Winchester, KY Homes for Sale

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  $700,000 New Construction

  • 3 Beds
  • 2 Baths
  • 2,400 Sq Ft

  415 Alexis Way, Winchester, KY 40391

  Introducing the Merango, a classic all-brick ranch home designed for both comfort and style. With stunning double front doors and a 2-car attached garage, this home offers incredible curb appeal and modern living. The spacious 3-bedroom, 2-bath layout features a split-bedroom design for added privacy, along with a dedicated study perfect for a home office. The open-concept kitchen is ideal for

  Shane Underwood Keller Williams Commonwealth

  415 Alexis Way, Winchester, KY 40391
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  /60

  $279,950

  • 4 Beds
  • 3 Baths
  • 2,112 Sq Ft

  115 Watercrest Cir, Winchester, KY 40391

  Stunning Home in One of the Area's Most Coveted Neighborhoods!Experience spacious living with 3 generous bedrooms and 2 full baths on the main level, designed for comfort and everyday convenience. The walkout basement offers even more space with a large bedroom and an additional full bath, ideal for guests, extended family, or a private retreat. What truly sets this home apart? The sellers are

  Darrell Tackett Dream Maker Realty, LLC

  115 Watercrest Cir, Winchester, KY 40391
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  /13

  $400,000

  • Land
  • 2.19 Acres
  • $182,648 per Acre

  145 Codella Dr, Winchester, KY 40391

  Great opportunity to buy and build just off the Winchester Bypass. This property is nicely located in the midst of a great deal of new development including a brand new, state-of-the-art CHI Saint Joseph Health Center. Other new development in the immediate area includes Zips Car Wash and Domino's Pizza. Additionally, Walmart and Kroger are located directly across the Bypass from this site. See

  Greg Leveridge Block + Lot Real Estate

  145 Codella Dr, 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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  /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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  /65

  $799,900

  • 2 Beds
  • 2.5 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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  /19

  $105,000

  • Land
  • 9.75 Acres
  • $10,767 per Acre

  3759 Jackson Ferry Rd, Winchester, KY 40391

  Tucked along a peaceful, scenic drive, this 9.752-acre tract offers a rare opportunity to own land backing directly to the beautiful Kentucky River. This parcel is the perfect recreational escape-ideal for parking a camper, weekend getaways, or creating your own private retreat. Spend your days kayaking, canoeing, fishing, or paddle boarding right from your property, then unwind surrounded by

  Christa Joynt Keller Williams Commonwealth

  3759 Jackson Ferry Rd, Winchester, KY 40391
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  /12

  $299,900

  • 4 Beds
  • 4 Baths
  • 2,072 Sq Ft

  1128 Dale Dr, Winchester, KY 40391

  Duplex. Both units are being sold together. Great income-producing potential. Each side offers a nice sized vaulted Great room that opens to the kitchen, 2 bedrooms, 1.5 baths, a laundry room, and a 1-car garage. Nice private backyard for side with lots of trees. 1130 has a new HVAC. Selling As Is Inspections Welcome.

  Brian Hatfield Coldwell Banker McMahan

  1128 Dale Dr, Winchester, KY 40391
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  /2

  $110,000

  • Land
  • 0.29 Acre
  • $379,310 per Acre

  160 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

  160 Duclair Dr, Winchester, KY 40391
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  /3

  $645,000 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,526 Sq Ft

  106 Bella Shae Way, Winchester, KY 40391

  Welcome Home to the Claiborne Floor Plan by CP Builders. This stunning 4-bedroom, 2.5-bathroom home offers a luxurious and spacious living experience. The first floor features a magnificent primary suite complete with a spacious ensuite bathroom, a walk-in closet, and direct access to the backyard. The open floor plan seamlessly connects the living, dining, and kitchen areas, creating a warm and

  Shane Underwood Keller Williams Commonwealth

  106 Bella Shae Way, Winchester, KY 40391
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  /6

  $388,000

  • 5 Beds
  • 3 Baths
  • 2,762 Sq Ft

  101 E Lexington Ave, Winchester, KY 40391

  Here's your chance to own a nice investment property. This triplex has a 2 bed 1 bath unit, 2 bed 1 bath unit, and a 1 bed 1 bath unit. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

  David Espinosa Bluegrass Realty Pros, Inc

  101 E Lexington Ave, Winchester, KY 40391
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  /3

  $251,000

  • 6 Beds
  • 3 Baths
  • 2,302 Sq Ft

  133 S Highland St, Winchester, KY 40391

  16 Central Ave, Winchester, KY 40391Prime multi-family investment in a great Winchester location! This 2-story property features two spacious rental units, both offering strong income potential. The first unit includes 3 bedrooms and 2 bathrooms, while the second unit offers 3 bedrooms and 1 bathroom—ideal for accommodating a range of tenant needs. With an established rental history and close

  David Espinosa Bluegrass Realty Pros, Inc

  133 S Highland St, 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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  /12

  $185,900 Open Mon 5PM - 7PM

  • 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

  41 7th St, Winchester, KY 40391
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  /24

  $209,900

  • 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
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  /2

  $110,000

  • Land
  • 0.38 Acre
  • $289,474 per Acre

  120 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

  120 Duclair Dr, Winchester, KY 40391
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  /32

  $249,900

  • 3 Beds
  • 2 Baths
  • 1,656 Sq Ft

  17 Euclid Ave, Winchester, KY 40391

  Welcome home to 17 Euclid Ave in beautiful College Park area of Winchester. This three bedroom two full bath home may be the one you are looking for. Beautiful Hardwood floors throughout most of the home. Two additional bedrooms are upstairs with a full bath. Fenced in back yard and a large deck for you summertime entertaining. Don't wait, let's take a look.

  Donna Thwaites Thwaites Realtors LLC

  17 Euclid Ave, Winchester, KY 40391
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  /62

  $264,900

  • 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
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  /39

  $175,000

  • 2 Beds
  • 1.5 Baths
  • 1,202 Sq Ft

  1494 Amster Grove Rd, Winchester, KY 40391

  Welcome to this charming river front house. Step out your back door and you are immediately at the river. Open floor plan with a wood burning fireplace. Metal cabinets and epoxy floors on the first level are designed to survive in case of a flood. First floor bedroom with enough room for a King sized bed. Upstairs you will find another bedroom and a half bath. Sip your morning coffee on your back

  Libby VanMeter Marshall Lane Real Estate - Lexington

  1494 Amster Grove Rd, Winchester, KY 40391
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  /9

  $102,000

  • 2 Beds
  • 1 Bath
  • 552 Sq Ft

  39 S Highland St, Winchester, KY 40391

  Here's your chance to own a nice investment property. This Single Family home has 2 bedrooms and 1 bath. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

  David Espinosa Bluegrass Realty Pros, Inc

  39 S Highland St, Winchester, KY 40391
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  /12

  $144,000

  • 3 Beds
  • 1 Bath
  • 805 Sq Ft

  150 Cook Ave, Winchester, KY 40391

  Here's your chance to own a nice investment property. This has a single family has 3 bedrooms and 1 bath. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

  David Espinosa Bluegrass Realty Pros, Inc

  150 Cook Ave, Winchester, KY 40391
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  $205,000

  • 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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  /2

  $100,000

  • Land
  • 0.32 Acre
  • $312,500 per Acre

  141 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

  141 Duclair Dr, Winchester, KY 40391
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  /6

  $299,000

  550 E Broadway St, Winchester, KY 40391

  Prime land located on the outskirts of Winchester ready for possible development. Parcel has frontage on both East Broadway and Washington Street. Land is currently zoned A-1. Utilities available. The future awaits!!!

  Keith Wilson Coldwell Banker McMahan

  550 E Broadway St, Winchester, KY 40391
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  /58

  $79,950

  • 2 Beds
  • 1 Bath
  • 825 Sq Ft

  1860 Ford Rd, Winchester, KY 40391

  Freshly cleaned and ready for its next owner, this property offers exceptional potential. The spacious 1,800 sq. ft. block garage provides a solid foundation for countless uses — from a workshop or storage facility to a future business or hobby space. An older trailer is also located on the property. It will require a full renovation or removal, giving you the freedom to redesign the space

  Darrell Tackett Dream Maker Realty, LLC

  1860 Ford Rd, Winchester, KY 40391
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  /12

  $194,000

  • 3 Beds
  • 1 Bath
  • 1,046 Sq Ft

  175 Magnolia St, Winchester, KY 40391

  Two homes on one lot. Informaton in listing is for the home in the front of the lot. Behind this home is a second home consisting of 2 bedrooms, 1, bath, Living room and kitchen. Main home has been completely remodeled but guest home will require major renevations. The home in the front of the property is vacant but there is a tenant in the home in the rear of the property. The lease is month to

  A. Rebecca Woods Woods Realty Group

  175 Magnolia St, Winchester, KY 40391
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  /52

  $199,000

  • 3 Beds
  • 1.5 Baths
  • 1,636 Sq Ft

  334 S Burns Ave, Winchester, KY 40391

  Take a look at the nice price adjustment on this one!!! Great opportunity to own this well loved home in a very convenient location in growing community of Winchester. Lots of character and charm upon entry into the entry foyer with nice staircase, opening to large living room with a lovely mantel. Spacious dining room with built in corner cabinet flows into kitchen with plenty of cabinetry and

  Jeanne Beaven Rector Hayden Realtors

  334 S Burns Ave, Winchester, KY 40391
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  /2

  $100,000

  • Land
  • 0.32 Acre
  • $312,500 per Acre

  129 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

  129 Duclair Dr, Winchester, KY 40391
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  /5

  $70,000

  • Land
  • 1.72 Acres
  • $40,698 per Acre

  12541 Ironworks Rd, Winchester, KY 40391

  Discover the perfect place to build your dream home in Eskippakithiki Overlooks. This beautiful 1.72 acre parcel offers ample space, peaceful surroundings, and stunning natural views. Enjoy the serenity of country living, this land provides an ideal canvas for a custom home or family getaway. Don't miss this opportunity to secure your own piece of paradise.

  Daniela Virguez National Real Estate

  12541 Ironworks Rd, Winchester, KY 40391
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  /2

  $78,500

  • Land
  • 0.22 Acre
  • $356,818 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 Keller Williams Legacy Group

  Lot 4 Plantations Dr, Winchester, KY 40391
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  /24

  $300,000

  • 3 Beds
  • 1.5 Baths
  • 1,500 Sq Ft

  103 Southern Ct, Winchester, KY 40391

  Simply the Best! 3 Bedroom, 1 1/2 bath All Brick ranch home located within walking distance to historic downtown Winchester, Country Club, Middle School, great place to live, you will spend most of your time on the Sunporch off the Kitchen, large lot, many updates, floor, bathrooms, new furnace, fresh paint, don't miss looking at this jewel, call today

  Mila Ensor Ensor Real Estate, LLC

  103 Southern Ct, Winchester, KY 40391
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  $250,000

  • 4 Beds
  • 2 Baths
  • 1,739 Sq Ft

  504 Harvard Dr, Winchester, KY 40391

  A spacious Ranch style home with many recent updates. With 4 bedrooms and 2 bath you'll find plenty of space for the everyone. With new laminate flooring, several new doors, and new paint throughout; this home is move in ready! Other updates include a new shower in the master bath, new microwave, new tile in the Utility room, new island top, new shelving in the walk in closet, and new gutters.

  Justin Lee JL Realty Group, LLC

  504 Harvard Dr, 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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  /89

  $359,900

  • 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
• 

  /2

  $100,000

  • Land
  • 0.32 Acre
  • $312,500 per Acre

  165 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

  165 Duclair Dr, Winchester, KY 40391
• 

  

  /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
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  /16

  $180,000

  • 3 Beds
  • 2 Baths
  • 1,848 Sq Ft

  697 Goose Creek Rd, Winchester, KY 40391

  Enjoy the peace and privacy of country living with this 3 bedroom, 2 bath home situated on 2.61 rural acres. With plenty of space to spread out, this property offers endless potential for those looking to add their personal touch. The home needs a little TLC but provides a solid opportunity for homeowners or investors alike. Whether you're dreaming of a small homestead, garden space, or simply

  R Michelle Rowland-Noble Dream Maker Realty, LLC

  697 Goose Creek 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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  /2

  $110,000

  • Land
  • 0.59 Acre
  • $186,441 per Acre

  255 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

  255 Duclair Dr, Winchester, KY 40391
• 

  

  /10

  $775,000

  • Land
  • 3 Acres
  • $258,333 per Acre

  609 Bullion Blvd Unit 3A, Winchester, KY 40391

  Ideally located along the heart of Bypass Road (ADT: 24,801) in Winchester, Kentucky between and surrounding Kroger and Walmart shopping centers. These lots are offered as 1+ acres and may be subdivided. Winchester, KY is the county seat of Clark County, KY and is part of the Lexington-Fayette KY Metropolitan Statistical Area, and is supported by such industries such as Amazon, Ale-8-One, and

  Greg Leveridge Block + Lot Real Estate

  609 Bullion Blvd Unit 3A, Winchester, KY 40391

Showing Results 161 - 200, Page 5 of 6