Homes in ZIP Code 40391

• 

  

  

  /41

  $247,000 Sold Sep 19, 2025

  3588 Stamper Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,530 Sq Ft
  • Built 1987

  Last Sold Summary

  • 1% Below List Price
  • $161/SF
  • 4 Days On Market

  Current Estimated Value $246,450

  Last Listing Agent Zach Johnson The Brokerage

  3588 Stamper Dr, Winchester, KY 40391
• 

  

  

  /58

  Est $197,873 Not Listed For Sale

  219 Locust Grove Rd, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,191 Sq Ft
  • Built 1955

  219 Locust Grove Rd, Winchester, KY 40391

  Last Sold Summary

  • 10% Above List Price
  • $151/SF
  • 27 Days On Market

  • Last Sold Price $180,000
  • Sep 24, 2024

  Last Listing Agent Josh Wood Freedom Realty & Property Management
• 

  

  

  /4

  $64,900 Pending

  • Land
  • 27,878 Sq Ft
  • $101,406 per Acre

  102 Royal Oak Dr, Winchester, KY 40391

  A Unique Opportunity to Build your Dream Home in the Estate Section of Royal Oaks in Clark County. Situated on..64 acres of land and Conveniently located off Exit 96 on I-64, with close proximity to the Industrial Park, Shopping, Dining and downtown Winchester. Call listing agent for additional details and information on the few lots left to build on in this subdivision!

  Melia Hord Keller Williams Legacy Group

  102 Royal Oak Dr, Winchester, KY 40391
• 

  

  

  /20

  $205,000 Sold Aug 19, 2025

  202 Custer Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,113 Sq Ft
  • Built 1999

  Last Sold Summary

  • 8% Above List Price
  • $184/SF
  • 2 Days On Market

  Current Estimated Value $198,068

  Last Listing Agent Brittany Beer EXP Realty, LLC

  202 Custer Ct, Winchester, KY 40391
• 

  

  

  /29

  Est $202,098 Not Listed For Sale

  505 Bob o Link Dr, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,228 Sq Ft
  • Built 1960

  505 Bob o Link Dr, Winchester, KY 40391

  Last Sold Summary

  • 22% Above List Price
  • $134/SF
  • 22 Days On Market

  • Last Sold Price $165,000
  • Sep 15, 2023

  Last Listing Agent Kathryn Cheuvront Coldwell Banker McMahan
• 

  

  /8

  $1,500,000

  1015 Old Stone Church Rd, Winchester, KY 40391

  Right off of Boonesboro Road lies 60.65± acres of Kentucky history waiting for its next chapter! This remarkable property sits along historic Howard's Creek and is located on the site of the original Bush Settlement—one of the earliest settlements in Kentucky. Formerly a working tobacco farm, this versatile acreage offers opportunities for cattle, hay, or crops, with timber and mineral rights

  Walker Mack Bluegrass Property Exchange

  1015 Old Stone Church Rd, Winchester, KY 40391
• 

  

  /15

  $176,000 Sold Oct 17, 2025

  7575 Irvine Rd, Winchester, KY 40391

  Last Sold Summary

  • 6% Below List Price
  • 2 Days On Market

  Current Estimated Value $182,091

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  7575 Irvine Rd, Winchester, KY 40391
• 

  

  /12

  Est $218,852 Not Listed For Sale

  303 Hummingbird Rd, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,169 Sq Ft
  • Built 1960

  303 Hummingbird Rd, Winchester, KY 40391

  Last Sold Summary

  • 16% Above List Price
  • $162/SF
  • 27 Days On Market

  • Last Sold Price $189,000
  • Dec 13, 2023

  Last Listing Agent Garry Milton Milton and Associates Real Estate
• 

  

  /87

  $2,999,000

  • 6 Beds
  • 5 Baths
  • 3,693 Sq Ft

  3049 Ironworks Rd, Winchester, KY 40391

  Some properties are special simply because of the story behind them. This 150-acre farm in Winchester has been cared for by the same family since 1803, and it's now being offered for sale for the very first time. The land is classic Kentucky countryside, rolling pastures, peaceful water, and wide open views in every direction. Four ponds and a gently flowing creek bring both beauty and function

  Zova Rothchild Keller Williams Legacy Group

  3049 Ironworks Rd, Winchester, KY 40391
• 

  

  /40

  $400,000 Sold May 23, 2025

  109 Monet Blvd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,432 Sq Ft
  • Built 1995

  Last Sold Summary

  • 5% Below List Price
  • $164/SF
  • 26 Days On Market

  Current Estimated Value $428,550

  Last Listing Agent Melissa Brown Keller Williams Legacy Group

  109 Monet Blvd, Winchester, KY 40391
• 

  

  /7

  Est $188,705 Not Listed For Sale

  301 Hummingbird Rd, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,106 Sq Ft
  • Built 1955

  301 Hummingbird Rd, Winchester, KY 40391

  Last Sold Summary

  • 36% Above List Price
  • $126/SF
  • 41 Days On Market

  • Last Sold Price $139,000
  • Oct 26, 2023

  Last Listing Agent Garry Milton Milton and Associates Real Estate
• 

  

  /33

  $354,900 Pending

  • 5 Beds
  • 2 Baths
  • 1,952 Sq Ft

  1270 Sewell Shop Rd, Winchester, KY 40391

  Country Living with Convenience — 5 Fenced Acres in Winchester, KY Enjoy the perfect blend of peaceful country living and easy access to town with this well-maintained home on 5 fully fenced acres in Winchester, KY. Conveniently located just 30 minutes to Lexington, 5 miles to I-64, 10 minutes to Mt. Sterling, and 15 minutes to Winchester, this property offers country living without sacrificing

  Meggan Batey Keller Williams Legacy Group

  1270 Sewell Shop Rd, Winchester, KY 40391
• 

  

  /10

  $325,000 Sold Aug 29, 2025

  210 Cabin Creek Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,584 Sq Ft
  • Built 1999

  Last Sold Summary

  • $205/SF

  Current Estimated Value $333,976

  Last Listing Agent Janine Shackelford LPT Realty

  210 Cabin Creek Rd, Winchester, KY 40391
• 

  

  /30

  Est $174,459 Not Listed For Sale

  222 Locust Grove Rd, Winchester, KY 40391

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

  222 Locust Grove Rd, Winchester, KY 40391

  Last Sold Summary

  • 29% Above List Price
  • $151/SF
  • 2 Days On Market

  • Last Sold Price $135,000
  • Nov 01, 2023

  Last Listing Agent Michelle Blackburn RE/MAX
• 

  

  /21

  $180,000

  • Land
  • 10.05 Acres
  • $17,919 per Acre

  3925 Jackson Ferry Rd, Winchester, KY 40391

  This 10.045-acre tract offers the total package...scenic surroundings, river access, and improvements already in place. Situated along a quiet, picturesque drive, the property features a solid barn that has recently been painted and structurally reinforced, adding both character and functionality. With a picturesque build site available, this land is ready for your dream home, hobby farm, and

  Christa Joynt Keller Williams Commonwealth

  3925 Jackson Ferry Rd, Winchester, KY 40391
• 

  

  /77

  $464,900 Sold Jun 09, 2025

  275 Runnymeade Dr, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,495 Sq Ft
  • Built 2017

  Last Sold Summary

  • $186/SF
  • 21 Days On Market

  Current Estimated Value $467,373

  Last Listing Agent Tyson Walters Kassie & Associates

  275 Runnymeade Dr, Winchester, KY 40391
• 

  

  /31

  Est $219,668 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

  • 7% Above List Price
  • $137/SF
  • 9 Days On Market

  • Last Sold Price $205,000
  • Aug 23, 2024

  Last Listing Agent Shane Underwood Keller Williams Commonwealth
• 

  

  /16

  $1,200,000

  • 16 Beds
  • 16 Baths
  • 7,480 Sq Ft

  16 Linden Ave, Winchester, KY 40391

  You won't want to miss adding this income-producing apartment complex to your portfolio. This property is comprised of 16 one-bedroom/one-bathroom apartments with 100% occupancy. Complex is conveniently located in downtown Winchester and only 20 minutes from Lexington via easy highway access. The building sits on a 0.34 acre lot with 20+ parking spaces. Property has several updates including roof

  Kevin Bradley KB Realty Group

  16 Linden Ave, Winchester, KY 40391
• 

  

  /36

  $261,000 Sold Feb 04, 2026

  433 Wellington Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,234 Sq Ft
  • Built 2010

  Last Sold Summary

  • 2% Below List Price
  • $212/SF
  • 60 Days On Market

  Current Estimated Value $259,677

  Last Listing Agent Nick Ratliff Realty Team - Nicholas Ratliff Real Broker LLC

  433 Wellington Way, Winchester, KY 40391
• 

  

  /18

  Est $159,092 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

  • 22% Above List Price
  • $144/SF
  • 0 Days On Market

  • Last Sold Price $130,000
  • May 11, 2023

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC
• 

  

  /3

  $380,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,677 Sq Ft

  270 Evergreen Dr, Winchester, KY 40391

  Welcome to The Run for the Roses - a thoughtfully designed proposed construction home located in the desirable Locust Hill Acres community. This charming home offers an open concept floor plan perfect for modern living, featuring 3 spacious bedrooms and 2 full bathrooms on unfinished walkout basement.The large primary suite is a true retreat, complete with a generously sized walk-in closet

  Rex Hall United Real Estate Bluegrass

  270 Evergreen Dr, Winchester, KY 40391
• 

  /2

  $180,000 Sold Jul 01, 2025

  23 Meadowbrook Dr, Winchester, KY 40391

  • 4 Beds
  • 4 Baths
  • 2,250 Sq Ft
  • Built 1953

  Last Sold Summary

  • $80/SF

  Current Estimated Value $208,937

  Last Listing Agent A. Rebecca Woods Woods Realty Group

  23 Meadowbrook Dr, Winchester, KY 40391
• 

  

  /10

  Est $195,311 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

  • 22% Above List Price
  • $126/SF
  • 1 Day On Market

  • Last Sold Price $159,900
  • Aug 23, 2023

  Last Listing Agent Sondra Clark Taylor Real Estate, LLC
• 

  

  /31

  $195,000

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft

  5434 Pine Ridge Rd, Winchester, KY 40391

  Jim Woodrum RE/MAX Creative, Winchester

  5434 Pine Ridge Rd, Winchester, KY 40391
• 

  

  /7

  $55,000 Sold Nov 06, 2025

  76 Clay St, Winchester, KY 40391

  • 1,768 Sq Ft
  • Built 1945

  Last Sold Summary

  • $31/SF
  • 2 Days On Market

  Current Estimated Value $61,654

  Last Listing Agent Brian Lewis Guide Realty, Inc.

  76 Clay St, Winchester, KY 40391
• 

  

  /55

  Est $188,271 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

  • 13% Above List Price
  • $118/SF
  • 8 Days On Market

  • Last Sold Price $166,500
  • Jun 25, 2024

  Last Listing Agent Christa Joynt Keller Williams Commonwealth
• 

  

  /12

  $135,000

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft

  471 Goose Creek Rd, Winchester, KY 40391

  CASH BUYERS! This 3-bedroom, 2-bath manufactured home on 1.49 acres offers strong potential for those looking to renovate, rent, or resell. Property is being sold as-is and will require repairs, making it best suited for cash buyers. Located just minutes from I-64 and convenient to Lexington, this property combines rural privacy with accessibility — a desirable combination for future resale or

  Shari Frasure Keller Williams Commonwealth

  471 Goose Creek Rd, Winchester, KY 40391
• 

  

  /18

  $99,000 Sold Jun 17, 2025

  27 Oliver St, Winchester, KY 40391

  • 2 Beds
  • 2 Baths
  • 1,242 Sq Ft
  • Built 1940

  Last Sold Summary

  • 7% Below List Price
  • $80/SF
  • 8 Days On Market

  Current Estimated Value $105,706

  Last Listing Agent Daniel Ellis Metro Max Realty

  27 Oliver St, Winchester, KY 40391
• 

  

  /30

  Est $176,781 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

  • 18% Above List Price
  • $133/SF
  • 3 Days On Market

  • Last Sold Price $150,000
  • Oct 31, 2024

  Last Listing Agent Meredith Story Story Realty
• 

  

  /58

  $239,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,148 Sq Ft

  3610 Stamper Dr, Winchester, KY 40391

  You will absolutely love this well cared for and wonderfully updated ranch! This home has been lovingly cared for, is beautiful inside and out, and is absolutely ready to move into! Enjoy a large Eat-In kitchen with new granite countertops ( ten year warranty), and a marvelous, deep sink, stainless steel appliances, lots of cabinet space and more! You will find all new paint throughout the house

  Peter doCouto Plum Tree Realty

  3610 Stamper Dr, Winchester, KY 40391
• 

  

  /65

  $275,000 Sold Aug 15, 2025

  151 Hilltop Dr, Winchester, KY 40391

  • 4 Beds
  • 1.5 Baths
  • 1,873 Sq Ft
  • Built 1960

  Last Sold Summary

  • 1% Below List Price
  • $147/SF
  • 130 Days On Market

  Current Estimated Value $270,163

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  151 Hilltop Dr, Winchester, KY 40391
• 

  

  /32

  Est $198,871 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

  • 15% Above List Price
  • $91/SF
  • 17 Days On Market

  • Last Sold Price $173,000
  • Aug 23, 2024

  Last Listing Agent Andrew Fugitt Coldwell Banker McMahan
• 

  

  /10

  $775,000

  • Land
  • 2.6 Acres
  • $298,077 per Acre

  529 Bullion Blvd Unit 3B, Winchester, KY 40391

  Ideally located along the heart of Bypass Road (ADT: 24,801) in Winchester, Kentucky between and surrounding Kroger and Walmart shopping centers. These lots are offered as 1+ acres and may be subdivided.Winchester, KY is the county seat of Clark County, KY and is part of the Lexington-Fayette KY Metropolitan Statistical Area, and is supported by such industries such as Amazon, Ale-8-One,

  Greg Leveridge Block + Lot Real Estate

  529 Bullion Blvd Unit 3B, Winchester, KY 40391
• 

  

  /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 $257,627

  Last Listing Agent David Baesler Kentucky Dreams Realty

  206 Moss Cir, Winchester, KY 40391
• 

  

  /53

  Est $204,765 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

  • 107% Above List Price
  • $61/SF
  • 140 Days On Market

  • Last Sold Price $99,000
  • Jun 22, 2023

  Last Listing Agent Bob Sophiea eXp Realty, LLC
• 

  

  /11

  $50,000

  • Land
  • 17,859 Sq Ft
  • $121,951 per Acre

  308 Duclair Dr, Winchester, KY 40391

  Tucked away on a quiet cul-de-sac in Mallard Place, this .41-acre lot is ready for your vision. Imagine your dream home in a neighborhood known for its charm and convenience. Bring your house plans—your future starts here!

  Joseph Miller Keller Williams Legacy Group

  308 Duclair Dr, Winchester, KY 40391
• 

  

  /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 $565,782

  Last Listing Agent Shane Underwood Keller Williams Commonwealth

  426 Alexis Way, Winchester, KY 40391
• 

  

  /39

  Est $164,138 Not Listed For Sale

  10 Sylvania Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 953 Sq Ft
  • Built 1961

  10 Sylvania Ave, Winchester, KY 40391

  Last Sold Summary

  • 6% Above List Price
  • $163/SF
  • 207 Days On Market

  • Last Sold Price $155,000
  • Apr 24, 2025

  Last Listing Agent Christa Joynt Keller Williams Commonwealth
• 

  /2

  $14,100,000

  • Land
  • 274.52 Acres
  • $51,362 per Acre

  2395 Paris Rd, Winchester, KY 40391

  NOW PRE-SELLING: Deerlawn Development is Winchester, Ky's most anticipated residential development—an ambitious 274+-acre expansion formerly known as the well-established Royal Oaks/Plantation neighborhoods.
 Located at 2395 Paris Road, and positioned off I-64 at Exit 96 across from the rapidly expanding Industrial Park, Deerlawn is a master-planned community offering 438 single-family

  Melia Hord Keller Williams Legacy Group

  2395 Paris Rd, Winchester, KY 40391
• 

  

  /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 $341,605

  Last Listing Agent Geneva Wilder Stewart & Co Realty LLC

  401 Cedar Ct, Winchester, KY 40391

Showing Results 241 - 280, Page 7 of 18