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$316,900
3 Beds 3 Baths 26008021 MLS
Search no more your dream home just hit the market! You will fall in love with this one as soon as you walk through the front door. Beautiful open concept, very modern new home just built in 2022. You're going to love the open kitchen and living room area with the large kitchen island, beautiful stainless steel appliances and granite countertops. Primary bedroom on the first floor with a full bath and nice walk in closet. Picture hosting your social events on the expansive two-level decks located at the back of your new home. If that is not enough this home is perfectly located within waking distance to Kroger & Walmart, shopping and dining. Come be the first to see this one or your likely to regret it. This home has never flooded but as of 2025 it does require flood insurance. The current owner has the flood insuance through ( The Hartford ) insurance company at a cost of $100 a month. Owner is offering to pay $1200 for the new owners first year of flood insurance.

200 Dubuy 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

$355,000
1 Beds 2 Baths 26012322 MLS
Home listed as one bedroom while unofficially has 3 but 2 of them are interior rooms without windows. ( Owners Now Offering to pay up to $5,000 in closing cost and pre-paids on behalf of buyers). Tired of the honking horns , congested traffic, sirens of town living and dreaming of country living, your own slice of paradise? Maybe raising your own garden , owning chickens , goats, horses , whatever you always dreamed of. Maybe just kicking back on the wrap around porch watching the chickens peck. This really is an amazing property and you will fall in love with all the bells and whistles like the beautiful soaking tub, 2 walk in showers, huge kitchen island, large primary bedroom and bath, stainless steel appliances. It practically a new house , the front portion of the house where the living room , hall, primary bedroom were all built new in 2020 . All the wiring , plumbing , insulation, flooring , drywall has been replaced since 2020. Home is also very conveniently placed just minutes from exit 10 on the Mountain Parkway between, Winchester and Clay City. Dont let anyone beat you to it , this is a real jewel. Porch swing belonged to owners great grandmother and does not convey.

3359 Trapp-Goffs Corner Rd, Winchester

$550,000
3 Beds 3 Baths 24025578 MLS
Welcome Home to the Winchester Floor Plan by CP Builders. This elegant ranch home features all-brick construction, a welcoming front porch, and a two-car garage. Step inside and be greeted by soaring 9-foot ceilings and a spacious open floor plan. The split bedroom design offers privacy and comfort, with a luxurious primary suite boasting an ensuite bathroom and a walk-in closet. Enjoy easy maintenance with luxury vinyl plank flooring throughout the home. The heart of the home is the spacious great room, complete with a cozy gas log fireplace, perfect for gathering with loved ones. The well-appointed kitchen features a large island, ideal for both cooking and entertaining. Additional features on the first floor include a full bathroom, a convenient half bath, and a separate laundry room for added convenience. Step outside onto the back patio and enjoy the fresh air and sunshine. Let's build your dream home and make the Winchester Floor Plan yours!

107 Bella Shae Way, Winchester

$2,999,000
6 Beds 5 Baths 25507353 MLS
Some properties are special simply because of the story behind them. This 150 acre farm with 3,168 feet of road frontage in Winchester has been cared for by the same family since 1803, and it's now being offered for sale for the very first time. The land is classic Kentucky countryside, rolling pastures, peaceful water, and wide open views in every direction. Four ponds and a gently flowing creek bring both beauty and function to the farm, while four barns and two storage sheds make it ready for cattle, horses, or anyone wanting a true working farm. There are two homes on the property, offering flexibility for extended family, guests, or farm operations. Whether you dream of continuing its farming legacy, creating a private retreat, or investing in a truly special piece of Kentucky land, this is the kind of place that rarely becomes available. Opportunities like this don't come around often. This farm has been part of one family's story for over two centuries, now it's ready for its next chapter.

3049 Ironworks Rd, Winchester

$825,000
3 Beds 3 Baths 24025579 MLS
Welcome Home to the Park Place Floor Plan by CP Builders. This elegant ranch home features all-brick construction and a thoughtfully designed split bedroom layout for maximum privacy. The open floor plan seamlessly connects the living, dining, and kitchen areas, creating a warm and inviting atmosphere. The spacious kitchen is a chef's dream, boasting a large island, a convenient pantry, and a cozy breakfast nook. The luxurious primary suite offers a private retreat with an ensuite bathroom and a walk-in closet. Every bedroom in this home features a walk-in closet, providing ample storage space for the whole family. Additional features on the first floor include a formal dining room, a dedicated study perfect for working from home, a half bath for guests, and an additional full bathroom. This desirable lot also includes an unfinished walkout basement, offering endless possibilities for expansion or customization. Make the Park Place your dream home. Reach out today to schedule a consultation with our experienced team and bring your vision to life.

111 Bella Shae Way, Winchester

$670,000
3 Beds 2 Baths 24025580 MLS
Introducing the Hampton, a beautiful all-brick ranch home. This 3-bedroom, 2-bath split-bedroom design offers both privacy and comfort. The spacious primary suite is a true retreat, featuring a luxurious ensuite with double vanities, a walk-in shower, and dual walk-in closets. The open-concept kitchen and great room are perfect for entertaining, highlighted by a gas log fireplace, a large kitchen island, and a generous walk-in pantry, along with a convenient butler's pantry for added storage and prep space. Nine-foot ceilings and luxury vinyl plank flooring throughout add a touch of elegance, while the separate utility room offers practicality. The additional two bedrooms also include walk-in closets. With a formal dining room, unfinished walkout basement, and a two-car garage, this home combines stunning curb appeal with modern functionality. Come build your dream home in Mallard Cove neighborhood!

113 Bella Shae Way, Winchester

$344,900
4 Beds 3 Baths 26014834 MLS
Updated Price, below Apprisal value...Space, Location, and Great Finishes....4 bedrooms, 2.5 bathrooms, walk in sit down and relax...Dining Room/Living Room or Office welcomes you as you enter from the covered front porch. Guests can use the 1/2 bathroom on the main level...Open Kitchen and Family Room with granite counter tops, breakfast bar, and large pantry making cooking easy, 10 ft ceilings on the mail level offer a more open feel. Upstairs you will find a large laundry room 3 bedrooms a guest bathroom with double vanity! The primary bedroom offers plenty of room, double vanity bathroom, and custom walk-in closet. Outside the yard is fenced with vinyl style fencing, a patio for grilling and 2 car attached garage for your vehicles and storage. This home has all the space and it's priced to sell!

119 Gibson Way, Winchester

$139,900
3 Beds 1 Baths 26007798 MLS
3BR/1BA | Winchester, KY Affordable single-family homes are hard to come by at this price — here's your chance. This cozy 3-bedroom, 1-bath home in Winchester sits on a generous lot with a large backyard, long driveway with plenty of parking, a welcoming covered front porch, and accessible front entry with both steps and a ramp. it's efficient and easy to maintain — and don't let the square footage fool you. A huge walk-in crawl space underneath the home offers exceptional storage that most homes twice the size don't have. The big-ticket items are handled: a brand new roof was installed in 2024, giving you peace of mind for years to come. Currently tenant occupied — ideal for an investor looking for immediate cash flow, or a future owner-occupant planning ahead.

19 3rd St, Winchester

$219,000
3 Beds 2 Baths 26011961 MLS
Remodeled and move-in ready! Conveniently located in downtown Winchester just minutes from Main Street and I-64, this charming home offers the perfect blend of character and modern updates. Major improvements include a near complete replacement of the heating, plumbing, and electrical systems, giving buyers peace of mind for years to come. Inside, you'll find all new flooring throughout, a beautifully updated kitchen featuring stainless steel appliances, a gas range, pantry, and plenty of space for cooking and entertaining. The home offers a primary suite, two additional bedrooms, an additional full bath, and a large utility room with extra storage and functionality. Outside, the 20x24 detached garage with electric is a rare bonus and ideal for carpentry projects, woodworking, hobbies, a workshop, home gym, storage for recreational equipment, or even the perfect space for car enthusiasts and DIYers. Enjoy small-town charm with quick access to shopping, dining, and interstate travel in this thoughtfully updated property ready for its next owner!

14 Cook Ave, Winchester

$795,000
3 Beds 3 Baths 26012252 MLS
**Click on the Virtual Tour section to see the video walk through!** Nestled in the peaceful countryside of Winchester, this charming property on Van Meter Road offers the perfect blend of privacy, comfort, access and room to roam. Set on 13.74 beautiful, fenced acres and located within minutes of I-64, I-75 and the Mountain Parkway, this unique property offers easy access to Lexington, Winchester, Paris, and all of Central Kentucky. Enjoy wide-open spaces, scenic surroundings, and the tranquility of rural living minutes from city amenities. Designed for ease and functionality, the home features convenient one-level living with the added bonus of a finished basement--perfect for extra living space, entertaining, or hobbies. An inviting all-season room provides the ideal spot to relax year-round and a covered front porch overlooking a neighboring pond offers a tranquil place to enjoy your morning coffee or wind down at the end of the day. The kitchen features brand new stainless appliances, with transferrable warranties to the new owner. Did I mention the new roofs and Geothermal HVAC for efficient inside temperature control? Don't miss the first level primary bedroom with a private bathroom and walk in closet. Outside, the property really shines with a detached 3-car garage and a large barn with three stalls, a tack room and two multipurpose rooms. Also there is an additional metal barn with a tool room and three multipurpose rooms. All of these outbuildings have electricity and the wooden barn also has water with a separate fenced area for animals. Whether you're looking for a quiet retreat, a working or hobby farm, or a place to create lasting memories, this property delivers a warm and welcoming atmosphere you'll love coming home to.

6356 Van Meter Rd, Winchester

$359,000
3 Beds 3 Baths 26013780 MLS
Just a 20-second golf cart ride to the Winchester Country Club driving range! Built in 2024 and upgraded throughout, this beautiful 3-bedroom, 2.5-bath home offers modern style, functional living space, and a prime location. The open-concept main level features a spacious living room, kitchen, and dining area designed for both everyday living and entertaining, complete with granite countertops in the kitchen and baths, a deep farmhouse sink, pantry, and stainless appliances. Upstairs, you'll find a generous primary suite with a private bath and walk-in closet, along with two additional bedrooms and a full guest bath. Luxury vinyl plank flooring runs throughout the home, while accent wallpaper in multiple rooms adds warmth, personality, and a custom feel. Recent owner upgrades include a privacy fence, landscape lighting and new shrubs, upgraded stair treads, a concrete sidewalk, and additional attic flooring with a folding attic ladder for convenient storage. The home's attractive exterior combines clean modern lines with shake-style architectural accents, creating great curb appeal. Enjoy nearby golf course views and the convenience of country club living without being directly on the course. Additional features include a 2-car attached garage, crawlspace foundation, and no HOA. With modern construction, quality finishes, and numerous owner-added improvements, this move-in ready home is ready for its next owners to enjoy.

309 Gallahadion Ct, Winchester

$645,000
4 Beds 3 Baths 24025577 MLS
Welcome Home to the Claiborne Floor Plan by CP Builders. This stunning 4-bedroom, 2.5-bathroom home offers a luxurious and spacious living experience. The first floor features a magnificent primary suite complete with a spacious ensuite bathroom, a walk-in closet, and direct access to the backyard. The open floor plan seamlessly connects the living, dining, and kitchen areas, creating a warm and inviting atmosphere. The gourmet kitchen boasts a large island, perfect for entertaining, and a walk-in pantry for ample storage. A cozy fireplace with gas logs adds a touch of warmth and ambiance to the living room. The first floor also includes a dedicated dining room, a study perfect for working from home, a separate laundry room, and a convenient half bath for guests. Upstairs, you'll find three additional generously sized bedrooms and a two full bathrooms, providing ample space for family and guests. The two-story living room creates an impressive and airy feel throughout the home. Experience the joy of building your dream home with CP Builders.

106 Bella Shae Way, Winchester

$399,900
3 Beds 3 Baths 26009517 MLS
Welcome to this beautiful brick ranch on a basement in Hampton Manor. The double front doors open into a large entry way where you will find a living room with large windows allowing for great lighting. The dining room has a fireplace and exposed beams. The kitchen features updated appliances and granite counter tops with an island and a pantry. The sink overlooks the back yard that backs up to a wooded area. The 2 car garage is right off the kitchen allowing for easy accessibility to bring your groceries in. The primary is on the first floor and has an en-suite with a separate sink area from the shower and toilet. There are two other bedrooms and another full bath on the first floor for guests. In the basement you will find the family room and another gas fireplace. There is enough room to have one corner of the basement be an office if needed. You will also find another half bath and utility room on the lower level. The back side of the basement has a large unfinished area with tons of possibilities. The basement family room has walk up/walk out access to the back yard patio where you will find an above ground pool, greenhouse, play set and trampoline (all can be conveyed if needed).

20 Edgewood Dr, 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

$165,000
2 Beds 2 Baths 26001738 MLS
Welcome to this charming river front house. Step out your back door and you are immediately at the river. Open floor plan with a wood burning fireplace. Metal cabinets and epoxy floors on the first level are designed to survive in case of a flood. First floor bedroom with enough room for a King sized bed. Upstairs you will find another bedroom and a half bath. Sip your morning coffee on your back patio area or deck over looking the Kentucky River. There is a large carport for your truck and enough room for a boat as well. The large lot will accommodate a fire pit where you can gather with friends and family. This property is in a flood zone. This property was used as a rental and an air b&b. Make it your own or rent it out, the possibilities are endless.

1494 Amster Grove Rd Rd, Winchester

$785,000
4 Beds 3 Baths 25000149 MLS
Introducing the Highland, an elegant all-brick ranch home offering 4 bedrooms and 2.5 full baths in a thoughtfully designed split-bedroom layout. The spacious primary suite is a true highlight, featuring a luxurious tile shower, separate soaking tub, double vanities, and a large walk-in closet. The open-concept kitchen flows seamlessly into the great room, creating the perfect space for entertaining, with a gas log fireplace, oversized island, and a generous walk-in pantry. This kitchen also features adjacent dining area. The Highland also offers a separate, spacious utility room, and a 2-car attached garage for convenience. Nine-foot ceilings and luxury vinyl plank flooring throughout add to the home's modern appeal. With its stunning double entry doors and stylish curb appeal, the Highland blends comfort, functionality, and timeless design into one perfect home. This desirable lot also includes an unfinished walkout basement, offering endless possibilities for expansion or customization. Experience the perfect blend of style and practicality in the Highland floor plan. Come build the Highland in Mallard Cove with CP Builders!

425 Alexis Way, Winchester

$445,500
3 Beds 3 Baths 26009944 MLS
This is a perfect home for EVERY season.....enjoy multiple, interior gathering spaces and the glow and warmth of either the L R or Dining Room fireplace on the main level or the coziness of the mesmerizing fireplace in the lower level family room during the winter. Watch the backyard come alive with rich and lush vegetation during the Spring from the large, glass walled sun room. For Summer, tons of options await you with the covered front porch, the partially covered back deck or escape to the seclusion of the covered, separate structure at the back. Both the front and back yards are landscaped with many mature trees and perennials that require little attention during Spring, Summer and Fall. Inside, this expansive floor plan packs a lot of punch with a number of interior spaces with an easy flow. The wide entry hall foretells of large room sizes and fresh, neutral paint throughout. The newly renovated kitchen with light wood cabinets is timeless in it's appeal and the adjacent breakfast area is full of natural light. Another handsome fireplace in the next space, with built in shelves could easily function as a D R or Den and the sunroom gives a panoramic view of the beautiful back yard. Three bedrooms and two baths round out the first floor. The lower level features a massive two car garage, half bath, laundry and a large Family Room/Man Cave space for quiet reading or lively entertaining with a third fireplace. So many beautiful options await you in this wonderful home, located in a quiet, attractive, safe and neighborly enclave.

42 Mockingbird Valley Rd, Winchester

$229,000
3 Beds 1 Baths 26013434 MLS
Welcome to a well maintained 3 bedroom 1 full bath home that has been lovingly cared for by only two owners since 1962. Recent updates include new flooring and completed repairs, makiing this property ready for a new owner, while preserving its timeless character. Beautiful hardwood floors add warmth and charm throughout the home. Enjoy relaxing or entertaining on the comfortable spacious patio perfectly sized for gatherings. The brick fireplace with gas logs, located in the living room, adds a cozy ambience on cool evenings. One of the property's standout features is its prime location backing directly to Legacy Grove Park complete with a private gate providing conveninent park access. This unique setting offers addttiional outdoor space, scenic views and a peaceful atmosphere right in your own backyard. . This is a wonderful opportunity to call a well cared for property with an abundance of charm your very own.

30 Virginia Ave, Winchester

$665,000
3 Beds 3 Baths 24025581 MLS
Introducing the Alexis, a stunning all-brick ranch home with incredible curb appeal and a charming front porch. This thoughtfully designed 3-bedroom, 2.5-bath home features a desirable split-bedroom layout, offering privacy and comfort. The spacious primary suite includes a luxurious ensuite with double vanities, a walk-in closet with direct access to the separate utility room for added convenience. The open-concept kitchen flows seamlessly into the great room, which is highlighted by a gas log fireplace and built-in cabinetry. The kitchen is a chef's dream, featuring a large island, a cozy breakfast area, and a walk-in pantry for ample storage. The Alexis also includes a formal dining room, perfect for entertaining, along with a convenient drop zone with a bench for everyday use. With 9-foot ceilings and luxury vinyl plank flooring throughout, this home combines modern elegance with functionality. A 2-car attached garage completes this exquisite floor plan. Let'c customize your dream home in Mallard Cove with CP Builders!

414 Alexis Way, Winchester