Winchester, KY Homes for Sale with Acreage

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  /18

  $579,000

  • 5 Beds
  • 3 Baths
  • 3,102 Sq Ft

  110 White Conkwright Rd, Winchester, KY 40391

  Brick ranch with 3 upstairs bedrooms and 2 bedrooms in your mother in law suite and full finished basement, complete with kitchen. 2 gazebos with one attached to walk out porch over looking almost 3 acres of beautiful land. Attached 2 car garage and detached 2 car garage. Barn/workshop included, along with another metal building for storage.

  

  Philip 'PJ' Elder

  Omega Real Estate Brokerage LLC

  (859) 209-6934

  110 White Conkwright Rd, Winchester, KY 40391
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  /51

  $575,000

  • 3 Beds
  • 4 Baths
  • 3,160 Sq Ft

  520 Gay Evans Rd, Winchester, KY 40391

  Custom-built, 1-owner home nestled on 4.29 private acres minutes from Winchester & I-64. Located on a peaceful lane, this handsome ranch w/partially finished basement offers a bright & welcoming space that you will want to call home. The home boasts Hardie board-type siding/brick, Anderson windows, UPDATED 2025 shingles & a spacious front porch for relaxing. Inside, 9' & vaulted ceilings create

  

  Robin Jones

  Keller Williams Legacy Group

  (859) 577-7692

  520 Gay Evans Rd, Winchester, KY 40391
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  /57

  $512,000 Open Sun 2PM - 4PM

  • 4 Beds
  • 4 Baths
  • 4,448 Sq Ft

  150 Stone Crest Rd, Winchester, KY 40391

  WELCOME HOME >>>Room to spread out in this SPACIOUS Home of over 4000 sq. ft. sitting on 5.5 Acres! Offering 4 Bedrooms, 4 Bathrooms, Living Room, Beautiful Kitchen with appliances and tons of cherry cabinets, Den, utility room and 2 Large Bonus Rooms in the Basement. one could be a bedroom. There is a 3-car Detached Garage, 2-car attached Garage, Large Carport, Huge Patio around the Inground

  

  Brenda Murphy

  Murphy Realty Group

  (859) 470-3329

  150 Stone Crest Rd, Winchester, KY 40391
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  /10

  $135,000

  • Land
  • 4.01 Acres
  • $33,666 per Acre

  1940 Athens Boonesboro Rd, Winchester, KY 40391

  Escape to tranquility with this beautiful 4-acre lot in Clark County, offering the perfect setting to build your dream home. Tucked away on a quiet road, this property is surrounded by expansive farmland, ensuring ultimate privacy and peaceful living. A serene pond adds to the charm, providing a perfect spot to relax and enjoy the natural beauty of the land.This lot sits directly across

  

  Laura Sizemore

  Commonwealth Real Estate Professionals

  (859) 374-8725

  1940 Athens Boonesboro Rd, Winchester, KY 40391
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  /54

  $540,000

  • 3 Beds
  • 2.5 Baths
  • 2,020 Sq Ft

  1778 Elkin Rd, Winchester, KY 40391

  Peaceful Living on 8.83 aces of gently rolling hills in the heart of Kentucky. Breathtaking countryside features a charming home that offers peace, privacy and serene surroundings. Whether you're dreaming of a small hobby farm, a quiet artist retreat or just want space to breathe. This is the place. Wake up to birdsong, watch deer wander at dusk and soak in the golden sunsets from your own

  Valeria Kaidanov Pacesetters Real Estate

  1778 Elkin Rd, Winchester, KY 40391
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  /43

  $849,000

  • 5 Beds
  • 3.5 Baths
  • 3,384 Sq Ft

  150 Jones Nursery Rd, Winchester, KY 40391

  Experience the perfect blend of modern comfort and country charm in this stunning 4-bedroom, 3.5-bathroom Craftsman-style home, built in 2018. Nestled on 2.58 acres of scenic countryside, this property offers the serenity of rural living with convenient access to Lexington.Designed for both style and functionality, the spacious interior features a chef's kitchen with custom countertops, a

  Joshua Davis The Agency

  150 Jones Nursery Rd, Winchester, KY 40391
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  /38

  $769,000

  • 6 Beds
  • 4.5 Baths
  • 4,021 Sq Ft

  4455 Colby Rd, Winchester, KY 40391

  Experience country living in this stunning home on 3.56 acres located in a highly desirable area. Minutes from town and a short 15 minute drive to Hamburg. Enjoy beautiful views of the country from the covered front and back porches, perfect for morning coffee or evening gatherings. Open concept living. Spacious bedrooms. Partially finished basement. Beautiful sunroom. Updates throughout. Call

  Brian England Keller Williams Bluegrass Realty

  4455 Colby Rd, Winchester, KY 40391
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  /74

  $725,000

  • 3 Beds
  • 4 Baths
  • 4,123 Sq Ft

  1775 Irvine Rd, Winchester, KY 40391

  Own the most charming home atop a scenic hill at Blue Ridge Manor—a breathtaking 5.13-acre retreat where modern comfort meets classic elegance. As you drive up the long, private driveway, you'll feel like you're entering your own exclusive retreat, a sanctuary of peace and tranquility. Lovingly maintained by its original owner for the past 30 years, this beautifully renovated brick home (updated

  Oxana Lopetegui-Pineda Lifstyl Real Estate

  1775 Irvine Rd, Winchester, KY 40391
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  /79

  $849,900

  • 5 Beds
  • 3.5 Baths
  • 3,818 Sq Ft

  3714 Wades Mill Rd, Winchester, KY 40391

  Experience country living at FINEST in this immaculate 5-bedroom, 3.5-bath home on 11 acres, complete with two ponds and black plank fencing. The property includes an 864 SF horse barn with (2) 12x12 stalls, a tack area, and loft, along with a 1200 SF insulated equipment building. Inside, the 3800 SF home features soaring ceilings, large windows for panoramic views, and a great

  Nora Williams Keller Williams Commonwealth

  3714 Wades Mill Rd, Winchester, KY 40391
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  /67

  $1,185,000 Open Sun 2PM - 4PM

  • 5 Beds
  • 4 Baths
  • 4,058 Sq Ft

  2447 Clintonville Rd, Winchester, KY 40391

  What a great opportunity to own 3 acres just 15 minutes from Man O War and 20 minutes to the Hamburg Shopping Area. The property features a beautiful brick home built by Michael Childers to use as his main residence. It has been beautifully updated with gleaming, newly refinished hardwood floors, tall ceilings and lavish woodwork. The two story Entry is flanked by a formal Dining Room with a

  Suzanne Elliott Berkshire Hathaway de Movellan Properties

  2447 Clintonville Rd, Winchester, KY 40391
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  /58

  $565,000 Open Sat 10AM - 12PM

  • 4 Beds
  • 3.5 Baths
  • 3,958 Sq Ft

  1063 Wades Mill Rd, Winchester, KY 40391

  A fully remodeled 5-acre property offers a beautifully updated 3,958 sq ft home with 4 bedrooms, 3 full baths, and 1 half bath. Every inch of this spacious home has been thoughtfully updated, including brand-new flooring throughout and a newly installed HVAC unit upstairs for optimal comfort. The custom-designed primary closet provides a luxurious storage solution, while the energy-efficient

  Joseph Smallwood Christies International Real Estate Bluegrass

  1063 Wades Mill Rd, Winchester, KY 40391
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  /2

  $240,000

  • Land
  • 12 Acres
  • $19,835 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 lotsR-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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  /17

  $35,000

  • Land
  • 1.72 Acres
  • $20,349 per Acre

  12591 Ironworks Rd, Winchester, KY 40391

  This 1.722-acre lot presents a fantastic opportunity to design your ideal home in the subdivision of Eskippakithiki Overlooks. Enjoy the lovely views and ample space to unwind and relax. Located just minutes from Bert T. Combs Mountain Parkway, this property offers both convenience and tranquility. Utilities are readily available at the road, allowing you to start planning your new home right

  Cathleen Gedeon CENTURY 21 Advantage Realty

  12591 Ironworks Rd, Winchester, KY 40391
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  /19

  $40,000

  • Land
  • 2.34 Acres
  • $17,094 per Acre

  12651 Ironworks Rd, Winchester, KY 40391

  This 2.336-acre lot presents a fantastic opportunity to design your ideal home in the subdivision of Eskippakithiki Overlooks. Enjoy the lovely views and ample space to unwind and relax. Located just minutes from Bert T. Combs Mountain Parkway, this property offers both convenience and tranquility. Utilities are readily available at the road, allowing you to start planning your new home right

  Cathleen Gedeon CENTURY 21 Advantage Realty

  12651 Ironworks Rd, Winchester, KY 40391
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  /42

  $450,000

  • 3 Beds
  • 2 Baths
  • 2,120 Sq Ft

  485 Mccullough Ln, Winchester, KY 40391

  The Homestead you have been looking for. Farmhouse in the country. This beauty is just 6 miles from the interstate. Spacious 5.72 acres on this mini farm. It is located at the end of McCullough Lane. This three bedroom 2 bath home has 2,120 square feet. There is a beautiful 9 feet deep inground pool. The pool had a new liner and equipment installed 3 years ago. Inside you will find 3 fireplaces

  Dale Hatton Dream Maker Realty, LLC

  485 Mccullough Ln, Winchester, KY 40391
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  /24

  $224,000

  • 3 Beds
  • 1 Bath
  • 1,420 Sq Ft

  13365 Ironworks Rd, Winchester, KY 40391

  Charming and fully renovated, this 3-bedroom, 1-bathroom home offers the perfect blend of modern style and cozy comfort. With a fresh white exterior accented in black and a brand-new metal roof, it stands out with timeless curb appeal and lasting durability.Inside, every detail has been thoughtfully updated, from the sleek modern kitchen to the stylish lighting fixtures that brighten the

  Joshua Davis The Agency

  13365 Ironworks Rd, Winchester, KY 40391
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  /23

  $150,000

  • Land
  • 5.00 Acres
  • $30,000 per Acre

  2100 Old Log Lick Rd, Winchester, KY 40391

  Dreaming of peaceful country living with a head start on the building process? This beautiful 5-acre tract in the country has everything you need to get started: electric and water already in place, a septic system installed, and a cleared, flat spot just waiting for your dream home. The property features a pond, a gravel driveway, and a small shop with a bathroom and attached carport, perfect

  Michelle Blackburn RE/MAX Creative, Winchester

  2100 Old Log Lick Rd, Winchester, KY 40391
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  /2

  $150,000

  • Land
  • 2.77 Acres
  • $54,152 per Acre

  3385 Colby Rd, Winchester, KY 40391

  Small acreage lot on Colby Road! Accessed by easement from neighbors driveway.

  Steve Adams Steven D Adams Real Est Serv

  3385 Colby Rd, Winchester, KY 40391
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  /10

  $1,500,000

  • Land
  • 74 Acres
  • $20,322 per Acre

  3505 Basin Springs Rd, Winchester, KY 40391

  Located in the heart of Clark County this 73+/- acre property has been a part of the family since the 1800s. With its expansive space and fertile land, it offers endless possibilities for agricultural ventures, recreational use or development. Whether you're looking to expand your farming operation or create a private estate, this rare property presents a fantastic opportunity to invest in land

  Kathryn Cheuvront Coldwell Banker McMahan

  3505 Basin Springs Rd, Winchester, KY 40391
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  /5

  $110,000

  • Land
  • 2.06 Acres
  • $53,398 per Acre

  1185 Craig Crossing Rd, Winchester, KY 40391

  Lot # 30 contains 2.058 acres of gently rolling land perfect for your new home. This is a rare opportunity to own a piece of western Clark County real estate in the sought-after McClure Road area. Thoroughbred Estates is Winchester's newest upscale development containing 33 lots from 2 acres to nearly 7 acres. Lots are located just minutes from Winchester and Lexington.

  Keith Wilson Coldwell Banker McMahan

  1185 Craig Crossing Rd, Winchester, KY 40391
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  /6

  $180,000

  • Land
  • 4.45 Acres
  • $40,449 per Acre

  1030 Craig Crossing Rd, Winchester, KY 40391

  Lot # 14 contains 4.450 acres of gently rolling land with small stream perfect for your new home. This is a rare opportunity to own a piece of western Clark County real estate in the sought-after McClure Road area. Thoroughbred Estates is Winchester's newest upscale development containing 33 lots from 2 acres to nearly 7 acres. Lots are located just minutes from Winchester and Lexington.

  Keith Wilson Coldwell Banker McMahan

  1030 Craig Crossing Rd, Winchester, KY 40391
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  /7

  $195,000

  • Land
  • 6 Acres
  • $31,707 per Acre

  990 Craig Crossing Rd, Winchester, KY 40391

  Lot # 13 contains 6.153 acres of gently rolling land perfect for your new home. This is a rare opportunity to own a piece of western Clark County real estate in the sought-after McClure Road area. Thoroughbred Estates is Winchester's newest upscale development containing 33 lots from 2 acres to nearly 7 acres. Lots are located just minutes from Winchester and Lexington.

  Keith Wilson Coldwell Banker McMahan

  990 Craig Crossing Rd, Winchester, KY 40391
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  /29

  $339,500

  • 3 Beds
  • 2 Baths
  • 1,719 Sq Ft

  374 N Middletown Rd, Winchester, KY 40391

  More photos to come!!! Investment Opportunity! This is the Parent Listing. 2 Parcels listed for $339,500 (MLS listing #s 25005575 and 25005577). 2 Manufactured double-wide homes on permanent foundations sitting on ten acres in Clark County KY. Both properties, 374 and 360 N. Middletown Rd., are being offered together. (Child listing is 360 N. Middletown Rd). Mature garden and LOTS of

  Danielle Haggard Keller Williams Commonwealth

  374 N Middletown Rd, Winchester, KY 40391
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  /5

  $175,000

  • Land
  • 2.40 Acres
  • $72,917 per Acre

  3235 Colby Rd, Winchester, KY 40391

  Parcel 7 has rolling topography well suited for a walk-out basement overlooking the neighboring 175 acre farm. 1.5 miles from the Bypass, recently fenced, with water, natural gas, and electricity at the road.

  Steve Adams Steven D Adams Real Est Serv

  3235 Colby Rd, Winchester, KY 40391
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  /37

  $1,490,000

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

  700 Nick Ln, Winchester, KY 40391

  Step into country living with this amazing 120-acre working farm! You'll love the brand-new 3-bedroom, 2.5-bath home that features an open floor plan, perfect for hanging out with family or hosting friends. It's got all the modern touches, so you can enjoy both style and comfort.This farm is ready to work with a brand-new 2,000 sqft metal pole barn—plenty of space for storage, projects,

  Darrell Tackett Dream Maker Realty, LLC

  700 Nick Ln, Winchester, KY 40391
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  /2

  $115,000

  • Land
  • 1.03 Acres
  • $111,650 per Acre

  210 Hood Ave, Winchester, KY 40391

  This is an unique opportunity to own a beautiful acre + building lot in Winchester! Walking distance to downtown, Country Club, College Park & library! The house seat has been graded to accommodate a daylight walk-out basement. City water, sewer, natural gas & electric are available. Currently being resurveyed to include closed alleyway. Minimal restrictions. Owner/agent.

  Angie Conley Dixon Dixon Properties

  210 Hood Ave, Winchester, KY 40391
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  /4

  $70,000

  • Land
  • 1.92 Acres
  • $36,458 per Acre

  12569 Ironworks Rd, Winchester, KY 40391

  Build your dream home in the stunning ESKIPPAKITHIKI OVERLOOKS! This lot containing 1.919 acres, offer 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 the beauty and tranquility. Don't miss your opportunity to own prime land with unmatched potential!

  Kathryn Cheuvront Coldwell Banker McMahan

  12569 Ironworks Rd, Winchester, KY 40391
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  /3

  $70,000

  • Land
  • 2.04 Acres
  • $34,314 per Acre

  150 Spencer Ln, Winchester, KY 40391

  Build your dream home in the stunning ESKIPPAKITHIKI OVERLOOKS! This lot totaling 2.041 acres, offer 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 the beauty and tranquility. Don't miss your opportunity to own prime land with unmatched potential!

  Kathryn Cheuvront Coldwell Banker McMahan

  150 Spencer Ln, Winchester, KY 40391
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  /15

  $189,000

  • Land
  • 7 Acres
  • $25,403 per Acre

  7575 Irvine Rd, Winchester, KY 40391

  Amazing 7.44 acre country building lot / mini farm / homestead with views! Established driveway leads a nice 38' x 50' pole barn that would serve as a nice shop / garage! Partially fenced with gated entrance. Perfect spot to potentially build a pond. Water meter base and electricity pole already in place.

  Jason Townsend Kentucky Residential Real Estate, LLC

  7575 Irvine Rd, Winchester, KY 40391
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  /13

  $149,400

  • Land
  • 2.30 Acres
  • $64,957 per Acre

  110 Knox Ct, Winchester, KY 40391

  The largest and most desirable lot in The Reserve is now available! Nestled in a cul-de-sac, this 2.3 acre tract offers exceptional views of Bluegrass farmland. Build your custom dream home and watch the sun set over the pond, right from your porch. Located in one of Winchester's newest luxury subdivisions, featuring carefully crafted guidelines to preserve the community's character. All of this

  Jarran Thomas The Agency

  110 Knox Ct, Winchester, KY 40391
• 

  

  /22

  $105,000

  • Land
  • 3.49 Acres
  • $30,086 per Acre

  9776 Ironworks Rd, Winchester, KY 40391

  Beautiful piece of land to build your dream Barndominium, house, tiny house, manufactured home, workshop, whatever meets county regulations. No deed restrictions! 40' x 60' x 16' pole barn style garage / home already started for you! An older barn with stalls for the animals! Barn needs a little love. Approximately 515 feet of road frontage. Current access to property is a small easement from the

  Jason Townsend Kentucky Residential Real Estate, LLC

  9776 Ironworks Rd, Winchester, KY 40391
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  /4

  $109,000

  • Land
  • 4.02 Acres
  • $27,114 per Acre

  2058 Athens Boonesboro Rd, Winchester, KY 40391

  Prime building lot - 4.15 acres ready for your new dream home! Come pick your dream lot and enjoy the great views of the countryside and farmland. Rural living with the convenience of being just 15-20 minutes away from Lexington, Winchester and the interstate (I-75). 2058 and 2010 lots approved shared entrance. Multiple lots to choose from ranging from 4-8 acres +/-. Call today to get the first

  Megan McCoy Keller Williams Legacy Group

  2058 Athens Boonesboro Rd, Winchester, KY 40391
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  /3

  $109,000

  • Land
  • 4.02 Acres
  • $27,114 per Acre

  2010 Athens Boonesboro Rd, Winchester, KY 40391

  Prime building lot - 4 acres ready for your new dream home! Come pick your dream lot and enjoy the great views of the countryside and farmland. Rural living with the convenience of being just 15-20 minutes away from Lexington, Winchester and the interstate (I-75). 2010 and 2058 approved shared entrance. Multiple lots to choose from ranging from 4-8 acres +/-. Call today to get the first choice on

  Megan McCoy Keller Williams Legacy Group

  2010 Athens Boonesboro Rd, Winchester, KY 40391
• 

  

  /13

  $99,500

  • 2 Beds
  • 1 Bath
  • 1,113 Sq Ft

  2431 Pine Ridge Rd, Winchester, KY 40391

  Looking for a quite place in the country that will give you enough room for a great garden, a few chickens and a huge helping of peace and quiet?? This little gem may be for you. A 1920 built wood home tucked away in the hills of Clark County. Call today for your private showing.

  A. Rebecca Woods Woods Realty Group

  2431 Pine Ridge Rd, Winchester, KY 40391
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  /15

  $59,000

  • Land
  • 6 Acres
  • $10,555 per Acre

  199 Midway Rd, Winchester, KY 40391

  Introducing this 5.59 acre property in Central Kentucky! With city water and electric available at the road, this land offers a seamless transition for your dream home or investment project. Located just 15 minutes from Winchester, 30 minutes from Hamburg, and 30 minutes from Mt. Sterling. You will enjoy easy access to city amenities while relishing the peace of rural living. Don't miss the

  Skyler Lewis Dream Maker Realty, LLC

  199 Midway Rd, Winchester, KY 40391
• 

  

  /4

  $139,900

  • Land
  • 6 Acres
  • $24,674 per Acre

  1445 Gay Evans Rd, Winchester, KY 40391

  Welcome to The Retreat at Juett Farms! Come build your dream home on some of the best land that Clark County has to offer. This peaceful setting with unparalleled views of the countryside, is sure to impress. Imagine sitting on your front porch taking in the most amazing sunsets! This beautiful parcel has over 5 acres of unrestricted land. Schedule your showing today!

  Holly Goeing The Agency

  1445 Gay Evans Rd, Winchester, KY 40391
• 

  

  /4

  $149,900

  • Land
  • 6 Acres
  • $26,768 per Acre

  1541 Gay Evans Rd, Winchester, KY 40391

  Welcome to The Retreat at Juett Farms! Come build your dream home on some of the best land that Clark County has to offer. This peaceful setting with unparalleled views of the countryside, is sure to impress. Imagine sitting on your front porch taking in the most amazing sunsets! This beautiful parcel has over 5 acres of unrestricted land. Schedule your showing today!

  Holly Goeing The Agency

  1541 Gay Evans Rd, Winchester, KY 40391
• 

  

  /28

  $799,900

  • Land
  • 13 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 road 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

  Josh Wood Freedom Realty & Property Mgt

  1600 Ironworks Rd, Winchester, KY 40391
• 

  

  /22

  $949,900

  • Land
  • 12 Acres
  • $76,729 per Acre

  1203 Irvine Rd, Winchester, KY 40391

  This 12+ acre piece of prime real estate is full of potential! Zoned for business uses, the location is conveniently located with easy access to Veterans Memorial Bypass, I-64, and downtown Winchester. Utilities are already available at this property and there is a small structure included in as-is condition. Give us a call with any further questions.

  Josh Wood Freedom Realty & Property Mgt

  1203 Irvine Rd, Winchester, KY 40391
• 

  

  /4

  $140,000

  • Land
  • 3.94 Acres
  • $35,533 per Acre

  12569 Ironworks Rd, Winchester, KY 40391

  Build your dream home in the stunning ESKIPPAKITHIKI OVERLOOKS! These two parcels totaling 3.94 acres, offer 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 the beauty and tranquility. Don't miss your opportunity to own prime land with unmatched potential!

  Kathryn Cheuvront Coldwell Banker McMahan

  12569 Ironworks Rd, Winchester, KY 40391

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