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Winchester, KY Homes for Sale with Acreage

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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
  • /34

    $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
  • /49

    $450,000

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

    233 Cunningham Ln, Winchester, KY 40391

    Mini Farm Alert! This fabulous homestead is located less than 2 miles off the Mountain Parkway making it easily accessible. One level, ranch home that features 3 bedrooms, a luxurious primary ensuite... corner jetter tub, seperate walk in shower with glass door, double bowl raised height vanity and a linen closet complete the bathroom and the bedroom has vaulted ceilings, walk in closet and

    Amanda Marcum Berkshire Hathaway HomeServices Foster Realtors

    233 Cunningham Ln, Winchester, KY 40391
  • /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
  • /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
  • /3

    $380,000 New Construction

    • 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
  • /15

    $600,000

    • 8 Beds
    • 4 Baths
    • 5,046 Sq Ft

    101 S Burns Ave Unit 1,2,3,4, Winchester, KY 40391

    Step into a rare investment opportunity in the heart of downtown Winchester! This beautifully renovated 4-plex offers charm, space, and convenience — all within a fully restored historic building. Each of the four spacious units boasts approximately 1,296 sq ft, blending timeless character with modern updates. The entire property has been thoughtfully renovated in 2021, including a brand-new

    Priya Patel-Rossetti Big Blue Realty

    101 S Burns Ave Unit 1,2,3,4, Winchester, KY 40391
  • /4

    $67,500

    • Land
    • 1.92 Acres
    • $35,156 per Acre

    12569 Ironworks Rd, Winchester, KY 40391

    Build your dream home in the stunning ESKIPPAKITHIKI OVERLOOKS! Or hold as investment property and watch this land grow in value. This lot containing 1.919 acres, offer unparalleled views of a serene, natural setting. Perfect for a private retreat or family estate, this property invites you to design your ideal lifestyle surrounded by the beauty and tranquility. Don't miss your opportunity to own

    Kathryn Cheuvront Coldwell Banker McMahan

    12569 Ironworks Rd, Winchester, KY 40391
  • /13

    $74,900

    • Land
    • 2.14 Acres
    • $35,000 per Acre

    1751 Little Stoner Rd, Winchester, KY 40391

    Located at 1751 Little Stoner Rd in Winchester, this 2.139 acre building lot offers the kind of space and setting that's getting harder to find. Open land, rolling country views, and room to create something truly your own, all while staying conveniently connected to the places that matter most. Enjoy the rare balance of peaceful surroundings with easy access. You're just 20 minutes to Lexington,

    Kymberly McCreary EXP Realty, LLC

    1751 Little Stoner Rd, Winchester, KY 40391
  • /3

    $345,000 New Construction

    • 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
  • /39

    $384,900 New Construction

    • 4 Beds
    • 4.5 Baths

    3600 Crowe Ridge Rd, Winchester, KY 40391

    Newly constructed unfinished multigenerational home located on 4 acres. Separate level living with 2 kitchens, 2 laundry rooms, and an en-suite for every bedroom. The main floor features 21' cathedral ceilings, 8' doors and 15 3'x6' windows creating a spacious home boasting panoramic views. Includes an additional 20'x24' loft space and 2 flex rooms with ANSI standard windows. Secondary living

    Maggie Napier Napier Realtors

    3600 Crowe Ridge Rd, Winchester, KY 40391
  • /55

    $425,000

    • 5 Beds
    • 3.5 Baths
    • 2,564 Sq Ft

    6504 Combs Ferry Rd, Winchester, KY 40391

    Welcome to an extraordinary residence where luxury, craftsmanship, and natural beauty come together. This house has been taken down to the studs, and thoughtfully rebuilt. This two story home with a walk-out basement sits on 8 acres, adjoining the Lower Howard Creek Preserve, offering unmatched privacy and an exceptional standard of living. The owner spared no expense—every detail has been

    Lucy Martin Jenkins United Real Estate Bluegrass

    6504 Combs Ferry Rd, Winchester, KY 40391
  • /7

    $180,000

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

    1030 Craig Crossing Rd, Winchester, KY 40391

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

    Keith Wilson Coldwell Banker McMahan

    1030 Craig Crossing Rd, Winchester, KY 40391
  • /14

    $159,900

    • Land
    • 2.66 Acres
    • $60,113 per Acre

    590 Craig Crossing, Winchester, KY 40391

    Don't let this opportunity pass you by again. This prime lot in Thoroughbred Estates is back on the market due to Current owners change of plans. This lot is ready for your new home with a beautiful setting and located close to Winchester and Lexington in a new Luxury Subdivision. Watch the sun set each night from your rear deck or pool. Call today!!!

    Keith Wilson Coldwell Banker McMahan

    590 Craig Crossing, Winchester, KY 40391
  • /13

    $400,000

    • Land
    • 2.19 Acres
    • $182,648 per Acre

    145 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

    145 Codella Dr, Winchester, KY 40391
  • /3

    $430,000 New Construction

    • 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

    Rex Hall United Real Estate Bluegrass

    265 Evergreen Dr, Winchester, KY 40391
  • /59

    $825,000

    • 2 Beds
    • 1.5 Baths
    • 2,361 Sq Ft

    455 Davis Ln, Winchester, KY 40391

    Hunter's Paradise! This beautiful 85 acre farm is nestled in the heart of Clark County. Wildlife is abundant as you travel throughout the property. The home is very spacious with a full mother in law suite. Entertain friends at the full bar, while enjoying the wood burning stove. A functioning greenhouse expands the possibilities for year round gardening. If you are looking for little piece of

    Dale Hatton Dream Maker Realty, LLC

    455 Davis Ln, Winchester, KY 40391
  • /9

    $206,000

    • Land
    • 7.77 Acres
    • $26,512 per Acre

    368 Flanagan Station Rd, Winchester, KY 40391

    Build your dream retreat on this beautiful 7.77-acre parcel nestled in a peaceful rural setting just outside Winchester. The gently rolling terrain provides a serene backdrop for your custom home, hobby farm, or equestrian space, offering plenty of room to roam, garden, or simply enjoy the privacy. With easy access from Flanagan Station Road, this property combines a quiet country feel with

    Shari Frasure Keller Williams Commonwealth

    368 Flanagan Station Rd, Winchester, KY 40391
  • /84

    $849,900

    • 4 Beds
    • 3.5 Baths
    • 4,922 Sq Ft

    2509 Mount Sterling Rd, Winchester, KY 40391

    Embrace Bluegrass living with this beautiful fieldstone ranch on 10+ acres in the heart of horse country. Just minutes from interstate access, yet surrounded by rolling hills and scenic views, this mini farm offers a larger barn with 6 stalls, including water and electric connection, 90 foot roof hangover on the barn, 5 paddocks, each with their own gate and water ran along each paddock. The home

    Josh Wood Freedom Realty & Property Management

    2509 Mount Sterling Rd, Winchester, KY 40391
  • /6

    $450,000

    550 E Broadway St, Winchester, KY 40391

    Prime land located on the outskirts of Winchester ready for possible development. Parcel has frontage on both East Broadway and Washington Street. Land is currently zoned A-1. Utilities available. The future awaits!!!

    Keith Wilson Coldwell Banker McMahan

    550 E Broadway St, Winchester, KY 40391
  • /42

    $450,000

    • 5 Beds
    • 3 Baths
    • 3,718 Sq Ft

    1503 Schollsville Rd, Winchester, KY 40391

    Do you ever wonder what it would be like to live in the days of "Gone with the Wind"? Well, here is your chance to own your own personal "Tara". Spacious country home with acreage suitable for children, pets, and livestock. This home is perfect for escaping city life and crowds. Home consists of 5 bedrooms, 3 full bathrooms, Living Room, Dining Room, large Kitchen, room for an office or craft

    Keith Wilson Coldwell Banker McMahan

    1503 Schollsville Rd, Winchester, KY 40391
  • /5

    $70,000

    • Land
    • 1.72 Acres
    • $40,698 per Acre

    12541 Ironworks Rd, Winchester, KY 40391

    Discover the perfect place to build your dream home in Eskippakithiki Overlooks. This beautiful 1.72 acre parcel offers ample space, peaceful surroundings, and stunning natural views. Enjoy the serenity of country living, this land provides an ideal canvas for a custom home or family getaway. Don't miss this opportunity to secure your own piece of paradise.

    Daniela Virguez National Real Estate

    12541 Ironworks Rd, Winchester, KY 40391
  • /10

    $775,000

    • Land
    • 3 Acres
    • $258,333 per Acre

    609 Bullion Blvd Unit 3A, 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, and

    Greg Leveridge Block + Lot Real Estate

    609 Bullion Blvd Unit 3A, Winchester, KY 40391
  • /2

    $2,000,000

    • Land
    • 17.87 Acres
    • $111,919 per Acre

    1509 Boonesboro Rd, Winchester, KY 40391

    17.87 Acre farm available for sale. Ideal location for redevelopment. Gently rolling topography. Corner lot with excellent visibility. Water, electric, sewer, gas and telecommunications available. Conveniently located near RD Campbell Junior High School, George Rogers Clark High School & Winchester Country Club. Located 3 miles south of Interstate 64. Signalized corner lot at Boonesboro Rd. &

    Cheryl Johnston CMI Properties

    1509 Boonesboro Rd, Winchester, KY 40391
  • /28

    $799,900

    • Land
    • 13.19 Acres
    • $60,644 per Acre

    1600 Ironworks Rd, Winchester, KY 40391

    This property has it all! Easy access to Veterans Memorial Bypass, I-64, and downtown Winchester, plus entrances on Ironworks and clear visibility from the Bypass. This does have sewer and water located on the property. Full of potential possibilities zoned Planned Development and more acreage is available if needed. The property access is a driveway off Ironworks Road across from Center Drive

    Josh Wood Freedom Realty & Property Management

    1600 Ironworks Rd, Winchester, KY 40391
  • /50

    $824,900

    • 4 Beds
    • 3 Baths
    • 3,311 Sq Ft

    7300 Old Boonesboro Rd, Winchester, KY 40391

    This beautiful home sits on over 7 acres of peaceful countryside. The private outdoor space includes a huge deck with a lovely view and an inviting covered front porch. The backyard would make the perfect space for your own dream swimming pool. Since the property has a 3-car detached garage; a 2-car attached garage plus a 1275 square feet equipment building there is plenty of space for all of

    Vickie Skeens RE/MAX Elite Lexington

    7300 Old Boonesboro Rd, Winchester, KY 40391
  • /34

    $315,000

    • 2 Beds
    • 1 Bath
    • 1,531 Sq Ft

    1508 Ford Hampton Rd, Winchester, KY 40391

    Welcome home to this adorable 2 bedroom, 1 bathroom farmhouse on 5 peaceful acres. Inside, the layout is open and inviting with LVP and hardwood flooring throughout with a tiled bath. The kitchen and family room flow together and feature beautiful exposed wood beams that are hundreds of years old and reclaimed from an old church. A wood-burning stove in the family room adds warmth and character

    Michelle Blackburn RE/MAX Creative, Winchester

    1508 Ford Hampton Rd, Winchester, KY 40391

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