Winchester, KY Homes

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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
• Explore Winchester

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  Starting at $800 Per Month

  • 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

  Summit Apartments

  (859) 577-9164

  260 Oxford Dr, Winchester, KY 40391
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  $15,000 Sold Dec 30, 2025

  61 Melbourne St, Winchester, KY 40391

  • Land
  • 4,356 Sq Ft
  • $150,000 per Acre

  Last Sold Summary

  • 40% Below List Price
  • 57 Days On Market

  Current Estimated Value $49,546

  Last Listing Agent Brian Lewis Guide Realty, Inc.

  61 Melbourne St, Winchester, KY 40391
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  /22

  Est $133,296 Not Listed For Sale

  423 E Broadway St, Winchester, KY 40391

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

  423 E Broadway St, Winchester, KY 40391

  Last Sold Summary

  • 51% Above List Price
  • $37/SF
  • 23 Days On Market

  • Last Sold Price $88,000
  • May 08, 2025

  Last Listing Agent Tanya McKee Bluegrass Auction, Appraisal & Realty, LLC
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  $550,000

  • 5 Beds
  • 3 Baths
  • 3,102 Sq Ft

  110 White Conkwright Rd, Winchester, KY 40391

  Brick ranch with 3 upstairs bedrooms and 2 bedrooms in your mother in law suite and full finished basement, complete with kitchen. 2 gazebos with one attached to walk out porch over looking almost 3 acres of beautiful land. Attached 2 car garage and detached 2 car garage. Barn/workshop included, along with another metal building for storage.

  

  Philip 'PJ' Elder

  Omega Real Estate Brokerage LLC

  (859) 695-3879

  110 White Conkwright Rd, Winchester, KY 40391
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  /2

  $1,095 Per Month

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft
  • Condo for Rent

  1028 W Lexington Ave Unit 3, Winchester, KY 40391

  This cozy 1-bedroom, 1-bathroom apartment features a comfortable living area and a functional kitchen. Pets are welcome with an additional pet fee. Tenants are responsible for all utility payments, giving you full control over your monthly expenses. Ideal for anyone seeking a convenient and pet-friendly home.

  1028 W Lexington Ave Unit 3, Winchester, KY 40391
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  $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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  /16

  Est $264,258 Not Listed For Sale

  13385 Ironworks Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,350 Sq Ft
  • Built 1980

  13385 Ironworks Rd, Winchester, KY 40391

  Last Sold Summary

  • 10% Above List Price
  • $178/SF
  • 4 Days On Market

  • Last Sold Price $240,000
  • Apr 15, 2025

  Last Listing Agent Joshua Davis The Agency
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  $749,999

  • 4 Beds
  • 2.5 Baths
  • 7,058 Sq Ft

  186 Chardonnay Ct, Winchester, KY 40391

  Fontaine Estates, a great place to call home. This spacious 4 bedroom 3 bath property offers an abundance of storage,, including charming window seats. Enjoy the convenience of an oversized driveway and garage, along with a beautifully designed outdoor setting, feauring a fire pit and a dedicated entertainment space. The thoughtfully planned, custom designed landscaping enhances the home's curb

  

  Brenda Sipes

  WEICHERT REALTORS - ABG Properties

  (859) 470-2071

  186 Chardonnay Ct, Winchester, KY 40391
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  $1,370 Per Month

  • 2 Beds
  • 1 Bath
  • 1,400 Sq Ft
  • Condo for Rent

  204 S Maple St Unit 204 S Maple, Winchester, KY 40391

  This charming 2-bedroom, 1-bathroom apartment features a comfortable living room and a functional kitchen. Rent includes the municipal water bill, while tenants are responsible for gas and electricity. Perfect for anyone seeking an affordable, move-in ready home with essential amenities.

  204 S Maple St Unit 204 S Maple, 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 $457,550

  Last Listing Agent Alyssa Ryan Marshall Lane Real Estate - Lexington

  1128 Lafayette Blvd, Winchester, KY 40391
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  /70

  Est $307,579 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

  • 18% Above List Price
  • $165/SF
  • 35 Days On Market

  • Last Sold Price $260,000
  • Feb 10, 2025

  Last Listing Agent Victoria Byrd HomeFirst Real Estate
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  $185,900

  • 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

  (859) 695-6124

  41 7th St, Winchester, KY 40391
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  $1,800 Per Month

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Condo for Rent

  135 Winn Ave Unit A, Winchester, KY 40391

  Step into this beautifully renovated 3-bedroom, 2-bathroom home featuring a bright and open living area and a modern kitchen on the ground floor. Designed for comfort and style, this residence offers contemporary finishes, spacious layouts, and all the amenities you need for modern living. Perfect for families or anyone seeking a move-in ready home with a fresh, modern feel.

  135 Winn Ave Unit A, 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 $289,600

  Last Listing Agent Terry Billiter Premier Property Consultants

  205 Beaumont Place, Winchester, KY 40391
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  /51

  Est $471,101 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

  • 5% Below List Price
  • $187/SF
  • 39 Days On Market

  • Last Sold Price $495,000
  • Jul 07, 2023

  Last Listing Agent Lindsey Bivens Berkshire Hathaway de Movellan Properties
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  /22

  $255,000 Pending

  • 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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  $950

  Total Monthly Price

  • 1 Bed
  • 1 Bath
  • 912 Sq Ft
  • Condo for Rent

  127 S Highland St Unit 2, Winchester, KY 40391

  1 Bed 1 Bath with living room and kitchen. Was previously rented as a 2 Bed 1 bath without living room.

  127 S Highland St Unit 2, Winchester, KY 40391
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  $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 $327,174

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  408 Calmes Blvd, Winchester, KY 40391
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  /44

  Est $422,420 Not Listed For Sale

  1927 Kiddville Rd, Winchester, KY 40391

  • 5 Beds
  • 4 Baths
  • 2,056 Sq Ft
  • Built 2001

  1927 Kiddville Rd, Winchester, KY 40391

  Last Sold Summary

  • 9% Below List Price
  • $226/SF
  • 22 Days On Market

  • Last Sold Price $465,000
  • Oct 06, 2023

  Last Listing Agent Megan McCoy Keller Williams Legacy Group
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  /29

  $70,000

  • 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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  $1,500

  Total Monthly Price

  • 3 Beds
  • 1 Bath
  • 1,600 Sq Ft
  • House for Rent

  16 Hughes Ave, Winchester, KY 40391

  Newly updated spacious 2 bedrooms 1 bath on main level and 1 bedroom on lower lever with a family room. Laundry and storage on the lower level. Huge backyard is not fenced. New kitchen cabinets and new flooring and paint throughout. New concrete porch. Tenants pay electric and water. 1 small dog permitted with breed restrictions. $375 pet fee. Cats are not permitted. Submit an application.

  16 Hughes Ave, 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 $302,611

  Last Listing Agent Jonne Ursos Keller Williams Bluegrass Realty

  202 Dubuy Dr, Winchester, KY 40391
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  Est $436,971 Not Listed For Sale

  372 Arrowhead Ln, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,744 Sq Ft
  • Built 2001

  372 Arrowhead Ln, Winchester, KY 40391

  Last Sold Summary

  • 17% Above List Price
  • $137/SF
  • 2 Days On Market

  • Last Sold Price $375,000
  • Mar 07, 2025

  Last Listing Agent Lori Tolson Lifstyl Real Estate
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  $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, new insulation and baffling, and

  

  Tyler Hurst

  Thwaites Realtors LLC

  (859) 927-8049

  128 Cherokee Dr, Winchester, KY 40391
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  /8

  $925 Per Month

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft
  • 151/153 WPI

  151-153 Westside Dr Unit 151 Westside Drive, Winchester, KY 40391

  151-153 Westside Dr Unit 151 Westside Drive, Winchester, KY 40391
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  $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 $97,942

  Last Listing Agent Rony Jo Ballou Power House Realty

  15 Sycamore St, Winchester, KY 40391
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  Est $706,014 Not Listed For Sale

  703 Kiddville Rd, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 2,311 Sq Ft
  • Built 1980

  703 Kiddville Rd, Winchester, KY 40391

  Last Sold Summary

  • 1% Above List Price
  • $303/SF
  • 276 Days On Market

  • Last Sold Price $699,900
  • May 09, 2024

  Last Listing Agent Tyson Walters Kassie & Associates
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  $775,000

  • 5 Beds
  • 3 Baths
  • 4,437 Sq Ft

  465 Morris Rd, Winchester, KY 40391

  Dreaming of wide-open spaces and country charm? This beautiful 16-acre property in Clark County offers the perfect blend of comfort and functionality. The stately brick home provides generous living space with classic appeal, offering endless potential. With five bedrooms and three full baths, the home accommodates a variety of living arrangements, whether you need space for guests, a home

  

  Brenda Leigh Walters

  United Real Estate Bluegrass

  (859) 459-0504

  465 Morris Rd, Winchester, KY 40391
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  $1,125 Per Month

  • 2 Beds
  • 2.5 Baths
  • 1,100 Sq Ft
  • Condo for Rent

  367 Colby Ridge Blvd Unit 367 colby, Winchester, KY 40391

  367 Colby Ridge Blvd Unit 367 colby, Winchester, KY 40391
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  /30

  $190,000 Sold Mar 06, 2026

  2721 Pretty Run Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft
  • Built 2000

  Last Sold Summary

  • 37% Below List Price
  • $130/SF
  • 12 Days On Market

  Current Estimated Value $269,027

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

  2721 Pretty Run Rd, Winchester, KY 40391
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  Est $411,000 Not Listed For Sale

  700 Vienna Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,826 Sq Ft
  • Built 2004

  700 Vienna Rd, Winchester, KY 40391

  Last Sold Summary

  • 26% Above List Price
  • $178/SF
  • 18 Days On Market

  • Last Sold Price $325,000
  • Aug 10, 2023

  Last Listing Agent Sheridan Sims Keller Williams Commonwealth
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  /22

  $139,000

  • 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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  $995 Per Month

  • 2 Beds
  • 1 Bath
  • Condo for Rent

  265 S Highland St Unit 4, Winchester, KY 40391

  Welcome to our charming apartment in Winchester, KY! This apartment boasts beautiful wood floors throughout, creating a warm and inviting atmosphere. Enjoy the convenience of a large yard and an in-unit laundry room. Located close to downtown and shopping, you'll have easy access to all the amenities Winchester has to offer. Don't miss out on the opportunity to call this unique apartment

  265 S Highland St Unit 4, Winchester, KY 40391
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  $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 $311,675

  Last Listing Agent Bradley Warford Century 21 Pinnacle

  329 Hanover Dr, Winchester, KY 40391
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  /96

  Est $423,596 Not Listed For Sale

  2430 Log Lick Rd, Winchester, KY 40391

  • 5 Beds
  • 3 Baths
  • 2,700 Sq Ft
  • Built 1938

  2430 Log Lick Rd, Winchester, KY 40391

  Last Sold Summary

  • 5% Above List Price
  • $150/SF
  • 184 Days On Market

  • Last Sold Price $405,000
  • Jun 07, 2024

  Last Listing Agent E Anthony Phillips RE/MAX
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  $349,900 Pending

  • 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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  $850 Per Month

  • 2 Beds
  • 2 Baths
  • 980 Sq Ft
  • 2 Bedroom, 2 Bath Mobile Home in Yorktowne, Winchester!

  210 Cr-1327, Winchester, KY 40391

  Come check out this 2 bedroom, 2 bath mobile home in Yorktowne! Well maintained & clean. Private driveway, in unit laundry, large kitchen & living room area, storage shed and more! Residents Pay Electric & Reimburse Landlord for Water Usage each month. $775/month, $775 DepositUp to 2 Small Dogs Permitted with additional fees.

  210 Cr-1327, Winchester, KY 40391
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  $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 $582,767

  Last Listing Agent ROBIN TRIMBLE HomeFirst Real Estate

  2615 Crowe Ridge Rd, Winchester, KY 40391
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  Est $240,180 Not Listed For Sale

  3604 Pine Ridge Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,280 Sq Ft
  • Built 1998

  3604 Pine Ridge Rd, Winchester, KY 40391

  Last Sold Summary

  • 50% Above List Price
  • $125/SF
  • 3 Days On Market

  • Last Sold Price $160,000
  • Jul 03, 2024

  Last Listing Agent Patty Adams Rector Hayden Realtors

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