Winchester, KY Homes

• 

  

  

  /28

  Est $253,403

  Not Listed For Sale

  116 Alabama St, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,626 Sq Ft
  • Built 1940

  116 Alabama St, Winchester, KY 40391

  Last Sold Summary

  • 95 Days On Market
• 

  

  

  /4

  $169,000

  $10K PRICE DROP Pending

  • 2 Beds
  • 1 Bath
  • 1,472 Sq Ft

  13 Maryland Ave, Winchester, KY 40391

  Welcome Home! Located across the street from a park with walking trails and 2 dog runs, this home is ready for a new owner. Featuring 2 bedrooms on the first floor and an optional 3rd bedroom or bonus room in the partially finished attic space. The original hardwood floors are located throughout the home. VA assumable loan with a 2.99% interest rate - you can't beat that in today's market! Home

  Clay David Sutherland ERA Select Real Estate

  13 Maryland Ave, Winchester, KY 40391
• 

  

  

  /38

  $599,500

  Sold Sep 08, 2025

  102 Bella Shae Way, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,204 Sq Ft
  • Built 2025

  Last Sold Summary

  • $272/SF
  • 72 Days On Market

  Current Estimated Value $596,117

  Last Listing Agent Shane Underwood Keller Williams Commonwealth

  102 Bella Shae Way, Winchester, KY 40391
• 

  

  

  /27

  Est $265,621

  Not Listed For Sale

  335 S Main St, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,968 Sq Ft
  • Built 1920

  335 S Main St, Winchester, KY 40391

  Last Sold Summary

  • 41 Days On Market
• 

  

  

  /26

  $390,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,156 Sq Ft

  178 Hawthorne Dr, Winchester, KY 40391

  Welcome to your Kentucky haven. This charming 3 bedroom, 2.5 bath home has a covered front porch and a partially covered back deck that's perfect for enjoying the Summer outdoors. It's located in a well established neighborhood while only being 8 years old. As you step inside you will love the beautiful hardwood and tile flooring that run throughout the house. A separate mudroom is complete with

  Tiffani Casey Waizenhofer Real Estate

  178 Hawthorne Dr, Winchester, KY 40391
• 

  

  /34

  $333,900

  Sold Jul 28, 2025

  366 Hanover Dr, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,162 Sq Ft
  • Built 2001

  Last Sold Summary

  • $154/SF
  • 2 Days On Market

  Current Estimated Value $345,771

  Last Listing Agent Melissa Brown Keller Williams Legacy Group

  366 Hanover Dr, Winchester, KY 40391
• 

  

  /35

  Est $234,220

  Not Listed For Sale

  24 Hughes Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Built 2024

  24 Hughes Ave, Winchester, KY 40391

  Last Sold Summary

  • 24 Days On Market
• 

  

  /31

  $479,000

  $26K PRICE DROP

  • 8 Beds
  • 4 Baths
  • 5,058 Sq Ft

  265 S Highland St, Winchester, KY 40391

  Great investment opportunity in downtown Winchester! This spacious quadplex has been updated throughout and offers a true turn-key multi-family property. Each unit features two bedrooms, one bathroom, a full kitchen, and its own private laundry area. Utilities are separately metered, allowing tenants to handle their own services and helping keep operating costs manageable. With a total of 8

  J Corey Griffo RE/MAX Elite Lexington

  265 S Highland St, Winchester, KY 40391
• 

  

  /10

  $100,000

  Sold Feb 20, 2026

  17 Waveland Ave, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,061 Sq Ft
  • Built 1950

  Last Sold Summary

  • 9% Below List Price
  • $94/SF
  • 4 Days On Market

  Current Estimated Value $144,813

  Last Listing Agent Darrell Lewis DIY Realty Flat Fee MLS

  17 Waveland Ave, Winchester, KY 40391
• 

  

  /41

  Est $260,893

  Not Listed For Sale

  254 S Highland St, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 3,395 Sq Ft
  • Built 1935

  254 S Highland St, Winchester, KY 40391

  Last Sold Summary

  • 10 Days On Market
• 

  

  /36

  $199,000

  $16K PRICE DROP 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
• 

  

  /37

  $220,000

  Sold Sep 23, 2025

  213 Blair Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,025 Sq Ft
  • Built 1979

  Last Sold Summary

  • 2% Below List Price
  • $215/SF
  • 4 Days On Market

  Current Estimated Value $216,418

  Last Listing Agent Elizabeth Hodge Lifstyl Real Estate

  213 Blair Ave, Winchester, KY 40391
• 

  

  /24

  Est $195,353

  Not Listed For Sale

  54 Winn Ave, Winchester, KY 40391

  • 5 Beds
  • 2 Baths
  • 1,530 Sq Ft
  • Built 1940

  54 Winn Ave, Winchester, KY 40391

  Last Sold Summary

  • 90 Days On Market
• 

  

  /39

  $395,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,883 Sq Ft

  18 Casa Landa Way, Winchester, KY 40391

  Welcome to Winchester living at its finest! Nestled on a spacious .68-acre lot in the desirable Stoney Brook area, this well-maintained brick ranch offers 3 bedrooms, 2 full baths, and approximately 1,883 square feet of comfortable living space. Inside, you'll find a functional floor plan featuring a cozy fireplace, generous living areas, and abundant natural light throughout. The attached

  Steve Charles Freedom Realty & Property Management

  18 Casa Landa Way, Winchester, KY 40391
• 

  

  /33

  $208,000

  Sold May 15, 2026

  59 Holiday Rd, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,050 Sq Ft
  • Built 1985

  Last Sold Summary

  • 1% Below List Price
  • $198/SF
  • 6 Days On Market

  Current Estimated Value $210,586

  Last Listing Agent Kathy Burton Coldwell Banker McMahan

  59 Holiday Rd, Winchester, KY 40391
• 

  

  /33

  Est $251,226

  Not Listed For Sale

  144 E Broadway St, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,544 Sq Ft
  • Built 1930

  144 E Broadway St, Winchester, KY 40391

  Last Sold Summary

  • 119 Days On Market
• 

  

  /6

  $49,500

  • Land
  • 42,688 Sq Ft
  • $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
• 

  

  /14

  $200,000

  Sold Sep 19, 2025

  9711 Ironworks Rd, Winchester, KY 40391

  Last Sold Summary

  • 11% Below List Price
  • 19 Days On Market

  Last Listing Agent Jessica Maloney Denniston Realty

  9711 Ironworks Rd, Winchester, KY 40391
• 

  

  /22

  Est $217,678

  Not Listed For Sale

  44 Buckner St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,309 Sq Ft
  • Built 1935

  44 Buckner St, Winchester, KY 40391

  Last Sold Summary

  • 143 Days On Market
• 

  

  /34

  $237,000

  $38K PRICE DROP

  • Land
  • 6.08 Acres
  • $38,980 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
• 

  

  /75

  $490,000

  Sold Sep 26, 2025

  497 Goose Creek Rd, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 2,972 Sq Ft
  • Built 1993

  Last Sold Summary

  • 1% Below List Price
  • $165/SF
  • 2 Days On Market

  Current Estimated Value $478,787

  Last Listing Agent O Eve Stern Threshold Real Estate Services

  497 Goose Creek Rd, Winchester, KY 40391
• 

  

  /17

  Est $325,644

  Not Listed For Sale

  129 S Highland St, Winchester, KY 40391

  • 6 Beds
  • 4 Baths
  • 3,608 Sq Ft
  • Built 1940

  129 S Highland St, Winchester, KY 40391

  Last Sold Summary

  • 86 Days On Market
• 

  

  /3

  $395,000

  New Construction 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
• 

  

  /25

  $287,000

  Sold Aug 20, 2025

  220 Mcdowell Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,402 Sq Ft
  • Built 1987

  Last Sold Summary

  • 12% Below List Price
  • $205/SF
  • 36 Days On Market

  Current Estimated Value $298,426

  Last Listing Agent Alyssa M Boley Coldwell Banker McMahan

  220 Mcdowell Dr, Winchester, KY 40391
• 

  

  /17

  Est $169,875

  Not Listed For Sale

  21 Franklin Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,006 Sq Ft
  • Built 1940

  21 Franklin Ave, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market
• 

  /2

  $600,000

  • Land
  • 6.13 Acres
  • $97,879 per Acre

  722 Colby Rd Unit 2, Winchester, KY 40391

  Discover an exceptional opportunity for retail investment in the thriving Winchester area. Zoned B-4, this versatile property offers a wide array of possibilities for retail development, providing a strategic location for businesses seeking to establish a prominent presence. With its prime zoning and desirable position within the Winchester area, this property presents a compelling prospect for

  Cheryl Johnston CMI Properties

  722 Colby Rd Unit 2, Winchester, KY 40391
• 

  

  /33

  $240,000

  Sold Sep 10, 2025

  752 Wayland Dr, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,472 Sq Ft
  • Built 1969

  Last Sold Summary

  • 11% Below List Price
  • $97/SF
  • 18 Days On Market

  Current Estimated Value $269,823

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate

  752 Wayland Dr, Winchester, KY 40391
• 

  

  /23

  Est $181,658

  Not Listed For Sale

  353 E Broadway St, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,905 Sq Ft
  • Built 1940

  353 E Broadway St, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market
• 

  

  /9

  $155,000

  $5K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,097 Sq Ft

  220 E Washington St, Winchester, KY 40391

  Charming 3-Bedroom Home with Great Investment Potential....Welcome to this charming 3-bedroom, 1-bath home offering comfortable living space and plenty of opportunity for homeowners or investors alike. Featuring an easy layout with generously sized bedrooms, a large eat-in kitchen, and a bright living area, Outside, you'll find a covered front porch perfect for relaxing, along with a private

  Whitney Ensor Ensor Real Estate, LLC

  220 E Washington St, Winchester, KY 40391
• 

  

  /24

  $275,000

  Sold Mar 02, 2026

  434 Paisley Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,678 Sq Ft
  • Built 2012

  Last Sold Summary

  • $164/SF
  • 1 Day On Market

  Current Estimated Value $275,530

  Last Listing Agent Joshua Davis The Agency

  434 Paisley Ct, Winchester, KY 40391
• 

  

  /53

  Est $130,254

  Not Listed For Sale

  307 Jackson St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,629 Sq Ft
  • Built 1950

  307 Jackson St, Winchester, KY 40391

  Last Sold Summary

  • 67 Days On Market
• 

  

  /40

  $315,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 1,899 Sq Ft

  305 Abbeywood Dr, Winchester, KY 40391

  Welcome to this updated home situated at the end of a cul de sac in desirable Colby Ridge. Updates include new flooring, appliances, paint & more! This adorable home features a first-floor primary suite, utilities on the first floor, a cozy gas fireplace, an eat-in kitchen, formal dining room & a large living room with a vaulted ceiling. Upstairs, you'll find 2 additional bedrooms, a full bath &

  Shevawn Akers Firefly Realty & Investments

  305 Abbeywood Dr, Winchester, KY 40391
• 

  

  /27

  $185,000

  Sold Mar 23, 2026

  616 Boone Ave, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,223 Sq Ft
  • Built 1955

  Last Sold Summary

  • 7% Below List Price
  • $151/SF
  • 16 Days On Market

  Current Estimated Value $189,262

  Last Listing Agent Garnett Davis Tom Goebel & Company

  616 Boone Ave, Winchester, KY 40391
• 

  

  /32

  Est $200,617

  Not Listed For Sale

  230 Winn Ave, Winchester, KY 40391

  • 4 Beds
  • 1.5 Baths
  • 1,400 Sq Ft
  • Built 1940

  230 Winn Ave, Winchester, KY 40391

  Last Sold Summary

  • 73 Days On Market
• 

  

  /21

  $199,900

  Pending

  • 3 Beds
  • 2 Baths
  • 1,140 Sq Ft

  265 Cunningham Ln, Winchester, KY 40391

  (back on the market due to buyers financing) Adventure is always within reach at this property! Located just 35 minutes from Red River Gorge and only 26 minutes from Natural Bridge State Resort Park, this home puts you close to some of Kentucky's most popular outdoor attractions. Spend your weekends hiking scenic trails, canoeing, kayaking, fishing, swimming, riding the sky lift, playing mini

  Kierstin Shaffer Berkshire Hathaway HomeServices Foster Realtors

  265 Cunningham Ln, Winchester, KY 40391
• 

  

  /29

  $262,500

  Sold Feb 18, 2026

  410 Wellington Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,192 Sq Ft
  • Built 2007

  Last Sold Summary

  • 2% Below List Price
  • $220/SF
  • 69 Days On Market

  Current Estimated Value $263,024

  Last Listing Agent Monica Marcum Century 21 Pinnacle

  410 Wellington Way, Winchester, KY 40391
• 

  

  /17

  Est $172,606

  Not Listed For Sale

  30 Rowland Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 956 Sq Ft
  • Built 1952

  30 Rowland Ave, Winchester, KY 40391

  Last Sold Summary

  • 0 Days On Market
• 

  

  /6

  $204,900

  Pending

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

  500 Hidden Hills Way, Winchester, KY 40391

  Ranch with covered porch, new roof, new appliances and countertops, new bath vanity, new professional paint job. Vaulted ceiling in the living room. Clean and ready for occupancy.

  Sondra Clark Taylor Real Estate, LLC

  500 Hidden Hills Way, Winchester, KY 40391
• 

  

  /15

  $241,500

  Sold May 01, 2026

  318 Buffalo Trace, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 2026

  Last Sold Summary

  • 3% Above List Price
  • $201/SF
  • 1 Day On Market

  Current Estimated Value $236,326

  Last Listing Agent Nena Honaker Tom Goebel & Company

  318 Buffalo Trace, Winchester, KY 40391
• 

  

  /20

  Est $206,618

  Not Listed For Sale

  314 E Broadway St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,188 Sq Ft
  • Built 1950

  314 E Broadway St, Winchester, KY 40391

  Last Sold Summary

  • 22 Days On Market

Showing Results 521 - 560, Page 14 of 18