Winchester KY Real Estate & Homes for Sale

Welcome to this stunning 5-bedroom, 4.5-bathroom home located in the prestigious Walnut Grove Estates. From its timeless architecture featuring turret details and arched windows to its thoughtfully designed interior, this residence offers the perfect balance of luxury and functionality. The main floor boasts a spacious primary suite with a tray ceiling, a turret-style sitting area framed by large windows, and a spa-inspired ensuite with a separate soaking tub, tiled shower, double sinks, and a beautifully updated walk-in closet. The two-story great room with a striking stone fireplace invites you in, while the gourmet kitchen impresses with granite countertops, stainless steel appliances, a large island, an updated walk-in pantry, and an adjoining hearth room with built-in shelving and a cozy fireplace. A formal dining room, powder room and laundry room complete the first floor. Upstairs, you'll find three additional bedrooms, one with its own ensuite bath and two sharing a large Jack-and-Jill-style bathroom. The finished walk-out basement offers endless possibilities with a fifth bedroom featuring an ensuite bath, two versatile bonus rooms for hobbies, a gym, or a media room, and abundant storage space. Outdoor living is just as exceptional, with a concrete patio overlooking lush landscaping, a black iron fence, irrigation system, and peaceful views of green space and a nearby pond. The 3-car garage is upgraded with epoxy floors, new cabinetry, ample storage, and a mini-split HVAC unit. Make sure to ask for a list of improvements featuring things like a state-of-the-art Barney Miller whole-home electronics system and a Bates security system with cameras. This home is the epitome of elegance and modern convenience, offering everything you need for luxury living in one of the area's most sought-after neighborhoods.

Welcome to 3501 Trinidad Court in Greenbrier Estates, a grand 7,509 square-foot residence on a 1.42-acre corner lot directly across from the Greenbrier Golf Country Club. This impressive property features 7 bedrooms, 9 bathrooms, a huge library off the right wing, and a golf course pathway for golf carts. The property is a little dated but offers a very large kitchen, seven fireplaces, an attached three-car garage, and a circular driveway with a grand entrance. The primary bedroom and bathroom span the entire right side of the house above the library. There's also a hidden spiral staircase that goes from the basement's mechanics room up to the first floor, into a closet, and then into the back of a closet in the primary bedroom. This REO foreclosure offers a unique opportunity for someone to come in and put their own design taste on it.

BACK ON THE MARKET AT NO FAULT OF THE PROPERTY. Versatile and Efficient. Well thought out horse farm with completely renovated barndominium in steel frame barn with 16 stalls and attached indoor arena. Small secondary barn with 3 additional stalls. Recently built equipment shed, hay hoop barn and run-in sheds. The freshly updated barn apartment was gutted to the studs and features dramatic vaulted ceilings, open concept floorplan with 2 bedrooms and 2 bathrooms. The primary bedroom has a massive closet and private balcony overlooking pastures. Enjoy working your horses in the indoor arena, the grass jump field or the trails through the woods and fields. There are several beautiful home sites if you would desire building a main home. PRICED BELOW RECENT APPRAISAL dividing off 5 acre parcel. Subject to approval from P&Z. Conveniently located 35 minutes to KHP or the equine hospitals, 45 minutes to Keeneland and only 15 minutes to Paris, less than 20 to Winchester or Mount Sterling.

This 3 bed, 1 bath home has solid bones and a functional layout - it just needs flooring updates and general TLC to shine again. Perfect light-rehab opportunity for a rental or starter flip. Great upside with minimal heavy work. Property sold AS-IS.

Discover a rare opportunity in Fayette County: a spacious, two-story mansion set on 9 private acres, offering both luxury and privacy while sitting vacant and ready for a new vision. This home features five bedrooms and six bathrooms, giving you plenty of room for family, guests, or future customization. One of the standout features is the basement level, which feels more like a private resort. You'll find an indoor pool, complete with its own fountain, creating a peaceful, spa-like atmosphere no matter the season. There's also a jacuzzi for unwinding, and a 12-seat theater room perfect for movie nights!

New listing in desireable Brookhaven- Lansdowne neighborhood. Classic all brick ranch with walkout basement - a great layout for one level convenience (potential to move laundry upstairs) Expansive floor plan with 4 bedrooms and 2 full bathrooms upstairs, large eat in kitchen on a .32 acre level lot. Gorgeous landscaping and plenty of parking. Basement offers two living areas, an office/flex room. laundry, and 1.5 bathrooms. Ideal for guests, teens or home office. So much room - with room to expand. Rare floored attic via permanent stairs for storage or potential future living space. Sought after location close to new circle rd, tates creek and nicholasville rd rich with shopping, dining and navigation. Established neighborhood with mature trees and sidewalks

Discover this hidden gem tucked away on 10 lush acres in Madison County. This beautifully remodeled brick ranch offers of refined living space with two bedrooms, two baths, and an unfinished basement for future expansion. Set behind a gated entrance on 10 pristine acres, the fully fenced property features board fencing, with three horse paddocks. The 60 40 barn includes six stalls - one designed as a foaling stall - along with a wash bay, shavings area, and 12-foot lean-tos on both sides. The large Gravel parking lots allows parking for multiple vehicles, and trailers. The home was completely updated in 2022 with a new HVAC, Roof, Electrical Panel, Water Heater, Flooring and much more. Don't mis this modern horse property just 20 minutes from Lexington.

Welcome home to this immaculately maintained Lexington gem, located just 2.5 miles from the University of Kentucky campus! Offering remarkable flexibility and charm, this property is ideal for both an owner-occupant or as a fantastic investment opportunity. Step inside to warm hardwood floors and a bright, inviting layout. The home features 4 true bedrooms, plus an additional room currently used as a 5th bedroom (not to ANSI standards), giving you plenty of space for guests, a home office, or hobbies. The updated appliances and well-kept interior make this home truly move-in ready. Enjoy outdoor living with a spacious deck, a covered patio, and a fully fenced yard - perfect for entertaining, relaxing, or letting pets play freely. A detached 2-car garage adds convenience, storage, and functionality. With no HOA, you'll have the freedom to use your property your way.

Welcome to this inviting 4-bedroom, 3-full-bath home nestled in the desirable Hidden Springs subdivision of southwest Lexington. Built in 1992, this well-designed well-maintained home is approx. 1,800 sq ft and sits on a gorgeous lot offering great outdoor space. On the main level you'll find an updated kitchen with solid surface countertops; ready for everyday cooking or entertaining. Off the Kitchen is a Cozy living room with fireplace. The dining area is also off the kitchen and has an open feel for nice comfortable living. There are also 3 spacious bedrooms, 2 baths and laundry on the main level. A unique feature of this home is the ''suite-style'' lower level with bedroom, office area, full bath and walk-out access: ideal as a guest space, home office, or teenager retreat On the lower level, in addition to the Bedroom/Office Suite is an Attached two-car garage with rear entry. There is plenty of driveway parking and at 28 ft deep, there is also great garage storage. Outside you'll find a large tree-lined back yard, the lot feels like a serene suburban setting but still being conveniently close to all the amenities. The yard is partially fenced, has an upper-level deck and a lower-level patio. It's an inviting, peaceful retreat. This property offers the perfect blend of thoughtful living space and prime location. Whether you're raising a family, working from home, or looking for comfortable suburban living with easy access to Lexington's amenities, 1144 Wood Ridge Rd is well-suited for all of the above. From bedrooms upstairs to a versatile lower-level suite, it adapts to nearly any lifestyle. For more information, photos, or to schedule a viewing, please let me know and I'd be happy to assist.

Charming 4 bedroom, 2.5 bathroom home in The Vineyards Subdivision with plenty of possibilities. This property offers a 2 car garage with space for parking, as well as storage for tools. The primary level offers a Family Room with new flooring, tall vaulted ceilings, and a gas fireplace. The Kitchen area includes 2 pantries, a breakfast bar area, stainless steel appliances, and lots of storage. The laundry area is conveniently located on the second level with all of the bedrooms. The spacious primary bedroom offers a bathroom with a walk-in closet and a soaking tub. Outside, enjoy the fenced-in backyard that offers a cozy firepit.

Maintenance free condo living situated within a 55+ community that offers a clubhouse & pool. Association fee is $350/monthly and includes groundskeeping, snow and ice removal, trash, water and sewer as well as master insurance. Two bedrooms on first floor with upper level offering second primary bedroom suite. All main living on first floor with no steps and direct entry from the garage. Vaulted, open living area with gas log fireplace and plenty of natural light. Nice sized dining area, kitchen bar and eat-in-kitchen. Primary bedroom with walk-in shower. Laundry room and tons of storage space in this home. Fenced courtyard for outdoor viewing and relaxation. Two-car garage has epoxy coated flooring. Convenient location with easy access to shopping, restaurants and mor

Spacious 4-Bedroom, 2.5-Bath Home in Keene Crossing! Built in 2007 and fully renovated last year, this 2-story home offers 2,640 sq. ft. of above-grade living space. The Primary Bedroom (PBR) features a private ensuite and generous closet space. Open floor plan with bright living area, formal dining, and a modern kitchen. Conveniently located near schools, shopping, and parks. Don't miss out on a great opportunity - schedule your private showing today! This property is also available for rent at $2,650/month

Investor special! This 3-bedroom, 1-bath home sits on a full acre of land with tons of potential. Whether you're looking to flip, rent, or hold for future appreciation, this property offers great upside. Solid structure and layout ready for your updates - add value with cosmetic improvements or expansion. Convenient location with plenty of room for additional units, garage, or outdoor amenities. Opportunities like this don't last long - bring your vision and make this your next profitable project!

Charming 1.5-story home at 416 Bethlehem Rd in Waco, KY. This property offers great potential at an affordable price. The layout includes a cozy main living area, an eat-in kitchen, and flexible bedrooms, plus an upper-level space perfect for an office or extra room. The home could use some TLC, making it ideal for buyers wanting to add value with cosmetic updates. Enjoy a spacious yard and peaceful country setting. A solid opportunity for first-time buyers or investors.

Notably featured in KY Homes and Gardens Magazine, this September/October issue, Estill Oaks is a thriving Short Term Rental and rustic retreat on a secluded 40 acres with long range views. Featuring a 3 br/2.5 bath main house with a 4 br/2 bath bunkhouse (sleeps 16), take a look at the reclaimed wood finishes and superior design. This property offers a unique investment in the Red River Gorge area with multiple additional build sites and a matching reclaimed wood barn that can be marketed for weddings and events. In the existing home, enjoy smart home features like WiFi, indoor/outdoor speakers, adjustable lighting, hot tub, and fire pit. With stunning views, luxurious touches, and hiking/ UTV trails, Estill Oaks is an ideal getaway for up to 16 guests. Additional acreage available.

PRICE IMPROVEMENT!!!! Priced below comps! Stunning 4-Bedroom Home on 1.288 Acres - Loaded with Upgrades! Welcome to your dream home, where comfort, style, and functionality come together flawlessly. This expansive 4-bedroom, 3.5-bath residence offers 4,347 square feet of beautifully finished living space. So many upgrades to check out like the new Bosch refrigerator, Brand new roof 9/2023, sewage pump replaced in 2020 and just inspected in 2023, 3 zone HVAC in 2017, replaced interior doors with 2 panel doors, two new water heaters 2020, Premier garage professionally installed cabinetry in garage and added beautiful coated floor, new garbage disposal 2020, all new gutters, soffit and gutter guards 2/2024, remodeled mud room, driveway was torn out and replaced, and more, Step through the front door into an open foyer and you will view a fabulous formal dining room making a statement with it's exquisite picture frame woodwork and abundance of natural light. The great room, anchored by a cozy natural gas fireplace, invites gathering and relaxation. But wait until you experience the beautiful sunroom complete with a warm fireplace and built-in bar. The chef's kitchen is truly exceptional, showcasing granite countertops, premium JennAir appliances, double ovens, and a spacious breakfast bar designed to foster connection and casual dining. The primary suite is a serene retreat designed for relaxation. On the second floor there is a guest suite complete with it's own ensuite bathroom and two additional bedrooms with closets you will need to see to believe! Car enthusiasts and hobbyists will appreciate the impressive 1500 square foot, 3-car dream garage, fully equipped with built-in cabinetry and plenty of room for tools, toys, or projects. This exceptional home is a rare find, offering luxurious space, thoughtful design, and unbeatable indoor-outdoor living and all in a private, spacious setting.

Cozy cabin located just minutes from the historic Nada Tunnel and the Red River Gorge. This inviting property offers easy year-round access, no steep hills or difficult driveway to climb. The cabin features an open living area, kitchen, and a full bathroom on the main level. A loft area provides additional sleeping space but is non-conforming and not counted as a bedroom. Enjoy the peaceful wooded setting from the outdoor hot tub or gather around the fire pit under the stars. The property includes a nice deck, level parking, and simple maintenance landscaping. Ideal for a personal getaway or investment property, this cabin combines rustic charm with modern convenience in one of Kentucky's most sought-after outdoor recreation area!

260 Gleneagles Way w/ over 3600 finished sqft, 5 bedrooms, 3.5 baths, and located in a quiet Versailles neighborhood is a must see! The home itself features new carpet throughout and fresh paint in most rooms making everything feel clean and ready. A new deck gives you a solid outdoor space for meals, gatherings, or quiet evenings. The roof is only a couple of years old, the water heater is newer, and the main-level heating coil has been replaced, the kinds of updates that let you settle in without adding projects to your list. Ceiling height plays a big role here. The entry and family room rise over 10 ft, creating a feeling of openness the moment you walk in. The dining room gets its own identity with a dropped tray ceiling and columns while still staying connected to the living space The kitchen links to a butler's pantry offering extra storage and an effortless flow when you're cooking or hosting. A bay window in the breakfast area brings in steady morning light. The utility/mudroom combination includes a built-in folding counter and enough room to stay organized. The primary bedroom suite feels like a calm space with its deep tray ceiling, large closet, soaking tub and a separate shower. The additional upstairs bedroom is oversized and flexible enough for guests, work, or playroom. Downstairs, the walkout basement opens up the home in a big way. It includes a full living area, a bedroom, a full bath, and a bar area with a sink and fridge that makes the space easy to use for gatherings or long-term guests. There's also a large unfinished storage room and another room that works well as a home gym or focused workspace. The basement steps straight out to the backyard, giving the whole level a natural connection to the outdoors. Huntertown Elementary is about a mile away, and Woodford County Middle and High School are only a few minutes beyond that. Kroger Marketplace sits close enough for quick runs, and you've got other small local options nearby when you don't want a full grocery trip. Parks and green space are easy to reach. Falling Springs Recreation Center offers fields, a pool, and a place to move your body year-round. Owner/Agent. Call today for your private showing!

Welcome home to this beautifully cared-for one-level gem in the heart of Versailles! Offering 4 spacious bedrooms and 2 full baths, this updated ranch blends comfort, convenience, and that welcoming Kentucky charm. Inside, you'll find a bright kitchen, a dedicated dining room for gatherings, and a cozy living room anchored by a fireplace, perfect for winding down after a long day. This home has been loved well, and it shows! Enjoy peace of mind with updates that include a new roof, windows, vinyl, gutters and soffit, garage door, and more! So much of the big work has already been done for you. Sitting proudly on a corner lot, the outdoor space is ideal for play, pets, or weekend relaxing...and yes, the swing set stays! Commuters and travelers will especially love the location, just a quick drive to Blue Grass Airport in Lexington, making trips, work, and weekend getaways easier than ever. If you're looking for stylish, easy, one-level living close to everything, this Versailles beauty is ready to welcome you home!

Motivated Seller !!!! Here is your chance to have your very own cabin in the Red River Gorge. Candlelight Cabin is an established short-term rental (rental income for 2024 & 2025 available upon request) or a great private retreat in the heart of the Gorge. Candlelight is perfect for outdoor enthusiasts with wrap around decking, multi lounging areas and a hot tub with sunrise views. This turnkey property has 2 bedrooms with on suites, extra half bath with laundry, furnished kitchen and a family room with vaulted ceiling and lots of windows to enjoy nature. Located in a prime cabin community close to the parkway and everything the Gorge has to offer. Own a cabin in one of the top 20 areas in the country and top 3 in the state for vacation rentals.

Stop Right Here! This Nice home Features 1600 sf of living Area on a Level lot with an In-Ground Pool Close to everything! Features include an Entry Foyer & a Large Family Room for family Gatherings. Off the Rear of the Family Room is a Spacious Kitchen with the dining Area off the Side and another area with Woodburning Fireplace. Garage is located off the Kitchen Area. Off the Rear of the Dining area is a Large Sunroom overlooking the In-Ground Pool and Large Rear Yard. Down the hallway from the Family Room is the Primary Bedroom with Primary Bath, 2 additional Bedrooms and a 2nd Full Bath. The exterior has a large storage building, a privacy fenced rear yard and a Covered Front Porch. All situated close to amenities and shopping. Call NOW for your Private Viewing!