Winchester, KY Homes

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  /10

  Est $197,435 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,265 Sq Ft

  24 Fairview Ave, Winchester, KY 40391

  24 Fairview Ave, Winchester, KY 40391
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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
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  /51

  $290,000 Sold Mar 12, 2025

  28 Edgewood Dr, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 1,962 Sq Ft
  • Built 1984

  Last Sold Summary

  • 8% Below List Price
  • $148/SF
  • 11 Days On Market

  Current Estimated Value $314,388

  Last Listing Agent Robin Jones Keller Williams Legacy Group

  28 Edgewood Dr, Winchester, KY 40391
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  /55

  Est $193,917 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,416 Sq Ft

  30 Ashland Ave, Winchester, KY 40391

  30 Ashland Ave, Winchester, KY 40391
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  /86

  $550,000

  • 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
• 

  /2

  $39,500 Sold Mar 05, 2025

  418 Fairholme Way, Winchester, KY 40391

  • Land
  • 0.38 Acre
  • $103,947 per Acre

  Last Sold Summary

  • 14% Above List Price
  • 1,594 Days On Market

  Current Estimated Value $96,141

  Last Listing Agent Garnett Davis Tom Goebel & Company

  418 Fairholme Way, Winchester, KY 40391
• 

  

  /30

  Est $165,758 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,126 Sq Ft

  370 E Washington St, Winchester, KY 40391

  370 E Washington St, Winchester, KY 40391
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  /65

  $609,900 Pending

  • 5 Beds
  • 4 Baths
  • 4,515 Sq Ft

  6595 Mount Sterling Rd, Winchester, KY 40391

  INCREDIBLE! This custom-built home sits on 2.59 acres in a prime location just minutes from I-64 and perfectly positioned between Winchester and Mount Sterling. The main level features a grand formal dining room, a family room with a vaulted coffered ceiling, and an eat-in kitchen open to the living area for easy entertaining. You'll also find the first primary suite plus two additional bedrooms

  Brooke Otis Mullins RO&CO Real Estate

  6595 Mount Sterling Rd, Winchester, KY 40391
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  /2

  $610,000 Sold Aug 29, 2025

  4560 Pine Ridge Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,848 Sq Ft
  • Built 1905

  Last Sold Summary

  • $330/SF
  • 1 Day On Market

  Current Estimated Value $610,684

  Last Listing Agent Natalie Avant Berkshire Hathaway HomeServices Foster Realtors

  4560 Pine Ridge Rd, Winchester, KY 40391
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  /32

  Est $205,049 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,900 Sq Ft

  203 Crawford Ct, Winchester, KY 40391

  203 Crawford Ct, Winchester, KY 40391
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  /39

  $612,900

  • 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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  /32

  $263,000 Sold Sep 05, 2025

  2 Chickadee Ln, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,397 Sq Ft
  • Built 1960

  Last Sold Summary

  • 1% Above List Price
  • $188/SF
  • 2 Days On Market

  Current Estimated Value $261,967

  Last Listing Agent Ashley Spencer Keller Williams Commonwealth

  2 Chickadee Ln, Winchester, KY 40391
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  /53

  Est $208,456 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,631 Sq Ft

  29 Fairview Ave, Winchester, KY 40391

  29 Fairview Ave, Winchester, KY 40391
• 

  

  /79

  $609,900 Pending

  • 4 Beds
  • 3.5 Baths
  • 4,779 Sq Ft

  180 Casa Landa Way, Winchester, KY 40391

  This stately yet inviting residence in the highly desirable Stoney Brook subdivision offers the perfect blend of elegance and comfort. Thoughtfully designed for everyday living and entertaining, the home features generously sized rooms throughout. The main level includes formal living and dining spaces, a convenient half bath, and a beautifully appointed kitchen with granite countertops,

  Janna Smith United Real Estate Bluegrass

  180 Casa Landa Way, Winchester, KY 40391
• 

  

  /35

  $325,000 Sold Nov 21, 2025

  130 Hibiscus Ln, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 1,900 Sq Ft
  • Built 2000

  Last Sold Summary

  • 7% Below List Price
  • $171/SF
  • 19 Days On Market

  Last Listing Agent Ashley Barreto Indigo & Co

  130 Hibiscus Ln, Winchester, KY 40391
• 

  

  /29

  Est $180,244 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 832 Sq Ft

  4 Sylvania Ave, Winchester, KY 40391

  4 Sylvania Ave, Winchester, KY 40391
• 

  /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
• 

  /2

  $110,750 Sold Feb 07, 2025

  Unlisted Address

  • 2 Beds
  • 2 Baths
  • 906 Sq Ft
  • Built 1995

  Last Sold Summary

  • $122/SF

  Current Estimated Value $151,144

  Last Listing Agent Jo Gawthrop Keller Williams Bluegrass Realty

  Unlisted Address
• 

  

  /22

  Est $188,910 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,016 Sq Ft

  21 Sylvania Ave, Winchester, KY 40391

  21 Sylvania Ave, Winchester, KY 40391
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  /30

  $199,900 Pending

  • 3 Beds
  • 1 Bath
  • 1,354 Sq Ft

  40 Garner St, Winchester, KY 40391

  Check out this lovely all brick, beautifully renovated 3-bedroom,1bath home located in Winchester perfectly blending timeless charm with modern updates. This move-in ready home features a new roof, updated electrical and plumbing, an upgraded kitchen, new flooring, a fully renovated bathroom, fresh paint throughout, and all new appliances. Situated on a spacious corner lot, the property offers

  Nicole Seals Guide Realty, Inc.

  40 Garner St, Winchester, KY 40391
• 

  

  /23

  $244,895 Sold Jun 10, 2025

  244 Bay Hill Ct, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 2,536 Sq Ft
  • Built 2006

  Last Sold Summary

  • 2% Below List Price
  • $97/SF
  • 10 Days On Market

  Current Estimated Value $259,896

  Last Listing Agent Destiny Darby Keller Williams Commonwealth

  244 Bay Hill Ct, Winchester, KY 40391
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  /30

  Est $201,059 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,432 Sq Ft

  280 Winn Ave, Winchester, KY 40391

  280 Winn Ave, Winchester, KY 40391
• 

  

  /19

  $189,500 Pending

  • 2 Beds
  • 2.5 Baths
  • 1,197 Sq Ft

  111 Quail Ridge Rd, Winchester, KY 40391

  Move-In Ready Brick Townhome with Garage and Fireplace Step into this charming brick townhome offering comfort, style, and convenience in every detail. The spacious living room features a cozy fireplace, soft neutral tones, and natural light that make it easy to feel at home. The open layout flows to the kitchen and dining area, creating the perfect setting for everyday living or entertaining

  Kim Dice EXP Realty, LLC

  111 Quail Ridge Rd, Winchester, KY 40391
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  /51

  $340,000 Sold Oct 30, 2025

  356 Boone Ave, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 3,200 Sq Ft
  • Built 1940

  Last Sold Summary

  • 5% Below List Price
  • $106/SF
  • 30 Days On Market

  Last Listing Agent Elizabeth Hodge Lifstyl Real Estate

  356 Boone Ave, Winchester, KY 40391
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  /21

  Est $148,383 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 884 Sq Ft

  48 Watts Rd, Winchester, KY 40391

  48 Watts Rd, Winchester, KY 40391
• 

  /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
• 

  /2

  $110,750 Sold Feb 07, 2025

  Unlisted Address

  • 2 Beds
  • 1.5 Baths
  • 1,008 Sq Ft
  • Built 1979

  Last Sold Summary

  • $110/SF

  Current Estimated Value $161,523

  Last Listing Agent Jo Gawthrop Keller Williams Bluegrass Realty

  Unlisted Address
• 

  

  /25

  Est $133,067 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,465 Sq Ft

  248 Cook Ave, Winchester, KY 40391

  248 Cook Ave, Winchester, KY 40391
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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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  /3

  $40,000 Sold Feb 11, 2025

  Unlisted Address

  • Land
  • 0.19 Acre
  • $210,526 per Acre

  Last Sold Summary

  Current Estimated Value $362,344

  Last Listing Agent Jo Gawthrop Keller Williams Bluegrass Realty

  Unlisted Address
• 

  

  /4

  Est $72,809 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 940 Sq Ft

  Unlisted Address

  Unlisted Address
• 

  

  /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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  /2

  $110,750 Sold Feb 07, 2025

  Unlisted Address

  • 2 Beds
  • 2 Baths
  • 906 Sq Ft
  • Built 1995

  Last Sold Summary

  • $122/SF

  Current Estimated Value $152,320

  Last Listing Agent Jo Gawthrop Keller Williams Bluegrass Realty

  Unlisted Address
• 

  

  /41

  Est $216,431 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,343 Sq Ft

  31 Watts Rd, Winchester, KY 40391

  31 Watts Rd, Winchester, KY 40391
• 

  

  /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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  /4

  $315,000 Sold Jun 30, 2025

  4550 Schollsville Rd Unit 40391, Winchester, KY 40391

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Mila Ensor Ensor Real Estate, LLC

  4550 Schollsville Rd Unit 40391, Winchester, KY 40391
• 

  

  /27

  Est $311,601 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,780 Sq Ft

  198 Hilltop Dr, Winchester, KY 40391

  198 Hilltop Dr, Winchester, KY 40391
• 

  

  /28

  $309,900 Open Sun 1PM - 4PM

  • 3 Beds
  • 3.5 Baths
  • 2,526 Sq Ft

  24 N Burns Ave, Winchester, KY 40391

  Historic charm with all the modern amenities! An inviting front porch and entry lead to a welcoming space warmed by refinished original hardwood floors and a new electric fireplace. Other updates include a brand-new kitchen with granite countertops and new appliances, new lighting fixtures, tile in the foyer and bathrooms, new roof, new plumbing, new electrical, new HVAC, new windows, new spray

  Sarah Hess Keller Williams Commonwealth

  24 N Burns Ave, Winchester, KY 40391
• 

  /2

  $175,000 Sold Jan 30, 2025

  27 N Burns Ave, Winchester, KY 40391

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

  Last Sold Summary

  • 1% Below List Price
  • $73/SF
  • 0 Days On Market

  Current Estimated Value $204,425

  Last Listing Agent Kim Caywood The Real Estate Co.

  27 N Burns Ave, Winchester, KY 40391
• 

  

  /23

  Est $268,002 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,465 Sq Ft

  130 Hilltop Dr, Winchester, KY 40391

  130 Hilltop Dr, Winchester, KY 40391

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