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.

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 548 Bulrush Trace! This well-maintained ranch has been freshly updated and is ready for its next owner. The home features fresh paint and new LVP flooring throughout, giving the interior a clean, updated feel. The kitchen has also been refreshed with new Quartz countertops and offers a comfortable layout that flows easily into the main living areas. With 3 bedrooms and 2 full baths, the one-level floor plan is both functional and inviting, including a primary suite with its own private bath. Out back, the covered porch provides a great spot to relax, entertain, or enjoy the outdoors in almost any weather. An attached 2-car garage and manageable yard add to the convenience. Located in southeast Lexington with easy access to shopping, dining, and major roadways, this move-in ready ranch offers comfortable one-level living with thoughtful updates already in place.

Welcome to luxury country living in the heart of the desirable Houston Oaks neighborhood! This exceptional 5-bedroom, 4-bath home (with 2 half baths) sits majestically on over one acre of pristine, tree-lined property—your private sanctuary away from the everyday hustle. The Perfect Setting Imagine peaceful evenings surrounded by mature trees that frame this stunning residence, offering the privacy and tranquility every homeowner dreams of. This is more than a house; it's your personal escape in one of Paris, Kentucky's most sought-after communities. Thoughtfully Upgraded & Beautifully Maintained The current owners have invested significantly in premium upgrades and improvements throughout. You'll discover: Spacious, chef's kitchen featuring granite countertops and top-of-the-line appliances, rich hardwood floors that flow throughout the home, meticulous attention to detail in every room, comprehensive seller's disclosure documenting all recent enhancements Energy-Efficient Excellence State-of-the-art geothermal heating and cooling system delivers exceptional energy efficiency and superior cost savings—keeping your home comfortable year-round while reducing utility expenses significantly. Must See to Appreciate this home's true beauty and quality are best experienced in person. The combination of luxury finishes, thoughtful upgrades, energy efficiency, and serene acreage make this an exceptional offering in today's market.

Location, location, location—centrally located with easy access to I-75, shopping, restaurants, and downtown. 15.1 ± acre mini farm featuring a 2.5-acre stocked pond, gunite pool, and a five-bent tobacco barn converted into a six-stall horse barn (with hot/cold water supply, heated office, and tack room). 3,607 sq ft home built in 1953 and fully remodeled in 2016 with all-new electrical, plumbing, roof, appliances, and fixtures. Offers 4 bedrooms and 3 full baths (one bedroom converted to a large primary walk-in closet; easily converted back). Large, detached 3-car garage with updated Raynor garage doors. Primary bathroom features a large marble-tiled walk-in shower, wood tile flooring, double vanity, and infrared sauna. Expansive open kitchen with Sub-Zero refrigerator, Thermador gas range with double ovens, and large island with quartzite countertop. Oversized living room with custom barnwood built-in, wainscoting/shiplap, and adjacent storage room. Large first-floor laundry room with custom-designed double pantry closets. Generac whole-house generator. Unfinished basement with abundant storage space and gym/recreational area. Additional renovations in 2018 include a newly added automatic front entry gate with keypad and posts, as well as a Colorado-style outdoor patio with Trex decking and stone tiling. Property features V-mesh and four-board horse fencing throughout, along with multiple run-in sheds and equipment/livestock barns.

Welcome to your dream townhome in the heart of Hamburg! This stunning, all-brick property offers the perfect blend of low-maintenance luxury and unbeatable convenience, featuring 3 spacious bedrooms, 2.5 beautifully appointed baths, and an attached 2-car garage. Inside, the home is loaded with premium touches, including elegant crown molding and timeless plantation blinds, while a brand-new HVAC system and newer roof provide ultimate peace of mind. The seamless layout opens up to a private patio perfect for relaxing, all situated just minutes from the I-64 and I-75 interstates for an effortless commute.

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!

Experience lakeside living on Greenbrier Lake in this custom-built residence offering more than 6,600 square feet of thoughtfully designed space. With nearly two acres that roll gently toward the water, the setting provides privacy, wide open lake views, and a natural backdrop for both gathering and retreat. The main level features hardwood floors, custom cabinetry, and soaring ceilings, with each bedroom designed as a private suite with its own bath. A large sunroom, ideal as an office or additional family space, captures sunlight and views throughout the day. The home's lower level offers a full second kitchen, living and dining areas, utility room, and a stone fireplace, making it well-suited for multigenerational living or guest quarters. In total, the home offers five bedrooms, a theater room with 12-inch poured concrete walls, and architectural details like a dramatic winding staircase beneath the soaring great room ceiling. Outdoor living is equally inviting, with expansive decks and patios overlooking the lake and access to the water only steps away. The rural setting offers the tranquility of a waterfront retreat yet remains just 3.5 miles from everyday conveniences, and a short drive to Lexington via I-64. This is a rare opportunity to own a spacious waterfront home that blends craftsmanship, functionality, and setting in one exceptional property.

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.

Renovated, move-in ready, and ideally situated on a quiet court—this beautiful two-story home has it all! Featuring 3 bedrooms and 2.5 baths, this home offers a thoughtfully updated interior, spacious living areas, and a large, flat backyard. The main level welcomes you with a foyer and dining room featuring a tray ceiling. The beautifully renovated kitchen offers new cabinetry with soft-close doors and drawers, granite countertops, and new stainless-steel range, microwave, and dishwasher. The spacious great room features a fireplace and overlooks the backyard and brand-new deck, creating an inviting space for both everyday living and entertaining. A convenient half bath completes the first floor. Upstairs, the spacious primary suite features a completely updated private bath with a brand-new tub/shower combination, fixtures, vanity with soft-close doors, mirror, and lighting. Two additional bedrooms share an updated full bath featuring a new vanity with soft-close doors, fixtures, mirror, and lighting. Additional improvements include fresh paint, new lighting and blinds, luxury vinyl plank flooring throughout the first level and all bathrooms, and new carpet on the stairs and throughout the bedrooms. The attached garage includes an automatic opener. With extensive updates already completed, a great location, a quiet court setting, and a spacious flat yard, this home is ready for its new owners.

PRICED AT APPRAISAL! Squire Oak! What a hidden gem! 2-story situated on a tree-lined court with a huge yard with wild flowers and more backing to a farm. This 3-bedroom features 2.5 baths on a full, partially finished basement. The first floor has nice dining area, a front-to-back large living space with doors that open to the wonderful backyard with patio seating area and double trellises. You will feel as though you are visiting the arboretum. Large kitchen with seating area and built-ins, also a walkout to the backyard. The basement area has a family room with built-ins, a recreation area, and a utility storage room. Also includes a 1-car garage. Updates to the home, bathrooms updated 5 years ago, and windows replaced 8 years ago.

Beautiful Williamsburg-style brick Townhome in the highly desirable Chippendale Square off of Patchen Drive, offering timeless architecture, exceptional craftsmanship, and a convenient location just minutes from downtown Lexington, shopping, dining, and New Circle Road. Situated in a beautifully maintained park-like setting, this move-in ready home features 4 bedrooms, 3.5 baths, two primary suites (one on the first floor and one on the second), and an abundance of character throughout. The first level features an Entry Foyer, Living Room with Fireplace, Dining Room with Fireplace, Primary Suite and Full Bath (currently used as an office), Utility Room, ½ Bath, a renovated Kitchen which is equipped with Stainless steel appliances including a gas range and it opens to a cozy breakfast nook with fireplace. The 2nd level features the 2nd Primary Suite with Fireplace and renovated Bath with tiled walk-in shower, 2 additional Bedrooms and 3rd Full Renovated Bath. The spacious interior showcases beautiful hardwood floors, 9-foot ceilings, exposed beams, extensive crown and dental moldings, custom millwork, built-ins, and four fireplaces with handcrafted wood surrounds. and inviting living spaces designed for both everyday living and entertaining. The lower level features a recreation room and large unfinished storage area. A walk-up attic with permanent stairs and flooring provides outstanding potential for future expansion, a studio, or abundant storage. Outdoor living is equally impressive with a private enclosed courtyard and a one-car garage. Additional guest parking is available. This truly unique home seamlessly blends historic Williamsburg charm with modern updates and amenities.

Location, location — and then some. 2775 Paris Pike has been masterfully reimagined from top to bottom, blending timeless character with the ease and confidence of a brand-new home. Every room has been touched: all-new custom windows and doors throughout, all-new plumbing, a new heat pump (2023), new roof and maintenance-free shaker siding (2025), all-new insulation, and a brand-new septic system. The heart of this home is a stunning kitchen featuring custom cabinetry, new countertops and flooring, a center island, and new KitchenAid appliances — anchored by a custom pantry with a coffee/wine counter, floor-to-ceiling storage cabinets, and a drawer microwave. An original window was replaced with a door opening to a private side patio nestled beneath the magnolias — perfect for al fresco entertaining. The family room impresses with a custom coffered ceiling and beautifully restored original glass pocket doors. First-floor conveniences include a newly added laundry room with custom cabinetry and pull-out organization, a tile-wall half bath, and a main-floor primary suite with custom glass shower, two new vanities with mirrored storage, and a bench with storage below. Upstairs, find two generous bedrooms — one with a custom closet, barn doors, and access to a private patio — plus a serene study/nursery with a custom wood ceiling, a fully remodeled bath with marble flooring and glass shower panel, and new storage cabinetry throughout. The exterior shines just as brightly: modernized columns, a fully replaced front and side porch with widened stairs, all-new landscaping-ready curb appeal, and fresh paint inside and out. This is the one you've been waiting for.

Set on approximately 5 acres, this equestrian property offers the perfect blend of functionality and location—just minutes from downtown Lexington and the Kentucky Horse Park. Thoughtfully designed for the dedicated equestrian, the farm features a premium 120' x 200' GGT footing arena complete with irrigation. The property also boasts 10-matted stalls with beautiful new stall fronts, a separate barn bathroom, laundry room, and a stylish temperature controlled tackroom. The charming 2-bedroom, 1.5-bath. residence offers comfortable living with a full basement that presents excellent potential for additional finished space—perfect for expanding your living area, creating a home office, or adding guest accommodations. A new septic has recently been installed along with new water heater (both 2024) and the entire house has new plumbing. Whether you're seeking a private equestrian retreat or a refined hobby farm in the heart of horse country, this property offers an exceptional blend of convenience, quality, and opportunity in one of Kentucky's most coveted locations.

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!

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.

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.