Newest Homes for Sale in Winchester, KY

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  /37

  $233,000

  • 3 Beds
  • 2 Baths
  • 1,261 Sq Ft

  14 Cook Ave, Winchester, KY 40391

  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

  Janna Chalfant Smith United Real Estate Bluegrass

  14 Cook Ave, Winchester, KY 40391
• Explore Winchester

• 

  

  

  /89

  $939,000

  • 3 Beds
  • 2 Baths
  • 4,019 Sq Ft

  200 Old Log Lick Rd, Winchester, KY 40391

  Behind a private, gated entrance on 14.38 acres, this 3,481 sq ft all-wood cabin estate is a truly rare find in Central Kentucky. Offering 3 bedrooms, 2 bathrooms, and a flexible bonus room perfect as a 4th bedroom or home office, every inch of this home reflects true craftsmanship — rich wood features throughout, a large sunroom, and a screened-in back porch made for long evenings and unhurried

  

  Brad Smith

  RE/MAX Creative, Winchester

  (859) 374-7374

  200 Old Log Lick Rd, Winchester, KY 40391
• 

  

  

  /26

  $390,000

  Open Sun 2PM - 4PM

  • 3 Beds
  • 2.5 Baths
  • 2,156 Sq Ft

  178 Hawthorne Dr, Winchester, KY 40391

  Welcome to your Kentucky haven. This charming 3 bedroom, 2.5 bath home has a covered front porch and a partially covered back deck that's perfect for enjoying the Summer outdoors. It's located in a well established neighborhood while only being 8 years old. As you step inside you will love the beautiful hardwood and tile flooring that run throughout the house. A separate mudroom is complete with

  Tiffani Casey Waizenhofer Real Estate

  178 Hawthorne Dr, Winchester, KY 40391
• 

  

  

  /41

  $339,900

  Open Sun 1PM - 3PM

  • 3 Beds
  • 2 Baths
  • 1,858 Sq Ft

  23 Windridge Dr, Winchester, KY 40391

  Welcome home to Windridge!!! This beautifully updated all-brick ranch that perfectly blends charm and modern upgrades in a well established, desirable neighborhood is sure to please. Step inside to a bright open-concept living space featuring luxury vinyl flooring, a stunning wood-burning fireplace, and exposed wood ceiling beams that create a warm, inviting atmosphere in the spacious family

  Holly Goeing The Agency

  23 Windridge Dr, Winchester, KY 40391
• 

  

  

  /31

  $240,000

  • 3 Beds
  • 2 Baths
  • 1,162 Sq Ft

  13 Long Ave, Winchester, KY 40391

  Charming 3 bedroom, 2 bath home situated on a large, level lot! Relax and enjoy the inviting covered front porch, perfect for morning coffee or evening unwinding. Inside, you'll find a spacious living room and dining room featuring beautiful hardwood floors that add warmth and character. The generous yard offers plenty of space for outdoor entertaining, gardening, play or future possibilities.

  Kathryn Cheuvront Coldwell Banker McMahan

  13 Long Ave, Winchester, KY 40391
• 

  

  /64

  $259,900

  • 3 Beds
  • 1.5 Baths
  • 1,161 Sq Ft

  17 Holiday Rd, Winchester, KY 40391

  This classic brick ranch house is move-in ready and waiting for you to call it home! Take a step inside the front door to appreciate the gleaming laminate wood floors in the open concept living space. Around the corner, the beautiful kitchen cabinets and updated, stainless, kitchen appliances are ready for family meals and social gatherings around the dining table. In the full bath, you'll find a

  Josh Wood Freedom Realty & Property Management

  17 Holiday Rd, Winchester, KY 40391
• 

  

  /21

  $104,900

  • 2 Beds
  • 2 Baths
  • 924 Sq Ft

  563 Constitution Dr, Winchester, KY 40391

  Affordable housing! Check out this newly remodeled and updated home! 2 bedroom, 2 full bath! All new flooring, cabinets, vanities, and so much more! No lot rent here! You will own the lot as well, making this a great option for starter, downsizing, investment property (previously rented for $925), or just an affordable home. Nice covered porch, 2 storage sheds, brand new metal roof! $150 per

  Jason Townsend Kentucky Residential Real Estate, LLC

  563 Constitution Dr, Winchester, KY 40391
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  /36

  $290,000

  Open Sun 2PM - 4PM

  • 3 Beds
  • 2 Baths
  • 1,650 Sq Ft

  20 Jackson St, Winchester, KY 40391

  Beautifully updated and move-in ready, this 3-bedroom, 2-bath home offers comfort, style, and versatility throughout. Inside, you'll find a spacious living room, an updated kitchen with ample cabinetry, tile showers, original hardwood, modern LVP, and thoughtful finishes throughout. A large utility room offers flexible space for a home office, playroom, or extra storage. The unfinished basement,

  Zova Rothchild Keller Williams Legacy Group

  20 Jackson St, Winchester, KY 40391
• 

  

  /13

  $109,900

  • 4 Beds
  • 2.5 Baths
  • 1,391 Sq Ft

  310 W Hickman St, Winchester, KY 40391

  Opportunity knocks for the buyer with vision! This spacious 4-bedroom, 2.5-bath home is mid renovation and is well on its way to becoming something truly special. With a first-floor primary suite, walk-in closets, partial basement with sump pump already installed, many major systems already in place, and a storage shed in the backyard, many of the big-ticket features are done for you. The home is

  

  George Green

  Green Team Real Estate Service

  (859) 765-7869

  310 W Hickman St, Winchester, KY 40391
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  /38

  $320,000

  • 3 Beds
  • 2.5 Baths
  • 2,100 Sq Ft

  4100 Crowe Ridge Rd, Winchester, KY 40391

  Discover your retreat in this 3 bedroom, 2.5 bath home, perfectly situated for serene country living. The foyer opens into a spacious family room featuring a wood-burning fireplace. Just off the family room is a large, eat-in kitchen. Also on the main level is the primary ensuite and a versatile flex room with endless possibilities. Upstairs, two generous sized bedrooms and a full bath await. The

  Heather Baber Rector Hayden Realtors

  4100 Crowe Ridge Rd, Winchester, KY 40391
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  /33

  $339,900

  • 3 Beds
  • 2.5 Baths
  • 1,608 Sq Ft

  740 Pilot Ridge Ln, Winchester, KY 40391

  Tucked away on 1.25 fully fenced acres, this custom-built home offers some of the most breathtaking views in Winchester. Designed with charm and comfort in mind, this 3-bedroom, 2.5-bath home blends modern convenience with timeless farmhouse style. Step inside to an open, inviting layout filled with natural light and warm finishes throughout. The spacious vaulted master suite is a true retreat,

  Holly Goeing The Agency

  740 Pilot Ridge Ln, Winchester, KY 40391
• 

  

  /18

  $149,900

  • 3 Beds
  • 1 Bath
  • 1,362 Sq Ft

  11 Taylor Ave, Winchester, KY 40391

  Back on Market! Buyers financing fell through. This 3 BR home located in the heart of Winchester and just minutes from the vibrant downtown area, offers the perfect blend of convenience, character, and opportunity. Great opportunity for investors or homeowners. Outside you will love the spacious yard and can relax on the back deck with your morning coffee. Enjoy being within close proximity to

  Alyssa M Boley Coldwell Banker McMahan

  11 Taylor Ave, Winchester, KY 40391
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  /38

  $370,000

  $10K PRICE DROP

  • 1 Bed
  • 2 Baths
  • 2,179 Sq Ft

  3359 Trapp-Goffs Corner Rd, Winchester, KY 40391

  Home listed as one bedroom while unofficially has 3 but 2 of them are interior rooms without windows. 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

  Wayne Elkins RE/MAX Creative Realty

  3359 Trapp-Goffs Corner Rd, Winchester, KY 40391
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  /40

  $299,900

  • 4 Beds
  • 1 Bath
  • 2,327 Sq Ft

  162 French Ave, Winchester, KY 40391

  Could 162 French Ave., Winchester, KY 40391 be your new address? This stunning, updated Craftsman home feels like it was pulled straight from the pages of Southern Living Magazine, blending modern updates with timeless character and charm. Recent improvements including new windows, doors, wiring, and fresh landscaping enhance the home while preserving its original appeal. This move-in ready

  Jonathan Wood HomeLand Real Estate Inc - Mt Sterling

  162 French Ave, Winchester, KY 40391
• 

  

  /12

  $180,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,116 Sq Ft

  41 7th St, Winchester, KY 40391

  Welcome to 41 7th Street. This brick ranch offers 3 bedrooms, 2 full baths, and hardwood floors throughout the living room, hallway, and bedrooms, ready to be refreshed with a re-sand and polish. The layout provides a foundation for a buyer looking to add personal updates and make it their own. Located at the end of the street, the home offers added privacy along with peaceful farm views behind

  

  Austina Bruton

  Re/Max Elite Realty - Hamburg

  (859) 695-6124

  41 7th St, Winchester, KY 40391
• 

  

  /30

  $349,900

  • 5 Beds
  • 4 Baths
  • 4,456 Sq Ft

  410 W Lexington Ave, Winchester, KY 40391

  Whether you're looking for a large residential home, investment opportunity, business potential, or a combination of uses, this property is ready to fit your vision. Featuring 5 bedrooms, 4 baths, soaring 10 foot ceilings, and a welcoming front porch, this unique property blends character, space and versatility. Generous room sizes, timeless charm, and flexible living spaces make it ideal for

  Tracy Ison Bluegrass Home Group

  410 W Lexington Ave, Winchester, KY 40391
• 

  

  /20

  $210,000

  • 3 Beds
  • 1 Bath
  • 1,386 Sq Ft

  301 Snowden Dr, Winchester, KY 40391

  Charming all-brick ranch offering timeless character and everyday functionality! Step inside to a light-filled living room featuring beautiful hardwood floors and a warm, welcoming feel throughout. This home offers three bedrooms and one full bathroom, along with an eat-in kitchen perfect for casual dining and gathering. A dedicated laundry/mud room just off the kitchen provides convenient access

  Julia Lark The Brokerage

  301 Snowden Dr, Winchester, KY 40391
• 

  

  /43

  $299,900

  • 3 Beds
  • 3 Baths
  • 2,821 Sq Ft

  3622 Stamper Dr, Winchester, KY 40391

  This lovely and unique home sits at the end of a quiet street in a secluded circle and backs up to a privacy fenced yard and greenspace right in the heart of town. With recently installed vinyl siding, gutters and gutter guard properties like this are hard to find and the unique amenities inside truly set this home apart. Step through the front door to discover a spacious great room with gleaming

  Josh Wood Freedom Realty & Property Management

  3622 Stamper Dr, Winchester, KY 40391
• 

  

  /14

  $215,000

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft

  104 Bay Hill Dr, Winchester, KY 40391

  You don't want to miss this desirable two primary bedroom home with 2 full bathrooms and large walk-in closets!! There is a gorgeous gas fireplace situated as the focal point of the main living space and an attached one car garage.

  Vanessa Highland Stewart & Co Realty LLC

  104 Bay Hill Dr, Winchester, KY 40391
• 

  

  /92

  $795,000

  • 3 Beds
  • 3 Baths
  • 3,336 Sq Ft

  6356 Van Meter Rd, Winchester, KY 40391

  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

  Josh Wood Freedom Realty & Property Management

  6356 Van Meter Rd, Winchester, KY 40391
• 

  

  /50

  $229,900

  • 3 Beds
  • 1 Bath
  • 1,042 Sq Ft

  217 Short St, Winchester, KY 40391

  This charming ranch home in a desirable neighborhood offers the perfect opportunity for first-time buyers, downsizers, or anyone looking for a move-in ready home with simple, comfortable living. Featuring 3 bedrooms and 1 full bath, this home includes plank flooring, fresh paint updates, updated kitchen appliances, and a functional layout designed for everyday convenience. The extended carport

  Josh Wood Freedom Realty & Property Management

  217 Short St, Winchester, KY 40391
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  /89

  $359,900

  $20K PRICE DROP

  • Land
  • 51.04 Acres
  • $7,052 per Acre

  750 Providence Ln, Winchester, KY 40391

  Discover your own slice of country paradise in southern Clark County. This 51+ acre property blends open pasture with mature woodland, offering endless possibilities—raise cattle, plant crops, keep horses, enjoy outdoor recreation, or build the homestead you've always imagined. Currently used as a private family retreat, the land already has electricity on-site and includes a cistern at an old

  Josh Wood Freedom Realty & Property Management

  750 Providence Ln, Winchester, KY 40391
• 

  

  /21

  $249,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,064 Sq Ft

  12 Pocahontas Trail, Winchester, KY 40391

  Here is your opportunity to purchase a new construction home built in an established neighborhood. Approaching the home you notice the large covered front porch with plenty of room for seating. When you walk in the home, you have white oak LVP flooring running throughout the living room, kitchen and dining area that are all open to one another. The kitchen has white Shaker style cabinets, granite

  Brian England Keller Williams Bluegrass Realty

  12 Pocahontas Trail, Winchester, KY 40391
• 

  

  /46

  $595,000

  Open Sat 12PM - 3PM

  • 4 Beds
  • 3.5 Baths
  • 3,431 Sq Ft

  7919 Mount Sterling Rd, Winchester, KY 40391

  Don't miss the opportunity to own this stunning 3,431 sq. ft. custom-built brick home featuring 4 bedrooms, 3 full baths, and situated on 3 beautiful acres overlooking Stoner Creek. Nestled in a serene, park-like setting, this remarkable property combines the peace of country living with the convenience of nearby amenities. From the moment you step into the dramatic two-story entryway, you'll be

  Hannah Toole Coldwell Banker McMahan

  7919 Mount Sterling Rd, Winchester, KY 40391
• 

  

  /57

  $275,000

  • 3 Beds
  • 2 Baths
  • 1,779 Sq Ft

  720 Terry Dr, Winchester, KY 40391

  Welcome home to this beautifully refreshed 3-bedroom, 2-bath property located in the heart of Winchester, KY, just minutes from the Winchester Bypass for quick and easy commuting. Priced at $275,000, this home offers exceptional value in a highly walkable and convenient neighborhood. Step inside to find a freshly painted interior that feels bright, clean, and move-in ready. The thoughtful layout

  

  Christa Joynt

  Keller Williams Commonwealth

  (859) 903-5709

  720 Terry Dr, Winchester, KY 40391
• 

  

  /52

  $785,000

  • 4 Beds
  • 3 Baths
  • 3,311 Sq Ft

  7300 Old Boonesboro Rd, Winchester, KY 40391

  This beautiful home sits on over 7 acres of peaceful countryside. Bring your horse! The back portion of the land is completely fenced. The private outdoor space includes a huge deck with a lovely view and an inviting covered front porch. The backyard would make the perfect space for your own dream swimming pool. Since the property has a 3-car detached garage; a 2-car attached garage plus a 1275

  Vickie Skeens RE/MAX Elite Lexington

  7300 Old Boonesboro Rd, Winchester, KY 40391
• 

  

  /24

  $280,000

  • 4 Beds
  • 3.5 Baths
  • 3,276 Sq Ft

  133 Bay Hill Dr, Winchester, KY 40391

  Welcome to 133 Bay Hill Drive in Winchester, Kentucky — a spacious and beautifully maintained home offering over 3,200 square feet of living space in one of the area's desirable subdivisions. Conveniently located just minutes from town and close to local factories and major employers, this property offers the perfect blend of comfort, convenience, and neighborhood living. Inside, you'll find

  

  Dustin Pennington

  Keller Williams Legacy Group

  (859) 636-6943

  133 Bay Hill Dr, Winchester, KY 40391
• 

  

  /24

  $239,000

  Open Sun 1PM - 3PM

  • 3 Beds
  • 1 Bath
  • 1,100 Sq Ft

  125 Kittison Dr, Winchester, KY 40391

  Charming ranch home featuring 3 bedrooms, 1 full bath with a spacious layout and inviting curb appeal. Enjoy relaxing or entertaining on the covered back patio overlooking the large backyard with plenty of room for pets, play, or gardening. The kitchen offers beautiful granite countertops, ample cabinet space, and all appliances stay for added convenience. A wonderful opportunity for comfortable

  Kathryn Cheuvront Coldwell Banker McMahan

  125 Kittison Dr, Winchester, KY 40391
• 

  

  /20

  $225,000

  Open Sat 8AM - 12PM $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,136 Sq Ft

  86 Brink Ave, Winchester, KY 40391

  Welcome Home! Its ready for you! All the updates have been done. You will enjoy a beautiful newly updated kitchen with new appliances, new laminate floors, updated bathrooms , and fresh paint throughout. Enjoy the confidence of a new HVAC, new Hot Water Heater, and young metal roof. This home provides the ease and comfort of a first floor primary and spacious livingroom. Enjoy beautiful evenings

  Jennifer Hukill RE/MAX Elite Lexington

  86 Brink Ave, Winchester, KY 40391
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  /51

  $400,000

  • 8 Beds
  • 5 Baths
  • 4,687 Sq Ft

  23 Wheeler Ave, Winchester, KY 40391

  Here is a chance to own a fully leased fourplex with multiple long term tenants. Located across from a very nice park with plenty of parking. Tenants pay their own utilities. Gross rents are currently $3110/month. Please allow 48 hours to notify tenants for a showing. Showings can be scheduled with proof of funds or a lender pre-approval letter from potential buyers.

  Alexander Heister Keller Williams Bluegrass Realty

  23 Wheeler Ave, Winchester, KY 40391
• 

  

  /53

  $268,900

  • 4 Beds
  • 2.5 Baths
  • 1,510 Sq Ft

  311 Geronimo Ct, Winchester, KY 40391

  Spacious and well - maintained 4 bedroom home featuring 2 full bathrooms, one half bath which is ready to be upgraded with the addition of a shower to function as an additional full bathroom. This home offers a comfortable layout with replacement windows, a cozy wood burning fireplace and updated stainless steel appliances incuding the range, refrigerator, dishwasher and microwave. Enjoy outdoor

  

  Brenda Sipes

  WEICHERT REALTORS - ABG Properties

  (859) 549-3201

  311 Geronimo Ct, Winchester, KY 40391
• 

  

  /3

  $399,000

  • Land
  • 11.3 Acres
  • $35,310 per Acre

  0 Fairholme Way, Winchester, KY 40391

  11 acres of golf course adjacent land with development plan. Owner/Broker. Road and utility estimates available upon request. A list of individuals interested in lots available upon contract.

  Steve Adams Steven D Adams Real Estate Services, LLC

  0 Fairholme Way, Winchester, KY 40391
• 

  

  /14

  $152,500

  $7K PRICE DROP

  • Land
  • 2.66 Acres
  • $57,374 per Acre

  590 Craig Crossing, Winchester, KY 40391

  Don't let this opportunity pass you by again. This prime lot in Thoroughbred Estates is back on the market due to Current owners change of plans. This lot is ready for your new home with a beautiful setting and located close to Winchester and Lexington in a new Luxury Subdivision. Watch the sun set each night from your rear deck or pool. Call today!!!

  Keith Wilson Coldwell Banker McMahan

  590 Craig Crossing, Winchester, KY 40391
• 

  

  /37

  $290,000

  • 3 Beds
  • 2 Baths
  • 1,260 Sq Ft

  116 Sturbridge Ln, Winchester, KY 40391

  The ranch home at 116 Sturbridge Lane in Winchester, KY has 3 bedrooms, 2 full bathrooms, an eat-in kitchen, large living room, laundry room and 2 car garage. The home has been lovingly cared for and features multiple upgrades. Situated behind Lowe's, it offers easy access to dining, shopping, the by-pass, and medical & educational facilities.

  Donna C. Slone-Crumbie Wright Realty

  116 Sturbridge Ln, Winchester, KY 40391
• 

  

  /24

  $199,900

  • 3 Beds
  • 2 Baths
  • 915 Sq Ft

  225 Buffalo Trace, Winchester, KY 40391

  This move in ready ranch home offering 3 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

  225 Buffalo Trace, Winchester, KY 40391
• 

  

  /65

  $609,900

  • 5 Beds
  • 4 Baths
  • 4,515 Sq Ft

  6595 Mount Sterling Rd, Winchester, KY 40391

  Welcome to 6595 Mount Sterling Rd. offering the perfect blend of space, convenience, and flexibility on 2.59 acres. Ideally located just off I 64 between Winchester and Mount Sterling, this property provides easy interstate access while still offering privacy and room to spread out. This custom home features 5 bedrooms, 3 full baths, and a versatile floor plan. The main level includes a vaulted

  Brooke Otis Mullins RO&CO Real Estate

  6595 Mount Sterling Rd, Winchester, KY 40391
• 

  

  /120

  $1,695,000

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

  3166 Colby Rd, Winchester, KY 40391

  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

  Alyssa M Boley Coldwell Banker McMahan

  3166 Colby Rd, Winchester, KY 40391
• 

  

  /23

  $99,900

  • 3 Beds
  • 2 Baths
  • 675 Sq Ft

  2799 Pine Ridge Rd, Winchester, KY 40391

  If your looking for a fixer upper, this is it. House on 2 acres in the country with lots of potential. Laundry is off the kitchen, but floor is soft from a water leak. From the kitchen you will see a guest bath, dining and living area. To the left is a hallway that leads to 2 bedrooms, drywalled just needs to be finished. To the right of the living area is your master bedroom and bath. With some

  Robin Horn Keller Williams Commonwealth

  2799 Pine Ridge Rd, Winchester, KY 40391
• 

  /2

  $78,500

  • Land
  • 9,600 Sq Ft
  • $356,171 per Acre

  Lot 3 Plantations Dr, Winchester, KY 40391

  NOW SELLING SFH Buildable Lots of PHASE ONE: 12 Buildable Lots (minimum lot is 9600+ sqft) of PHASE ONE of Deerlawn's Development located at 2395 Paris Rd (Parent Listing). Earmarked as Winchester, Ky's most anticipated residential development consisting of an ambitious 274+-acre expansion formerly known as the well-established Royal Oaks/Plantation neighborhoods, Phase One has 12 lots ready for

  Melia Hord MELIA Realty LLC

  Lot 3 Plantations Dr, Winchester, KY 40391
• 

  

  /39

  $315,000

  • 3 Beds
  • 2 Baths
  • 1,932 Sq Ft

  13 Lakeview Dr, Winchester, KY 40391

  Beautifully updated brick ranch with a partially finished basement offering 3 bedrooms and 2 full baths! The main level features a welcoming living room with a masonry gas log fireplace that opens into the updated kitchen complete with island bar seating, eat-in dining area, and access to the screened-in deck, perfect for relaxing or entertaining. Down the hall, you'll find two bedrooms, a full

  Michelle Blackburn RE/MAX Creative, Winchester

  13 Lakeview Dr, Winchester, KY 40391

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