Winchester, KY Homes

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  $372,900

  • 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
• Explore Winchester

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  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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  $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

  Last Listing Agent Brian Lewis Guide Realty, Inc.

  61 Melbourne St, Winchester, KY 40391
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  Est $515,166 Not Listed For Sale

  • 1 Bath

  1026 Crowe Ridge Rd, Winchester, KY 40391

  1026 Crowe Ridge Rd, Winchester, KY 40391
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  $799,999

  • 4 Beds
  • 2.5 Baths
  • 5,290 Sq Ft

  186 Chardonnay Ct, Winchester, KY 40391

  Step into a world of both comfort and convenience with this beautiful 3/4 bedroom, two and one half bath, perfectly designed for relaxation and entertainment. Key features of this property include outdoor spaces to enjoy morning coffee or quiet evening chats. The cozy back porch extends your living space, ideal for dining and enjoying the tranquil surroundings, The beautifully designed patio

  

  Brenda Sipes

  WEICHERT REALTORS - ABG Properties

  (859) 813-4308

  186 Chardonnay Ct, Winchester, KY 40391
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  $1,850 per month

  • 3 Beds
  • 2.5 Baths
  • 1,929 Sq Ft
  • House for Rent

  312 Mcdowell Dr, Winchester, KY 40391

  Well maintained 3 bedroom home with fenced back yard and conveniently located to shopping and the interstate. The home offers beautiful hardwood flooring with an open floor plan, spacious 2 car attached garage, screened in back porch, 1st floor laundry, and large 2nd floor master bedroom. Available for occupancy available 3/1/26. 48 hour notice to show.

  S Ann Wesley Assurance Realty & Property Management

  312 Mcdowell 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 $446,566

  Last Listing Agent Alyssa Ryan Marshall Lane Real Estate - Lexington

  1128 Lafayette Blvd, Winchester, KY 40391
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  Est $239,919 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft

  1112 Ironworks Rd, Winchester, KY 40391

  1112 Ironworks Rd, Winchester, KY 40391
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  $425,000

  • 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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  $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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  $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 $278,824

  Last Listing Agent Terry Billiter Premier Property Consultants

  205 Beaumont Place, Winchester, KY 40391
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  /50

  Est $229,797 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,715 Sq Ft

  122 Sunset Heights, Winchester, KY 40391

  122 Sunset Heights, Winchester, KY 40391
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  $95,000

  • 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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  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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  $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 $325,333

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  408 Calmes Blvd, Winchester, KY 40391
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  /26

  Est $323,076 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,922 Sq Ft

  216 Orchid Ct, Winchester, KY 40391

  216 Orchid Ct, Winchester, KY 40391
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  $319,900

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

  128 Cherokee Dr, Winchester, KY 40391

  **Open House Sunday 11/16 1-3PM** 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, and exceptional curb appeal and charm, this home is just waiting

  

  Tyler Hurst

  Thwaites Realtors LLC

  (859) 681-9697

  128 Cherokee Dr, Winchester, KY 40391
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  /10

  $999 - $1,249 per month

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

  2 - 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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  $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

  Last Listing Agent Jonne Ursos Keller Williams Bluegrass Realty

  202 Dubuy Dr, Winchester, KY 40391
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  Not Listed For Sale

  2292 Athens Boonesboro Rd, Winchester, KY 40391

  2292 Athens Boonesboro Rd, Winchester, KY 40391
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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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  $1,400 per month

  • 3 Beds
  • 1.5 Baths
  • 1,200 Sq Ft
  • Townhouse for Rent

  106 Heather Ln, Winchester, KY 40391

  Clean, spacious, and well maintained 3 bedroom townhome with a large backyard and an oversized garage. Great location!

  106 Heather Ln, 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 $99,902

  Last Listing Agent Rony Jo Ballou Power House Realty

  15 Sycamore St, Winchester, KY 40391
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  /27

  Est $307,899 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft

  2296 Trapp-Goffs Corner Rd, Winchester, KY 40391

  2296 Trapp-Goffs Corner Rd, Winchester, KY 40391
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  $318,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,913 Sq Ft

  22 N Bloomfield Rd, Winchester, KY 40391

  Welcome to this beautiful Craftsman style house on a very large lot, with a beautiful backyard. The newly finished stunning original hardwood floors invite you into the living room and family/dining room. There are two functioning wood burning fireplaces one in the family/dining room and another one in the kitchen. The kitchen is updated with a large island, granite counter tops, stainless steel

  Libby VanMeter Marshall Lane Real Estate - Lexington

  22 N Bloomfield Rd, Winchester, KY 40391
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  /22

  $1,660 per month

  • 3 Beds
  • 1 Bath
  • 1,475 Sq Ft
  • House for Rent

  156 Cook Ave, Winchester, KY 40391

  Highlights: OCCUPIED--DON'T GO TO THE HOUSE. MAKE ARRANGEMENTS WITH MANAGEMENT FOR VIEWING. AVAILABLE December 10th--possibly earlier. The house is 3 bedroom / 1 bathroom. Approximately 1,450 square feet. Rent is $1660 per month. Security deposit is equal to one month's rent. Flooring recently updated. Paint recently updated.

  156 Cook Ave, Winchester, KY 40391
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  $288,300 Sold Jan 31, 2025

  318 Hanover Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,320 Sq Ft
  • Built 2002

  Last Sold Summary

  • $218/SF
  • 2 Days On Market

  Current Estimated Value $292,421

  Last Listing Agent Vickie Skeens RE/MAX Elite Lexington

  318 Hanover Dr, Winchester, KY 40391
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  /51

  Est $483,013 Not Listed For Sale

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

  2051 Kiddville Rd, Winchester, KY 40391

  2051 Kiddville Rd, Winchester, KY 40391
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  /36

  $299,500

  • 4 Beds
  • 2.5 Baths
  • 2,136 Sq Ft

  402 Mcdowell Dr, Winchester, KY 40391

  Welcome home to this meticulously maintained 4-bedroom, 2.5-bathroom residence, where classic charm meets modern luxury. From the moment you step inside, you'll be greeted by the warmth of brand-new laminate hardwood flooring that flows seamlessly throughout the entire home. The spacious split-level layout offers the perfect balance of privacy and togetherness. With four generous bedrooms, there

  Stacey Jones Redfin

  402 Mcdowell Dr, Winchester, KY 40391
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  /7

  $900 per month

  • 2 Beds
  • 1 Bath
  • 840 Sq Ft
  • Townhouse for Rent

  24 White Cir, Winchester, KY 40391

  This very clean and well maintained 2-bedroom, 1-bathroom property at 24 White Circle offers 840 square feet of living space on a quiet cul-de-sac. The living room provides ample room for relaxation and features ceiling fans for comfort. The kitchen is equipped with a dishwasher and includes a washer and dryer for added convenience. The bathroom includes a tub/shower combination. Additional

  24 White Cir, 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 $315,617

  Last Listing Agent Bradley Warford Century 21 Pinnacle

  329 Hanover Dr, Winchester, KY 40391
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  Est $448,224 Not Listed For Sale

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

  1927 Kiddville Rd, Winchester, KY 40391

  1927 Kiddville Rd, Winchester, KY 40391
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  /23

  $498,900

  2996/3056 Irvine Rd, Winchester, KY 40391

  Rare find! Gorgeous 25 acres of gently rolling land with a barn and creek is perfect for building your dream home and creating your homestead! Don't miss this opportunity! This is farm is conveniently located 20 miles from Hamburg and 5 miles from the Winchester bypass. No city sewage. Deed restrictions apply. Relax and enjoy the spectacular views. Get ready to enjoy life! Land consists of 2

  Lura Justice Rector Hayden Realtors

  2996/3056 Irvine Rd, Winchester, KY 40391
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  $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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  Est $699,443 Not Listed For Sale

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

  703 Kiddville Rd, Winchester, KY 40391

  703 Kiddville Rd, Winchester, KY 40391
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  /19

  $499,000

  • Land
  • 36.94 Acres
  • $13,508 per Acre

  1455B Ky-89 Lot Unit Wp001, Winchester, KY 40391

  Don't miss this rare chance to own 36.45 premium acres on the outskirts of Winchesteran unbeatable blend of open farmland, development potential, and a truly top-tier location. Just minutes from I-64 and a quick drive to Lexington, this tract offers the convenience buyers want with the space and freedom they rarely find. The gorgeous rolling fields make this property ideal for farming, hay

  Greg Meade Whitetail Properties Real Estate

  1455B Ky-89 Lot Unit Wp001, 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 $587,948

  Last Listing Agent ROBIN TRIMBLE HomeFirst Real Estate

  2615 Crowe Ridge Rd, Winchester, KY 40391
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  /43

  Est $437,441 Not Listed For Sale

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

  700 Vienna Rd, Winchester, KY 40391

  700 Vienna Rd, Winchester, KY 40391
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  $219,000 Pending

  13015 Irvine Rd, Winchester, KY 40391

  Mendel Tipton Natural Bridge Realty

  13015 Irvine Rd, 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 $272,051

  Last Listing Agent Bradley Morgan The Local Agents

  606 Laura Dr, Winchester, KY 40391

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