Winchester, KY Homes for Sale with Acreage

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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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  Explore Winchester

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  /40

  $239,900

  • 2 Beds
  • 2 Baths
  • 1,628 Sq Ft

  635 Lisletown Ln, Winchester, KY 40391

  Tucked away on a private lane behind a charming stone wall, this storybook 2BR/2BA dome-style cottage is a one-of-a-kind retreat. Greeted by a peaceful koi pond, the home's unique wood siding and architectural flair set the tone for something truly special. Inside, natural light pours in through skylights and stained-glass accents, creating a warm, ethereal atmosphere. The inviting living room

  

  Robin Jones

  Keller Williams Legacy Group

  (859) 328-1145

  635 Lisletown Ln, 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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  /120

  $559,900

  • 6 Beds
  • 3.5 Baths
  • 3,846 Sq Ft

  1953 Cabin Creek Rd, Winchester, KY 40391

  ***Click on the Virtual Tour section to see the video walk through!*** This unique property includes not only one, but two beautiful homes in the heart of Kentucky Bluegrass country. The first home is a brick ranch with a covered front porch and back patio that overlook this beautiful piece of farm land. This 2046 sq ft home contains 3 bedrooms and 2 full baths with a large great room in the

  Josh Wood Freedom Realty & Property Management

  1953 Cabin Creek Rd, Winchester, KY 40391
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  /80

  $574,900

  • 3 Beds
  • 2.5 Baths
  • 4,933 Sq Ft

  160 Agawam Rd, Winchester, KY 40391

  Welcome to this beautifully maintained brick ranch home set on a spacious and private 5-acre fenced lot. This versatile property offers the perfect blend of comfort, functionality, and rural charm - ideal for families, hobby farmers, or equestrian enthusiasts. Inside, you'll find 3 bedrooms and 3 bathrooms with a fully finished basement that offers ample space for additional bedrooms, a home gym,

  Megan McCoy Keller Williams Legacy Group

  160 Agawam Rd, 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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  /56

  $639,000

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

  4455 Colby Rd, Winchester, KY 40391

  Gorgeous Ranch Home On Basement, Situated Perfectly On Over 3.5 Lush Acres Of Level Seclusion, As Property Is Lined Beautiful, Mature Trees! Enjoy Peace & Quiet In This Newly Renovated Home, Offering 6 Bedrooms, 5 Baths, Ample Family Space, Home Office, (Fiber Optic Internet), Large Separate Laundry, Sun Room, 2 Covered Porches, Deck, Fire Pit, 2 Car Garage, Barn/ Workshop... THE LIST GOES ON!

  Melissa Thompson Keller Williams Legacy Group

  4455 Colby Rd, Winchester, KY 40391
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  /52

  $549,900

  • 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

  Robyn Bradley Woods Realty Group

  5515 Van Meter Rd, Winchester, KY 40391
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  /79

  $890,000

  • 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

  $639,900

  • 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,

  Terry Billiter Premier Property Consultants

  2085 Hancock Valley Dr, 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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  /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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  /70

  $949,000

  • 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 move in ready property features a beautiful brick home built by builder, Michael Childers, to use as his main residence. The property also has a 3 car detached Garage which is deep enough to hold 6 cars and one door is tall for storage of a Recreational Vehicle. It has been

  Suzanne Elliott Berkshire Hathaway de Movellan Properties

  2447 Clintonville Rd, Winchester, KY 40391
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  /14

  $225,000

  • Land
  • 18 Acres
  • $12,242 per Acre

  9711 Ironworks Rd, Winchester, KY 40391

  Escape to your own slice of paradise with this stunning 18.38-acre rural farm, nestled in the serene rolling hills of Winchester, Kentucky. This property offers the perfect blend of tranquility and convenience, far enough from town to unwind, yet just a short drive to Winchester's amenities. 18.38 acres of mostly clear land with some wooded areas, ideal for horses, cattle, or other livestock.

  Jessica Maloney Denniston Realty

  9711 Ironworks Rd, Winchester, KY 40391
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  /2

  $195,000

  • Land
  • 8 Acres
  • $23,353 per Acre

  6699 Boonesboro Rd, Winchester, KY 40391

  READY TO BUILD OR HUNT? We have the perfect spot for you! Mostly wooded 8.35 acres, tract 2B, of green, treed, Bluegrass Heaven. Close proximity to I 75 and I 64 as well as Lexington, Richmond, and Winchester. Bring your own builder or we can help you find one!

  Jennifer Ray RE/MAX Elite Lexington

  6699 Boonesboro Rd, Winchester, KY 40391
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  /4

  $100,000

  • Land
  • 2.62 Acres
  • $38,168 per Acre

  100 Spencer Ln, Winchester, KY 40391

  Eskippakithiki overlooks development. Has a 2.615 acre lot (parcel #8) available for sale waiting for you to build your dream home with beautiful views of serene countryside.

  Priscila Hale FC Tucker Bluegrass

  100 Spencer Ln, Winchester, KY 40391
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  /32

  $495,000

  • Land
  • 51 Acres
  • $9,698 per Acre

  750 Providence Ln, Winchester, KY 40391

  Welcome to your own slice of country paradise tucked away in southern Clark County! This 51+ acre tract offers a mixture of cleared pasture and mature woods, ideal for a variety of uses including cattle, crops, horses, recreation, or even your dream home site. Currently enjoyed as a private recreational family farm, the property already has electricity in place and features a cistern at an old

  Michelle Blackburn RE/MAX Creative, Winchester

  750 Providence Ln, Winchester, KY 40391
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  /39

  $472,000

  • 3 Beds
  • 2 Baths
  • 2,727 Sq Ft

  865 Pretty Run Rd, Winchester, KY 40391

  Situated on 1.5 acres along a sought after country road, this one level home features a split bedroom layout with a primary suite that includes an en suite bath and walk in closet. The living room offers vaulted ceilings, hardwood floors, and a gas log fireplace, opening to a dining area and an eat in kitchen. A sunroom provides additional living space with skylights and views of the backyard.

  Shane Underwood Keller Williams Commonwealth

  865 Pretty Run Rd, Winchester, KY 40391
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  /5

  $125,000

  • Land
  • 2.50 Acres
  • $50,000 per Acre

  1200 Craig Crossing, Winchester, KY 40391

  Welcome to Lot #18 in prestigious Thoroughbred Estates, an exceptional 2.5-acre corner parcel of gently rolling countryside, graced by a serene stream and picturesque views. This remarkable homesite offers the perfect canvas for your custom estate in one of western Clark County's most coveted locations, just off the highly sought-after McClure Road. A rare opportunity to claim a piece of

  N Seth Parker Lifstyl Real Estate

  1200 Craig Crossing, Winchester, KY 40391
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  /34

  $359,900

  • 3 Beds
  • 2 Baths
  • 1,305 Sq Ft

  3560 Wades Mill Rd, Winchester, KY 40391

  Welcome to your future farmette just minutes from town and the highway! With 5 acres offering privacy, beautiful views over the front pond, fenced in spaces for your animals and sheds and shelters, you are most of the way to tiny farm upon moving in. With a cozy 3 bed 2 bath home, and nearly all systems updated, as well as a fairly recent roof replacement, you are able to focus on customizing to

  Sarah MacHarg Kentucky Land and Home

  3560 Wades Mill Rd, Winchester, KY 40391
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  /46

  $389,900

  • Land
  • 20 Acres
  • $19,113 per Acre

  7875 Bybee Rd, Winchester, KY 40391

  Want 20 acres on which to roam and hunt or have a small farm operation? You will also have a nice 2021 3 bedroom, 2 full bath double wide home. There is a 3-bent barn where you can have a home for some animals. Primary bedroom has a walk-in shower, double sink, and walk-in closet. In fact, all bedrooms have a walk-in closet. Range, refrigerator and dishwasher stay. Front porch, deck on back and

  Joyce Ratliff Tom Goebel & Company

  7875 Bybee Rd, Winchester, KY 40391
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  /38

  $275,000

  • 4 Beds
  • 2 Baths
  • 1,924 Sq Ft

  217 Morris Rd, Winchester, KY 40391

  This is the one you've been waiting for! Room for the whole family with country charm just five minutes from the interstate. This 4-bedroom, 2-bath home features both a living room and a cozy den/family room, plus an open kitchen perfect for entertaining. Outside, enjoy an above-ground pool and a versatile tiny home/shed with plumbing and electric nearby—ideal as a man cave, she shed, or

  Patrick Arvin Keller Williams Commonwealth

  217 Morris 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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  /40

  $332,000

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

  13544 Irvine Rd, Winchester, KY 40391

  Experience Stunning Sunrises and Starry Nights!Nestled on nearly 4 peaceful acres, this charming brick ranch offers the tranquility of country living with modern comfort. Surrounded by a beautiful tree grove, the home features a full walk-out basement with exciting potential—finish the lower level and additional bathroom to expand your living space!Inside, you'll find 3 spacious

  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
  • 1,855 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

  Rex Hall United Real Estate Bluegrass

  250 Evergreen Dr, Winchester, KY 40391
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  /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
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  /3

  $430,000

  • 3 Beds
  • 2 Baths
  • 1,855 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

  Rex Hall United Real Estate Bluegrass

  220 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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  /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

  $475,000

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

  1731 Ford Hampton Rd, Winchester, KY 40391

  Price Improvement Reflects Room forPersonal Updates!Recent price adjustment provides buyers the opportunity to add their own style with updates like fresh paint or new flooring. This spacious property offers exceptional value and strong potential in a sought-after area.Versatile Home on 5.47 Acres with Horse Barn & Multi-Unit Living.Welcome to your private hilltop retreat with

  Julie Wiggington RE/MAX Creative, Winchester

  1731 Ford Hampton Rd, Winchester, KY 40391
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  /43

  $275,000

  • 4 Beds
  • 2 Baths
  • 1,539 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

  $1,600,000

  • Land
  • 55 Acres
  • $29,091 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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