Winchester, KY Homes

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  $819,000 Open Sun 1PM - 3PM

  • 4 Beds
  • 3.5 Baths
  • 4,345 Sq Ft

  1701 Gay Evans Rd, Winchester, KY 40391

  If you need space, this one delivers. Sitting on just over 8 acres, this brick ranch offers privacy, room to breathe, and a layout that actually makes sense for everyday living. On the main level, you'll find the primary suite, two additional bedrooms, and a formal dining room that works just as well for holidays as it does for weeknight dinners. The heated and cooled sunroom is the kind of spot

  

  Nora Williams

  Keller Williams Commonwealth

  (859) 762-2569

  1701 Gay Evans Rd, Winchester, KY 40391
• Explore Winchester

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  /25

  Call for Price

  Cambridge Square Apartments - Income Based

  1 - 3 Beds

  300 C G Stephenson Dr, Winchester, KY 40391

  This community is open by appt only. Office hours are 9am to 12pm and 1pm to 4pm. Please call to schedule your appt!Cambridge Square is a community with beautifully maintained grounds, offering one, two and three bedroom apartment homes with some one bedroom homes reserved for the elderly/dis-abled, all rent based on income. We are located in quiet Winchester, Kentucky, with easy

  300 C G Stephenson Dr, Winchester, KY 40391
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  /8

  $15,000 Sold Dec 30, 2025

  61 Melbourne St, Winchester, KY 40391

  • Land
  • 0.1 Acre
  • $150,000 per Acre

  Last Sold Summary

  • 40% Below List Price
  • 57 Days On Market

  Current Estimated Value $55,345

  Last Listing Agent Brian Lewis Guide Realty, Inc.

  61 Melbourne St, Winchester, KY 40391
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  /76

  Est $759,764 Not Listed For Sale

  775 Sugar Ridge Rd, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,860 Sq Ft
  • Built 1996

  775 Sugar Ridge Rd, Winchester, KY 40391

  Last Sold Summary

  • 10% Above List Price
  • $241/SF
  • 2 Days On Market

  Last Sold Price $690,000

  Last Listing Agent Cassie Foley CENTURY 21 Advantage Realty
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  /47

  $365,000

  • 4 Beds
  • 3 Baths
  • 2,105 Sq Ft

  114 Mallard Ln, Winchester, KY 40391

  Nestled in a quiet cul-de-sac just minutes from shopping, dining, and the interstate, this unique ranch-style home offers a space, flexibility, and convenience. Originally designed as a duplex, the property has been thoughtfully renovated and modernized for an easy lifestyle. The main living area welcomes you with a light-filled, open concept layout featuring beautiful hardwood floors, a

  

  Robin Jones

  Keller Williams Legacy Group

  (859) 809-3100

  114 Mallard Ln, Winchester, KY 40391
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  /35

  $800 - $1,300 per month

  Summit Apartments

  1 - 3 Beds

  260 Oxford Dr, Winchester, KY 40391

  The Summit located in Winchester; KY is just minutes away from major employers. We are just a short drive from Lexington, KY. Come see our pet friendly community with lots of green space. We have spacious one-, two-, and three-bedroom apartment homes with caring on-site management. Our homes feature walk-in closets, new Laminate Vinyl Plank Flooring, fully equipped kitchens, washer/dryer

  260 Oxford Dr, Winchester, KY 40391
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  /20

  $189,500 Sold Dec 18, 2025

  13015 Irvine Rd, Winchester, KY 40391

  Last Sold Summary

  • 17% Below List Price
  • 134 Days On Market

  Last Listing Agent Mendel Tipton Natural Bridge Realty

  13015 Irvine Rd, Winchester, KY 40391
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  /21

  Est $203,134 Not Listed For Sale

  17 Elizabeth St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,450 Sq Ft
  • Built 1950

  17 Elizabeth St, Winchester, KY 40391

  Last Sold Summary

  • 7% Above List Price
  • $130/SF
  • 24 Days On Market

  Last Sold Price $189,000

  Last Listing Agent Holly Goeing The Agency
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  $219,000

  • 3 Beds
  • 1 Bath
  • 1,188 Sq Ft

  314 E Broadway St, Winchester, KY 40391

  Welcome to this beautifully maintained 3-bedroom, 1-bath ranch offering 1,188 sqft of classic charm on a spacious 0.26-acre lot! This home blends timeless character with thoughtful updates, featuring an inviting single-level layout, bright living areas, well-sized bedrooms, and an updated kitchen with an added pantry for extra storage. Out back, enjoy an attached and enclosed sunroom perfect for

  

  Ashley Spencer

  Keller Williams Commonwealth

  (859) 208-2608

  314 E Broadway St, Winchester, KY 40391
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  Call for Price

  Westwood Apartments - Income Based

  1 - 3 Beds

  900 Westwood Dr, Winchester, KY 40391

  Pick up your application for our WAIT LIST at the office door! Westwood is a charming property in a great location in Winchester, Kentucky with rents based on income. Spacious one, two and three bedroom apartments for rent, each featuring a fully equipped kitchen, your choice of a patio or balcony, and they are wired for cable. Fun in the sun is just a outside your door at our playground, or

  900 Westwood Dr, Winchester, KY 40391
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  $430,000 Sold Jun 16, 2025

  1128 Lafayette Blvd, Winchester, KY 40391

  • 5 Beds
  • 3.5 Baths
  • 3,465 Sq Ft
  • Built 1995

  Last Sold Summary

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

  Current Estimated Value $445,085

  Last Listing Agent Alyssa Ryan Marshall Lane Real Estate - Lexington

  1128 Lafayette Blvd, Winchester, KY 40391
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  /29

  Est $232,841 Not Listed For Sale

  167 E Washington St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,763 Sq Ft
  • Built 1940

  167 E Washington St, Winchester, KY 40391

  Last Sold Summary

  • 8% Above List Price
  • $122/SF
  • 5 Days On Market

  Last Sold Price $215,000

  Last Listing Agent Kymberly McCreary EXP Realty, LLC
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  /22

  $147,000

  • 2 Beds
  • 1 Bath
  • 807 Sq Ft

  3208 Ford Hampton Rd, Winchester, KY 40391

  Escape to a lifestyle defined by the peace and natural beauty of this delightful two bedroom property just steps away from the majestic Kentucky River, this home isn't just a place to iive, it is a dedicated sanctuary whether you are seeking a cozy year round residence or a recreational retreat. One of the standout features is the exceptioal connection to the outdoors with generous porches on

  

  Brenda Sipes

  WEICHERT REALTORS - ABG Properties

  (859) 765-6889

  3208 Ford Hampton Rd, Winchester, KY 40391
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  $1,249 per month

  The Lofts at Winchester! 2 BR, 1 Bath, Off-Street Parking, Small Pets Ok!

  3 Beds

  510 College St, Winchester, KY 40391

  Lovely 2 Bedroom and One Bath Apartment at the Lofts of Winchester, located at 508 College Street, Winchester, KY! Near Downtown, Shopping, Restaurants, Hwy 64 and Hwy 60. Off-street Parking; Small Pets Ok! Beautiful Updated Flooring and Stainless Steel Appliances. Kitchen includes Stove and Refrigerator. Central Heat & AC.Local Schools are: Willis H. Justice Elementary; Robert D.

  510 College St, Winchester, KY 40391
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  $272,000 Sold Jun 26, 2025

  205 Beaumont Place, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft
  • Built 1995

  Last Sold Summary

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

  Current Estimated Value $282,206

  Last Listing Agent Terry Billiter Premier Property Consultants

  205 Beaumont Place, Winchester, KY 40391
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  /12

  Est $78,971 Not Listed For Sale

  123 Magnolia St, Winchester, KY 40391

  • 2 Beds
  • 1,386 Sq Ft
  • Built 1950

  123 Magnolia St, Winchester, KY 40391

  Last Sold Summary

  • 21% Above List Price
  • $47/SF
  • 102 Days On Market

  Last Sold Price $65,000

  Last Listing Agent Shawna Wever Wever Realty LLC
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  $375,000

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft

  4305 Old Boonesboro Rd, Winchester, KY 40391

  

  Brenda Sipes

  WEICHERT REALTORS - ABG Properties

  (859) 549-3072

  4305 Old Boonesboro Rd, Winchester, KY 40391
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  $1,400 per month

  • 3 Beds
  • 2 Baths
  • 1,050 Sq Ft
  • House for Rent

  4971 Old Boonesboro Rd, Winchester, KY 40391

  Property Id: 1661248Welcome to your new home! This stunning 3 bedroom, 2 bathroom single-family manufactured home in Winchester, KY is a must-see. Purchased brand new and placed on farm in 2019, this home features modern amenities such as dishwasher, microwave, washer/dryer hookups, and more. With select utilities included and small dogs allowed(with additional fee), this property won't

  4971 Old Boonesboro Rd, Winchester, KY 40391
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  /75

  $315,000 Sold Jun 27, 2025

  408 Calmes Blvd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,848 Sq Ft
  • Built 1991

  Last Sold Summary

  • 6% Below List Price
  • $170/SF
  • 46 Days On Market

  Current Estimated Value $327,510

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  408 Calmes Blvd, Winchester, KY 40391
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  /16

  Est $189,402 Not Listed For Sale

  142 Spruce Ct, Winchester, KY 40391

  • 4 Beds
  • 1.5 Baths
  • 1,215 Sq Ft
  • Built 1970

  142 Spruce Ct, Winchester, KY 40391

  Last Sold Summary

  • 12% Above List Price
  • $139/SF
  • 406 Days On Market

  Last Sold Price $168,500

  Last Listing Agent Whitney Ensor Ensor Real Estate, LLC
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  /22

  $260,000

  • 4 Beds
  • 2 Baths
  • 2,332 Sq Ft

  35 Cherokee Ct, Winchester, KY 40391

  Step into this 4-bedroom, 2 full bath split-foyer home, perfectly designed for comfortable everyday living. The upper level features three generously sized bedrooms, a full bath, a bright living room, kitchen, and dining area—ideal for gathering with family and friends. Just off the kitchen, enjoy easy access to the covered deck overlooking a spacious backyard. The lower level offers even more

  

  Brenda Rue

  Keller Williams Bluegrass Realty

  (859) 470-8131

  35 Cherokee Ct, Winchester, KY 40391
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  /2

  $1,750 per month

  • 4 Beds
  • 3 Baths
  • 1,450 Sq Ft
  • Condo for Rent

  16 Central Ave Unit A, Winchester, KY 40391

  Experience modern living in this 4-bedroom, 3-bathroom home featuring a bright, open layout, a contemporary kitchen, and comfortable living spaces perfect for families or entertaining. Enjoy stylish finishes, ample storage, and a home designed for convenience and comfort.

  16 Central Ave Unit A, Winchester, KY 40391
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  $302,500 Sold Jan 05, 2026

  202 Dubuy Dr, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,800 Sq Ft
  • Built 2022

  Last Sold Summary

  • 1% Below List Price
  • $168/SF
  • 5 Days On Market

  Current Estimated Value $303,711

  Last Listing Agent Jonne Ursos Keller Williams Bluegrass Realty

  202 Dubuy Dr, Winchester, KY 40391
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  /30

  Est $422,692 Not Listed For Sale

  1186 Lafayette Blvd, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,580 Sq Ft
  • Built 1997

  1186 Lafayette Blvd, Winchester, KY 40391

  Last Sold Summary

  • 11% Above List Price
  • $148/SF
  • 2 Days On Market

  Last Sold Price $382,000

  Last Listing Agent Jason Caudill RE/MAX
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  /29

  $92,000

  • 3 Beds
  • 2 Baths
  • 750 Sq Ft

  113 Mimosa Dr, Winchester, KY 40391

  Discover the perfect balance between home ownership, affordability, and rural tranquility in this charming 3-bedroom two bath home. Conveniently located near shopping areas and interstates providing easy access to Lexington, Winchester and many central Kentucky cities. The interior features freshly updated flooring, offering a cohesive feel to living spaces. The true highlight of this property is

  

  Brenda Sipes

  WEICHERT REALTORS - ABG Properties

  (859) 328-1402

  113 Mimosa Dr, Winchester, KY 40391
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  /31

  $88,500 Sold Aug 08, 2025

  15 Sycamore St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,144 Sq Ft
  • Built 1945

  Last Sold Summary

  • 12% Below List Price
  • $77/SF
  • 28 Days On Market

  Current Estimated Value $108,938

  Last Listing Agent Rony Jo Ballou Power House Realty

  15 Sycamore St, Winchester, KY 40391
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  /26

  Est $259,177 Not Listed For Sale

  636 Laura Dr, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,108 Sq Ft
  • Built 1978

  636 Laura Dr, Winchester, KY 40391

  Last Sold Summary

  • 18% Above List Price
  • $199/SF
  • 3 Days On Market

  Last Sold Price $220,000

  Last Listing Agent Mila Ensor Ensor Real Estate, LLC
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  /36

  $319,900

  • 5 Beds
  • 2 Baths
  • 2,082 Sq Ft

  128 Cherokee Dr, Winchester, KY 40391

  Welcome to 128 Cherokee Drive, a beautifully maintained home in a quiet and desirable neighborhood. With 5 bedrooms, two full bathrooms, and a second living room on the lower floor, there is plenty of room for the entire family and friends. A spacious backyard , many appealing updates since 2022 including a brand new furnace installed in February of 2026, and exceptional curb appeal and charm,

  

  Tyler Hurst

  Thwaites Realtors LLC

  (859) 927-8049

  128 Cherokee Dr, Winchester, KY 40391
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  /35

  $308,000 Sold Oct 03, 2025

  329 Hanover Dr, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,903 Sq Ft
  • Built 2003

  Last Sold Summary

  • 3% Below List Price
  • $162/SF
  • 5 Days On Market

  Current Estimated Value $315,884

  Last Listing Agent Bradley Warford Century 21 Pinnacle

  329 Hanover Dr, Winchester, KY 40391
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  /15

  Est $189,663 Not Listed For Sale

  514 Cs-1383, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 2001

  514 Cs-1383, Winchester, KY 40391

  Last Sold Summary

  • 4% Above List Price
  • $162/SF
  • 5 Days On Market

  Last Sold Price $182,000

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate
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  /38

  $300,000 Pending

  • Land
  • 15.79 Acres
  • $18,999 per Acre

  6261 Ironworks Rd, Winchester, KY 40391

  Opportunity to purchase 15.79 acres offered as three parcels sold together, including 6305 Ironworks Road and 6393 Ironworks Road, providing flexibility for future use. The property includes two mobile homes currently located on the site—one 4 bedroom / 2 bath and one 3 bedroom / 2 bath—which are titled as personal property and may be included in the sale via separate bill of sale, subject to

  

  Kyle McPeck

  Coldwell Banker McMahan

  (859) 376-5596

  6261 Ironworks Rd, Winchester, KY 40391
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  /81

  $599,500 Sold Aug 18, 2025

  2615 Crowe Ridge Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,222 Sq Ft
  • Built 2018

  Last Sold Summary

  • $270/SF
  • 1 Day On Market

  Current Estimated Value $578,572

  Last Listing Agent ROBIN TRIMBLE HomeFirst Real Estate

  2615 Crowe Ridge Rd, Winchester, KY 40391
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  /55

  Est $867,725 Not Listed For Sale

  280 Penny Ln, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,885 Sq Ft
  • Built 2014

  280 Penny Ln, Winchester, KY 40391

  Last Sold Summary

  • 11% Above List Price
  • $272/SF
  • 13 Days On Market

  Last Sold Price $785,000

  Last Listing Agent Nora Williams Keller Williams Commonwealth
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  $354,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,628 Sq Ft

  538 S Maple St, Winchester, KY 40391

  Be the first to call this stunning new construction home! Perfectly situated in the heart of Winchester, this two-story residence offers a fresh, modern feel with convenience at your doorstep. Step inside to discover a bright and airy open-concept main level, featuring durable and stylish Luxury Vinyl Plank (LVP) flooring throughout. The kitchen is a true showstopper, boasting crisp white

  

  Heather Kuykendoll

  Bluegrass Properties Group

  (859) 535-9618

  538 S Maple St, Winchester, KY 40391
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  /70

  $424,900 Sold Jun 02, 2025

  4353 Boonesboro Rd, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,952 Sq Ft
  • Built 1990

  Last Sold Summary

  • 1% Below List Price
  • $144/SF
  • 5 Days On Market

  Last Listing Agent M Gail Cleaver United Real Estate Bluegrass

  4353 Boonesboro Rd, Winchester, KY 40391
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  /70

  Est $288,708 Not Listed For Sale

  705 Oil Springs Rd, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,572 Sq Ft
  • Built 1979

  705 Oil Springs Rd, Winchester, KY 40391

  Last Sold Summary

  • 11% Above List Price
  • $165/SF
  • 35 Days On Market

  Last Sold Price $260,000

  Last Listing Agent Victoria Byrd HomeFirst Real Estate
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  /60

  $299,000

  • 3 Beds
  • 1 Bath
  • 1,273 Sq Ft

  119 Tower Ln, Winchester, KY 40391

  A rare and refined retreat set on five unrestricted acres in Winchester. Privately positioned and surrounded by natural beauty, this renovated berm-style residence offers the perfect balance of seclusion and sophistication. Inside, you'll find thoughtfully curated updates including fresh designer paint, updated flooring, and a bright, inviting interior that feels both modern and timeless. The

  Shawna Wever Wever Realty LLC

  119 Tower Ln, Winchester, KY 40391
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  /35

  $265,000 Sold Jun 18, 2025

  606 Laura Dr, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,240 Sq Ft
  • Built 1974

  Last Sold Summary

  • 7% Below List Price
  • $118/SF
  • 82 Days On Market

  Current Estimated Value $275,624

  Last Listing Agent Bradley Morgan The Local Agents

  606 Laura Dr, Winchester, KY 40391
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  /51

  Est $461,144 Not Listed For Sale

  2051 Kiddville Rd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,654 Sq Ft
  • Built 2001

  2051 Kiddville Rd, Winchester, KY 40391

  Last Sold Summary

  • 7% Below List Price
  • $187/SF
  • 39 Days On Market

  Last Sold Price $495,000

  Last Listing Agent Lindsey Bivens Berkshire Hathaway de Movellan Properties
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  /32

  $259,900

  • 3 Beds
  • 2 Baths
  • 1,251 Sq Ft

  414 Wellington Way, Winchester, KY 40391

  Charming, Move-In Ready Ranch with Updates & Fenced Yard! Welcome home to this super cute and well-maintained 3-bedroom, 2-bath ranch offering easy one-level living and a smart, functional layout. Close to shopping and the interstate for easy commutes. Recent improvements include a brand-new roof, fresh interior paint throughout, a new garage door and opener, and a new stainless-steel appliance

  Amy Diamond ERA Select Real Estate

  414 Wellington Way, Winchester, KY 40391

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