Homes in ZIP Code 40391

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  /70

  $335,000 Pending

  • 6 Beds
  • 4 Baths
  • 3,544 Sq Ft

  297 S Main St, Winchester, KY 40391

  Completely remodeled duplex offering over 3,400 sq. ft. of living space! Featuring 6 bedrooms and 4 bathrooms, this property has been fully updated with granite countertops, new appliances, fresh flooring, and paint throughout. The layout is bright and inviting with plenty of natural light. Enjoy the covered front porch, separate utility room, and unfinished basement for extra storage or future

  Silvia Torres Tru Life Real Estate

  297 S Main St, Winchester, KY 40391
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  /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 $352,950

  Last Listing Agent Janna Chalfant Smith United Real Estate Bluegrass

  205 Chardonnay Ct, Winchester, KY 40391
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  /38

  Est $368,474 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

  • $128/SF
  • 2 Days On Market

  Last Sold Price $367,000

  Last Listing Agent Kevin Bradley Keller Williams Legacy Group
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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
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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 $212,312

  Last Listing Agent Aaron Kendall Lifstyl Real Estate

  305 Geronimo Ct, Winchester, KY 40391
• 

  

  /76

  Est $759,764 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

  • 10% Above List Price
  • $241/SF
  • 2 Days On Market

  Last Sold Price $690,000

  Last Listing Agent Cassie Foley CENTURY 21 Advantage Realty
• 

  

  /12

  $305,000

  • 5 Beds
  • 2 Baths
  • 2,214 Sq Ft

  55 Hillcrest Dr, Winchester, KY 40391

  All-brick ranch with a full walk-out basement! This charming home offers excellent potential for the right buyer. The main level features three bedrooms, a full bath, a comfortable living room, and an eat-in kitchen. The walk-out basement expands the living space with two additional bedrooms, full bath, family room with a kitchenette area, utility room, and ample storage with built-in shelving.

  Nina Vanetten RE/MAX Elite Lexington

  55 Hillcrest Dr, Winchester, KY 40391
• 

  

  /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 $319,295

  Last Listing Agent Jessica Noto Century 21 Advantage Realty - Georgetown

  104 Teakwood Ct, Winchester, KY 40391
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  /32

  Est $280,662 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

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

  Last Sold Price $264,900

  Last Listing Agent Serena Cassidy Coldwell Banker McMahan
• 

  

  /12

  $299,900

  • 4 Beds
  • 4 Baths
  • 2,072 Sq Ft

  1128 Dale Dr, Winchester, KY 40391

  Duplex. Both units are being sold together. Great income-producing potential. Each side offers a nice sized vaulted Great room that opens to the kitchen, 2 bedrooms, 1.5 baths, a laundry room, and a 1-car garage. Nice private backyard for side with lots of trees. Selling As Is Inspections Welcome.

  Brian Hatfield Coldwell Banker McMahan

  1128 Dale Dr, Winchester, KY 40391
• 

  /2

  $195,000 Sold May 15, 2025

  Unlisted Address

  • 4 Beds
  • 2 Baths
  • 1,822 Sq Ft
  • Built 1980

  Last Sold Summary

  • $107/SF

  Current Estimated Value $214,647

  Last Listing Agent Null Non-Member Non-Member Office

  Unlisted Address
• 

  

  /53

  Est $307,256 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

  • 12% Above List Price
  • $244/SF
  • 45 Days On Market

  Last Sold Price $275,000

  Last Listing Agent Sabina Chambers Semonin Realty
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  /36

  $369,000

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft

  133 Shala-Mar Rue, Winchester, KY 40391

  Welcome to your next home in one of Clark County's most sought after communities—Shala Mar Estates. This beautifully updated 3-bedroom, 2-bathroom residence offers the perfect blend of comfort, style, and modern convenience. The expansive primary suite is a true retreat, featuring a stunning ensuite bathroom with a brand new soaking tub and a separate tiled shower. Two additional bedrooms provide

  Nena Honaker Tom Goebel & Company

  133 Shala-Mar Rue, Winchester, KY 40391
• 

  

  /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 $290,446

  Last Listing Agent Kymberly McCreary EXP Realty, LLC

  707 Terry Dr, Winchester, KY 40391
• 

  

  /23

  Est $287,480 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

  • 17% Above List Price
  • $151/SF
  • 3 Days On Market

  Last Sold Price $245,000

  Last Listing Agent Louis Baldwin Threshold Real Estate Services
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  /55

  $339,900

  • 3 Beds
  • 2 Baths
  • 1,222 Sq Ft

  1291 Muddy Creek Rd, Winchester, KY 40391

  Rare opportunity with TWO lots!! This cozy ranch home, originally built in 1952, but was completely remodeled down to the studs in 2023 (per Seller), offering the charm of an established home with the feel of modern construction. The open concept floor plan features a spacious family room flowing seamlessly into the kitchen, perfect for every day, living and entertaining. The layout provides

  Terri McGraw FC Tucker Bluegrass

  1291 Muddy Creek Rd, 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 $554,375

  Last Listing Agent Jarran Thomas The Agency

  154 Hawthorne Dr, Winchester, KY 40391
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  /78

  Est $506,795 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

  • 11% Below List Price
  • $212/SF
  • 42 Days On Market

  Last Sold Price $570,000

  Last Listing Agent Elizabeth Torchia Caswell Prewitt Realty, Inc
• 

  

  /50

  $359,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,080 Sq Ft

  175 Overlooking Dr, Winchester, KY 40391

  Relax on your front porch and enjoy the view of the lake or have a barbecue on your oversized rear deck and enjoy the countryside views. This 3-bedroom, 2-bathroom home features Living Room, Dining Room, Family Room, has two cozy fireplaces for your entertainment. Home has a full partially finished basement with a large recreation room and plenty of space to add additional rooms if needed. To

  Keith Wilson Coldwell Banker McMahan

  175 Overlooking 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 $374,817

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  714 Concord Ave, Winchester, KY 40391
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  /76

  Est $480,022 Not Listed For Sale

  110 White Conkwright Rd, Winchester, KY 40391

  • 5 Beds
  • 3 Baths
  • 1,623 Sq Ft
  • Built 1979

  110 White Conkwright Rd, Winchester, KY 40391

  Last Sold Summary

  • 7% Above List Price
  • $276/SF
  • 102 Days On Market

  Last Sold Price $448,244

  Last Listing Agent Kayla Pasqualini Reliance One Realty
• 

  

  /97

  $339,900

  • 3 Beds
  • 2.5 Baths
  • 1,794 Sq Ft

  322 S Burns Ave, Winchester, KY 40391

  This beautiful 1.5-story home offers all the charm of downtown in a small town, with a library, park, and restaurants nearby. Plus, just minutes to Lexington when the city is calling your name. This home has been remodeled for modern living, featuring an open floor plan. There is plenty of room for entertaining with a beautiful, well-equipped kitchen and a large island open to both the dining

  Nancy Hibbitts CENTURY 21 Advantage Realty

  322 S Burns Ave, Winchester, KY 40391
• 

  

  /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 $1,182,344

  Last Listing Agent Amanda Marcum Berkshire Hathaway HomeServices Foster Realtors

  6237 Bybee Rd, Winchester, KY 40391
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  /39

  Est $336,998 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

  • 5% Above List Price
  • $225/SF
  • 2 Days On Market

  Last Sold Price $320,000

  Last Listing Agent Megan McCoy Keller Williams Legacy Group
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  /67

  $325,000

  • 3 Beds
  • 3 Baths
  • 2,821 Sq Ft

  3622 Stamper Dr, Winchester, KY 40391

  This lovely and unique home sits at the end of a quiet street in a secluded circle and backs up to a privacy fenced yard and greenspace right in the heart of town. With recently installed vinyl siding, gutters and gutter guard properties like this are hard to find and the unique amenities inside truly set this home apart. Step through the front door to discover a spacious great room with gleaming

  Josh Wood Freedom Realty & Property Management

  3622 Stamper Dr, Winchester, KY 40391
• 

  

  /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 $322,707

  Last Listing Agent Mila Ensor Ensor Real Estate, LLC

  172 Buckingham Ln, Winchester, KY 40391
• 

  

  /36

  Est $450,315 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

  • 16% Above List Price
  • $134/SF
  • 47 Days On Market

  Last Sold Price $388,000

  Last Listing Agent Wayne Elkins RE/MAX
• 

  

  /34

  $300,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,531 Sq Ft

  1508 Ford Hampton Rd, Winchester, KY 40391

  Welcome home to this adorable 2 bedroom, 1 bathroom farmhouse on 5 peaceful acres. Inside, the layout is open and inviting with LVP and hardwood flooring throughout with a tiled bath. The kitchen and family room flow together and feature beautiful exposed wood beams that are hundreds of years old and reclaimed from an old church. A wood-burning stove in the family room adds warmth and character

  Michelle Blackburn RE/MAX Creative, Winchester

  1508 Ford Hampton Rd, 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 $358,158

  Last Listing Agent Bradford Queen Bluegrass Sotheby's International Realty

  19 Snowfall Dr, Winchester, KY 40391
• 

  

  /34

  Est $346,577 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

  • 1% Below List Price
  • $214/SF
  • 2 Days On Market

  Last Sold Price $349,500

  Last Listing Agent Hannah Simpkins National Real Estate
• 

  

  /51

  $775,000 Open Sun 1PM - 3PM

  • 5 Beds
  • 3.5 Baths
  • 2,904 Sq Ft

  1783 Gay Evans Rd, Winchester, KY 40391

  Welcome to your dream homestead retreat! Tucked away on 7.27 beautiful acres, this stunning 5-bedroom, 4-bath home offers the perfect blend of comfort, function, and country living. From the inviting front porch sunsets to the resort-style outdoor space, this property has everything you've been searching for. Step inside to the two story foyer that leads to an open-concept main level featuring

  Lucy Martin Jenkins United Real Estate Bluegrass

  1783 Gay Evans Rd, Winchester, KY 40391
• 

  

  /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 $363,753

  Last Listing Agent Patrick Arvin Keller Williams Commonwealth

  148 Gibson Way, Winchester, KY 40391
• 

  

  /41

  Est $341,829 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

  • 1% Above List Price
  • $219/SF
  • 44 Days On Market

  Last Sold Price $340,000

  Last Listing Agent Patrick Doyle Lifstyl Real Estate
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  /100

  $1,789,000

  • 3 Beds
  • 2.5 Baths
  • 4,518 Sq Ft

  3166 Colby Rd, Winchester, KY 40391

  PRICE REDUCED and sellers are offering a 25,000 allowance at closing to spend as you wish!! Welcome to this beautiful 33± acre estate, offering the perfect blend of country charm, modern comfort, and endless opportunity. The stately historical home, built in 1919, retains timeless character and can be registered with the Historical Home Society. Enjoy stunning mountain views — located at one of

  Alyssa M Boley Coldwell Banker McMahan

  3166 Colby Rd, Winchester, KY 40391
• 

  

  /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 $210,220

  Last Listing Agent Ashley Barreto Indigo & Co

  34 N Burns Ave, Winchester, KY 40391
• 

  

  /38

  Est $348,286 Not Listed For Sale

  875 Miller Hunt Rd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,904 Sq Ft
  • Built 1976

  875 Miller Hunt Rd, Winchester, KY 40391

  Last Sold Summary

  • 12% Above List Price
  • $163/SF
  • 150 Days On Market

  Last Sold Price $310,000

  Last Listing Agent Amy J Lopez CENTURY 21 Advantage Realty
• 

  /2

  $1,200,000

  • Land
  • 24.15 Acres
  • $49,689 per Acre

  1395 Two Mile Rd, Winchester, KY 40391

  PLANNED DEVELOPMENT INVESTMENT INVESTMENT OPPORTUNITY! Already zoned Planned Development! There is an approximately 24 acre tract zoned for all forms of Residential use. (In addition there is an approximately 21 acre Residential tract that adjoins the Winchester Country Club. The two Residential tracts have access to gravity flow sewer. Sewer maps available. The remaining

  Garnett Davis Tom Goebel & Company

  1395 Two Mile Rd, Winchester, KY 40391
• 

  

  /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 $214,856

  Last Listing Agent Nena Honaker Tom Goebel & Company

  15 Holly Ave, Winchester, KY 40391
• 

  

  /42

  Est $310,097 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

  • 3% Above List Price
  • $202/SF
  • 1 Day On Market

  Last Sold Price $300,000

  Last Listing Agent Joyce Ratliff Tom Goebel & Company
• 

  

  /6

  $171,000

  • 2 Beds
  • 1 Bath
  • 870 Sq Ft

  102 W Hickman St, Winchester, KY 40391

  102 W Hickman St, Winchester, KY 40391Cozy and full of potential! This 11⁄2-story home offers 2 bedrooms and 1 bathroom, making it a great fit for a small household or as part of a rental investment portfolio. Currently used as a rental, the property features a functional layout with living spaces on the main floor and additional space upstairs. Located on a quiet street yet close to downtown

  David Espinosa Bluegrass Realty Pros, Inc

  102 W Hickman St, Winchester, KY 40391

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