Homes in ZIP Code 40391

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  /2

  $85,000 Sold Dec 12, 2025

  1385 Sewell Shop Rd, Winchester, KY 40391

  • Land
  • 6.43 Acres
  • $13,219 per Acre

  Last Sold Summary

  • 6% Below List Price
  • 6 Days On Market

  Last Listing Agent Zella Rosenthal Tom Goebel & Company

  1385 Sewell Shop Rd, Winchester, KY 40391
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  /17

  Est $172,181 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

  • 36% Above List Price
  • $133/SF
  • 0 Days On Market

  Last Sold Price $127,000

  Last Listing Agent Lyndsey Ryles Kentucky Elite Real Estate
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  /4

  $67,500

  • Land
  • 1.92 Acres
  • $35,156 per Acre

  12569 Ironworks Rd, Winchester, KY 40391

  Build your dream home in the stunning ESKIPPAKITHIKI OVERLOOKS! Or hold as investment property and watch this land grow in value. This lot containing 1.919 acres, offer unparalleled views of a serene, natural setting. Perfect for a private retreat or family estate, this property invites you to design your ideal lifestyle surrounded by the beauty and tranquility. Don't miss your opportunity to own

  Kathryn Cheuvront Coldwell Banker McMahan

  12569 Ironworks Rd, Winchester, KY 40391
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  /53

  $867,500 Sold Aug 01, 2025

  511 Boone Ave, Winchester, KY 40391

  • 4 Beds
  • 4.5 Baths
  • 4,698 Sq Ft
  • Built 1885

  Last Sold Summary

  • 11% Below List Price
  • $185/SF
  • 318 Days On Market

  Current Estimated Value $908,797

  Last Listing Agent Greg Leveridge Block + Lot Real Estate

  511 Boone Ave, Winchester, KY 40391
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  /20

  Est $214,486 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

  • 13% Above List Price
  • $160/SF
  • 22 Days On Market

  Last Sold Price $190,000

  Last Listing Agent Ashley Spencer Keller Williams Commonwealth
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  /3

  $825,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,995 Sq Ft

  111 Bella Shae Way, Winchester, KY 40391

  Welcome Home to the Park Place Floor Plan by CP Builders. This elegant ranch home features all-brick construction and a thoughtfully designed split bedroom layout for maximum privacy. The open floor plan seamlessly connects the living, dining, and kitchen areas, creating a warm and inviting atmosphere. Thespacious kitchen is a chef's dream, boasting a large island, a convenient pantry, and a

  Shane Underwood Keller Williams Commonwealth

  111 Bella Shae Way, Winchester, KY 40391
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  /36

  $420,000 Sold Feb 25, 2026

  134 Fontaine Blvd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,747 Sq Ft
  • Built 1994

  Last Sold Summary

  • 7% Below List Price
  • $153/SF
  • 126 Days On Market

  Current Estimated Value $421,734

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate

  134 Fontaine Blvd, Winchester, KY 40391
• 

  

  /27

  Est $187,873 Not Listed For Sale

  37 Jackson St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,400 Sq Ft
  • Built 1940

  37 Jackson St, Winchester, KY 40391

  Last Sold Summary

  • 16% Above List Price
  • $116/SF
  • 30 Days On Market

  Last Sold Price $162,000

  Last Listing Agent O. Debbie Pennington CENTURY 21 Advantage Realty
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  /68

  $2,450,000

  • 5 Beds
  • 5 Baths
  • 6,284 Sq Ft

  5039 Combs Ferry Rd, Ford, KY 40391

  This 5 Bedroom, 5 Bathroom home is quietly located in the highly desired Combs Ferry area of Clark County. Location is evident as you are approximately an 8-minute drive to Hamburg as well as 8-minute drive to downtown Winchester. This complete custom home was constructed in 2022. The 6284 sqft boasts custom features including built in appliances, in-ground oversized heated pool with outdoor

  Michael Hilario The Agency

  5039 Combs Ferry Rd, Ford, KY 40391
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  /41

  $310,000 Sold Dec 29, 2025

  1996 White Conkwright Rd, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,055 Sq Ft
  • Built 1966

  Last Sold Summary

  • 9% Below List Price
  • $294/SF
  • 45 Days On Market

  Current Estimated Value $320,605

  Last Listing Agent Lucy Martin Jenkins United Real Estate Bluegrass

  1996 White Conkwright Rd, Winchester, KY 40391
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  /43

  Est $144,485 Not Listed For Sale

  116 Park Ave, Winchester, KY 40391

  • 1 Bed
  • 1 Bath
  • 1,576 Sq Ft
  • Built 1940

  116 Park Ave, Winchester, KY 40391

  Last Sold Summary

  • 33% Above List Price
  • $69/SF
  • 23 Days On Market

  Last Sold Price $108,500

  Last Listing Agent Christa Joynt Keller Williams Commonwealth
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  /4

  $225,000

  • Land
  • 8.09 Acres
  • $27,812 per Acre

  2110 Athens Boonesboro Rd, Ford, KY 40391

  Prime building lot - 8.092 acres ready for your new dream home! Come pick your dream lot and enjoy the great views of the countryside and farmland. Rural living with the convenience of being just 15-20 minutes away from Lexington, Winchester and the interstate (I-75). 2110 approved for its own entrance. Multiple lots to choose from ranging from 4-8 acres +/-. Call today to get the first choice on

  Megan McCoy Keller Williams Legacy Group

  2110 Athens Boonesboro Rd, Ford, KY 40391
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  /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 $584,967

  Last Listing Agent Shane Underwood Keller Williams Commonwealth

  102 Bella Shae Way, Winchester, KY 40391
• 

  

  /19

  Est $164,963 Not Listed For Sale

  Unlisted Address

  • 3 Beds
  • 1 Bath
  • 1,683 Sq Ft
  • Built 2023

  Unlisted Address

  Last Sold Summary

  • 41% Above List Price
  • $70/SF
  • 6 Days On Market

  Last Sold Price $117,000

  Last Listing Agent Darrell Lewis DIY Flat Fee.com
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  /62

  $399,900 Pending

  • 3 Beds
  • 3 Baths
  • 2,475 Sq Ft

  601 Gilbert Ct, Winchester, KY 40391

  Welcome to 601 Gilbert Court in Winchester, KY. Tucked away in a quiet cul de sac in a desirable neighborhood, this spacious 3 bedroom, 3 full bathroom home offers room to spread out with a large open concept living room and kitchen that is perfect for gathering, entertaining, or simply enjoying everyday life. The oversized living space flows effortlessly into the kitchen and dining area,

  Brooke Otis Mullins RO&CO Real Estate

  601 Gilbert Ct, Winchester, KY 40391
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  /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 $337,463

  Last Listing Agent Melissa Brown Keller Williams Legacy Group

  366 Hanover Dr, Winchester, KY 40391
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  /26

  Est $250,442 Not Listed For Sale

  20 Jackson St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,650 Sq Ft
  • Built 1940

  20 Jackson St, Winchester, KY 40391

  Last Sold Summary

  • 4% Above List Price
  • $146/SF
  • 10 Days On Market

  Last Sold Price $240,900

  Last Listing Agent Jonathan Wood HomeLand Real Estate Inc - Mt Sterling
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  /5

  $29,000

  • Land
  • 0.46 Acre
  • $63,043 per Acre

  102 Augusta Dr, Winchester, KY 40391

  This is a beautiful area to build your dream home. Backs up to a golf course for a magnificent view. Just minutes from Fort Boonesborough National Park.

  Dale Hatton Dream Maker Realty, LLC

  102 Augusta Dr, Winchester, KY 40391
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  /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 $144,535

  Last Listing Agent Darrell Lewis DIYFlatFee.Com

  17 Waveland Ave, Winchester, KY 40391
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  /25

  Est $209,510 Not Listed For Sale

  21 Vine St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,080 Sq Ft
  • Built 1960

  21 Vine St, Winchester, KY 40391

  Last Sold Summary

  • 2% Above List Price
  • $190/SF
  • 0 Days On Market

  Last Sold Price $204,900

  Last Listing Agent Kymberly McCreary EXP Realty, LLC
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  /2

  $110,000

  • Land
  • 0.32 Acre
  • $343,750 per Acre

  135 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

  135 Jacob Ct, Winchester, KY 40391
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  /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 $218,554

  Last Listing Agent Elizabeth Hodge Lifstyl Real Estate

  213 Blair Ave, Winchester, KY 40391
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  /39

  Est $260,173 Not Listed For Sale

  217 E Washington St, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,183 Sq Ft
  • Built 1940

  217 E Washington St, Winchester, KY 40391

  Last Sold Summary

  • 11% Above List Price
  • $108/SF
  • 21 Days On Market

  Last Sold Price $235,000

  Last Listing Agent Joshua Lynch The Brokerage
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  /62

  $259,500

  • 3 Beds
  • 2 Baths
  • 1,247 Sq Ft

  3614 Stamper Dr, Winchester, KY 40391

  Fully renovated to perfection, this exceptional home showcases high-end upgrades throughout. Enjoy newly installed windows, doors, and sleek flooring, all complemented by modern appliances and updated cabinetry. A brand-new deck creates the perfect spot for outdoor relaxation, while the freshly built storage building out back adds extra convenience. The attached garage offers attic access with

  Darrell Tackett Dream Maker Realty, LLC

  3614 Stamper Dr, Winchester, KY 40391
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  /2

  $110,000 Sold May 13, 2025

  140 Duclair Dr, Winchester, KY 40391

  • Land
  • 0.42 Acre
  • $261,905 per Acre

  Last Sold Summary

  • 900 Days On Market

  Last Listing Agent John Wilson Bluegrass Properties Group

  140 Duclair Dr, Winchester, KY 40391
• 

  

  /29

  Est $232,841 Not Listed For Sale

  167 E Washington St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,763 Sq Ft
  • Built 1940

  167 E Washington St, Winchester, KY 40391

  Last Sold Summary

  • 8% Above List Price
  • $122/SF
  • 5 Days On Market

  Last Sold Price $215,000

  Last Listing Agent Kymberly McCreary EXP Realty, LLC
• 

  /2

  $110,000

  • Land
  • 0.32 Acre
  • $343,750 per Acre

  115 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

  115 Jacob Ct, Winchester, KY 40391
• 

  

  /44

  $515,000 Sold May 19, 2025

  31 Bonnie Brook Ln, Winchester, KY 40391

  • 5 Beds
  • 3.5 Baths
  • 4,091 Sq Ft
  • Built 1958

  Last Sold Summary

  • 10% Below List Price
  • $126/SF
  • 294 Days On Market

  Current Estimated Value $545,180

  Last Listing Agent Kelly Nisbet Coldwell Banker McMahan

  31 Bonnie Brook Ln, Winchester, KY 40391
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  /27

  Est $157,422 Not Listed For Sale

  47 Buckner St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,632 Sq Ft
  • Built 1930

  47 Buckner St, Winchester, KY 40391

  Last Sold Summary

  • 57% Above List Price
  • $61/SF
  • 17 Days On Market

  Last Sold Price $100,000

  Last Listing Agent Keith Wilson Coldwell Banker McMahan
• 

  

  /4

  $635,000 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,537 Sq Ft

  422 Alexis Way, Winchester, KY 40391

  Introducing the Denver, a gorgeous all-brick ranch home offering 4 bedrooms and 2.5 baths, designed for both luxury and practicality. With its stunning curb appeal, front porch, and beam accents, this home makes a lasting first impression. Inside, the split-bedroom layout offers privacy and space for everyone, with a large primary suite featuring a walk-in closet, soaking tub, separate shower,

  Shane Underwood Keller Williams Commonwealth

  422 Alexis Way, Winchester, KY 40391
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  /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
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  /26

  Est $186,730 Not Listed For Sale

  150 W Broadway St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,696 Sq Ft
  • Built 1940

  150 W Broadway St, Winchester, KY 40391

  Last Sold Summary

  • 29% Above List Price
  • $85/SF
  • 39 Days On Market

  Last Sold Price $145,000

  Last Listing Agent Michelle Blackburn RE/MAX
• 

  

  /27

  $160,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,088 Sq Ft

  233 E Washington St, Winchester, KY 40391

  Welcome to 233 E. Washington Street, a charming ranch-style home offering comfort, space, and convenience in the heart of Winchester. The Roof, Windows and HVAC are updated. This 2-bedroom, 1-bath residence features an open-concept layout designed for easy living and everyday functionality. LVP flooring runs throughout the home, providing a clean, modern look that's both durable and low

  Lukas Owens The Brokerage

  233 E Washington St, 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 $464,023

  Last Listing Agent O Eve Stern Threshold Real Estate Services

  497 Goose Creek Rd, Winchester, KY 40391
• 

  

  /11

  Est $128,967 Not Listed For Sale

  30 Madison Ave, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft
  • Built 1996

  30 Madison Ave, Winchester, KY 40391

  Last Sold Summary

  • 17% Above List Price
  • $143/SF
  • 18 Days On Market

  Last Sold Price $110,000

  Last Listing Agent Michelle Newman Team Pannell Real Estate
• 

  /2

  $110,000

  • Land
  • 0.5 Acre
  • $220,000 per Acre

  260 Duclair Dr, 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

  260 Duclair 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 $298,976

  Last Listing Agent Alyssa M Boley Coldwell Banker McMahan

  220 Mcdowell Dr, Winchester, KY 40391
• 

  

  /25

  Est $167,935 Not Listed For Sale

  15 Madison Ave, Winchester, KY 40391

  • 2 Beds
  • 1.5 Baths
  • 960 Sq Ft
  • Built 1996

  15 Madison Ave, Winchester, KY 40391

  Last Sold Summary

  • 13% Above List Price
  • $155/SF
  • 1 Day On Market

  Last Sold Price $149,000

  Last Listing Agent Tyanne Whitworth RE/MAX
• 

  

  /12

  $296,000

  • 5 Beds
  • 2 Baths
  • 2,214 Sq Ft

  55 Hillcrest Dr, Winchester, KY 40391

  All-brick ranch with a full walk-out basement! This charming home offers excellent potential for the right buyer. The main level features three bedrooms, a full bath, a comfortable living room, and an eat-in kitchen. The walk-out basement expands the living space with two additional bedrooms, full bath, family room with a kitchenette area, utility room, and ample storage with built-in shelving.

  Nina Vanetten RE/MAX Elite Lexington

  55 Hillcrest Dr, Winchester, KY 40391
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  /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 $255,668

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate

  752 Wayland Dr, Winchester, KY 40391

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