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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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