Newest Homes for Sale in Winchester, KY

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  /5

  $95,000

  • 3 Beds
  • 2 Baths
  • 750 Sq Ft

  113 Mimosa Dr, Winchester, KY 40391

  Discover the perfect balance between home ownership, affordability, and rural tranquility in this charming 3-bedroom two bath home. Conveniently located near shopping areas and interstates providing easy access to Lexington, Winchester and many central Kentucky cities. The interior features freshly updated flooring, offering a cohesive feel to living spaces. The true highlight of this property is

  

  Brenda Sipes

  WEICHERT REALTORS - ABG Properties

  (859) 328-1402

  113 Mimosa Dr, Winchester, KY 40391
• Explore Winchester

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  /7

  $440,000

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft

  870 Pilot View Rd, Winchester, KY 40391

  Welcome to your own slice of paradise! This 2022 doublewide sits on an impressive 39.5 acres of rolling countryside in Winchester, offering the perfect blend of modern comfort, privacy, and wide-open space. Step outside and take in the beautiful pastures, ideal for horses, cattle, or hobby farming, all complemented by a peaceful creek that winds through the property—perfect for relaxing evenings

  Chelsea Morguson McCallie Real Estate

  870 Pilot View Rd, Winchester, KY 40391
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  /26

  $425,000

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft

  4305 Old Boonesboro Rd, Winchester, KY 40391

  

  Brenda Sipes

  WEICHERT REALTORS - ABG Properties

  (859) 549-3072

  4305 Old Boonesboro Rd, Winchester, KY 40391
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  /17

  $129,900

  • 2 Beds
  • 1 Bath
  • 876 Sq Ft

  122 Calloway St, Winchester, KY 40391

  Investment Opportunity or Perfect Starter Home This charming 2-bedroom, 1-bath property is full of potential! With a strong rental history and an excellent lease track record, it's ideal for investors or first-time buyers. Recently vacated, the home requires only light maintenance, and the seller is even willing to fund minor repairs. Don't miss your chance to own a property with great value and

  Darrell Tackett Dream Maker Realty, LLC

  122 Calloway St, Winchester, KY 40391
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  /24

  $290,000

  • 12 Beds
  • 4 Baths
  • 4,010 Sq Ft

  149 Winn Ave, Winchester, KY 40391

  Welcome to this quad plex income producing property. It is a large lot and the property sits back on the lot away from the road. There are 4 units, each with 3 beds and 1 bath. The whole building has a total of bedrooms of 12 beds and 4 baths. Each unit has its own kitchen. The pictures are of the only vacant unit on the bottom left. The two lower units rent for $950 and $925. The upper units

  Libby VanMeter Marshall Lane Real Estate - Lexington

  149 Winn Ave, Winchester, KY 40391
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  /2

  $110,000

  • Land
  • 0.47 Acre
  • $234,043 per Acre

  139 Jacob Ct, Winchester, KY 40391

  Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

  John Wilson Bluegrass Properties Group

  139 Jacob Ct, Winchester, KY 40391
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  /2

  $150,000

  • Land
  • 2.11 Acres
  • $71,090 per Acre

  125 Knox Ct, Winchester, KY 40391

  Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

  John Wilson Bluegrass Properties Group

  125 Knox Ct, Winchester, KY 40391
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  /2

  $110,000

  • Land
  • 0.32 Acre
  • $343,750 per Acre

  250 Duclair Dr, Winchester, KY 40391

  Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

  John Wilson Bluegrass Properties Group

  250 Duclair Dr, Winchester, KY 40391
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  /13

  $1,250,000

  345 Providence Ln, Winchester, KY 40391

  120 Acres of Scenic Farmland in Winchester, KY. Discover the beauty and tranquility of country living on this remarkable 120-acre farm nestled in the heart of Clark County, Kentucky. Featuring a picturesque mix of rolling pastureland, mature woodlands, and pond, this property offers endless possibilities for farming, livestock, recreation, or building your dream home. Conveniently located just

  Megan McCoy Keller Williams Legacy Group

  345 Providence Ln, Winchester, KY 40391
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  /2

  $150,000

  • Land
  • 2.16 Acres
  • $69,444 per Acre

  120 Knox Ct, Winchester, KY 40391

  Looking for a place to build a Upscale home in Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

  John Wilson Bluegrass Properties Group

  120 Knox Ct, Winchester, KY 40391
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  /47

  $452,500

  • 3 Beds
  • 2.5 Baths
  • 2,961 Sq Ft

  42 Mockingbird Valley Rd, Winchester, KY 40391

  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

  Markus Cross McCallie Real Estate

  42 Mockingbird Valley Rd, Winchester, KY 40391
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  /2

  $110,000

  • Land
  • 0.27 Acre
  • $407,407 per Acre

  125 Jacob Ct, Winchester, KY 40391

  Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

  John Wilson Bluegrass Properties Group

  125 Jacob Ct, Winchester, KY 40391
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  /24

  $275,000

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft

  120 Sunset Heights, Winchester, KY 40391

  Your search is over with this hard to find 3 bedroom 2 bathroom ranch located close to town, College Park and featured a nice fenced level yard. Your will love the cathedral ceiling in the Great Room and Kitchen as well as the above ground pool with a new liner ready to be installed. You will love the oversized rear deck which will be great for entertaining. A covered front porch as well as

  Keith Wilson Coldwell Banker McMahan

  120 Sunset Heights, Winchester, KY 40391
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  /2

  $110,000

  • Land
  • 0.32 Acre
  • $343,750 per Acre

  115 Jacob Ct, Winchester, KY 40391

  Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

  John Wilson Bluegrass Properties Group

  115 Jacob Ct, Winchester, KY 40391
• 

  /2

  $110,000

  • Land
  • 0.5 Acre
  • $220,000 per Acre

  260 Duclair Dr, Winchester, KY 40391

  Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

  John Wilson Bluegrass Properties Group

  260 Duclair Dr, Winchester, KY 40391
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  /2

  $100,000

  • Land
  • 0.68 Acre
  • $147,059 per Acre

  100 Duclair Dr, Winchester, KY 40391

  Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

  John Wilson Bluegrass Properties Group

  100 Duclair Dr, Winchester, KY 40391
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  /7

  $190,000

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

  41 7th St, Winchester, KY 40391

  Welcome to 41 7th Street! This all-brick ranch features 3 bedrooms, 2 full baths, and beautiful hardwood floors throughout the living room, hallway, and bedrooms. Tucked at the end of the street, the property offers added privacy and peaceful farm views behind the home. Enjoy newer windows, a new HVAC system, and a new water heater for added comfort and efficiency. The attached garage provides

  Austina Bruton Re/Max Elite Realty - Hamburg

  41 7th St, Winchester, KY 40391
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  /34

  $325,000

  • 4 Beds
  • 3 Baths
  • 1,776 Sq Ft

  213 Orchid Ct, Winchester, KY 40391

  Kasey McCarty 5.23 Real Estate

  213 Orchid Ct, Winchester, KY 40391
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  /33

  $367,000

  • 4 Beds
  • 2.5 Baths
  • 2,811 Sq Ft

  446 Tremont Ln, Winchester, KY 40391

  Are your ready for a lifestyle change? Do you need more space? How about approximately 2800 square feet with four bedrooms and 2-1/2 baths. A nice size corner lot with side entry 2 car garage. Walkout patio, walk in closet, two story entry and gas fireplace are just a few of the features in this home. Recent upgrades include TWO new hot water heaters, UV filtration installed in HVAC, Full privacy

  Dylan Langdon The Agency

  446 Tremont Ln, Winchester, KY 40391
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  /62

  $259,500

  • 3 Beds
  • 2 Baths
  • 1,247 Sq Ft

  3614 Stamper Dr, Winchester, KY 40391

  Fully renovated to perfection, this exceptional home showcases high-end upgrades throughout. Enjoy newly installed windows, doors, and sleek flooring, all complemented by modern appliances and updated cabinetry. A brand-new deck creates the perfect spot for outdoor relaxation, while the freshly built storage building out back adds extra convenience. The attached garage offers attic access with

  Darrell Tackett Dream Maker Realty, LLC

  3614 Stamper Dr, Winchester, KY 40391
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  /70

  $335,000

  • 6 Beds
  • 4 Baths
  • 3,544 Sq Ft

  297 S Main St, Winchester, KY 40391

  Completely remodeled duplex offering over 3,400 sq. ft. of living space! Featuring 6 bedrooms and 4 bathrooms, this property has been fully updated with granite countertops, new appliances, fresh flooring, and paint throughout. The layout is bright and inviting with plenty of natural light. Enjoy the covered front porch, separate utility room, and unfinished basement for extra storage or future

  Silvia Torres Tru Life Real Estate

  297 S Main St, 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
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  /21

  $139,000

  • 2 Beds
  • 1 Bath
  • 886 Sq Ft

  9 Linden Ave, Winchester, KY 40391

  Back on Market due to: Buyer's financing fell through. Very nice home with hardwood floors in main areas featuring 2 bedrooms, 1 bath, permanent stairs to attic that has windows and could possibly be 2 bedrooms or bonus room. Enjoy your coffee on the front porch in the mornings! The storage shed in the back yard conveys with property. Home being sold as-is, where-is, sale pending court approval,

  Emily Hacker-Todd CENTURY 21 Advantage Realty

  9 Linden Ave, Winchester, KY 40391
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  /43

  $269,900

  • 7 Beds
  • 3 Baths
  • 3,393 Sq Ft

  146 W Lexington Ave, Winchester, KY 40391

  This investment property has strong rent potential to add to your portfolio. Property is conveniently located in the heart of Downtown Winchester and is zoned R-4. There's a great opportunity to use this property for house hacking -- leverage your money by living in one unit and renting out the other! Downstairs unit has 4 bedrooms and 2 full bathrooms, and its currently leased for $1,495 a

  Kevin Bradley KB Realty Group

  146 W Lexington Ave, Winchester, KY 40391
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  /86

  $550,000

  • 4 Beds
  • 3.5 Baths
  • 3,848 Sq Ft

  125 Casa Landa Way, Winchester, KY 40391

  Stoney Brook Subdivision! Second time ever offered for sale. Beautiful two story brick home with first and second floor en-suites. Each of the 4 bedrooms has its own walk in closet. Formal family room and dinning rooms, great room with fireplace, breakfast area, all season room with natural lighting, and large flex space located on second floor. All of this setting on .40 of an acre lot with side

  Maggie Napier Napier Realtors

  125 Casa Landa Way, Winchester, KY 40391
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  /2

  $550,000

  • Land
  • 1.53 Acres
  • $359,477 per Acre

  33-41 Winn Ave, Winchester, KY 40391

  Discover a rare opportunity in downtown Winchester with this assemblage of four vacant lots being sold together as a single offering. Zoned L1 and totaling approximately 1.53 acres, this property presents exceptional potential for redevelopment, infill housing, multiunit residential, mixeduse, or commercial concepts in a central location. Situated just steps from local shops, restaurants,

  Bob Sophiea eXp Realty, LLC

  33-41 Winn Ave, Winchester, KY 40391
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  /23

  $250,000

  • 3 Beds
  • 2 Baths
  • 1,518 Sq Ft

  313 S Burns Ave, Winchester, KY 40391

  This 3 bedroom, 2 bath home sits on a corner lot with hardwood floors and a two-car detached garage behind the home. Plus, it's walkable to downtown Winchester, the public library, and College Park. Inside, you'll find tall ceilings, a traditional living and dining room, and a unique layout that gives you options for how you use the space. The kitchen opens to the back deck, and a ramp at the

  Michelle Blackburn RE/MAX Creative, Winchester

  313 S Burns Ave, Winchester, KY 40391
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  /31

  $295,000

  • 3 Beds
  • 3 Baths
  • 1,738 Sq Ft

  420 Willowbrook Rd, Winchester, KY 40391

  Tucked near the cul-de-sac on a dead-end street in the Windridge neighborhood, this 3 bedroom, 3 bath ranch offers easy access to the Bypass and Boone Ave along with a functional, spacious layout. A foyer entry opens to a formal living room featuring a wood-burning fireplace, built-in shelving, and a charming cased opening that provides sightlines into the kitchen and dining area, while a den

  Michelle Blackburn RE/MAX Creative, Winchester

  420 Willowbrook Rd, Winchester, KY 40391
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  /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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  /59

  $825,000

  • 2 Beds
  • 1.5 Baths
  • 2,361 Sq Ft

  455 Davis Ln, Winchester, KY 40391

  Hunter's Paradise! This beautiful 85 acre farm is nestled in the heart of Clark County. Wildlife is abundant as you travel throughout the property. The home is very spacious with a full mother in law suite. Entertain friends at the full bar, while enjoying the wood burning stove. A functioning greenhouse expands the possibilities for year round gardening. If you are looking for little piece of

  Dale Hatton Dream Maker Realty, LLC

  455 Davis Ln, Winchester, KY 40391
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  /65

  $609,900

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

  6595 Mount Sterling Rd, Winchester, KY 40391

  INCREDIBLE! This custom-built home sits on 2.59 acres in a prime location just minutes from I-64 and perfectly positioned between Winchester and Mount Sterling. The main level features a grand formal dining room, a family room with a vaulted coffered ceiling, and an eat-in kitchen open to the living area for easy entertaining. You'll also find the first primary suite plus two additional bedrooms

  Brooke Otis Mullins RO&CO Real Estate

  6595 Mount Sterling Rd, Winchester, KY 40391
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  /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
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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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  /49

  $450,000

  • 3 Beds
  • 2.5 Baths
  • 2,258 Sq Ft

  233 Cunningham Ln, Winchester, KY 40391

  Mini Farm Alert! This fabulous homestead is located less than 2 miles off the Mountain Parkway making it easily accessible. One level, ranch home that features 3 bedrooms, a luxurious primary ensuite... corner jetter tub, seperate walk in shower with glass door, double bowl raised height vanity and a linen closet complete the bathroom and the bedroom has vaulted ceilings, walk in closet and

  Amanda Marcum Berkshire Hathaway HomeServices Foster Realtors

  233 Cunningham Ln, Winchester, KY 40391
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  /28

  $309,900

  • 3 Beds
  • 3.5 Baths
  • 2,526 Sq Ft

  24 N Burns Ave, Winchester, KY 40391

  Historic charm with all the modern amenities! An inviting front porch and entry lead to a welcoming space warmed by refinished original hardwood floors and a new electric fireplace. Other updates include a brand-new kitchen with granite countertops and new appliances, new lighting fixtures, tile in the foyer and bathrooms, new roof, new plumbing, new electrical, new HVAC, new windows, new spray

  Sarah Hess Keller Williams Commonwealth

  24 N Burns Ave, Winchester, KY 40391
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  /39

  $384,900 New Construction

  • 4 Beds
  • 4.5 Baths

  3600 Crowe Ridge Rd, Winchester, KY 40391

  Newly constructed unfinished multigenerational home located on 4 acres. Separate level living with 2 kitchens, 2 laundry rooms, and an en-suite for every bedroom. The main floor features 21' cathedral ceilings, 8' doors and 15 3'x6' windows creating a spacious home boasting panoramic views. Includes an additional 20'x24' loft space and 2 flex rooms with ANSI standard windows. Secondary living

  Maggie Napier Napier Realtors

  3600 Crowe Ridge Rd, 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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  /26

  $255,000

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

  21 Virginia Ave, Winchester, KY 40391

  Nicely updated and offering plenty of functional space, this home gives you flexibility and room to grow. The main living area flows into an updated kitchen featuring modern finishes, new appliances, butcher-block countertops, and convenient access to the sunroom. Enjoy your morning coffee in the oversized sunroom, then step out to the fully fenced backyard — great for chickens, kids, pets,

  Emily Crump EXP Realty, LLC

  21 Virginia Ave, Winchester, KY 40391
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  /19

  $199,900

  • 3 Beds
  • 2 Baths
  • 1,072 Sq Ft

  117 Buffalo Trace, Winchester, KY 40391

  Move-In Ready! 3 bedrooms, 2 bath, brand new kitchen cabinets with stylish butcher block counter tops, fresh light fixtures throughout, and durable, sleek laminate flooring. This home combines comfort and style with updates that make it truly shine. Perfect for families or first-time home buyers! Conveniently located in a great neighborhood. Owner/Agent

  Nena Honaker Tom Goebel & Company

  117 Buffalo Trace, Winchester, KY 40391
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  /42

  $349,900

  • 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. 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 laminate floors and a brick fireplace; the perfect place to

  Josh Wood Freedom Realty & Property Management

  3622 Stamper Dr, Winchester, KY 40391

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