Homes in ZIP Code 40391

• 

  

  /2

  $42,500

  • 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
• 

  

  /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 $5,188,643

  Last Listing Agent Garry Milton Milton and Associates Real Estate

  175 Chatham Place, Winchester, KY 40391
• 

  

  

  /57

  Est $200,236

  Not Listed For Sale

  17 Hiawatha Trail, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,000 Sq Ft
  • Built 1968

  17 Hiawatha Trail, Winchester, KY 40391

  Last Sold Summary

  • 32 Days On Market

  Last Listing Agent Josh Wood Freedom Realty & Property Management
• 

  

  /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
• 

  

  

  /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 $361,927

  Last Listing Agent Elizabeth Hodge Lifstyl Real Estate

  356 Boone Ave, Winchester, KY 40391
• 

  

  /24

  Est $261,413

  Not Listed For Sale

  108 Dixon Way, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,377 Sq Ft
  • Built 2006

  108 Dixon Way, Winchester, KY 40391

  Last Sold Summary

  • 124 Days On Market

  Last Listing Agent Angie Conley Dixon Dixon Properties
• 

  

  /14

  $950,000

  • Land
  • 120 Acres
  • $7,917 per Acre

  345 Providence Ln, Winchester, KY 40391

  Rare opportunity to acquire approximately 120 acres of magnificent, rolling Bluegrass farmland in prime Clark County! This exceptionally versatile property features a ideal blend of cleared pasture and rich wooded land, making it perfectly suited for cattle, horses, recreational pursuits, or building your private dream estate.Equipped with a large pond, barn, and county water available at the

  Megan McCoy Keller Williams Legacy Group

  345 Providence Ln, Winchester, KY 40391
• 

  

  /15

  $280,000

  Sold Jul 17, 2026

  327 Newcastle Ln, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 1,693 Sq Ft
  • Built 2005

  Last Sold Summary

  • 6% Below List Price
  • $165/SF
  • 87 Days On Market

  Current Estimated Value $286,703

  Last Listing Agent Huong Dunn Bluegrass Property Exchange

  327 Newcastle Ln, Winchester, KY 40391
• 

  

  /19

  Est $200,933

  Not Listed For Sale

  170 Center Dr, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,517 Sq Ft
  • Built 1961

  170 Center Dr, Winchester, KY 40391

  Last Sold Summary

  • 52 Days On Market

  Last Listing Agent Larry Moore CENTURY 21 Simpson & Associates
• 

  

  /27

  $195,000

  Pending

  • 2 Beds
  • 1.5 Baths
  • 1,188 Sq Ft

  325 Essex Ct, Winchester, KY 40391

  FRESHLY PAINTED BRAND NEW APPLIANCES HUGE FENCED BACKYARD NEWER PRIVACY FENCE FIRST TIME BUYER OPPORTUNITY INVESTMENT OPPORTUNITY $1,000 BUYER CREDIT Welcome to 325 Essex Ct in Winchester! This charming 2 bedroom, 1.5 bath home offers an excellent opportunity for a first time homebuyer or investor looking for an affordable property with great potential. Inside, you'll find fresh paint and brand

  Amanda Hollon Keller Williams Commonwealth

  325 Essex Ct, 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 $140,118

  Last Listing Agent Lukas Owens The Brokerage

  46 Judy Ann Ct, Winchester, KY 40391
• 

  

  /48

  Est $227,095

  Not Listed For Sale

  217 Locust Grove Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,055 Sq Ft
  • Built 1955

  217 Locust Grove Rd, Winchester, KY 40391

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Robin Murray The Agency
• 

  

  /6

  $219,000

  $30K PRICE DROP Pending

  • Land
  • 8.03 Acres
  • $27,263 per Acre

  5127 Combs Ferry Rd, Ford, KY 40391

  8+ Acres of Prime land available in the Heart of the Bluegrass! Whether you're looking to design your ideal homestead or simply building your custom country home with plenty of space to roam, this property offers an optimal 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

  John Martin EXIT Realty Crutcher Frankfort

  5127 Combs Ferry Rd, Ford, KY 40391
• 

  

  /33

  $340,000

  Sold Jul 10, 2026

  740 Pilot Ridge Ln, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,608 Sq Ft
  • Built 2017

  Last Sold Summary

  • $211/SF
  • 6 Days On Market

  Current Estimated Value $339,909

  Last Listing Agent Holly Goeing The Agency

  740 Pilot Ridge Ln, Winchester, KY 40391
• 

  

  /58

  Est $204,990

  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

  • 27 Days On Market

  Last Listing Agent Josh Wood Freedom Realty & Property Management
• 

  /2

  $188,500

  Pending

  • 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.

  Jo Gawthrop Keller Williams Bluegrass Realty

  155 Spring Ridge Way, Winchester, KY 40391
• 

  

  /31

  $249,900

  Sold Jul 28, 2026

  312 Buffalo Trace, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,284 Sq Ft
  • Built 2001

  Last Sold Summary

  • $195/SF
  • 10 Days On Market

  Current Estimated Value $249,248

  Last Listing Agent Paula Cole The Agency

  312 Buffalo Trace, Winchester, KY 40391
• 

  

  /29

  Est $202,202

  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 Days On Market

  Last Listing Agent Kathryn Cheuvront Coldwell Banker McMahan
• 

  

  /10

  $591,650

  New Construction 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
• 

  

  /38

  $375,750

  Sold Apr 01, 2026

  6239 Old Boonesboro Rd, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,659 Sq Ft
  • Built 1960

  Last Sold Summary

  • 6% Below List Price
  • $141/SF
  • 121 Days On Market

  Current Estimated Value $403,307

  Last Listing Agent Kenya Woods United Real Estate Bluegrass

  6239 Old Boonesboro Rd, Winchester, KY 40391
• 

  

  /12

  Est $210,429

  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

  • 27 Days On Market

  Last Listing Agent Garry Milton Milton and Associates Real Estate
• 

  /2

  $1,800,000

  $2M PRICE INCREASE

  • 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
• 

  

  /88

  $710,000

  Sold Sep 03, 2026

  6500 Mount Sterling Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,148 Sq Ft
  • Built 1987

  Last Sold Summary

  • 10% Below List Price
  • $331/SF
  • 30 Days On Market

  Current Estimated Value $555,243

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  6500 Mount Sterling Rd, Winchester, KY 40391
• 

  

  /7

  Est $189,522

  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

  • 41 Days On Market

  Last Listing Agent Garry Milton Milton and Associates Real Estate
• 

  /2

  $100,000

  $10K PRICE DROP

  • 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
• 

  

  /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 $186,062

  Last Listing Agent Nena Honaker Tom Goebel & Company

  356 Colby Ridge Blvd, Winchester, KY 40391
• 

  

  /30

  Est $173,965

  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

  • 2 Days On Market

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester
• 

  /2

  $195,000

  $2M PRICE DROP

  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
• 

  

  /43

  $253,000

  Sold Jun 22, 2026

  564 Trapp-Goffs Corner Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,960 Sq Ft
  • Built 2000

  Last Sold Summary

  • 6% Below List Price
  • $129/SF
  • 54 Days On Market

  Current Estimated Value $256,476

  Last Listing Agent Felicia Mayes The Real Estate Co.

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

  

  /31

  Est $230,051

  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

  • 9 Days On Market

  Last Listing Agent Shane Underwood Keller Williams Commonwealth
• 

  

  /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
• 

  /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 $88,455

  Last Listing Agent Shari Frasure Keller Williams Commonwealth

  2465 Flanagan Station Rd, Winchester, KY 40391
• 

  

  /22

  Est $185,160

  Not Listed For Sale

  423 E Broadway St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 2,363 Sq Ft
  • Built 1878

  423 E Broadway St, Winchester, KY 40391

  Last Sold Summary

  • 23 Days On Market

  Last Listing Agent Tanya McKee Bluegrass Auction, Appraisal & Realty, LLC
• 

  

  /50

  $419,900

  $10K PRICE DROP

  • 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
• 

  

  /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 $291,637

  Last Listing Agent Tyson Walters Kassie & Associates

  165 Hilltop Dr, Winchester, KY 40391
• 

  

  /20

  Est $155,909

  Not Listed For Sale

  100 Dallas Aly, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,194 Sq Ft
  • Built 1920

  100 Dallas Aly, Winchester, KY 40391

  Last Sold Summary

  • 13 Days On Market

  Last Listing Agent Emidio Figueroa Rector Hayden Realtors
• 

  

  /32

  $320,000

  New Construction $30K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,310 Sq Ft

  38 N Burns Ave, Winchester, KY 40391

  Welcome to this beautiful BRAND NEW HOME in downtown Winchester! The open-concept design flows into a gorgeous kitchen w/granite countertops, gas stove, stainless appliances, and lots of cabinets. A first-floor bedroom w/private bath offers convenience flexibility. Upstairs, you'll find three generously sized bedrooms, each w/large closets, plus motion-activated hallway lighting. A covered back

  Trina Penn RE/MAX Creative Realty

  38 N Burns Ave, Winchester, KY 40391
• 

  

  /25

  $262,500

  Sold May 22, 2026

  398 Pine Ridge Rd, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,170 Sq Ft
  • Built 1977

  Last Sold Summary

  • 15% Below List Price
  • $224/SF
  • 97 Days On Market

  Current Estimated Value $272,299

  Last Listing Agent Amie Hieneman ERA Select Real Estate

  398 Pine Ridge Rd, Winchester, KY 40391
• 

  

  /55

  Est $203,715

  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

  • 8 Days On Market

  Last Listing Agent Christa Joynt Keller Williams Commonwealth
• 

  

  /23

  $225,000

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

  522 Acadia Way, Winchester, KY 40391

  This move in ready ranch home offering 4 bedrooms and 2 full bathrooms is ready for a new owner. This home is in an income restricted community, 80% of LIHTC for Clark County. The property offers brand new cabinets, countertops, appliances, flooring, fresh painting and more. Contact listing agent to receive the income limits for buyers to qualify to purchase property. Set up your showing today!

  Tyler I Back The Brokerage

  522 Acadia Way, Winchester, KY 40391

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