Homes in ZIP Code 40391

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  /86

  $515,000 Sold Apr 17, 2026

  125 Casa Landa Way, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 3,848 Sq Ft
  • Built 1999

  Last Sold Summary

  • 6% Below List Price
  • $134/SF
  • 88 Days On Market

  Current Estimated Value $526,775

  Last Listing Agent Maggie Napier Napier Realtors

  125 Casa Landa Way, Winchester, KY 40391
• 

  

  

  /17

  Est $306,999 Not Listed For Sale

  129 S Highland St, Winchester, KY 40391

  • 6 Beds
  • 4 Baths
  • 3,608 Sq Ft
  • Built 1940

  129 S Highland St, Winchester, KY 40391

  Last Sold Summary

  • 14% Above List Price
  • $75/SF
  • 86 Days On Market

  • Last Sold Price $269,000
  • Jan 31, 2025

  Last Listing Agent Joshua Lynch The Brokerage
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  /37

  $1,575,000

  • 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
• 

  

  

  /27

  $269,000 Sold Apr 20, 2026

  916 Stratton Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1988

  Last Sold Summary

  • $192/SF
  • 0 Days On Market

  Current Estimated Value $262,927

  Last Listing Agent Joshua Davis The Agency

  916 Stratton Ln, Winchester, KY 40391
• 

  

  

  /17

  Est $168,633 Not Listed For Sale

  21 Franklin Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,006 Sq Ft
  • Built 1940

  21 Franklin Ave, Winchester, KY 40391

  Last Sold Summary

  • 30% Above List Price
  • $129/SF
  • 1 Day On Market

  • Last Sold Price $130,000
  • Apr 30, 2024

  Last Listing Agent Austin Polley The Polley Group
• 

  

  /16

  $160,000

  • 3 Beds
  • 1 Bath
  • 1,097 Sq Ft

  220 E Washington St, Winchester, KY 40391

  Investors take note, tenant occupied home, 3 bedrooms, 1 bathroom, one level living! Flippers, downsizing, or First-time buyers get ready! Wood style floors, covered front porch, back yard with patio...Do not miss an opportunity to add to your rental portfolio investment, start your real estate adventure, or make this home your own! Home is occupied 24-hour notice is required to show.

  Whitney Ensor Ensor Real Estate, LLC

  220 E Washington St, Winchester, KY 40391
• 

  

  /65

  $385,000 Sold Dec 11, 2025

  1731 Ford Hampton Rd, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,111 Sq Ft
  • Built 2001

  Last Sold Summary

  • 27% Below List Price
  • $182/SF
  • 157 Days On Market

  Current Estimated Value $399,267

  Last Listing Agent Julie Wiggington RE/MAX Creative, Winchester

  1731 Ford Hampton Rd, Winchester, KY 40391
• 

  

  /23

  Est $173,545 Not Listed For Sale

  353 E Broadway St, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,905 Sq Ft
  • Built 1940

  353 E Broadway St, Winchester, KY 40391

  Last Sold Summary

  • 163% Above List Price
  • $35/SF
  • 1 Day On Market

  • Last Sold Price $66,000
  • Aug 02, 2023

  Last Listing Agent Keith Wilson Coldwell Banker McMahan
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  /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
• 

  

  /79

  $584,900 Sold Feb 17, 2026

  180 Casa Landa Way, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 4,779 Sq Ft
  • Built 2000

  Last Sold Summary

  • 10% Below List Price
  • $122/SF
  • 46 Days On Market

  Current Estimated Value $586,388

  Last Listing Agent Janna Chalfant Smith United Real Estate Bluegrass

  180 Casa Landa Way, Winchester, KY 40391
• 

  

  /53

  Est $99,572 Not Listed For Sale

  307 Jackson St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,629 Sq Ft
  • Built 1950

  307 Jackson St, Winchester, KY 40391

  Last Sold Summary

  • 24% Above List Price
  • $49/SF
  • 67 Days On Market

  • Last Sold Price $80,000
  • Apr 30, 2025

  Last Listing Agent Josh Wood Freedom Realty & Property Management
• 

  

  /19

  $235,000

  • 3 Beds
  • 2 Baths
  • 1,502 Sq Ft

  357 Silverton Way, Winchester, KY 40391

  This updated home offers easy access to I-64 and downtown Winchester. See ceiling fans in every room, upstairs bonus room, modern lighting in the kitchen and bath, and new appliances, countertops, and backsplash. Enjoy a peaceful, quiet neighborhood and a relaxing rural view from the backyard. A clean, comfortable, move-in-ready home with thoughtful upgrades throughout.

  Frank Mulder Tru Life Real Estate

  357 Silverton Way, Winchester, KY 40391
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  /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 $113,841

  Last Listing Agent Andrew Fugitt Coldwell Banker McMahan

  706 Williamsburg Dr, Winchester, KY 40391
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  /32

  Est $189,143 Not Listed For Sale

  230 Winn Ave, Winchester, KY 40391

  • 4 Beds
  • 1.5 Baths
  • 1,400 Sq Ft
  • Built 1940

  230 Winn Ave, Winchester, KY 40391

  Last Sold Summary

  • 5% Above List Price
  • $128/SF
  • 73 Days On Market

  • Last Sold Price $179,500
  • Jan 19, 2024

  Last Listing Agent Cindy Walker Sandy Stuart Realty
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  /13

  $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
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  /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 $191,635

  Last Listing Agent Nicole Seals Guide Realty, Inc.

  40 Garner St, Winchester, KY 40391
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  /17

  Est $170,902 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

  • 35% Above List Price
  • $133/SF
  • 0 Days On Market

  • Last Sold Price $127,000
  • Aug 01, 2023

  Last Listing Agent Lyndsey Ryles Kentucky Elite Real Estate
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  /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
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  /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 $191,141

  Last Listing Agent Kim Dice EXP Realty, LLC

  111 Quail Ridge Rd, 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
  • Dec 04, 2023

  Last Listing Agent Amanda Stewart Stewart & Co Realty LLC
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  /55

  $525,000

  • 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
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  /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 $242,717

  Last Listing Agent Lura Justice Rector Hayden Realtors

  426 Paisley Ct, Winchester, KY 40391
• 

  

  /27

  Est $193,487 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

  • 19% Above List Price
  • $116/SF
  • 30 Days On Market

  • Last Sold Price $162,000
  • Oct 24, 2024

  Last Listing Agent O. Debbie Pennington CENTURY 21 Advantage Realty
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  /15

  $139,000 Pending

  • 2 Beds
  • 1 Bath
  • 904 Sq Ft

  37 Ashland Ave, Winchester, KY 40391

  Ideal for first-time buyers, downsizers, or investors. This move-in ready 2-bedroom home features a fenced backyard, off-street parking, and a detached storage building, all in a convenient Winchester location.

  Samantha Gray National Real Estate

  37 Ashland Ave, 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 $222,350

  Last Listing Agent Tyler I Back The Brokerage

  443 Jameson Way, Winchester, KY 40391
• 

  

  /23

  Est $211,803 Not Listed For Sale

  42 Park Ave, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,129 Sq Ft
  • Built 1940

  42 Park Ave, Winchester, KY 40391

  Last Sold Summary

  • 8% Above List Price
  • $174/SF
  • 54 Days On Market

  • Last Sold Price $197,000
  • Mar 31, 2025

  Last Listing Agent Jonathan McMahan Coldwell Banker McMahan
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  /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
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  /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 $277,556

  Last Listing Agent Joyce Ratliff Tom Goebel & Company

  8 Village Dr, Winchester, KY 40391
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  /43

  Est $150,279 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

  • 39% Above List Price
  • $69/SF
  • 23 Days On Market

  • Last Sold Price $108,500
  • Nov 25, 2024

  Last Listing Agent Christa Joynt Keller Williams Commonwealth
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  /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
• 

  

  /22

  $193,000 Sold Jun 06, 2025

  116 Linden Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,164 Sq Ft
  • Built 1945

  Last Sold Summary

  • 2% Below List Price
  • $166/SF
  • 3 Days On Market

  Current Estimated Value $198,739

  Last Listing Agent Jeremy Perryman United Real Estate Bluegrass

  116 Linden Ave, Winchester, KY 40391
• 

  

  /26

  Est $250,131 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
  • Apr 08, 2024

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

  /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
• 

  

  /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 $295,524

  Last Listing Agent Sarah Hess Keller Williams Commonwealth

  24 N Burns Ave, Winchester, KY 40391
• 

  

  /25

  Est $213,327 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

  • 4% Above List Price
  • $190/SF
  • 0 Days On Market

  • Last Sold Price $204,900
  • Aug 30, 2024

  Last Listing Agent Kymberly McCreary EXP Realty, LLC
• 

  /2

  $110,000

  • Land
  • 11,761 Sq Ft
  • $407,407 per Acre

  125 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

  125 Jacob Ct, 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
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  /39

  Est $266,961 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

  • 14% Above List Price
  • $108/SF
  • 21 Days On Market

  • Last Sold Price $235,000
  • Jan 26, 2024

  Last Listing Agent Joshua Lynch The Brokerage
• 

  

  /7

  $800,000 Pending

  • Land
  • 4.87 Acres
  • $164,271 per Acre

  1108 W Lexington Ave, Winchester, KY 40391

  Rare opportunity to purchase a large multi-family development in the heart of Winchester! Directly across the street from Legacy Grove Park! All building and engineering plans included to build 66 approved townhomes with the possibility of adding 4 more. Currently zoned PD (Planned Development), could possibly be changed to commercial due to neighboring commercial property. Main property is 4.87

  Jason Townsend Kentucky Residential Real Estate, LLC

  1108 W Lexington Ave, 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 $908,797

  Last Listing Agent Greg Leveridge Block + Lot Real Estate

  511 Boone Ave, Winchester, KY 40391

Showing Results 481 - 520, Page 13 of 18