Homes in ZIP Code 40391

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  /47

  $365,000 Pending

  • 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
• 

  

  

  /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
• 

  

  

  /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 $52,699

  Last Listing Agent Brian Lewis Guide Realty, Inc.

  61 Melbourne St, Winchester, KY 40391
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  /32

  Est $240,964 Not Listed For Sale

  200 Bracken Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,252 Sq Ft
  • Built 2002

  200 Bracken Ct, Winchester, KY 40391

  Last Sold Summary

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

  Last Sold Price $230,000

  Last Listing Agent Amy Diamond ERA Select Real Estate
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  /37

  $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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  /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
• 

  

  /32

  Est $231,869 Not Listed For Sale

  162 French Ave, Winchester, KY 40391

  • 4 Beds
  • 1 Bath
  • 2,327 Sq Ft
  • Built 1920

  162 French Ave, Winchester, KY 40391

  Last Sold Summary

  • 18% Above List Price
  • $84/SF
  • 15 Days On Market

  Last Sold Price $195,700

  Last Listing Agent Dale Hatton Dream Maker Realty, LLC
• 

  

  /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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  /20

  $749 - $899 per month

  Studio 28 Apartments

  Studio - 1 Bed

  27 E Washington St, Winchester, KY 40391

  *One Month Free Rent!* All Utilities Included! Nice Studio Apt Near Downtown Winchester!Marketing DescriptionStudio Apartment Available at Studio 29 Apartments, Winchester, KY! One Bath; Only 5 Minutes from Downtown! Off-Street Parking, Small Pets Ok; All Utilities Included! Kitchen includes a Stove, Refrigerator, and Microwave; Non-smoking.Conveniently located near Shopping, Grocery

  27 E Washington St, Winchester, KY 40391
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  /43

  $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 $454,295

  Last Listing Agent Alyssa Ryan Marshall Lane Real Estate - Lexington

  1128 Lafayette Blvd, Winchester, KY 40391
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  /51

  Est $318,951 Not Listed For Sale

  28 Edgewood Dr, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 1,962 Sq Ft
  • Built 1984

  28 Edgewood Dr, Winchester, KY 40391

  Last Sold Summary

  • 10% Above List Price
  • $148/SF
  • 11 Days On Market

  Last Sold Price $290,000

  Last Listing Agent Robin Jones Keller Williams Legacy Group
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  /32

  $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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  /9

  $1,249 per month

  Lofts of Winchester

  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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  /41

  $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 $286,307

  Last Listing Agent Terry Billiter Premier Property Consultants

  205 Beaumont Place, Winchester, KY 40391
• 

  

  /23

  Est $223,187 Not Listed For Sale

  112 Quail Ridge Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,450 Sq Ft
  • Built 1994

  112 Quail Ridge Rd, Winchester, KY 40391

  Last Sold Summary

  • 14% Above List Price
  • $135/SF
  • 114 Days On Market

  Last Sold Price $196,400

  Last Listing Agent Destiny Darby Keller Williams Commonwealth
• 

  

  /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

  $1,295 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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  /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 $329,049

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  408 Calmes Blvd, Winchester, KY 40391
• 

  

  /34

  Est $350,778 Not Listed For Sale

  421 Skylark Dr, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 1,950 Sq Ft
  • Built 1992

  421 Skylark Dr, Winchester, KY 40391

  Last Sold Summary

  • 17% Above List Price
  • $154/SF
  • 45 Days On Market

  Last Sold Price $300,000

  Last Listing Agent Alyssa M Boley Coldwell Banker McMahan
• 

  

  /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
• 

  

  /10

  $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
• 

  

  /41

  $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 $303,140

  Last Listing Agent Jonne Ursos Keller Williams Bluegrass Realty

  202 Dubuy Dr, Winchester, KY 40391
• 

  

  /18

  Est $286,932 Not Listed For Sale

  110 Buckingham Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,240 Sq Ft
  • Built 2001

  110 Buckingham Ln, Winchester, KY 40391

  Last Sold Summary

  • 20% Above List Price
  • $194/SF
  • 8 Days On Market

  Last Sold Price $240,000

  Last Listing Agent Jonathan Wood HomeLand Real Estate Inc - Mt Sterling
• 

  

  /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
• 

  /2

  $1,595 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
• 

  

  /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 $105,431

  Last Listing Agent Rony Jo Ballou Power House Realty

  15 Sycamore St, Winchester, KY 40391
• 

  

  /49

  Est $120,847 Not Listed For Sale

  133 Settlers Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,564 Sq Ft
  • Built 1940

  133 Settlers Ln, Winchester, KY 40391

  Last Sold Summary

  • 29% Above List Price
  • $37/SF
  • 194 Days On Market

  Last Sold Price $94,000

  Last Listing Agent Kimberly Brunson Hunter Real Estate
• 

  

  /32

  $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
• 

  /2

  $1,695 per month

  • 3 Beds
  • 2 Baths
  • Condo for Rent

  117 Linden Ave Unit A, Winchester, KY 40391

  Discover comfortable and affordable living in this spacious 3-bedroom, 1-bathroom apartment with gas and water included in rent. The home features bright and inviting interiors with plenty of natural light, offering a warm and welcoming atmosphere for you and your family.Designed with convenience in mind, this unit provides ample living space, functional layouts, and easy access to nearby

  117 Linden Ave Unit A, Winchester, KY 40391
• 

  

  /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 $268,900

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

  2721 Pretty Run Rd, Winchester, KY 40391
• 

  

  /63

  Est $708,830 Not Listed For Sale

  291 Sundown Ln, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,356 Sq Ft
  • Built 2004

  291 Sundown Ln, Winchester, KY 40391

  Last Sold Summary

  • 15% Above List Price
  • $261/SF
  • 0 Days On Market

  Last Sold Price $616,000

  Last Listing Agent Maxine Reyburn RO&CO Real Estate
• 

  

  /92

  $1,750,000

  • 8 Beds
  • 9 Baths
  • 10,825 Sq Ft

  131 Wells Rd, Mount Sterling, KY 40353

  A rare opportunity to own an architecturally stunning custom estate on approximately 35 acres with two private entrances. Designed for beauty, function, privacy, and accessibility, this one of a kind residence offers craftsmanship and scale rarely seen in today's market. At the heart of the home is a breathtaking approximately 1,200 square foot central atrium surrounded by nearly every living

  Terra Long Keller Williams Commonwealth

  131 Wells Rd, Mount Sterling, KY 40353
• 

  

  /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
• 

  

  /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 $309,837

  Last Listing Agent Bradley Warford Century 21 Pinnacle

  329 Hanover Dr, Winchester, KY 40391
• 

  

  /3

  Est $179,776 Not Listed For Sale

  785 Ecton Rd, Winchester, KY 40391

  785 Ecton Rd, Winchester, KY 40391

  Last Sold Summary

  • 9% Above List Price
  • 579 Days On Market

  Last Sold Price $165,000

  Last Listing Agent Lara Thornbury Block + Lot Real Estate
• 

  

  /59

  $294,000

  • 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
• 

  

  /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
• 

  

  /6

  Est $57,247 Not Listed For Sale

  221 Ashton Oak Way, Winchester, KY 40391

  221 Ashton Oak Way, Winchester, KY 40391

  Last Sold Summary

  • 14% Above List Price
  • 264 Days On Market

  Last Sold Price $50,000

  Last Listing Agent Melia Hord Keller Williams Legacy Group
• 

  

  /35

  $360,900 New Construction

  • 3 - 4 Beds
  • 2.5 - 3.5 Baths
  • 1,828 Sq Ft

  Grace Plan at Boone's Crossing, Winchester, KY 40391

  Welcome to the Grace plan, where the art of harmonious living comes to life, striking the perfect balance between spacious living areas on the first floor and cozy bedrooms on the second. As you approach, take in the captivating exterior options, where you have the power to choose between a Farmhouse, French Country, or Cottage facade, ensuring your home is a reflection of your unique style.Upon

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 39824257, Winchester, KY 40391

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