luxury real estate for sale Winchester, United States

Now being offered for sale in Bourbon County, Kentucky is the long-established Green Valley Farm - a beautiful cattle and crop farm consisting of 896 +/- contiguous acres. This versatile farm offers thousands of feet of road frontage along Winchester Rd and Escondida Rd - in the immediate area of Stone Farm, Machmer Hall, Dapple Stud, etc. With roughly 60% of the farm in pasture, Green Valley has had a cattle farmer as a tenant through the years, there are currently no cows on the property. Roughly 30% of the farm is in crop production with a current main tenant producing $72,000 per year in rents and there is about 10% of the farm remaining in woods and creek. The gorgeous Green Creek runs throughout the property and there is an opportunity to harvest the walnut trees on parts of the wooded area. There are 5 tenant houses producing approximately $30,000 per year along with 10 storage barns throughout the farm which are all connected by gravel driveways. This is a massive property with great character and beauty along with being a productive cattle and crop operation- a truly unique opportunity !

4 Spectacular 10 acre lots available in Glennlake Estates. Decompress as you drive through horse country into the gated estate of Glennwood Lakes. Build your dream home and enjoy quiet evenings and starlit nights. Property boundaries are not warranted, please refer to recorded plat.

Rare opportunity to own this private 1930's home with a seamless mid-century addition just a short drive from downtown Lexington. The original part of the home with its stone construction is featured inside the home creating a charm that is unmatched. There are 5 striking fireplaces in the home including one in the kitchen, office and a huge stone fireplace in the great room. The rear of the home is a wall of windows overlooking the treed lot flooding the large space with natural light. The office, lined with bookshelves and complete with its own fireplace, feels like the perfect place to write the next great American novel. Or just take a Zoom call. And don't miss the hidden bookshelf door that opens to the primary suite, with its vaulted ceiling and custom step-down soaking tub. The renovated kitchen offers an oversized island and tons of counter and cabinet space. Spiral staircase to the basement with family room area, plenty of storage and bedroom with full bathroom and another gorgeous stone fireplace. Separate small building/finished activity room next to the home has endless potential. Private stone patio and front porch to take in the beautiful Kentucky setting. Detached oversized garage for RV storage! Worth the drive just South of Lexington with easy access from 1-75 or Old Richmond Road.

Tucked inside the gated community of Boone's Trace, this custom-built home offers over 5,000 square feet of beautifully finished living space, just minutes from both Lexington and Richmond. The open-concept main level is filled with natural light and scenic views, featuring a chef's kitchen with an oversized island, premium appliances, custom cabinetry, quartz and marble countertops, and a walk-in pantry. The spacious primary suite offers a spa-inspired bath and custom walk-in closet by California Closets, while two additional bedrooms and bathrooms, a private office, screened porch, mud room with built in storage, and custom dog wash in laundry room complete the main floor. Downstairs, the completely finished walkout basement, full of natural light, is designed for both entertainment and everyday living, featuring a spacious family room with fireplace, kitchen (sans oven), bedroom, full bath, dedicated gym, recreation area, and a second screened porch. Additional highlights include a corner lot, whole-home water filtration system, new tankless water heater, central vacuum, designer roof system with open metal valleys, professional landscape lighting, and newly installed gas lanterns at each exterior entrance. Enjoy beautiful sunset views around the gas fire pit on the back patio and experience all that Boone's Trace has to offer. Visit www.boonestrace.com for details on all community amenities, including an 18-hole championship golf course, pool, tennis/pickleball courts, and more!

Welcome to 3637 Horsemint Trail in Still Meadow, a Jimmy Nash Homes Community, where over 4,400 square feet of finished living space offers plenty of room to live, entertain and unwind. The main level is anchored by a bright, open kitchen and great room, with custom built-ins surrounding the fireplace and a spacious first-floor primary suite. The kitchen and baths were updated in 2025 featuring quartz countertops and updated finishes. Upstairs you'll find three additional bedrooms as well as a flexible bonus space, currently used as an office. Downstairs, the finished walkout basement adds an entirely new level of living with a large family room, bedroom, full bath, golf simulator, and abundant storage. The outdoor spaces are just as impressive with a Trex deck that leads to a covered porch complete with built-in heaters and speakers for your enjoyment all season long, while the patio and firepit below provides even more room to gather and enjoy the backyard. Conveniently located near schools and hospitals, with easy access to Hamburg, I-75 and downtown Lexington.

Handsome masonry construction and beautiful brickwork set the tone for this exceptional home, privately situated on three wooded acres in Boones Trace, where Hines Creek winds its way toward the Kentucky River. Arrive by the drive or follow the stone walkway to a gracious covered front porch. Inside, quality craftsmanship and an abundance of windows bring the beauty of the surrounding trees and wildlife into everyday living. Designed for effortless first-floor living, the open floor plan connects a well-appointed kitchen and dining area to the great room, where a stacked-stone fireplace creates a striking focal point. Granite countertops, abundant cabinetry, stainless appliances and a tile backsplash complete the kitchen. The inviting primary suite features its own fireplace, walls of windows and an ensuite bath with heated floors. A spectacular sunroom opens to the rear porch overlooking the peaceful wooded setting. An office with built-ins, bonus room and utility room complete the first floor. The walkout lower level offers a spacious family room, two bedrooms, a full bath and abundant storage, with convenient exterior ramp access if needed. An extra-wide two-car garage (22'9" x 23') adds everyday practicality. Three wooded acres, exceptional privacy, move-in-ready condition and room to gather, entertain or simply enjoy nature make this a rare opportunity to embrace the best of Kentucky living.

Nestled in the highly sought-after Ellerslie at Delong, this beautifully appointed home showcases timeless design, exceptional craftsmanship, and thoughtfully curated upgrades throughout. The main level welcomes you with elegant wainscoting, tiered ceilings with designer lighting, and extensive 6-inch crown molding. At the heart of the home is a chef's kitchen featuring premium appliances, a spacious walk-in pantry, and an open layout that flows seamlessly into the inviting great room with custom built-ins, a fireplace, and picturesque views of the greenspace beyond. Enjoy indoor-outdoor living with screened porches on both the main and lower levels overlooking the fully fenced backyard. Upstairs, three generously sized bedrooms each offer en suite baths, providing comfort and privacy for family or guests. The finished walkout basement is designed for entertaining, complete with a full bar, billiards area, digital home theater with whole-home audio zones, a full bath, and a dedicated fitness space that could easily serve as a fifth bedroom. Combining luxury finishes, flexible living spaces, and an unbeatable neighborhood setting, this home offers an exceptional lifestyle in one of Lexington's most desirable communities.

Nestled on a picturesque 1.03-acre lot along the highly desirable Walnut Hill Road, this charming 1961 home offers the perfect blend of timeless character and modern updates. Featuring 3 bedrooms, 1.5 baths, beautiful hardwood floors throughout, fresh interior paint, and brand-new kitchen appliances,Brand new HVAC unit installed on 2025, this home is move-in ready while maintaining its classic appeal. Surrounded by scenic horse farms, you'll enjoy the tranquility of Kentucky's countryside with the convenience of a fantastic location just minutes from town. Don't miss this rare opportunity to own a home in one of the area's most beautiful settings!

Stunning 1.5-story home with a finished walkout lower level, exceptional updates and thoughtfully designed living spaces throughout! The beautifully appointed main level features hardwood flooring, plantation shutters, formal dining room, private home office, and an impressive two-story family room with built-in bookcases and fireplace, seamlessly connected to the eat-in kitchen. The first-floor primary suite offers a luxurious retreat with a renovated, spa-inspired bathroom including tiled shower, soaking tub and spacious walk-in closet. A renovated and expanded mudroom/laundry room and updated powder room add both style and functionality. Upstairs are three generously sized bedrooms, with the flexibility for a fourth, two full bathrooms and an expansive flex space featuring a large closet and built-in workspaces, ideal for a second office, study area, playroom, gym or creative retreat. The finished walkout lower level offers exceptional versatility, with ADA accessibility features, a kitchenette, multiple living areas, a separate laundry room and a bedroom with built-ins, a spacious closet, two full bathrooms and brand new carpet. Ideal for multigenerational living, extended guest stays, or a variety of lifestyle needs. The beautifully renovated outdoor living spaces are equally impressive, featuring a covered deck, fireplace, firepit and stunning patio complete with outdoor cooking space. Enjoy peaceful views of mature trees and lush green space, creating a private, picturesque backdrop for relaxing or entertaining. With abundant upgrades including roof, heating and air, extensive renovations, flexible living spaces and inviting indoor-outdoor living, this exceptional home offers the perfect blend of comfort, functionality and timeless appeal.

A rare masterpiece of country elegance and modern luxury, this spectacular 10-acre estate offers unparalleled privacy just moments from the city. Designed for both grand-scale entertaining and serene daily living, the property features a resort-style custom pool, a tranquil zen garden with a koi pond, a custom playhouse, and a pristine pond complete with a newly installed fountain and a dedicated well pump to maintain perfect water levels. The expansive outdoor oasis is further elevated by updated custom pergolas, a brand-new fire pit, and a convenient outdoor shower. Inside, impeccable craftsmanship defines the 5-bedroom, 5-full, and 2-half-bath residence. The gourmet chef's kitchen is a culinary dream, boasting top-of-the-line appliances, endless workspace, and a massive walk-in pantry. The luxurious primary suite serves as a private sanctuary with panoramic nature views, bespoke custom closets, and a spa-like bath with a deep soaking tub. A collector's dream, the massive 8-door garage accommodates up to 15 vehicles and features a private home office above. Mechanically flawless, the estate includes freshly painted perimeter fencing and a reconnected full-property irrigation system with a new pond pump. The previous owner performed many high-end upgrades, including 3 geothermal HVAC units with UV light filters, a water pressure booster pump, enhanced foundation drainage, and full-house blown-in foam insulation for maximum energy efficiency.

Priced below recent appraisal! Lexington character, modern convenience. Tucked inside a charming neighborhood and mature trees, this Georgian Revival home 'checks all the boxes' for inspired living. This all-brick Jimmy Nash home welcomes family and friends with lush landscaping, private, rear entry 2 car garage, and secluded patio. Once inside, cathedral ceilings, exposed wood beams, gorgeous millwork, and light-filled spaces abound. Primary suites on both the first and second floors, first floor laundry, unfinished full basement, abundant storage and gas fireplace add to the appeal. The kitchen invites culinary creativity with all new appliances, eat in dining space, granite countertops with seating, and tiled backsplash. The formal dining room is ready for any gathering. Peace of mind comes from a newer roof (2023), furnace (2025), and whole-home surge protection, plus backup Generac generator. Easy access to Downtown, Hamburg & I-75. Additional amenities are numerous, so schedule your tour, and be inspired, today.

Charming Townhouse at 2537 Danielle Lane! Townhouse features three spacious bedrooms and two and a half bathrooms, perfect for comfortable living. The moment you step inside, you'll notice laminate and carpet flooring that flows seamlessly throughout the home. The kitchen, featuring stainless appliances and granite counter tops, opens to the living and dining areas, creating an ideal space for entertaining family and friends. Enjoy cozy evenings on your front porch or back patio, where you can unwind. With a convenient two-car garage, you'll have plenty of space for vehicles and storage. Located in Lexington, this townhouse offers both comfort and convenience, making it the perfect place to call home.

Charm and function collide in the most pleasing way in this adorable powder blue Cape Cod in the convenient and popular Henry Clay neighborhood. Original hardwood floors, replacement windows and a dreamy cottage-core renovated kitchen with new appliances, including a gas range, quartz countertops, custom mill work and new cabinetry. So many thoughtful extras have been added over the years to lovingly maintain and elevate this home, including a cozy breakfast banquette, beadboard accents, new flooring on the second floor and replacement interior doors throughout. An updated full bath and two nicely sized bedrooms are on the first floor. Upstairs, you'll find ample ceiling height and closets on both sides, creating a flexible space that could be an office, playroom, large bedroom or two smaller ones. A private back patio overlooks the almost quarter-acre, fully fenced backyard (bring on the pups!) with endless possibilities. Move-in ready for fall fire pits and cozy nights, with plenty of room to dream about a huge spring garden. This home is a gem, and the next owner is a lucky one.

Looking for that sport horse facility that truly has it all ? Located just 10 minutes from the Kentucky Horse Park on the desirable Greenwich Pike, this gorgeous sport horse facility has been thoughtfully engineered to deliver for you and your horses ! At 106.9 acres, you will discover its open, rectangular shape with gently rolling land - making for a peaceful and private setting. The centerpiece of the farm is a magnificent concrete block training barn featuring (20) 12' x 14' rubber-matted stalls with a heated waterer system in each stall. Additionally, each stall has an exterior door with overhang roof - this provides excellent cross ventilation and gives the horses great views of the farm ! The barn also has a tack room (with 1/2 bath), a feed room and a recently expanded tack room area with grooming racks and a wash rack. The huge hay loft has ample room for hay, shavings, etc and features a roughed-in apartment area if desired to finish out. Just off the barn area are numerous training options for the professional horseman. There are 2 synthetic outdoor rings - a 100'x200' dressage ring and a 160' x 300' oval shaped jumping arena to go with a 120' x 220' grass jumping arena. There is also a fully covered 70' sand round pen and a fully covered 6 horse Eurociser. Completing the farm improvements are 13 individual fenced paddocks, 4 large fenced fields - all with auto waterers and 2 large hoop barns for covered storage . The 5 BR 2.5 BA cottage-style house has been completely renovated over the past several years from top to bottom including: all new kitchen flooring, tops, cabinets, appliances, recently renovated baths, newer electrical service, HVAC systems, a high performance standing seam metal roof system, cement board siding, high performance Sierra Pacific windows and doors, added covered patio and carport. There is also a detached garage / shop area with solar panels making electric bills reasonable. Come discover this professional sport horse farm !

Easy living in this charming, larger-than-expected ranch in Lexington's favorite neighborhood- Kenwick. An inviting covered front porch leads inside to another unexpected delight; a vaulted living room that gives this 1930s-era home a fresh, contemporary feel. The updated chef's kitchen with gas range, Shaker-style cabinets and marble countertops opens to a spacious family room/dining room combination with built-ins. A nicely sized, sunny laundry room with washer and dryer adds convenience and could double as a pantry or extra storage. The updated full bath features subway tile and a soaking tub. Three bedrooms include one with a dreamy walk-in closet and custom shelving. The large, private, fully fenced backyard with plenty of room to expand the garden, use the fire pit as the fall approaches or host a barbecue. Don't miss this total package; a charming Kenwick home with great living spaces, thoughtful updates and a gorgeous lot!

Ideally located and thoughtfully updated brick ranch in sought-after Lakeview (40502), set on a large, beautifully landscaped and treed lot with a walkout basement. This home has had significant recent investment, including a new deck completed in 2025 (over $65,000), new windows (over $40,000), a new HVAC system in 2025, spray foam insulation in the attic, and new carpet in 2023. Inside, you'll find travertine tile, granite counters, updated cabinetry, a kitchen island, crown moldings, fresh paint, and LED lighting throughout. Additional updates include new garage doors and an inviting courtyard. This is a very pleasant home filled with great natural light and an easy, social flow for everyday living and entertaining. Enjoy walking to Henry Clay and beautiful Lakeview Park, with its walking trails and playground.

Set in Lexington's beloved Fairway neighborhood, this charming stone home beautifully blends classic character with thoughtful updates and inviting spaces. A timeless tile roof and mature boxwoods frame the entry, creating an unforgettable first impression. Inside, the foyer opens to both the dining room and family room. You will love the 9 foot ceilings and original hardwood floors throughout the main level. The family room features an original fireplace and adjacent sitting area with built-ins, offering the flexibility to serve as a playroom, or home office. Generously sized, the dining room is ready for everything from weeknight dinners to big family gatherings. The kitchen features inset cabinetry with granite countertops, stainless steel appliances, and fantastic natural light with windows overlooking the private backyard. At the back entry, a dry bar with wine storage and a beverage refrigerator adds both function and style. Upstairs, the primary bedroom offers beautiful built-ins for both storage and display, along with a private en-suite bath. Two additional bedrooms share a hall bath with a combination tub/shower. Outside, the backyard features a large patio and mature trees—perfect for relaxed evenings and outdoor entertaining. The extended one-car garage offers a great deal of additional storage space for bikes and outdoor equipment. With its original details, abundant natural light, and coveted Fairway address, this special home offers the perfect combination of timeless Lexington charm and comfortable everyday living.

Set at the end of a quiet cul-de-sac on a beautifully wooded, nearly half-acre lot, this meticulously maintained and thoughtfully updated executive home in the sought-after Woods subdivision offers an exceptional blend of elegance, comfort, and privacy—all in one of Lexington's most convenient locations. From the moment you enter, the home reveals a level of design and craftsmanship that is both sophisticated and inviting. The stunning sitting room, beautifully decorated by Matt Carter, features custom built-ins and dramatic lacquered walls, creating a distinctive space for conversation and entertaining. Just beyond, the impressive two-story family room takes center stage with a stacked-stone fireplace, hardwood floors, and newly added built-in bookcases. The main level is designed for both everyday living and gracious entertaining. A private office offers flexibility and could easily serve as a first-floor bedroom if desired. The inviting eat-in kitchen features double doors opening to the back porch, seamlessly connecting indoor and outdoor living. A formal dining room, laundry room, and half bath complete the first floor. Upstairs, the spacious primary suite is a true retreat, featuring an updated bath and a newly renovated closet that is nothing short of spectacular. Three additional bedrooms and a full bath provide generous accommodations for family and guests. The walk-out lower level adds another dimension to this already impressive home, offering a family room, recreation room, full bath, and direct access to the expansive, private backyard. With multiple gathering spaces and room to relax, play, and entertain, this home effortlessly adapts to the way you live. Perfectly positioned inside New Circle Road, this exceptional property offers easy access to the University of Kentucky, downtown Lexington, premier shopping, restaurants, and all that the city has to offer. Beautifully updated. Exceptionally located. Unmistakably home.

Completely reimagined from top to bottom, 443 Morgan Avenue offers the perfect blend of charm and modern convenience! This spacious 4-bedroom, 3.5-bath home boasts 2,054 sq. ft. of thoughtfully renovated living space. You'll love the gleaming new hardwood floors and open-concept layout that flows effortlessly from room to room. The brand new kitchen features butcher block countertops, stylish cabinetry, and new Frigidaire appliances including a smooth-top electric range and stackable washer/dryer (mud room w/sink). Major upgrades include a new HVAC system, new plumbing throughout, new 200-amp electric panel and new wiring throughout, new bathrooms, new outlets and fixtures, new vinyl siding, new drywall throughout and fresh interior paint, new tankless water heater, new energy-efficient windows and new insulation throughout including new spray foam insulation in crawlspace, ensuring comfort and efficiency. Step outside to enjoy both a welcoming front porch and a new covered back deck, ideal for relaxing or entertaining. This move-in-ready home is a rare gem in a convenient Lexington location!. Virtually everything is new in this home, all it needs now is a new homeowner! See Seller's Disclosure for a more detailed list of updates!

Located in the highly coveted Lakewood neighborhood, this beautifully updated ranch offers refined living with a peaceful water backdrop and over 4,400 sq. ft. of finished space with 2-3 bedrooms and 3 and a half baths. Architectural elegance defines the home from the moment you arrive. Lavish woodwork, elaborate trim details, and abundant custom cabinetry complement gleaming hardwood floors and timeless millwork throughout. A gracious foyer with fanlight transoms and elegant archways introduces the formal living room and handsome wood-paneled library with fireplace. French doors extend the living space to an elevated brick terrace overlooking the manicured grounds and serene pond. The gourmet kitchen impresses with vaulted ceilings, exposed beams, two large islands, and designer finishes, opening seamlessly into a stunning hearth room framed by floor-to-ceiling windows, skylights, and a striking stone fireplace. The private primary suite evokes spa-like luxury with marble flooring, a freestanding soaking tub, an expansive glass shower, dual vanities, and sunlit windows that capture the tranquil setting. The finished walk-out lower level expands the home's versatility with a spacious family room, custom built-ins, an office nook, a convenient kitchenette, possible 3rd bedroom suite, and French doors leading to a screened porch perfectly positioned to enjoy pond views. Professional landscaping, a stack-stone wall, and multiple outdoor living areas enhance the property's beauty and livability. With three fireplaces, premium craftsmanship, and a location among Lexington's most desirable addresses, this home offers a rare blend of timeless elegance and everyday comfort--an exceptional Lakewood opportunity.

Nestled in the heart of one of Lexington's most vibrant and sought-after neighborhoods, 310 Hanover Court offers a rare opportunity to buy into Kenwick and customize a property from the ground up. Currently functioning as a large single-family residence, this property was previously a duplex and retains a highly adaptable footprint that can easily be converted back to its original multi-unit layout. Offered strictly as-is, it is an ideal project for an investor or an ambitious buyer looking to build sweat equity, whether that means renovating it into a single-family home or living in one side while renting out the other to offset the mortgage. While the interior awaits your updates, the property features strong structural fundamentals, including a newer roof, a newer water heater, and updated vinyl windows already in place. The exterior also adds significant value with a detached garage fully equipped with a room for a workbench area and storage space. Combining a premier location just minutes from downtown with endless upside, this Kenwick property is a blank slate ready for its next chapter.

Home for the holidays! This one-owner, well-maintained Colonial in the popular Lans-Merik neighborhood is conveniently located near the University of Kentucky, parks and schools. A modern floorplan with an open kitchen and great room combination with a wood-burning masonry fireplace, built-ins and access to a private brick patio and large backyard. The cozy living room has so many windows it could easily double as a sunroom, while the unexpected bonus of a butler's pantry makes the space ready for holiday parties! Hardwood floors throughout the first floor. Upstairs, you'll find four generous bedrooms, including a beautifully renovated, spa-like bathroom with a walk-in shower, custom vanity and super convenient laundry area. A bonus room offers just the right spot for a petite home office or extra storage. An attached two-car garage and a spacious, private backyard with plenty of room for a firepit. Enjoy the convenience of 40502 and only a short walk to shopping and dining at Chinoe Plaza!

Rare opportunity to own a beautifully updated triplex in Lexington's highly sought-after Chevy Chase neighborhood. 304-306 Ridgeway Drive features three 1BR/1BA units and is being sold partially furnished. Ideally located just steps from the University of Kentucky, downtown Lexington, UK HealthCare, restaurants, shopping, and entertainment. With thoughtful updates and an unbeatable location, this property offers incredible flexibility and a unique opportunity to own in one of Lexington's most desirable areas.