Homes in ZIP Code 40391

• 

  

  /2

  $42,500 Pending

  • Land
  • 11,369 Sq Ft
  • $162,835 per Acre

  105 Bella Ct, Winchester, KY 40391

  Jo Gawthrop Keller Williams Bluegrass Realty

  105 Bella Ct, Winchester, KY 40391
• 

  

  

  /26

  $178,000 Sold Apr 30, 2026

  356 Colby Ridge Blvd, Winchester, KY 40391

  • 2 Beds
  • 1.5 Baths
  • 1,102 Sq Ft
  • Built 2003

  Last Sold Summary

  • 3% Below List Price
  • $162/SF
  • 51 Days On Market

  Current Estimated Value $184,047

  Last Listing Agent Nena Honaker Tom Goebel & Company

  356 Colby Ridge Blvd, Winchester, KY 40391
• 

  

  

  /25

  Est $237,651 Not Listed For Sale

  316 Jameson Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,625 Sq Ft
  • Built 1990

  316 Jameson Way, Winchester, KY 40391

  Last Sold Summary

  • 6% Above List Price
  • $138/SF
  • 140 Days On Market

  • Last Sold Price $225,000
  • Jan 19, 2024

  Last Listing Agent Jenny Bradley Rector Hayden Realtors
• 

  

  /2

  $110,000

  • Land
  • 13,939 Sq Ft
  • $343,750 per Acre

  250 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

  250 Duclair Dr, Winchester, KY 40391
• 

  

  /2

  $85,000 Sold Apr 15, 2026

  2465 Flanagan Station Rd, Winchester, KY 40391

  • Land
  • 3.68 Acres
  • $23,098 per Acre

  Last Sold Summary

  • 9 Days On Market

  Current Estimated Value $164,900

  Last Listing Agent Shari Frasure Keller Williams Commonwealth

  2465 Flanagan Station Rd, Winchester, KY 40391
• 

  

  /87

  Est $263,527 Not Listed For Sale

  418 Jameson Way, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,680 Sq Ft
  • Built 1996

  418 Jameson Way, Winchester, KY 40391

  Last Sold Summary

  • 5% Above List Price
  • $149/SF
  • 3 Days On Market

  • Last Sold Price $250,000
  • Apr 18, 2025

  Last Listing Agent Josh Wood Freedom Realty & Property Management
• 

  

  /21

  $139,000

  • 2 Beds
  • 1 Bath
  • 886 Sq Ft

  9 Linden Ave, Winchester, KY 40391

  Back on Market due to: Buyer's financing fell through. Very nice home with hardwood floors in main areas featuring 2 bedrooms, 1 bath, permanent stairs to attic that has windows and could possibly be 2 bedrooms or bonus room. Enjoy your coffee on the front porch in the mornings! The storage shed in the back yard conveys with property. Home being sold as-is, where-is, sale pending court approval,

  Emily Hacker-Todd CENTURY 21 Advantage Realty

  9 Linden Ave, Winchester, KY 40391
• 

  

  /79

  $849,900 Sold May 23, 2025

  3714 Wades Mill Rd, Winchester, KY 40391

  • 5 Beds
  • 3.5 Baths
  • 3,818 Sq Ft
  • Built 2001

  Last Sold Summary

  • $223/SF
  • 55 Days On Market

  Current Estimated Value $898,831

  Last Listing Agent Nora Williams Keller Williams Commonwealth

  3714 Wades Mill Rd, Winchester, KY 40391
• 

  

  /38

  Est $204,098 Not Listed For Sale

  412 Jameson Way, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,073 Sq Ft
  • Built 1990

  412 Jameson Way, Winchester, KY 40391

  Last Sold Summary

  • 25% Above List Price
  • $153/SF
  • 0 Days On Market

  • Last Sold Price $163,900
  • Aug 23, 2024

  Last Listing Agent Josh Wood Freedom Realty & Property Management
• 

  

  /5

  $439,000

  5127 Combs Ferry Rd, Ford, KY 40391

  14+ Acres of Prime land in the Heart of the Bluegrass! Whether you're dreaming of designing your ideal homestead or simply building your custom country home, this property offers the perfect blend of space, beauty, tranquility, and convenience. Enjoy peaceful rural living with open skies and scenic countryside views, surrounded by picturesque farms and a nearby vineyard that add to the charm of

  John Martin Exit Realty Crutcher Frankfort

  5127 Combs Ferry Rd, Ford, KY 40391
• 

  

  /51

  $560,000 Sold Jun 10, 2025

  520 Gay Evans Rd, Winchester, KY 40391

  • 3 Beds
  • 4 Baths
  • 3,160 Sq Ft
  • Built 2012

  Last Sold Summary

  • 3% Below List Price
  • $177/SF
  • 11 Days On Market

  Current Estimated Value $568,335

  Last Listing Agent Robin Jones Keller Williams Legacy Group

  520 Gay Evans Rd, Winchester, KY 40391
• 

  

  /14

  Est $196,220 Not Listed For Sale

  411 Jameson Way, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Built 1990

  411 Jameson Way, Winchester, KY 40391

  Last Sold Summary

  • 27% Above List Price
  • $155/SF
  • 19 Days On Market

  • Last Sold Price $155,000
  • Feb 06, 2025

  Last Listing Agent Jason Szaks EXIT TOWN & COUNTRY REALTORS
• 

  /2

  $188,500

  • Land
  • 12.1 Acres
  • $15,579 per Acre

  155 Spring Ridge Way, Winchester, KY 40391

  Great opportunity to develop/ build on 12+ acres. The property has three street stubs adjoining it. Three different concepts are included under documents. They are- R-1E, 4000 sq. Ft lots for 80 lots R-4- 14 Duplexes and 6 4plexes for 52 units R-1D - 6000 sq. Ft. Lots for 41 lots. Utilities are to the property and sewer availability should not be an issue. Please feel free to call the listing

  Jo Gawthrop Keller Williams Bluegrass Realty

  155 Spring Ridge Way, Winchester, KY 40391
• 

  

  /17

  $30,000 Sold Jun 30, 2025

  12591 Ironworks Rd, Winchester, KY 40391

  • Land
  • 1.72 Acres
  • $17,442 per Acre

  Last Sold Summary

  • 14% Below List Price
  • 51 Days On Market

  Current Estimated Value $125,073

  Last Listing Agent Cathleen Gedeon CENTURY 21 Advantage Realty

  12591 Ironworks Rd, Winchester, KY 40391
• 

  

  /33

  Est $290,818 Not Listed For Sale

  137 Summerhill Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,284 Sq Ft
  • Built 2003

  137 Summerhill Way, Winchester, KY 40391

  Last Sold Summary

  • 8% Above List Price
  • $210/SF
  • 6 Days On Market

  • Last Sold Price $270,000
  • Mar 07, 2025

  Last Listing Agent Keith Wilson Coldwell Banker McMahan
• 

  

  /10

  $591,650 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,200 Sq Ft

  104 Bella Shae Way, Winchester, KY 40391

  Welcome Home to the Winchester Floor Plan by CP Builders. This elegant ranch home features all-brick construction, a welcoming front porch, and a two-car garage. Step inside and be greeted by soaring 9-foot ceilings and a spacious open floor plan. The split bedroom design offers privacy and comfort, with a luxurious primary suite boasting an ensuite bathroom and a walk-in closet. Enjoy easy

  Shane Underwood Keller Williams Commonwealth

  104 Bella Shae Way, Winchester, KY 40391
• 

  

  /46

  $282,900 Sold Jan 02, 2026

  165 Hilltop Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,454 Sq Ft
  • Built 2020

  Last Sold Summary

  • 1% Below List Price
  • $195/SF
  • 6 Days On Market

  Current Estimated Value $277,277

  Last Listing Agent Tyson Walters Kassie & Associates

  165 Hilltop Dr, Winchester, KY 40391
• 

  

  /31

  Est $229,606 Not Listed For Sale

  121 Summerhill Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,302 Sq Ft
  • Built 2002

  121 Summerhill Way, Winchester, KY 40391

  Last Sold Summary

  • 18% Above List Price
  • $150/SF
  • 70 Days On Market

  • Last Sold Price $195,000
  • May 23, 2024

  Last Listing Agent Peter doCouto Plum Tree Realty
• 

  

  /64

  $259,900 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,161 Sq Ft

  17 Holiday Rd, Winchester, KY 40391

  This classic brick ranch house is move-in ready and waiting for you to call it home! Take a step inside the front door to appreciate the gleaming laminate wood floors in the open concept living space. Around the corner, the beautiful kitchen cabinets and updated, stainless, kitchen appliances are ready for family meals and social gatherings around the dining table. In the full bath, you'll find a

  Josh Wood Freedom Realty & Property Management

  17 Holiday Rd, Winchester, KY 40391
• 

  

  /41

  $650,000 Sold Jun 23, 2025

  357 Wades Mill Rd, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 3,007 Sq Ft
  • Built 2002

  Last Sold Summary

  • 6% Below List Price
  • $216/SF
  • 15 Days On Market

  Current Estimated Value $677,737

  Last Listing Agent Emily Belcher Rector Hayden Realtors

  357 Wades Mill Rd, Winchester, KY 40391
• 

  

  /23

  Est $270,815 Not Listed For Sale

  302 Salem Ave, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,490 Sq Ft
  • Built 2001

  302 Salem Ave, Winchester, KY 40391

  Last Sold Summary

  • 6% Above List Price
  • $171/SF
  • 34 Days On Market

  • Last Sold Price $255,000
  • Oct 01, 2024

  Last Listing Agent Emily Donaldson Keller Williams Commonwealth
• 

  /2

  $1,800,000

  • Land
  • 4.36 Acres
  • $412,844 per Acre

  722 Colby Rd Unit 1, Winchester, KY 40391

  Discover an exceptional opportunity for retail investment in the thriving Winchester area. Zoned B-4, this versatile property offers a wide array of possibilities for retail development, providing a strategic location for businesses seeking to establish a prominent presence. With its prime zoning and desirable position within the Winchester area, this property presents a compelling prospect for

  Cheryl Johnston CMI Properties

  722 Colby Rd Unit 1, Winchester, KY 40391
• 

  

  /23

  $210,000 Sold May 12, 2025

  202 Washington Square, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1998

  Last Sold Summary

  • 11% Above List Price
  • $175/SF
  • 1 Day On Market

  Current Estimated Value $213,246

  Last Listing Agent Aaron Kendall Lifstyl Real Estate

  202 Washington Square, Winchester, KY 40391
• 

  

  /17

  Est $292,111 Not Listed For Sale

  218 Bracken Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,292 Sq Ft
  • Built 2005

  218 Bracken Ct, Winchester, KY 40391

  Last Sold Summary

  • 5% Above List Price
  • $215/SF
  • 7 Days On Market

  • Last Sold Price $278,000
  • Apr 15, 2025

  Last Listing Agent Vickie Skeens RE/MAX
• 

  

  /43

  $259,000

  • 3 Beds
  • 2 Baths
  • 1,960 Sq Ft

  564 Trapp-Goffs Corner Rd, Winchester, KY 40391

  Private unrestricted 12-Acre Property in Winchester, KY - Convenient to Lexington & Red River Gorge This 3-bedroom, 2-bath single-family home with an office/flex room is situated on 12 acres in Winchester, KY, offering a combination of open and primarily wooded land. The property is located less than 40 minutes from Lexington and approximately 30 minutes from Red River Gorge. The home offers

  Felicia Mayes The Real Estate Co.

  564 Trapp-Goffs Corner Rd, Winchester, KY 40391
• 

  

  /26

  $250,000 Sold Feb 20, 2026

  21 Virginia Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,749 Sq Ft
  • Built 1962

  Last Sold Summary

  • 4% Below List Price
  • $143/SF
  • 40 Days On Market

  Current Estimated Value $251,872

  Last Listing Agent Emily Crump EXP Realty, LLC

  21 Virginia Ave, Winchester, KY 40391
• 

  

  /20

  Est $254,727 Not Listed For Sale

  208 Bracken Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,351 Sq Ft
  • Built 2002

  208 Bracken Ct, Winchester, KY 40391

  Last Sold Summary

  • 16% Above List Price
  • $163/SF
  • 0 Days On Market

  • Last Sold Price $220,000
  • Jul 05, 2023

  Last Listing Agent Nicholas Ratliff The LEXpert
• 

  

  /103

  $3,500,000

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

  5045 Van Meter Rd, Winchester, KY 40391

  Welcome to a truly exceptional 78-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
• 

  

  /44

  $206,500 Sold May 21, 2025

  206 W Clark Dr, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,107 Sq Ft
  • Built 1962

  Last Sold Summary

  • 6% Below List Price
  • $187/SF
  • 23 Days On Market

  Current Estimated Value $211,956

  Last Listing Agent Peggy Baldridge HomeFirst Real Estate

  206 W Clark Dr, Winchester, KY 40391
• 

  

  /32

  Est $243,336 Not Listed For Sale

  200 Bracken Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,252 Sq Ft
  • Built 2002

  200 Bracken Ct, Winchester, KY 40391

  Last Sold Summary

  • 6% Above List Price
  • $184/SF
  • 3 Days On Market

  • Last Sold Price $230,000
  • Mar 21, 2025

  Last Listing Agent Amy Diamond ERA Select Real Estate
• 

  /2

  $100,000

  • Land
  • 16,117 Sq Ft
  • $270,270 per Acre

  225 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

  225 Jacob Ct, Winchester, KY 40391
• 

  

  /19

  $199,900 Sold Feb 12, 2026

  117 Buffalo Trace, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,072 Sq Ft
  • Built 1998

  Last Sold Summary

  • $186/SF
  • 49 Days On Market

  Current Estimated Value $198,528

  Last Listing Agent Nena Honaker Tom Goebel & Company

  117 Buffalo Trace, Winchester, KY 40391
• 

  

  /37

  Est $296,051 Not Listed For Sale

  311 Fern Ct, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,326 Sq Ft
  • Built 1999

  311 Fern Ct, Winchester, KY 40391

  Last Sold Summary

  • 1% Below List Price
  • $128/SF
  • 8 Days On Market

  • Last Sold Price $298,000
  • Nov 01, 2024

  Last Listing Agent Robyn Bradley Woods Realty Group
• 

  

  /5

  $369,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,558 Sq Ft

  204 Jett Dr, Winchester, KY 40391

  New Construction, don't wait this one will not last, 3 bed/2 bath ranch, great floor plan, close to I-64 and I-75, lexington, richmond, call today! All colors, fixtures, granite, siding, outside landscaping, stone/brick, deck size, flooring have been ordered, New photos will be posted as house construction continues

  Mila Ensor Ensor Real Estate, LLC

  204 Jett Dr, Winchester, KY 40391
• 

  

  /44

  $310,000 Sold Jun 27, 2025

  2482 Mina Station Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,756 Sq Ft
  • Built 1962

  Last Sold Summary

  • $177/SF
  • 24 Days On Market

  Current Estimated Value $315,426

  Last Listing Agent Stephanie Hacker Kentucky Residential Real Estate, LLC

  2482 Mina Station Rd, Winchester, KY 40391
• 

  

  /49

  Est $295,879 Not Listed For Sale

  317 Fern Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,588 Sq Ft
  • Built 1999

  317 Fern Ct, Winchester, KY 40391

  Last Sold Summary

  • 7% Above List Price
  • $173/SF
  • 0 Days On Market

  • Last Sold Price $275,500
  • Apr 12, 2024

  Last Listing Agent Sherry Stephens Murphy Realty Group
• 

  /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
• 

  

  /12

  $75,000 Sold Jun 17, 2025

  120 Jacob Ct, Winchester, KY 40391

  • Land
  • 23,958 Sq Ft
  • $136,364 per Acre

  Last Sold Summary

  • 32% Below List Price
  • 210 Days On Market

  Current Estimated Value $165,627

  Last Listing Agent Keith Wilson Coldwell Banker McMahan

  120 Jacob Ct, Winchester, KY 40391
• 

  

  /75

  Est $284,220 Not Listed For Sale

  314 Fern Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,844 Sq Ft
  • Built 1999

  314 Fern Ct, Winchester, KY 40391

  Last Sold Summary

  • 3% Above List Price
  • $150/SF
  • 23 Days On Market

  • Last Sold Price $276,000
  • Sep 23, 2024

  Last Listing Agent Sherry Stephens Murphy Realty Group
• 

  

  /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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