Studio to 5 Bedroom Homes for Sale in Winchester, KY

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  /47

  $372,900

  • 4 Beds
  • 3 Baths
  • 2,105 Sq Ft

  114 Mallard Ln, Winchester, KY 40391

  Nestled in a quiet cul-de-sac just minutes from shopping, dining, and the interstate, this unique ranch-style home offers a space, flexibility, and convenience. Originally designed as a duplex, the property has been thoughtfully renovated and modernized for an easy lifestyle. The main living area welcomes you with a light-filled, open concept layout featuring beautiful hardwood floors, a

  

  Robin Jones

  Keller Williams Legacy Group

  (859) 809-3100

  114 Mallard Ln, Winchester, KY 40391
• Explore Winchester

• 

  

  

  /87

  $829,000

  • 4 Beds
  • 3.5 Baths
  • 4,345 Sq Ft

  1701 Gay Evans Rd, Winchester, KY 40391

  Move into INSTANT equity Listed BELOW appraisal! This 4bd 4bath home has 2 BONUS ROOMS, a pool PLUS an attached and detached garage with finished space! This is a MUST see! Your dream country retreat awaits! Nestled on 8+ scenic acres, this stunning brick ranch offers the perfect blend of modern efficiency, functional living space, and peaceful country charm. A brand-new geothermal heating and

  

  Nora Williams

  Keller Williams Commonwealth

  (859) 544-2514

  1701 Gay Evans Rd, Winchester, KY 40391
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  /71

  $799,999

  • 4 Beds
  • 2.5 Baths
  • 5,290 Sq Ft

  186 Chardonnay Ct, Winchester, KY 40391

  Step into a world of both comfort and convenience with this beautiful 3/4 bedroom, two and one half bath, perfectly designed for relaxation and entertainment. Key features of this property include outdoor spaces to enjoy morning coffee or quiet evening chats. The cozy back porch extends your living space, ideal for dining and enjoying the tranquil surroundings, The beautifully designed patio

  

  Brenda Sipes

  WEICHERT REALTORS - ABG Properties

  (859) 813-4308

  186 Chardonnay Ct, Winchester, KY 40391
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  /36

  $319,900

  • 5 Beds
  • 2 Baths
  • 2,082 Sq Ft

  128 Cherokee Dr, Winchester, KY 40391

  **Open House Sunday 11/16 1-3PM** Welcome to 128 Cherokee Drive, a beautifully maintained home in a quiet and desirable neighborhood. With 5 bedrooms, two full bathrooms, and a second living room on the lower floor, there is plenty of room for the entire family and friends. A spacious backyard , many appealing updates since 2022, and exceptional curb appeal and charm, this home is just waiting

  

  Tyler Hurst

  Thwaites Realtors LLC

  (859) 681-9697

  128 Cherokee Dr, Winchester, KY 40391
• 

  

  

  /22

  $147,000

  • 2 Beds
  • 1 Bath
  • 807 Sq Ft

  3208 Ford Hampton Rd, Winchester, KY 40391

  Escape to a lifestyle defined by the peace and natural beauty of this delightful two bedroom property just steps away from the majestic Kentucky River, this home isn't just a place to iive, it is a dedicated sanctuary whether you are seeking a cozy year round residence or a recreational retreat. One of the standout features is the exceptioal connection to the outdoors with generous porches on

  

  Brenda Sipes

  WEICHERT REALTORS - ABG Properties

  (859) 765-6889

  3208 Ford Hampton Rd, Winchester, KY 40391
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  /51

  $318,000 Open Sun 1PM - 3PM

  • 3 Beds
  • 2 Baths
  • 1,913 Sq Ft

  22 N Bloomfield Rd, Winchester, KY 40391

  Welcome to this beautiful Craftsman style house on a very large lot, with a beautiful backyard. The newly finished stunning original hardwood floors invite you into the living room and family/dining room. There are two functioning wood burning fireplaces one in the family/dining room and another one in the kitchen. The kitchen is updated with a large island, granite counter tops, stainless steel

  Libby VanMeter Marshall Lane Real Estate - Lexington

  22 N Bloomfield Rd, Winchester, KY 40391
• 

  

  /19

  $499,000

  • Land
  • 36.94 Acres
  • $13,508 per Acre

  1455B Ky-89 Lot Unit Wp001, Winchester, KY 40391

  Don't miss this rare chance to own 36.45 premium acres on the outskirts of Winchesteran unbeatable blend of open farmland, development potential, and a truly top-tier location. Just minutes from I-64 and a quick drive to Lexington, this tract offers the convenience buyers want with the space and freedom they rarely find. The gorgeous rolling fields make this property ideal for farming, hay

  Greg Meade Whitetail Properties Real Estate

  1455B Ky-89 Lot Unit Wp001, Winchester, KY 40391
• 

  

  /23

  $498,900

  • Land
  • 25.87 Acres
  • $19,285 per Acre

  2996/3056 Irvine Rd, Winchester, KY 40391

  Rare find! Gorgeous 25 acres of gently rolling land with a barn and creek is perfect for building your dream home and creating your homestead! Don't miss this opportunity! This is farm is conveniently located 20 miles from Hamburg and 5 miles from the Winchester bypass. No city sewage. Deed restrictions apply. Relax and enjoy the spectacular views. Get ready to enjoy life! Land consists of 2

  Lura Justice Rector Hayden, Realtors

  2996/3056 Irvine Rd, Winchester, KY 40391
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  /51

  $775,000

  • 5 Beds
  • 3.5 Baths
  • 2,904 Sq Ft

  1783 Gay Evans Rd, Winchester, KY 40391

  Welcome to your dream homestead retreat! Tucked away on 7.27 beautiful acres, this stunning 5-bedroom, 4-bath home offers the perfect blend of comfort, function, and country living. From the inviting front porch sunsets to the resort-style outdoor space, this property has everything you've been searching for. Step inside to the two story foyer that leads to an open-concept main level featuring

  Lucy Martin Jenkins United Real Estate Bluegrass

  1783 Gay Evans Rd, Winchester, KY 40391
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  /30

  $220,000

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft

  2721 Pretty Run Rd, Winchester, KY 40391

  Back on market due to buyer financing, no fault of the seller! Situated on 5 scenic acres along a highly sought-after country road, this 3-bedroom, 2-bath property presents an excellent opportunity to create your dream rural retreat. The home features a functional layout with a spacious living area, an eat-in kitchen, and a primary suite with its own bath. Two additional bedrooms offer

  Michelle Blackburn RE/MAX Creative, Winchester

  2721 Pretty Run Rd, Winchester, KY 40391
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  /100

  $1,889,000

  • 3 Beds
  • 2.5 Baths
  • 4,518 Sq Ft

  3166 Colby Rd, Winchester, KY 40391

  Welcome to this beautiful 33± acre estate, offering the perfect blend of country charm, modern comfort, and endless opportunity. The stately historical home, built in 1919, retains timeless character and can be registered with the Historical Home Society. Enjoy stunning mountain views — located at one of the highest points in Clark County, where you can see the dormitories at EKU in Richmond and

  Alyssa M Boley Coldwell Banker McMahan

  3166 Colby Rd, Winchester, KY 40391
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  /6

  $171,000

  • 2 Beds
  • 1 Bath
  • 870 Sq Ft

  102 W Hickman St, Winchester, KY 40391

  102 W Hickman St, Winchester, KY 40391Cozy and full of potential! This 11⁄2-story home offers 2 bedrooms and 1 bathroom, making it a great fit for a small household or as part of a rental investment portfolio. Currently used as a rental, the property features a functional layout with living spaces on the main floor and additional space upstairs. Located on a quiet street yet close to downtown

  David Espinosa Bluegrass Realty Pros, Inc

  102 W Hickman St, Winchester, KY 40391
• 

  

  /18

  $499,900 New Construction

  • 4 Beds
  • 3 Baths
  • 2,300 Sq Ft

  414 Fairholme Way, Winchester, KY 40391

  Welcome to Fairholme Estates—where luxury meets comfort! This brand-new ranch-style home offers 4 bedrooms, 3 full baths, and 9' ceilings throughout for a spacious, airy feel. The designer kitchen features a huge island, beautiful finishes, and flows seamlessly into the vaulted great room filled with natural light from large windows. A Jack and Jill bath with separate sinks provides convenience,

  Kristin Ray Lifstyl Real Estate

  414 Fairholme Way, Winchester, KY 40391
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  /19

  $284,000

  • 3 Beds
  • 2 Baths
  • 1,966 Sq Ft

  729 Wayland Dr, Winchester, KY 40391

  This charming 3-bedroom, 2-bath split level home offers the perfect blend of comfort and convenience-located just minutes from Lexington's popular Hamburg area with endless shopping, dining and entertainment options right at your fingertips! Step inside to find a beautifully updated kitchen featuring brand-new granite countertops and a stylish new island, perfect for family meals or entertaining

  Brittany Beer EXP Realty, LLC

  729 Wayland Dr, Winchester, KY 40391
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  /94

  $849,900

  • 4 Beds
  • 3.5 Baths
  • 4,584 Sq Ft

  4040 Muddy Creek Rd, Winchester, KY 40391

  A Farmhouse Retreat with Timeless Craftsmanship on 13.6 AcresNestled on 13.6 rolling acres in Clark County, this custom built farmhouse captivates with soaring tongue-and-groove ceilings, rich woodwork, and thoughtful craftsmanship that sets this home apart. Oversized doors, custom cabinetry, and detailed finishes showcase the quality throughout, while two wood-burning fireplaces with

  Julie Wiggington RE/MAX Creative, Winchester

  4040 Muddy Creek Rd, Winchester, KY 40391
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  /103

  $2,650,000

  • 6 Beds
  • 5.5 Baths
  • 7,274 Sq Ft

  5045 Van Meter Rd, Winchester, KY 40391

  Welcome to a truly exceptional 10-acre estate, where luxury and nature converge. This custom-built, three-story home, completed in 2006 , offers 7274 sq ft of meticulously designed living space. With 6 bedrooms and 5.5 bathrooms, there's ample room for family and guests. The impressive 2432 sq ft, temperature-controlled 5-car garage provides extensive space for vehicles and hobbies. Beyond the

  The Prather Team - Michael Prather Keller Williams Bluegrass Realty

  5045 Van Meter Rd, Winchester, KY 40391
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  /30

  $259,900

  • 4 Beds
  • 2 Baths
  • 2,683 Sq Ft

  217 S Highland St, Winchester, KY 40391

  This Spacious investment property is ready for its new owner. The home features fresh updates throughout, large living spaces and endless possibilities. Schedule your showing while you can!

  Michael Hilario The Agency

  217 S Highland St, Winchester, KY 40391
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  /32

  $249,900

  • 3 Beds
  • 2 Baths
  • 1,904 Sq Ft

  528 Estes Dr, Winchester, KY 40391

  Don't miss out on seeing this 3/2 brick ranch home in a convenient location to shopping, dining, parks, pool and more. Large open family room and kitchen with bamboo flooring. The kitchen has a large granite counter top island with newer stainless appliances and a gas range. This home is complete with an Aurora above ground pool for all the summer fun. The seller has already planted garden

  Josh Wood Freedom Realty & Property Management

  528 Estes Dr, Winchester, KY 40391
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  /92

  $1,200,000

  • 5 Beds
  • 7 Baths
  • 8,236 Sq Ft

  6237 Bybee Rd, Winchester, KY 40391

  Step into timeless elegance with this breathtaking modern Victorian-style masterpiece, perfectly positioned on 4.39 acres with panoramic views of sunrises, sunsets, and distant mountains. Designed and built by Tom Padgett, this home is rich in character and detail—from hand-hewn wood beam ceilings to Waterford crystal chandeliers. The grand 2-story foyer welcomes you into a flowing layout that

  Amanda Marcum Berkshire Hathaway HomeServices Foster Realtors

  6237 Bybee Rd, Winchester, KY 40391
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  /10

  $369,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,635 Sq Ft

  206 Jett Dr, Winchester, KY 40391

  New Construction, come view, great house plan, ranch on a crawl space, 3 bedrooms, 2 bath, you will love this inviting neighborhood, plan shown on line could vary, this is a spec home, all the colors have been decided, fixtures, flooring, brick, siding, cabinets, countertops have been ordered, restrictions apply, no HOA, buyer to verify sq ft of home and lot. This home is close to I-64, I-75,

  Mila Ensor Ensor Real Estate, LLC

  206 Jett Dr, Winchester, KY 40391
• 

  

  /22

  $167,500

  • 3 Beds
  • 1 Bath
  • 1,274 Sq Ft

  146 Cook Ave, Winchester, KY 40391

  Sellers willing to pay towards closing cost! Welcome to 146 Cook Avenue in Winchester, Kentucky — an updated home combining classic charm with modern style. This 3-bedroom, 1-bath property offers around 1,274 sq. ft. of comfortable living space with an open-concept layout, newer flooring throughout, and a completely renovated kitchen. The tiled bathroom includes space for a washer and dryer, and

  Autumn Johannes National Real Estate

  146 Cook Ave, Winchester, KY 40391
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  /10

  $550,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,200 Sq Ft

  107 Bella Shae Way, Winchester, KY 40391

  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

  Shane Underwood Keller Williams Commonwealth

  107 Bella Shae Way, Winchester, KY 40391
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  /87

  $3,100,000

  • 3 Beds
  • 3 Baths
  • 3,693 Sq Ft

  3049 Ironworks Rd, Winchester, KY 40391

  150 acres of pure Kentucky beauty in Winchester, on the market for the first time ever. This incredible cattle farm has been owned by the same family since 1803 and is now ready for its next chapter. With rolling land, four barns, two storage sheds, four ponds, a creek, and two homes, this estate is truly unmatched. If you've been waiting for your dream property, this is it.

  Zova Rothchild Keller Williams Legacy Group

  3049 Ironworks Rd, Winchester, KY 40391
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  /3

  $380,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,677 Sq Ft

  270 Evergreen Dr, Winchester, KY 40391

  Welcome to The Run for the Roses - a thoughtfully designed proposed construction home located in the desirable Locust Hill Acres community. This charming home offers an open concept floor plan perfect for modern living, featuring 3 spacious bedrooms and 2 full bathrooms on unfinished walkout basement.The large primary suite is a true retreat, complete with a generously sized walk-in closet

  Rex Hall United Real Estate Bluegrass

  270 Evergreen Dr, Winchester, KY 40391
• 

  

  /22

  $221,500

  • 4 Beds
  • 2 Baths
  • 1,370 Sq Ft

  521 Acadia Way, Winchester, KY 40391

  This move in ready ranch home offering 4 bedrooms and 2 full bathrooms is ready for a new owner. This home is in an income restricted community, 80% of LIHTC for Clark County. Property offers brand new cabinets, countertops, appliances, flooring, fresh painting and more. Contact listing agent to receive the income limits for buyers to qualify to purchase property. Set up your showing today!

  Tyler I Back The Brokerage

  521 Acadia Way, Winchester, KY 40391
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  /34

  $275,000

  • 4 Beds
  • 3 Baths
  • 1,850 Sq Ft

  20 Bon-Haven Ave, Winchester, KY 40391

  Welcome to 20 Bon Haven Avenue, a beautifully renovated 4-bedroom, 3 full bathroom home ideally located directly across from the new Legacy Grove Park in Winchester, KY. This spacious residence blends modern upgrades with timeless charm, offering the perfect retreat for families and entertainers alike.Step inside to find a bright and airy open floor plan, highlighted by brand-new plumbing and

  Jacqueline Marchildon Lifstyl Real Estate

  20 Bon-Haven Ave, Winchester, KY 40391
• 

  

  /22

  $665,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,643 Sq Ft

  414 Alexis Way, Winchester, KY 40391

  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

  Shane Underwood Keller Williams Commonwealth

  414 Alexis Way, Winchester, KY 40391
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  /9

  $785,000 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,476 Sq Ft

  425 Alexis Way, Winchester, KY 40391

  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

  Shane Underwood Keller Williams Commonwealth

  425 Alexis Way, Winchester, KY 40391
• 

  

  /18

  $209,900

  • 3 Beds
  • 1 Bath
  • 1,074 Sq Ft

  245 Ecton Rd, Winchester, KY 40391

  Will not qualify for FHA because of garage. Welcome to this fully updated home that is cozy and full of character. Featuring brand new central heating and air, electric, drywall, spray foam insulation, kitchen cabinets, water heater, and stunning hardwood floors throughout. This beautiful kitchen boasts all brand new appliances, butcher block countertops, sage green cabinets, a 30 inch farmhouse

  Anthony Gigilo ListWithFreedom.com

  245 Ecton Rd, Winchester, KY 40391
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  /36

  $262,500

  • 3 Beds
  • 2 Baths
  • 1,234 Sq Ft

  433 Wellington Way, Winchester, KY 40391

  Completely renovated and move-in ready! This 3-bedroom, 2-bath home offers 1,234 sq. ft. of stylish living with beautiful hardwood floors, fresh finishes, and a bright open layout. The vaulted ceiling in the main living area adds space and light, while the updated kitchen features modern cabinetry and new appliances. Both bathrooms have been tastefully redone, and every detail reflects quality

  Stephen Brashear Real Broker LLC

  433 Wellington Way, Winchester, KY 40391
• 

  

  /3

  $380,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,677 Sq Ft

  230 Evergreen Dr, Winchester, KY 40391

  Welcome to The Run for the Roses - a thoughtfully designed proposed construction home located in the desirable Locust Hill Acres community. This charming home offers an open concept floor plan perfect for modern living, featuring 3 spacious bedrooms and 2 full bathrooms.The large primary suite is a true retreat, complete with a generously sized walk-in closet and a well-appointed ensuite

  Rex Hall United Real Estate Bluegrass

  230 Evergreen Dr, Winchester, KY 40391
• 

  

  /22

  $270,000

  • 4 Beds
  • 2 Baths
  • 2,332 Sq Ft

  35 Cherokee Ct, Winchester, KY 40391

  Step into this 4-bedroom, 2 full bath split-foyer home, perfectly designed for comfortable everyday living. The upper level features three generously sized bedrooms, a full bath, a bright living room, kitchen, and dining area—ideal for gathering with family and friends. Just off the kitchen, enjoy easy access to the covered deck overlooking a spacious backyard. The lower level offers even more

  Brenda Rue Keller Williams Bluegrass Realty

  35 Cherokee Ct, Winchester, KY 40391
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  /54

  $318,500

  • 4 Beds
  • 1.5 Baths
  • 2,170 Sq Ft

  214 S Burns Ave, Winchester, KY 40391

  Own a beautifully maintained piece of Winchester, KY history on desirable South Burns Avenue. This charming home features an inviting wrap-around porch perfect for year-round enjoyment and outstanding curb appeal. Step into a warm and welcoming entryway where refinished hardwood floors flow throughout the main level. Original pocket doors open into the library, showcasing the home's timeless

  Christa Joynt Keller Williams Commonwealth

  214 S Burns Ave, Winchester, KY 40391
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  /2

  $5,646,000

  • 2 Beds
  • 3 Baths
  • 37,192 Sq Ft

  175 Chatham Place, Winchester, KY 40391

  36 Townhomes ,located behind Lowes,Winchester,Ky.Great rental property, owner will do some owner financing

  Garry Milton Milton and Associates Real Estate

  175 Chatham Place, Winchester, KY 40391
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  /36

  $379,000

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft

  133 Shala-Mar Rue, Winchester, KY 40391

  Welcome to your next home in one of Clark County's most desirable neighborhoods—Shala Mar Estates! This beautifully updated 3-bedroom, 2-bathroom home offers the perfect blend of comfort, space, and modern convenience. Step into the expansive primary bedroom, a true retreat, complete with a stunning ensuite bathroom featuring a brand-new soaking tub and a separate tiled shower. The additional

  Nena Honaker Tom Goebel & Company

  133 Shala-Mar Rue, Winchester, KY 40391
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  /38

  $389,900

  • 4 Beds
  • 2 Baths
  • 2,659 Sq Ft

  6239 Old Boonesboro Rd, Winchester, KY 40391

  Welcome Home to the beautiful country! If you've been looking for quiet, space, and a place that truly feels like home, this charming Cape Cod on nearly 2 acres in Clark County checks all the boxes. Tucked into a peaceful rural setting yet conveniently located near I-75, I-64 and the Winchester Bypass, this property offers the best of country living with easy access to town. With over 2,600

  Kenya Woods United Real Estate Bluegrass

  6239 Old Boonesboro Rd, Winchester, KY 40391
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  /103

  $3,500,000

  • 6 Beds
  • 5.5 Baths
  • 7,274 Sq Ft

  5045 Van Meter Rd, Winchester, KY 40391

  Welcome to a truly exceptional 78-acre estate, where luxury and nature converge. This custom-built, three-story home, completed in 2006 , offers 7274 sq ft of meticulously designed living space. With 6 bedrooms and 5.5 bathrooms, there's ample room for family and guests. The impressive 2432 sq ft, temperature-controlled 5-car garage provides extensive space for vehicles and hobbies. Beyond the

  The Prather Team - Michael Prather Keller Williams Bluegrass Realty

  5045 Van Meter Rd, Winchester, KY 40391
• 

  /2

  $369,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,558 Sq Ft

  204 Jett Dr, Winchester, KY 40391

  New Construction, don't wait this one will not last, 3 bed/2 bath ranch, great floor plan, close to I-64 and I-75, lexington, richmond, call today! All colors, fixtures, granite, siding, outside landscaping, stone/brick, deck size, flooring have been ordered, New photos will be posted as house construction continues

  Mila Ensor Ensor Real Estate, LLC

  204 Jett Dr, Winchester, KY 40391
• 

  

  /3

  $670,000 New Construction

  • 3 Beds
  • 2 Baths
  • 2,261 Sq Ft

  113 Bella Shae Way, Winchester, KY 40391

  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

  Shane Underwood Keller Williams Commonwealth

  113 Bella Shae Way, Winchester, KY 40391
• 

  

  /26

  $260,000

  • 3 Beds
  • 2 Baths
  • 1,749 Sq Ft

  21 Virginia Ave, Winchester, KY 40391

  This updated and well-cared for home offers comfort, flexibility, and room to grow. You'll love the bright living area, the updated flooring, and the beautiful new kitchen. The kitchen offers plenty of workspace, modern finishes, new appliances, butcher-block countertops and easy access to the sunroom for everyday convenience. Sip your morning coffee in the oversized sunroom while warming up to

  Emily Crump EXP Realty, LLC

  21 Virginia Ave, Winchester, KY 40391

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