Winchester, KY Homes

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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 $212,516

  Last Listing Agent Peggy Baldridge HomeFirst Real Estate

  206 W Clark Dr, Winchester, KY 40391
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  /75

  Est $286,998 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,844 Sq Ft

  314 Fern Ct, Winchester, KY 40391

  314 Fern Ct, Winchester, KY 40391
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  /8

  $195,000

  • Land
  • 6.15 Acres
  • $31,707 per Acre

  990 Craig Crossing Rd, Winchester, KY 40391

  Lot # 13 contains 6.153 acres of gently rolling land perfect for your new home. This is a rare opportunity to own a piece of western Clark County real estate in the sought-after McClure Road area. Thoroughbred Estates is Winchester's newest upscale development containing 33 lots from 2 acres to nearly 7 acres. Lots are located just minutes from Winchester and Lexington.

  Keith Wilson Coldwell Banker McMahan

  990 Craig Crossing Rd, 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 $170,444

  Last Listing Agent Null Non-Member Non-Member Office

  Unlisted Address
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  /23

  Est $149,218 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,330 Sq Ft

  464 Ecton Rd, Winchester, KY 40391

  464 Ecton Rd, Winchester, KY 40391
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  /29

  $249,500 Pending

  • 3 Beds
  • 2 Baths
  • 1,220 Sq Ft

  142 Sturbridge Ln, Winchester, KY 40391

  All on one level, large master bedroom, HVAC less than 2 years old and upgrades made in the last year. Enjoy a private backyard fenced with trees behind. The fence, vinyl siding and gutters were all professionally cleaned last summer. New lighting and minor upgrades made to master bath. Overhead storage added to garage. Sensi thermostat for wifi control of heating and air. New keyless entry on

  Donna Mink Mink Realty

  142 Sturbridge Ln, 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 $304,706

  Last Listing Agent Stephanie Hacker Kentucky Residential Real Estate, LLC

  2482 Mina Station Rd, Winchester, KY 40391
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  /35

  Est $390,920 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,062 Sq Ft

  2195 Pretty Run Rd, Winchester, KY 40391

  2195 Pretty Run Rd, Winchester, KY 40391
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  /2

  $78,500

  • Land
  • 0.22 Acre
  • $356,818 per Acre

  Lot 5 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 5 Plantations Dr, 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 $922,874

  Last Listing Agent Shane Underwood Keller Williams Commonwealth

  118 Bella Shae Way, Winchester, KY 40391
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  /38

  Est $337,745 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,201 Sq Ft

  3635 Jackson Ferry Rd, Winchester, KY 40391

  3635 Jackson Ferry Rd, Winchester, KY 40391
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  /52

  $230,000 Pending

  • 3 Beds
  • 1 Bath
  • 1,134 Sq Ft

  19 Cherokee Ct, Winchester, KY 40391

  This charming 3 bedroom, 1 bath brick ranch offers comfort, convenience, and a functional layout in a peaceful setting at the end of a dead-end street. Step inside to a spacious living room that flows directly into the breakfast area and kitchen—perfect for everyday living or hosting friends and family. The home features a main-level utility room, eliminating stairs and providing easy access for

  Josh Wood Freedom Realty & Property Management

  19 Cherokee Ct, 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 $78,334

  Last Listing Agent Keith Wilson Coldwell Banker McMahan

  120 Jacob Ct, Winchester, KY 40391
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  /105

  Est $710,851 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,557 Sq Ft

  1039 Cole Rd, Winchester, KY 40391

  1039 Cole Rd, Winchester, KY 40391
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  /29

  $399,900

  • 8 Beds
  • 8 Baths
  • 4,000 Sq Ft

  17 W Lexington Ave, Winchester, KY 40391

  Investment Opportunity in the Heart of Downtown Winchester! Discover 17 W. Lexington Ave, a converted commercial building now featuring 8 studio/one-bedroom apartments. Each unit includes a full kitchen and private bath, offering the perfect blend of comfort and convenience for tenants. This multifamily property is ideally situated in historic downtown Winchester, within walking distance to

  Joshua Lynch The Brokerage

  17 W Lexington Ave, Winchester, KY 40391
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  /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 $423,709

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate

  17 Hampton Ave, Winchester, KY 40391
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  /17

  Est $497,411 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,183 Sq Ft

  420 Fairholme Way, Winchester, KY 40391

  420 Fairholme Way, Winchester, KY 40391
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  /6

  $49,500

  • Land
  • 0.98 Acre
  • $50,510 per Acre

  204 Wigeon Ct, Winchester, KY 40391

  Choose your preferred builder to construct your dream home in Mallard Place. Located in a quiet cul-de-sac at the rear of the subdivision. Only a 20 minute drive to Hamburg/Lexington and only a 5 minute drive to the Winchester Bypass. Enjoy the serenity of living in a private setting AND the convenience of being close to schools, shopping and I-64 and I-75.

  Jim Woodrum RE/MAX Creative, Winchester

  204 Wigeon Ct, Winchester, KY 40391
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  /19

  $175,000 Sold Apr 18, 2025

  11 Shelley Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft
  • Built 1970

  Last Sold Summary

  • 3% Below List Price
  • $147/SF
  • 5 Days On Market

  Current Estimated Value $191,273

  Last Listing Agent Tonya Morrow KY Local

  11 Shelley Dr, Winchester, KY 40391
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  /44

  Est $409,247 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,304 Sq Ft

  207 Citation Ct, Winchester, KY 40391

  207 Citation Ct, Winchester, KY 40391
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  /34

  $260,000

  • Land
  • 6.08 Acres
  • $42,763 per Acre

  190 Privacy Ln, Winchester, KY 40391

  6.08 acres settled in Clark County with access from both Privacy Ln and Little Stoner Rd. This property boasts a 30x56 with 10 foot wall Kentucky Steel Truss building with concrete floors, gas and wood burning heat, full bath, and a car lift. Additionally, there is a barn with a 3 bay shed attached.

  Jason Joseph Keller Williams Commonwealth

  190 Privacy Ln, 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 $241,956

  Last Listing Agent Vickie Skeens RE/MAX Elite Lexington

  129 Bay Hill Dr, Winchester, KY 40391
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  /8

  Est $499,626 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 4,447 Sq Ft

  419 Fairholme Way, Winchester, KY 40391

  419 Fairholme Way, Winchester, KY 40391
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  /3

  $395,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,855 Sq Ft

  205 Evergreen Dr, Winchester, KY 40391

  Introducing The Mulberry floor plan - a beautifully designed proposed construction home in the scenic Locust Hill Acres community. This open-concept floor plan offers the perfect blend of comfort and functionality with 3 bedrooms, 2 full bathrooms, and thoughtful living spaces throughout.The spacious primary suite features a large walk-in closet and a private ensuite bath, providing a

  Rex Hall United Real Estate Bluegrass

  205 Evergreen Dr, Winchester, KY 40391
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  /34

  $380,000 Sold Nov 21, 2025

  110 Hampton Avenue Exd, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,516 Sq Ft

  Last Sold Summary

  • 1% Above List Price
  • $151/SF
  • 5 Days On Market

  Last Listing Agent Erin Lewis Christies International Real Estate Bluegrass

  110 Hampton Avenue Exd, Winchester, KY 40391
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  /20

  Est $410,287 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,487 Sq Ft

  307 Gallahadion Ct, Winchester, KY 40391

  307 Gallahadion Ct, Winchester, KY 40391
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  /24

  $275,000

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft

  120 Sunset Heights, Winchester, KY 40391

  Your search is over with this hard to find 3 bedroom 2 bathroom ranch located close to town, College Park and featured a nice fenced level yard. Your will love the cathedral ceiling in the Great Room and Kitchen as well as the above ground pool with a new liner ready to be installed. You will love the oversized rear deck which will be great for entertaining. A covered front porch as well as

  Keith Wilson Coldwell Banker McMahan

  120 Sunset Heights, Winchester, KY 40391
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  /30

  $289,100 Sold Nov 03, 2025

  223 Bartram Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,606 Sq Ft
  • Built 2004

  Last Sold Summary

  • $180/SF
  • 46 Days On Market

  Last Listing Agent Jennifer Parsons RE/MAX Elite Lexington

  223 Bartram Ct, Winchester, KY 40391
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  /33

  Est $328,541 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,475 Sq Ft

  305 Gallahadion Ct, Winchester, KY 40391

  305 Gallahadion Ct, Winchester, KY 40391
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  /35

  $349,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,100 Sq Ft

  121 Fitch Ave, Winchester, KY 40391

  *Under contract with a 48-hour kick out clause. Please continue to show and bring offers* This beautifully updated 4-bedroom, 3-bath ranch home includes a private mother-in-law suite, offering flexible living options for guests or extended family. With 2,100 square feet of inviting living space and an attached two-car garage, this home perfectly combines timeless charm with thoughtful modern

  Ashley Spencer Keller Williams Commonwealth

  121 Fitch Ave, Winchester, KY 40391
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  /42

  $400,000 Sold Dec 05, 2025

  210 College St, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 2,718 Sq Ft
  • Built 1895

  Last Sold Summary

  • 5% Below List Price
  • $147/SF
  • 59 Days On Market

  Last Listing Agent Erin Lewis Christies International Real Estate Bluegrass

  210 College St, Winchester, KY 40391
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  /15

  Est $201,515 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,260 Sq Ft

  432 Country Club Dr, Winchester, KY 40391

  432 Country Club Dr, Winchester, KY 40391
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  /45

  $290,000

  • 3 Beds
  • 1 Bath
  • 1,523 Sq Ft

  4180 Bybee Rd, Winchester, KY 40391

  This full brick ranch style house is located on 5.7 acres of Kentucky Bluegrass in Clark County. The cleared land on the property is approximately 3/4 acre and the remaining acres are all wooded. The interior has 3 bedrooms and one full bath. There is an addition of a den, dining area and a rear deck. The den features a full masonry fireplace. The barn is great place for storage or a workshop.

  Craig Bridgewater Bridgewater Real Estate

  4180 Bybee Rd, Winchester, KY 40391
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  /64

  $360,000 Sold Oct 17, 2025

  309 Gallahadion Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,920 Sq Ft
  • Built 2024

  Last Sold Summary

  • 3% Below List Price
  • $188/SF
  • 60 Days On Market

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  309 Gallahadion Ct, Winchester, KY 40391
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  /16

  Est $180,631 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,260 Sq Ft

  430 Country Club Dr, Winchester, KY 40391

  430 Country Club Dr, Winchester, KY 40391
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  /24

  $290,000

  • 12 Beds
  • 4 Baths
  • 4,010 Sq Ft

  149 Winn Ave, Winchester, KY 40391

  Welcome to this quad plex income producing property. It is a large lot and the property sits back on the lot away from the road. There are 4 units, each with 3 beds and 1 bath. The whole building has a total of bedrooms of 12 beds and 4 baths. Each unit has its own kitchen. The pictures are of the only vacant unit on the bottom left. The two lower units rent for $950 and $925. The upper units

  Libby VanMeter Marshall Lane Real Estate - Lexington

  149 Winn Ave, Winchester, KY 40391
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  /23

  $130,000 Sold Apr 24, 2025

  103 Gary Ct, Winchester, KY 40391

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

  Last Sold Summary

  • 7% Below List Price
  • $129/SF
  • 13 Days On Market

  Current Estimated Value $146,749

  Last Listing Agent Dawn Wheeler United Real Estate Bluegrass

  103 Gary Ct, Winchester, KY 40391
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  /25

  Est $214,706 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft

  413 Country Club Dr, Winchester, KY 40391

  413 Country Club Dr, Winchester, KY 40391
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  /49

  $450,000

  • 3 Beds
  • 2.5 Baths
  • 2,258 Sq Ft

  233 Cunningham Ln, Winchester, KY 40391

  Mini Farm Alert! This fabulous homestead is located less than 2 miles off the Mountain Parkway making it easily accessible. One level, ranch home that features 3 bedrooms, a luxurious primary ensuite... corner jetter tub, seperate walk in shower with glass door, double bowl raised height vanity and a linen closet complete the bathroom and the bedroom has vaulted ceilings, walk in closet and

  Amanda Marcum Berkshire Hathaway HomeServices Foster Realtors

  233 Cunningham Ln, Winchester, KY 40391
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  /23

  $225,000 Sold Aug 21, 2025

  26 Stefanie Ct, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,080 Sq Ft
  • Built 1972

  Last Sold Summary

  • $208/SF
  • 12 Days On Market

  Current Estimated Value $225,213

  Last Listing Agent Alyssa M Boley Coldwell Banker McMahan

  26 Stefanie Ct, Winchester, KY 40391

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