Winchester, KY Homes

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  /22

  $88,000 Sold May 08, 2025

  423 E Broadway St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 2,363 Sq Ft
  • Built 1878

  Last Sold Summary

  • 76% Above List Price
  • $37/SF
  • 23 Days On Market

  Current Estimated Value $171,012

  Last Listing Agent Tanya McKee Bluegrass Auction, Appraisal & Realty, LLC

  423 E Broadway St, Winchester, KY 40391
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  /20

  Est $369,879 Not Listed For Sale

  307 Gallahadion Ct, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,487 Sq Ft
  • Built 2004

  307 Gallahadion Ct, Winchester, KY 40391

  Last Sold Summary

  • 10% Above List Price
  • $135/SF
  • 18 Days On Market

  Last Sold Price $335,000

  Last Listing Agent Lindsay Rhodus Keller Williams Legacy Group
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  /7

  $800,000 Pending

  • Land
  • 4.87 Acres
  • $164,271 per Acre

  1108 W Lexington Ave, Winchester, KY 40391

  Rare opportunity to purchase a large multi-family development in the heart of Winchester! Directly across the street from Legacy Grove Park! All building and engineering plans included to build 66 approved townhomes with the possibility of adding 4 more. Currently zoned PD (Planned Development), could possibly be changed to commercial due to neighboring commercial property. Main property is 4.87

  Jason Townsend Kentucky Residential Real Estate, LLC

  1108 W Lexington Ave, Winchester, KY 40391
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  /44

  $315,000 Sold Jun 27, 2025

  43 Skylark Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,459 Sq Ft
  • Built 1981

  Last Sold Summary

  • 6% Below List Price
  • $128/SF
  • 70 Days On Market

  Current Estimated Value $331,544

  Last Listing Agent Chad Bowman The Brokerage

  43 Skylark Dr, Winchester, KY 40391
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  /33

  Est $286,759 Not Listed For Sale

  305 Gallahadion Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,475 Sq Ft
  • Built 2004

  305 Gallahadion Ct, Winchester, KY 40391

  Last Sold Summary

  • 7% Above List Price
  • $182/SF
  • 55 Days On Market

  Last Sold Price $268,000

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC
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  /21

  $430,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft

  870 Pilot View Rd, Winchester, KY 40391

  Welcome to your own slice of paradise! This 2022 doublewide sits on an impressive 39.5 acres of rolling countryside in Winchester, offering the perfect blend of modern comfort, privacy, and wide-open space. Step outside and take in the beautiful pastures, ideal for horses, cattle, or hobby farming, all complemented by a peaceful creek that winds through the property—perfect for relaxing evenings

  Chelsea Morguson McCallie Real Estate

  870 Pilot View Rd, Winchester, KY 40391
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  /2

  $350,000 Sold Aug 14, 2025

  Unlisted Address

  • 4 Beds
  • 2.5 Baths
  • 3,672 Sq Ft
  • Built 1960

  Last Sold Summary

  • $95/SF

  Current Estimated Value $346,724

  Last Listing Agent Null Non-Member Non-Member Office

  Unlisted Address
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  /15

  Est $195,486 Not Listed For Sale

  432 Country Club Dr, Winchester, KY 40391

  • 2 Beds
  • 2 Baths
  • 1,260 Sq Ft
  • Built 1982

  432 Country Club Dr, Winchester, KY 40391

  Last Sold Summary

  • 18% Above List Price
  • $131/SF
  • 19 Days On Market

  Last Sold Price $165,000

  Last Listing Agent Brian England Keller Williams Bluegrass Realty
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  /8

  $175,000

  • Land
  • 6.59 Acres
  • $26,555 per Acre

  990 Craig Crossing Rd, Winchester, KY 40391

  Lot # 13 contains 6.588 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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  /28

  $265,000 Sold Jul 02, 2025

  609 Clintonville Rd, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,305 Sq Ft
  • Built 1980

  Last Sold Summary

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

  Current Estimated Value $268,683

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate

  609 Clintonville Rd, Winchester, KY 40391
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  /16

  Est $191,225 Not Listed For Sale

  430 Country Club Dr, Winchester, KY 40391

  • 2 Beds
  • 2 Baths
  • 1,260 Sq Ft
  • Built 1982

  430 Country Club Dr, Winchester, KY 40391

  Last Sold Summary

  • 16% Above List Price
  • $131/SF
  • 5 Days On Market

  Last Sold Price $165,000

  Last Listing Agent Brian England Keller Williams Bluegrass Realty
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  /62

  $319,500

  • 8 Beds
  • 5 Baths
  • 3,637 Sq Ft

  144 Holly Ave, Winchester, KY 40391

  Excellent investment opportunity featuring two income-producing buildings on one lot, offered together as a package deal. This unique multifamily property includes a triplex and a separate duplex, making it ideal for investors looking to expand their portfolio with multiple units in one purchase. The triplex (Building A) consists of three units: Unit A-1: 2 bedrooms, 1 bathroom Unit A-2: 1

  Shane Underwood Keller Williams Commonwealth

  144 Holly Ave, Winchester, KY 40391
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  /12

  $9,000 Sold Sep 18, 2025

  406 W Washington St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,428 Sq Ft
  • Built 1945

  Last Sold Summary

  • 10% Below List Price
  • $6/SF
  • 19 Days On Market

  Current Estimated Value $146,704

  Last Listing Agent Jack Rookard Rookard Real Estate Consultants

  406 W Washington St, Winchester, KY 40391
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  /25

  Est $189,276 Not Listed For Sale

  413 Country Club Dr, Winchester, KY 40391

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • Built 1978

  413 Country Club Dr, Winchester, KY 40391

  Last Sold Summary

  • 56% Above List Price
  • $110/SF
  • 0 Days On Market

  Last Sold Price $121,500

  Last Listing Agent Kelly Nisbet Coldwell Banker McMahan
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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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  /79

  $425,000 Sold Feb 23, 2026

  1410 Dry Fork Creek Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,064 Sq Ft

  Last Sold Summary

  • 15% Below List Price
  • $399/SF
  • 78 Days On Market

  Current Estimated Value $312,840

  Last Listing Agent Skyler Lewis Dream Maker Realty, LLC

  1410 Dry Fork Creek Rd, Winchester, KY 40391
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  /86

  Est $288,189 Not Listed For Sale

  222 Vaught Rd, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,904 Sq Ft
  • Built 1970

  222 Vaught Rd, Winchester, KY 40391

  Last Sold Summary

  • 6% Above List Price
  • $143/SF
  • 3 Days On Market

  Last Sold Price $271,900

  Last Listing Agent Josh Wood Freedom Realty & Property Management
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  /36

  $199,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft

  58 Hughes Ave, Winchester, KY 40391

  Nice remodeled 3 bedroom and 2 bath home...Ranch on a basement...2 bed 1 bath upstairs and Basement has another living area with 1 bedroom and 1 bath. Fresh paint , new lights, newer hvac and newer windows. Kitchen has been updated with granite, appliances and fresh paint....agent owner

  E Anthony Phillips RE/MAX Creative Realty

  58 Hughes Ave, Winchester, KY 40391
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  /55

  $520,000 Sold May 15, 2025

  427 Calmes Blvd, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 4,659 Sq Ft
  • Built 1995

  Last Sold Summary

  • 4% Below List Price
  • $112/SF
  • 61 Days On Market

  Current Estimated Value $487,160

  Last Listing Agent Kymberly McCreary EXP Realty, LLC

  427 Calmes Blvd, Winchester, KY 40391
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  /38

  Est $265,305 Not Listed For Sale

  2020 Two Mile Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,320 Sq Ft
  • Built 1950

  2020 Two Mile Rd, Winchester, KY 40391

  Last Sold Summary

  • 5% Below List Price
  • $212/SF
  • 37 Days On Market

  Last Sold Price $280,000

  Last Listing Agent Dale Hatton Dream Maker Realty, LLC
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  /24

  $97,000 Pending

  • 2 Beds
  • 1 Bath
  • 996 Sq Ft

  701 Williamsburg Dr, Winchester, KY 40391

  Completely renovated from top to bottom, this move-in-ready manufactured home on a permanent foundation offers quality, comfort, and value all in one package! Featuring 2 bedrooms, 1 full bath, and 996 sq ft of thoughtfully updated living space, this home showcases a high level of finish rarely found at this price point. Inside, you'll find all new drywall and electrical, new laminate flooring

  Shane Underwood Keller Williams Commonwealth

  701 Williamsburg Dr, Winchester, KY 40391
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  /24

  $188,000 Sold Jan 29, 2026

  27 Ashland Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,653 Sq Ft
  • Built 1950

  Last Sold Summary

  • 6% Below List Price
  • $114/SF
  • 112 Days On Market

  Current Estimated Value $187,052

  Last Listing Agent Robin Mobley-Mosher Marshall Lane Real Estate - Lexington

  27 Ashland Ave, Winchester, KY 40391
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  /13

  Est $191,506 Not Listed For Sale

  4 Burton Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,330 Sq Ft
  • Built 1948

  4 Burton Ave, Winchester, KY 40391

  Last Sold Summary

  • 32% Above List Price
  • $109/SF
  • 1 Day On Market

  Last Sold Price $145,000

  Last Listing Agent Amanda McMillian RE/MAX
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  /12

  $269,900

  • 4 Beds
  • 1 Bath
  • 1,610 Sq Ft

  120 Windsor Dr, Winchester, KY 40391

  Welcome home to this cozy brick charmer in the desirable Belair Subdivision of Winchester, KY! This inviting 4 bedroom, 1 bath home offers comfortable living with a warm electric fireplace perfect for relaxing evenings. The spacious layout provides flexibility for family, guests, or a home office. Step outside to a fully fenced backyard ideal for pets, play, or enjoying quiet mornings with your

  Team Farthing - Mitch Farthing Southern Legacy Realty

  120 Windsor Dr, Winchester, KY 40391
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  /3

  $165,000 Sold Mar 10, 2025

  785 Ecton Rd, Winchester, KY 40391

  • Land
  • 2.67 Acres
  • $61,798 per Acre

  Last Sold Summary

  • 6% Below List Price
  • 579 Days On Market

  Current Estimated Value $171,042

  Last Listing Agent Lara Thornbury Block + Lot Real Estate

  785 Ecton Rd, Winchester, KY 40391
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  /26

  Est $191,178 Not Listed For Sale

  64 Bond Ct, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,025 Sq Ft
  • Built 1987

  64 Bond Ct, Winchester, KY 40391

  Last Sold Summary

  • 19% Above List Price
  • $156/SF
  • 18 Days On Market

  Last Sold Price $160,000

  Last Listing Agent Jim Woodrum RE/MAX
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  /29

  $389,900

  • 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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  /25

  $375,000 Sold Aug 29, 2025

  317 Hanover Dr, Winchester, KY 40391

  • 5 Beds
  • 3.5 Baths
  • 3,111 Sq Ft
  • Built 2001

  Last Sold Summary

  • 1% Below List Price
  • $121/SF
  • 8 Days On Market

  Current Estimated Value $378,391

  Last Listing Agent Mike Wheatley Bluegrass Properties Group

  317 Hanover Dr, Winchester, KY 40391
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  /22

  Est $186,243 Not Listed For Sale

  101 Baldwin Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 925 Sq Ft

  101 Baldwin Ave, Winchester, KY 40391

  Last Sold Summary

  • 20% Above List Price
  • $168/SF
  • 2 Days On Market

  Last Sold Price $155,000

  Last Listing Agent James Jeffries Brickhouse Real Estate
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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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  /60

  $545,000 Sold Oct 31, 2025

  445 Lynnway Dr, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 3,649 Sq Ft
  • Built 1993

  Last Sold Summary

  • $149/SF
  • 4 Days On Market

  Current Estimated Value $545,887

  Last Listing Agent Janna Smith United Real Estate Bluegrass

  445 Lynnway Dr, Winchester, KY 40391
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  /28

  Not Listed For Sale

  916 Muddy Creek Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,000 Sq Ft
  • Built 1943

  916 Muddy Creek Rd, Winchester, KY 40391

  Last Sold Summary

  • 13% Above List Price
  • $195/SF
  • 39 Days On Market

  Last Sold Price $195,000

  Last Listing Agent Janet Jones RE/MAX
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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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  /27

  $380,000 Sold Nov 10, 2025

  5705 Mount Sterling Rd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,980 Sq Ft
  • Built 1971

  Last Sold Summary

  • 5% Below List Price
  • $128/SF
  • 50 Days On Market

  Current Estimated Value $374,923

  Last Listing Agent Dale Hatton Dream Maker Realty, LLC

  5705 Mount Sterling Rd, Winchester, KY 40391
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  /25

  Est $239,087 Not Listed For Sale

  1291 Muddy Creek Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,239 Sq Ft
  • Built 1952

  1291 Muddy Creek Rd, Winchester, KY 40391

  Last Sold Summary

  • 1% Above List Price
  • $190/SF
  • 65 Days On Market

  Last Sold Price $236,000

  Last Listing Agent Dalis Alvarez GSP Homes
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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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  /102

  $525,000 Sold Dec 22, 2025

  1953 Cabin Creek Rd, Winchester, KY 40391

  • 6 Beds
  • 4.5 Baths
  • 3,846 Sq Ft
  • Built 1980

  Last Sold Summary

  • 4% Below List Price
  • $137/SF
  • 9 Days On Market

  Current Estimated Value $541,267

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  1953 Cabin Creek Rd, Winchester, KY 40391
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  /20

  Est $263,243 Not Listed For Sale

  1121 Muddy Creek Rd, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,498 Sq Ft
  • Built 1940

  1121 Muddy Creek Rd, Winchester, KY 40391

  Last Sold Summary

  • 32% Above List Price
  • $134/SF
  • 9 Days On Market

  Last Sold Price $200,000

  Last Listing Agent Cheri Shaffer Keller Williams Commonwealth
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  /61

  $925,000 New Construction

  • 5 Beds
  • 3.5 Baths
  • 2,842 Sq Ft

  1150 Craig Crossing, Winchester, KY 40391

  Stunning new construction offering 5 bedrooms, 3.5 bathrooms, sitting on roughly 2.5 serene acres. This home is surrounded by picturesque farmland and panoramic views. 4 bedrooms are located on the main level for ultimate convenience. Offering the perfect blend of space, style, and serenity. Features include open concept layout, spacious kitchen with kitchen island, granite counter tops, hidden

  Stephanie Hacker Kentucky Residential Real Estate, LLC

  1150 Craig Crossing, Winchester, KY 40391
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  /28

  $345,000 Sold Jun 19, 2025

  512 Boone Ave, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 3,149 Sq Ft
  • Built 1950

  Last Sold Summary

  • 14% Below List Price
  • $110/SF
  • 58 Days On Market

  Current Estimated Value $376,448

  Last Listing Agent Jordan James Lifstyl Real Estate

  512 Boone Ave, Winchester, KY 40391

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