Winchester, KY Homes for Sale with Acreage

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  /18

  $574,000

  • 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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  /67

  $699,000

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

  1775 Irvine Rd, Winchester, KY 40391

  Just 12 minutes from Lexington, 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

  

  Oxana Lopetegui-Pineda

  Lifstyl Real Estate

  (859) 659-6462

  1775 Irvine Rd, Winchester, KY 40391
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  /58

  $488,000

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

  150 Stone Crest Rd, Winchester, KY 40391

  IMMEDIATE OCCUPANCY! WELCOME HOME with 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

  

  Brenda Murphy

  Murphy Realty Group

  (859) 374-8718

  150 Stone Crest Rd, Winchester, KY 40391
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  /117

  $3,175,000

  • 8 Beds
  • 7.5 Baths
  • 12,702 Sq Ft

  4664 Lexington Rd, Winchester, KY 40391

  Visitors to the farm are greeted by a substantial stone entry before traveling a gently winding path to the circular drive. There rests the grand residence, offering an ideal setting for entertaining family & friends. Ten minutes from Hamburg, the farm is located on the convenient Lexington/Winchester Road. Lovely views abound and the property retains remarkable privacy. The 13,500 square foot

  Zach Davis Kirkpatrick & Company

  4664 Lexington Rd, Winchester, KY 40391
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  /83

  $599,500

  • 3 Beds
  • 2 Baths
  • 2,222 Sq Ft

  2615 Crowe Ridge Rd, Winchester, KY 40391

  This one-owner, custom-built home sits on approximately 8 acres of beautiful Bluegrass land and offers space, comfort, and thoughtful design throughout. The open-concept great room and kitchen feature exposed beam ceilings and custom-stained concrete floors. The kitchen is a dream for cooks,with abundant counter space, storage, a large island, and window overlooking the backyard and pool. Just

  ROBIN TRIMBLE HomeFirst Real Estate

  2615 Crowe Ridge Rd, Winchester, KY 40391
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  /44

  $834,000

  • 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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  /52

  $555,000

  • 4 Beds
  • 2 Baths
  • 2,940 Sq Ft

  5515 Van Meter Rd, Winchester, KY 40391

  Welcome to your dream home, perfectly nestled in a highly desired location. This stunning property spans a generous 5 acres, offering an idyllic setting for homesteading. Experience the best of country living with the convenience of nearby amenities.The home boasts beautiful views that will take your breath away every morning. Imagine waking up to the serene beauty of nature, right at your

  Robyn Bradley Woods Realty Group

  5515 Van Meter Rd, Winchester, KY 40391
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  /72

  $960,000

  • 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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  /69

  $650,000 Open Sat 1PM - 3PM

  • 3 Beds
  • 3 Baths
  • 2,927 Sq Ft

  2085 Hancock Valley Dr, Winchester, KY 40391

  Spacious 3-Bedroom Home on Nearly 5 Acres in Winchester, KY!Discover country living at its finest with this beautiful 3-bedroom, 3-bathroom home set on nearly 5 acres of picturesque land. Featuring beautiful hardwood floors, a finished basement, and plenty of space for entertaining and friends, this property is designed for comfort and social gatherings. Enjoy the in-ground pool, pole barn, and

  Terry Billiter Premier Property Consultants

  2085 Hancock Valley Dr, Winchester, KY 40391
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  /64

  $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

  $975,000

  • 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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  /73

  $799,000

  • 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 & stainless steel appliances. Entertain in your custom dining room featuring a tray ceiling & wainscoting, or on your covered outdoor Trex deck. Relax in either your living

  Libby VanMeter Marshall Lane Real Estate - Lexington

  1183 the Ridings Rd, Winchester, KY 40391
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  /37

  $1,249,500

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

  700 Nick Ln, Winchester, KY 40391

  🚨 BIG PRICE DROP ALERT! 🚨 Motivated sellers are ready to make a deal—this is your chance to snag an unbeatable offer! 💰🏡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

  Darrell Tackett Dream Maker Realty, LLC

  700 Nick Ln, Winchester, KY 40391
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  /39

  $499,000

  • 3 Beds
  • 2.5 Baths
  • 2,076 Sq Ft

  600 Ferry Rd, Winchester, KY 40391

  Experience abundant wildlife with turkey and deer in your own hunting retreat, or simply enjoy the views from your backyard on this stunning 33-acre property. Conveniently located near the Kentucky River, with a boat ramp nearby, this home offers the perfect blend of nature and accessibility, making it ideal for nature lovers or those who enjoy fishing and hunting.Step inside to the foyer,

  Cathleen Gedeon CENTURY 21 Advantage Realty

  600 Ferry Rd, Winchester, KY 40391
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  /14

  $265,000

  • Land
  • 52 Acres
  • $5,048 per Acre

  3020 Dry Fork Creek Rd, Winchester, KY 40391

  Unmatched Opportunity - 52.5 Acres Just 30 Minutes from Lexington!Escape to your own private retreat with this expansive 52.5-acre property, ideally located just 30 minutes from Lexington and only 15 minutes from downtown Winchester. Whether you're dreaming of building your custom home surrounded by nature or creating the perfect hunting getaway, this property offers endless

  Danielle Hatton The Brokerage

  3020 Dry Fork Creek Rd, Winchester, KY 40391
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  /40

  $342,000

  • 3 Beds
  • 2 Baths
  • 1,988 Sq Ft

  13544 Irvine Rd, Winchester, KY 40391

  Ready for beautiful sunrises and bird watching? This home offers that and more! Almost 4 acres with a tree grove, surrounds this brick ranch on full basement. The possibility to finish the basement and downstairs bath, could add to your sq. ft. Room for a garden/chickens, if that is your thing. Come welcome the peacefulness of country living!

  Susan Baldwin Rector Hayden Realtors

  13544 Irvine Rd, Winchester, KY 40391
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  /3

  $380,000

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

  270 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 on unfinished walkout basement.The large primary suite is a true retreat, complete with a generously sized walk-in closet and a

  Rex Hall United Real Estate Bluegrass

  270 Evergreen Dr, Winchester, KY 40391
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  /3

  $430,000

  • 3 Beds
  • 2 Baths
  • 1,855 Sq Ft

  265 Evergreen Dr, Winchester, KY 40391

  Introducing The Mulberry floor plan - a beautifully designed proposed construction home in the scenic Locust Hill Acres community. This open-concept floor plan offers the perfect blend of comfort and functionality with 3 bedrooms, 2 full bathrooms, walkout unfinished basement and thoughtful living spaces throughout.The spacious primary suite features a large walk-in closet and a private ensuite

  Rex Hall United Real Estate Bluegrass

  265 Evergreen Dr, Winchester, KY 40391
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  /3

  $430,000

  • 3 Beds
  • 2 Baths
  • 1,885 Sq Ft

  250 Evergreen Dr, Winchester, KY 40391

  Introducing The Mulberry floor plan - a beautifully designed proposed construction home in the scenic Locust Hill Acres community. This open-concept floor plan offers the perfect blend of comfort and functionality with 3 bedrooms, 2 full bathrooms, unfinished walkout basement and thoughtful living spaces throughout.The spacious primary suite features a large walk-in closet and a private ensuite

  Rex Hall United Real Estate Bluegrass

  250 Evergreen Dr, Winchester, KY 40391
• 

  

  /3

  $380,000

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

  230 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

  230 Evergreen Dr, 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
• 

  

  /3

  $430,000

  • 3 Beds
  • 2 Baths
  • 1,935 Sq Ft

  220 Evergreen Dr, Winchester, KY 40391

  Introducing The Mulberry floor plan - a beautifully designed proposed construction home in the scenic Locust Hill Acres community. This open-concept floor plan offers the perfect blend of comfort and functionality with 3 bedrooms, 2 full bathrooms, unfinished walkout basement and thoughtful living spaces throughout.The spacious primary suite features a large walk-in closet and a private ensuite

  Rex Hall United Real Estate Bluegrass

  220 Evergreen Dr, Winchester, KY 40391
• 

  /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
• 

  

  /3

  $380,000

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

  200 Evergreen Dr, Winchester, KY 40391

  Introducing the Run For The Roses - 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 bathroom. The kitchen

  Rex Hall United Real Estate Bluegrass

  200 Evergreen Dr, Winchester, KY 40391
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  /103

  $2,995,000

  • 6 Beds
  • 5.5 Baths
  • 7,274 Sq Ft

  5045 Van Meter Rd, Winchester, KY 40391

  Welcome to a truly exceptional 10-acre estate, where luxury and nature converge. This custom-built, three-story home, completed in 2006 , offers 7274 sq ft of meticulously designed living space. With 6 bedrooms and 5.5 bathrooms, there's ample room for family and guests. The impressive 2432 sq ft, temperature-controlled 5-car garage provides extensive space for vehicles and hobbies. Beyond the

  The Prather Team - Michael Prather Keller Williams Bluegrass Realty

  5045 Van Meter Rd, Winchester, KY 40391
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  /92

  $1,200,000

  • 5 Beds
  • 7 Baths
  • 8,236 Sq Ft

  6237 Bybee Rd, Winchester, KY 40391

  Step into timeless elegance with this breathtaking modern Victorian-style masterpiece, perfectly positioned on 4.39 acres with panoramic views of sunrises, sunsets, and distant mountains. Designed and built by Tom Padgett, this home is rich in character and detail—from hand-hewn wood beam ceilings to Waterford crystal chandeliers. The grand 2-story foyer welcomes you into a flowing layout that

  Amanda Marcum Berkshire Hathaway HomeServices Foster Realtors

  6237 Bybee Rd, Winchester, KY 40391
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  /19

  $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 from the

  Laura Sizemore Kentucky Land and Home

  1940 Athens Boonesboro Rd, Winchester, KY 40391
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  /57

  $524,999

  • 8 Beds
  • 5 Baths
  • 3,845 Sq Ft

  1731 Ford Hampton Rd, Winchester, KY 40391

  Craftsman style home on 5 Acres with Horse Barn & Dual Living SpacesWelcome to your dream countryside escape. Nestled on five picturesque acres, this home combines timeless charm with versatility. It's perfect for those seeking space, privacy, and multi-generational living or rental potential.The main house offers 5 bedrooms and 3 full baths. Step inside the possible rental spaces to discover a

  Julie Wiggington RE/MAX Creative, Winchester

  1731 Ford Hampton Rd, Winchester, KY 40391
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  /32

  $210,000

  • 3 Beds
  • 2 Baths
  • 1,294 Sq Ft

  2858 Ford Hampton Rd, Winchester, KY 40391

  This cozy place has so much to offer. 3 spacious bedrooms and 2 full bathrooms. The kitchen has handmade cabinets throughout. The property includes a large 1,050 square foot detached garage and a 448 square foot building. It is located just minutes from the Boonesborough State Park and the scenic Kentucky River. Camping, hiking, fine dining, golf courses, and several other amenities are also

  Dale Hatton Dream Maker Realty, LLC

  2858 Ford Hampton Rd, Winchester, KY 40391
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  /30

  $250,000

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft

  2721 Pretty Run Rd, Winchester, KY 40391

  *48 Hour Kickout Clause in effect* Situated on 5 scenic acres along a highly sought-after country road, this 3-bedroom, 2-bath property presents an excellent opportunity to create your dream rural retreat. The home features a functional layout with a spacious living area, an eat-in kitchen, and a primary suite with its own bath. Two additional bedrooms offer flexibility for family, guests, or

  Michelle Blackburn RE/MAX Creative, Winchester

  2721 Pretty Run Rd, Winchester, KY 40391
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  /43

  $275,000

  • 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

  $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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  /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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  /52

  $530,000

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

  1778 Elkin Rd, Winchester, KY 40391

  Peaceful Living on 8.83 acres of gently rolling hills in the heart of Kentucky. Breathtaking countryside features a newer custom-built home that offers peace, privacy and serene surroundings. Wake up to birdsong, watch deer wander at dusk and soak in the golden sunsets from your own front porch. Highlights include: spacious open concept kitchen with white custom cabinetry, beautiful engineered

  Vicki VanWinkle Pacesetters Real Estate

  1778 Elkin Rd, Winchester, KY 40391
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  /9

  $206,000

  • Land
  • 8 Acres
  • $26,512 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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  /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
• 

  /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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