Winchester, KY Homes

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  /74

  Est $485,413 Not Listed For Sale

  4 Moundale Ave, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,941 Sq Ft
  • Built 1945

  4 Moundale Ave, Winchester, KY 40391

  Last Sold Summary

  • 18% Below List Price
  • $201/SF
  • 3 Days On Market

  Last Sold Price $590,000

  Last Listing Agent Janna Smith United Real Estate Bluegrass
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  /2

  $110,000

  • Land
  • 0.29 Acre
  • $379,310 per Acre

  160 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

  160 Duclair Dr, Winchester, KY 40391
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  /40

  $206,000 Sold Apr 29, 2025

  194 Spruce Ct, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,053 Sq Ft
  • Built 1970

  Last Sold Summary

  • 2% Below List Price
  • $196/SF
  • 25 Days On Market

  Current Estimated Value $211,492

  Last Listing Agent Peggy Baldridge HomeFirst Real Estate

  194 Spruce Ct, Winchester, KY 40391
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  /73

  Est $581,952 Not Listed For Sale

  12 Moundale Ave, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 3,236 Sq Ft
  • Built 1911

  12 Moundale Ave, Winchester, KY 40391

  Last Sold Summary

  • 21% Above List Price
  • $148/SF
  • 1 Day On Market

  Last Sold Price $479,000

  Last Listing Agent Janna Smith United Real Estate Bluegrass
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  /14

  $240,000

  • 3 Beds
  • 2.5 Baths
  • 2,380 Sq Ft

  10 Upper St, Winchester, KY 40391

  Modern Ranch residence full un-finished basement, large lot.

  E. Clark Toleman Real Estate Appraisal Services

  10 Upper St, Winchester, KY 40391
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  /31

  $240,200 Sold Oct 28, 2025

  203 Inverness Ln, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,935 Sq Ft
  • Built 2004

  Last Sold Summary

  • 2% Below List Price
  • $124/SF
  • 16 Days On Market

  Current Estimated Value $243,201

  Last Listing Agent Kymberly McCreary EXP Realty, LLC

  203 Inverness Ln, Winchester, KY 40391
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  /43

  Est $272,773 Not Listed For Sale

  373 Crescent Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,009 Sq Ft
  • Built 1940

  373 Crescent Ave, Winchester, KY 40391

  Last Sold Summary

  • 14% Above List Price
  • $119/SF
  • 28 Days On Market

  Last Sold Price $238,500

  Last Listing Agent Janna Smith United Real Estate Bluegrass
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  /29

  $329,500 Pending

  • 3 Beds
  • 2 Baths
  • 1,719 Sq Ft

  374 N Middletown Rd, Winchester, KY 40391

  Investment Opportunity! This is the Parent Listing. 2 Parcels listed for $339,500 (MLS listing #s 25005575 and 25005577). 2 (titled) Manufactured double-wide homes on permanent foundations sitting on ten acres in Clark County KY. Both properties, 374 and 360 N. Middletown Rd., are being offered together. (Child listing is 360 N. Middletown Rd). Mature garden and LOTS of potential. You could

  Danielle Haggard Keller Williams Commonwealth

  374 N Middletown Rd, Winchester, KY 40391
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  /13

  $38,700 Sold May 20, 2025

  11 Spring St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • Built 1945

  Last Sold Summary

  • 3% Below List Price
  • $35/SF
  • 33 Days On Market

  Current Estimated Value $44,238

  Last Listing Agent Jason Szaks EXIT TOWN & COUNTRY REALTORS

  11 Spring St, Winchester, KY 40391
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  /38

  Est $248,174 Not Listed For Sale

  377 Crescent Ave, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,540 Sq Ft
  • Built 1940

  377 Crescent Ave, Winchester, KY 40391

  Last Sold Summary

  • 13% Above List Price
  • $143/SF
  • 0 Days On Market

  Last Sold Price $219,900

  Last Listing Agent Lori Tolson Lifstyl Real Estate
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  /3

  $645,000 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,526 Sq Ft

  106 Bella Shae Way, Winchester, KY 40391

  Welcome Home to the Claiborne Floor Plan by CP Builders. This stunning 4-bedroom, 2.5-bathroom home offers a luxurious and spacious living experience. The first floor features a magnificent primary suite complete with a spacious ensuite bathroom, a walk-in closet, and direct access to the backyard. The open floor plan seamlessly connects the living, dining, and kitchen areas, creating a warm and

  Shane Underwood Keller Williams Commonwealth

  106 Bella Shae Way, Winchester, KY 40391
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  /36

  $345,000 Sold Jun 02, 2025

  1173 Lafayette Blvd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,910 Sq Ft
  • Built 1996

  Last Sold Summary

  • 3% Below List Price
  • $181/SF
  • 36 Days On Market

  Current Estimated Value $359,627

  Last Listing Agent Janna Smith United Real Estate Bluegrass

  1173 Lafayette Blvd, Winchester, KY 40391
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  /27

  Est $343,894 Not Listed For Sale

  200 Moundale Ave, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 3,428 Sq Ft
  • Built 1960

  200 Moundale Ave, Winchester, KY 40391

  Last Sold Summary

  • 2% Below List Price
  • $102/SF
  • 84 Days On Market

  Last Sold Price $350,000

  Last Listing Agent Kelly Nisbet Coldwell Banker McMahan
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  /9

  $206,000

  • Land
  • 7.77 Acres
  • $26,512 per Acre

  368 Flanagan Station Rd, Winchester, KY 40391

  Build your dream retreat on this beautiful 7.77-acre parcel nestled in a peaceful rural setting just outside Winchester. The gently rolling terrain provides a serene backdrop for your custom home, hobby farm, or equestrian space, offering plenty of room to roam, garden, or simply enjoy the privacy. With easy access from Flanagan Station Road, this property combines a quiet country feel with

  Shari Frasure Keller Williams Commonwealth

  368 Flanagan Station Rd, Winchester, KY 40391
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  /43

  $339,000 Sold Feb 12, 2026

  106 Gibson Way, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,064 Sq Ft
  • Built 2021

  Last Sold Summary

  • $164/SF
  • 1 Day On Market

  Current Estimated Value $329,370

  Last Listing Agent Brittany Nester RO&CO Real Estate

  106 Gibson Way, Winchester, KY 40391
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  /48

  Est $363,115 Not Listed For Sale

  220 Moundale Ave, Winchester, KY 40391

  • 2 Beds
  • 2.5 Baths
  • 2,175 Sq Ft
  • Built 1964

  220 Moundale Ave, Winchester, KY 40391

  Last Sold Summary

  • 17% Above List Price
  • $142/SF
  • 24 Days On Market

  Last Sold Price $309,500

  Last Listing Agent Janna Smith United Real Estate Bluegrass
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  /6

  $388,000

  • 5 Beds
  • 3 Baths
  • 2,762 Sq Ft

  101 E Lexington Ave, Winchester, KY 40391

  Here's your chance to own a nice investment property. This triplex has a 2 bed 1 bath unit, 2 bed 1 bath unit, and a 1 bed 1 bath unit. This property is part of a larger portfolio and you can mix and match properties to your liking. Reach out for the full list of properties. Do NOT disturb tenants.

  David Espinosa Bluegrass Realty Pros, Inc

  101 E Lexington Ave, Winchester, KY 40391
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  /18

  $240,000 Sold Mar 14, 2025

  110 Buckingham Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,240 Sq Ft
  • Built 2001

  Last Sold Summary

  • $194/SF
  • 8 Days On Market

  Current Estimated Value $277,471

  Last Listing Agent Jonathan Wood HomeLand Real Estate Inc - Mt Sterling

  110 Buckingham Ln, Winchester, KY 40391
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  /28

  Est $234,404 Not Listed For Sale

  358 Crescent Ave, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,764 Sq Ft
  • Built 1950

  358 Crescent Ave, Winchester, KY 40391

  Last Sold Summary

  • 4% Above List Price
  • $127/SF
  • 2 Days On Market

  Last Sold Price $224,900

  Last Listing Agent Lucy Martin Jenkins United Real Estate Bluegrass
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  /21

  $189,500

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

  109 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

  109 Quail Ridge Rd, Winchester, KY 40391
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  /36

  $472,500 Sold Sep 09, 2025

  208 Royal Oak Dr, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,593 Sq Ft
  • Built 2007

  Last Sold Summary

  • 1% Above List Price
  • $182/SF
  • 1 Day On Market

  Current Estimated Value $466,954

  Last Listing Agent Megan McCoy Keller Williams Legacy Group

  208 Royal Oak Dr, Winchester, KY 40391
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  /77

  Est $318,208 Not Listed For Sale

  328 S Main St, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,709 Sq Ft
  • Built 1900

  328 S Main St, Winchester, KY 40391

  Last Sold Summary

  • 33% Above List Price
  • $89/SF
  • 26 Days On Market

  Last Sold Price $240,000

  Last Listing Agent Josh Wood Freedom Realty & Property Management
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  /24

  $329,500 Pending

  • 3 Beds
  • 2 Baths
  • 1,792 Sq Ft

  360 N Middletown Rd, Winchester, KY 40391

  Investment Opportunity! This is the Child Listing. 2 Parcels listed for $339,500 (MLS listing #s 25005575 and 25005577). 2 (titled) Manufactured double-wide homes on permanent foundations sitting on ten acres in Clark County KY. Both properties, 374 and 360 N. Middletown Rd., are being offered together. (Child listing is 360 N. Middletown Rd). Mature garden and LOTS of potential. You could

  Danielle Haggard Keller Williams Commonwealth

  360 N Middletown Rd, Winchester, KY 40391
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  /6

  $51,000 Sold May 14, 2025

  214 Ashton Oak Way, Winchester, KY 40391

  • Land
  • 0.25 Acre
  • $204,000 per Acre

  Last Sold Summary

  • 7% Below List Price
  • 325 Days On Market

  Current Estimated Value $53,534

  Last Listing Agent Melia Hord Keller Williams Legacy Group

  214 Ashton Oak Way, Winchester, KY 40391
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  /57

  Est $342,620 Not Listed For Sale

  286 S Main St, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 3,689 Sq Ft
  • Built 1910

  286 S Main St, Winchester, KY 40391

  Last Sold Summary

  • 1% Above List Price
  • $92/SF
  • 9 Days On Market

  Last Sold Price $340,000

  Last Listing Agent Kelly Nisbet Coldwell Banker McMahan
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  /3

  $251,000 Pending

  • 6 Beds
  • 3 Baths
  • 2,302 Sq Ft

  133 S Highland St, Winchester, KY 40391

  16 Central Ave, Winchester, KY 40391Prime multi-family investment in a great Winchester location! This 2-story property features two spacious rental units, both offering strong income potential. The first unit includes 3 bedrooms and 2 bathrooms, while the second unit offers 3 bedrooms and 1 bathroom—ideal for accommodating a range of tenant needs. With an established rental history and close

  David Espinosa Bluegrass Realty Pros, Inc

  133 S Highland St, Winchester, KY 40391
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  /23

  $135,000 Sold Jul 02, 2025

  2100 Old Log Lick Rd, Winchester, KY 40391

  • Land
  • 5 Acres
  • $27,000 per Acre

  Last Sold Summary

  • 10% Below List Price
  • 69 Days On Market

  Current Estimated Value $142,173

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

  2100 Old Log Lick Rd, Winchester, KY 40391
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  /34

  Est $265,387 Not Listed For Sale

  312 S Main St, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 2,355 Sq Ft
  • Built 1920

  312 S Main St, Winchester, KY 40391

  Last Sold Summary

  • $113/SF
  • 1 Day On Market

  Last Sold Price $265,000

  Last Listing Agent Susan Baldwin Threshold Real Estate Services
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  /41

  $575,000

  • 2 Beds
  • 2 Baths
  • 2,361 Sq Ft

  2100 Stoner-Ephesus Rd, Winchester, KY 40391

  Beautiful 44.21 acre farm has so much to offer. The main residence features 2 spacious bedrooms and 2 full bathrooms, offering inviting living spaces and peaceful views of the surrounding countryside. The separate guest quarters has 1 bedroom and 1 bathroom and is ideal accommodations for visitors, extended family or staff. You will appreciate the thoughtfully designed facilities, including two

  Kelly Nisbet Coldwell Banker McMahan

  2100 Stoner-Ephesus Rd, Winchester, KY 40391
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  /20

  $217,500 Sold Sep 30, 2025

  511 Acadia Way, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 2001

  Last Sold Summary

  • 3% Below List Price
  • $155/SF
  • 28 Days On Market

  Current Estimated Value $216,811

  Last Listing Agent Tyler I Back The Brokerage

  511 Acadia Way, Winchester, KY 40391
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  /52

  Est $271,686 Not Listed For Sale

  14 Lisle Ln, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,673 Sq Ft
  • Built 1955

  14 Lisle Ln, Winchester, KY 40391

  Last Sold Summary

  • 9% Above List Price
  • $149/SF
  • 1 Day On Market

  Last Sold Price $250,000

  Last Listing Agent Meredith Walker Bluegrass Sotheby's International Realty
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  /84

  $849,900

  • 4 Beds
  • 3.5 Baths
  • 4,922 Sq Ft

  2509 Mount Sterling Rd, Winchester, KY 40391

  Embrace Bluegrass living with this beautiful fieldstone ranch on 10+ acres in the heart of horse country. Just minutes from interstate access, yet surrounded by rolling hills and scenic views, this mini farm offers a larger barn with 6 stalls, including water and electric connection, 90 foot roof hangover on the barn, 5 paddocks, each with their own gate and water ran along each paddock. The home

  Josh Wood Freedom Realty & Property Management

  2509 Mount Sterling Rd, Winchester, KY 40391
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  /2

  $99,500 Sold Dec 01, 2025

  1295 Sewell Shop Rd, Winchester, KY 40391

  • Land
  • 8.39 Acres
  • $11,859 per Acre

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Zella Rosenthal Tom Goebel & Company

  1295 Sewell Shop Rd, Winchester, KY 40391
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  /20

  Est $226,894 Not Listed For Sale

  18 Lisle Ln, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,082 Sq Ft
  • Built 1950

  18 Lisle Ln, Winchester, KY 40391

  Last Sold Summary

  • 13% Above List Price
  • $185/SF
  • 0 Days On Market

  Last Sold Price $200,000

  Last Listing Agent Lukas Owens The Brokerage
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  /11

  $249,000

  • 3 Beds
  • 2 Baths
  • 1,534 Sq Ft

  646 Laura Dr, Winchester, KY 40391

  Three bedrooms ranch, that has been updated with a new kitchen, with granite tops ,new appliances, new flooring ,new interior paintiing ,plus much more, located in Verna Hills S/D located between Winchester and Lexington . Owner/Agent

  Garry Milton Milton and Associates Real Estate

  646 Laura Dr, Winchester, KY 40391
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  /2

  $39,500 Sold Mar 05, 2025

  410 Fairholme Way, Winchester, KY 40391

  • Land
  • 0.4 Acre
  • $98,750 per Acre

  Last Sold Summary

  • 14% Above List Price
  • 1,599 Days On Market

  Current Estimated Value $231,282

  Last Listing Agent Garnett Davis Tom Goebel & Company

  410 Fairholme Way, Winchester, KY 40391
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  /51

  Est $324,156 Not Listed For Sale

  20 Lisle Ln, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,421 Sq Ft
  • Built 1955

  20 Lisle Ln, Winchester, KY 40391

  Last Sold Summary

  • 151% Above List Price
  • $53/SF
  • 621 Days On Market

  Last Sold Price $129,000

  Last Listing Agent Jim Woodrum RE/MAX
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  /12

  $188,900

  • 3 Beds
  • 2 Baths
  • 1,116 Sq Ft

  41 7th St, Winchester, KY 40391

  Welcome to 41 7th Street. This brick ranch offers 3 bedrooms, 2 full baths, and hardwood floors throughout the living room, hallway, and bedrooms, ready to be refreshed with a re-sand and polish. The layout provides a foundation for a buyer looking to add personal updates and make it their own. Located at the end of the street, the home offers added privacy along with peaceful farm views behind

  Austina Bruton Re/Max Elite Realty - Hamburg

  41 7th St, Winchester, KY 40391
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  /13

  $140,000 Sold Nov 24, 2025

  220 Pendleton St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 902 Sq Ft

  Last Sold Summary

  • 24% Below List Price
  • $155/SF
  • 37 Days On Market

  Current Estimated Value $138,520

  Last Listing Agent Steve Adams Steven D Adams Real Estate Services, LLC

  220 Pendleton St, Winchester, KY 40391
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  /54

  Est $345,603 Not Listed For Sale

  35 Lisle Ln, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,816 Sq Ft
  • Built 1953

  35 Lisle Ln, Winchester, KY 40391

  Last Sold Summary

  • 21% Above List Price
  • $157/SF
  • 27 Days On Market

  Last Sold Price $285,000

  Last Listing Agent Whitney Ensor Ensor Real Estate, LLC

Showing Results 561 - 600, Page 15 of 18