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luxury house with terrace for sale Winchester, United States

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Farmhouse with outbuildings and garden Winchester (United States)

A Rare 136± Acre Kentucky Estate with Private Airstrip, Custom Home & Aviation/Equestrian Facilities Privacy, commanding views, and the natural beauty of Kentucky's renowned horse country define this truly exceptional 136± acre recreational estate. Offering an extraordinary combination of luxury living, aviation, equestrian amenities, and recreational opportunities, the property has been thoughtfully designed to provide both functionality and tranquility. The setting is simply spectacular, with Nursery Place Thoroughbreds and Harkness Edwards Winery as immediate neighbors, placing this estate in an impressive equestrian environment just minutes from Fayette County. A winding private drive passes stocked ponds and the property's private grass airstrip, leading to the highest point of the estate where an impressive custom stone residence and versatile aviation/equestrian facility command panoramic views. The recently completed 5,800± square-foot custom home combines elegant finishes with a warm, modern farmhouse aesthetic. Features include rustic boxcar-wood flooring, a custom kitchen with granite center island and countertops, Wolf and Sub-Zero appliances, and custom cabinetry. The spectacular great room provides generous space for both living and dining, highlighted by a floor-to-ceiling stone fireplace and an expansive wall of windows framing remarkable views of the surrounding countryside. Both the great room and first-floor primary suite open onto a massive covered deck featuring an outdoor fireplace and hot tub—an exceptional setting for entertaining or simply enjoying the serenity of the property. The private main floor primary suite includes its own fireplace, luxurious en suite bath, large walk-in closet, convenient laundry area, and private office. A beautiful stone entrance foyer leads to a loft overlooking the great room. The walkout lower level features two additional spacious bedrooms and an open family room, with direct access through the walkout doors to the impressive in-ground swimming pool. Adding another dimension to the estate is the remarkable barndominium/aircraft hangar/woodshop, complete with approximately 1,000 square feet of living quarters featuring one bedroom and 1½ baths. The clear-span main building is designed for extraordinary versatility, capable of accommodating two small aircraft, one aircraft and one helicopter, or 8+ collector cars, RVs, and other recreational vehicles. Impressive hydraulic doors and extra-tall ceilings provide easy access. Inside, rustic barnwood finishes create a warm and inviting atmosphere ideal for entertaining, gatherings, or displaying a collection. A substantial woodshop with additional storage extends along the edge of the building. The lower level incorporates a substantial barn area with four horse stalls, tack room, hay storage, and tractor/mower storage, with convenient access to the approximately 10-acre fenced field for horse turnout. Whether envisioned as a private aviation retreat, equestrian estate, recreational compound, luxury country residence, or a combination of all four, this property offers a rare level of amenities and versatility in one of Central Kentucky's most desirable settings. A property of this caliber and combination of features is rarely offered. Located just minutes from Fayette County, it truly must be seen to be appreciated.

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$5,495,000
4bedrooms
4bathrooms
land 55.4ha

By Bluegrass Sotheby's International Realty

13 listings near Winchester

Nearby
50

House with garden and terrace Richmond (United States)

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!

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$949,000
4bedrooms
4bathrooms
land 0.2ha

By Bluegrass Sotheby's International Realty

Nearby
46
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House with terrace Lexington (United States)

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.

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$899,000
5bedrooms
4bathrooms
land 0.1ha

By Bluegrass Sotheby's International Realty

Nearby
48

House with garden and terrace Lexington (United States)

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!

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$580,000
3bedrooms
2bathrooms
land 0.4ha

By Bluegrass Sotheby's International Realty

Nearby
47

House with terrace Lexington (United States)

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.

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$279,000
3bedrooms
3bathrooms
land 0ha

By Bluegrass Sotheby's International Realty

Nearby
48

House with terrace Lexington (United States)

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.

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$329,900
3bedrooms
3bathrooms
land 0.1ha

By Bluegrass Sotheby's International Realty

Nearby
50

House with terrace Lexington (United States)

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.

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$899,900
5bedrooms
3bathrooms
land 0.2ha

By Bluegrass Sotheby's International Realty

Nearby
50

House with garden and terrace Lexington (United States)

Charming and full of character, this inviting bungalow is ideally located in Lexington's popular Kenwick neighborhood. A welcoming front porch sets the tone and offers the perfect spot to relax and enjoy this vibrant, established community. Inside, the thoughtfully designed floor plan features a desirable first-floor primary bedroom, along with a comfortable living room, dining room, kitchen, utility room, and cozy den—offering ample space for everyday living and entertaining. Upstairs, you'll find two additional bedrooms, a full bath, and a versatile office, ideal for working from home or creating a quiet study or reading space. Outside, the fenced backyard provides privacy and room to enjoy the outdoors. A large two-car garage offers excellent additional storage, while the recently finished exercise room above adds valuable and flexible bonus space. Enjoy all that Kenwick has to offer, with convenient access to downtown Lexington, Chevy Chase, the University of Kentucky and the popular shops, restaurants, and gathering spots along National Avenue. A wonderful combination of classic bungalow charm, flexible living space, and an exceptional in-town location!

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$589,000
3bedrooms
2bathrooms
land 0.1ha

By Bluegrass Sotheby's International Realty

Nearby
50

House with garden and terrace Lexington (United States)

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.

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$2,259,000
418m²
2bedrooms
4bathrooms
land 0.3ha

By Bluegrass Sotheby's International Realty

Nearby
43
Video

House with garden and terrace Lexington (United States)

You will instantly love this extraordinary setting, exceptional craftsmanship in a home that looks and lives like new! Set on one beautifully landscaped acre and framed by 200 acres of protected green space, this Vine Grove residence pairs timeless architecture with an enviable sense of privacy. Built by Mike Kerwin Homes, its classic exterior makes a memorable first impression, with a curved walk, covered porch with wood ceiling, twin French doors and a striking double-arched, 12-light entry door. Inside, every detail thoughtfully considered. Hardwood floors flow through the first level, where the gracious foyer introduces a private office, elegant dining room and handsome butler's pantry. Beyond, the great room is the heart of the home, with a coffered ceiling, fireplace, custom built-ins and walls of windows framing the spectacular setting. The adjoining designer kitchen is equally impressive, with an oversized island, quartz surfaces, farm sink, double ovens, gas cooktop, illuminated cabinetry and walk-in scullery. The first-floor primary suite captures the green-space views and offers a beautifully appointed bath and generous walk-in closet. Upstairs, four bedrooms each feature an en suite bath, joined by a charming reading room, second utility room and 1,000-square-foot playroom ready for finishing. The daylight lower level adds a recreation room, kitchenette, bedroom, full bath and abundant storage. Outside, the covered patio opens to a remarkable expanse of lawn and green space—an extraordinary backdrop for play, entertaining and memories made!

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$1,995,000
6bedrooms
7bathrooms
land 0.4ha

By Bluegrass Sotheby's International Realty

Nearby
50

House with garden and terrace Lexington (United States)

Craftsman beauty in the heart of Ashland Park—and an exceptional opportunity to make this special property your own. Lovingly maintained by the same owners for almost 30 years, this home retains many of the timeless architectural details that make a Craftsman so special; broad eaves, original hardwood floors, tall ceilings, built-in shelving and a dreamy full-length front porch. The natural light throughout is phenomenal. The renovated kitchen was carefully designed for a chef, with a gas range, lots of counter space and plenty of custom cabinetry. Spacious first-floor living includes a large living room with cozy fireplace, dining room AND a sunny family room with built-ins and a wall of windows overlooking the private backyard. Upstairs are three absolutely charming bedrooms with surprisingly generous closet space, a full bath and an additional large closet. The unique, original porte-cochère with convenient access from the front porch is the icing on the cake. Great bones, wonderful proportions, incredible character and one of Lexington's most beautiful, tree-filled neighborhoods. Walk to all the urban shopping and dining options in Chevy Chase, then stroll over to the Henry Clay Estate just blocks away to soak up the fall beauty.

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$675,000
3bedrooms
2bathrooms
land 518m²

By Bluegrass Sotheby's International Realty

Nearby
50
Video

House with garden and terrace Lexington (United States)

Bell Court BEAUTY just minutes from thriving downtown Lexington tucked away in one of the city's most iconic historic neighborhoods. This post-Victorian era home is filled with the charm and original architectural details of the early 1900s, thoughtfully paired with modern updates that make the home as livable as it is beautiful. Leaded glass windows, wide moldings, tall ceilings, gorgeous original hardwood floors, pocket doors and unique fireplaces are just a few of the historic details preserved and still in place. Spacious light filled living, dining and family rooms and a timeless front parlor. The updated chef's kitchen is complete with a cozy corner window seat--the perfect spot to watch the action or sneak in a nap. Just off the kitchen, a screened porch offers another favorite place to relax and enjoy the outdoors (without the bugs!) and private backyard views. Upstairs, the sunroom overlooking the tree-canopied streets of Bell Court makes the most perfect home office or reading room. Three spacious bedrooms include a primary suite with a bonus room and access to the second-floor porch, plus a walk-in closet and beautifully updated bath with both a soaking tub and tiled shower. The finished third floor could serve as a large bedroom with its huge walk-in closet or another common living space with endless possibilities. Outside, the dreamy front porch is exactly what you want in a historic neighborhood like Bell Court with its annual Front Porch Festival. The private backyard feels like its own little oasis, with a patio, mature landscaping, plenty of room to relax or entertain and a detached 2-car garage. Historic charm, modern comfort in one of Lexington's most beloved neighborhoods a short stroll to the shopping and dining of Chevy Chase AND downtown to catch a movie at the Kentucky Theater, the Saturday farmers market and a UK basketball game at Rupp Arena.

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$900,000
4bedrooms
3bathrooms
land 0.1ha

By Bluegrass Sotheby's International Realty

Nearby
33

House with garden and terrace Lexington (United States)

Welcome to 4664 Hathway Drive! This ranch-style home offers 1,309 square feet of convenient one-level living with three bedrooms and two full bathrooms. All bedrooms are located on the main floor, making the layout comfortable and functional. The kitchen is equipped with a range, dishwasher, and refrigerator and offers plenty of opportunity to create a space that reflects your own style. Step outside to a nicely sized rear deck overlooking the backyard, perfect for relaxing, grilling, or entertaining. This home is ready for its next chapter and offers a wonderful opportunity for a buyer to add personal touches, make updates, and truly make it their own. With a practical floor plan and plenty of potential, 4664 Hathaway Drive is ready to be refreshed and enjoyed for years to come!

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$259,900
3bedrooms
2bathrooms
land 0.1ha

By Bluegrass Sotheby's International Realty

Nearby
50

House with garden and terrace Lexington (United States)

Elegant, refined, and exceptionally well-located, this beautiful Colonial residence is ideally situated in Lexington's highly coveted Turkeyfoot neighborhood. Offering 4 bedrooms and 4.5 baths, including his and her primary baths. This impressive home combines timeless architectural character with modern comfort, thoughtful updates, and the convenience of an elevator serving the home. The gracious open-concept design creates an effortless flow between the living spaces, making the home equally suited for sophisticated entertaining and relaxed everyday living. Numerous upgrades enhance the home's appeal, while the finished basement provides expansive additional living space ideal for a media room, recreation area, home office, or fitness space. A true highlight is the expansive wraparound screened porch—a wonderful retreat for morning coffee, leisurely afternoons, or relaxing evenings with family and friends. Overlooking the large lot and backing directly to Ecton Park, the porch creates a seamless connection to the outdoors while offering a peaceful and private setting. The home's exceptional location places you just minutes from the University of Kentucky, Commonwealth Stadium, and downtown Lexington, while the charming shops along Romany Road are within easy walking distance. The highly anticipated Publix, scheduled to open in 2027, will add another level of convenience to this already premier location. A distinctive blend of timeless elegance, generous living space, exceptional outdoor living, and an unbeatable location, this remarkable Turkeyfoot residence offers a rare opportunity to enjoy one of Lexington's most desirable neighborhoods.

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$1,395,000
4bedrooms
5bathrooms
land 0.2ha

By Bluegrass Sotheby's International Realty

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