Winchester Real Estate | Winchester Homes with a Pool for Sale

Enjoy Southern living in this charming Cape Cod-style home featuring three bedrooms, two full bathrooms, and a dedicated office. The main level includes the primary bedroom, office, full bathroom, laundry room, and a kitchen with a breakfast bar and dining area. Upstairs are two additional bedrooms and a second full bathroom. A spacious, level yard provides plenty of room for entertainment. Come enjoy today.

307 Mcdowell Dr, Winchester

$4,895,000

3 Beds ⋅ 4 Baths ⋅ 26028325 MLS

A Rare 77 ± acre Kentucky Estate with a new custom home & equestrian facilities offers privacy, commanding views, and the natural beauty of Kentucky's renowned horse country that truly define this exceptional recreational estate. Offering an extraordinary combination of luxury living, 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 the beautiful stocked ponds, leading to the highest point of the estate where an impressive custom stone residence and equestrian facility command panoramic views. The recently completed 5,800 ± square-foot custom 3 BR/3.5 BA stone manor home combines elegant finishes with a warm 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 2 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 which includes approx 1,000 sf of living quarters featuring 1 bedroom and 1½ baths. The clear-span main building is designed for extraordinary versatility- capable of accommodating aircraft, collector cars, RVs, and/ or 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 wood shop with additional storage extends along the edge of the building. The lower level incorporates a substantial barn area with 4 horse stalls, tack room, hay storage, and tractor/mower storage, with convenient access to the 10-acre fenced field for horse turnout. Whether envisioned as a private equestrian estate, recreational compound, luxury country residence or a combination of all three, this property offers a rare level of amenities and versatility in one of Central Kentucky's most desirable settings- it truly must be seen to be appreciated.

5825 Combs Ferry Rd, Winchester

$2,299,000

5 Beds ⋅ 4 Baths ⋅ 26028074 MLS

Experience exceptional craftsmanship, privacy and resort-style living on over 12 acres in the highly desired Combs Ferry area of Clark County. Quietly tucked away yet conveniently located just 15 minutes from Hamburg in Lexington, as well as Winchester and Richmond, this extraordinary custom home was built in 2022 and offers 6,284 finished square feet, plus an additional 1,545 square feet of unfinished space ready for the next owner to customize. From the moment you enter, the quality and attention to detail are unmistakable. Andersen 400 Series windows and doors, decorative ceilings, custom trim and built-ins, engineered hardwood flooring, quartz countertops and designer lighting are featured throughout. The spacious kitchen is a true centerpiece, showcasing custom cabinetry, soft-close doors and drawers, under-cabinet lighting, a hidden walk-in pantry, double ovens, built-in microwave and a 5-burner gas range with built-in Thermador appliances. The main-level primary suite is a private retreat, complete with decorative beams, a stacked-stone gas fireplace, double vanities, soaking tub, expansive walk-in closet and an oversized tiled pass-through shower featuring dual shower heads and a centered rain head. Large walk-in closets accompany every bedroom, providing exceptional storage throughout. The finished lower level expands the possibilities with a home gym, dedicated movie theater with projector and equipment, home office/bonus room, wet bar with granite countertops, wine and beverage refrigerators and dishwasher, plus an additional bedroom with egress window, full bathroom, and walk-in closet. Multiple unfinished areas and the additional 1,545 square feet provide tremendous potential for future customization. Step outside and discover your own private entertainment destination. The 45,000-gallon oversized heated chlorine pool features a tanning ledge, deep-end swim ledge, fountain, LED lighting and energy-efficient variable-speed pump. Enjoy evenings around the custom outdoor fireplace, with the convenience of a dedicated outdoor bathroom. The property also includes a basketball court, shooting range, and detached garage with concrete floors and double garage bays. Additional thoughtful features include a formal dining room with custom moldings, laundry room with built-in cabinetry, mudroom/drop zone with built-ins and cubbies, spray foam insulation, three all-electric HVAC systems, and two 60-gallon water heaters. This is far more than a home; it is a custom-built private estate designed for everyday luxury, entertaining, recreation and relaxation, with room to make it uniquely your own. The combination of acreage, exceptional construction, extensive amenities and convenient location is truly rare. Schedule your private showing today and experience this breathtaking property firsthand. Seller is a licensed Realtor in Kentucky.

5039 Combs Ferry Rd, Winchester

$359,900

4 Beds ⋅ 2 Baths ⋅ 26027372 MLS

Built in 1913 and located two blocks from Main Street, 107 S Burns Avenue retains its original interior detail: coffered ceilings, cherry wood wainscoting, hardwood floors, leaded diamond-pane windows, brick fireplaces with their original mantels, and built-ins throughout. The home offers four bedrooms, two full baths, and 2,352 square feet. The upper level has been fully renovated and includes a private fourth bedroom, full bath, built-in workspace, generous knee-wall storage, and a dedicated heating and cooling system. In the kitchen, custom cabinetry complements an original double-drainboard cast-iron sink, while the main-level bath retains a beautifully reglazed original clawfoot tub. Outdoors, an eight-foot privacy fence creates a secluded backyard setting with an above-ground pool and ample space for relaxing and entertaining. An original carriage-door garage adds another layer of historic character, complemented by off-street parking for up to three vehicles. Located just two blocks from Main Street, the home offers convenient access to downtown Winchester's locally owned restaurants, boutiques, theater, festivals, and community events. College Park and the public library are also just a few blocks away.

107 S Burns Ave, Winchester

$1,125,000

3 Beds ⋅ 4 Baths ⋅ 26026878 MLS

Tucked away behind private gates on 28 beautiful acres, this one-of-a-kind cabin offers the perfect blend of privacy, luxury, and country living. Step inside to a stunning open-concept living, dining, and kitchen area designed for gathering and entertaining. The kitchen is a showstopper with custom cabinetry, quartz countertops, a waterfall island, top-of-the-line appliances, and a spacious walk-in pantry. Off the kitchen on the right wing of the house there is a mudroom area with half bathroom, followed by the primary suite. The main-level primary suite is a true retreat, very spacious bedroom area with a private sunroom and direct access to the patio and in-ground pool, walk-in closet and laundry closet. The bathroom features a soaking tub and a tiled walk-in shower. Upstairs, you'll find an additional spacious bedroom with built-in bunk beds, a walk-in closet, and full bath. The left wing of the home provides ideal in-law or guest quarters featuring its own kitchen, open concept living and bedroom area with fireplace, walk-in closet, full bath with walk-in shower, and private exterior entrance. Outside is where this property truly sets itself apart. Enjoy your own private oasis with an in-ground pool surrounded by picturesque acreage. The backyard also includes a "she shed" currently used as a workout room, chicken coop, run-in shed, and 30x33 detached garage. This property features an AKC-inspected kennel facility with 14 indoor/outdoor runs, an office, a grooming area, a bathing area, an open work space, half bathroom and a fenced exercise area. Another 6-hole kennel with overhangs. The remaining property features 7 paddocks, 5 run-in sheds, multiple fenced pastures with run-in sheds and water. Bring the horses, cows, dogs—and even the in-laws! This is an animal lover's dream with room to live, work, play, and enjoy the peace of the countryside, all while being just minutes from I-64 and approximately 24 minutes from Downtown Lexington. The possibilities for this property are endless, and it is a truly special property that has to be experienced in person!

2100 Irvine Rd Unit 40391, Winchester

$375,000

4 Beds ⋅ 2 Baths ⋅ 26026446 MLS

Welcome to your new home. Move-in ready inside and out, this 4-bedroom, 2-full-bath home offers comfortable living, plenty of finished space, and a backyard that truly feels like your own private retreat! The home has been well cared for and thoughtfully updated, including new flooring throughout the entire finished portion of the basement, new toilets, and a new dishwasher and stove. Step outside and you'll quickly see what makes this property special. The in-ground pool and surrounding outdoor living space are an absolute dream, with extensive improvements completed to make it ready for years of enjoyment. All-new concrete was installed around the pool in 2025, along with a new pool liner and gas pool heater, plus a newer pool pump. A new privacy fence installed in 2023 creates a secluded setting, while the gazebo—complete with electricity—provides the perfect spot to relax, entertain, or spend summer evenings by the pool. The improvements continue with a brand-new back porch completed in May 2026 and a new concrete driveway in 2026, adding even more value and curb appeal. Whether you're entertaining friends around the pool, enjoying a quiet evening under the gazebo, or taking advantage of the additional finished basement space, this home offers a lifestyle that's hard to duplicate. Move in, unpack, and start enjoying it from day one!

609 W Barlow Dr, Winchester

$390,000

4 Beds ⋅ 1 Baths ⋅ 26025300 MLS

7353 Ironworks Road and 3015 Pilot View Road are deeded separate but being sold together. 7353 Ironworks includes the house and barn and 3.348 acres. 3015 Pilot View is the adjacent lot and has 3.38 acres. Total acreage is 6.728. There are 2 bedrooms upstairs that need cosmetic work. The historic barn is large, has electric and needs some repair. There is plenty of space to build your dream home. Plenty of road frontage on Ironworks and Pilot View. The lots are mostly level, some sloping and mainly cleared. Lots of things to like about this property! Transform this wonderful old farmhouse or plenty of room to build your dream home. Selling as is, Inspections welcome.

7353 Ironworks Rd, Winchester

$629,000

5 Beds ⋅ 4 Baths ⋅ 26023607 MLS

Space, craftsmanship, and versatility come together in this stunning all-brick 1.5-story home with a finished basement, located in the desirable Mallard Place subdivision! Designed to maximize every square foot, this home offers three levels of comfortable and flexible living space. The main level welcomes you with beautiful hardwood floors, vaulted ceilings, and a cozy gas fireplace. The spacious primary suite features an en suite bath, while two additional bedrooms are connected by a convenient Jack-and-Jill bathroom. A formal dining room and eat-in kitchen provide plenty of space for everyday living and entertaining. The basement is made for gathering, featuring an entertainment area complete with a bar, along with a bonus room and plenty of storage. Upstairs, you'll find even more flexible space, including a loft-style bedroom, two additional bonus rooms that could be used as bedrooms, a family room, and additional attic storage. Step outside to enjoy the backyard retreat, complete with an in-ground pool—perfect for relaxing and entertaining! With so much space and so many possibilities inside and out, this home is one you truly need to see in person. Schedule your private showing today!

104 Teal Ln, Winchester

$488,000

4 Beds ⋅ 3 Baths ⋅ 26019848 MLS

Discover the perfect blend of privacy, comfort, and country elegance on nearly 6 acres of beautiful Kentucky land. This stunning 4 bedroom, 2.5 bath home offers the lifestyle buyers dream of — complete with a sparkling inground pool, generous outdoor space, and thoughtful updates throughout. Set in a peaceful rural setting yet conveniently located just 8 minutes from the Winchester Bypass and 15 minutes from Mt. Sterling, this property delivers the best of both worlds: tranquility and accessibility. From the inviting living spaces to the expansive grounds ideal for relaxing, entertaining, or simply enjoying the view, this home is truly one of a kind. Opportunities like this don't come often — this one will move fast. Don't miss your chance. Call today to schedule your private showing.

1780 Stoner-Ephesus Rd, Winchester

$785,000

5 Beds ⋅ 3 Baths ⋅ 26019610 MLS

Escape to the peace and privacy of country living with this spacious brick one-and-a-half story home situated on just over 5 acres. With plenty of room to spread out, the main level offers a welcoming foyer, formal dining room, living room with a wood-burning fireplace, kitchen featuring granite countertops, tile backsplash, breakfast nook, and laundry room, along with the primary suite, three additional bedrooms, and another full bath. The primary suite is a true retreat with exposed wood beams, a sitting area, tiled shower, and marble vanity. Upstairs you'll find a fifth bedroom, while the fully finished basement adds even more flexible living space with a second living area, kitchenette, bonus rooms, half bath, and radon mitigation system already in place. Throughout the home you'll find beautiful shiplap accents and a mix of hardwood, tile, vinyl, and carpet flooring. Step outside to enjoy the covered patio, pergola, fire pit, swing, above-ground pool with deck, and playset, all perfect for entertaining or relaxing. The attached two-car garage is complemented by an additional detached garage with its own upstairs space and separate electric meter, offering endless possibilities for a workshop, storage, or future expansion. Thoughtfully updated over the years and offering the perfect mix of space, comfort, and country charm, this property is ready to welcome you home.

217 Wades Mill Rd, Winchester

$219,900

3 Beds ⋅ 2 Baths ⋅ 26018492 MLS

*NEW ROOF!* Welcome home to this well-established 3-bedroom, 2-bath coveted brick ranch offering easy one-level ranch living in a wonderful location close to all the conveniences that Winchester has to offer, including a community pool and gym just a couple turns away. The spacious open family room features a gas fireplace and flows into the spacious kitchen, featuring bamboo wood flooring, a large granite island, newer stainless steel appliances, and a gas range. Step outside and enjoy your own Aurora above-ground pool perfect for family entertaining. The partially fenced backyard also includes an oversized storage/tool shed, providing plenty of room for hobbies and extra storage. Enjoy peace of mind with major updates including a newer HVAC system, water heater, Window World windows (approximately 5 years old), and a new roof with a 5-year warranty. This solidly built home is full of potential and has served the current owners well as they transition to their next chapter in life. It is ready and waiting for a new family to come and breathe life and make it a home once again.

528 Estes Dr, Winchester

$1,595,000

3 Beds ⋅ 3 Baths ⋅ 26011538 MLS

NEW PRICE!!! Not sure what you are looking for, but see if this property checks enough boxes for you. This beautiful 33± acre estate offers the perfect blend of country charm, modern comfort, and endless opportunity. The stately historical home, built in 1919, offers a rare opportunity to own a true piece of Kentucky history . Enjoy stunning mountain views — perched at one of the highest points in Clark County, where you can see the panoramic views stretching all the way to the dormitories at EKU in Richmond and the mountains near Berea, KY. Relax by the newly lined in-ground pool with a new cover, and unwind in the hot tub while taking in the beautiful sunrise and sunset views — perfect for family gatherings or quiet evenings under the stars. The property features a two-level barn with horse stalls, a tack room, and a spacious open arena — ideal for equestrian enthusiasts. The upper level of the barn provides versatile space for auto storage or a workshop, while the fenced pastures and horse ring make it ready for boarding or training horses. This property also includes a stocked pond, adding to the tranquil landscape, and 2 gated driveways with a security system for peace of mind. The land features mature trees, including fig, pear, and apple. This is the first property on Colby Road out of Winchester with agricultural zoning, a very private estate, and the first time in 40 years this remarkable property has been for sale. Conveniently located just one mile to Kroger, Lowe's, and Walmart, and approximately 20 min. from Man O War via Todds Rd. Lexington. This property offers both peaceful seclusion and easy access to amenities. With potential for income from horse boarding and a rental home on the property, this exceptional farm is more than a home- it's a lifestyle, an investment, and a place to create lasting memories for generations to come.

3166 Colby Rd, Winchester

$2,750,000

8 Beds ⋅ 8 Baths ⋅ 26009631 MLS

Welcome to 4664 Lexington Road—a magnificent private estate on 35 rolling acres of pristine Kentucky countryside that feels worlds away, yet sits just minutes from the charm of Winchester and the vibrancy of Lexington. A stately stone entry welcomes you down a graceful, winding driveway to a sweeping circular drive, leading to a grand 13,000+ square-foot residence built in 1997 with timeless elegance and generous proportions. Inside, the 8-bedroom, 7.5-bath home offers expansive living spaces bathed in natural light, refined finishes, and classic architectural details—perfect for both intimate family moments and large-scale entertaining. A fully finished basement adds exceptional flexibility for recreation, additional living quarters, or extended gatherings. Outdoors, the property continues to impress with sweeping valley views, open pastures and mature wooded areas. Enjoy the private pool as a true retreat. Additionally, the property is complemented by a classic tobacco barn and additional shop space ideal for storage, hobbies, equestrian use, or agricultural pursuits. Zoned PD (Planned Development), this estate presents rare versatility and significant upside—whether envisioned as a forever family home, a multi-generational retreat, a private equestrian estate, or a thoughtfully planned development opportunity. Privacy is unparalleled, yet convenience is effortless, with easy access to world-class horse farms, bourbon trails, and the cultural amenities of the Bluegrass Region. This is more than a home—it's a legacy property where luxury living, natural beauty, and gracious Kentucky living come together in perfect harmony, delivering exceptional value and endless possibilities.

4664 Lexington Rd, Winchester

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