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175 Chatham Pl, Winchester
$4,900,000
2 Beds ⋅ 3 Baths ⋅ 25012023 MLS
36 Townhomes ,located behind Lowes,Winchester,Ky.Great rental property, owner will do some owner financing

175 Chatham Pl, Winchester
2090 Pretty Run Rd, Winchester
$4,880,000
23019893 MLS
Excellent farm and investment opportunity to own one of the largest tracts of land for sale in the area. about 4 miles from Winchester and I-64., 20 mi. from Lexington. This 610 +- acres is an outstanding grain and cattle farm with productive soils consisting of lowell-Sandview and Salvisa, McAfee and Maury silt loam with over 500+ acres of cropland with 100+ acres of fenced pasture land. It is well suited for crops and livestock, horses and development. 5 entrances and road frontage on Pretty Run and Gay Evans Road. This is a heritage farm with great potential. The farm can be divided. Farm is currently under annual lease expiring April 1, 2024

2090 Pretty Run Rd, Winchester
599 Blt Way, Winchester
$1,460,000
26012007 MLS
**Click on the Virtual Tour section to see the video walk through!** Prime 20,252 SQFT Industrial Facility -- Exceptional Location & Turnkey Ready This well-maintained 20,000 sqft industrial warehouse offers the ideal combination of location, functionality, and flexibility. Built in 2004, the metal building features a clean, open span layout designed to accommodate a wide range of industrial, storage, logistics, or manufacturing uses. Strategically positioned 1 minute from I-64, 5 minutes from the Mountain Parkway, and 15 minutes from I-75, this property delivers unmatched regional connectivity and fast access across Central and Eastern Kentucky. Inside, the warehouse includes 2 offices, 2 bathrooms, and a break room (approx. 150 sqft total), with the remaining space wide-open for maximum operational efficiency. Loading and distribution are made easy with 2 dock-height doors and 5 drive-in automatic bay doors, offering excellent flow for semi-trucks, box trucks, and fleet operations. A top-of-the-line industrial racking system--valued at over $40,000--has been professionally installed and will convey with the sale. 16' Tall Racks with 8' between uprights, this system is purchased from Toyota Handling Systems and the racks are bolted to the concrete slab. It may be removed or rearranged to meet the buyer's needs, making this a rare turnkey opportunity for businesses requiring optimized warehouse organization. With its incredible highway access, versatile layout, and significant included infrastructure, this property is perfectly suited for logistics operations, distribution, storage, trades, manufacturing, or an expanding local business seeking high-quality industrial space.

599 Blt Way, Winchester
273 Shoppers Dr, Winchester
$1,400,000
25505288 MLS
10,136 sf of office space, originally constructed as Palmer Engineering headquarters and occupied by the Clark County Health Department since 2003. Building is currently set-up for one occupant with offices, conference areas, and flex space but could be converted into multiple units. There is a 1,754 sf metal pole barn with electricity and paved floor.

273 Shoppers Dr, Winchester
1200 Craig Xing, Winchester
$1,370,000
4 Beds ⋅ 5 Baths ⋅ 26013734 MLS
Discover elevated living on 2.5 acres! This 3,350 sqft custom masterpiece boasts 4 bedrooms, 4.5 bathrooms with an open 2,670 sqft main level. Featuring custom solid oak cabinetry not only in kitchen, but master closets, pantry and utility areas. Custom Showers and tile in each bathroom throughout the home. Gas and electric fireplaces located in great room as well as primary first floor bedroom. Head upstairs to the spacious 680sqft recreation room with its own full bathroom and attic storage access. Step outside to your large, spacious covered patio, personal inground pool with spa and sunken inground fire pit for endless entertaining. 3-Car garage offers ample storage. The 2670sqft Walk-out basement is a blank canvas with endless opportunities. Basement can be finished by builder at buyer's discretion. Some additional selections may be available. LUXURY, SPACE and PRIVACY just minutes from town.

1200 Craig Xing, Winchester
6237 Bybee Rd, Winchester
$1,075,000
5 Beds ⋅ 7 Baths ⋅ 25012707 MLS
Step into timeless elegance with this breathtaking modern Victorian-style masterpiece, perfectly positioned on 4.39 acres with panoramic views of sunrises, sunsets, and distant mountains. Designed and built by Tom Padgett, this home is rich in character and detail—from hand-hewn wood beam ceilings to Waterford crystal chandeliers. The grand 2-story foyer welcomes you into a flowing layout that includes a first-floor primary suite with a fireplace, sitting area, and private wrap-around porch. The gourmet kitchen connects to a butler's pantry, prep area, breakfast room, and formal dining room, ideal for entertaining. Upstairs offers two more primary suites, 2 more spacious bedrooms, and a private study/office with a fireplace. An elevator provides easy access to all three levels. The finished walkout lower level includes an in-ground pool, outdoor bar, private bath, movie room, rec space, and 1100+ sq ft of storage. Custom moldings, built-ins, hand painted Kohler sinks and hardwood floors throughout—this is luxury living at its finest! Other notable features include a 3 car garage, finished storage space above the garage & unfinished storage in the basement.

6237 Bybee Rd, Winchester
3760 Old Boonesboro Rd, Winchester
$1,050,000
5 Beds ⋅ 5 Baths ⋅ 26006697 MLS
Step through the striking red front doors and into a home where craftsmanship, character, and comfort come together. This beautifully maintained property sits on nearly 13 acres at the edge of Winchester, offering a peaceful retreat with the charm of a mid century floorplan and rich woodwork, tile, and hardwood floors throughout. The spacious kitchen and all three full baths feature high end finishes, and the home offers multiple unique spaces for relaxing or entertaining. From the second floor, enjoy your own private balcony overlooking the expansive backyard and in ground pool. On the main level, a covered porch provides easy access to the pool area, along with a convenient exterior door leading directly to a small bathroom—perfect for swimmers. The basement is also a cozy retreat including a living area with a stone fireplace and a bar, another full bed and bathroom, plus a bonus space that could be used as an exercise room or a creative space. Recent updates include new tile and hardwood flooring and fresh interior paint. Outside, the fully fenced yard is beautifully landscaped with mature trees and manicured lawn. This property also includes a separate garage ideal for hobbyists, a storage building with a screened room suitable for chickens or small animals, and a full 2,000 sq ft barn—offering endless possibilities for country living.

3760 Old Boonesboro Rd, Winchester
7210 Ecton Rd, Winchester
$907,000
5 Beds ⋅ 5 Baths ⋅ 26005207 MLS
Welcome to 7210 Ecton Road a stunning 5 bedroom, 4.5 bathroom home situated on 7+/- acres (awaiting final survey) of gently rolling Kentucky countryside. This property offers the perfect balance of modern comfort, privacy, and wide-open space, just minutes from downtown Winchester. Step inside to discover a spacious and well-designed floor plan featuring: 5 generously sized bedrooms including a private primary suite with en-suite bath, 4 full bathrooms thoughtfully placed throughout the home for convenience and comfort and 1 half bathroom located on the back porch for convenience when spending time outside or at the pool. Bright, open living spaces ideal for both everyday living and entertaining, A large kitchen with ample cabinetry, prep space, large island that allows seating for 4 as well as a dinning area, A fully finished basement perfect for a second living area, rec room, home office, or guest quarters, Attached garage and additional storage options Covered porches and outdoor spaces to take in the peaceful surroundings. The 7 +/- acres offer endless possibilities whether you're envisioning a hobby farm, horse property, or simply space to roam and relax, this land is ready for your vision.

7210 Ecton Rd, Winchester
1114 Mccann Dr, Winchester
$900,000
25010707 MLS
This well built medical office is excellent for an owner user or as a potential investment property. There are 7 exam rooms, 2 large labs, a break room and other offices. There is a fully finished attic area that is perfect for storage and could be expanded. Located just off of the highly-traveled Lexington Avenue, it's an approximate 6 minute drive from I-64 and Clark Regional Medical Center. This property is also well situated next to Winchester's largest park, Legacy Grove, which boasts a well appointed play area and a large running/walking trail that sits on over 30 acres. There are numerous other businesses in the immediate vicinity. Property Highlights: -This 5,126 SF medical office building serves as an opportunity for an owner to occupy the space or as an investment property. -The site offers ample parking for employees and patients alike. -Well-designed medical building.

1114 Mccann Dr, Winchester
700 Nick Ln, Winchester
$880,000
3 Beds ⋅ 3 Baths ⋅ 25013735 MLS
🚨 BIG PRICE DROP ALERT! 🚨 Motivated sellers are ready to make a deal—this is your chance to snag an unbeatable offer! 💰🏡Step into country living with this amazing 120-acre working farm! You'll love the brand-new 3-bedroom, 2.5-bath home that features an open floor plan, perfect for hanging out with family or hosting friends. It's got all the modern touches, so you can enjoy both style and comfort. This farm is ready to work with a brand-new 2,000 sqft metal pole barn—plenty of space for storage, projects, or hobbies. There's also a classic 10-bent barn at the back of the property, adding some old-school charm and functionality. With city water running throughout the farm, everything is super convenient. Whether you're looking to start a farm, expand your operations, or just enjoy wide-open spaces and fresh air, this property checks all the boxes. It's the perfect mix of practical and peaceful country living.

700 Nick Ln, Winchester
4755 Combs Ferry Rd, Winchester
$850,000
3 Beds ⋅ 3 Baths ⋅ 26001454 MLS
Welcome to Windswept Farm located on a most desirable piece of Kentucky Bluegrass. Located approximately 15 minutes from Hamburg, Lexington, you can also be in Richmond in about the same amount of time and Historic Downtown Winchester. This property has been meticulously maintained, from the ranch style house with an awesome 2 car garage with storage, a detached heated 3 car garage and an inground heated pool. And there is a 3 stall horse barn with automatic watering in the paddock area. The owners pride shows throughout the home. When you step in the front door you immediately see the beautiful view of the pool and the rolling Kentucky Bluegrass. The gleaming hardwood floors are another distraction but come on and see the great room with the wood burning fireplace for those cozy times. The dining room and the eat in kitchen provide space for entertaining family and friends. The covered rear patio also provides that entertaining space and bonus when the heated inground pool is open. And bonus for that pool party there accessibility to an interior half bath. The primary bedroom has a woodburning fireplace and 2 walk in closets. The property also features a privacy gate a the front entrance to the driveway. Lots to love about this property, make your appointment today.

4755 Combs Ferry Rd, Winchester
2447 Clintonville Rd, Winchester
$850,000
5 Beds ⋅ 4 Baths ⋅ 25003433 MLS
What a great opportunity to own 3 acres just 15 minutes from Man O War and 20 minutes to the Hamburg Shopping Area. The move in ready property features a beautiful brick home built by builder, Michael Childers, to use as his main residence. The property also has a 3 car detached Garage which is deep enough to hold 6 cars and one door is tall for storage of a Recreational Vehicle. It has been beautifully updated with gleaming, newly refinished hardwood floors, tall ceilings and lavish woodwork. The two story Entry is flanked by a formal Dining Room with a double tray ceiling. The spacious Kitchen has cream cabinetry with pull out shelving in many cabinets, granite countertops and a large island for bar stools. Stainless appliances complete this chef's Kitchen which opens to a Breakfast Area with door to a deck overlooking the adjacent farm. The huge Great Room features a vaulted ceiling, lovely carved mantle fireplace and entertainment center which will remain with the house. There are two Bedrooms on the main level & 2nd Floor with remodeled full Bathrooms. The second floor has a spacious Primary Suite with vaulted ceiling.. The Primary Bath offers beautiful cabinetry with double sinks and an amazing marble shower. The finished, walkout Basement features a Theatre Room, Rec Room, full Bath, large storage closet and 2 car Garage.

2447 Clintonville Rd, Winchester
200 Old Log Lick Rd, Winchester
$850,000
3 Beds ⋅ 2 Baths ⋅ 26019577 MLS
Behind a private, gated entrance on 14.38 acres, this 3,481 sq ft all-wood cabin estate is a truly rare find in Central Kentucky. Offering 3 bedrooms, 2 bathrooms, and a flexible bonus room perfect as a 4th bedroom or home office, every inch of this home reflects true craftsmanship -- rich wood features throughout, a large sunroom, and a screened-in back porch made for long evenings and unhurried mornings. The newly remodeled kitchen features all-new appliances and is ready for full-time living or weekend retreats. Outside, enjoy an in-ground pool with concrete decking, a stocked pond, a seasonal stream along the boundary, RV pad with full electric and water hookup, a 4-stall metal barn, 2-bay garage under the home, and a 3-bay detached garage. 14.38 private acres with room to breathe, grow, and put down roots. Located just ~15 minutes from Downtown Winchester, ~25 minutes from Lexington, and under 30 minutes from Red River Gorge. Fox General Store is located less than a mile away. Private showings by appointment only.

200 Old Log Lick Rd, Winchester
7075 Ecton Rd, Winchester
$847,000
26001880 MLS
ABSOLUTE AUCTION — SELLS TO THE HIGHEST BIDDER REGARDLESS OF PRICE! Offered at Live On-Site Absolute Auction with Simulcast Internet Bidding, this exceptional 83.714± acre Clark County farm will sell on Saturday, March 7, 2026 at 10:30 AM (EST) at 7075 Ecton Rd, Winchester, KY 40391. Tract One: 36.825Acres, Tract Two: 5.196 Acres, Tract Three: 5.022 Acres Tract Four: 36.671 Acres The property will be offered in 4 individual tracts and may be purchased separately, in combinations, or as a whole, providing outstanding flexibility for farmers, builders, investors, or recreational buyers. Featuring gently rolling topography, quality soils, open cropland, pasture, and wooded areas, this property is well-suited for row crops, livestock, hunting, future home sites, or long-term investment. Located in a highly desirable area of Clark County with easy access to Winchester and surrounding markets. Property Previews: Sunday, March 1, 2026 | 2:00-4:00 PM Thursday, March 5, 2026 | 2:00-4:00 PM Private showings available by appointment. Buyers premium will be added to the final bid price and non-refundable earnest money required. Closing on or before April 22, 2026. Property sells AS-IS, WHERE-IS with no contingencies. Do not miss this rare opportunity to buy prime Kentucky land at Absolute Auction. See terms and conditions for more details.

7075 Ecton Rd, Winchester
2395 Becknerville Rd, Winchester
$830,000
4 Beds ⋅ 4 Baths ⋅ 26000132 MLS
An exceptional offering of refined country living, this stunning 11-acre estate blends privacy, elegance, and convenience—just 15 minutes to ever growing Hamburg Shopping Center! And just six miles to downtown Winchester! Thoughtfully updated throughout, this beautifully appointed ranch-style residence delivers timeless design and modern luxury at every turn. The light-filled, open floor plan showcases all new flooring, fresh designer paint, and extensive upgrades throughout the home. At the heart of the home, the gourmet kitchen is both striking and functional, featuring an expansive statement island, stone countertops, custom cabinetry, double ovens, and a gas cooktop—ideal for both elevated entertaining and everyday living. A butler's pantry and laundry room provide additional prep space and storage. The great room exudes warmth and sophistication with rich hardwood flooring, a gas fireplace, and custom built-ins. The primary suite is a true retreat, offering a spa-inspired bath with a soaking tub, an impressive tiled shower, and a generous walk-in closet. Two additional guest suites share a beautifully designed Jack-and-Jill bath. Additional living space includes a 400-square-foot bonus room above the three-car garage, which is the 4th bedroom! Expansive unfinished walk-up attic conveniently located off the kitchen—presenting exceptional potential for future customization. Outdoors, the home unfolds into a private sanctuary. Enjoy tranquil countryside views from the front porch swing, entertain on the covered rear patio, or unwind beside the in-ground saltwater pool, creating an idyllic backdrop for both relaxation and gatherings. A rare opportunity to own a luxurious, turnkey property offering serene acreage, upscale finishes, and unmatched proximity to town.

2395 Becknerville Rd, Winchester
1701 Gay Evans Rd, Winchester
$821,000
4 Beds ⋅ 4 Baths ⋅ 26003645 MLS
If you need space, this one delivers. Sitting on just over 8 acres, this brick ranch offers privacy, room to breathe, and a layout that actually makes sense for everyday living. On the main level, you'll find the primary suite, two additional bedrooms, and a formal dining room that works just as well for holidays as it does for weeknight dinners. The heated and cooled sunroom is the kind of spot you'll end up using year-round — morning coffee, evening wind-down, watching the seasons change. A brand-new geothermal heating and cooling system was recently installed, giving you efficient, reliable comfort for years to come. The finished walkout basement adds even more flexibility. There's a private bedroom and full bath, a wet bar, and two bonus rooms that could easily be an office, gym, playroom, or hobby space. There's also a secure fireproof den and direct access outside to a concrete patio area — ready for a hot tub or outdoor seating setup. Outside is where this property really stands apart. The saltwater in-ground pool is ready for summer, and the acreage gives you the privacy you just can't fake. An invisible fence is already in place for pets. Garage space? You've got it. In addition to the attached two-car garage, there's a detached heated and cooled building with multiple bays and finished space — including an upper-level loft — ideal for a workshop, studio, guest setup, or whatever you've been wishing you had room for. Major bonus: the home is priced below appraisal. If you've been looking for land, function, and flexibility — without giving up comfort — this one is it.

1701 Gay Evans Rd, Winchester
1150 Craig Xing, Winchester
$800,000
5 Beds ⋅ 4 Baths ⋅ 26002724 MLS
Stunning new construction offering 5 bedrooms, 3.5 bathrooms, sitting on roughly 2.5 serene acres. This home is surrounded by picturesque farmland and panoramic views. 4 bedrooms are located on the main level for ultimate convenience. Offering the perfect blend of space, style, and serenity. Features include open concept layout, spacious kitchen with kitchen island, granite counter tops, hidden walk in pantry with custom cabinets and well appointed appliances. Hardwood floors and tile throughout. Primary bathroom is gorgeous with a freestanding soaker bathtub, tile shower, custom dual vanities and granite countertops. Unwind on the covered back porch. Cozy up by the stone fireplace in the great room. Enjoy the separate laundry room also with custom cabinets, folding space and granite. This home offers and abundance of sunlight and a side entry garage. Large walk-in storage room for all your extra items! Covered entry space for all your deliveries. Roughly 21 minutes to Hamburg in Lexington, 20 minutes to I-75 / I-64 interchange, with multiple drive options. Roughly 5 minutes to grocery options and variety stores. Don't wait to build, this one is move in ready, just add your decor and enjoy!

1150 Craig Xing, Winchester
1700 Cabin Creek Rd, Winchester
$775,000
3 Beds ⋅ 3 Baths ⋅ 26000753 MLS
The possibilities are endless with this exceptional rural property on 12+/- fully fenced acres. This beautifully updated 3-bedroom, 2.5-bath home features a renovated kitchen and baths, wide-plank cherry hardwood floors, heated travertine floors in two bathrooms, a spacious primary suite with sitting area and attached office or studio, dedicated laundry/mudroom with secondary pantry and a sunroom overlooking Trex decking. A detached garage offers approximately 900 sq ft of finished space along with a separate one-bedroom apartment complete with kitchen and bath—ideal for guests, extended family, or income potential. This land is designed for both relaxation and function with new fencing, automatic pasture waterers, fenced backyard, concrete driveway, and three truly unique barns including a fully renovated 9-stall barn, a well-preserved historic dairy barn with stalls, workshop space and paddocks, and an additional barn for shop and storage use. A climate-controlled party room with power and water adds even more flexibility for entertaining or events. This rare offering combines comfort, character, and unlimited potential!

1700 Cabin Creek Rd, Winchester
7300 Old Boonesboro Rd, Winchester
$772,500
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
4040 Muddy Creek Rd, Winchester
$759,000
4 Beds ⋅ 4 Baths ⋅ 25018691 MLS
A Farmhouse Retreat with Timeless Craftsmanship on 13.6 Acres Nestled on 13.6 rolling acres in Clark County, this custom built farmhouse captivates with soaring tongue-and-groove ceilings, rich woodwork, and thoughtful craftsmanship that sets this home apart. Oversized doors, custom cabinetry, and detailed finishes showcase the quality throughout, while two wood-burning fireplaces with homemade cherry wood mantles add warmth and character to the living spaces. The main-level primary suite features a decorative wooden ceiling, dual walk-in closets, a spa-inspired bath with a spacious double shower, and a freestanding soaking tub. The expansive kitchen and open-concept design makes the home perfect for gathering, while the composite wraparound porch—measuring more than 2,100 sq. ft. across all four sides—provides the perfect vantage point to enjoy breathtaking sunrises and sunsets The second level adds remarkable versatility with two bedrooms, each with large walk-in closets, a full bathroom with shower, and a generous open play area beneath striking pine wood tongue and grove ceilings.. A dedicated home office with gorgeous elevated views makes remote work convenient. Surrounding three sides of the home, a spacious attic storage area ensures ample room for organization. The newly finished basement extends the home's versatility with a complete second living area, including a full kitchen, living room, bedroom, bath, and private entranceideal for extended family, guests, or rental potential. Outdoors, the property offers exceptional amenities for both recreation and function. A two-story treehouse with slide and climbing wall provides a unique retreat for play or relaxation, perfectly complementing the serene setting . The centerpiece is a thoughtfully designed insulated metal barn, built with 2x6 framed walls and a truss-supported roof for lasting durability. One side houses a secure chicken coop with covered run, while a 14-foot-wide lean-to spans the full length of the barnideal for livestock shelter or working area. This versatile structure has its own electrical service and can serve as a workshop, storage space, agricultural hub, or indoor recreation during the winter months, offering endless possibilities for the next owner. The acreage is fully fenced with high-tensile woven wire and thoughtfully divided into four separate fields, making rotational grazing both practical and efficient. This setup supports a variety of livestock and enhances the property's potential as a working farm, hobby homestead, or versatile country estate

4040 Muddy Creek Rd, Winchester
3900 Mt Mount Sterling Rd, Winchester
$750,000
6 Beds ⋅ 5 Baths ⋅ 25500090 MLS
Sellers offering $10,000 towards closing cost and prepaids on an accepted offer. This extraordinary home located on 8.4 acres and nestled back from the main road, offers spectacular views from both the front and rear and those views can be enjoyed from the expansive covered front porch or the extra-large covered back porch. As you arrive, the meticulous care taken to maintain the property is apparent. Inside, discover a beautifully updated kitchen, five or six bedrooms if desired, and five total bathrooms, combining elegance and spaciousness in this stunning Cape Cod residence. Recent renovations include a new roof, windows, and heating and cooling systems, ensuring all major aspects are up-to-date. Beautiful hardwood floors, ample space, and a large unfinished basement with a half bath and additional garage area featuring a separate driveway provide endless possibilities. Easily accommodate an additional family member in the basement with their own living space. All above info is believed to be accurate buyer to confirm.

3900 Mt Mount Sterling Rd, Winchester
6356 Van Meter Rd, Winchester
$750,000
3 Beds ⋅ 3 Baths ⋅ 26012252 MLS
**Click on the Virtual Tour section to see the video walk through!** Nestled in the peaceful countryside of Winchester, this charming property on Van Meter Road offers the perfect blend of privacy, comfort, access and room to roam. Set on 13.74 beautiful, fenced acres and located within minutes of I-64, I-75 and the Mountain Parkway, this unique property offers easy access to Lexington, Winchester, Paris, and all of Central Kentucky. Enjoy wide-open spaces, scenic surroundings, and the tranquility of rural living minutes from city amenities. Designed for ease and functionality, the home features convenient one-level living with the added bonus of a finished basement--perfect for extra living space, entertaining, or hobbies. An inviting all-season room provides the ideal spot to relax year-round and a covered front porch overlooking a neighboring pond offers a tranquil place to enjoy your morning coffee or wind down at the end of the day. The kitchen features brand new stainless appliances, with transferrable warranties to the new owner. Did I mention the new roofs and Geothermal HVAC for efficient inside temperature control? Don't miss the first level primary bedroom with a private bathroom and walk in closet. Outside, the property really shines with a detached 3-car garage and a large barn with three stalls, a tack room and two multipurpose rooms. Also there is an additional metal barn with a tool room and three multipurpose rooms. All of these outbuildings have electricity and the wooden barn also has water with a separate fenced area for animals. Whether you're looking for a quiet retreat, a working or hobby farm, or a place to create lasting memories, this property delivers a warm and welcoming atmosphere you'll love coming home to.

6356 Van Meter Rd, Winchester
1783 Gay Evans Rd, Winchester
$750,000
5 Beds ⋅ 4 Baths ⋅ 25504530 MLS
Welcome to your dream homestead retreat! Tucked away on 7.27 beautiful acres, this stunning 5-bedroom, 4-bath home offers the perfect blend of comfort, function, and country living. From the inviting front porch sunsets to the resort-style outdoor space, this property has everything you've been searching for. Step inside to the two story foyer that leads to an open-concept main level featuring hardwood floors, a spacious living area, dining area and kitchen with granite countertops, an island and plenty of room for a breakfast table. Off the kitchen you have a large walk-in pantry, separate utility closet and oversized laundry room. The primary suite on the main floor offers convenience and luxury with a walk-in shower, whirlpool tub, double vanities, and generous walk-in closet. Upstairs you'll find a bedroom with ensuite, and three additional bedrooms, all with hardwood floors, three feature cedar-lined walk-in closets—perfect for storage and organization. Outdoor living shines here. Spend summers relaxing by the private swimming pool, enjoy peaceful evenings on the large back deck, have a fire around the firepit and enjoy the sunsets on the covered front porch. For hobbyists, horse lovers, small farm enthusiasts, or anyone needing serious storage and workspace, this property truly delivers: a 40' x 60' metal building with 14' x 16' garage doors, plumbed for a future bathroom and hookup for your RV, a 61' x 20.5' run-in shed with two stalls, a 10' x 40' barn, an additional storage shed, multiple paddocks, ideal for goats, horses, or small farm animals. Whether you're looking for privacy, a hobby farm, a place for your animals, or a home with room to roam, this property checks every box. With space, function, and beauty inside and out, you do not want to wait to schedule your private showing. Opportunities like this don't come around often—come experience it for yourself!

1783 Gay Evans Rd, Winchester
2509 Mount Sterling Rd, Winchester
$730,000
4 Beds ⋅ 4 Baths ⋅ 26015372 MLS
Escape to your own private retreat on 10+ breathtaking acres featuring a stunning 4-bedroom, 4-bath ranch home with over 4,000 square feet of living space and a full basement with unforgettable panoramic views. The bright, open kitchen offers granite countertops, abundant natural light, and a view you'll never tire of, along with an eat-in area and formal dining room. The spacious primary suite features a spa-like bathroom, and a dedicated home office provides the perfect space to work from home. Designed for the convenience of one-level living, the basement offers a full bath, generous storage, and endless possibilities for additional living or entertaining space. Outside is where this property truly shines—complete with a 6-stall barn, five fenced paddocks, and water lines to both the barn and each paddock, making it ideal for horses. This property has it all. Less than 3 miles to downtown Winchester and Lykins Park . This property is ready for entertaining, family gatherings, or simply enjoying the beauty and privacy this property offers.

2509 Mount Sterling Rd, Winchester
6500 Mount Sterling Rd, Winchester
$710,000
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
1775 Irvine Rd, Winchester
$700,000
3 Beds ⋅ 4 Baths ⋅ 26006681 MLS
Absolutely fabulous all brick home with incredible views, one owner, what makes this home special is the feeling of elegance, a total renovation offers the ultimate in living, spacious lower level provides full bath, family room, firepalce, walk out door to a large patio, first level dining room, great room with firepalce, showcase kitchen, living room, upstairs with large master suite, side offce or nursery, 2 fulls baths, 2 bedrooms, every window will have the most beautiful sunrises and sunsets, back door leads to the outdoor warm sunny deck overlooking green rolling hills, call today!

1775 Irvine Rd, Winchester
20 Stoney Brook Dr, Winchester
$660,000
5 Beds ⋅ 5 Baths ⋅ 26004633 MLS
Welcome to 20 Stoney Brook Drive. Step into luxury with this meticulously maintained executive home where no expense has been spared and every detail has been thoughtfully curated. Offering 5 bedrooms and 4.5 baths, a walk-out basement, this stunning residence features a grand two-story foyer that sets the tone for the elegance found throughout. Entering the home on the right, you will find a bedroom with coffered ceilings and a private ensuite—currently serving as a home office—alongside, on the left, a formal living room and dining room perfect for entertaining. The chef's kitchen is truly the heart of the home, showcasing a JennAir gas range, expansive granite island, double ovens, abundant cabinetry, and generous space for a large breakfast table. Just off the kitchen, step into your own elevated outdoor living space that feels like a serene treehouse, complete with a covered pergola ideal for relaxing or hosting guests. The inviting family room features custom built-ins, soaring vaulted ceilings, and a cozy gas fireplace, creating a warm yet refined gathering space. Upstairs, you'll find double doors leading to a luxurious owner's suite you may never want to leave. This private haven includes hardwood floors, a spacious layout, double tray ceilings, crown molding, a sitting room with a gas fireplace, and a spa-like bath featuring heated floors, a soaking tub, a walk-in shower, and separate his-and-her closets with built-ins. Three additional bedrooms, two of which share, and a full bath, along with a large laundry room, complete the upper level. The walkout basement is designed for both entertainment and functionality, offers living room wired surround sound, a built-in wet bar with wine fridge, a large game room, area, additional room that is being used as workout room, full bath, and ample storage. This could also make a wonderful in-law suite. Additional features include a central vacuum system for added convenience and easy maintenance, plantation shutters throughout, crown molding, fenced in yard, beautiful landscaping, and more. From top to bottom, this exceptional home blends sophistication, comfort, and thoughtful design—ready to welcome its next owners. If you've been waiting for that one home that has it all, one you can move right into and not do a thing, well, here is your chance. Call today to schedule your showing.

20 Stoney Brook Dr, Winchester
420 Alexis Way, Winchester
$660,000
4 Beds ⋅ 3 Baths ⋅ 25018220 MLS
Check out 420 Alexis Way in Winchester! This stunning home features a beautiful great room, fully equipped kitchen, extra garage and an inground pool. The primary suite is a luxurious retreat with a spa-like bathroom. With three additional bedrooms and a bonus room, there is plenty of space. The outdoor area is perfect for relaxing by the heated pool. Extra touches include crown molding and custom blinds. The detached garage is equipped with H/A and a dog wash area. Close to hospitals and shops. Motivated seller - don't miss out! Immediate possession available. 48 hr kickout clause active.

420 Alexis Way, Winchester
1108 W Lexington Ave, Winchester
$650,000
26010978 MLS
Rare opportunity to purchase a large multi-family development in the heart of Winchester! Directly across the street from Legacy Grove Park with Lexington Avenue frontage. All building and engineering plans available to build 66 approved townhomes with the possibility of adding 4 more. Currently zoned PD (Planned Development), could possibly be changed to commercial due to neighboring commercial property. Main property is 4.87 acres. Two other parcels will also be included, 220 and 231 (retention pond) Fairfield Way. No current infrastructure but some sewer materials already purchased. Seller would consider subdividing the large parcel to sell only the Lexington Ave side. The property can be accessed from Fairfield Way off of the new Fulton Rd extension. Please do not enter property without an appointment! Do not disturb tenants on Fairfield Way!

1108 W Lexington Ave, Winchester
142 Clubhouse Dr, Winchester
$650,000
6 Beds ⋅ 4 Baths ⋅ 26008332 MLS
Welcome to a lifestyle most only dream about — a stunning six-bedroom, four-bathroom residence perched along the lush fairways of Southwind Golf Course, complete with a lifetime membership for as long as you call this home. That's right, your morning coffee comes with panoramic views of manicured greens, and your evenings end with sunsets on the back porch. Inside, elegant double crown molding and wainscoting greet you in the entryway, setting a tone of refined sophistication throughout. The main level boasts nine-foot ceilings, a cozy family room anchored by a handsome fireplace, and a kitchen dressed in granite countertops and stainless steel appliances. The charming octagon-ceiling breakfast nook adds a touch of architectural whimsy to your morning routine. Upstairs, the primary bedroom features a stunning trey ceiling, while a conveniently located second-floor laundry room keeps daily chores effortless. The finished basement operates as a completely separate living space, offering its own kitchen, fireplace, and full bathroom — ideal for flexible living arrangements. Additional basement storage and a storm shelter/safe room beneath the porch provide practical peace of mind. Outside, a wraparound deck invites you to soak in those gorgeous views from every angle. Dual heating and cooling systems, poured concrete basement walls, and an oversized two-car garage round out this exceptional package. Nearby attractions include Winchester Traveling Trail and George Rogers Clark High School. Schedule your private tour today and discover what it feels like to live where every day feels like a getaway.

142 Clubhouse Dr, Winchester

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