Homes for Sale near George Rogers Clark High School

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  /77

  $2,150,000

  • Land
  • 71 Acres
  • $30,277 per Acre

  27 Sundown Ln, Winchester, KY 40391

  Tucked just 10 minutes from Hamburg on the Fayette/Clark County line, this 71+acre estate on Sundown Lane truly lives up to its name—offering breathtaking sunset views, along with peaceful luxury in a scenic country setting. At the end of a gated driveway, a stately colonial-style home combines refined living with countryside charm. Highlights include hardwood floors, two stone fireplaces, dual

  Abby Jones Bluegrass Sotheby's International Realty

  27 Sundown Ln, Winchester, KY 40391
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  /40

  $269,900

  • 5 Beds
  • 3 Baths
  • 2,617 Sq Ft

  400 Verna Dr, Winchester, KY 40391

  Spacious Brick Ranch with Dual Master Suites & Investor Potential! This charming 5-bedroom, 3-bath brick ranch is nestled in a well-established neighborhood and offers a rare opportunity for customization and value-add. With some renovation projects already started, this home is ideal for an investor or handy homeowner ready to build instant equity.Enjoy the flexibility of two master suites,

  Melodie Lincavage RE/MAX Elite Realty

  400 Verna Dr, Winchester, KY 40391
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  /3

  $230,000

  • 3 Beds
  • 2.5 Baths
  • 1,300 Sq Ft

  412 Paisley Ct, Winchester, KY 40391

  Very nice 3 bedroom 2.1 bath townhome with walk out basement. Home was upgraded 2023 with new paint,carpet, granite countertops and stainless appliances. Only minutes from Winchester bypass.

  John Wilson Bluegrass Properties Group

  412 Paisley Ct, Winchester, KY 40391
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  /3

  $345,000

  • 3 Beds
  • 2 Baths
  • 1,677 Sq Ft

  225 Evergreen Dr, Winchester, KY 40391

  Welcome to The Run for the Roses - a thoughtfully designed proposed construction home located in the desirable Locust Hill Acres community. This charming home offers an open concept floor plan perfect for modern living, featuring 3 spacious bedrooms and 2 full bathrooms.The large primary suite is a true retreat, complete with a generously sized walk-in closet and a well-appointed ensuite

  Rex Hall United Real Estate Bluegrass

  225 Evergreen Dr, Winchester, KY 40391
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  /2

  $345,000

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  215 Evergreen Dr, Winchester, KY 40391

  Welcome to Triple Crown - a stunning proposed construction home nestled in the beautiful Locust Hill Acres community. Thoughtfully designed with an open-concept layout, this home offers 3 comfortable bedrooms, 2 full bathrooms, and versatile living spaces perfect for today's lifestyle.The expansive primary suite serves as a private sanctuary, complete with a spacious walk-in closet and a

  Rex Hall United Real Estate Bluegrass

  215 Evergreen Dr, Winchester, KY 40391
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  /24

  $295,000

  • 3 Beds
  • 2 Baths
  • 1,306 Sq Ft

  110 Albany Ln, Winchester, KY 40391

  Lovely one level brick ranch on a corner lot conveniently located in the Meadows just off of McClure Rd. 3 bedroom, 2 full bath with a beautiful yard and a storage building out back.

  Jason Townsend Kentucky Residential Real Estate, LLC

  110 Albany Ln, Winchester, KY 40391
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  /43

  $290,000

  • 4 Beds
  • 2 Baths
  • 1,475 Sq Ft

  2832 Two Mile Rd, Winchester, KY 40391

  Brand new 4 Bedroom 2 bath home on an acre lot. Home features Master Bedroom suite, separate utility room, new front and back decks to enjoy your peace and quiet. Other features are new fencing and new septic tank. Move-in ready. Close to shopping and restaurants, less than 4 miles. 13 miles to I-75 and 6 miles to I-64. Within 30 minutes to Richmond and Hamburg area of Lexington.

  Robin Horn Keller Williams Commonwealth

  2832 Two Mile Rd, Winchester, KY 40391
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  /63

  $1,950,000

  • Land
  • 55 Acres
  • $35,455 per Acre

  345 Boone Ridge Ln, Winchester, KY 40515

  20 minutes from Lexington in the Iroquois Hunt Country you will find this sanctuary...its not about stellar fencing, a gated entrance or a mcmansion. Its ALL about the one half mile of frontage on the most beautiful stream in the Bluegrass, Boone Creek! This rare and easily accessible frontage is opposed on the other side with rock faced palisades and the most spectacular setting imaginable.

  Linda Willson Homes&Horse Farms Real Estate

  345 Boone Ridge Ln, Winchester, KY 40515
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  /5

  $45,000

  • Land
  • 0.36 Acre
  • $125,000 per Acre

  434 Fairholme Way, Winchester, KY 40391

  Ready to build your forever home? Look no further! This lot is conveniently located in the highly sought after Fairholme Estates, which is a short golf cart ride to the Winchester Country Club and downtown Winchester.

  Justin Lee JL Realty Group, LLC

  434 Fairholme Way, Winchester, KY 40391
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  /60

  $334,900

  • 4 Beds
  • 2.5 Baths
  • 2,136 Sq Ft

  402 Mcdowell Dr, Winchester, KY 40391

  Very clean, well kept home! Split foyer with plenty of space including a large kitchen with peninsula and open to dining area. Four bedrooms, 2.5 baths. Nice size living room on main level with additional family room with wood burning fireplace featuring full brick wall on lower level.Very large 2 car garage. Beautiful back covered deck that leads to a lovely gazebo in the spacious fenced in

  Christine McDonald FC Tucker Bluegrass

  402 Mcdowell Dr, Winchester, KY 40391
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  /5

  $105,000

  • Land
  • 1.00 Acre
  • $105,000 per Acre

  1730 Mcclure Rd, Winchester, KY 40391

  Awesome property, just waiting for you to build your perfect home, ready to fulfill your dreams, great area close to everything.Seller will run the water line to the propertyLots One and Two have entrances beside each other, shown on plat

  Mila Ensor Ensor Real Estate LLC

  1730 Mcclure Rd, Winchester, KY 40391
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  /4

  $95,000

  • Land
  • 1.09 Acres
  • $87,156 per Acre

  1700 Mcclure Rd, Winchester, KY 40391

  Awesome property, just waiting for you to build your perfect home, ready to fulfill your dreams, great area close to everything.Seller will run the water line to the propertyLots One and Two have entrances beside each other, shown on plat

  Mila Ensor Ensor Real Estate LLC

  1700 Mcclure Rd, Winchester, KY 40391
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  /3

  $135,000

  • Land
  • 10 Acres
  • $13,145 per Acre

  4150 Schollsville Rd, Winchester, KY 40391

  This land located in the center of hunting paradise, where nature excels her beauty, a place for you to build your perfect home,10.27acres, call todayCity water is East Clark Water and it is across road, as per the seller back of property has a fence that is not true to the property lineThe gate next to this acreage is not on this property, look for the orange markers on the front fence

  Mila Ensor Ensor Real Estate LLC

  4150 Schollsville Rd, Winchester, KY 40391
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  /72

  $990,000

  • 4 Beds
  • 3.5 Baths
  • 4,221 Sq Ft

  1701 Gay Evans Rd, Winchester, KY 40391

  Escape to your own private retreat with this beautiful brick ranch set on 8 plus acres. This home boasts a bright and airy sunroom, perfect for enjoying morning coffee watching the sunrise or unwinding with the nature views. The fully finished basement offers extra living space, while the in-ground pool is ready for summer fun. This property offers a two-car attached garage as well as a

  Kathryn Cheuvront Coldwell Banker McMahan

  1701 Gay Evans Rd, Winchester, KY 40391
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  /19

  $175,000

  • 4 Beds
  • 1 Bath
  • 1,120 Sq Ft

  8 1/2 1st St, Winchester, KY 40391

  In the heart of downtown Winchester, don't miss out on this adorable home! Newly remodeled and move in ready! New appliances, new HVAC, new windows, and so much more! Kitchen has granite countertops too! Open floor plan that is great for entertaining! Schedule your showing today!

  Michelle Ann Tellman Lifstyl Real Estate

  8 1/2 1st St, Winchester, KY 40391
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  /50

  $279,500

  • 3 Beds
  • 2 Baths
  • 1,928 Sq Ft

  113 Olde Potomac Ave, Winchester, KY 40391

  This phenomenal property has had so many updates including the addition of a full bath on the second floor, an updated electric panel, including new wiring throughout the entire home and added electrical outlets, all new plumbing throughout the home, a heat pump for the second floor (there is gas heat on the first floor) and a walk-in closet for the master bedroom on the first floor. The owners

  Susan Colwell Colwell Realty Professionals

  113 Olde Potomac Ave, Winchester, KY 40391
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  /8

  $159,000

  • 2 Beds
  • 3 Baths
  • 1,056 Sq Ft

  125 Chatham Place, Winchester, KY 40391

  Why rent when you can own this Townhome it has 2 bedrooms,3 bathroms (one full bath and 2 half baths) living room,kitchen, locted near schools and shopping,just behind Lowes.Owner/Broker

  Garry Milton Milton and Associates Real Estate

  125 Chatham Place, Winchester, KY 40391
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  /7

  $825,000

  • Land
  • 4.87 Acres
  • $169,405 per Acre

  1108 W Lexington Ave, Winchester, KY 40391

  Rare opportunity to purchase a large multi-family development in the heart of Winchester! Directly across the street from Legacy Grove Park! All building and engineering plans included to build 66 approved townhomes with the possibility of adding 4 more. Currently zoned PD (Planned Development), could possibly be changed to commercial due to neighboring commercial property. Main property is 4.87

  Jason Townsend Kentucky Residential Real Estate, LLC

  1108 W Lexington Ave, Winchester, KY 40391
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  /50

  $989,000

  • 4 Beds
  • 2.5 Baths
  • 2,670 Sq Ft

  1110 Craig Crossing, Winchester, KY 40391

  Discover timeless elegance and modern luxury in this newly constructed residence, perfectly situated on over 2.5 acres in Winchester. With 2,670 sq ft of custom designed living space, this 4-bedroom, 2.5-bath home offers craftsmanship, high-end finishes, and exceptional outdoor living. White oak engineered hardwood flooring, moulding throughout, and exquisite details. The spacious great room

  Michael Hilario The Agency

  1110 Craig Crossing, Winchester, KY 40391
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  /69

  $995,000

  • 5 Beds
  • 3.5 Baths
  • 2,842 Sq Ft

  1150 Craig Crossing, Winchester, KY 40391

  Stunning new construction featuring 5 bedroom. 3.5 bath nestled on roughly 2.5 serene acres, surrounded by picturesque farmland and panoramic views. Offering the perfect blend of space, style, and serenity. Features include open concept layout, spacious kitchen with kitchen island, granite counter tops, hidden walk in pantry with custom cabinets and well appointed appliances. Hardwood floors and

  Stephanie Hacker Kentucky Residential Real Estate, LLC

  1150 Craig Crossing, Winchester, KY 40391
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  /54

  $530,000

  • 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

  Vicki VanWinkle Pacesetters Real Estate

  1778 Elkin Rd, Winchester, KY 40391
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  /9

  $210,000

  • Land
  • 8 Acres
  • $27,027 per Acre

  Unlisted Address

  Build your dream home on this gorgeous 7.77-acre lot on Flannagan Station Road in Winchester. Offering a quiet, country setting with gently rolling land, this property is ideal for a custom home, hobby farm, or simply extra space to enjoy. Plenty of room for a house, garden, or recreational use, with beautiful views all around. Located just minutes from the Winchester Bypass for an easy commute

  Shari Frasure Keller Williams Commonwealth

  Unlisted Address
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  /73

  $825,000

  • 5 Beds
  • 3 Baths
  • 3,664 Sq Ft

  1183 the Ridings Rd, Winchester, KY 40391

  This beautiful 5 bedroom 3 full bath home sits on 5 acres in The Ridings at Colby. This neighborhood has horseback riding trails throughout & is a 15 minute drive to the Hamburg/Lexington area. Large eat in kitchen with island, granite countertops & stainless steel appliances. Entertain in your custom dining room featuring a tray ceiling & wainscoting, or on your covered outdoor Trex deck. Relax

  Libby VanMeter Marshall Lane Real Estate - Lexington

  1183 the Ridings Rd, Winchester, KY 40391
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  /36

  $829,900

  • 2 Beds
  • 3 Baths
  • 12,900 Sq Ft

  8129 Wades Mill Rd, Winchester, KY 40391

  This is what BARDOMINIUM Dreams are made of!!!! Welcome to your barndo retreat — an expansive 92' x 120' steel-framed structure situated on 4.27 partially fenced acres with breathtaking pond views and unmatched amenities for both living and working.This massive structure boasts an open-concept interior layout with endless potential! Ideal for combining luxury living with functional workspace.

  Holly Goeing The Agency

  8129 Wades Mill Rd, Winchester, KY 40391
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  /33

  $184,900

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft

  307 Blair Ave, Winchester, KY 40391

  This charming 3-bedroom, 1-bath ranch offers fresh updates throughout, including brand new flooring and interior paint. The inviting side porch features a ramp for easy accessibility and leads to a spacious patio—perfect for relaxing or entertaining. A detached two-car garage adds great storage and functionality. Located just minutes from downtown Winchester and I-64, this move-in-ready home

  Brooke Otis-Mull RO&CO Real Estate

  307 Blair Ave, Winchester, KY 40391
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  /41

  $259,000

  • 3 Beds
  • 2 Baths
  • 2,142 Sq Ft

  363 S Main St, Winchester, KY 40391

  ** Seller is offering a $10,000 credit at close with an acceptable offer!**Welcome to 363 South Main Street in the heart of Winchester, Kentucky! This charming 3-bedroom, 2-bath home offers the perfect blend of timeless character and modern convenience. Built in 1940, the home exudes classic appeal with thoughtful updates that meet today's lifestyle. With 2,142 square feet of living space,

  Zachary Otis HomeLand Real Estate Inc

  363 S Main St, Winchester, KY 40391
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  /8

  $129,000

  • 2 Beds
  • 1 Bath
  • 637 Sq Ft

  109 Spring St, Winchester, KY 40391

  Investment opportunity in Winchester! This 2-bedroom, 1-bath home at 109 Spring St is currently tenant-occupied and leased at $900/month. Functional layout with a spacious kitchen and separate living area. Conveniently located near downtown, schools, and local amenities. Whether you're expanding your portfolio or looking for a starter investment, this property offers steady rental income from day

  Shari Frasure Keller Williams Commonwealth

  109 Spring St, Winchester, KY 40391
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  /49

  $635,000

  • 6 Beds
  • 3.5 Baths
  • 5,227 Sq Ft

  439 Lynnway Dr, Winchester, KY 40391

  Welcome to 439 Lynnway Drive, where a brand new roof was just installed April 2025. The main floor boasts a primary en-suite, office space, and laundry room, while the second floor offers additional bedrooms and a versatile bonus room. The basement offers private bed/bath, custom bar, home theater, and in-home gym. Step outside and prepare to be enchanted by an outdoor oasis. Outdoor kitchen

  Reagan Rainey Dream Maker Realty, LLC

  439 Lynnway Dr, Winchester, KY 40391
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  /5

  $29,000

  • Land
  • 0.46 Acre
  • $63,043 per Acre

  102 Augusta Dr, Winchester, KY 40391

  This is a beautiful area to build your dream home. Backs up to a golf course for a magnificent view. Just minutes from Fort Boonesborough National Park.

  Dale Hatton Dream Maker Realty, LLC

  102 Augusta Dr, Winchester, KY 40391
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  /34

  $235,000

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft

  37 7th St, Winchester, KY 40391

  Check out this charming, well-maintained single-story brick ranch! Featuring 3 bedrooms, 2 full bathrooms, and a spacious living room, this home offers comfort and convenience. Recent updates over the past 10 years include a new HVAC system, roof, windows, water heater, and appliances. The oversized 2-car garage provides ample indoor parking, with additional off-street parking for two more

  Andrew Fugitt Coldwell Banker McMahan

  37 7th St, Winchester, KY 40391
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  /62

  $275,950

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

  3614 Stamper Dr, Winchester, KY 40391

  'Fully renovated to perfection, this property features brand-new upgrades throughout. Highlights include newly installed windows, doors, and flooring, complemented by modern appliances and updated cabinetry. A new deck provides an ideal space for outdoor enjoyment, while contemporary fixtures add a touch of elegance. This home is truly a remarkable opportunity and an absolute must-see.'

  Darrell Tackett Dream Maker Realty, LLC

  3614 Stamper Dr, 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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  /3

  $40,000

  • Land
  • 0.19 Acre
  • $210,526 per Acre

  113 Mayfair Ct, Winchester, KY 40391

  Wowser! Looking for a lot that backs up to greenspace and will NOT have another home on one side? Here it IS! This may be just what you're looking for. Originally, the street was supposed to connect, but due to the changes in grade, this won't be happening! Plus, with the way the lot sits, you can enjoy many beautiful sunsets. It's a hidden gem just waiting for you to find it! The home to

  Jo Gawthrop Keller Williams Bluegrass Realty

  113 Mayfair Ct, Winchester, KY 40391
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  /2

  $40,000

  • Land
  • 0.26 Acre
  • $153,846 per Acre

  105 Bella Ct, Winchester, KY 40391

  Vacant Lot in a quiet cul-de-sac

  Jo Gawthrop Keller Williams Bluegrass Realty

  105 Bella Ct, Winchester, KY 40391
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  /2

  $42,500

  • Land
  • 0.20 Acre
  • $212,500 per Acre

  108 Dorset Ln, Winchester, KY 40391

  The restictions state that if it is a ranch plan, there is a minimun of 1300 sq ft. It it is a 1 1/2 story or two story then 1800 sq ft will be required. A two car garage must be attached. Developer will need to approve plans before starting construction This lot is ideal for a walkout basement. Perfect setting for watching the sunsets

  Jo Gawthrop Keller Williams Bluegrass Realty

  108 Dorset Ln, Winchester, KY 40391
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  /73

  $339,900

  • 3 Beds
  • 2 Baths
  • 1,805 Sq Ft

  407 Fairholme Way, Winchester, KY 40391

  Looking for a newer home in a beautiful, family friendly neighborhood? Look no further than this lovely, low maintenance home in the desirable Fairholme Estates subdivision. Take a step inside and enjoy the sunlight streaming in through the abundant windows in the great room. Gleaming, easy to clean, laminate wood plank flooring spills into the spacious kitchen area which features an oversized

  Josh Wood Freedom Realty & Property Mgt

  407 Fairholme Way, Winchester, KY 40391
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  /21

  $149,000

  • 2 Beds
  • 1 Bath
  • 886 Sq Ft

  9 Linden Ave, Winchester, KY 40391

  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, no warranties implied or expressed.Property conveys at

  Emily Hacker-Todd CENTURY 21 Advantage Realty

  9 Linden Ave, Winchester, KY 40391
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  /46

  $199,900

  • 3 Beds
  • 2 Baths
  • 1,167 Sq Ft

  115 Georgia St, Winchester, KY 40391

  ✨ ''Warm, inviting, and full of character—your dream home awaits!'' 🔥 ''Cozy up by the fireplace in a home that feels like home!'' 🏡 ''Classic charm meets modern convenience in this Winchester gem!'' 🌳 ''Tranquility meets accessibility—peaceful neighborhood, minutes from downtown!'' 🚗 ''Detached garage = extra storage, workspace, and convenience!'' 💎

  Darrell Tackett Dream Maker Realty, LLC

  115 Georgia St, Winchester, KY 40391
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  /23

  $140,000

  • Land
  • 5.00 Acres
  • $28,000 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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  /38

  $749,000

  • 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

Showing Results 41 - 80, Page 2 of 5