Newest Homes for Sale in Winchester, KY

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  /32

  $275,000 Open Sat 1PM - 3PM

  • 3 Beds
  • 2.5 Baths
  • 1,550 Sq Ft

  192 Prescott Ln, Winchester, KY 40391

  Welcome to this lovely move in ready gem. Perfectly positioned just off the Winchester Bypass. Whether you are commuting or looking for quick access to local shopping and dining, this location offers the perfect balance of connectivity and suburban quiet. Step through the front door and you will love the grandeur of the two-story living room and stairway and the additional accents of the

  Joy Murphy United Real Estate Bluegrass

  192 Prescott Ln, Winchester, KY 40391
• Explore Winchester

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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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  /4

  $137,500

  • Land
  • 3.94 Acres
  • $34,898 per Acre

  150 Spencer Ln, Winchester, KY 40391

  Build your dream home in the stunning ESKIPPAKITHIKI OVERLOOKS! Looking for your next investment? This 3.940 acre parcel offers unlimited potential-whether you dream of building or simply holding land as it grows in value. Offering unparalleled views of a serene, natural setting. Perfect for a private retreat or family estate, this property invites you to design your ideal lifestyle surrounded by

  Kathryn Cheuvront Coldwell Banker McMahan

  150 Spencer Ln, Winchester, KY 40391
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  /36

  $435,000

  • 4 Beds
  • 2 Baths
  • 1,692 Sq Ft

  3886 Jackson Ferry Rd, Winchester, KY 40391

  Take in the scenery, enjoy the quite county life, sitting on 5 acres, this brick ranch home offers easy living and peaceful country life. Four Bedrooms 2 full updated baths, Primary Suite with walk in closet, hardwood floors, beautiful brick fireplace in Living Room with Vaulted ceiling and built in shelving, Dining Room, Kitchen with breakfast area granite counter tops and all appliances (range,

  Whitney Ensor Ensor Real Estate, LLC

  3886 Jackson Ferry Rd, Winchester, KY 40391
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  /15

  $925,000

  • Land
  • 3.77 Acres
  • $245,358 per Acre

  300 Rolling Hills Ln, Winchester, KY 40391

  Great location just off exit 96 on I-64 and easy access to the Mountain Parkway. Only 15 minutes from I-75. Located near the entrance to the Winchester Kentucky Industrial Park. 3.774 flat acres to build your next business location.

  Josh Wood Freedom Realty & Property Management

  300 Rolling Hills Ln, Winchester, KY 40391
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  /14

  $189,999

  • 3 Beds
  • 1 Bath
  • 950 Sq Ft

  41 Hiawatha Trail, Winchester, KY 40391

  Investor Special with Charm & Potential! Don't miss this opportunity to bring new life to this adorable brick home full of character and promise! Featuring beautiful hardwood floors, timeless curb appeal, and a layout ready to shine again, this property is the perfect canvas for your next project. Whether you're an investor, flipper, or buyer looking to build equity, this home offers classic

  Hannah Toole Coldwell Banker McMahan

  41 Hiawatha Trail, Winchester, KY 40391
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  /31

  $204,900

  • 3 Beds
  • 1 Bath
  • 1,290 Sq Ft

  60 Hiawatha Trail, Winchester, KY 40391

  Updated, affordable, and ready for you! This 3-bedroom, 1-bath home offers approximately 1,300 square feet of comfortable living space with tasteful updates that make it easy to move right in. The layout provides a welcoming feel with bright living areas and an updated kitchen and bath. Downstairs you have a possible 4th bedroom or office space. Conveniently located in Winchester close to

  Christina Bucher Keller Williams Legacy Group

  60 Hiawatha Trail, Winchester, KY 40391
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  /71

  $799,000

  • 4 Beds
  • 2.5 Baths
  • 7,058 Sq Ft

  186 Chardonnay Ct, Winchester, KY 40391

  Fontaine Estates, a great place to call home. This spacious 4 bedroom 3 bath property offers an abundance of storage,, including charming window seats. Enjoy the convenience of an oversized driveway and garage, along with a beautifully designed outdoor setting, feauring a fire pit and a dedicated entertainment space. The thoughtfully planned, custom designed landscaping enhances the home's curb

  

  Brenda Sipes

  WEICHERT REALTORS - ABG Properties

  (859) 470-2071

  186 Chardonnay Ct, Winchester, KY 40391
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  /28

  $799,900

  • Land
  • 13.19 Acres
  • $60,644 per Acre

  1600 Ironworks Rd, Winchester, KY 40391

  This property has it all! Easy access to Veterans Memorial Bypass, I-64, and downtown Winchester, plus entrances on Ironworks and clear visibility from the Bypass. This does have sewer and water located on the property. Full of potential possibilities zoned Planned Development and more acreage is available if needed. The property access is a driveway off Ironworks Road across from Center Drive

  Josh Wood Freedom Realty & Property Management

  1600 Ironworks Rd, Winchester, KY 40391
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  /16

  $179,900

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

  47 Buckner St, Winchester, KY 40391

  This 3-bedroom, 2 full bath home is nestled in a convenient location and ready for new owners. Updates can be admired throughout. Property boats spacious bedrooms including primary bedroom with on-suite, large back yard with garage and so much more. Schedule your showing today!

  Michael Hilario The Agency

  47 Buckner St, Winchester, KY 40391
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  /11

  $50,000

  • Land
  • 0.41 Acre
  • $121,951 per Acre

  308 Duclair Dr, Winchester, KY 40391

  Tucked away on a quiet cul-de-sac in Mallard Place, this .41-acre lot is ready for your vision. Imagine your dream home in a neighborhood known for its charm and convenience. Bring your house plans—your future starts here!

  Joseph Miller Keller Williams Legacy Group

  308 Duclair Dr, Winchester, KY 40391
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  /13

  $246,400

  • 5 Beds
  • 3 Baths
  • 3,007 Sq Ft

  221 S Highland St, Winchester, KY 40391

  INVESTOR SPECIAL, You have the opportunity to purchase a fully occupied tri-plex in the heart of Winchester with instant cash flow. Main level unit is a large 2 bed, one bath. Upstairs unit is also a 2 bed, one bath, and lower level is a 1 bed, one bath unit. There is street parking and alley access with parking in the rear. All units have their own exterior entrance. Some utilities are metered

  Joshua Lynch The Brokerage

  221 S Highland St, Winchester, KY 40391
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  /52

  $339,900

  • 4 Beds
  • 2 Baths
  • 1,843 Sq Ft

  228 Holiday Rd, Winchester, KY 40391

  Don't miss your chance to own this beautifully updated split-level home in Holiday Hills! Featuring 4 bedrooms and 2 full baths, this home offers a bright, open-concept kitchen and living area perfect for both everyday living and entertaining. Thoughtfully updated in recent years, the home features newer flooring, fresh paint, updated cabinets and countertops, modern electrical and plumbing

  Caroline Mucci CENTURY 21 Commonwealth R E

  228 Holiday Rd, Winchester, KY 40391
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  /15

  $139,000

  • 2 Beds
  • 1 Bath
  • 904 Sq Ft

  37 Ashland Ave, Winchester, KY 40391

  Ideal for first-time buyers, downsizers, or investors. This move-in ready 2-bedroom home features a fenced backyard, off-street parking, and a detached storage building, all in a convenient Winchester location.

  Samantha Gray National Real Estate

  37 Ashland Ave, Winchester, KY 40391
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  /59

  $695,000

  • 3 Beds
  • 4 Baths
  • 4,008 Sq Ft

  1775 Irvine Rd, Winchester, KY 40391

  Absolutely fabulous all brick home with incredible views, one owner, what makes this home special is the feeling of elegance, a total renovation offers the ultimate in living, spacious lower level provides full bath, family room, firepalce, walk out door to a large patio, first level dining room, great room with firepalce, showcase kitchen, living room, upstairs with large master suite, side

  Mila Ensor Ensor Real Estate, LLC

  1775 Irvine Rd, Winchester, KY 40391
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  /43

  $559,000

  • 4 Beds
  • 4.5 Baths
  • 4,185 Sq Ft

  556 Earlymeade Dr, Winchester, KY 40391

  As you walk in the front door of this house you will immediately be thrilled because the owners have loved this house and this is evident from the gleaming hardwood floors to the fresh coats of paint. This house is located in the most desirable neighborhood of Earlymeade. It is near lots of popular destinations, including Hamburg in Lexington and the I-64 and I-75 corridors so you can be in

  Craig Bridgewater Bridgewater Real Estate

  556 Earlymeade Dr, Winchester, KY 40391
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  /36

  $225,000

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft

  415 L East Junction Rd, Winchester, KY 40391

  Tucked away on just under 3 peaceful acres in Winchester, this charming 3-bedroom, 2-bath manufactured home on a permanent foundation offers the perfect blend of comfort and country living. Enjoy the privacy and space you've been looking for, with a beautiful creek running along the back of the property—creating a serene backdrop for relaxing evenings or outdoor entertaining. Inside, you'll find

  Rachel Rainey Kentucky Land and Home

  415 L East Junction Rd, Winchester, KY 40391
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  /30

  $200,000

  • 3 Beds
  • 2 Baths
  • 1,289 Sq Ft

  128 Bay Hill Dr, Winchester, KY 40391

  Opportunity knocks in Royal Oaks Village—be part of Winchester's next chapter. Located within the expanding Deerlawn development, this single-story ranch townhome offers incredible upside in an area poised for growth. With future plans bringing hundreds of new homes, townhomes, and duplexes nearby, this is your chance to get in early and build equity. Inside, you'll find a spacious and functional

  Melia Hord Keller Williams Legacy Group

  128 Bay Hill Dr, Winchester, KY 40391
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  /15

  $139,900

  • 2 Beds
  • 1 Bath
  • 986 Sq Ft

  174 Cook Ave, Winchester, KY 40391

  Charming Fixer-Upper with Endless Potential - Priced to Sell!! This older gem is full of character and opportunity! Featuring solid bones and classic charm, this property is perfect for buyers with a vision who are not afraid to add a little TLC! Whether you're an investor, DIY entusiast, or someone dreaming of restoring a home to its former glory, this is your chance to build equity and create

  A. Rebecca Woods Woods Realty Group

  174 Cook Ave, Winchester, KY 40391
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  /4

  $10,000

  • Land
  • 0.17 Acre
  • $59,880 per Acre

  117 4th St, Winchester, KY 40391

  Discover the potential of this spacious 0.17-acre residential property nestled in a neighborhood community on clear and level vacant lot located in a Cul-de-sac of Lincoln Park Subdivision. This could be an investment opportunity as well, for ideal savvy investors looking to diversify your portfolio this property would be perfect for building a custom home, holding for future value, or develop

  Anita McDermott Keller Williams Bluegrass Realty

  117 4th St, Winchester, KY 40391
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  /24

  $265,000

  • 3 Beds
  • 2 Baths
  • 1,304 Sq Ft

  201 Prescott Ln, Winchester, KY 40391

  This Is The One You Have Been Waiting For!!! Perfect Location, Flat Fully Fenced Backyard And A Large Rear Covered Patio. This 1 1/2 Story 3 Bedroom 2 Bath Home Has Vaulted Ceilings; Lots Of Cabinets; Stainless ' Steel Appliances; Good Size Primary Bedroom With En Suite; Walk In Closet; 2 More Generous Sized Bedrooms And So Much More!

  Patrick Arvin Keller Williams Commonwealth

  201 Prescott Ln, Winchester, KY 40391
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  /31

  $155,000

  • 3 Beds
  • 1 Bath
  • 1,160 Sq Ft

  730 Byrd Ave, Winchester, KY 40391

  Full of opportunity on a large lot! With mostly cosmetic updates needed, this is an ideal project for a flip or a rental refresh. The layout and lot size provide flexibility, and this property has excellent potential to add value quickly. Being sold as-is.

  Patricia Weiderman Kentucky Land and Home

  730 Byrd Ave, Winchester, KY 40391
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  /60

  $379,900

  • Land
  • 51.04 Acres
  • $7,444 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
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  /52

  $275,000

  • 4 Beds
  • 2 Baths
  • 2,417 Sq Ft

  104 Jackson Ferry Rd, Winchester, KY 40391

  Located in Winchester, this 4-bedroom, 2-bath home offers approximately 2,417 square feet of living space with room to spread out both indoors and out. The home features a spacious living room with a fireplace, providing a comfortable central gathering area. Multiple bedrooms offer flexibility for guests, home office space, or changing household needs. Recent updates include a renovated kitchen

  Bob Sophiea eXp Realty, LLC

  104 Jackson Ferry Rd, Winchester, KY 40391
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  /12

  $160,000

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft

  471 Goose Creek Rd, Winchester, KY 40391

  CASH BUYERS! This 3-bedroom, 2-bath manufactured home on 1.49 acres offers strong potential for those looking to renovate, rent, or resell. Property is being sold as-is and will require repairs, making it best suited for cash buyers. Located just minutes from I-64 and convenient to Lexington, this property combines rural privacy with accessibility — a desirable combination for future resale or

  Shari Frasure Keller Williams Commonwealth

  471 Goose Creek Rd, Winchester, KY 40391
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  /29

  $234,900

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft

  11 Shelley Dr, Winchester, KY 40391

  SELLER is motivated to offers! Welcoming you to this lovely updated throughout 3 bedroom, 2 full bath ranch! As you step into the home with its cozy feeling, and spacious space in every room, including a full unfinished basement wonderful for storage or to finish that into living square footage, great size back yard with large back patio perfect for the family gatherings, also a partial fenced in

  Nichole Bingham CENTURY 21 Advantage Realty

  11 Shelley Dr, Winchester, KY 40391
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  /13

  $130,000

  • 2 Beds
  • 1 Bath
  • 1,254 Sq Ft

  208 4th St, Winchester, KY 40391

  Discover the potential of this spacious 0.27-acre residential home nestled in a neighborhood community on clear and level land located in a Cul-de-sac of Lincoln Park Subdivision. This Property features 2-bedrooms, 1-Bathroom, a large family room with a fireplace. There is also a large versatile barn on the property as well. This could be an investment opportunity as well, for ideal savvy

  Anita McDermott Keller Williams Bluegrass Realty

  208 4th St, Winchester, KY 40391
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  /2

  $67,500

  • Land
  • 1.89 Acres
  • $35,695 per Acre

  250 Spencer Ln, Winchester, KY 40391

  Unique triangular shaped lot in a wooded rural setting, interesting opportunities for privacy in a beautiful area of Clark County where you can enjoy the outdoors and create memories galore.

  Craig Bridgewater Bridgewater Real Estate

  250 Spencer Ln, Winchester, KY 40391
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  /3

  $84,900

  • Land
  • 3.39 Acres
  • $25,044 per Acre

  160 Rector Ln, Winchester, KY 40391

  UNIQUE Opportunity - 3.39 acres with a small pond - tucked away on a private lane, flat land and totally surrounded by trees. What a unique setting!! Convenience is the key to this property. Water is available at the main road. Internet has been extended down Rector Lane, electricity is accessible for connection. Deed Restrictions apply. Do Not Miss Your Chance to own this SPECIAL piece of land.

  M Gail Cleaver United Real Estate Bluegrass

  160 Rector Ln, Winchester, KY 40391
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  /28

  $235,000

  • 4 Beds
  • 2 Baths
  • 1,431 Sq Ft

  13 Arlington Rd, Winchester, KY 40391

  One Level Living!!!! This home boasts all the curb appeal with new vinyl siding, new roof and new leaf filter gutter system on home all in 2025!! A vinyl style privacy fenced in back yard, mature trees and beautiful landscaping! 4 bedrooms, 2 full bathrooms, Kitchen with all appliances (range, dishwasher, refrigerator, microwave) with updated flooring! Hardwood floors are showcased in the main

  Whitney Ensor Ensor Real Estate, LLC

  13 Arlington Rd, Winchester, KY 40391
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  /63

  $460,000

  • 3 Beds
  • 2 Baths
  • 1,288 Sq Ft

  1911 Trapp-Goffs Corner Rd, Winchester, KY 40391

  Enjoy peaceful country living on 17 beautiful acres in Clark County! This 3-bedroom, 2-bath ranch home sits on a scenic stretch of Trapp-Goffs Corner Road and offers the perfect blend of privacy, space, and convenience just minutes from Winchester and an easy drive to Lexington. The home features comfortable main-level living with a functional layout and a partially finished basement that

  Cheri Shaffer Lifstyl Real Estate

  1911 Trapp-Goffs Corner Rd, Winchester, KY 40391
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  /24

  $225,000

  • Land
  • 24 Acres
  • $9,375 per Acre

  3934 Trapp-Goffs Corner Rd, Winchester, KY 40391

  Wonderful 24 acre retreat with gentle sloping land, and a creek bed running thru part of the front portion of the lots (6.1 acre parcel & 18.4 acre parcel at the rear). Build your dream home or just use as recreational or farm land until you do. 1 1/2 miles to the first exit on the Mountain Parkway exit #10. 12 miles to I-64 at Winchester. See attached pictures & plat/overhead pictures.

  Travis Emnett Top Ten Realty

  3934 Trapp-Goffs Corner Rd, Winchester, KY 40391
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  /76

  $149,000

  • 2 Beds
  • 2 Baths
  • 1,360 Sq Ft

  404 Mount Vernon Dr, Winchester, KY 40391

  Ready to Stop Renting? Your Opportunity Is Here Step into the comfort and freedom of homeownership with this spacious, well maintained 2-bedroom, 2-bath modular home — and yes, the lot is included. An attached room addition provides even more flexibility, easily adaptable into a third bedroom, home office, hobby room, or bonus space to suit your lifestyle. --- Interior Highlights • 2 full

  Darrell Tackett Dream Maker Realty, LLC

  404 Mount Vernon Dr, Winchester, KY 40391
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  /43

  $269,000

  • 3 Beds
  • 2 Baths
  • 1,960 Sq Ft

  564 Trapp-Goffs Corner Rd, Winchester, KY 40391

  Private 12-Acre Property in Winchester, KY - Convenient to Lexington & Red River Gorge This 3-bedroom, 2-bath single-family home with an office/flex room is situated on 12 acres in Winchester, KY, offering a combination of open and primarily wooded land. The property is located less than 40 minutes from Lexington and approximately 30 minutes from Red River Gorge. The home offers 1,960 square feet

  Felicia Mayes The Real Estate Co.

  564 Trapp-Goffs Corner Rd, Winchester, KY 40391
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  /13

  $1,115,000

  • Land
  • 120 Acres
  • $9,292 per Acre

  345 Providence Ln, Winchester, KY 40391

  Rare opportunity to own approximately 120 acres of beautiful rolling farmland in Clark County! This versatile property offers a mix of cleared pasture and wooded acreage, ideal for cattle, horses, recreation, or your dream farmstead. Including a large pond plus county water available at the road this property is well-suited for agricultural use. The land is gently rolling with scenic views and

  Megan McCoy Keller Williams Legacy Group

  345 Providence 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

  Sellers have current accepted offer in place with a 48-hour kick-out clause.

  Brooke Otis Mullins RO&CO Real Estate

  6595 Mount Sterling Rd, Winchester, KY 40391
• 

  /2

  $188,500

  • Land
  • 12.1 Acres
  • $15,579 per Acre

  155 Spring Ridge Way, Winchester, KY 40391

  Great opportunity to develop/ build on 12+ acres. The property has three street stubs adjoining it. Three different concepts are included under documents. They are- R-1E, 4000 sq. Ft lots for 80 lots R-4- 14 Duplexes and 6 4plexes for 52 units R-1D - 6000 sq. Ft. Lots for 41 lots. Utilities are to the property and sewer availability should not be an issue. Please feel free to call the listing

  Jo Gawthrop Keller Williams Bluegrass Realty

  155 Spring Ridge Way, Winchester, KY 40391
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  /5

  $575,000

  • Land
  • 1.71 Acres
  • $336,257 per Acre

  1025 Colby Rd, Winchester, KY 40391

  This 1.7+/- acre parcel represents an excellent opportunity for almost any commercial application. The property has 397 feet of frontage along busy Colby Road (9,170 AADT, 2015) near its intersection with the Winchester Bypass (23,200 AADT, 2011). Located in the main shopping corridor of Clark County, this property receives tons of exposure and traffic from the adjacent Walmart Super-center,

  Jo Gawthrop Keller Williams Bluegrass Realty

  1025 Colby Rd, Winchester, KY 40391
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  /34

  $255,000

  • Land
  • 6.08 Acres
  • $41,941 per Acre

  190 Privacy Ln, Winchester, KY 40391

  6.08 acres settled in Clark County with access from both Privacy Ln and Little Stoner Rd. This property boasts a 30x56 with 10 foot wall Kentucky Steel Truss building with concrete floors, gas and wood burning heat, full bath, and a car lift. Additionally, there is a barn with a 3 bay shed attached.

  Jason Joseph Keller Williams Commonwealth

  190 Privacy Ln, Winchester, KY 40391
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  /36

  $369,000

  • 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 sought after communities—Shala Mar Estates. This beautifully updated 3-bedroom, 2-bathroom residence offers the perfect blend of comfort, style, and modern convenience. The expansive primary suite is a true retreat, featuring a stunning ensuite bathroom with a brand new soaking tub and a separate tiled shower. Two additional bedrooms provide

  Nena Honaker Tom Goebel & Company

  133 Shala-Mar Rue, Winchester, KY 40391

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