Winchester, KY Homes

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  /23

  Est $260,171 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

  • 27% 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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  /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
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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 $279,602

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

  597 Marseille Blvd, Winchester, KY 40391
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  /54

  Est $411,273 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

  • 14% Above List Price
  • $124/SF
  • 35 Days On Market

  Last Sold Price $360,000

  Last Listing Agent Shari Frasure Keller Williams Commonwealth
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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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  /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 $276,187

  Last Listing Agent Tyson Walters Kassie & Associates

  165 Hilltop Dr, Winchester, KY 40391
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  /70

  Est $258,473 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% Below 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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  /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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  /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 $386,578

  Last Listing Agent Daniel Mullins ERA Select Real Estate

  890 Miller Hunt Rd, Winchester, KY 40391
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  /26

  Est $223,924 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

  • 2% Above List Price
  • $187/SF
  • 7 Days On Market

  Last Sold Price $219,900

  Last Listing Agent Kathryn Cheuvront Coldwell Banker McMahan
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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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  /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 $675,543

  Last Listing Agent Emily Belcher Rector Hayden Realtors

  357 Wades Mill Rd, Winchester, KY 40391
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  /28

  Est $216,119 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

  • 2% Below List Price
  • $187/SF
  • 116 Days On Market

  Last Sold Price $220,000

  Last Listing Agent Michelle Blackburn RE/MAX
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  /35

  $244,900 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,641 Sq Ft

  426 Paisley Ct, Winchester, KY 40391

  Beautiful well designed townhouse built with quality and craftsmanship in mind situated on desirable cul-de-sac. Home offers 3 bedrooms, 2.5 baths with 2-car attached garage. You are greeted with gleaming hardwood flooring and crown molding. The thoughtfully designed kitchen with full complement of appliances overlooks dining area and vaulted great room that opens to a screened-in porch with

  Lura Justice Rector Hayden Realtors

  426 Paisley Ct, Winchester, KY 40391
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  /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 $209,587

  Last Listing Agent Aaron Kendall Lifstyl Real Estate

  202 Washington Square, Winchester, KY 40391
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  /41

  Est $231,042 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
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  /47

  $452,500

  • 3 Beds
  • 2.5 Baths
  • 2,961 Sq Ft

  42 Mockingbird Valley Rd, Winchester, KY 40391

  This is a perfect home for EVERY season.....enjoy multiple, interior gathering spaces and the glow and warmth of either the L R or Dining Room fireplace on the main level or the coziness of the mesmerizing fireplace in the lower level family room during the winter. Watch the backyard come alive with rich and lush vegetation during the Spring from the large, glass walled sun room. For Summer, tons

  Markus Cross McCallie Real Estate

  42 Mockingbird Valley Rd, Winchester, KY 40391
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  /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 $213,854

  Last Listing Agent Peggy Baldridge HomeFirst Real Estate

  206 W Clark Dr, Winchester, KY 40391
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  /38

  Est $225,558 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

  • $214/SF
  • 10 Days On Market

  Last Sold Price $225,000

  Last Listing Agent Ashley Spencer Keller Williams Commonwealth
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  /2

  $100,000

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

  169 Duclair Dr, 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

  169 Duclair Dr, Winchester, KY 40391
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  /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 $198,037

  Last Listing Agent Nena Honaker Tom Goebel & Company

  117 Buffalo Trace, Winchester, KY 40391
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  /30

  Est $218,115 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

  • 13% 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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  /22

  $221,500

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

  443 Jameson Way, Winchester, KY 40391

  This move in ready ranch home offering 4 bedrooms and 2 full bathrooms is ready for a new owner. This home is in an income restricted community, 80% of LIHTC for Clark County. Property offers brand new cabinets, countertops, appliances, flooring, fresh painting and more. Contact listing agent to receive the income limits for buyers to qualify to purchase property. Set up your showing today!

  Tyler I Back The Brokerage

  443 Jameson Way, Winchester, KY 40391
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  /2

  $165,000 Sold May 30, 2025

  Unlisted Address

  • 3 Beds
  • 1.5 Baths
  • 1,200 Sq Ft
  • Built 1988

  Last Sold Summary

  • $138/SF

  Current Estimated Value $173,069

  Last Listing Agent Null Non-Member Non-Member Office

  Unlisted Address
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  /29

  Est $260,343 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

  • 9% Above List Price
  • $150/SF
  • 0 Days On Market

  Last Sold Price $238,000

  Last Listing Agent Heather Isaacs Lifstyl Real Estate
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  /29

  $234,900

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft

  11 Shelley Dr, Winchester, KY 40391

  SELLER is motivated to offers! Welcoming you to this lovely updated throughout 3 bedroom, 2 full bath ranch! As you step into the home with its cozy feeling, and spacious space in every room, including a full unfinished basement wonderful for storage or to finish that into living square footage, great size back yard with large back patio perfect for the family gatherings, also a partial fenced in

  Nichole Bingham CENTURY 21 Advantage Realty

  11 Shelley Dr, Winchester, KY 40391
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  /44

  $310,000 Sold Jun 27, 2025

  2482 Mina Station Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,756 Sq Ft
  • Built 1962

  Last Sold Summary

  • $177/SF
  • 24 Days On Market

  Current Estimated Value $305,436

  Last Listing Agent Stephanie Hacker Kentucky Residential Real Estate, LLC

  2482 Mina Station Rd, Winchester, KY 40391
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  /25

  Est $232,791 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

  • 3% Above List Price
  • $138/SF
  • 140 Days On Market

  Last Sold Price $225,000

  Last Listing Agent Jenny Bradley Rector Hayden Realtors
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  /27

  $198,000

  • 2 Beds
  • 1 Bath
  • 1,223 Sq Ft

  616 Boone Ave, Winchester, KY 40391

  Begin the New Year in your own home! It's a new beginning...Make an appoint to look at this two bedroom, one bath ranch. It has new paint and updated flooring. Range refrigerator and dishwasher are included, There is a nice size laundry room. The kitchen has lots of cabinets and there is an additional pantry in the hall. The dining room is off the kitchen and overlooks the living room. The rear

  Garnett Davis Tom Goebel & Company

  616 Boone Ave, Winchester, KY 40391
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  /54

  $1,546,482 Sold Apr 02, 2025

  118 Bella Shae Way, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 3,220 Sq Ft
  • Built 2024

  Last Sold Summary

  • 62% Above List Price
  • $480/SF
  • 0 Days On Market

  Current Estimated Value $853,822

  Last Listing Agent Shane Underwood Keller Williams Commonwealth

  118 Bella Shae Way, Winchester, KY 40391
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  /38

  Est $184,281 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

  • 12% Above List Price
  • $153/SF
  • 0 Days On Market

  Last Sold Price $163,900

  Last Listing Agent Josh Wood Freedom Realty & Property Management
• 

  

  /23

  $270,000

  • 4 Beds
  • 2 Baths
  • 1,984 Sq Ft

  108 Ashley Dr, Winchester, KY 40391

  Be among the first to discover this exceptional property! This is a brand new listing, presenting a unique opportunity to own a home in a highly sought-after location. Imagine living in a neighborhood where everything you need is just a stone's throw away. This fabulous property boasts not only a full basement, offering endless possibilities for recreation, storage, or a home office, but also an

  A. Rebecca Woods Woods Realty Group

  108 Ashley Dr, Winchester, KY 40391
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  /12

  $75,000 Sold Jun 17, 2025

  120 Jacob Ct, Winchester, KY 40391

  • Land
  • 0.55 Acre
  • $136,364 per Acre

  Last Sold Summary

  • 32% Below List Price
  • 210 Days On Market

  Current Estimated Value $77,257

  Last Listing Agent Keith Wilson Coldwell Banker McMahan

  120 Jacob Ct, Winchester, KY 40391
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  /14

  Est $171,986 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

  • 11% Above List Price
  • $155/SF
  • 19 Days On Market

  Last Sold Price $155,000

  Last Listing Agent Jason Szaks EXIT TOWN & COUNTRY REALTORS
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  /2

  $100,000

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

  115 Duclair Dr, 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

  115 Duclair Dr, Winchester, KY 40391
• 

  

  /51

  $428,000 Sold Sep 04, 2025

  17 Hampton Ave, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 3,181 Sq Ft
  • Built 1960

  Last Sold Summary

  • 4% Below List Price
  • $135/SF
  • 34 Days On Market

  Current Estimated Value $430,397

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate

  17 Hampton Ave, Winchester, KY 40391
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  /31

  Est $238,025 Not Listed For Sale

  121 Summerhill Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,302 Sq Ft
  • Built 2002

  121 Summerhill Way, Winchester, KY 40391

  Last Sold Summary

  • 22% Above List Price
  • $150/SF
  • 70 Days On Market

  Last Sold Price $195,000

  Last Listing Agent Peter doCouto Plum Tree Realty
• 

  

  /23

  $180,000

  • 2 Beds
  • 1 Bath

  220 Jackson St, Winchester, KY 40391

  Welcome to 3769 Winthrop Drive in Lexington, KY 40514 - a fantastic opportunity to own a home in one of South Lexington's most convenient and sought-after areas. Tucked into an established neighborhood, this property offers the perfect combination of comfort, accessibility, and everyday functionality. Step inside to discover a welcoming layout designed for both relaxing and entertaining. The

  Hunter Miller GSP Homes

  220 Jackson St, Winchester, KY 40391
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  /26

  $239,500 Sold Jul 15, 2025

  129 Bay Hill Dr, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,017 Sq Ft
  • Built 1998

  Last Sold Summary

  • 2% Below List Price
  • $119/SF
  • 26 Days On Market

  Current Estimated Value $243,870

  Last Listing Agent Vickie Skeens RE/MAX Elite Lexington

  129 Bay Hill Dr, Winchester, KY 40391
• 

  

  /23

  Est $249,257 Not Listed For Sale

  302 Salem Ave, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,490 Sq Ft
  • Built 2001

  302 Salem Ave, Winchester, KY 40391

  Last Sold Summary

  • 2% Below List Price
  • $171/SF
  • 34 Days On Market

  Last Sold Price $255,000

  Last Listing Agent Emily Donaldson Keller Williams Commonwealth

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