16,575

Homes in ZIP Code 40391

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    • /27

      Est $290,979 Not Listed For Sale

      198 Hilltop Dr, Winchester, KY 40391

      • 4 Beds
      • 2 Baths
      • 1,780 Sq Ft
      • Built 1960
      198 Hilltop Dr, Winchester, KY 40391

      Last Sold Summary

      • 24% Above List Price
      • $132/SF
      • 0 Days On Market

      Last Sold Price $235,000

      Last Listing Agent Stephanie Hacker Kentucky Residential Real Estate, LLC

  • /26

    $165,000 Pending

    • 3 Beds
    • 1.5 Baths
    • 1,312 Sq Ft

    52 Judy Ann Ct, Winchester, KY 40391

    This charming 3-bedroom, 1.5-bath home features a spacious living area and sizable bedrooms. The third bedroom is accessible from the primary bedroom and the exterior entrance, offering flexible use as a den, workout room, or office. The fully fenced yard includes a fire-pit and sits on a corner lot, with a shed for storage. Ready to move in, the home has no carpet and recent updates include new

    Cathleen Gedeon CENTURY 21 Advantage Realty

    52 Judy Ann Ct, Winchester, KY 40391
  • /3

    $94,000 Sold Aug 22, 2025

    2010 Athens Boonesboro Rd, Winchester, KY 40391

    • Land
    • 4.02 Acres
    • $23,383 per Acre

    Last Sold Summary

    • 14% Below List Price
    • 140 Days On Market

    Current Estimated Value $175,774

    Last Listing Agent Megan McCoy Keller Williams Legacy Group

    2010 Athens Boonesboro Rd, Winchester, KY 40391
    • /23

      Est $244,562 Not Listed For Sale

      130 Hilltop Dr, Winchester, KY 40391

      • 3 Beds
      • 1 Bath
      • 1,465 Sq Ft
      • Built 1960
      130 Hilltop Dr, Winchester, KY 40391

      Last Sold Summary

      • 19% Above List Price
      • $140/SF
      • 2 Days On Market

      Last Sold Price $205,000

      Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  • /3

    $1,200 Pending

    • Land
    • 2.57 Acres
    • $467 per Acre

    507 Tech Dr, Winchester, KY 40391

    For lease-Frontage on Rolling Hills Rd, and Tech Drive.I-64 visibility, ideally located commercial property. Paved driveway and gravel lot.$1200 per .25 acre/per month

    Holly Spradlin KY Realty Co

    507 Tech Dr, Winchester, KY 40391
  • /21

    $199,500 Sold May 09, 2025

    445 Colby Ridge Blvd, Winchester, KY 40391

    • 3 Beds
    • 2.5 Baths
    • 1,539 Sq Ft
    • Built 1998

    Last Sold Summary

    • $130/SF
    • 3 Days On Market

    Current Estimated Value $209,854

    Last Listing Agent Mary Layton FC Tucker Bluegrass

    445 Colby Ridge Blvd, Winchester, KY 40391
    • /54

      Est $391,182 Not Listed For Sale

      1455 Irvine Rd, Winchester, KY 40391

      • 4 Beds
      • 3 Baths
      • 2,901 Sq Ft
      • Built 1940
      1455 Irvine Rd, Winchester, KY 40391

      Last Sold Summary

      • 9% Above List Price
      • $124/SF
      • 35 Days On Market

      Last Sold Price $360,000

      Last Listing Agent Shari Frasure Keller Williams Commonwealth

  • /27

    $269,000 Pending

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

    222 Bracken Ct, Winchester, KY 40391

    Great flloor plan -- great location -- GREAT price! Nice open space on the first level with fully-equipped kitchen and dining area and a very generously-sized family room. Backs up to Ecton Road so you are not looking at the back of another house. Primary bedroom and laundry upstairs with two other bedrooms. All three bedrooms have walk-in closets! The storage building conveys. This home is less

    Jim Woodrum RE/MAX Creative, Winchester

    222 Bracken Ct, Winchester, KY 40391
  • /79

    $849,900 Sold May 23, 2025

    3714 Wades Mill Rd, Winchester, KY 40391

    • 5 Beds
    • 3.5 Baths
    • 3,818 Sq Ft
    • Built 2001

    Last Sold Summary

    • $223/SF
    • 55 Days On Market

    Current Estimated Value $899,392

    Last Listing Agent Nora Williams Keller Williams Commonwealth

    3714 Wades Mill Rd, Winchester, KY 40391
    • /70

      Est $269,683 Not Listed For Sale

      1131 Ironworks Rd, Winchester, KY 40391

      • 3 Beds
      • 2 Baths
      • 2,321 Sq Ft
      • Built 1960
      1131 Ironworks Rd, Winchester, KY 40391

      Last Sold Summary

      • 2% Above List Price
      • $114/SF
      • 45 Days On Market

      Last Sold Price $265,000

      Last Listing Agent Christa Joynt Keller Williams Commonwealth

  • /47

    $235,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,346 Sq Ft

    23 Kittison Dr, Winchester, KY 40391

    24 HOUR KICKOUT! ONE-OWNER BRICK RANCH HOME!! Now that I have your attention, schedule a showing quickly, this one won't last long!! This cozy home has 3 spacious bedrooms, 2 bath, and a family room and kitchen area that are wonderful for family gatherings. You will love the beautiful hardwood floors throughout the home. Don't forget the garage /workshop area out back with room to grow if needed.

    Teresa Richmond Freedom Realty & Property Management

    23 Kittison Dr, Winchester, KY 40391
  • /51

    $560,000 Sold Jun 10, 2025

    520 Gay Evans Rd, Winchester, KY 40391

    • 3 Beds
    • 4 Baths
    • 3,160 Sq Ft
    • Built 2012

    Last Sold Summary

    • 3% Below List Price
    • $177/SF
    • 11 Days On Market

    Current Estimated Value $566,354

    Last Listing Agent Robin Jones Keller Williams Legacy Group

    520 Gay Evans Rd, Winchester, KY 40391
    • /26

      Est $247,287 Not Listed For Sale

      1124 Ironworks Rd, Winchester, KY 40391

      • 3 Beds
      • 2 Baths
      • 1,176 Sq Ft
      • Built 2006
      1124 Ironworks Rd, Winchester, KY 40391

      Last Sold Summary

      • 12% Above List Price
      • $187/SF
      • 7 Days On Market

      Last Sold Price $219,900

      Last Listing Agent Kathryn Cheuvront Coldwell Banker McMahan

  • /31

    $155,000 Pending

    • 3 Beds
    • 1 Bath
    • 1,160 Sq Ft

    730 Byrd Ave, Winchester, KY 40391

    Full of opportunity on a large lot! With mostly cosmetic updates needed, this is an ideal project for a flip or a rental refresh. The layout and lot size provide flexibility, and this property has excellent potential to add value quickly. Being sold as-is.

    Patricia Weiderman Kentucky Land and Home

    730 Byrd Ave, Winchester, KY 40391
  • /17

    $30,000 Sold Jun 30, 2025

    12591 Ironworks Rd, Winchester, KY 40391

    • Land
    • 1.72 Acres
    • $17,442 per Acre

    Last Sold Summary

    • 14% Below List Price
    • 51 Days On Market

    Current Estimated Value $132,227

    Last Listing Agent Cathleen Gedeon CENTURY 21 Advantage Realty

    12591 Ironworks Rd, Winchester, KY 40391
    • /28

      Est $238,068 Not Listed For Sale

      1112 Ironworks Rd, Winchester, KY 40391

      • 3 Beds
      • 2 Baths
      • 1,176 Sq Ft
      • Built 2006
      1112 Ironworks Rd, Winchester, KY 40391

      Last Sold Summary

      • 8% Above List Price
      • $187/SF
      • 116 Days On Market

      Last Sold Price $220,000

      Last Listing Agent Michelle Blackburn RE/MAX

  • /33

    $210,000

    • 4 Beds
    • 1 Bath
    • 1,743 Sq Ft

    218 E Washington St, Winchester, KY 40391

    Motivated seller! Bring your offers. This home is a charming 4 bedroom 1 bath. It boasts a large bonus room which could be an office or 5th bedroom. This home offers a nice sized laundry room with space to add a second bathroom. This home has a nicely shaded fully fenced in back yard with a gate for easy accessibility . There is also a detached storage garage and a long driveway. Within walking

    Fernando Andrade Rector Hayden Realtors

    218 E Washington St, Winchester, KY 40391
  • /34

    $260,000 Sold Apr 17, 2025

    597 Marseille Blvd, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 1,565 Sq Ft
    • Built 1993

    Last Sold Summary

    • 5% Below List Price
    • $166/SF
    • 63 Days On Market

    Current Estimated Value $283,290

    Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

    597 Marseille Blvd, Winchester, KY 40391
    • /41

      Est $230,927 Not Listed For Sale

      273 Winn Ave, Winchester, KY 40391

      • 3 Beds
      • 1 Bath
      • 1,982 Sq Ft
      • Built 1880
      273 Winn Ave, Winchester, KY 40391

      Last Sold Summary

      • 7% Above List Price
      • $108/SF
      • 38 Days On Market

      Last Sold Price $215,000

      Last Listing Agent Nena Honaker Tom Goebel & Company

  • /2

    $100,000

    • Land
    • 0.32 Acre
    • $312,500 per Acre

    111 Jacob 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

    111 Jacob Ct, Winchester, KY 40391
  • /46

    $282,900 Sold Jan 02, 2026

    165 Hilltop Dr, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 1,454 Sq Ft
    • Built 2020

    Last Sold Summary

    • 1% Below List Price
    • $195/SF
    • 6 Days On Market

    Current Estimated Value $280,883

    Last Listing Agent Tyson Walters Kassie & Associates

    165 Hilltop Dr, Winchester, KY 40391
    • /38

      Est $236,888 Not Listed For Sale

      113 Mary Way, Winchester, KY 40391

      • 3 Beds
      • 2 Baths
      • 1,050 Sq Ft
      • Built 1996
      113 Mary Way, Winchester, KY 40391

      Last Sold Summary

      • 5% Above List Price
      • $214/SF
      • 10 Days On Market

      Last Sold Price $225,000

      Last Listing Agent Ashley Spencer Keller Williams Commonwealth

  • /3

    $42,500

    • Land
    • 0.2 Acre
    • $212,500 per Acre

    108 Dorset Ln, Winchester, KY 40391

    The restictions state that if it is a ranch plan, there is a minimun of 1300 sq ft. It it is a 1 1/2 story or two story then 1800 sq ft will be required. A two car garage must be attached. Developer will need to approve plans before starting construction This lot is ideal for a walkout basement. Perfect setting for watching the sunsets

    Jo Gawthrop Keller Williams Bluegrass Realty

    108 Dorset Ln, Winchester, KY 40391
  • /62

    $384,000 Sold Apr 10, 2025

    890 Miller Hunt Rd, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 1,425 Sq Ft
    • Built 1965

    Last Sold Summary

    • $269/SF
    • 5 Days On Market

    Current Estimated Value $400,241

    Last Listing Agent Daniel Mullins ERA Select Real Estate

    890 Miller Hunt Rd, Winchester, KY 40391
    • /30

      Est $217,076 Not Listed For Sale

      306 Sarah Ct, Winchester, KY 40391

      • 3 Beds
      • 2 Baths
      • 1,092 Sq Ft
      • Built 1998
      306 Sarah Ct, Winchester, KY 40391

      Last Sold Summary

      • 12% Above List Price
      • $177/SF
      • 0 Days On Market

      Last Sold Price $193,000

      Last Listing Agent Jennifer Rose United Real Estate Bluegrass

  • /7

    $270,000

    • Land
    • 0.84 Acre
    • $321,429 per Acre

    800 Interstate Dr, Winchester, KY 40391

    Visibility, Access, Utilities on site per seller/per plat buyer to verify, zoned B-3. .84 acres located and visible at I-64 exit 96, buyer to verify and satisfy themselves to all aspects and information on property and or inspections sold as is. Buyer to verify water, gas, and electric locations and availability.

    Whitney Ensor Ensor Real Estate, LLC

    800 Interstate Dr, Winchester, KY 40391
  • /41

    $650,000 Sold Jun 23, 2025

    357 Wades Mill Rd, Winchester, KY 40391

    • 4 Beds
    • 3.5 Baths
    • 3,007 Sq Ft
    • Built 2002

    Last Sold Summary

    • 6% Below List Price
    • $216/SF
    • 15 Days On Market

    Current Estimated Value $668,993

    Last Listing Agent Emily Belcher Rector Hayden Realtors

    357 Wades Mill Rd, Winchester, KY 40391
    • /29

      Est $278,135 Not Listed For Sale

      455 Greenway Dr, Winchester, KY 40391

      • 3 Beds
      • 2 Baths
      • 1,584 Sq Ft
      • Built 1993
      455 Greenway Dr, Winchester, KY 40391

      Last Sold Summary

      • 17% Above List Price
      • $150/SF
      • 0 Days On Market

      Last Sold Price $238,000

      Last Listing Agent Heather Isaacs Lifstyl Real Estate

  • /86

    $530,000 Pending

    • 4 Beds
    • 3.5 Baths
    • 3,848 Sq Ft

    125 Casa Landa Way, Winchester, KY 40391

    Stoney Brook Subdivision! Second time ever offered for sale. Beautiful two story brick home with first and second floor en-suites. Each of the 4 bedrooms has its own walk in closet. Formal family room and dinning rooms, great room with fireplace, breakfast area, all season room with natural lighting, and large flex space located on second floor. All of this setting on .40 of an acre lot with side

    Maggie Napier Napier Realtors

    125 Casa Landa Way, Winchester, KY 40391
  • /23

    $210,000 Sold May 12, 2025

    202 Washington Square, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1998

    Last Sold Summary

    • 11% Above List Price
    • $175/SF
    • 1 Day On Market

    Current Estimated Value $210,916

    Last Listing Agent Aaron Kendall Lifstyl Real Estate

    202 Washington Square, Winchester, KY 40391
    • /25

      Est $234,957 Not Listed For Sale

      316 Jameson Way, Winchester, KY 40391

      • 3 Beds
      • 2 Baths
      • 1,625 Sq Ft
      • Built 1990
      316 Jameson Way, Winchester, KY 40391

      Last Sold Summary

      • 4% Above List Price
      • $138/SF
      • 140 Days On Market

      Last Sold Price $225,000

      Last Listing Agent Jenny Bradley Rector Hayden Realtors

  • /27

    $269,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft

    916 Stratton Ln, Winchester, KY 40391

    Welcome to 916 Stratton Lane, a beautifully updated 3 bedroom, 2 bath home offering 1,400 square feet of comfortable living space in the highly desired Westmeade area. This charming brick home features a warm and inviting interior with stylish updates throughout. The spacious living room showcases rich dark flooring, a stunning stone fireplace, and abundant natural light, creating the perfect

    Joshua Davis The Agency

    916 Stratton Ln, Winchester, KY 40391
  • /44

    $206,500 Sold May 21, 2025

    206 W Clark Dr, Winchester, KY 40391

    • 3 Beds
    • 1 Bath
    • 1,107 Sq Ft
    • Built 1962

    Last Sold Summary

    • 6% Below List Price
    • $187/SF
    • 23 Days On Market

    Current Estimated Value $212,820

    Last Listing Agent Peggy Baldridge HomeFirst Real Estate

    206 W Clark Dr, Winchester, KY 40391
    • /38

      Est $202,044 Not Listed For Sale

      412 Jameson Way, Winchester, KY 40391

      • 3 Beds
      • 1 Bath
      • 1,073 Sq Ft
      • Built 1990
      412 Jameson Way, Winchester, KY 40391

      Last Sold Summary

      • 23% Above List Price
      • $153/SF
      • 0 Days On Market

      Last Sold Price $163,900

      Last Listing Agent Josh Wood Freedom Realty & Property Management

  • /39

    $579,900

    • 4 Beds
    • 5 Baths
    • 4,374 Sq Ft

    600 Boone Ave, Winchester, KY 40391

    Step into the timeless elegance of this stunning Southern antebellum-style home, where classic charm meets modern luxury. Boasting four spacious bedrooms and five beautifully appointed bathrooms, this grand residence offers an unparalleled level of sophistication and comfort. A breathtaking foyer and entryway welcome you with a sweeping staircase, and exquisite architectural details, setting the

    Holly Goeing The Agency

    600 Boone Ave, Winchester, KY 40391
  • /26

    $250,000 Sold Feb 20, 2026

    21 Virginia Ave, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 1,749 Sq Ft
    • Built 1962

    Last Sold Summary

    • 4% Below List Price
    • $143/SF
    • 40 Days On Market

    Current Estimated Value $252,766

    Last Listing Agent Emily Crump EXP Realty, LLC

    21 Virginia Ave, Winchester, KY 40391
    • /14

      Est $176,427 Not Listed For Sale

      411 Jameson Way, Winchester, KY 40391

      • 3 Beds
      • 1 Bath
      • 1,000 Sq Ft
      • Built 1990
      411 Jameson Way, Winchester, KY 40391

      Last Sold Summary

      • 14% Above List Price
      • $155/SF
      • 19 Days On Market

      Last Sold Price $155,000

      Last Listing Agent Jason Szaks EXIT TOWN & COUNTRY REALTORS

  • /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
  • /19

    $199,900 Sold Feb 12, 2026

    117 Buffalo Trace, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 1,072 Sq Ft
    • Built 1998

    Last Sold Summary

    • $186/SF
    • 49 Days On Market

    Current Estimated Value $198,126

    Last Listing Agent Nena Honaker Tom Goebel & Company

    117 Buffalo Trace, Winchester, KY 40391
    • /33

      Est $298,935 Not Listed For Sale

      137 Summerhill Way, Winchester, KY 40391

      • 3 Beds
      • 2 Baths
      • 1,284 Sq Ft
      • Built 2003
      137 Summerhill Way, Winchester, KY 40391

      Last Sold Summary

      • 11% Above List Price
      • $210/SF
      • 6 Days On Market

      Last Sold Price $270,000

      Last Listing Agent Keith Wilson Coldwell Banker McMahan

Showing Results 321 - 360, Page 9 of 18

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