Homes in ZIP Code 40391

• 

  

  /2

  $185,000

  Sold Nov 28, 2025

  23 Hillcrest Dr, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,557 Sq Ft
  • Built 1962

  Last Sold Summary

  • 12% Below List Price
  • $119/SF
  • 18 Days On Market

  Current Estimated Value $203,287

  Last Listing Agent Samantha Gray National Real Estate

  23 Hillcrest Dr, Winchester, KY 40391
• 

  

  

  /38

  Est $294,802

  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

  Last Listing Agent Dale Hatton Dream Maker Realty, LLC
• 

  

  

  /29

  $219,900

  • Land
  • 23.83 Acres
  • $9,228 per Acre

  3686 Crowe Ridge Rd, Winchester, KY 40391

  Discover the possibilities with this unique dual-property offering at 3686 & 3688 Crowe Ridge Road. Enjoy the peace and privacy of a beautiful country setting with room to spread out and endless potential. Whether you're looking for a primary residence with additional living space, an investment opportunity, or housing for extended family, this property offers versatility that's hard to find.

  Josh Wood Freedom Realty & Property Management

  3686 Crowe Ridge Rd, Winchester, KY 40391
• 

  

  

  /25

  $222,000

  Sold Jun 11, 2026

  213 Short St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,068 Sq Ft
  • Built 1955

  Last Sold Summary

  • 3% Below List Price
  • $208/SF
  • 2 Days On Market

  Current Estimated Value $224,015

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  213 Short St, Winchester, KY 40391
• 

  

  

  /33

  Est $179,253

  Not Listed For Sale

  307 Blair Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Built 1977

  307 Blair Ave, Winchester, KY 40391

  Last Sold Summary

  • 22 Days On Market

  Last Listing Agent Brooke Otis Mullins RO&CO Real Estate
• 

  

  /31

  $89,900

  • 2 Beds
  • 2 Baths
  • 828 Sq Ft

  308 Market St, Winchester, KY 40391

  Newly built and ready for its first owner, this 2-bedroom, 2-bathroom home in Quick Shop delivers the layout and finishes most buyers want without the price tag of new site-built construction. The main living area opens directly into the kitchen, giving the space a connected, airy feel that suits quiet evenings and gatherings alike. Down the hall, 2 bedrooms are sized for real furniture and real

  Hailey Blaylock Quick Shop MHC

  308 Market St, Winchester, KY 40391
• 

  

  /22

  $216,000

  Sold Feb 27, 2026

  521 Acadia Way, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,370 Sq Ft
  • Built 2001

  Last Sold Summary

  • 2% Below List Price
  • $158/SF
  • 17 Days On Market

  Current Estimated Value $220,615

  Last Listing Agent Tyler I Back The Brokerage

  521 Acadia Way, Winchester, KY 40391
• 

  

  /19

  Est $195,001

  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

  Last Listing Agent Jordan James Lifstyl Real Estate
• 

  

  /45

  $484,900

  New Construction

  • 4 Beds
  • 3 Baths
  • 2,381 Sq Ft

  410 Fairholme Way, Winchester, KY 40391

  Modern luxury meets everyday living in this beautiful new construction ranch home in Winchester's Fairholme Estates- where thoughtful details, timeless finishes, and incredible golf course view sunsets come together effortlessly. Inside, an inviting open-concept layout features vaulted ceilings and a fireplace anchoring the spacious living room. The timeless kitchen is designed to be both

  Morgan Withrow The Brokerage

  410 Fairholme Way, Winchester, KY 40391
• 

  

  /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 $530,615

  Last Listing Agent Maggie Napier Napier Realtors

  125 Casa Landa Way, Winchester, KY 40391
• 

  

  /29

  Est $184,930

  Not Listed For Sale

  217 Blair Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,025 Sq Ft
  • Built 1970

  217 Blair Ave, Winchester, KY 40391

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Ashley Barreto Indigo & Co
• 

  

  /65

  $359,900

  • 3 Beds
  • 2 Baths
  • 2,269 Sq Ft

  15 Moundale Ave, Winchester, KY 40391

  Welcome to this beautifully maintained all-brick home nestled in one of Winchester's most established and desirable neighborhoods. Offering over 2,200 square feet of finished living space, this 3-bedroom, 2-bath home combines timeless character with an impressive list of thoughtful updates. The main level features a spacious family room with ventless gas logs, a beautifully updated kitchen with

  Josh Wood Freedom Realty & Property Management

  15 Moundale Ave, 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 $271,929

  Last Listing Agent Joshua Davis The Agency

  916 Stratton Ln, Winchester, KY 40391
• 

  

  /26

  Est $187,016

  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

  Last Listing Agent Jim Woodrum RE/MAX Creative, Winchester
• 

  

  /63

  $785,000

  • 5 Beds
  • 2.5 Baths
  • 4,676 Sq Ft

  217 Wades Mill Rd, Winchester, KY 40391

  Escape to the peace and privacy of country living with this spacious brick one-and-a-half story home situated on just over 5 acres. With plenty of room to spread out, the main level offers a welcoming foyer, formal dining room, living room with a wood-burning fireplace, kitchen featuring granite countertops, tile backsplash, breakfast nook, and laundry room, along with the primary suite, three

  Michelle Blackburn RE/MAX Creative, Winchester

  217 Wades Mill Rd, 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 $406,682

  Last Listing Agent Julie Wiggington RE/MAX Creative, Winchester

  1731 Ford Hampton Rd, Winchester, KY 40391
• 

  

  /22

  Est $186,453

  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

  Last Listing Agent James Jeffries Brickhouse Real Estate
• 

  

  /62

  $309,900

  $20K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,904 Sq Ft

  335 Newcastle Ln, Winchester, KY 40391

  Welcome to this well-maintained home located in a quiet, established neighborhood with convenient access to everything Winchester has to offer. The first floor features an open and inviting layout, creating a comfortable space for everyday living and entertaining alike. Upstairs, you'll find a traditional three-bedroom floor plan with generously sized bedrooms, including a spacious primary suite.

  Josh Wood Freedom Realty & Property Management

  335 Newcastle Ln, 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 $604,120

  Last Listing Agent Janna Chalfant Smith United Real Estate Bluegrass

  180 Casa Landa Way, Winchester, KY 40391
• 

  

  /28

  Est $233,037

  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

  Last Listing Agent Janet Jones RE/MAX Elite Lexington
• 

  /2

  $100,000

  $10K PRICE DROP

  • Land
  • 13,939 Sq Ft
  • $312,500 per Acre

  115 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

  115 Duclair Dr, Winchester, KY 40391
• 

  

  /31

  $249,900

  Sold Jul 17, 2026

  123 Sunset Heights, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,446 Sq Ft
  • Built 1956

  Last Sold Summary

  • 2% Below List Price
  • $173/SF
  • 52 Days On Market

  Current Estimated Value $235,012

  Last Listing Agent Keith Wilson Coldwell Banker McMahan

  123 Sunset Heights, Winchester, KY 40391
• 

  

  /21

  Est $216,259

  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

  Last Listing Agent Holly Goeing The Agency
• 

  

  /45

  $360,000

  $55K PRICE DROP Pending

  • 3 Beds
  • 2.5 Baths
  • 1,803 Sq Ft

  608 Colby Rd, Winchester, KY 40391

  E Anthony Phillips RE/MAX Creative Realty

  608 Colby Rd, 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 $189,543

  Last Listing Agent Nicole Seals Guide Realty, Inc.

  40 Garner St, Winchester, KY 40391
• 

  

  /17

  Est $116,673

  Not Listed For Sale

  977 Muddy Creek Rd, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,030 Sq Ft
  • Built 1940

  977 Muddy Creek Rd, Winchester, KY 40391

  Last Sold Summary

  • 37 Days On Market

  Last Listing Agent Jason Szaks EXIT Town & Country Realtors
• 

  

  /30

  $274,500

  $15K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,420 Sq Ft

  137 Eastridge Dr, Winchester, KY 40391

  Welcome to this delightful 1.5-story home perfectly situated on a spacious corner lot just off the Eastern Bypass and only minutes from I-64. Convenience meets comfort in this beautifully maintained property offering 3 bedrooms, 2 full baths, and an inviting layout designed for everyday living. Step inside to an open living area ideal for entertaining, a spacious kitchen and dining space, and

  Kathy Burton Coldwell Banker McMahan

  137 Eastridge Dr, 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 $430,850

  Last Listing Agent Whitney Ensor Ensor Real Estate, LLC

  3886 Jackson Ferry Rd, Winchester, KY 40391
• 

  

  /79

  Est $207,142

  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

  Last Listing Agent Greg Wood Freedom Realty & Property Management
• 

  /2

  $110,000

  • Land
  • 14,810 Sq Ft
  • $323,529 per Acre

  230 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

  230 Duclair Dr, 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 $199,755

  Last Listing Agent Kim Dice eXp Realty, LLC

  111 Quail Ridge Rd, Winchester, KY 40391
• 

  

  /23

  Est $182,283

  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

  Last Listing Agent Darrell Lewis DIY Flat Fee.com
• 

  

  /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
• 

  

  /30

  $274,000

  Sold Sep 18, 2026

  158 Cabin Creek Heights, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,721 Sq Ft
  • Built 2005

  Last Sold Summary

  • 3% Below List Price
  • $159/SF
  • 1 Day On Market

  Current Estimated Value $301,211

  Last Listing Agent Kenzi Smith Lifstyl Real Estate

  158 Cabin Creek Heights, Winchester, KY 40391
• 

  

  /18

  Est $124,270

  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

  Last Listing Agent Austin Polley The Polley Group
• 

  

  /12

  $495,000

  $34K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,054 Sq Ft

  443 Oxford Dr Unit 443,445,447,449, Winchester, KY 40391

  Don't miss this rare quadruplex opportunity in Winchester. Featuring four units (443, 445,447 and 449 Oxford Drive), this property is perfect for investors seeking multiple income streams in one location. Each unit offers a similar layout with approximately 1,054 ft, 2 bedrooms, and 1.5 baths. The photos shown are from one updated unit, and all units have comparable layouts—making this an ideal

  Tracey Goebel Tom Goebel & Company

  443 Oxford Dr Unit 443,445,447,449, 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 $252,423

  Last Listing Agent Lura Justice Rector Hayden Realtors

  426 Paisley Ct, Winchester, KY 40391
• 

  

  /15

  Est $205,179

  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

  Last Listing Agent Jessica Moreno SimpliHOM
• 

  /2

  $269,000

  Pending

  • 3 Beds
  • 2 Baths
  • 2,592 Sq Ft

  728 Wayland Dr, Winchester, KY 40391

  E Anthony Phillips RE/MAX Creative Realty

  728 Wayland Dr, Winchester, KY 40391
• 

  

  /39

  $315,000

  Sold Aug 07, 2026

  13 Lakeview Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,932 Sq Ft
  • Built 1980

  Last Sold Summary

  • $163/SF
  • 5 Days On Market

  Current Estimated Value $313,030

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

  13 Lakeview Dr, Winchester, KY 40391

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