Winchester, KY Homes for Sale with Acreage

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  $425,000

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft

  4305 Old Boonesboro Rd, Winchester, KY 40391

  

  Brenda Sipes

  WEICHERT REALTORS - ABG Properties

  (859) 549-3072

  4305 Old Boonesboro Rd, Winchester, KY 40391
• Explore Winchester

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  /23

  $498,900

  2996/3056 Irvine Rd, Winchester, KY 40391

  Rare find! Gorgeous 25 acres of gently rolling land with a barn and creek is perfect for building your dream home and creating your homestead! Don't miss this opportunity! This is farm is conveniently located 20 miles from Hamburg and 5 miles from the Winchester bypass. No city sewage. Deed restrictions apply. Relax and enjoy the spectacular views. Get ready to enjoy life! Land consists of 2

  Lura Justice Rector Hayden Realtors

  2996/3056 Irvine Rd, Winchester, KY 40391
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  /19

  $499,000

  • Land
  • 36.94 Acres
  • $13,508 per Acre

  1455B Ky-89 Lot Unit Wp001, Winchester, KY 40391

  Don't miss this rare chance to own 36.45 premium acres on the outskirts of Winchesteran unbeatable blend of open farmland, development potential, and a truly top-tier location. Just minutes from I-64 and a quick drive to Lexington, this tract offers the convenience buyers want with the space and freedom they rarely find. The gorgeous rolling fields make this property ideal for farming, hay

  Greg Meade Whitetail Properties Real Estate

  1455B Ky-89 Lot Unit Wp001, Winchester, KY 40391
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  /51

  $775,000

  • 5 Beds
  • 3.5 Baths
  • 2,904 Sq Ft

  1783 Gay Evans Rd, Winchester, KY 40391

  Welcome to your dream homestead retreat! Tucked away on 7.27 beautiful acres, this stunning 5-bedroom, 4-bath home offers the perfect blend of comfort, function, and country living. From the inviting front porch sunsets to the resort-style outdoor space, this property has everything you've been searching for. Step inside to the two story foyer that leads to an open-concept main level featuring

  Lucy Martin Jenkins United Real Estate Bluegrass

  1783 Gay Evans Rd, Winchester, KY 40391
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  /100

  $1,789,000

  • 3 Beds
  • 2.5 Baths
  • 4,518 Sq Ft

  3166 Colby Rd, Winchester, KY 40391

  PRICE REDUCED and sellers are offering a 25,000 allowance at closing to spend as you wish!! Welcome to this beautiful 33± acre estate, offering the perfect blend of country charm, modern comfort, and endless opportunity. The stately historical home, built in 1919, retains timeless character and can be registered with the Historical Home Society. Enjoy stunning mountain views — located at one of

  Alyssa M Boley Coldwell Banker McMahan

  3166 Colby Rd, Winchester, KY 40391
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  /2

  $1,200,000

  • Land
  • 24.15 Acres
  • $49,689 per Acre

  1395 Two Mile Rd, Winchester, KY 40391

  PLANNED DEVELOPMENT INVESTMENT INVESTMENT OPPORTUNITY! Already zoned Planned Development! There is an approximately 24 acre tract zoned for all forms of Residential use. (In addition there is an approximately 21 acre Residential tract that adjoins the Winchester Country Club. The two Residential tracts have access to gravity flow sewer. Sewer maps available. The remaining

  Garnett Davis Tom Goebel & Company

  1395 Two Mile Rd, Winchester, KY 40391
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  /94

  $795,000

  • 4 Beds
  • 3.5 Baths
  • 4,584 Sq Ft

  4040 Muddy Creek Rd, Winchester, KY 40391

  A Farmhouse Retreat with Timeless Craftsmanship on 13.6 Acres Nestled on 13.6 rolling acres in Clark County, this custom built farmhouse captivates with soaring tongue-and-groove ceilings, rich woodwork, and thoughtful craftsmanship that sets this home apart. Oversized doors, custom cabinetry, and detailed finishes showcase the quality throughout, while two wood-burning fireplaces with homemade

  Julie Wiggington RE/MAX Creative, Winchester

  4040 Muddy Creek Rd, Winchester, KY 40391
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  /103

  $2,650,000

  • 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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  /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 Estate Services, LLC

  3385 Colby Rd, Winchester, KY 40391
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  /17

  $299,000

  • Land
  • 14.51 Acres
  • $20,606 per Acre

  3056 Irvine Rd, Winchester, KY 40391

  Own a genuine piece of Kentucky splendor! Beautiful 14.5 acres of gently rolling land is ideal for building your custom home! The property offers creek access and a barn with electric and water. Don't miss this opportunity to own a farm only 20 miles to Hamburg and 5 miles to Winchester Bypass. No city sewage. Deed restrictions apply. Additional parcel with 11.36 acres is also available. Perfect

  Lura Justice Rector Hayden Realtors

  3056 Irvine Rd, Winchester, KY 40391
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  /2

  $882,000

  • Land
  • 3.93 Acres
  • $224,427 per Acre

  Lot 1 - 12 Plantations Dr, Winchester, KY 40391

  NOW SELLING PHASE ONE: 12 Buildable Lots (minimum lot is 9600+ sqft) of PHASE ONE of Deerlawn's Development located at 2395 Paris Rd (Parent Listing). Earmarked as Winchester, Ky's most anticipated residential development consisting of an ambitious 274+-acre expansion formerly known as the well-established Royal Oaks/Plantation neighborhoods, Phase One has 12 lots ready for you to build your New

  Melia Hord Keller Williams Legacy Group

  Lot 1 - 12 Plantations Dr, Winchester, KY 40391
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  /2

  $150,000

  • Land
  • 2.11 Acres
  • $71,090 per Acre

  125 Knox Ct, Winchester, KY 40391

  Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

  John Wilson Bluegrass Properties Group

  125 Knox Ct, Winchester, KY 40391
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  $1,500,000

  1015 Old Stone Church Rd, Winchester, KY 40391

  Right off of Boonesboro Road lies 60.65± acres of Kentucky history waiting for its next chapter! This remarkable property sits along historic Howard's Creek and is located on the site of the original Bush Settlement—one of the earliest settlements in Kentucky. Formerly a working tobacco farm, this versatile acreage offers opportunities for cattle, hay, or crops, with timber and mineral rights

  Walker Mack Bluegrass Property Exchange

  1015 Old Stone Church Rd, Winchester, KY 40391
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  /87

  $3,100,000

  • 6 Beds
  • 5 Baths
  • 3,693 Sq Ft

  3049 Ironworks Rd, Winchester, KY 40391

  150 acres of pure Kentucky beauty in Winchester, on the market for the first time ever. This incredible cattle farm has been owned by the same family since 1803 and is now ready for its next chapter. With rolling land, four barns, two storage sheds, four ponds, a creek, and two homes, this estate is truly unmatched. If you've been waiting for your dream property, this is it.

  Zova Rothchild Keller Williams Legacy Group

  3049 Ironworks Rd, Winchester, KY 40391
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  $362,000

  • 5 Beds
  • 2 Baths
  • 1,952 Sq Ft

  1270 Sewell Shop Rd, Winchester, KY 40391

  Country Living with Convenience — 5 Fenced Acres in Winchester, KY Enjoy the perfect blend of peaceful country living and easy access to town with this well-maintained home on 5 fully fenced acres in Winchester, KY. Conveniently located just 30 minutes to Lexington, 5 miles to I-64, 10 minutes to Mt. Sterling, and 15 minutes to Winchester, this property offers country living without sacrificing

  Meggan Batey Keller Williams Legacy Group

  1270 Sewell Shop 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! Or hold as investment property and let the land grow in value. 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

  Kathryn Cheuvront Coldwell Banker McMahan

  150 Spencer Ln, Winchester, KY 40391
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  $775,000

  • Land
  • 2.6 Acres
  • $298,077 per Acre

  529 Bullion Blvd Unit 3B, Winchester, KY 40391

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

  Greg Leveridge Block + Lot Real Estate

  529 Bullion Blvd Unit 3B, Winchester, KY 40391
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  /2

  $14,100,000

  • Land
  • 274.52 Acres
  • $51,362 per Acre

  2395 Paris Rd, Winchester, KY 40391

  NOW PRE-SELLING: Deerlawn Development is Winchester, Ky's most anticipated residential development—an ambitious 274+-acre expansion formerly known as the well-established Royal Oaks/Plantation neighborhoods.
 Located at 2395 Paris Road, and positioned off I-64 at Exit 96 across from the rapidly expanding Industrial Park, Deerlawn is a master-planned community offering 438 single-family

  Melia Hord Keller Williams Legacy Group

  2395 Paris Rd, Winchester, KY 40391
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  /4

  $137,500

  • Land
  • 3.94 Acres
  • $34,898 per Acre

  12569 Ironworks Rd, Winchester, KY 40391

  Build your dream home in the stunning ESKIPPAKITHIKI OVERLOOKS! Looking for your next investment? This 3.940 acre parcel offers unlimited potential-whether you dream of building or simply holding land as it gows in value. Offering 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

  Kathryn Cheuvront Coldwell Banker McMahan

  12569 Ironworks Rd, Winchester, KY 40391
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  /19

  $125,000

  • Land
  • 4.01 Acres
  • $31,172 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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  /38

  $389,900

  • 4 Beds
  • 2 Baths
  • 2,659 Sq Ft

  6239 Old Boonesboro Rd, Winchester, KY 40391

  Welcome Home to the beautiful country! If you've been looking for quiet, space, and a place that truly feels like home, this charming Cape Cod on nearly 2 acres in Clark County checks all the boxes. Tucked into a peaceful rural setting yet conveniently located near I-75, I-64 and the Winchester Bypass, this property offers the best of country living with easy access to town. With over 2,600

  Kenya Woods United Real Estate Bluegrass

  6239 Old Boonesboro Rd, Winchester, KY 40391
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  /103

  $3,500,000

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

  5045 Van Meter Rd, Winchester, KY 40391

  Welcome to a truly exceptional 78-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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  /25

  $310,000

  • 2 Beds
  • 1 Bath
  • 1,170 Sq Ft

  398 Pine Ridge Rd, Winchester, KY 40391

  Discover the charm of country living at 398 Pine Ridge Rd in Winchester, KY. This inviting 2-bedroom, 1-bath home sits on 10 picturesque acres, offering the perfect retreat for those who love peace, privacy, and the beauty of the Kentucky countryside. Step inside to a warm and cozy interior with a simple, functional layout that feels like home the moment you walk in. Enjoy the outdoors from the

  Amie Hieneman ERA Select Real Estate

  398 Pine Ridge Rd, Winchester, KY 40391
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  /2

  $195,000

  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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  /13

  $1,250,000

  345 Providence Ln, Winchester, KY 40391

  Reasonable Offers Considered!! 120 Acres of Scenic Farmland in Winchester, KY. Discover the beauty and tranquility of country living on this remarkable 120-acre farm nestled in the heart of Clark County, Kentucky. Featuring a picturesque mix of rolling pastureland, mature woodlands, and pond, this property offers endless possibilities for farming, livestock, recreation, or building your dream

  Megan McCoy Keller Williams Legacy Group

  345 Providence Ln, Winchester, KY 40391
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  /9

  $500,000

  • Land
  • 1.52 Acres
  • $328,947 per Acre

  1005 Early Dr, Winchester, KY 40391

  Visibility, Access, Utilities on site per seller/per plat-buyer to verify, zoned B-3. 1.52 acres located at I-64 exit 96, Right in front of the Hampton Inn, buyer to verify and satisfy themselves to all aspects and information on property. and inspections sold as is. Buyer to Check with all utilities companies to very water electric and gas availability and locations on all utilities.

  Whitney Ensor Ensor Real Estate, LLC

  1005 Early Dr, Winchester, KY 40391
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  /14

  $650,000

  • Land
  • 3 Acres
  • $216,667 per Acre

  205 Codella Dr, Winchester, KY 40391

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

  Greg Leveridge Block + Lot Real Estate

  205 Codella Dr, Winchester, KY 40391
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  /6

  $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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  /2

  $550,000

  • Land
  • 1.53 Acres
  • $359,477 per Acre

  33-41 Winn Ave, Winchester, KY 40391

  Discover a rare opportunity in downtown Winchester with this assemblage of four vacant lots being sold together as a single offering. Zoned L1 and totaling approximately 1.53 acres, this property presents exceptional potential for redevelopment, infill housing, multiunit residential, mixeduse, or commercial concepts in a central location. Situated just steps from local shops, restaurants,

  Bob Sophiea eXp Realty, LLC

  33-41 Winn Ave, Winchester, KY 40391
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  /2

  $150,000

  • Land
  • 2.16 Acres
  • $69,444 per Acre

  120 Knox Ct, Winchester, KY 40391

  Looking for a place to build a Upscale home in Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

  John Wilson Bluegrass Properties Group

  120 Knox Ct, Winchester, KY 40391
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  /63

  $1,149,000

  • 3 Beds
  • 3.5 Baths
  • 3,672 Sq Ft

  2100 Irvine Rd Unit 40391, Winchester, KY 40391

  Seller will need 48 Hours to show, This log cabin is located on gently rolling 28 acres very few miles from town, you will think you are on vacation in the sparking pool, tastefully landscaped, fireplace in the great room which leads into a in law quarters, large kitchen that has been wonderfully remodeled with extensive detail, master suite is located on first floor, mud room, 3 1/2 baths,

  Mila Ensor Ensor Real Estate, LLC

  2100 Irvine Rd Unit 40391, Winchester, KY 40391
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  /14

  $129,800

  • Land
  • 2.3 Acres
  • $56,435 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

  Amanda Thomas The Agency

  110 Knox Ct, Winchester, KY 40391
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  /44

  $850,000

  • Land
  • 83.71 Acres
  • $10,154 per Acre

  7075 Ecton Rd, Winchester, KY 40391

  ABSOLUTE AUCTION — SELLS TO THE HIGHEST BIDDER REGARDLESS OF PRICE! Offered at Live On-Site Absolute Auction with Simulcast Internet Bidding, this exceptional 83.714± acre Clark County farm will sell on Saturday, March 7, 2026 at 10:30 AM (EST) at 7075 Ecton Rd, Winchester, KY 40391. Tract One: 36.825Acres, Tract Two: 5.196 Acres, Tract Three: 5.022 Acres Tract Four: 36.671 Acres The property

  Jonathan Noel Noel Auctioneers and Real Estate Advisors

  7075 Ecton Rd, Winchester, KY 40391
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  /15

  $925,000

  • Land
  • 3.77 Acres
  • $245,358 per Acre

  300 Rolling Hills Ln, Winchester, KY 40391

  Great location just off exit 96 on I-64 and easy access to the Mountain Parkway. Only 15 minutes from I-75. Located near the entrance to the Winchester Kentucky Industrial Park. 3.774 flat acres to build your next business location.

  Josh Wood Freedom Realty & Property Management

  300 Rolling Hills Ln, Winchester, KY 40391
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  /8

  $195,000

  • Land
  • 6.15 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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  $260,000

  • Land
  • 6.08 Acres
  • $42,763 per Acre

  190 Privacy Ln, Winchester, KY 40391

  6.08 acres settled in Clark County with access from both Privacy Ln and Little Stoner Rd. This property boasts a 30x56 with 10 foot wall Kentucky Steel Truss building with concrete floors, gas and wood burning heat, full bath, and a car lift. Additionally, there is a barn with a 3 bay shed attached.

  Jason Joseph Keller Williams Commonwealth

  190 Privacy Ln, Winchester, KY 40391
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  $925,000 New Construction

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

  1150 Craig Crossing, Winchester, KY 40391

  Stunning new construction offering 5 bedrooms, 3.5 bathrooms, sitting on roughly 2.5 serene acres. This home is surrounded by picturesque farmland and panoramic views. 4 bedrooms are located on the main level for ultimate convenience. Offering the perfect blend of space, style, and serenity. Features include open concept layout, spacious kitchen with kitchen island, granite counter tops, hidden

  Stephanie Hacker Kentucky Residential Real Estate, LLC

  1150 Craig Crossing, Winchester, KY 40391
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  /39

  $429,900

  • 3 Beds
  • 2.5 Baths
  • 2,258 Sq Ft

  233 Cunningham Ln, Winchester, KY 40391

  Welcome to 233 Cunningham Lane in Winchester, KY — a versatile mini farm offering 6.7 acres, multiple outbuildings, and a functional one-level ranch floor plan designed for comfort and flexibility. Conveniently located less than two miles from the Mountain Parkway, this property combines rural space with easy accessibility for commuting and everyday travel. The ranch-style home features 3

  Amanda Marcum Berkshire Hathaway HomeServices Foster Realtors

  233 Cunningham Ln, Winchester, KY 40391
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  /4

  $199,900

  • Land
  • 11.36 Acres
  • $17,597 per Acre

  2996 Irvine Rd, Winchester, KY 40391

  Are you looking to build your dream home in a quiet country setting with easy access to the Interstate? Look no further! This property offers it all! Gorgeous setting with the best views and creek access. This lovely farm is 11.36 acres of gently rolling country land, in a highly desirable area with easy access to interstate 64, the Mountain Parkway and Hamburg. No city sewage. Deed restrictions

  Lura Justice Rector Hayden Realtors

  2996 Irvine Rd, Winchester, KY 40391
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  /9

  $1,350,000

  • Land
  • 3.02 Acres
  • $447,020 per Acre

  155 April Way, Winchester, KY 40391

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

  Greg Leveridge Block + Lot Real Estate

  155 April Way, Winchester, KY 40391

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