Homes in ZIP Code 40391

• 

  

  

  /15

  $110,000

  Sold Sep 04, 2025

  706 Williamsburg Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 924 Sq Ft
  • Built 2024

  Last Sold Summary

  • 21% Below List Price
  • $119/SF

  Current Estimated Value $118,458

  Last Listing Agent Andrew Fugitt KY Property Hunters

  706 Williamsburg Dr, Winchester, KY 40391
• 

  

  

  /38

  Est $298,125

  Not Listed For Sale

  2020 Two Mile Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,320 Sq Ft
  • Built 1950

  2020 Two Mile Rd, Winchester, KY 40391

  Last Sold Summary

  • 37 Days On Market
• 

  

  

  /37

  $1,575,000

  $20K PRICE DROP

  • 37 Beds
  • 19.5 Baths
  • 26,124 Sq Ft

  2 N Main St, Winchester, KY 40391

  Major CAPEX in 2022 & 2024 — Facade transformation, fully restored and renovated.Current grossing $168,000 annual rent, with $4,000/month upside — beats the 1% rule! The Kerr Building, the largest downtown historical landmark, features structural repairs, new roofing, brick tuck-pointing, secure key-fob entrances, central HVAC, modern kitchens, updated baths, and new flooring. 18 LIHTC

  Blanca Cheung Tsubaki Group, LLC

  2 N Main St, Winchester, KY 40391
• 

  

  

  /30

  $185,000

  Sold Feb 06, 2026

  40 Garner St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,354 Sq Ft
  • Built 1950

  Last Sold Summary

  • 16% Below List Price
  • $137/SF
  • 217 Days On Market

  Current Estimated Value $195,462

  Last Listing Agent Nicole Seals Guide Realty, Inc.

  40 Garner St, Winchester, KY 40391
• 

  

  

  /13

  Est $189,291

  Not Listed For Sale

  4 Burton Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,330 Sq Ft
  • Built 1948

  4 Burton Ave, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market
• 

  

  /4

  $625,000

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,405 Sq Ft

  424 Alexis Way, Winchester, KY 40391

  Introducing the Castleton, a stunning home designed to impress in the sought-after Mallard Cove neighborhood. This exquisite floor plan features a side-turned garage and captivating curb appeal with double front entry doors. Inside, you'll find a thoughtfully designed split-bedroom layout with a spacious primary suite that includes a luxurious ensuite with a walk-in closet, double vanity, tile

  Shane Underwood Keller Williams Commonwealth

  424 Alexis Way, Winchester, KY 40391
• 

  

  /36

  $435,000

  Sold May 22, 2026

  3886 Jackson Ferry Rd, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,692 Sq Ft
  • Built 1992

  Last Sold Summary

  • $257/SF
  • 21 Days On Market

  Current Estimated Value $429,866

  Last Listing Agent Whitney Ensor Ensor Real Estate, LLC

  3886 Jackson Ferry Rd, Winchester, KY 40391
• 

  

  /19

  Est $199,366

  Not Listed For Sale

  223 Blair Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,025 Sq Ft

  223 Blair Ave, Winchester, KY 40391

  Last Sold Summary

  • 82 Days On Market
• 

  

  /25

  $255,000

  $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,809 Sq Ft

  316 Maryland Ave, Winchester, KY 40391

  Brick ranch on a partially finished basement offering 3 bedrooms and 2 full baths! The main level welcomes you into a comfortable living room featuring a masonry wood-burning fireplace, along with a spacious kitchen, all three bedrooms, and a full bath located down the hall. The kitchen provides access to the basement where you'll find additional living space in the cozy den area complete with a

  Michelle Blackburn RE/MAX Creative, Winchester

  316 Maryland Ave, Winchester, KY 40391
• 

  

  /19

  $189,000

  Sold Mar 03, 2026

  111 Quail Ridge Rd, Winchester, KY 40391

  • 2 Beds
  • 2.5 Baths
  • 1,197 Sq Ft
  • Built 1994

  Last Sold Summary

  • $158/SF
  • 5 Days On Market

  Current Estimated Value $193,189

  Last Listing Agent Kim Dice eXp Realty, LLC

  111 Quail Ridge Rd, Winchester, KY 40391
• 

  

  /26

  Est $193,286

  Not Listed For Sale

  64 Bond Ct, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,025 Sq Ft
  • Built 1987

  64 Bond Ct, Winchester, KY 40391

  Last Sold Summary

  • 18 Days On Market
• 

  

  /14

  $1,115,000

  • Land
  • 120 Acres
  • $9,292 per Acre

  345 Providence Ln, Winchester, KY 40391

  Possible option to purchase the full 202 acres! Rare opportunity to own approximately 120 acres of beautiful rolling farmland in Clark County! This versatile property offers a mix of cleared pasture and wooded acreage, ideal for cattle, horses, recreation, or your dream homestead. Including a large pond plus county water available at the road this property is well-suited for agricultural use. The

  Megan McCoy Keller Williams Legacy Group

  345 Providence Ln, Winchester, KY 40391
• 

  

  /35

  $244,000

  Sold Mar 09, 2026

  426 Paisley Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,641 Sq Ft
  • Built 2004

  Last Sold Summary

  • $149/SF
  • 2 Days On Market

  Current Estimated Value $247,320

  Last Listing Agent Lura Justice Rector Hayden Realtors

  426 Paisley Ct, Winchester, KY 40391
• 

  

  /22

  Est $187,480

  Not Listed For Sale

  101 Baldwin Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 925 Sq Ft

  101 Baldwin Ave, Winchester, KY 40391

  Last Sold Summary

  • 2 Days On Market
• 

  

  /14

  $180,000

  • 4 Beds
  • 3 Baths
  • 3,462 Sq Ft

  229 S Highland St, Winchester, KY 40391

  Investor special with historic charm on corner lot! Opportunity awaits with this spacious 5 bedroom, 3 full bath home offering 3,462 sq ft of potential. Situated on a corner lot and walkable to downtown, this classic 2 story property is rich in character, featuring original hardwood floors, detailed woodwork, a welcoming front porch with columns, and a striking staircase with stained glass

  Michelle Blackburn RE/MAX Creative, Winchester

  229 S Highland St, Winchester, KY 40391
• 

  

  /22

  $220,000

  Sold Mar 31, 2026

  443 Jameson Way, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 2002

  Last Sold Summary

  • 1% Below List Price
  • $157/SF
  • 64 Days On Market

  Current Estimated Value $225,098

  Last Listing Agent Tyler I Back The Brokerage

  443 Jameson Way, Winchester, KY 40391
• 

  

  /28

  Est $239,664

  Not Listed For Sale

  916 Muddy Creek Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,000 Sq Ft
  • Built 1943

  916 Muddy Creek Rd, Winchester, KY 40391

  Last Sold Summary

  • 39 Days On Market
• 

  

  /55

  $515,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,563 Sq Ft

  935 Stoner-Ephesus Rd, Winchester, KY 40391

  Picture this: over five acres of Kentucky countryside, a handsome ranch-style home, and enough elbow room to finally breathe. This stunning 2,563 square foot retreat delivers the rare combination of refined interior finishes and genuine rural charm, all without sacrificing modern convenience. Inside, discover a generous family room anchored by a striking stone fireplace — the kind of space that

  Timothy Saylor Threshold Real Estate Services

  935 Stoner-Ephesus Rd, Winchester, KY 40391
• 

  /2

  $160,000

  Sold Sep 19, 2025

  8 Village Dr, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,414 Sq Ft
  • Built 1970

  Last Sold Summary

  • 9% Below List Price
  • $113/SF
  • 0 Days On Market

  Current Estimated Value $279,726

  Last Listing Agent Joyce Ratliff Tom Goebel & Company

  8 Village Dr, Winchester, KY 40391
• 

  

  /21

  Est $218,862

  Not Listed For Sale

  17 Elizabeth St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,450 Sq Ft
  • Built 1950

  17 Elizabeth St, Winchester, KY 40391

  Last Sold Summary

  • 24 Days On Market
• 

  

  /14

  $269,900

  • 3 Beds
  • 1 Bath
  • 1,644 Sq Ft

  205 Providence Ln, Winchester, KY 40391

  You Wont Find A More Beautiful And Private Setting!!! This Home Features 3 Bedrooms And 1 Bath And Sits On 5.05 Acres; Two Front Porches; Large Rear Porch; A Separate Room Downstairs That Would Make A Great Master Bedroom/Suite Potentially; Huge Mudroom/Flex Space! Possibilities Are Endless With This Property. This Home Has Replacement Vinyl Clad Windows, Roof And HVAC All Replaced In Last 10

  Patrick Arvin Keller Williams Commonwealth

  205 Providence Ln, Winchester, KY 40391
• 

  

  /5

  $175,000

  Sold Jun 11, 2026

  5105 Combs Ferry Rd, Ford, KY 40391

  • Land
  • 6.1 Acres
  • $28,693 per Acre

  Last Sold Summary

  • 61% Below List Price
  • 88 Days On Market

  Last Listing Agent John Martin EXIT Realty Crutcher Frankfort

  5105 Combs Ferry Rd, Ford, KY 40391
• 

  

  /20

  Est $244,759

  Not Listed For Sale

  1121 Muddy Creek Rd, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,498 Sq Ft
  • Built 1940

  1121 Muddy Creek Rd, Winchester, KY 40391

  Last Sold Summary

  • 9 Days On Market
• 

  

  /35

  $289,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,240 Sq Ft

  110 Buckingham Ln, Winchester, KY 40391

  The original buyer's plans changed, and their loss may be your second chance. This beautiful Winchester ranch is the kind of home buyers walk into and immediately feel good about. From the vaulted ceilings and incredibly beautiful luxury vinyl plank flooring to the updated bathrooms, well-maintained systems, epoxied garage floor, and easy one-level layout, this home is truly move-in ready and

  Jeremy Perryman United Real Estate Bluegrass

  110 Buckingham Ln, Winchester, KY 40391
• 

  

  /28

  $290,000

  Sold Apr 17, 2026

  24 N Burns Ave, Winchester, KY 40391

  • 3 Beds
  • 3.5 Baths
  • 2,526 Sq Ft
  • Built 1920

  Last Sold Summary

  • 6% Below List Price
  • $115/SF
  • 92 Days On Market

  Current Estimated Value $289,691

  Last Listing Agent Sarah Hess Keller Williams Commonwealth

  24 N Burns Ave, Winchester, KY 40391
• 

  

  /79

  Est $221,634

  Not Listed For Sale

  205 French Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 946 Sq Ft
  • Built 1959

  205 French Ave, Winchester, KY 40391

  Last Sold Summary

  • 319 Days On Market
• 

  

  /5

  $575,000

  • Land
  • 1.71 Acres
  • $336,257 per Acre

  1025 Colby Rd, Winchester, KY 40391

  This 1.7+/- acre parcel represents an excellent opportunity for almost any commercial application. The property has 397 feet of frontage along busy Colby Road (9,170 AADT, 2015) near its intersection with the Winchester Bypass (23,200 AADT, 2011). Located in the main shopping corridor of Clark County, this property receives tons of exposure and traffic from the adjacent Walmart Super-center,

  Jo Gawthrop Keller Williams Bluegrass Realty

  1025 Colby Rd, Winchester, KY 40391
• 

  

  /101

  $1,050,000

  Sold Jun 01, 2026

  3760 Old Boonesboro Rd, Winchester, KY 40391

  • 5 Beds
  • 5 Baths
  • 5,666 Sq Ft
  • Built 1985

  Last Sold Summary

  • 19% Below List Price
  • $185/SF
  • 15 Days On Market

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  3760 Old Boonesboro Rd, Winchester, KY 40391
• 

  

  /24

  Est $211,559

  Not Listed For Sale

  5 Kentucky St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,634 Sq Ft
  • Built 1930

  5 Kentucky St, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market
• 

  

  /55

  $350,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,835 Sq Ft

  27 Hampton Ave, Winchester, KY 40391

  Located on desirable Hampton Avenue, this all-brick ranch is full of timeless character and thoughtful updates. Beautiful original hardwood floors run throughout the main level, highlighted by detailed craftsmanship and charm you don't find every day. The spacious living room features built-ins, a fireplace, and flows into the dining area, creating a warm and inviting space for everyday living or

  Terra Long Keller Williams Commonwealth

  27 Hampton Ave, Winchester, KY 40391
• 

  /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
• 

  

  /23

  Est $200,246

  Not Listed For Sale

  11 Kentucky St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,708 Sq Ft
  • Built 1920

  11 Kentucky St, Winchester, KY 40391

  Last Sold Summary

  • 9 Days On Market
• 

  

  /15

  $925,000

  • Land
  • 3.77 Acres
  • $245,358 per Acre

  300 Rolling Hills Ln, Winchester, KY 40391

  Great location just off exit 96 on I-64 and easy access to the Mountain Parkway. Only 15 minutes from I-75. Located near the entrance to the Winchester Kentucky Industrial Park. 3.774 flat acres to build your next business location.

  Josh Wood Freedom Realty & Property Management

  300 Rolling Hills Ln, Winchester, KY 40391
• 

  

  /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 $899,501

  Last Listing Agent Greg Leveridge Block + Lot Homes

  511 Boone Ave, Winchester, KY 40391
• 

  

  /18

  Est $119,996

  Not Listed For Sale

  129 Kentucky St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,080 Sq Ft
  • Built 1940

  129 Kentucky St, Winchester, KY 40391

  Last Sold Summary

  • 46 Days On Market
• 

  /2

  $168,500

  Pending

  • 3 Beds
  • 2 Baths
  • 1,026 Sq Ft

  12 Apache Trail, Winchester, KY 40391

  Welcome to this charming 3-bedroom, 2-full bath ranch located in the desirable Indian Hills Subdivision! This home features a large covered front porch, perfect for relaxing and enjoying your morning coffee or evening sunsets. Inside, you'll find a spacious layout with plenty of potential to make it your own. The full unfinished basement offers endless possibilities for storage, a home gym, or

  Stephen Brashear Keller Williams Commonwealth

  12 Apache Trail, Winchester, KY 40391
• 

  

  /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 $426,173

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate

  134 Fontaine Blvd, Winchester, KY 40391
• 

  

  /15

  Est $207,349

  Not Listed For Sale

  20 Elizabeth St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,258 Sq Ft
  • Built 1940

  20 Elizabeth St, Winchester, KY 40391

  Last Sold Summary

  • 7 Days On Market
• 

  

  /50

  $545,000

  665 Lillies Ferry Rd, Winchester, KY 40391

  You do not want to sleep on this one, it is a beautiful working farm with multiple building sites and amazing views and tranquility. Two farms are selling together for a total of 91.28 acres that is already a very productive cattle farm. The fencing, gates, waterers and infrastructure is already in place to move right in and produce income. There are multiple possible building sites with amazing

  Carrie Taylor Taylor Real Estate, LLC

  665 Lillies Ferry Rd, Winchester, KY 40391
• 

  

  /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 $310,871

  Last Listing Agent Lucy Martin Jenkins United Real Estate Bluegrass

  1996 White Conkwright Rd, Winchester, KY 40391

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