Winchester, KY Homes

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  /79

  $204,000 Sold Oct 30, 2025

  133 S Burns Ave, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 3,295 Sq Ft
  • Built 1915

  Last Sold Summary

  • 18% Below List Price
  • $62/SF
  • 20 Days On Market

  Current Estimated Value $215,958

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  133 S Burns Ave, Winchester, KY 40391
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  /18

  Est $201,651 Not Listed For Sale

  6 Western Ave, Winchester, KY 40391

  • 2 Beds
  • 2 Baths
  • 2,109 Sq Ft
  • Built 1950

  6 Western Ave, Winchester, KY 40391

  Last Sold Summary

  • 49% Above List Price
  • $64/SF
  • 46 Days On Market

  Last Sold Price $135,000

  Last Listing Agent Steven G King CENTURY 21 Advantage Realty
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  /47

  $229,000

  • 3 Beds
  • 1.5 Baths
  • 1,636 Sq Ft

  334 S Burns Ave, Winchester, KY 40391

  Great opportunity to own this well loved home in a very convenient location in growing community of Winchester. Lots of character and charm upon entry into the entry foyer with nice staircase, opening to large living room with a lovely mantel. Spacious dining room with built in corner cabinet flows into kitchen with plenty of cabinetry and counter space. Large laundry room with access to rear

  Jeanne Beaven Rector Hayden Realtors

  334 S Burns Ave, Winchester, KY 40391
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  /28

  $246,000 Sold Nov 06, 2025

  204 Moss Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,430 Sq Ft
  • Built 1998

  Last Sold Summary

  • 3% Above List Price
  • $172/SF
  • 1 Day On Market

  Current Estimated Value $245,330

  Last Listing Agent Brooke Martin RO&CO Real Estate

  204 Moss Ct, Winchester, KY 40391
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  /37

  Est $297,873 Not Listed For Sale

  120 Milwood Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,853 Sq Ft
  • Built 1965

  120 Milwood Dr, Winchester, KY 40391

  Last Sold Summary

  • 30% Above List Price
  • $124/SF
  • 80 Days On Market

  Last Sold Price $230,000

  Last Listing Agent Michelle Blackburn RE/MAX
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  /2

  $189,900 Pending

  • Land
  • 10.73 Acres
  • $17,698 per Acre

  1045 Gay Evans Rd, Winchester, KY 40391

  Welcome to The Retreat at Juett Farms! Come build your dream home on some of the best land that Clark County has to offer. This peaceful setting with unparalleled views of the countryside, is sure to impress. Imagine sitting on your front porch taking in the most amazing sunsets! This beautiful parcel has over 10 acres of unrestricted land with many building sites. Schedule your showing today!

  Holly Goeing The Agency

  1045 Gay Evans Rd, Winchester, KY 40391
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  /58

  $232,500 Sold Jul 12, 2025

  114 Holiday Rd, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,161 Sq Ft
  • Built 1980

  Last Sold Summary

  • 7% Below List Price
  • $200/SF
  • 235 Days On Market

  Current Estimated Value $221,093

  Last Listing Agent Karen Smith Emmerich Muzic Realty

  114 Holiday Rd, Winchester, KY 40391
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  /48

  Est $266,859 Not Listed For Sale

  132 Boone Ave, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,496 Sq Ft
  • Built 1930

  132 Boone Ave, Winchester, KY 40391

  Last Sold Summary

  • 72% Above List Price
  • $62/SF
  • 0 Days On Market

  Last Sold Price $155,000

  Last Listing Agent Jacob Jones Apex Realty Consultants
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  /2

  $100,000

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

  129 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

  129 Duclair Dr, Winchester, KY 40391
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  /28

  $234,500 Sold Jul 29, 2025

  108 Sturbridge Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 2004

  Last Sold Summary

  • 4% Below List Price
  • $195/SF
  • 45 Days On Market

  Current Estimated Value $241,143

  Last Listing Agent Jason Szaks EXIT TOWN & COUNTRY REALTORS

  108 Sturbridge Ln, Winchester, KY 40391
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  /39

  Est $353,256 Not Listed For Sale

  14 Euclid Ave, Winchester, KY 40391

  • 5 Beds
  • 3 Baths
  • 3,660 Sq Ft
  • Built 1940

  14 Euclid Ave, Winchester, KY 40391

  Last Sold Summary

  • 17% Above List Price
  • $83/SF
  • 35 Days On Market

  Last Sold Price $303,000

  Last Listing Agent Nicole Seals Guide Realty, Inc.
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  /56

  $425,000

  • 5 Beds
  • 3 Baths
  • 3,718 Sq Ft

  1503 Schollsville Rd, Winchester, KY 40391

  Do you ever wonder what it would be like to live in the days of "Gone with the Wind"? Well, here is your chance to own your own personal "Tara". Spacious country home with acreage suitable for children, pets, and livestock. This home is perfect for escaping city life and crowds. Home consists of 5 bedrooms, 3 full bathrooms, Living Room, Dining Room, large Kitchen, room for an office or craft

  Keith Wilson Coldwell Banker McMahan

  1503 Schollsville Rd, Winchester, KY 40391
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  /52

  $230,000 Sold Jan 20, 2026

  19 Cherokee Ct, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,134 Sq Ft
  • Built 1968

  Last Sold Summary

  • 2% Above List Price
  • $203/SF
  • 2 Days On Market

  Current Estimated Value $227,218

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  19 Cherokee Ct, Winchester, KY 40391
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  /32

  Est $263,015 Not Listed For Sale

  13 Euclid Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,893 Sq Ft
  • Built 1917

  13 Euclid Ave, Winchester, KY 40391

  Last Sold Summary

  • 20% Above List Price
  • $116/SF
  • 75 Days On Market

  Last Sold Price $219,000

  Last Listing Agent Jim Woodrum RE/MAX
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  /23

  $230,000

  • 3 Beds
  • 2 Baths
  • 1,518 Sq Ft

  313 S Burns Ave, Winchester, KY 40391

  This 3 bedroom, 2 bath home sits on a corner lot with hardwood floors and a two-car detached garage behind the home. Plus, it's walkable to downtown Winchester, the public library, and College Park. Inside, you'll find tall ceilings, a traditional living and dining room, and a unique layout that gives you options for how you use the space. The kitchen opens to the back deck, and a ramp at the

  Michelle Blackburn RE/MAX Creative, Winchester

  313 S Burns Ave, Winchester, KY 40391
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  /22

  $334,327 Sold Jul 01, 2025

  136 Gibson Way, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 1,997 Sq Ft
  • Built 2024

  Last Sold Summary

  • $167/SF
  • 219 Days On Market

  Current Estimated Value $343,277

  Last Listing Agent Neshia Gaines Christies International Real Estate Bluegrass

  136 Gibson Way, Winchester, KY 40391
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  /43

  Est $329,301 Not Listed For Sale

  201 Boone Ave, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,513 Sq Ft
  • Built 1909

  201 Boone Ave, Winchester, KY 40391

  Last Sold Summary

  • 8% Above List Price
  • $121/SF
  • 50 Days On Market

  Last Sold Price $304,500

  Last Listing Agent Matt Metts LexHomes Real Estate
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  /5

  $70,000

  • Land
  • 1.72 Acres
  • $40,698 per Acre

  12541 Ironworks Rd, Winchester, KY 40391

  Discover the perfect place to build your dream home in Eskippakithiki Overlooks. This beautiful 1.72 acre parcel offers ample space, peaceful surroundings, and stunning natural views. Enjoy the serenity of country living, this land provides an ideal canvas for a custom home or family getaway. Don't miss this opportunity to secure your own piece of paradise.

  Daniela Virguez National Real Estate

  12541 Ironworks Rd, Winchester, KY 40391
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  /6

  $50,000 Sold Mar 17, 2025

  221 Ashton Oak Way, Winchester, KY 40391

  • Land
  • 0.39 Acre
  • $128,205 per Acre

  Last Sold Summary

  • 9% Below List Price
  • 264 Days On Market

  Current Estimated Value $63,720

  Last Listing Agent Melia Hord Keller Williams Legacy Group

  221 Ashton Oak Way, Winchester, KY 40391
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  /45

  Est $404,654 Not Listed For Sale

  142 College St, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 3,012 Sq Ft
  • Built 1940

  142 College St, Winchester, KY 40391

  Last Sold Summary

  • 4% Below List Price
  • $139/SF
  • 87 Days On Market

  Last Sold Price $420,000

  Last Listing Agent Patrick Arvin Keller Williams Commonwealth
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  /2

  $78,500

  • Land
  • 0.22 Acre
  • $356,818 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

  Melia Hord Keller Williams Legacy Group

  Lot 4 Plantations Dr, Winchester, KY 40391
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  /37

  $275,000 Sold Sep 10, 2025

  279 Ascot Ave, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,247 Sq Ft
  • Built 2000

  Last Sold Summary

  • 8% Below List Price
  • $122/SF
  • 2 Days On Market

  Current Estimated Value $290,091

  Last Listing Agent Chase Pennington Team Pannell Real Estate

  279 Ascot Ave, Winchester, KY 40391
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  /32

  Est $211,719 Not Listed For Sale

  8 Nunnelly Ct, Winchester, KY 40391

  • 2 Beds
  • 1.5 Baths
  • 1,255 Sq Ft
  • Built 1940

  8 Nunnelly Ct, Winchester, KY 40391

  Last Sold Summary

  • 7% Above List Price
  • $157/SF
  • 33 Days On Market

  Last Sold Price $197,000

  Last Listing Agent Timothy Saylor Threshold Real Estate Services
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  /26

  $246,400

  • 5 Beds
  • 3 Baths
  • 3,007 Sq Ft

  221 S Highland St, Winchester, KY 40391

  INVESTOR SPECIAL, You have the opportunity to purchase a fully occupied tri-plex in the heart of Winchester with instant cash flow. Main level unit is a large 2 bed, one bath. Upstairs unit is also a 2 bed, one bath, and lower level is a 1 bed, one bath unit. There is street parking and alley access with parking in the rear. All units have their own exterior entrance. Some utilities are metered

  Joshua Lynch The Brokerage

  221 S Highland St, Winchester, KY 40391
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  /24

  $198,000 Sold Jul 18, 2025

  113 Colonial Park Dr, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,075 Sq Ft
  • Built 1983

  Last Sold Summary

  • 2% Above List Price
  • $184/SF
  • 0 Days On Market

  Current Estimated Value $206,752

  Last Listing Agent Janet Baldwin Kentucky Land and Home

  113 Colonial Park Dr, Winchester, KY 40391
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  /47

  Est $309,764 Not Listed For Sale

  113 S Burns Ave, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 3,299 Sq Ft
  • Built 1895

  113 S Burns Ave, Winchester, KY 40391

  Last Sold Summary

  • 6% Below List Price
  • $100/SF
  • 1 Day On Market

  Last Sold Price $329,900

  Last Listing Agent Ginger Mccoy Kentucky Residential Real Estate, LLC
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  /33

  $429,900

  • 3 Beds
  • 2.5 Baths
  • 2,652 Sq Ft

  107 Woodduck Ct, Winchester, KY 40391

  Located in the Mallard Place subdivision, this ranch home offers 3 bedrooms, 2 full baths, and 1 half bath with approximately 2,652 square feet of finished living space. The home features new flooring in the main living area and a functional single-level layout. The kitchen includes an eat-in area, breakfast bar, double oven, cooktop, microwave, dishwasher, and refrigerator, with laundry

  Laura Eaves Berkshire Hathaway de Movellan Properties

  107 Woodduck Ct, Winchester, KY 40391
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  /27

  $335,000 Sold Dec 18, 2025

  2198 Goshen Rd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,730 Sq Ft
  • Built 1997

  Last Sold Summary

  • 5% Above List Price
  • $194/SF
  • 31 Days On Market

  Current Estimated Value $322,430

  Last Listing Agent Jason Szaks EXIT TOWN & COUNTRY REALTORS

  2198 Goshen Rd, Winchester, KY 40391
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  /35

  Est $316,249 Not Listed For Sale

  123 W Hickman St, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,498 Sq Ft
  • Built 1940

  123 W Hickman St, Winchester, KY 40391

  Last Sold Summary

  • 4% Above List Price
  • $122/SF
  • 1 Day On Market

  Last Sold Price $305,000

  Last Listing Agent Lukas Owens The Brokerage
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  /2

  $100,000

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

  165 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

  165 Duclair Dr, Winchester, KY 40391
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  /28

  $370,000 Sold Sep 03, 2025

  220 Spring Valley Dr, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 3,078 Sq Ft
  • Built 1975

  Last Sold Summary

  • 7% Below List Price
  • $120/SF
  • 3 Days On Market

  Current Estimated Value $386,447

  Last Listing Agent Tracey Goebel Tom Goebel & Company

  220 Spring Valley Dr, Winchester, KY 40391
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  /49

  Est $260,943 Not Listed For Sale

  115 Olde Potomac Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 2,018 Sq Ft
  • Built 1940

  115 Olde Potomac Ave, Winchester, KY 40391

  Last Sold Summary

  • 16% Above List Price
  • $111/SF
  • 3 Days On Market

  Last Sold Price $224,400

  Last Listing Agent Christa Joynt Keller Williams Commonwealth
• 

  

  /83

  $849,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,768 Sq Ft

  4755 Combs Ferry Rd, Winchester, KY 40391

  Welcome to Windswept Farm located on a most desirable piece of Kentucky Bluegrass. Located approximately 15 minutes from Hamburg, Lexington, you can also be in Richmond in about the same amount of time and Historic Downtown Winchester. This property has been meticulously maintained, from the ranch style house with an awesome 2 car garage with storage, a detached heated 3 car garage and an

  Craig Bridgewater Bridgewater Real Estate

  4755 Combs Ferry Rd, Winchester, KY 40391
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  /29

  $180,000 Sold Aug 11, 2025

  217 Blair Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,025 Sq Ft
  • Built 1970

  Last Sold Summary

  • 3% Above List Price
  • $176/SF
  • 0 Days On Market

  Current Estimated Value $180,194

  Last Listing Agent Ashley Barreto Indigo & Co

  217 Blair Ave, Winchester, KY 40391
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  /35

  Est $289,766 Not Listed For Sale

  231 W Hickman St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,588 Sq Ft
  • Built 1923

  231 W Hickman St, Winchester, KY 40391

  Last Sold Summary

  • 35% Above List Price
  • $83/SF
  • 38 Days On Market

  Last Sold Price $215,000

  Last Listing Agent Michelle Blackburn RE/MAX
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  /2

  $110,000

  • Land
  • 0.59 Acre
  • $186,441 per Acre

  255 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

  255 Duclair Dr, Winchester, KY 40391
• 

  

  /30

  $254,000 Sold Dec 02, 2025

  312 Forest Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,550 Sq Ft
  • Built 1962

  Last Sold Summary

  • 6% Below List Price
  • $164/SF
  • 52 Days On Market

  Current Estimated Value $250,139

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

  312 Forest Ave, Winchester, KY 40391
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  /36

  Est $222,067 Not Listed For Sale

  242 W Lexington Ave, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,755 Sq Ft
  • Built 1940

  242 W Lexington Ave, Winchester, KY 40391

  Last Sold Summary

  • 6% Above List Price
  • $120/SF
  • 49 Days On Market

  Last Sold Price $210,000

  Last Listing Agent Danny Hudnall Thwaites Realtors LLC
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  /10

  $775,000

  • Land
  • 3 Acres
  • $258,333 per Acre

  609 Bullion Blvd Unit 3A, Winchester, KY 40391

  Ideally located along the heart of Bypass Road (ADT: 24,801) in Winchester, Kentucky between and surrounding Kroger and Walmart shopping centers. These lots are offered as 1+ acres and may be subdivided. Winchester, KY is the county seat of Clark County, KY and is part of the Lexington-Fayette KY Metropolitan Statistical Area, and is supported by such industries such as Amazon, Ale-8-One, and

  Greg Leveridge Block + Lot Real Estate

  609 Bullion Blvd Unit 3A, Winchester, KY 40391
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  /75

  $410,000 Sold Nov 21, 2025

  291 Log Lick Rd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,600 Sq Ft
  • Built 2007

  Last Sold Summary

  • 6% Below List Price
  • $158/SF
  • 3 Days On Market

  Current Estimated Value $409,157

  Last Listing Agent Joyce Ratliff Tom Goebel & Company

  291 Log Lick Rd, Winchester, KY 40391

Showing Results 641 - 680, Page 17 of 18