16,242

Winchester, KY Homes

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  • /2

    $78,500

    • Land
    • 9,600 Sq Ft
    • $356,171 per Acre

    Lot 4 Plantations Dr, Winchester, KY 40391

    NOW SELLING SFH Buildable Lots of 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

    Agent Photo

    Melia Hord

    MELIA Realty LLC

    Lot 4 Plantations Dr, Winchester, KY 40391
  • /14

    $1,995 Per Month

    • 3 Beds
    • 2 Baths
    • 1,612 Sq Ft
    • Now Pre Leasing 3 Bedroom 2 Bath Luxury Ranch Home In Winchester Ky!

    101 Bellbrook Ln, Winchester, KY 40391

    Welcome to a place where luxury, comfort, and convenience come together. 101 Bellbrook is a stunning 3-bedroom, 2-full-bath ranch-style home thoughtfully designed for those looking for more than just a place to live it’s a place to truly feel at home. Step inside and discover an open-concept floor plan with spacious living areas, elegant finishes, stainless steel appliances, and a

    101 Bellbrook Ln, Winchester, KY 40391
  • /24

    $277,500

    Sold Aug 21, 2025

    10 Howard Dr, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 1,588 Sq Ft
    • Built 1961

    Last Sold Summary

    • 3% Below List Price
    • $175/SF
    • 0 Days On Market

    Current Estimated Value $287,808

    Last Listing Agent Holly Goeing The Agency

    10 Howard Dr, Winchester, KY 40391
    • /30

      Est $234,337

      Not Listed For Sale

      3604 Pine Ridge Rd, Winchester, KY 40391

      • 3 Beds
      • 2 Baths
      • 1,280 Sq Ft
      • Built 1998
      3604 Pine Ridge Rd, Winchester, KY 40391

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Patty Adams Rector Hayden Realtors

  • /23

    $250,000

    • Land
    • 14.51 Acres
    • $17,228 per Acre

    3056 Irvine Rd, Winchester, KY 40391

    Discover the perfect blend of beauty, privacy, and opportunity with this stunning 14.511-acre tract on Irvine Road. Featuring gently rolling hills, this property offers multiple ideal building sites to bring your dream home to life, whether you're envisioning a modern farmhouse, barndominium, or private country retreat. A barn is already in place, adding immediate functionality for storage,

    Agent Photo

    Christa Joynt

    Keller Williams Commonwealth

    3056 Irvine Rd, Winchester, KY 40391
  • /25

    $1,850 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,879 Sq Ft
    • Winchester KY welcomes you home 20260804

    230 Prescott Ln, Winchester, KY 40391

    Located in a desirable neighborhood, this spacious house offers 3 bedrooms and 2.5 bathrooms, providing ample space for you and your loved ones. The backyard is complete with a privacy fence, ensuring a serene and secluded atmosphere for outdoor activities. Step out onto the deck and enjoy the fresh air, and enjoy gatherings with friends and family. With a 2 car oversized attached garage, you'll

    230 Prescott Ln, Winchester, KY 40391
  • /14

    $320,000

    Sold Oct 17, 2025

    3431 Colby Rd, Winchester, KY 40391

    • 4 Beds
    • 2 Baths
    • 5,237 Sq Ft
    • Built 1955

    Last Sold Summary

    • 3% Below List Price
    • $61/SF
    • 7 Days On Market

    Current Estimated Value $339,816

    Last Listing Agent Holly Goeing The Agency

    3431 Colby Rd, Winchester, KY 40391
    • /13

      Est $141,026

      Not Listed For Sale

      2431 Pine Ridge Rd, Winchester, KY 40391

      • 2 Beds
      • 1 Bath
      • 1,113 Sq Ft
      • Built 1920
      2431 Pine Ridge Rd, Winchester, KY 40391

      Last Sold Summary

      • 74 Days On Market

      Last Listing Agent A. Rebecca Woods Woods Realty Group

  • /2

    $78,500

    • Land
    • 9,600 Sq Ft
    • $356,171 per Acre

    241 Plantations Dr Unit LOT 7, Winchester, KY 40391

    Welcome to DEERLAWN at Royal Oaks--Clark County's Newest Approved Single-Family Home Community. Now offering the first 12 fully buildable homesites in Phase One, this is your opportunity to secure one of the very first lots in what is poised to become Winchester's premier new residential community. Lot #7 is now available and ready for you to bring your own builder and create the home you've

    Agent Photo

    Melia Hord

    MELIA Realty LLC

    241 Plantations Dr Unit LOT 7, Winchester, KY 40391
  • /25

    $1,395 Per Month

    • 3 Beds
    • 2 Baths
    • 975 Sq Ft
    • House for Rent

    222 Buffalo Trace, Winchester, KY 40391

    ESTIMATED TOTAL MONTHLY LEASING PRICE: $1490.99Base Rent: $1395.00*Resident Benefits Package: Starts at $30.99*Resident Internet Amenity: $65.00This three-bedroom home is perfectly situated in the desirable Buffalo Trace neighborhood of downtown Winchester, offering both convenience and comfort in a prime location. The property features luxury vinyl plank flooring throughout,

    222 Buffalo Trace, Winchester, KY 40391
  • /41

    $265,000

    Sold Nov 12, 2025

    130 Village Ct, Winchester, KY 40391

    • 4 Beds
    • 2.5 Baths
    • 1,988 Sq Ft
    • Built 1970

    Last Sold Summary

    • 2% Below List Price
    • $133/SF
    • 4 Days On Market

    Current Estimated Value $276,408

    Last Listing Agent Joyce Ratliff Tom Goebel & Company

    130 Village Ct, Winchester, KY 40391
    • /101

      Est $366,244

      Not Listed For Sale

      3642 Crowe Ridge Rd, Winchester, KY 40391

      • 3 Beds
      • 2 Baths
      • 1,928 Sq Ft
      • Built 1953
      3642 Crowe Ridge Rd, Winchester, KY 40391

      Last Sold Summary

      • 121 Days On Market

      Last Listing Agent Maggie Napier Napier Realtors

  • /2

    $78,500

    • Land
    • 9,600 Sq Ft
    • $356,171 per Acre

    229 Plantations Dr Unit LOT 1, Winchester, KY 40391

    **Welcome to DEERLAWN at Royal Oaks—Clark County's Newest Approved Single-Family Home Community.** Now offering the **first 12 fully buildable homesites** in **Phase One**, this is your opportunity to secure one of the very first lots in what is poised to become **Winchester's premier new residential community**. **Lot #1** is now available and ready for you to bring your own builder and create

    Agent Photo

    Melia Hord

    MELIA Realty LLC

    229 Plantations Dr Unit LOT 1, Winchester, KY 40391
  • /12

    $1,300 Per Month

    • 3 Beds
    • 1 Bath
    • 1,123 Sq Ft
    • 3-Bed 1-Bath House

    136 Georgia St, Winchester, KY 40391

    136 Georgia Street in Winchester, KY is a newly renovated 3-bedroom, 1-bath home that blends updated finishes with classic porch appeal. The property offers both a front porch and back porch for outdoor space and includes washer/dryer hook-ups for laundry convenience. Thoughtfully refreshed interiors provide a comfortable living environment in a convenient location.Rental

    136 Georgia St, Winchester, KY 40391
  • /64

    $929,000

    Sold Sep 05, 2025

    1110 Craig Crossing, Winchester, KY 40391

    • 4 Beds
    • 2.5 Baths
    • 2,670 Sq Ft
    • Built 2025

    Last Sold Summary

    • 6% Below List Price
    • $348/SF
    • 23 Days On Market

    Current Estimated Value $668,630

    Last Listing Agent Michael Hilario The Agency

    1110 Craig Crossing, Winchester, KY 40391
    • /16

      Est $111,000

      Not Listed For Sale

      4523 Trapp Goffs Corner Rd, Winchester, KY 40391

      • Studio
      • 1,271 Sq Ft
      • Built 1974
      4523 Trapp Goffs Corner Rd, Winchester, KY 40391

      Last Sold Summary

      • 178 Days On Market

      Last Listing Agent Whitney Ensor Ensor Real Estate, LLC

  • /2

    $78,500

    • Land
    • 9,600 Sq Ft
    • $356,171 per Acre

    237 Plantations Dr Unit LOT 5, Winchester, KY 40391

    **Welcome to DEERLAWN at Royal Oaks--Clark County's Newest Approved Single-Family Home Community.** Now offering the **first 12 fully buildable homesites** in **Phase One**, this is your opportunity to secure one of the very first lots in what is poised to become **Winchester's premier new residential community**. **Lot #5** is now available and ready for you to bring your own builder and create

    Agent Photo

    Melia Hord

    MELIA Realty LLC

    237 Plantations Dr Unit LOT 5, Winchester, KY 40391
  • /6

    $799 Per Month

    • 1 Bed
    • 1 Bath
    • Condo for Rent

    7 Calloway St Unit 7 Calloway St #1, Winchester, KY 40391

    7 Calloway St Unit 7 Calloway St #1, Winchester, KY 40391
  • /35

    $285,000

    Sold May 01, 2026

    192 Prescott Ln, Winchester, KY 40391

    • 3 Beds
    • 2.5 Baths
    • 1,550 Sq Ft
    • Built 2007

    Last Sold Summary

    • 4% Above List Price
    • $184/SF
    • 1 Day On Market

    Current Estimated Value $280,900

    Last Listing Agent Joy Murphy United Real Estate Bluegrass

    192 Prescott Ln, Winchester, KY 40391
    • /40

      Est $382,880

      Not Listed For Sale

      409 Kiddville Rd, Winchester, KY 40391

      • 3 Beds
      • 2 Baths
      • 2,840 Sq Ft
      • Built 1971
      409 Kiddville Rd, Winchester, KY 40391

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Natalie Avant Berkshire Hathaway HomeServices Foster Realtors

  • /2

    $78,500

    • Land
    • 9,600 Sq Ft
    • $356,171 per Acre

    233 Plantations Dr Unit LOT 3, Winchester, KY 40391

    Welcome to DEERLAWN at Royal Oaks--Clark County's Newest Approved Single-Family Home Community. Now offering the first 12 fully buildable homesites in Phase One, this is your opportunity to secure one of the very first lots in what is poised to become Winchester's premier new residential community. Lot #3 is now available and ready for you to bring your own builder and create the home you've

    Agent Photo

    Melia Hord

    MELIA Realty LLC

    233 Plantations Dr Unit LOT 3, Winchester, KY 40391
  • /18

    $1,125 Per Month

    • 2 Beds
    • 1.5 Baths
    • 960 Sq Ft
    • Lovely Townhouse in Winchester! All Electric, Off-Street Parking, W/D Hookups, Small Pets Ok!

    356 Oxford Dr, Winchester, KY 40391

    NOW AVAILABLE! Attractive Townhouse at 356 OXFORD DRIVE, WINCHESTER! Eat-In Kitchen includes Stove, Refrigerator, and Dishwasher; Washer/Dryer hookups; Off-Street Parking with 2 parking spaces; Ceiling Fans; All Electric! Beautiful Wood-Look LVT Flooring; Lots of Closet Space.Located within an HOA in the Orchard Hill Subdivision. Private Patio. Small Pets Ok! (Cats, and Dogs 35 lbs and

    356 Oxford Dr, Winchester, KY 40391
  • /29

    $285,000

    Sold Jun 12, 2026

    426 E Broadway St, Winchester, KY 40391

    • 5 Beds
    • 2 Baths
    • 1,838 Sq Ft
    • Built 1945

    Last Sold Summary

    • 1% Below List Price
    • $155/SF
    • 12 Days On Market

    Current Estimated Value $280,777

    Last Listing Agent Alyssa M Boley Coldwell Banker McMahan

    426 E Broadway St, Winchester, KY 40391
    • /39

      Est $406,781

      Not Listed For Sale

      900 Vienna Rd, Winchester, KY 40391

      • 3 Beds
      • 2 Baths
      • 2,314 Sq Ft
      • Built 2005
      900 Vienna Rd, Winchester, KY 40391

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Devin Ramsey Berkshire Hathaway HomeServices Foster Realtors

  • /35

    $245,000

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

    216 Robyn Dr, Winchester, KY 40391

    Meticulously maintained 3-bedroom, 2-bath home on a full basement with wonderful curb appeal! Beautiful landscaping and a welcoming covered front porch invite you into this charming home. Inside, you'll find a warm and inviting main level featuring handsome hardwood flooring, a cozy fireplace, and a spacious living area. The adorable kitchen offers plenty of cabinet and counter space, making meal

    Agent Photo

    Robin Jones

    Keller Williams Legacy Group

    216 Robyn Dr, Winchester, KY 40391
  • /14

    $955 Per Month

    • 2 Beds
    • 1 Bath
    • Condo for Rent

    265 S Highland St Unit 4, Winchester, KY 40391

    Welcome to our charming apartment in Winchester, KY! This apartment boasts beautiful wood floors throughout, creating a warm and inviting atmosphere. Enjoy the convenience of a large yard and an in-unit laundry room. Located close to downtown and shopping, you'll have easy access to all the amenities Winchester has to offer. Don't miss out on the opportunity to call this unique apartment

    265 S Highland St Unit 4, Winchester, KY 40391
  • /19

    $288,500

    Sold Feb 24, 2026

    729 Wayland Dr, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 1,966 Sq Ft
    • Built 1980

    Last Sold Summary

    • 4% Below List Price
    • $147/SF
    • 92 Days On Market

    Current Estimated Value $288,325

    Last Listing Agent Brittany Beer eXp Realty, LLC

    729 Wayland Dr, Winchester, KY 40391
    • /23

      Est $821,822

      Not Listed For Sale

      1275 Old Log Lick Rd, Winchester, KY 40391

      • 3 Beds
      • 2 Baths
      • 1,392 Sq Ft
      • Built 1982
      1275 Old Log Lick Rd, Winchester, KY 40391

      Last Sold Summary

      • 474 Days On Market

      Last Listing Agent John Wilson Bluegrass Properties Group

  • /2

    $78,500

    • Land
    • 9,600 Sq Ft
    • $356,171 per Acre

    239 Plantations Dr Unit LOT 6, Winchester, KY 40391

    **Welcome to DEERLAWN at Royal Oaks--Clark County's Newest Approved Single-Family Home Community.** Now offering the **first 12 fully buildable homesites** in **Phase One**, this is your opportunity to secure one of the very first lots in what is poised to become **Winchester's premier new residential community**. **Lot #6** is now available and ready for you to bring your own builder and create

    Agent Photo

    Melia Hord

    MELIA Realty LLC

    239 Plantations Dr Unit LOT 6, Winchester, KY 40391
  • /14

    $125,000

    Sold Apr 01, 2026

    464 Ecton Rd, Winchester, KY 40391

    • Land
    • 1.03 Acres
    • $121,359 per Acre

    Last Sold Summary

    • 16% Below List Price
    • 3 Days On Market

    Current Estimated Value $130,253

    Last Listing Agent Vickie Skeens RE/MAX Elite Lexington

    464 Ecton Rd, Winchester, KY 40391
    • /44

      Est $322,214

      Not Listed For Sale

      2482 Mina Station Rd, Winchester, KY 40391

      • 3 Beds
      • 2 Baths
      • 1,756 Sq Ft
      • Built 1962
      2482 Mina Station Rd, Winchester, KY 40391

      Last Sold Summary

      • 24 Days On Market

      Last Listing Agent Stephanie Hacker Kentucky Residential Real Estate, LLC

  • /35

    $314,900

    $5K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 2,082 Sq Ft

    128 Cherokee Dr, Winchester, KY 40391

    Welcome to 128 Cherokee Drive, where space, versatility, and convenience come together! This all-brick split-foyer home offers 5 bedrooms, 2 full bathrooms, and over 2,000 square feet of comfortable living space, making it ideal for growing families, multi-generational living, or anyone needing extra room. The main level features a bright and inviting living room, while the finished lower level

    Agent Photo

    Tyler Hurst

    Oak & Acre

    128 Cherokee Dr, Winchester, KY 40391
  • /33

    $332,000

    Sold Oct 14, 2025

    1831 Kiddville Rd, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 1,756 Sq Ft
    • Built 1963

    Last Sold Summary

    • 5% Below List Price
    • $189/SF
    • 82 Days On Market

    Current Estimated Value $329,620

    Last Listing Agent Joshua Davis The Agency

    1831 Kiddville Rd, Winchester, KY 40391
    • /43

      Est $281,444

      Not Listed For Sale

      2270 Mina Station Rd, Winchester, KY 40391

      • 3 Beds
      • 2 Baths
      • 1,358 Sq Ft
      • Built 1971
      2270 Mina Station Rd, Winchester, KY 40391

      Last Sold Summary

      • 72 Days On Market

      Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  • /21

    $175,000

    • Land
    • 11.36 Acres
    • $15,402 per Acre

    2996 Irvine Rd, Winchester, KY 40391

    Discover the perfect blend of convenience and countryside charm with this beautiful 11+ acre tract located just outside of Winchester in Clark County. Offering gently rolling terrain and multiple potential building sites, this property provides an ideal setting for your dream home, mini-farm, or private retreat.Enjoy the peace and privacy of rural living without sacrificing accessibility and just

    Agent Photo

    Christa Joynt

    Keller Williams Commonwealth

    2996 Irvine Rd, Winchester, KY 40391
  • /67

    $410,000

    Sold Jul 09, 2026

    233 Schollsville Rd, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 1,347 Sq Ft
    • Built 2016

    Last Sold Summary

    • 2% Above List Price
    • $304/SF
    • 1 Day On Market

    Current Estimated Value $397,787

    Last Listing Agent Bill Deaton Keller Williams Legacy Group

    233 Schollsville Rd, Winchester, KY 40391
    • /70

      Est $596,711

      Not Listed For Sale

      519 Right Angle Rd, Winchester, KY 40391

      • 6 Beds
      • 3 Baths
      • 3,712 Sq Ft
      • Built 2000
      519 Right Angle Rd, Winchester, KY 40391

      Last Sold Summary

      • 186 Days On Market

      Last Listing Agent The Prather Team - Michael Prather Keller Williams Bluegrass Realty

  • /74

    $329,000

    $10K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,068 Sq Ft

    13 Bel Air Dr, Winchester, KY 40391

    Don't let this charming brick ranch fool you—it's what's waiting out back that will absolutely steal the show! Nestled in the heart of Winchester, this 3BR/3BA home offers an incredible backyard oasis that's perfect for entertaining, relaxing, and making memories all summer long. The sparkling in-ground pool is the centerpiece of this private retreat, surrounded by expansive concrete decking and

    Agent Photo

    Robin Jones

    Keller Williams Legacy Group

    13 Bel Air Dr, Winchester, KY 40391
  • /8

    $160,000

    Sold Jul 13, 2026

    107 Patio St, Winchester, KY 40391

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft
    • Built 1997

    Last Sold Summary

    • $185/SF
    • 0 Days On Market

    Current Estimated Value $160,815

    Last Listing Agent Sherry Stephens Murphy Realty Group

    107 Patio St, Winchester, KY 40391
    • /69

      Est $380,323

      Not Listed For Sale

      3975 Wills Rupard Rd, Winchester, KY 40391

      • 4 Beds
      • 3 Baths
      • 3,021 Sq Ft
      • Built 1986
      3975 Wills Rupard Rd, Winchester, KY 40391

      Last Sold Summary

      • 218 Days On Market

      Last Listing Agent Tonya Morrow KY Local

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