Homes in ZIP Code 40391

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  /103

  $2,650,000

  • 6 Beds
  • 5.5 Baths
  • 7,274 Sq Ft

  5045 Van Meter Rd, Winchester, KY 40391

  Welcome to a truly exceptional 10-acre estate, where luxury and nature converge. This custom-built, three-story home, completed in 2006 , offers 7274 sq ft of meticulously designed living space. With 6 bedrooms and 5.5 bathrooms, there's ample room for family and guests. The impressive 2432 sq ft, temperature-controlled 5-car garage provides extensive space for vehicles and hobbies. Beyond the

  The Prather Team - Michael Prather Keller Williams Bluegrass Realty

  5045 Van Meter Rd, Winchester, KY 40391
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  /48

  $222,500 Sold Jul 28, 2025

  217 Locust Grove Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,055 Sq Ft
  • Built 1955

  Last Sold Summary

  • 1% Above List Price
  • $108/SF
  • 2 Days On Market

  Current Estimated Value $228,093

  Last Listing Agent Robin Murray The Agency

  217 Locust Grove Rd, Winchester, KY 40391
• 

  

  

  /17

  Est $245,869 Not Listed For Sale

  206 Buffalo Trace, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 1,737 Sq Ft
  • Built 1998

  206 Buffalo Trace, Winchester, KY 40391

  Last Sold Summary

  • 3% Above List Price
  • $138/SF
  • 30 Days On Market

  • Last Sold Price $239,000
  • Dec 16, 2024

  Last Listing Agent Kymberly McCreary EXP Realty, LLC
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  /30

  $209,000

  • 4 Beds
  • 2 Baths
  • 2,683 Sq Ft

  217 S Highland St, Winchester, KY 40391

  This Spacious investment property is ready for its new owner. The home features fresh updates throughout, large living spaces and endless possibilities. Schedule your showing while you can!

  Michael Hilario The Agency

  217 S Highland St, Winchester, KY 40391
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  /34

  $342,000 Sold Sep 16, 2025

  3560 Wades Mill Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,305 Sq Ft
  • Built 1950

  Last Sold Summary

  • 10% Below List Price
  • $262/SF
  • 37 Days On Market

  Current Estimated Value $342,626

  Last Listing Agent Sarah MacHarg Kentucky Land and Home

  3560 Wades Mill Rd, Winchester, KY 40391
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  /32

  Est $211,526 Not Listed For Sale

  303 Geronimo Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,088 Sq Ft
  • Built 1998

  303 Geronimo Ct, Winchester, KY 40391

  Last Sold Summary

  • 7% Above List Price
  • $182/SF
  • 6 Days On Market

  • Last Sold Price $198,000
  • Dec 11, 2024

  Last Listing Agent Marie Waddell-Pearson RE/MAX
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  /2

  $10,000 Pending

  • Land
  • 2,613 Sq Ft
  • $166,667 per Acre

  75 4th St, Winchester, KY 40391

  Explore the opportunity to build your next home or investment property on this 0.06-acre residential lot located at 75 4th Street. Nestled in an established neighborhood, this lot offers convenient access to local amenities, schools, and nearby roadways. With public utilities available in the area, it's a great option for new construction or future development. Whether you're a builder, investor,

  Bob Sophiea eXp Realty, LLC

  75 4th St, Winchester, KY 40391
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  /5

  $41,500 Sold Sep 15, 2025

  434 Fairholme Way, Winchester, KY 40391

  • Land
  • 15,681 Sq Ft
  • $115,278 per Acre

  Last Sold Summary

  • 8% Below List Price
  • 6 Days On Market

  Current Estimated Value $52,175

  Last Listing Agent Justin Lee JL Realty Group, LLC

  434 Fairholme Way, Winchester, KY 40391
• 

  

  /19

  Est $192,858 Not Listed For Sale

  125 Buffalo Trace, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 932 Sq Ft
  • Built 1997

  125 Buffalo Trace, Winchester, KY 40391

  Last Sold Summary

  • 16% Above List Price
  • $178/SF
  • 43 Days On Market

  • Last Sold Price $166,000
  • Jan 24, 2025

  Last Listing Agent Elizabeth Herrington Bluegrass Sotheby's International Realty
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  /2

  $110,000

  • Land
  • 20,473 Sq Ft
  • $234,043 per Acre

  139 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

  139 Jacob Ct, Winchester, KY 40391
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  /48

  $330,000 Sold May 23, 2025

  113 Holiday Rd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,090 Sq Ft
  • Built 1970

  Last Sold Summary

  • 3% Below List Price
  • $158/SF
  • 35 Days On Market

  Current Estimated Value $317,465

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  113 Holiday Rd, Winchester, KY 40391
• 

  

  /22

  Est $184,624 Not Listed For Sale

  113 Buffalo Trace, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 960 Sq Ft
  • Built 1998

  113 Buffalo Trace, Winchester, KY 40391

  Last Sold Summary

  • 9% Above List Price
  • $177/SF
  • 2 Days On Market

  • Last Sold Price $170,000
  • Mar 28, 2024

  Last Listing Agent Elizabeth Herrington Bluegrass Sotheby's International Realty
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  /32

  $249,900

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

  528 Estes Dr, Winchester, KY 40391

  Don't miss out on seeing this 3/2 brick ranch home in a convenient location to shopping, dining, parks, pool and more. Large open family room and kitchen with bamboo flooring. The kitchen has a large granite counter top island with newer stainless appliances and a gas range. This home is complete with an Aurora above ground pool for all the summer fun. The seller has already planted garden

  Josh Wood Freedom Realty & Property Management

  528 Estes Dr, Winchester, KY 40391
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  /58

  $830,000 Sold Feb 27, 2026

  2395 Becknerville Rd, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 3,234 Sq Ft
  • Built 2012

  Last Sold Summary

  • 2% Below List Price
  • $257/SF
  • 8 Days On Market

  Current Estimated Value $834,586

  Last Listing Agent Crystal Towe The Real Estate Group

  2395 Becknerville Rd, Winchester, KY 40391
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  /47

  Est $597,827 Not Listed For Sale

  1305 Irvine Rd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 3,020 Sq Ft
  • Built 1918

  1305 Irvine Rd, Winchester, KY 40391

  Last Sold Summary

  • 10% Above List Price
  • $179/SF
  • 406 Days On Market

  • Last Sold Price $542,000
  • Aug 03, 2023

  Last Listing Agent Bonnie Mays United Real Estate Bluegrass
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  /33

  $219,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,340 Sq Ft

  21 Kentucky St, Winchester, KY 40391

  Updated, move-in ready, and right in the heart of Winchester. This is the kind of home that checks boxes and feels good the second you walk in. Start your mornings or wind down in the evenings on the inviting covered front porch—it's the kind of space that makes you want to slow down for a minute. Inside, everything has been updated so you can skip the projects and just enjoy your home from day

  Jenny Mateyoke Keller Williams Legacy Group

  21 Kentucky St, Winchester, KY 40391
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  /33

  $364,900 Sold Feb 06, 2026

  446 Tremont Ln, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,811 Sq Ft
  • Built 2005

  Last Sold Summary

  • 1% Below List Price
  • $130/SF
  • 15 Days On Market

  Current Estimated Value $365,014

  Last Listing Agent Dylan Langdon The Agency

  446 Tremont Ln, Winchester, KY 40391
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  /99

  Est $261,843 Not Listed For Sale

  514 E Broadway St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,394 Sq Ft
  • Built 1960

  514 E Broadway St, Winchester, KY 40391

  Last Sold Summary

  • 9% Above List Price
  • $172/SF
  • 1 Day On Market

  • Last Sold Price $239,900
  • Oct 02, 2023

  Last Listing Agent Josh Wood Freedom Realty & Property Management
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  /2

  $882,000

  • Land
  • 3.93 Acres
  • $224,427 per Acre

  Lot 1 - 7 Plantations Dr, Winchester, KY 40391

  NOW SELLING PHASE ONE: 7 of the 12 Buildable Lots (minimum lot is 9600+ sqft) of PHASE ONE of Deerlawn's Development located at 2395 Paris Rd (Parent Listing). Earmarked as Winchester, Ky's most anticipated residential development consisting of an ambitious 274+-acre expansion formerly known as the well-established Royal Oaks/Plantation neighborhoods, Phase One has 12 lots ready for you to build

  Melia Hord Keller Williams Legacy Group

  Lot 1 - 7 Plantations Dr, Winchester, KY 40391
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  /38

  $173,000 Sold Sep 22, 2025

  44 5th St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,270 Sq Ft
  • Built 1952

  Last Sold Summary

  • 2% Above List Price
  • $136/SF
  • 2 Days On Market

  Current Estimated Value $173,736

  Last Listing Agent Tirza Cooper The Howard Realty Co

  44 5th St, Winchester, KY 40391
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  /30

  Est $196,919 Not Listed For Sale

  1 Apache Trail, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,584 Sq Ft
  • Built 1969

  1 Apache Trail, Winchester, KY 40391

  Last Sold Summary

  • 27% Above List Price
  • $98/SF
  • 10 Days On Market

  • Last Sold Price $155,000
  • Jan 18, 2024

  Last Listing Agent Peter doCouto Plum Tree Realty
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  /2

  $150,000

  • Land
  • 2.11 Acres
  • $71,090 per Acre

  125 Knox 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

  125 Knox Ct, Winchester, KY 40391
• 

  

  /18

  $200,000 Sold Jan 14, 2026

  245 Ecton Rd, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,074 Sq Ft
  • Built 1940

  Last Sold Summary

  • 9% Below List Price
  • $186/SF
  • 2 Days On Market

  Current Estimated Value $198,756

  Last Listing Agent Anthony Gigilo ListWithFreedom.com

  245 Ecton Rd, Winchester, KY 40391
• 

  

  /27

  Est $215,422 Not Listed For Sale

  7 Pocahontas Trail, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,550 Sq Ft
  • Built 1969

  7 Pocahontas Trail, Winchester, KY 40391

  Last Sold Summary

  • 13% Above List Price
  • $123/SF
  • 7 Days On Market

  • Last Sold Price $190,000
  • Apr 18, 2025

  Last Listing Agent Mila Ensor Ensor Real Estate, LLC
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  /14

  $300,000

  • Land
  • 15.27 Acres
  • $19,652 per Acre

  4025 Jackson Ferry Rd, Winchester, KY 40391

  Opportunities like this are incredibly rare—15.266 combined acres backing to the Kentucky River, offering the ultimate private retreat. Located at the end of a scenic drive, these two tracts are being offered together, creating an expansive recreational property with unmatched access to the water. Ideal for camping, family getaways, or creating a multi-use outdoor haven, this land provides

  Christa Joynt Keller Williams Commonwealth

  4025 Jackson Ferry Rd, Winchester, KY 40391
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  /52

  $500,000 Sold Aug 25, 2025

  1778 Elkin Rd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,020 Sq Ft
  • Built 2015

  Last Sold Summary

  • 7% Below List Price
  • $248/SF
  • 103 Days On Market

  Last Listing Agent Vicki VanWinkle ERA Select Real Estate

  1778 Elkin Rd, Winchester, KY 40391
• 

  

  /57

  Est $192,292 Not Listed For Sale

  17 Hiawatha Trail, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,000 Sq Ft
  • Built 1968

  17 Hiawatha Trail, Winchester, KY 40391

  Last Sold Summary

  • 13% Above List Price
  • $170/SF
  • 32 Days On Market

  • Last Sold Price $170,000
  • Dec 30, 2024

  Last Listing Agent Josh Wood Freedom Realty & Property Management
• 

  

  /57

  $275,000

  • 3 Beds
  • 2 Baths
  • 1,779 Sq Ft

  720 Terry Dr, Winchester, KY 40391

  Welcome home to this beautifully refreshed 3-bedroom, 2-bath property located in the heart of Winchester, KY, just minutes from the Winchester Bypass for quick and easy commuting. Priced at $275,000, this home offers exceptional value in a highly walkable and convenient neighborhood. Step inside to find a freshly painted interior that feels bright, clean, and move-in ready. The thoughtful layout

  Christa Joynt Keller Williams Commonwealth

  720 Terry Dr, Winchester, KY 40391
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  /28

  $203,900 Sold Dec 10, 2025

  25 Hiawatha Trail, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 925 Sq Ft
  • Built 1968

  Last Sold Summary

  • 3% Below List Price
  • $220/SF
  • 35 Days On Market

  Current Estimated Value $199,235

  Last Listing Agent Sarah Hess Keller Williams Commonwealth

  25 Hiawatha Trail, Winchester, KY 40391
• 

  

  /15

  Est $193,947 Not Listed For Sale

  13 Hiawatha Trail, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,006 Sq Ft
  • Built 1968

  13 Hiawatha Trail, Winchester, KY 40391

  Last Sold Summary

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

  • Last Sold Price $185,000
  • Aug 25, 2023

  Last Listing Agent Patrick Arvin Keller Williams Commonwealth
• 

  

  /26

  $269,000 Pending

  • 4 Beds
  • 2 Baths
  • 2,295 Sq Ft

  86 Bon-Haven Ave, Winchester, KY 40391

  Welcome to this spacious 4-bedroom, 2 bath home offering plenty of room to grow and make your own. With generous living areas and a functional layout, this property is perfect for those seeking space, comfort and opportunity. The home features a 2-car attached garage along with an additional 676 SF detached 2-car garage, providing ample room for vehicles, storage or a workshop. Outside you will

  Tracey Goebel Tom Goebel & Company

  86 Bon-Haven Ave, Winchester, KY 40391
• 

  

  /80

  $524,000 Sold Dec 16, 2025

  160 Agawam Rd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 4,933 Sq Ft
  • Built 1978

  Last Sold Summary

  • 9% Below List Price
  • $106/SF
  • 51 Days On Market

  Current Estimated Value $522,998

  Last Listing Agent Megan McCoy Keller Williams Legacy Group

  160 Agawam Rd, Winchester, KY 40391
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  /29

  Est $240,045 Not Listed For Sale

  46 Hiawatha Trail, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Built 1970

  46 Hiawatha Trail, Winchester, KY 40391

  Last Sold Summary

  • 10% Above List Price
  • $145/SF
  • 2 Days On Market

  • Last Sold Price $218,000
  • Aug 18, 2023

  Last Listing Agent Christina Baker United Real Estate Louisville
• 

  

  /17

  $124,500

  • 2 Beds
  • 1 Bath
  • 876 Sq Ft

  122 Calloway St, Winchester, KY 40391

  Investment Opportunity or Perfect Starter Home This charming 2-bedroom, 1-bath property is full of potential! With a strong rental history and an excellent lease track record, it's ideal for investors or first-time buyers. The home requires only light maintenance, and the seller is even willing to fund minor repairs. Don't miss your chance to own a property with great value and endless

  Darrell Tackett Dream Maker Realty, LLC

  122 Calloway St, Winchester, KY 40391
• 

  

  /3

  $220,000 Sold Jul 30, 2025

  412 Paisley Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,300 Sq Ft
  • Built 2005

  Last Sold Summary

  • 4% Below List Price
  • $169/SF
  • 38 Days On Market

  Current Estimated Value $223,400

  Last Listing Agent John Wilson Bluegrass Properties Group

  412 Paisley Ct, Winchester, KY 40391
• 

  

  /24

  Est $258,126 Not Listed For Sale

  108 Dixon Way, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,377 Sq Ft
  • Built 2006

  108 Dixon Way, Winchester, KY 40391

  Last Sold Summary

  • $187/SF
  • 124 Days On Market

  • Last Sold Price $257,500
  • Aug 29, 2024

  Last Listing Agent Angie Conley Dixon Dixon Properties
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  /75

  $600,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 3,391 Sq Ft

  905 Pretty Run Rd, Winchester, KY 40391

  Welcome to this elevated farmhouse classic-refined yet unpretentious, elegant yet entirely inviting. The kind of home that feels just as suited for quiet family life as it does for hosting gatherings that spill effortlessly from indoors to out with the wrap around porch, deck, outdoor kitchen & grill, POOL and hot tub spa, firepit & so much more...Welcome to 905 Pretty Run Road! Greeted by a

  Niki Wiley Bluegrass Sotheby's International Realty

  905 Pretty Run Rd, Winchester, KY 40391
• 

  

  /41

  $300,300 Sold Nov 07, 2025

  37 Lynnway Dr, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 3,220 Sq Ft
  • Built 1976

  Last Sold Summary

  • $93/SF
  • 58 Days On Market

  Current Estimated Value $322,188

  Last Listing Agent Donna Thwaites Thwaites Realtors LLC

  37 Lynnway Dr, Winchester, KY 40391
• 

  

  /19

  Est $215,962 Not Listed For Sale

  170 Center Dr, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,517 Sq Ft
  • Built 1961

  170 Center Dr, Winchester, KY 40391

  Last Sold Summary

  • 49% Above List Price
  • $96/SF
  • 52 Days On Market

  • Last Sold Price $145,000
  • Jan 04, 2024

  Last Listing Agent Larry Moore CENTURY 21 Simpson & Associates
• 

  

  /25

  $295,000 Pending

  • Land
  • 10 Acres
  • $29,500 per Acre

  398 Pine Ridge Rd, Winchester, KY 40391

  **** CONTRACT ACCEPTED WITH 48 KICK OUT***Discover the charm of country living at 398 Pine Ridge Rd in Winchester, KY. This inviting 2-bedroom, 1-bath home sits on 10 picturesque acres, offering the perfect retreat for those who love peace, privacy, and the beauty of the Kentucky countryside. Step inside to a warm and cozy interior with a simple, functional layout that feels like home the moment

  Amie Hieneman ERA Select Real Estate

  398 Pine Ridge Rd, Winchester, KY 40391

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