Homes in ZIP Code 40391

• 

  

  

  /41

  Est $248,143

  Not Listed For Sale

  273 Winn Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,982 Sq Ft
  • Built 1880

  273 Winn Ave, Winchester, KY 40391

  Last Sold Summary

  • 38 Days On Market

  Last Listing Agent Nena Honaker Tom Goebel & Company
• 

  

  

  /26

  $234,900

  • 3 Beds
  • 2 Baths
  • 1,904 Sq Ft

  528 Estes Dr, Winchester, KY 40391

  *NEW ROOF!* Welcome home to this well-maintained 3-bedroom, 2-bath brick ranch offering easy one-level living in a convenient location close to shopping, dining, parks, and the community pool. The spacious open family room flows into the kitchen, featuring bamboo wood flooring, a large granite island, newer stainless steel appliances, and a gas range—perfect for everyday living and entertaining.

  Josh Wood Freedom Realty & Property Management

  528 Estes Dr, Winchester, KY 40391
• 

  

  

  /64

  $415,000

  Sold Feb 25, 2026

  1857 Ironworks Rd, Winchester, KY 40391

  • 5 Beds
  • 2.5 Baths
  • 2,924 Sq Ft
  • Built 1865

  Last Sold Summary

  • 3% Below List Price
  • $142/SF
  • 70 Days On Market

  Current Estimated Value $432,875

  Last Listing Agent Meredith Walker Bluegrass Sotheby's International Realty

  1857 Ironworks Rd, Winchester, KY 40391
• 

  

  

  /38

  Est $237,997

  Not Listed For Sale

  113 Mary Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,050 Sq Ft
  • Built 1996

  113 Mary Way, Winchester, KY 40391

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Ashley Spencer Keller Williams Commonwealth
• 

  

  

  /110

  $699,000

  $26K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 4,255 Sq Ft

  132 Lana Ln, Winchester, KY 40391

  MOTIVATED SELLERS. This gorgeous home is a rare find. Perfect for anyone looking for a spacious home with room to grow. The beautiful sunroom overlooks the luxurious in-ground salt water pool. Inside the home you'll find over 4,000 square feet of easy living. A beautiful kitchen with a breakfast nook and bar top, a formal dining area, large living room, a family room with a fireplace, spacious

  Rebecca Harvey Napier Realtors

  132 Lana Ln, Winchester, KY 40391
• 

  

  /47

  $365,000

  Sold Apr 20, 2026

  114 Mallard Ln, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,105 Sq Ft
  • Built 1970

  Last Sold Summary

  • 4% Below List Price
  • $173/SF
  • 162 Days On Market

  Current Estimated Value $364,626

  Last Listing Agent Robin Jones Keller Williams Legacy Group

  114 Mallard Ln, Winchester, KY 40391
• 

  

  /30

  Est $221,396

  Not Listed For Sale

  306 Sarah Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,092 Sq Ft
  • Built 1998

  306 Sarah Ct, Winchester, KY 40391

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Jennifer Rose United Real Estate Bluegrass
• 

  

  /3

  $1,200

  Pending

  • Land
  • 2.57 Acres
  • $467 per Acre

  507 Tech Dr, Winchester, KY 40391

  For lease-Frontage on Rolling Hills Rd, and Tech Drive.I-64 visibility, ideally located commercial property. Paved driveway and gravel lot.$1200 per .25 acre/per month

  Holly Spradlin KY Realty Co

  507 Tech Dr, Winchester, KY 40391
• 

  /2

  $75,000

  Sold Jan 05, 2026

  1341 Sewell Shop Rd, Winchester, KY 40391

  • Land
  • 5.75 Acres
  • $13,043 per Acre

  Last Sold Summary

  • 6% Below List Price
  • 10 Days On Market

  Last Listing Agent Zella Rosenthal Tom Goebel & Company

  1341 Sewell Shop Rd, Winchester, KY 40391
• 

  

  /25

  Est $245,224

  Not Listed For Sale

  316 Jameson Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,625 Sq Ft
  • Built 1990

  316 Jameson Way, Winchester, KY 40391

  Last Sold Summary

  • 140 Days On Market

  Last Listing Agent Jenny Bradley Rector Hayden Realtors
• 

  

  /52

  $419,000

  $46K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,942 Sq Ft

  1024 Flanagan Station Rd, Winchester, KY 40391

  Nestled on 8.9 picturesque acres just off Boonesboro Road, this one-of-a-kind property offers the perfect blend of character, privacy, and endless potential. Whether you're dreaming of a horse farm, hobby farm, or simply room to roam, this beautiful property provides plenty of space for horses, livestock, gardening, or enjoying peaceful country living. Inside, you'll find a spacious open-concept

  Brooke Martin RO&CO Real Estate

  1024 Flanagan Station Rd, Winchester, KY 40391
• 

  /2

  $555,000

  Sold Jan 16, 2026

  184 Casa Landa Way, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 3,585 Sq Ft
  • Built 1998

  Last Sold Summary

  • 6% Below List Price
  • $155/SF

  Current Estimated Value $569,517

  Last Listing Agent Jim Woodrum RE/MAX Creative, Winchester

  184 Casa Landa Way, Winchester, KY 40391
• 

  

  /24

  Est $196,498

  Not Listed For Sale

  605 Dixiana Dr, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,044 Sq Ft
  • Built 1990

  605 Dixiana Dr, Winchester, KY 40391

  Last Sold Summary

  • 23 Days On Market

  Last Listing Agent Dale Hatton Dream Maker Realty, LLC
• 

  

  /30

  $140,000

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 630 Sq Ft

  108 Franklin Ave, Winchester, KY 40391

  Property includes a detached secondary structure, a 600 sq. ft., 1-bedroom, 1-bath. This structure offers potential for investment use. Property and secondary structure are being sold as-is. Buyer and buyer's agent to independently verify square footage, zoning, permitted use, occupancy requirements, and suitability for buyer's intended purpose.

  Cheri Shaffer Lifstyl Real Estate

  108 Franklin Ave, Winchester, KY 40391
• 

  

  /38

  $239,000

  Sold Aug 07, 2026

  210 Shannon Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,164 Sq Ft
  • Built 2003

  Last Sold Summary

  • $205/SF
  • 4 Days On Market

  Current Estimated Value $240,293

  Last Listing Agent ROBIN TRIMBLE HomeFirst Real Estate

  210 Shannon Ct, Winchester, KY 40391
• 

  

  /24

  Est $218,944

  Not Listed For Sale

  502 Corley Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,289 Sq Ft
  • Built 1990

  502 Corley Ln, Winchester, KY 40391

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Pete doCouto Plum Tree Realty
• 

  

  /60

  $235,000

  • 3 Beds
  • 1 Bath
  • 1,272 Sq Ft

  119 Tower Ln, Winchester, KY 40391

  Welcome to 119 Tower Lane! This beautifully remodeled 3-bedroom, 1-bath home offers the perfect combination of modern updates and peaceful country living. Situated on 5 acres, there's plenty of room to enjoy the outdoors, spread out, and make the property your own. Whether you're looking for a move-in-ready home with acreage or a peaceful place to call home, this property is one you won't want to

  Shawna Wever Wever Realty LLC

  119 Tower Ln, Winchester, KY 40391
• 

  

  /30

  $292,000

  Sold Aug 07, 2026

  872 Stratton Ln, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,285 Sq Ft
  • Built 1984

  Last Sold Summary

  • 6% Below List Price
  • $128/SF
  • 15 Days On Market

  Current Estimated Value $309,354

  Last Listing Agent Kathryn Cheuvront Coldwell Banker McMahan

  872 Stratton Ln, Winchester, KY 40391
• 

  

  /87

  Est $279,884

  Not Listed For Sale

  418 Jameson Way, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,680 Sq Ft
  • Built 1996

  418 Jameson Way, Winchester, KY 40391

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Josh Wood Freedom Realty & Property Management
• 

  

  /50

  $249,900

  Pending

  • 3 Beds
  • 1 Bath
  • 1,250 Sq Ft

  215 Robyn Dr, Winchester, KY 40391

  Welcome home to this beautifully updated property offering modern finishes, a functional layout, and a fantastic location! Major improvements include an updated HVAC system, water heater, roof, windows, doors, lighting, flooring, fresh paint and more, giving the next owner plenty to appreciate from day one. Inside, the open kitchen and living area creates an inviting space for everyday living and

  Josh Wood Freedom Realty & Property Management

  215 Robyn Dr, Winchester, KY 40391
• 

  

  /26

  $175,000

  Sold Apr 22, 2026

  10 Pocahontas Trail, Winchester, KY 40391

  • 2 Beds
  • 1.5 Baths
  • 924 Sq Ft
  • Built 1988

  Last Sold Summary

  • $189/SF
  • 7 Days On Market

  Current Estimated Value $182,273

  Last Listing Agent Libby VanMeter Marshall Lane Real Estate - Lexington

  10 Pocahontas Trail, Winchester, KY 40391
• 

  

  /38

  Est $208,536

  Not Listed For Sale

  412 Jameson Way, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,073 Sq Ft
  • Built 1990

  412 Jameson Way, Winchester, KY 40391

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Josh Wood Freedom Realty & Property Management
• 

  

  /15

  $45,000

  • Land
  • 5.59 Acres
  • $8,050 per Acre

  199 Midway Rd, Winchester, KY 40391

  Discover 5.59 acres in Winchester, offering a peaceful setting with just the right amount of seclusion. With city water and electric available at the road, this property offers plenty of potential—whether you're looking to build your dream home or explore an investment opportunity. Enjoy quiet country surroundings while creating a property that fits your vision.

  Skyler Lewis Dream Maker Realty, LLC

  199 Midway Rd, Winchester, KY 40391
• 

  

  /79

  $425,000

  Sold Feb 23, 2026

  1410 Dry Fork Creek Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,064 Sq Ft

  Last Sold Summary

  • 15% Below List Price
  • $399/SF
  • 78 Days On Market

  Last Listing Agent Skyler Lewis Dream Maker Realty, LLC

  1410 Dry Fork Creek Rd, Winchester, KY 40391
• 

  

  /14

  Est $200,025

  Not Listed For Sale

  411 Jameson Way, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Built 1990

  411 Jameson Way, Winchester, KY 40391

  Last Sold Summary

  • 19 Days On Market

  Last Listing Agent Jason Szaks EXIT Town & Country Realtors
• 

  

  /74

  $489,000

  Pending

  • 4 Beds
  • 3.5 Baths
  • 3,584 Sq Ft

  1137 Lafayette Blvd, Winchester, KY 40391

  Welcome home to this 4 bedroom, 3.5 bathroom home offering plenty of room to spread out. The open kitchen and living room create a comfortable gathering space, while a separate dining room provides additional space for meals and entertaining. The fully finished basement offers even more living space, including a room with a closet that could provide flexibility for a home office, hobby room or

  Brittany Nester RO&CO Real Estate

  1137 Lafayette Blvd, Winchester, KY 40391
• 

  

  /53

  $268,000

  Sold Jul 31, 2026

  311 Geronimo Ct, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 1,510 Sq Ft
  • Built 1999

  Last Sold Summary

  • $177/SF
  • 14 Days On Market

  Current Estimated Value $266,709

  Last Listing Agent Brenda Sipes WEICHERT REALTORS - ABG Properties

  311 Geronimo Ct, Winchester, KY 40391
• 

  

  /33

  Est $299,895

  Not Listed For Sale

  137 Summerhill Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,284 Sq Ft
  • Built 2003

  137 Summerhill Way, Winchester, KY 40391

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Keith Wilson Coldwell Banker McMahan
• 

  

  /29

  $80,000

  $30K PRICE INCREASE

  • 1 Bed
  • 1 Bath
  • 870 Sq Ft

  141 Coffee Springs Ln, Winchester, KY 40391

  Tucked away in a peaceful wooded setting, close to the Kentucky River, this unique property offers privacy, natural beauty, and plenty of potential. The rustic cabin is surrounded by mature trees, native stone, impressive rock formations, and remnants of old stonework that give the property a one-of-a-kind character. Loft bedroom 1 bath Cabin. This property would be great for fisherman or a

  Rony Jo Ballou Power House Realty

  141 Coffee Springs Ln, Winchester, KY 40391
• 

  

  /24

  $188,000

  Sold Jan 29, 2026

  27 Ashland Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,653 Sq Ft
  • Built 1950

  Last Sold Summary

  • 6% Below List Price
  • $114/SF
  • 112 Days On Market

  Current Estimated Value $189,369

  Last Listing Agent Robin Mobley-Mosher Marshall Lane Real Estate - Lexington

  27 Ashland Ave, Winchester, KY 40391
• 

  

  /31

  Est $248,323

  Not Listed For Sale

  121 Summerhill Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,302 Sq Ft
  • Built 2002

  121 Summerhill Way, Winchester, KY 40391

  Last Sold Summary

  • 70 Days On Market

  Last Listing Agent Pete doCouto Plum Tree Realty
• 

  /2

  $100,000

  $10K PRICE DROP

  • Land
  • 13,939 Sq Ft
  • $312,500 per Acre

  111 Jacob Ct, Winchester, KY 40391

  Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

  John Wilson Bluegrass Properties Group

  111 Jacob Ct, Winchester, KY 40391
• 

  

  /23

  $325,000

  Sold Sep 14, 2026

  225 Plantations Dr, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 3,868 Sq Ft
  • Built 2000

  Last Sold Summary

  • 12% Below List Price
  • $84/SF
  • 183 Days On Market

  Current Estimated Value $330,908

  Last Listing Agent John Wilson Bluegrass Properties Group

  225 Plantations Dr, Winchester, KY 40391
• 

  

  /23

  Est $279,627

  Not Listed For Sale

  302 Salem Ave, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,490 Sq Ft
  • Built 2001

  302 Salem Ave, Winchester, KY 40391

  Last Sold Summary

  • 34 Days On Market

  Last Listing Agent Emily Donaldson Keller Williams Commonwealth
• 

  

  /3

  $42,500

  • Land
  • 8,712 Sq Ft
  • $212,500 per Acre

  108 Dorset Ln, Winchester, KY 40391

  The restictions state that if it is a ranch plan, there is a minimun of 1300 sq ft. It it is a 1 1/2 story or two story then 1800 sq ft will be required. A two car garage must be attached. Developer will need to approve plans before starting construction This lot is ideal for a walkout basement. Perfect setting for watching the sunsets

  Jo Gawthrop Keller Williams Bluegrass Realty

  108 Dorset Ln, Winchester, KY 40391
• 

  

  /52

  $448,000

  Sold Jul 10, 2026

  207 Hibiscus Ln, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 3,126 Sq Ft
  • Built 1999

  Last Sold Summary

  • $143/SF
  • 2 Days On Market

  Current Estimated Value $446,671

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

  207 Hibiscus Ln, Winchester, KY 40391
• 

  

  /17

  Est $282,326

  Not Listed For Sale

  218 Bracken Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,292 Sq Ft
  • Built 2005

  218 Bracken Ct, Winchester, KY 40391

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Vickie Skeens RE/MAX Elite Lexington
• 

  

  /18

  $169,000

  $10K PRICE DROP Pending

  • 3 Beds
  • 1 Bath
  • 1,046 Sq Ft

  175 Magnolia St, Winchester, KY 40391

  Newly renovated and move-in ready! This charming 3-bedroom, 1-bath home features 1,046 sq. ft. of living space along with a large storage shed in the fenced in backyard.

  A. Rebecca Woods Woods Realty Group

  175 Magnolia St, Winchester, KY 40391
• 

  

  /62

  $453,200

  Sold Jul 23, 2026

  1661 Waterworks Rd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,793 Sq Ft
  • Built 1983

  Last Sold Summary

  • 6% Above List Price
  • $162/SF
  • 3 Days On Market

  Current Estimated Value $447,748

  Last Listing Agent Jim Woodrum RE/MAX Creative, Winchester

  1661 Waterworks Rd, Winchester, KY 40391
• 

  

  /32

  Est $263,856

  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

  • 3 Days On Market

  Last Listing Agent Amy Diamond ERA Select Real Estate

Showing Results 361 - 400, Page 10 of 18