Homes in ZIP Code 40391

• 

  

  

  /19

  $209,000

  • Land
  • 41.69 Acres
  • $5,014 per Acre

  2697 Pine Ridge Rd, Winchester, KY 40391

  Escape to your own private retreat with this stunning 41.6± acre wooded tract nestled in the scenic countryside of Winchester, Kentucky. This expansive property offers a rare opportunity to own a secluded slice of nature, perfect for a private estate, recreational getaway, or hunting retreat. With rich with mature timber, this land presents a lot of natural beauty. A network of cleared trails and

  Derek Blankenship Keller Williams Commonwealth

  2697 Pine Ridge Rd, Winchester, KY 40391
• 

  

  

  /33

  $332,000 Sold Oct 14, 2025

  1831 Kiddville Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,756 Sq Ft
  • Built 1963

  Last Sold Summary

  • 5% Below List Price
  • $189/SF
  • 82 Days On Market

  Current Estimated Value $329,089

  Last Listing Agent Joshua Davis The Agency

  1831 Kiddville Rd, Winchester, KY 40391
• 

  

  

  /17

  Est $477,667 Not Listed For Sale

  1026 Crowe Ridge Rd, Winchester, KY 40391

  • 1 Bath
  • Built 1945

  1026 Crowe Ridge Rd, Winchester, KY 40391

  Last Sold Summary

  • 10% Above List Price
  • $407/SF
  • 56 Days On Market

  • Last Sold Price $435,000
  • Jan 09, 2025

  Last Listing Agent Sophia Herald Herald Real Estate
• 

  

  

  /19

  $499,000

  • Land
  • 36.94 Acres
  • $13,508 per Acre

  1455B Ky-89 Lot Unit Wp001, Winchester, KY 40391

  Don't miss this rare chance to own 36.45 premium acres on the outskirts of Winchesteran unbeatable blend of open farmland, development potential, and a truly top-tier location. Just minutes from I-64 and a quick drive to Lexington, this tract offers the convenience buyers want with the space and freedom they rarely find. The gorgeous rolling fields make this property ideal for farming, hay

  Greg Meade Whitetail Properties Real Estate

  1455B Ky-89 Lot Unit Wp001, Winchester, KY 40391
• 

  

  

  /25

  $223,000 Sold Nov 04, 2025

  204 Crawford Ct, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,636 Sq Ft
  • Built 1960

  Last Sold Summary

  • 3% Below List Price
  • $136/SF
  • 1 Day On Market

  Current Estimated Value $227,436

  Last Listing Agent Tisha Monte Bluegrass Properties Group

  204 Crawford Ct, Winchester, KY 40391
• 

  

  /32

  Est $364,045 Not Listed For Sale

  9221 Wades Mill Rd, Mount Sterling, KY 40353

  • 5 Beds
  • 3 Baths
  • 3,120 Sq Ft
  • Built 1994

  9221 Wades Mill Rd, Mount Sterling, KY 40353

  Last Sold Summary

  • 5% Above List Price
  • $111/SF
  • 4 Days On Market

  • Last Sold Price $347,000
  • Sep 21, 2023

  Last Listing Agent Joshua Davis The Agency
• 

  

  /62

  $435,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 3,633 Sq Ft

  2 Stoney Brook Dr, Winchester, KY 40391

  Welcome to this spacious brick ranch with a finished walkout basement, perfectly positioned on a corner lot in the desirable Stoney Brook neighborhood. Sitting on nearly half an acre, this home brings the space and flexibility buyers are looking for with multiple living areas including a family room, living room, and formal dining room. The main level offers a primary en suite, an additional full

  Kelli Hunt Berkshire Hathaway HomeServices Foster Realtors

  2 Stoney Brook Dr, Winchester, KY 40391
• 

  

  /29

  $227,500 Sold Sep 11, 2025

  301 Cabin Creek Heights, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,220 Sq Ft
  • Built 1970

  Last Sold Summary

  • 1% Above List Price
  • $186/SF
  • 0 Days On Market

  Current Estimated Value $226,786

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  301 Cabin Creek Heights, Winchester, KY 40391
• 

  

  /26

  Est $348,322 Not Listed For Sale

  11705 Irvine Rd, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 2,668 Sq Ft
  • Built 1988

  11705 Irvine Rd, Winchester, KY 40391

  Last Sold Summary

  • 58% Above List Price
  • $82/SF
  • 81 Days On Market

  • Last Sold Price $220,000
  • Jan 09, 2024

  Last Listing Agent Matthew J. Reffett Re/Max Legacy Group - Paintsville
• 

  

  /57

  $499,900

  • 4 Beds
  • 3 Baths
  • 5,646 Sq Ft

  16 Manor Dr, Winchester, KY 40391

  One Time Homeowner! Beautiful fieldstone ranch on full finished basement. 4 Bedrooms, 3 full bathrooms. This home has a very large great room, perfect for entertaining! Home has a new roof and siding as of 2024, new windows as of 2025. Home has tons of storage and tons of character. Come see this wonderful house and make it your forever home!

  Zella Rosenthal Tom Goebel & Company

  16 Manor Dr, Winchester, KY 40391
• 

  /2

  $125,000 Sold May 23, 2025

  265 Duclair Dr, Winchester, KY 40391

  • Land
  • 1.01 Acres
  • $123,762 per Acre

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent John Wilson Bluegrass Properties Group

  265 Duclair Dr, Winchester, KY 40391
• 

  

  /33

  Est $222,789 Not Listed For Sale

  510 Wills Rupard Rd, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,592 Sq Ft
  • Built 1990

  510 Wills Rupard Rd, Winchester, KY 40391

  Last Sold Summary

  • 23% Above List Price
  • $114/SF
  • 2 Days On Market

  • Last Sold Price $181,000
  • May 25, 2023

  Last Listing Agent Joe Marcum CENTURY 21 Advantage Realty
• 

  

  /56

  $325,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,450 Sq Ft

  215 Old Log Lick Rd, Winchester, KY 40391

  Price drop plus Seller will credit Buyer $1,000 for carpet repair/replacement. Enjoy where you live! Zen like grounds will bring inner peace in this 1,450 sq foot home on over 3 private acres. Covered front and back porches span the width of the house. Get off the grid with the solar panels on the roof (25 yr warranty), six raised garden beds, and fenced chicken coop! Average utility bill $50 in

  Kerry Ball Local First Realty, LLC

  215 Old Log Lick Rd, Winchester, KY 40391
• 

  

  /41

  $279,900 Sold Aug 12, 2025

  225 Prescott Ln, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,808 Sq Ft
  • Built 2006

  Last Sold Summary

  • $155/SF
  • 8 Days On Market

  Current Estimated Value $285,664

  Last Listing Agent Teresa Richmond Freedom Realty & Property Management

  225 Prescott Ln, Winchester, KY 40391
• 

  

  /33

  Est $277,056 Not Listed For Sale

  7344 Ironworks Rd, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,400 Sq Ft
  • Built 1925

  7344 Ironworks Rd, Winchester, KY 40391

  Last Sold Summary

  • 27% Above List Price
  • $156/SF
  • 2 Days On Market

  • Last Sold Price $219,000
  • Mar 07, 2024

  Last Listing Agent Jason Rainey Executive Real Estate, LLC
• 

  

  /57

  $350,000

  • 4 Beds
  • 2 Baths
  • 3,261 Sq Ft

  443 S Maple St, Winchester, KY 40391

  Full of history and charm, this 1905 home sits on one of Winchester's most beloved and cherished streets, a place where homes like this are held onto for generations. It offers a rare opportunity to own a piece of the past while creating something truly your own. The inviting, oversized front porch sets the tone, perfect for quiet mornings, evening conversations, and the simple moments that make

  Terra Long Keller Williams Commonwealth

  443 S Maple St, Winchester, KY 40391
• 

  

  /24

  $185,000 Sold Jun 23, 2025

  605 Dixiana Dr, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,044 Sq Ft
  • Built 1990

  Last Sold Summary

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

  Current Estimated Value $191,968

  Last Listing Agent Dale Hatton Dream Maker Realty, LLC

  605 Dixiana Dr, Winchester, KY 40391
• 

  

  /82

  Est $391,136 Not Listed For Sale

  380 L E Junction Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 3,173 Sq Ft
  • Built 1976

  380 L E Junction Rd, Winchester, KY 40391

  Last Sold Summary

  • 21% Above List Price
  • $102/SF
  • 13 Days On Market

  • Last Sold Price $324,000
  • Jul 14, 2023

  Last Listing Agent Davin Smith Caswell Prewitt Realty, Inc
• 

  

  /38

  $329,900

  • 4 Beds
  • 1 Bath
  • 2,327 Sq Ft

  162 French Ave, Winchester, KY 40391

  Could 162 French Ave., Winchester, KY 40391 be your new address? This stunning, updated Craftsman home feels like it was pulled straight from the pages of Southern Living Magazine, blending modern updates with timeless character and charm. Recent improvements including new windows, doors, wiring, and fresh landscaping enhance the home while preserving its original appeal. This move-in ready

  Jonathan Wood HomeLand Real Estate Inc - Mt Sterling

  162 French Ave, Winchester, KY 40391
• 

  

  /39

  $340,000 Sold Oct 10, 2025

  219 Hampton Ave, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,929 Sq Ft
  • Built 1972

  Last Sold Summary

  • 7% Below List Price
  • $116/SF
  • 48 Days On Market

  Current Estimated Value $344,663

  Last Listing Agent Jo Gawthrop Keller Williams Bluegrass Realty

  219 Hampton Ave, Winchester, KY 40391
• 

  

  /51

  Est $461,945 Not Listed For Sale

  5600 Ecton Rd, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 2,841 Sq Ft
  • Built 1992

  5600 Ecton Rd, Winchester, KY 40391

  Last Sold Summary

  • $162/SF
  • 62 Days On Market

  • Last Sold Price $460,000
  • Dec 29, 2023

  Last Listing Agent Kymberly McCreary Keller Williams Commonwealth
• 

  

  /24

  $369,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,635 Sq Ft

  206 Jett Dr, Winchester, KY 40391

  New Construction, come view, great house plan, ranch on a crawl space, 3 bedrooms, 2 bath, you will love this inviting neighborhood, plan shown on line could vary, this is a spec home, all the colors have been decided, fixtures, flooring, brick, siding, cabinets, countertops have been ordered, restrictions apply, no HOA, buyer to verify sq ft of home and lot. This home is close to I-64, I-75,

  Mila Ensor Ensor Real Estate, LLC

  206 Jett Dr, Winchester, KY 40391
• 

  

  /58

  $850,000 Sold Jun 27, 2025

  2158 Venable Rd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,980 Sq Ft
  • Built 1988

  Last Sold Summary

  • $285/SF
  • 1 Day On Market

  Current Estimated Value $851,707

  Last Listing Agent Emily Miller Bluegrass Sotheby's International Realty

  2158 Venable Rd, Winchester, KY 40391
• 

  

  /38

  Est $373,764 Not Listed For Sale

  3070 Goshen Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,866 Sq Ft
  • Built 1998

  3070 Goshen Rd, Winchester, KY 40391

  Last Sold Summary

  • 2% Above List Price
  • $128/SF
  • 2 Days On Market

  • Last Sold Price $367,000
  • Apr 22, 2024

  Last Listing Agent Kevin Bradley Keller Williams Legacy Group
• 

  

  /10

  $550,000 New Construction

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

  107 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

  107 Bella Shae Way, Winchester, KY 40391
• 

  

  /28

  $83,000 Sold May 08, 2026

  32 Hays St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,540 Sq Ft
  • Built 1950

  Last Sold Summary

  • 8% Below List Price
  • $54/SF
  • 5 Days On Market

  Current Estimated Value $122,842

  Last Listing Agent Christa Joynt Keller Williams Commonwealth

  32 Hays St, Winchester, KY 40391
• 

  

  /88

  Est $635,668 Not Listed For Sale

  865 Sugar Ridge Rd, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 2,146 Sq Ft
  • Built 1997

  865 Sugar Ridge Rd, Winchester, KY 40391

  Last Sold Summary

  • 14% Below List Price
  • $345/SF
  • 88 Days On Market

  • Last Sold Price $740,000
  • Apr 25, 2025

  Last Listing Agent Alysia Niva Century 21 Advantage Realty - Georgetown
• 

  

  /55

  $569,900

  • 3 Beds
  • 2 Baths
  • 2,280 Sq Ft

  108 Bella Shae Way, Winchester, KY 40391

  Nearly new French country ranch that has been gently lived in. This classy home has magnificent curb appeal. When you walk through the front door you are welcomed by a tasteful foyer area. Stroll into the wide-open space of the great room with a towering, coffered ceiling and tons of natural light. The gas fireplace adds a nice focal point to the living space. The kitchen space is equipped with

  Vickie Skeens RE/MAX Elite Lexington

  108 Bella Shae Way, Winchester, KY 40391
• 

  

  /71

  $690,500 Sold Sep 09, 2025

  2950 Pretty Run Rd, Ford, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,912 Sq Ft
  • Built 2022

  Last Sold Summary

  • $237/SF
  • 3 Days On Market

  Current Estimated Value $686,527

  Last Listing Agent Angela Newby Calumet Realty

  2950 Pretty Run Rd, Ford, KY 40391
• 

  

  /76

  Est $794,322 Not Listed For Sale

  775 Sugar Ridge Rd, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,860 Sq Ft
  • Built 1996

  775 Sugar Ridge Rd, Winchester, KY 40391

  Last Sold Summary

  • 15% Above List Price
  • $241/SF
  • 2 Days On Market

  • Last Sold Price $690,000
  • Feb 24, 2025

  Last Listing Agent Cassie Foley CENTURY 21 Advantage Realty
• 

  

  /29

  $344,900

  • 3 Beds
  • 2 Baths
  • 1,858 Sq Ft

  23 Windridge Dr, Winchester, KY 40391

  Welcome home!!! This beautifully updated all-brick ranch that perfectly blends charm and modern upgrades in a well established, desirable neighborhood is sure to please. Step inside to a bright open-concept living space featuring luxury vinyl flooring, a stunning wood-burning fireplace, and exposed wood ceiling beams that create a warm, inviting atmosphere in the spacious family room. The

  Holly Goeing The Agency

  23 Windridge Dr, Winchester, KY 40391
• 

  

  /69

  $282,500 Sold Sep 30, 2025

  227 Cross Brook Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,508 Sq Ft
  • Built 2001

  Last Sold Summary

  • 1% Below List Price
  • $187/SF
  • 9 Days On Market

  Current Estimated Value $280,903

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  227 Cross Brook Ln, Winchester, KY 40391
• 

  

  /32

  Est $305,463 Not Listed For Sale

  810 Howard Creek Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,260 Sq Ft
  • Built 2001

  810 Howard Creek Rd, Winchester, KY 40391

  Last Sold Summary

  • 15% Above List Price
  • $210/SF
  • 17 Days On Market

  • Last Sold Price $264,900
  • Jun 09, 2023

  Last Listing Agent Serena Cassidy Coldwell Banker McMahan
• 

  

  /57

  $350,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,640 Sq Ft

  220 Hibiscus Ln, Winchester, KY 40391

  Welcome home to this immaculate gem nestled in the charming Hibiscus Terrace Subdivision! This beautifully maintained three-bedroom, two-bathroom home offers 1,640 square feet of thoughtfully designed living space that blends comfort with everyday functionality. Inside, discover a warm, inviting interior where fresh carpet installed in 2022 greets you with plush softness throughout. The

  Timothy Saylor Threshold Real Estate Services

  220 Hibiscus Ln, Winchester, KY 40391
• 

  

  /75

  $289,900 Sold Aug 11, 2025

  126 Ashley Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,429 Sq Ft
  • Built 1992

  Last Sold Summary

  • $203/SF
  • 0 Days On Market

  Current Estimated Value $288,570

  Last Listing Agent Jennifer Guyton White Realty, LLC

  126 Ashley Dr, Winchester, KY 40391
• 

  

  /53

  Est $291,334 Not Listed For Sale

  1489 White Conkwright Rd, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,126 Sq Ft
  • Built 1995

  1489 White Conkwright Rd, Winchester, KY 40391

  Last Sold Summary

  • 6% Above List Price
  • $244/SF
  • 45 Days On Market

  • Last Sold Price $275,000
  • Mar 11, 2024

  Last Listing Agent Sabina Chambers Semonin Realty
• 

  

  /31

  $299,900 Pending

  • 4 Beds
  • 2 Baths
  • 1,840 Sq Ft

  306 Trapp-Goffs Corner Rd, Winchester, KY 40391

  Beautiful Four Bedroom 2 Bathroom Ranch Home On A Finished Basement With Over 2 Acres!! Bring Your Family, Toys, Animals And Enjoy Country Living Close To Mountain Parkway And Close To Two Country Restaurants! Sellers Have Finished Basement To Add An Additional Bedroom, Bathroom And Lots Of Storage!! And Dont Miss The Large Deck With a View!

  Patrick Arvin Keller Williams Commonwealth

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

  

  /58

  $345,000 Sold Nov 14, 2025

  205 Chardonnay Ct, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,179 Sq Ft
  • Built 1991

  Last Sold Summary

  • 8% Below List Price
  • $158/SF
  • 59 Days On Market

  Current Estimated Value $357,768

  Last Listing Agent Janna Chalfant Smith United Real Estate Bluegrass

  205 Chardonnay Ct, Winchester, KY 40391
• 

  

  /23

  Est $305,385 Not Listed For Sale

  440 White Conkwright Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,624 Sq Ft
  • Built 2004

  440 White Conkwright Rd, Winchester, KY 40391

  Last Sold Summary

  • 25% Above List Price
  • $151/SF
  • 3 Days On Market

  • Last Sold Price $245,000
  • Jun 21, 2023

  Last Listing Agent Louis Baldwin Threshold Real Estate Services
• 

  

  /15

  $294,900

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

  327 Newcastle Ln, Winchester, KY 40391

  Seller is offering $2000 total towards buyers concession (can be used for downpayment, prepaids and closing cost)!! Welcome home to this cozy cute FOUR bedroom house with 2 full bath/ 1 half bath! Rare to find- Primary bedroom and full bath on first floor. Large living area with plenty of sunlight through insulated windows and skylights. This open floorpan also showcases a nice open staircase

  Huong Dunn Bluegrass Property Exchange

  327 Newcastle Ln, Winchester, KY 40391

Showing Results 81 - 120, Page 3 of 18