Newest Homes for Sale in Winchester, KY

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  /26

  $234,900

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

  528 Estes Dr, Winchester, KY 40391

  This home is complete with an Aurora above ground pool for all the summer fun. The 3 beds 2 bath brick ranch home is located conveniently to shopping, dining, parks, pool and more. Large open family room and kitchen with wood bamboo flooring. The kitchen has a large granite counter top island with newer stainless appliances and a gas range. There is an oversized storage/tool shed, and a partially

  Josh Wood Freedom Realty & Property Management

  528 Estes Dr, Winchester, KY 40391
• Explore Winchester

• 

  

  

  /38

  $380,000

  • 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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  /37

  $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
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  /46

  $595,000

  • 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
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  /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
• 

  

  /23

  $239,000

  • 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

  $230,000

  • 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
• 

  

  /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
• 

  

  /32

  $219,500

  • 3 Beds
  • 2 Baths
  • 1,197 Sq Ft

  525 Colby Ridge Blvd, Winchester, KY 40391

  Location, location, location. This duplex is located within minutes of the Winchester Bypass and Colby Road. This one level home offers 3 bedrooms, 2 full baths, great room with fireplace, eat in kitchen, and a one car garage. In 2023 the owners remodeled the bathrooms, added a new kitchen sink and countertops. The LVP flooring was also completed in 2023. The house includes all the kitchen

  Craig Bridgewater Bridgewater Real Estate

  525 Colby Ridge Blvd, Winchester, KY 40391
• 

  

  /34

  $269,000

  • 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
• 

  

  /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

  $154,900

  $5K PRICE DROP

  • Land
  • 2.66 Acres
  • $58,277 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
• 

  

  /36

  $225,000

  • 3 Beds
  • 2 Baths
  • 1,134 Sq Ft

  516 Hidden Hills Way, Winchester, KY 40391

  Charming 3 bedroom, 2 full bath home featuring a vaulted great room with an open, spacious feel. This move in ready property offers all new appliances, brand new flooring, and modern updates that make everyday living both stylish and comfortable. Step outside to enjoy the private backyard complete with a wood privacy fence and a deck perfect for grilling, entertaining, or relaxing. A wonderful

  Craig Bridgewater Bridgewater Real Estate

  516 Hidden Hills Way, 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
• 

  

  /38

  $289,900

  • 3 Beds
  • 2 Baths
  • 1,420 Sq Ft

  137 Eastridge Dr, Winchester, KY 40391

  Welcome to this delightful 1.5-story home perfectly situated on a spacious corner lot just off the Eastern Bypass and only minutes from I-64. Convenience meets comfort in this beautifully maintained property offering 3 bedrooms, 2 full baths, and an inviting layout designed for everyday living. Step inside to an open living area ideal for entertaining, a spacious kitchen and dining space, and

  Kathy Burton Coldwell Banker McMahan

  137 Eastridge Dr, Winchester, KY 40391
• 

  

  /25

  $260,000

  • 3 Beds
  • 2 Baths
  • 1,809 Sq Ft

  316 Maryland Ave, Winchester, KY 40391

  Brick ranch on a partially finished basement offering 3 bedrooms and 2 full baths! The main level welcomes you into a comfortable living room featuring a masonry wood-burning fireplace, along with a spacious kitchen, all three bedrooms, and a full bath located down the hall. The kitchen provides access to the basement where you'll find additional living space in the cozy den area complete with a

  Michelle Blackburn RE/MAX Creative, Winchester

  316 Maryland Ave, Winchester, KY 40391
• 

  /2

  $14,100,000

  • Land
  • 274.52 Acres
  • $51,362 per Acre

  2395 Paris Rd, Winchester, KY 40391

  NOW PRE-SELLING: Deerlawn Development is Winchester, Ky's most anticipated residential development--an ambitious 274+-acre expansion formerly known as the well-established Royal Oaks/Plantation neighborhoods. Located at 2395 Paris Road, and positioned off I-64 at Exit 96 across from the rapidly expanding Industrial Park, Deerlawn is a master-planned community offering 438 single-family homes, and

  Melia Hord MELIA Realty LLC

  2395 Paris Rd, Winchester, KY 40391
• 

  /2

  $882,000

  • Land
  • 3.93 Acres
  • $224,427 per Acre

  Lot 1 - 7 Plantations Dr, Winchester, KY 40391

  NOW SELLING PHASE ONE: 7 of the 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 you to build

  Melia Hord MELIA Realty LLC

  Lot 1 - 7 Plantations Dr, Winchester, KY 40391
• 

  /2

  $78,500

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

  Lot 4 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 4 Plantations Dr, Winchester, KY 40391
• 

  

  /21

  $199,900

  • 3 Beds
  • 2 Baths
  • 1,140 Sq Ft

  265 Cunningham Ln, Winchester, KY 40391

  (back on the market due to buyers financing) Adventure is always within reach at this property! Located just 35 minutes from Red River Gorge and only 26 minutes from Natural Bridge State Resort Park, this home puts you close to some of Kentucky's most popular outdoor attractions. Spend your weekends hiking scenic trails, canoeing, kayaking, fishing, swimming, riding the sky lift, playing mini

  Kierstin Shaffer Berkshire Hathaway HomeServices Foster Realtors

  265 Cunningham Ln, Winchester, KY 40391
• 

  

  /38

  $484,900

  New Construction

  • 4 Beds
  • 3 Baths
  • 2,418 Sq Ft

  414 Fairholme Way, Winchester, KY 40391

  Step into a lifestyle where modern luxury and brand-new construction come together seamlessly. This home is perfectly positioned with golf course views and unforgettable sunset skies, this newly built home offers the kind of setting that turns ordinary evenings into your favorite part of the day—without sacrificing style, comfort, or convenience. Inside, soaring vaulted ceilings and a warm

  Morgan Withrow The Brokerage

  414 Fairholme Way, Winchester, KY 40391
• 

  

  /34

  $219,900

  • 4 Beds
  • 1.5 Baths
  • 1,848 Sq Ft

  339 S Main St, Winchester, KY 40391

  Beautiful move-in ready Cape Cod home on the edge of historic downtown Winchester! This home is vacant and priced to sell! All new LVP flooring throughout (except for the original hardwood in the Dining Room), new paint in all rooms and so much more! 3 nice-sized bedrooms upstairs and a 4th bedroom on the main level. An eat-in kitchen plus a separate Dining Room and a Family Room with a gas log

  Jim Woodrum RE/MAX Creative, Winchester

  339 S Main St, Winchester, KY 40391

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