Rd-Lexington-KY-40509/115282711_zpid/?view=public

5349 Athens Boonesboro Rd, Lexington
$274,900
4 Beds ⋅ 3 Baths ⋅ 26016975 MLS
Welcome to 304 Sandra Drive. This 4 bedroom, 2 bath ranch is quietly nestled within the desirable Westmeade subdivision. While location is obvious, this property features many updates that can be seen throughout. Multiple primary bedroom with on-suites, large backyard, new HVAC and water heater, including duct work, and so much more. Schedule your showing today!

304 Sandra Dr, Winchester
$350,000
1 Beds ⋅ 1 Baths ⋅ 26016768 MLS
Welcome to your private slice of Kentucky countryside - offering the perfect blend of modern comfort, functional farm amenities, and convenient access to everything you need. Located just under 13 minutes from downtown Winchester and 35 minutes from Hamburg in Lexington, as well as only 18 minutes from I-64 and 22 minutes from I-75, this unique property is ideal for horse owners, hobby farmers, homesteaders, or anyone looking for peaceful rural living without sacrificing convenience. The beautifully maintained 800 square foot home features 1 bedroom, 1 bathroom, plus a versatile loft space perfect for a guest bedroom, home office, or flex room. Inside, you'll find fresh paint throughout every room, durable porcelain tile flooring throughout the entire home, and thoughtful updates that make this property move-in ready. Enjoy relaxing mornings and evenings on both the front and back porches, all while staying connected with high-speed Spectrum Fiber internet availability. For those needing workspace, storage, or equestrian facilities, the property truly stands out. The impressive 30x36 barn includes three fully rubber-matted 10x12 horse stalls, a 12x36 attached extension for hay and equipment storage, water service, its own dedicated 200-amp electrical service with 40 available spaces. Animal lovers will appreciate the thoughtfully designed acreage and infrastructure. One ½-acre fenced pasture meets BLM Wild Horse and Burro adoption requirements, featuring no-climb fencing with top board perimeter fencing and a large run-in shelter, and has also been successfully used for goats. The main 3-acre pasture offers additional room for horses or livestock and includes its own large run-in shed with electric and water service already installed. The property is also ready for small livestock and homesteading with an 8x8 chicken coop featuring a brand-new floor, roosting bars, and an attached 10x16 covered run, fully enclosed using predator-proof hardware cloth. The entire property boundary is fenced, and all existing gates convey with the property. This home has been meticulously maintained with major recent upgrades, including: New ridge cap installed in 2025 Indoor HVAC evaporator coils replaced September 2025 Outdoor HVAC valves, piping, and dryer replaced in 2026, Spray foam insulated attic for improved efficiency The home also includes the dishwasher, refrigerator, and microwave, and stove along with a built-in office desk located in the loft. An additional advantage is the property's future potential -- the septic system is positioned toward the rear of the property, allowing approximately 1 acre of front yard space for future home expansion, shop construction, or additional building opportunities. Whether you're looking for a move-in ready mini farm, horse property, homestead setup, or simply a peaceful property with room to grow, this one offers a rare combination of functionality, upgrades, and flexibility.

6888 Bybee Rd, Winchester
$409,500
3 Beds ⋅ 2 Baths ⋅ 26016762 MLS
215 Delaplain Road is the kind of home where pride of ownership is easy to see. Inside, you'll find 3.25-inch hand-scraped hardwood flooring throughout, travertine tile in both bathrooms, updated vanities, newer light fixtures, and a beautifully tiled walk-in shower with a custom glass door in the primary bath. The kitchen offers added cabinetry/wet bar space, a newer refrigerator, and a gas line already in place if you'd like to convert the stove to gas. One of the best features of the home is the custom 4-seasons sunroom, complete with Eze-Breeze four-track windows, ceramic tile flooring, recessed lighting, a tray ceiling, a ceiling fan, and a cabana door overlooking the backyard. The lot is a true highlight, with outdoor lighting, low-maintenance landscape rock, a concrete walkway, and a shop/outbuilding that stays with the property. Major system ages include the roof, replaced in 2018, and the HVAC, installed in 2017. Additional updates include replacement windows throughout, a custom front door, a double garage door with an opener and keypad entry, gas logs, and updated laundry room cabinetry with pull-out shelving. Thoughtfully cared for and improved over the years, this home offers comfortable everyday living with spaces you'll enjoy in every season.

215 Delaplain Rd, Winchester
$365,900
3 Beds ⋅ 2 Baths ⋅ 24018286 MLS
New Construction, come view, great house plan, ranch on a crawl space, 3 bedrooms, 2 bath, you will love this inviting neighborhood, plan shown on line could vary, this is a spec home, all the colors have been decided, fixtures, flooring, brick, siding, cabinets, countertops have been ordered, restrictions apply, no HOA, buyer to verify sq ft of home and lot. This home is close to I-64, I-75, Lexington, Richmond, shopping, churches, hospital and schools, pictures to follow as home is being constructed.

206 Jett Dr, Winchester
$124,500
2 Beds ⋅ 1 Baths ⋅ 26000228 MLS
Investment Opportunity or Perfect Starter Home This charming 2-bedroom, 1-bath property is full of potential! With a strong rental history and an excellent lease track record, it's ideal for investors or first-time buyers. The home requires only light maintenance, and the seller is even willing to fund minor repairs. Don't miss your chance to own a property with great value and endless possibilities! Property is AS IS! Bring me a offer.

122 Callaway Street Se Callaway Street, Winchester
$265,000
3 Beds ⋅ 1 Baths ⋅ 26012905 MLS
Come Home to Sunset!!!! Brick Ranch home, with 2 driveways, 3 bedrooms, 1 bathroom, Open Living Room, Dining Room and Kitchen Area, Spacious Laundry Room, Covered back patio for outdoor living! Beautiful Hardwood floors, updated bathroom and kitchen, exceptional location, building out back for he shed or she shed or storage, move in and enjoy the sunset!

119 Sunset Hts, Winchester
$165,000
4 Beds ⋅ 3 Baths ⋅ 26008701 MLS
Investor special with historic charm on corner lot! Opportunity awaits with this spacious 5 bedroom, 3 full bath home offering 3,462 sq ft of potential. Situated on a corner lot and walkable to downtown, this classic 2 story property is rich in character, featuring original hardwood floors, detailed woodwork, a welcoming front porch with columns, and a striking staircase with stained glass accents. The home has been partially gutted, with the kitchen, bathrooms, and several rooms ready for renovation, making it an ideal project for investors, flippers, or buyers looking to customize their dream home. With solid bones and timeless architectural details throughout, this property is primed to be transformed into a true showpiece. Cash or renovation financing required. Inspections welcome but selling AS-IS. Bring your vision and unlock the full potential of this one of a kind property.

229 S Highland St, Winchester
$235,000
4 Beds ⋅ 1 Baths ⋅ 26013563 MLS
Nestled in a well-established neighborhood filled with charm and character, this inviting all-brick home offers the warmth and comfort you've been looking for. Featuring 4 bedrooms and 1 bath, the thoughtfully designed layout includes a primary bedroom and second bedroom on the main floor, with two additional bedrooms upstairs, providing flexibility for family, guests, or a home office. Beautiful hardwood floors add timeless character throughout much of the home, while the kitchen is equipped with stainless steel appliances and plenty of space for preparing meals and gathering with loved ones. The solar panels help keep utility costs low, making this home as efficient as it is welcoming. Outside, you'll find a wonderful fenced backyard that feels like a private retreat, complete with a chicken coop, storage shed, and plenty of room for gardening, pets, play, or relaxing evenings outdoors. A 1-car garage provides additional storage and convenience. With its classic all-brick construction, cozy atmosphere, mature surroundings, and practical updates, this home offers a perfect blend of comfort, character, and everyday living in one of Winchester's quaint established neighborhoods.

120 Windsor Dr, Winchester
$549,900
3 Beds ⋅ 2 Baths ⋅ 26010352 MLS
Nearly new French country ranch that has been gently lived in. This classy home has magnificent curb appeal. When you walk through the front door you are welcomed by a tasteful foyer area. Stroll into the wide-open space of the great room with a towering, coffered ceiling and tons of natural light. The gas fireplace adds a nice focal point to the living space. The kitchen space is equipped with all stainless appliances including a gas range for cooking those delicious meals. The large kitchen overlooking the great room offers the convenience of an eat in bar area, delightful dining space, a huge hidden pantry and a unique kitchen niche to make it your own unique space for a possible coffee bar. This home is all about convenience and privacy with the split bedroom concept. Lots of space in the primary bedroom for your king size bed plus a nice sitting area. You will love the huge primary bath with stylish custom tile and the adjoining generous sized closet for the fashionista. In edition there are two guest bedrooms with a full bathroom. There is an additional flex room that makes a great office space or a 4th bedroom. The large laundry area and drop zone is an added convenient feature to the home. From enjoying your morning coffee, evening relaxation or outdoor gatherings the large covered back patio is the place to be with the outdoor fireplace. You will love the large 2-car oversized garage. This home has so much to offer! Convenient to local shopping, restaurants, I64, 17 miles to Man o' War Blvd Lexington and 28 miles to Bluegrass Airport. Schedule your tour today to check out this beautiful home. Now is your chance to own this nearly new home.

108 Bella Shae Way, 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
$249,900
3 Beds ⋅ 1 Baths ⋅ 26016217 MLS
Welcome to 10 Chickadee Lane, Winchester, KY—a beautifully updated 3-bedroom, 1-bath ranch offering the perfect combination of modern upgrades, timeless character, and an unbeatable location. If you're searching for a move-in ready home in Winchester, Kentucky, this one deserves a spot at the top of your list. Extensively renovated in 2020, this home provides peace of mind with major improvements already completed, including new windows, exterior doors, roof, gutters, updated lighting, kitchen cabinetry, countertops, upgraded appliances, remodeled bathroom, electrical panel, HVAC system, water heater, and beautifully refinished hardwood floors. Every update was thoughtfully completed to create a home that is both stylish and functional. Since the renovation, the property has continued to improve with the addition of an 8' x 12' storage shed, a privacy fence enclosing the entire backyard, and additional measures taken to help maintain a dry crawlspace, reflecting the pride of ownership and ongoing maintenance throughout. Inside, you'll appreciate the warmth of the refinished hardwood floors, an updated kitchen designed for everyday living, and a bright, comfortable layout that makes this home feel welcoming from the moment you walk in. Outside, the fully fenced backyard provides plenty of space for entertaining, gardening, pets, or simply relaxing in your own private outdoor retreat. Conveniently located in an established neighborhood, 10 Chickadee Lane offers quick access to shopping, dining, schools, parks, and everything Winchester has to offer, while also providing an easy commute to Lexington and surrounding Central Kentucky communities. Natural gas is available at the property; however, the gas line is currently capped and no active meter is installed. Don't miss this opportunity to own a thoughtfully updated ranch home where the major improvements have already been completed for you. Schedule your private showing today! Buyer to verify all aspects of the property, including schools, square footage, utilities, and any information important to the purchase.

10 Chickadee Ln, Winchester
$360,000
1 Beds ⋅ 2 Baths ⋅ 26012322 MLS
Home listed as one bedroom while unofficially has 3 but 2 of them are interior rooms without windows. ( Owners Now Offering to pay up to $5,000 in closing cost and pre-paids on behalf of buyers). Tired of the honking horns , congested traffic, sirens of town living and dreaming of country living, your own slice of paradise? Maybe raising your own garden , owning chickens , goats, horses , whatever you always dreamed of. Maybe just kicking back on the wrap around porch watching the chickens peck. This really is an amazing property and you will fall in love with all the bells and whistles like the beautiful soaking tub, 2 walk in showers, huge kitchen island, large primary bedroom and bath, stainless steel appliances. It practically a new house , the front portion of the house where the living room , hall, primary bedroom were all built new in 2020 . All the wiring , plumbing , insulation, flooring , drywall has been replaced since 2020. Home is also very conveniently placed just minutes from exit 10 on the Mountain Parkway between, Winchester and Clay City. Dont let anyone beat you to it , this is a real jewel. Porch swing belonged to owners great grandmother and does not convey.

3359 Trapp-Goffs Corner Rd, Winchester
$785,000
4 Beds ⋅ 3 Baths ⋅ 26012036 MLS
This beautiful home sits on over 7 acres of peaceful countryside. Bring your horse! The back portion of the land is completely fenced. The private outdoor space includes a huge deck with a lovely view and an inviting covered front porch. The backyard would make the perfect space for your own dream swimming pool. Since the property has a 3-car detached garage; a 2-car attached garage plus a 1275 square feet equipment building there is plenty of space for all of your outdoor toys. The detached garage has water and electrical service with a workshop area and also a large unfinished loft area for additional storage or possibly create the space into a recreation space. The lovely custom home with over 3300 square feet has hardwood flooring throughout, crown molding, tall ceilings, and built in shelving in the family room. Lots of natural light in the living area with the sunburst arched windows overlooking the property. The home has a convenient split bedroom concept. The spacious primary bedroom has an ensuite bath with a soaking tub and separate vanities and a large closet. The upstairs has an additional full bathroom with 2 large flex rooms with one currently being used as a 4th bedroom. The additional flex room would be a great space for a workout room or office. This well-maintained country home offers the convenience of Winchester shopping and dining and also only 8 miles to I64 and I75. If you have been looking for a home with a quiet country setting this is the perfect property.

7300 Old Boonesboro Rd, Winchester
$264,900
4 Beds ⋅ 1 Baths ⋅ 26012319 MLS
Could 162 French Ave., Winchester, KY 40391 be your new address? This stunning, updated Craftsman home feels like it was pulled straight from the pages of Southern Living Magazine, blending modern updates with timeless character and charm. Recent improvements including new windows, doors, wiring, and fresh landscaping enhance the home while preserving its original appeal. This move-in ready property offers 4 bedrooms, an updated bathroom, a welcoming living room with a decorative (non-working) fireplace, and a cozy den featuring preserved French doors. The foyer leads to a beautifully painted staircase and second floor, while the spacious dining room and kitchen showcase custom painted cabinetry, stainless steel appliances, and a pantry. A large laundry room doubles as a walk-in closet for added convenience. Enjoy relaxing mornings on the wrap-around front porch with brick accents and composite steps, or unwind on the rear sunporch overlooking a vinyl-fenced yard complete with a patio area perfect for a fire pit and a 10X17 shed. The main bedroom is located on the first floor, with three additional bedrooms and a bonus room upstairs. Thoughtful touches like modern fixtures, fresh paint, exquisite wallpaper, and newly painted wood flooring elevate the entire home. With large rear parking and a prime location in the heart of downtown Winchester, you'll be within walking distance to local shops, dining, and upcoming festivals. The current owner will surely miss the convenience and wonderful neighbors and is confident the next owners will fall in love just as deeply. This is one you have to see! ONE year home warranty to buyer at closing for peace of mind and dishwasher allowance!

162 French Ave, Winchester
$1,149,000
3 Beds ⋅ 4 Baths ⋅ 25018600 MLS
Seller will need 48 Hours to show, This log cabin is located on gently rolling 28 acres very few miles from town, you will think you are on vacation in the sparking pool, tastefully landscaped, fireplace in the great room which leads into a in law quarters, large kitchen that has been wonderfully remodeled with extensive detail, master suite is located on first floor, mud room, 3 1/2 baths, loft/bedroom/full bath upstairs, separate very large kennel, puppy paradise, office, has all the upgrades for shelter & housing, grooming, dog run, this home is must see, call today! Selling ''AS IS'', inspections welcome, 48 hours notice to show this property is 30 minutes to Lexington and close to I-64 , Please do not pet dogs,

2100 Irvine Rd Unit 40391, Winchester
$199,000
2 Beds ⋅ 2 Baths ⋅ 26012179 MLS
You don't want to miss this desirable two primary bedroom home with 2 full bathrooms and large walk-in closets!! There is a gorgeous gas fireplace situated as the focal point of the main living space and an attached one car garage.

104 Bay Hill Dr, Winchester
$484,900
4 Beds ⋅ 3 Baths ⋅ 26011136 MLS
Step into a lifestyle where modern luxury and brand-new construction come together seamlessly. This home is perfectly positioned with golf course views and unforgettable sunset skies, this newly built home offers the kind of setting that turns ordinary evenings into your favorite part of the day—without sacrificing style, comfort, or convenience. Inside, soaring vaulted ceilings and a warm fireplace create an inviting centerpiece for the open-concept living space—designed for both effortless entertaining and cozy nights at home. The timeless kitchen is equal parts beautiful and functional, featuring quartz countertops, a spacious walk-in pantry, and a dedicated coffee bar nook ready to elevate your morning routine. Just beyond, a dedicated dining area creates the perfect backdrop for weeknight dinners, holiday gatherings, and lingering conversations with family and friends. The primary suite feels like a private retreat, offering a spa-inspired en-suite complete with a soaking tub, tiled walk-in shower, dual vanities, and an expansive custom closet designed with luxury in mind. A split-bedroom floor plan provides ideal privacy with three additional bedrooms and two full bathrooms, creating flexibility for guests, family, or a home office setup. Outdoor living provides a screened back patio made for slow mornings, relaxing evenings, and enjoying the peaceful views. Whether you're gardening, unwinding after a long day, or gathering on the front porch with friends as the sun sets over the golf course, this space was designed to be enjoyed. And the location? Exceptional. Nestled just minutes from charming downtown Winchester's local shops, restaurants, and small-town charm, with quick access to I-64 for an easy commute. Plus, the oversized tall garage offers incredible vertical storage opportunities for hobbies, equipment, and all of life's extras. A rare opportunity to enjoy the ease of new construction, elevated design, and a lifestyle centered around comfort, connection, and beautiful surroundings. This isn't just a home—it's your next chapter.

414 Fairholme Way, Winchester