Homes in ZIP Code 40391

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  /27

  $210,000 Sold Sep 04, 2025

  305 Geronimo Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,150 Sq Ft
  • Built 1999

  Last Sold Summary

  • 5% Below List Price
  • $183/SF
  • 1 Day On Market

  Current Estimated Value $216,633

  Last Listing Agent Aaron Kendall Lifstyl Real Estate

  305 Geronimo Ct, Winchester, KY 40391
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  /78

  Est $525,547 Not Listed For Sale

  7625 Irvine Rd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,689 Sq Ft
  • Built 2006

  7625 Irvine Rd, Winchester, KY 40391

  Last Sold Summary

  • 8% Below List Price
  • $212/SF
  • 42 Days On Market

  • Last Sold Price $570,000
  • Aug 14, 2023

  Last Listing Agent Elizabeth Torchia Caswell Prewitt Realty, Inc
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  /33

  $339,900 Pending

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

  740 Pilot Ridge Ln, Winchester, KY 40391

  Tucked away on 1.25 fully fenced acres, this custom-built home offers some of the most breathtaking views in Winchester. Designed with charm and comfort in mind, this 3-bedroom, 2.5-bath home blends modern convenience with timeless farmhouse style. Step inside to an open, inviting layout filled with natural light and warm finishes throughout. The spacious vaulted master suite is a true retreat,

  Holly Goeing The Agency

  740 Pilot Ridge Ln, Winchester, KY 40391
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  /44

  $320,000 Sold Nov 21, 2025

  104 Teakwood Ct, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 1,970 Sq Ft
  • Built 2005

  Last Sold Summary

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

  Current Estimated Value $322,889

  Last Listing Agent Jessica Noto Century 21 Advantage Realty - Georgetown

  104 Teakwood Ct, Winchester, KY 40391
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  /39

  Est $375,715 Not Listed For Sale

  3232 Old Ruckerville Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,424 Sq Ft
  • Built 1994

  3232 Old Ruckerville Rd, Winchester, KY 40391

  Last Sold Summary

  • 17% Above List Price
  • $225/SF
  • 2 Days On Market

  • Last Sold Price $320,000
  • Aug 23, 2023

  Last Listing Agent Megan McCoy Keller Williams Legacy Group
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  /52

  $339,900

  • 4 Beds
  • 2 Baths
  • 1,843 Sq Ft

  228 Holiday Rd, Winchester, KY 40391

  Back on the market at no fault of the sellers. Don't miss your chance to own this beautifully updated split-level home in Holiday Hills! Featuring 4 bedrooms and 2 full baths, this home offers a bright, open-concept kitchen and living area perfect for both everyday living and entertaining. Thoughtfully updated in recent years, the home features newer flooring, fresh paint, updated cabinets and

  Caroline Mucci CENTURY 21 Commonwealth R E

  228 Holiday Rd, Winchester, KY 40391
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  /27

  $274,900 Sold May 23, 2025

  707 Terry Dr, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,770 Sq Ft
  • Built 1978

  Last Sold Summary

  • 5% Below List Price
  • $155/SF
  • 40 Days On Market

  Current Estimated Value $290,759

  Last Listing Agent Kymberly McCreary EXP Realty, LLC

  707 Terry Dr, Winchester, KY 40391
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  /36

  Est $452,904 Not Listed For Sale

  5487 Irvine Rd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,892 Sq Ft
  • Built 1978

  5487 Irvine Rd, Winchester, KY 40391

  Last Sold Summary

  • 17% Above List Price
  • $134/SF
  • 47 Days On Market

  • Last Sold Price $388,000
  • Nov 06, 2023

  Last Listing Agent Wayne Elkins RE/MAX
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  /33

  $350,000 New Construction

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

  38 N Burns Ave, Winchester, KY 40391

  Welcome to this beautiful 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 porch

  Trina Penn RE/MAX Creative Realty

  38 N Burns Ave, Winchester, KY 40391
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  /39

  $549,000 Sold Jul 30, 2025

  154 Hawthorne Dr, Winchester, KY 40391

  • 5 Beds
  • 3.5 Baths
  • 3,478 Sq Ft
  • Built 2020

  Last Sold Summary

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

  Current Estimated Value $562,711

  Last Listing Agent Jarran Thomas The Agency

  154 Hawthorne Dr, Winchester, KY 40391
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  /34

  Est $368,891 Not Listed For Sale

  4759 Ironworks Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,633 Sq Ft
  • Built 1985

  4759 Ironworks Rd, Winchester, KY 40391

  Last Sold Summary

  • 6% Above List Price
  • $214/SF
  • 2 Days On Market

  • Last Sold Price $349,500
  • May 08, 2024

  Last Listing Agent Hannah Simpkins National Real Estate
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  /20

  $312,000 Open Sun 1PM - 3PM

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

  200 Dubuy Dr, Winchester, KY 40391

  Search no more your dream home just hit the market! You will fall in love with this one as soon as you walk through the front door. Beautiful open concept, very modern new home just built in 2022. You're going to love the open kitchen and living room area with the large kitchen island, beautiful stainless steel appliances and granite countertops. Primary bedroom on the first floor with a full

  Wayne Elkins RE/MAX Creative Realty

  200 Dubuy Dr, Winchester, KY 40391
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  /47

  $374,900 Sold Sep 19, 2025

  714 Concord Ave, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,750 Sq Ft
  • Built 2017

  Last Sold Summary

  • $214/SF
  • 23 Days On Market

  Current Estimated Value $377,293

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  714 Concord Ave, Winchester, KY 40391
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  /41

  Est $333,895 Not Listed For Sale

  2100 Miller Hunt Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,550 Sq Ft
  • Built 1988

  2100 Miller Hunt Rd, Winchester, KY 40391

  Last Sold Summary

  • 2% Below List Price
  • $219/SF
  • 44 Days On Market

  • Last Sold Price $340,000
  • Jan 05, 2024

  Last Listing Agent Patrick Doyle Lifstyl Real Estate
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  /31

  $339,900

  • 4 Beds
  • 2.5 Baths
  • 2,010 Sq Ft

  110 Powe Dr, Winchester, KY 40391

  This 4 Bedroom, 3 Bath home is quietly nestled within the Greenfield subdivision. Prime location just off the Winchester Bypass. This property has so much to offer. Updates can be seen throughout. Large first floor primary bedroom with on-suite and walk in closet, spacious family room, large yard with mature trees as well as widened driveway for additional parking, above ground pool with duel

  Michael Hilario The Agency

  110 Powe Dr, Winchester, KY 40391
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  /38

  $340,000 Sold Apr 30, 2026

  168 Buckingham Ln, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,358 Sq Ft
  • Built 2000

  Last Sold Summary

  • $144/SF
  • 3 Days On Market

  Current Estimated Value $340,848

  Last Listing Agent Tammy Hill Keller Williams Legacy Group

  168 Buckingham Ln, Winchester, KY 40391
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  /62

  Est $407,559 Not Listed For Sale

  890 Miller Hunt Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,425 Sq Ft
  • Built 1965

  890 Miller Hunt Rd, Winchester, KY 40391

  Last Sold Summary

  • 6% Above List Price
  • $269/SF
  • 5 Days On Market

  • Last Sold Price $384,000
  • Apr 10, 2025

  Last Listing Agent Daniel Mullins ERA Select Real Estate
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  /23

  $324,900

  • 3 Beds
  • 2.5 Baths
  • 3,868 Sq Ft

  225 Plantations Dr, Winchester, KY 40391

  Welcome to 225 Plantations Drive, a beautifully maintained home in the desirable Royal Oaks Subdivision. This charming three-bedroom, two-and-a-half-bath residence is in wonderful condition and move-in ready! This is home comes with a wonderful floorplan that has a primary bedroom with built-in's on the first floor, Kitchen with granite and stainless appliances and deck has been updated with Trex

  John Wilson Bluegrass Properties Group

  225 Plantations Dr, Winchester, KY 40391
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  /92

  $1,075,000 Sold Mar 18, 2026

  6237 Bybee Rd, Winchester, KY 40391

  • 5 Beds
  • 7 Baths
  • 8,236 Sq Ft
  • Built 2000

  Last Sold Summary

  • 10% Below List Price
  • $131/SF
  • 212 Days On Market

  Current Estimated Value $1,072,420

  Last Listing Agent Amanda Marcum Berkshire Hathaway HomeServices Foster Realtors

  6237 Bybee Rd, Winchester, KY 40391
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  /29

  Est $435,505 Not Listed For Sale

  1623 Little Stoner Rd, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,800 Sq Ft
  • Built 1982

  1623 Little Stoner Rd, Winchester, KY 40391

  Last Sold Summary

  • 13% Above List Price
  • $138/SF
  • 25 Days On Market

  • Last Sold Price $385,000
  • Apr 21, 2025

  Last Listing Agent Sharon Ben David Berkshire Hathaway de Movellan Properties
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  /34

  $349,000

  • 4 Beds
  • 2.5 Baths
  • 2,274 Sq Ft

  405 Tremont Ln, Winchester, KY 40391

  Welcome to this beautifully maintained 4 bedroom, 2.5 bathroom home over 2,200 square feet of comfortable living space. Built in 2005, this two story home features a functional layout with the primary suite and laundry conveniently located on the main level. Step into fresh paint, undated vinyl flooring and a spacious living area complete with a cozy fireplace perfect for entertaining or

  Darryl Bond Guide Realty, Inc.

  405 Tremont Ln, Winchester, KY 40391
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  /36

  $309,000 Sold May 21, 2025

  172 Buckingham Ln, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,958 Sq Ft
  • Built 1999

  Last Sold Summary

  • 6% Below List Price
  • $158/SF
  • 29 Days On Market

  Current Estimated Value $320,482

  Last Listing Agent Mila Ensor Ensor Real Estate, LLC

  172 Buckingham Ln, Winchester, KY 40391
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  /42

  Est $333,804 Not Listed For Sale

  1570 Little Stoner Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,488 Sq Ft
  • Built 1990

  1570 Little Stoner Rd, Winchester, KY 40391

  Last Sold Summary

  • 11% Above List Price
  • $202/SF
  • 1 Day On Market

  • Last Sold Price $300,000
  • Aug 23, 2024

  Last Listing Agent Joyce Ratliff Tom Goebel & Company
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  /49

  $345,000

  • 3 Beds
  • 2.5 Baths
  • 2,628 Sq Ft

  221 Moundale Ave, Winchester, KY 40391

  Step back in time as you walk up the stone steps into this beautiful 3 bed 2.5 bath house. This house has been very well maintained and offers many updates. You get the best of both worlds the craftsmanship of an older home with all the newer amenities. Hardwood, tile and brick floors throughout the house with Granite countertops, This house sits on a lot and a half. The owners have recently

  Andrew Fugitt Coldwell Banker McMahan

  221 Moundale Ave, Winchester, KY 40391
• 

  

  /42

  $390,000 Sold Oct 21, 2025

  19 Snowfall Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,625 Sq Ft
  • Built 1950

  Last Sold Summary

  • 11% Above List Price
  • $240/SF
  • 2 Days On Market

  Current Estimated Value $359,983

  Last Listing Agent Bradford Queen Bluegrass Sotheby's International Realty

  19 Snowfall Dr, Winchester, KY 40391
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  /47

  Est $384,429 Not Listed For Sale

  150 Privacy Ln, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 2,784 Sq Ft
  • Built 1987

  150 Privacy Ln, Winchester, KY 40391

  Last Sold Summary

  • 16% Above List Price
  • $119/SF
  • 103 Days On Market

  • Last Sold Price $330,000
  • Mar 31, 2025

  Last Listing Agent Jason Joseph Keller Williams Commonwealth
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  /55

  $359,900

  • 3 Beds
  • 2 Baths
  • 2,835 Sq Ft

  27 Hampton Ave, Winchester, KY 40391

  Located on desirable Hampton Avenue, this all-brick ranch is full of timeless character and thoughtful updates. Beautiful original hardwood floors run throughout the main level, highlighted by detailed craftsmanship and charm you don't find every day. The spacious living room features built-ins, a fireplace, and flows into the dining area, creating a warm and inviting space for everyday living or

  Terra Long Keller Williams Commonwealth

  27 Hampton Ave, Winchester, KY 40391
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  /34

  $369,500 Sold Aug 22, 2025

  148 Gibson Way, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,456 Sq Ft
  • Built 2022

  Last Sold Summary

  • 4% Below List Price
  • $150/SF
  • 11 Days On Market

  Current Estimated Value $364,901

  Last Listing Agent Patrick Arvin Keller Williams Commonwealth

  148 Gibson Way, Winchester, KY 40391
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  /41

  Est $357,542 Not Listed For Sale

  5751 Mount Sterling Rd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,988 Sq Ft
  • Built 1976

  5751 Mount Sterling Rd, Winchester, KY 40391

  Last Sold Summary

  • 45% Above List Price
  • $124/SF
  • 54 Days On Market

  • Last Sold Price $245,900
  • Aug 25, 2023

  Last Listing Agent Chandler Williams Keller Williams Legacy Group
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  /38

  $296,900

  • 4 Beds
  • 2 Baths
  • 2,116 Sq Ft

  618 Westmeade Dr, Winchester, KY 40391

  Conveniently located, this charming well kept home features a functional floorplan offering space that can be tailored for those who love to entertain or the growing family. On the main level you'll find the living room, an eat in kitchen, 3 bedrooms and a full bathroom. Off of the kitchen is a large deck that's perfect for get togethers with family or friends. Downstairs has a second living

  Kristi Donaldson United Real Estate Bluegrass

  618 Westmeade Dr, Winchester, KY 40391
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  /26

  $200,000 Sold Oct 02, 2025

  34 N Burns Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Built 1945

  Last Sold Summary

  • 11% Below List Price
  • $133/SF
  • 8 Days On Market

  Current Estimated Value $209,622

  Last Listing Agent Ashley Barreto Indigo & Co

  34 N Burns Ave, Winchester, KY 40391
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  /36

  Est $367,890 Not Listed For Sale

  610 Old Ruckerville Rd, Winchester, KY 40391

  • 2 Beds
  • 2.5 Baths
  • 1,800 Sq Ft
  • Built 1997

  610 Old Ruckerville Rd, Winchester, KY 40391

  Last Sold Summary

  • 8% Above List Price
  • $190/SF
  • 37 Days On Market

  • Last Sold Price $342,000
  • May 31, 2024

  Last Listing Agent Garnett Davis Tom Goebel & Company
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  /40

  $299,000

  • 3 Beds
  • 2 Baths
  • 1,692 Sq Ft

  54 Locust Dr, Winchester, KY 40391

  Opportunity awaits at 54 Locust Drive in Wesleyan Park subdivision. This all-brick ranch on a full unfinished basement offers 3 bedrooms, 2 baths, and 1,692 square feet of finished living space, along with an equally spacious basement ready for storage, hobbies, or future possibilities. Built in 1960, this home features hardwood flooring, a 2-car attached garage, and a fenced backyard with a

  Natalie Avant Berkshire Hathaway HomeServices Foster Realtors

  54 Locust Dr, Winchester, KY 40391
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  /16

  $214,900 Sold Dec 05, 2025

  15 Holly Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 2025

  Last Sold Summary

  • 4% Below List Price
  • $179/SF
  • 52 Days On Market

  Current Estimated Value $213,472

  Last Listing Agent Nena Honaker Tom Goebel & Company

  15 Holly Ave, Winchester, KY 40391
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  /35

  Est $273,111 Not Listed For Sale

  3230 Irvine Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,510 Sq Ft
  • Built 1978

  3230 Irvine Rd, Winchester, KY 40391

  Last Sold Summary

  • 16% Above List Price
  • $156/SF
  • 47 Days On Market

  • Last Sold Price $235,000
  • Dec 04, 2024

  Last Listing Agent Cindy Hellinger Diamond Real Estate Group, Inc
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  /38

  $359,900 Pending

  • 4 Beds
  • 4.5 Baths

  3600 Crowe Ridge Rd, Winchester, KY 40391

  Newly constructed unfinished multigenerational home located on 4 acres. Separate level living with 2 kitchens, 2 laundry rooms, and an en-suite for every bedroom. The main floor features 20' cathedral ceilings, 8' doors and 15 3'x6' windows creating a spacious home boasting panoramic views. Includes an additional 20'x24' loft space and 2 flex rooms with ANSI standard windows. Secondary living

  Maggie Napier Napier Realtors

  3600 Crowe Ridge Rd, Winchester, KY 40391
• 

  

  /54

  $410,000 Sold Apr 10, 2026

  204 Delaplain Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 3,563 Sq Ft
  • Built 1979

  Last Sold Summary

  • 6% Below List Price
  • $115/SF
  • 21 Days On Market

  Current Estimated Value $429,981

  Last Listing Agent Sam Watkins COLOR Real Estate

  204 Delaplain Rd, Winchester, KY 40391
• 

  

  /16

  Est $165,295 Not Listed For Sale

  2584 Irvine Rd, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 990 Sq Ft
  • Built 1950

  2584 Irvine Rd, Winchester, KY 40391

  Last Sold Summary

  • 35% Above List Price
  • $123/SF
  • 29 Days On Market

  • Last Sold Price $122,000
  • Aug 22, 2024

  Last Listing Agent Veronica Norwood All Star Real Estate, Inc.
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  /44

  $349,500

  • 4 Beds
  • 3 Baths
  • 2,800 Sq Ft

  221 W Hickman St, Winchester, KY 40391

  Step into a home where history and beauty meet in the most charming way. This stunning, fully remodeled historic home offers over 3,400 square feet of thoughtfully renewed living space, blending timeless character with elegant modern updates. From the moment you walk inside, you'll feel the warmth and romance of a home that has been lovingly restored while still honoring its original charm.

  Brandon Hedinger Keller Williams Bluegrass Realty

  221 W Hickman St, Winchester, KY 40391
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  /48

  $550,000 Sold Sep 04, 2025

  594 Earlymeade Dr, Winchester, KY 40391

  • 5 Beds
  • 3 Baths
  • 3,489 Sq Ft
  • Built 2007

  Last Sold Summary

  • 4% Below List Price
  • $158/SF
  • 43 Days On Market

  Current Estimated Value $565,639

  Last Listing Agent Alyssa M Boley Coldwell Banker McMahan

  594 Earlymeade Dr, Winchester, KY 40391

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