Homes in ZIP Code 40391

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  /35

  $248,000 Sold May 22, 2025

  206 Moss Cir, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,773 Sq Ft
  • Built 1997

  Last Sold Summary

  • 6% Below List Price
  • $140/SF
  • 20 Days On Market

  Current Estimated Value $259,201

  Last Listing Agent David Baesler Kentucky Dreams Realty

  206 Moss Cir, Winchester, KY 40391
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  /31

  Est $217,968 Not Listed For Sale

  208 Locust Grove Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,494 Sq Ft
  • Built 1950

  208 Locust Grove Rd, Winchester, KY 40391

  Last Sold Summary

  • 6% Above List Price
  • $137/SF
  • 9 Days On Market

  Last Sold Price $205,000

  Last Listing Agent Shane Underwood Keller Williams Commonwealth
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  /2

  $195,000

  6699 Boonesboro Rd, Winchester, KY 40391

  READY TO BUILD OR HUNT? We have the perfect spot for you! Mostly wooded 8.35 acres, tract 2B, of green, treed, Bluegrass Heaven. Close proximity to I 75 and I 64 as well as Lexington, Richmond, and Winchester. Bring your own builder or we can help you find one!

  Jennifer Ray RE/MAX Elite Lexington

  6699 Boonesboro Rd, Winchester, KY 40391
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  /3

  $554,651 Sold Jul 10, 2025

  426 Alexis Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,400 Sq Ft
  • Built 2024

  Last Sold Summary

  • 4% Above List Price
  • $231/SF
  • 21 Days On Market

  Current Estimated Value $548,631

  Last Listing Agent Shane Underwood Keller Williams Commonwealth

  426 Alexis Way, Winchester, KY 40391
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  /18

  Est $160,331 Not Listed For Sale

  108 Crawford Ave, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Built 1955

  108 Crawford Ave, Winchester, KY 40391

  Last Sold Summary

  • 23% Above List Price
  • $144/SF
  • 0 Days On Market

  Last Sold Price $130,000

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC
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  /3

  $670,000 New Construction

  • 3 Beds
  • 2 Baths
  • 2,261 Sq Ft

  113 Bella Shae Way, Winchester, KY 40391

  Introducing the Hampton, a beautiful all-brick ranch home. This 3-bedroom, 2-bath split-bedroom design offers both privacy and comfort. The spacious primary suite is a true retreat, featuring a luxurious ensuite with double vanities, a walk-in shower, and dual walk-in closets. The open-concept kitchen and great room are perfect for entertaining, highlighted by a gas log fireplace, a large kitchen

  Shane Underwood Keller Williams Commonwealth

  113 Bella Shae Way, Winchester, KY 40391
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  /48

  $341,500 Sold Jun 27, 2025

  401 Cedar Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,834 Sq Ft
  • Built 1996

  Last Sold Summary

  • 1% Above List Price
  • $186/SF
  • 2 Days On Market

  Current Estimated Value $348,268

  Last Listing Agent Geneva Wilder Stewart & Co Realty LLC

  401 Cedar Ct, Winchester, KY 40391
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  /10

  Est $196,134 Not Listed For Sale

  24 Fairview Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,265 Sq Ft
  • Built 1940

  24 Fairview Ave, Winchester, KY 40391

  Last Sold Summary

  • 23% Above List Price
  • $126/SF
  • 1 Day On Market

  Last Sold Price $159,900

  Last Listing Agent Sondra Clark Taylor Real Estate, LLC
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  /100

  $429,900

  • 4 Beds
  • 2.5 Baths
  • 1,500 Sq Ft

  240 Athens Boonesboro Rd, Winchester, KY 40391

  Rare Investment Opportunity on the Kentucky River! Two incredible homes on 3 beautiful acres — endless potential awaits. Live in the charming log cabin and let the second home pay the mortgage with its long term, reliable tenant already in place. This property offers room to dream: -Build a future campground -Create a private riverside retreat -Expand for additional rentals -Or simply enjoy your

  Darrell Tackett Dream Maker Realty, LLC

  240 Athens Boonesboro Rd, Winchester, KY 40391
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  /2

  $610,000 Sold Aug 29, 2025

  4560 Pine Ridge Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,848 Sq Ft
  • Built 1905

  Last Sold Summary

  • $330/SF
  • 1 Day On Market

  Current Estimated Value $618,608

  Last Listing Agent Natalie Avant Berkshire Hathaway HomeServices Foster Realtors

  4560 Pine Ridge Rd, Winchester, KY 40391
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  /55

  Est $182,253 Not Listed For Sale

  30 Ashland Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,416 Sq Ft
  • Built 1983

  30 Ashland Ave, Winchester, KY 40391

  Last Sold Summary

  • 9% Above List Price
  • $118/SF
  • 8 Days On Market

  Last Sold Price $166,500

  Last Listing Agent Christa Joynt Keller Williams Commonwealth
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  /84

  $799,900

  • 4 Beds
  • 3.5 Baths
  • 4,922 Sq Ft

  2509 Mount Sterling Rd, Winchester, KY 40391

  Embrace Bluegrass living with this beautiful fieldstone ranch on 10+ acres in the heart of horse country. Just minutes from interstate access, yet surrounded by rolling hills and scenic views, this mini farm offers a larger barn with 6 stalls, including water and electric connection, 90 foot roof hangover on the barn, 5 paddocks, each with their own gate and water ran along each paddock. The home

  Josh Wood Freedom Realty & Property Management

  2509 Mount Sterling Rd, Winchester, KY 40391
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  /32

  $263,000 Sold Sep 05, 2025

  2 Chickadee Ln, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,397 Sq Ft
  • Built 1960

  Last Sold Summary

  • 1% Above List Price
  • $188/SF
  • 2 Days On Market

  Current Estimated Value $256,602

  Last Listing Agent Ashley Spencer Keller Williams Commonwealth

  2 Chickadee Ln, Winchester, KY 40391
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  /30

  Est $176,013 Not Listed For Sale

  370 E Washington St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,126 Sq Ft
  • Built 1930

  370 E Washington St, Winchester, KY 40391

  Last Sold Summary

  • 17% Above List Price
  • $133/SF
  • 3 Days On Market

  Last Sold Price $150,000

  Last Listing Agent Meredith Story Story Realty
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  /2

  $100,000

  • Land
  • 1.1 Acres
  • $90,909 per Acre

  270 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

  270 Duclair Dr, Winchester, KY 40391
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  /35

  $325,000 Sold Nov 21, 2025

  130 Hibiscus Ln, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 1,900 Sq Ft
  • Built 2000

  Last Sold Summary

  • 7% Below List Price
  • $171/SF
  • 19 Days On Market

  Current Estimated Value $334,469

  Last Listing Agent Ashley Barreto Indigo & Co

  130 Hibiscus Ln, Winchester, KY 40391
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  /32

  Est $193,923 Not Listed For Sale

  203 Crawford Ct, Winchester, KY 40391

  • 2 Beds
  • 2 Baths
  • 1,900 Sq Ft
  • Built 1960

  203 Crawford Ct, Winchester, KY 40391

  Last Sold Summary

  • 12% Above List Price
  • $91/SF
  • 17 Days On Market

  Last Sold Price $173,000

  Last Listing Agent Andrew Fugitt Coldwell Banker McMahan
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  /31

  $379,717 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,636 Sq Ft

  300 Calmes Blvd, Winchester, KY 40391

  Gorgeous & Spacious 3BR/2.5BA Home in Calmes Estates . Welcome to your dream home in the highly sought-after Calmes Estates neighborhood! This beautifully maintained 3-bedroom, 2.5-bath residence offers generous living space and a layout perfect for families or entertaining guests. Highlights: *Expansive open-concept living areas *three spacious bedrooms with ample closet space *Two and a half

  Darrell Tackett Dream Maker Realty, LLC

  300 Calmes Blvd, Winchester, KY 40391
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  /51

  $303,000 Sold Jan 16, 2026

  22 N Bloomfield Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,913 Sq Ft
  • Built 1919

  Last Sold Summary

  • 5% Below List Price
  • $158/SF
  • 16 Days On Market

  Current Estimated Value $302,839

  Last Listing Agent Libby VanMeter Marshall Lane Real Estate - Lexington

  22 N Bloomfield Rd, Winchester, KY 40391
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  /53

  Est $208,774 Not Listed For Sale

  29 Fairview Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,631 Sq Ft
  • Built 1960

  29 Fairview Ave, Winchester, KY 40391

  Last Sold Summary

  • 111% Above List Price
  • $61/SF
  • 140 Days On Market

  Last Sold Price $99,000

  Last Listing Agent Bob Sophiea eXp Realty, LLC
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  /9

  $500,000

  • Land
  • 1.52 Acres
  • $328,947 per Acre

  1005 Early Dr, Winchester, KY 40391

  Visibility, Access, Utilities on site per seller/per plat-buyer to verify, zoned B-3. 1.52 acres located at I-64 exit 96, Right in front of the Hampton Inn, buyer to verify and satisfy themselves to all aspects and information on property. and inspections sold as is. Buyer to Check with all utilities companies to very water electric and gas availability and locations on all utilities.

  Whitney Ensor Ensor Real Estate, LLC

  1005 Early Dr, Winchester, KY 40391
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  /23

  $244,895 Sold Jun 10, 2025

  244 Bay Hill Ct, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 2,536 Sq Ft
  • Built 2006

  Last Sold Summary

  • 2% Below List Price
  • $97/SF
  • 10 Days On Market

  Current Estimated Value $267,697

  Last Listing Agent Destiny Darby Keller Williams Commonwealth

  244 Bay Hill Ct, Winchester, KY 40391
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  /29

  Est $164,276 Not Listed For Sale

  4 Sylvania Ave, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 832 Sq Ft
  • Built 1960

  4 Sylvania Ave, Winchester, KY 40391

  Last Sold Summary

  • 17% Above List Price
  • $168/SF
  • 4 Days On Market

  Last Sold Price $140,000

  Last Listing Agent Christal Browning Four Seasons Realty
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  /14

  $650,000

  • Land
  • 3 Acres
  • $216,667 per Acre

  205 Codella Dr, Winchester, KY 40391

  Great opportunity to buy and build just off the Winchester Bypass. This property is nicely located in the midst of a great deal of new development including a brand new, state-of-the-art CHI Saint Joseph Health Center. Other new development in the immediate area includes Zips Car Wash and Domino's Pizza. Additionally, Walmart and Kroger are located directly across the Bypass from this site. See

  Greg Leveridge Block + Lot Real Estate

  205 Codella Dr, Winchester, KY 40391
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  /2

  $89,000 Sold Dec 18, 2025

  13067 Irvine Rd, Winchester, KY 40391

  • Land
  • 7.86 Acres
  • $11,323 per Acre

  Last Sold Summary

  • 78 Days On Market

  Last Listing Agent Mendel Tipton Natural Bridge Realty

  13067 Irvine Rd, Winchester, KY 40391
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  /22

  Est $182,326 Not Listed For Sale

  21 Sylvania Ave, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,016 Sq Ft
  • Built 1970

  21 Sylvania Ave, Winchester, KY 40391

  Last Sold Summary

  • 17% Above List Price
  • $154/SF
  • 1 Day On Market

  Last Sold Price $156,000

  Last Listing Agent Ciara Isaacs Hagedorn RE/MAX
• 

  

  /3

  $430,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,855 Sq Ft

  250 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, unfinished walkout basement and thoughtful living spaces throughout. The spacious primary suite features a large walk-in closet and a private ensuite

  Rex Hall United Real Estate Bluegrass

  250 Evergreen Dr, Winchester, KY 40391
• 

  /2

  $4,900,000 Sold Dec 23, 2025

  175 Chatham Place, Winchester, KY 40391

  • 2 Beds
  • 3 Baths
  • 37,192 Sq Ft
  • Built 2007

  Last Sold Summary

  • 13% Below List Price
  • $132/SF
  • 111 Days On Market

  Current Estimated Value $4,910,294

  Last Listing Agent Garry Milton Milton and Associates Real Estate

  175 Chatham Place, Winchester, KY 40391
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  /30

  Est $198,797 Not Listed For Sale

  280 Winn Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,432 Sq Ft
  • Built 1960

  280 Winn Ave, Winchester, KY 40391

  Last Sold Summary

  • 28% Above List Price
  • $108/SF
  • 3 Days On Market

  Last Sold Price $155,000

  Last Listing Agent Whitney Ensor Ensor Real Estate, LLC
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  /6

  $110,000

  • Land
  • 2.06 Acres
  • $53,398 per Acre

  1185 Craig Crossing Rd, Winchester, KY 40391

  Lot # 30 contains 2.058 acres of gently rolling land perfect for your new home. This is a rare opportunity to own a piece of western Clark County real estate in the sought-after McClure Road area. Thoroughbred Estates is Winchester's newest upscale development containing 33 lots from 2 acres to nearly 7 acres. Lots are located just minutes from Winchester and Lexington.

  Keith Wilson Coldwell Banker McMahan

  1185 Craig Crossing Rd, Winchester, KY 40391
• 

  

  /51

  $340,000 Sold Oct 30, 2025

  356 Boone Ave, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 3,200 Sq Ft
  • Built 1940

  Last Sold Summary

  • 5% Below List Price
  • $106/SF
  • 30 Days On Market

  Current Estimated Value $344,847

  Last Listing Agent Elizabeth Hodge Lifstyl Real Estate

  356 Boone Ave, Winchester, KY 40391
• 

  

  /25

  Est $110,880 Not Listed For Sale

  248 Cook Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,465 Sq Ft
  • Built 1940

  248 Cook Ave, Winchester, KY 40391

  Last Sold Summary

  • 122% Above List Price
  • $34/SF
  • 27 Days On Market

  Last Sold Price $50,000

  Last Listing Agent Chris Johnson Plum Tree Realty
• 

  

  /26

  $175,000 Pending

  • 2 Beds
  • 1.5 Baths
  • 924 Sq Ft

  10 Pocahontas Trail, Winchester, KY 40391

  This inviting 2 bedroom, 1 and a half bath home blends comfort with smart design. An open floor plan creates a bright, welcoming space where the living, dining, and kitchen areas flow effortlessly—perfect for everyday living and easy entertaining. The fully fenced backyard adds privacy and flexibility, ideal for pets, play, or quiet evenings outdoors. Whether you're stepping into homeownership

  Libby VanMeter Marshall Lane Real Estate - Lexington

  10 Pocahontas Trail, Winchester, KY 40391
• 

  

  /28

  $131,000 Sold Mar 12, 2026

  46 Judy Ann Ct, Winchester, KY 40391

  • 2 Beds
  • 1.5 Baths
  • 960 Sq Ft

  Last Sold Summary

  • 3% Below List Price
  • $136/SF
  • 0 Days On Market

  Current Estimated Value $148,072

  Last Listing Agent Lukas Owens The Brokerage

  46 Judy Ann Ct, Winchester, KY 40391
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  /4

  Est $96,967 Not Listed For Sale

  Unlisted Address

  • 2 Beds
  • 1 Bath
  • 940 Sq Ft
  • Built 1940

  Unlisted Address

  Last Sold Summary

  • 203% Above List Price
  • $34/SF

  Last Sold Price $32,000

  Last Listing Agent Null Non-Member Non-Member Office
• 

  /2

  $110,000

  • Land
  • 0.35 Acre
  • $314,286 per Acre

  150 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

  150 Duclair Dr, Winchester, KY 40391
• 

  

  /4

  $315,000 Sold Jun 30, 2025

  4550 Schollsville Rd Unit 40391, Winchester, KY 40391

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Mila Ensor Ensor Real Estate, LLC

  4550 Schollsville Rd Unit 40391, Winchester, KY 40391
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  /41

  Est $201,360 Not Listed For Sale

  31 Watts Rd, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,343 Sq Ft
  • Built 1960

  31 Watts Rd, Winchester, KY 40391

  Last Sold Summary

  • 1% Above List Price
  • $149/SF
  • 24 Days On Market

  Last Sold Price $200,000

  Last Listing Agent Christa Joynt Keller Williams Commonwealth
• 

  

  /21

  $244,900

  • 3 Beds
  • 1.5 Baths
  • 1,494 Sq Ft

  720 Estes Dr, Winchester, KY 40391

  This charming brick ranch is truly move-in ready. Offering 3 bedrooms, 1.5 baths, a welcoming living room, a cozy den, and kitchen with appliances, this home blends comfort and convenience with ease. Enjoy the natural light and peaceful views from the screened-in sunporch, perfect for relaxing. Updates include new kitchen flooring, refinished hardwood floors, and updated trim that gives the home

  Jonathan Wood HomeLand Real Estate Inc - Mt Sterling

  720 Estes Dr, Winchester, KY 40391
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  /33

  $270,000 Sold Mar 28, 2025

  129 Ashley Dr, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,884 Sq Ft
  • Built 1993

  Last Sold Summary

  • $143/SF
  • 8 Days On Market

  Current Estimated Value $289,281

  Last Listing Agent Audra Tate National Real Estate

  129 Ashley Dr, Winchester, KY 40391

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