Winchester, KY Homes

• 

  

  

  /41

  Est $260,547

  Not Listed For Sale

  254 S Highland St, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 3,395 Sq Ft
  • Built 1935

  254 S Highland St, Winchester, KY 40391

  Last Sold Summary

  • 10 Days On Market

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

  

  

  /94

  $675,000

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,659 Sq Ft

  1477 Sewell Shop Rd, Winchester, KY 40391

  Rare opportunity to purchase a new construction home in the country on almost 5 acres in Clark County! Brand new modern farmhouse featuring 4 bedrooms, 3.5 baths, front and rear covered porches with stamped concrete floors and stained wood ceilings, 2 car garage, gas vented fireplace, and much more! From the inviting high vaulted ceiling foyer you will notice the tray ceilings with faux beams in

  Jason Townsend Kentucky Residential Real Estate, LLC

  1477 Sewell Shop Rd, Winchester, KY 40391
• 

  

  

  /54

  $649,900

  Sold Aug 06, 2026

  1480 Irvine Rd, Winchester, KY 40391

  • 3 Beds
  • 3.5 Baths
  • 3,388 Sq Ft
  • Built 1920

  Last Sold Summary

  • 13% Below List Price
  • $192/SF
  • 87 Days On Market

  Current Estimated Value $634,336

  Last Listing Agent Ivanna Barko National Real Estate

  1480 Irvine Rd, Winchester, KY 40391
• 

  

  

  /28

  Est $243,098

  Not Listed For Sale

  252 S Highland St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,944 Sq Ft
  • Built 1935

  252 S Highland St, Winchester, KY 40391

  Last Sold Summary

  • 17 Days On Market

  Last Listing Agent Austina Bruton The Howard Realty Co
• 

  

  

  /21

  $135,000

  • 2 Beds
  • 1 Bath
  • 807 Sq Ft

  3208 Ford Hampton Rd, Winchester, KY 40391

  Set on a half-acre in a rural Winchester setting, this 2-bedroom, 1-bath home offers an efficient one-level layout with approximately 807 square feet of living space. The eat-in kitchen provides a comfortable spot for everyday meals, while main-level laundry hookups add convenience. Front and rear porches extend the living space outdoors and offer places to enjoy the surrounding trees,

  Bob Sophiea eXp Realty, LLC

  3208 Ford Hampton Rd, Winchester, KY 40391
• 

  

  /20

  $339,000

  Sold Aug 04, 2026

  107 Gibson Way, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,266 Sq Ft
  • Built 2020

  Last Sold Summary

  • 8% Below List Price
  • $150/SF
  • 26 Days On Market

  Current Estimated Value $347,006

  Last Listing Agent Vanessa Highland Stewart & Co Realty LLC

  107 Gibson Way, Winchester, KY 40391
• 

  

  /17

  Est $179,180

  Not Listed For Sale

  220 Jackson St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,228 Sq Ft
  • Built 1940

  220 Jackson St, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Joanna Howell Bluegrass Properties Group
• 

  

  /19

  $280,000

  $15K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,344 Sq Ft

  405 Nick Ln, Winchester, KY 40391

  Come see this beautiful 13-acre property in the Historic Boonesborough area of Clark County, offering peaceful country living with the convenience of being just minutes from Winchester, Richmond, and Lexington. The property features a 2-bedroom, 1-bath home with 1,344 sq. ft., surrounded by beautiful acreage with plenty of room for animals, recreation, gardening, or simply enjoying the outdoors.

  Taylor Norton McCallie Real Estate

  405 Nick Ln, Winchester, KY 40391
• 

  

  /33

  $208,000

  Sold May 15, 2026

  59 Holiday Rd, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,050 Sq Ft
  • Built 1985

  Last Sold Summary

  • 1% Below List Price
  • $198/SF
  • 6 Days On Market

  Current Estimated Value $212,911

  Last Listing Agent Kathy Burton Coldwell Banker McMahan

  59 Holiday Rd, Winchester, KY 40391
• 

  

  /24

  Est $196,820

  Not Listed For Sale

  54 Winn Ave, Winchester, KY 40391

  • 5 Beds
  • 2 Baths
  • 1,530 Sq Ft
  • Built 1940

  54 Winn Ave, Winchester, KY 40391

  Last Sold Summary

  • 90 Days On Market

  Last Listing Agent Lukas Owens The Brokerage
• 

  

  /40

  $289,900

  $16K PRICE DROP

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

  428 Waycross Dr, Winchester, KY 40391

  Wow! Pack your belongings and get ready to move! Your dream house just hit the market and It is going to go quick. Imagine sitting on the back deck , sipping your favorite beverage while your children and pets play safely in this large fenced in back yard. Or set up your home theatre in the spacious finished basement. This home has so much to offer, very spacious with the primary bed room and

  Wayne Elkins RE/MAX Creative Realty

  428 Waycross Dr, Winchester, KY 40391
• 

  

  /75

  $490,000

  Sold Sep 26, 2025

  497 Goose Creek Rd, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 2,972 Sq Ft
  • Built 1993

  Last Sold Summary

  • 1% Below List Price
  • $165/SF
  • 2 Days On Market

  Current Estimated Value $474,838

  Last Listing Agent O Eve Stern Threshold Real Estate Services

  497 Goose Creek Rd, Winchester, KY 40391
• 

  

  /33

  Est $261,573

  Not Listed For Sale

  144 E Broadway St, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,544 Sq Ft
  • Built 1930

  144 E Broadway St, Winchester, KY 40391

  Last Sold Summary

  • 119 Days On Market

  Last Listing Agent Thomas Harper Tom Harper and Associates
• 

  

  /6

  $49,500

  • Land
  • 42,688 Sq Ft
  • $50,510 per Acre

  204 Wigeon Ct, Winchester, KY 40391

  Choose your preferred builder to construct your dream home in Mallard Place. Located in a quiet cul-de-sac at the rear of the subdivision. Only a 20 minute drive to Hamburg/Lexington and only a 5 minute drive to the Winchester Bypass. Enjoy the serenity of living in a private setting AND the convenience of being close to schools, shopping and I-64 and I-75.

  Jim Woodrum RE/MAX Creative, Winchester

  204 Wigeon Ct, Winchester, KY 40391
• 

  

  /24

  $275,000

  Sold Mar 02, 2026

  434 Paisley Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,678 Sq Ft
  • Built 2012

  Last Sold Summary

  • $164/SF
  • 1 Day On Market

  Current Estimated Value $272,993

  Last Listing Agent Joshua Davis The Agency

  434 Paisley Ct, Winchester, KY 40391
• 

  

  /22

  Est $223,993

  Not Listed For Sale

  44 Buckner St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,309 Sq Ft
  • Built 1935

  44 Buckner St, Winchester, KY 40391

  Last Sold Summary

  • 143 Days On Market

  Last Listing Agent W Tyce McCullough Rector Hayden Realtors
• 

  

  /3

  $395,000

  New Construction Pending

  • 3 Beds
  • 2 Baths
  • 1,855 Sq Ft

  205 Evergreen Dr, Winchester, KY 40391

  Introducing The Mulberry floor plan - a beautifully designed proposed construction home in the scenic Locust Hill Acres community. This open-concept floor plan offers the perfect blend of comfort and functionality with 3 bedrooms, 2 full bathrooms, and thoughtful living spaces throughout.The spacious primary suite features a large walk-in closet and a private ensuite bath, providing a

  Rex Hall United Real Estate Bluegrass

  205 Evergreen Dr, Winchester, KY 40391
• 

  

  /27

  $185,000

  Sold Mar 23, 2026

  616 Boone Ave, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,223 Sq Ft
  • Built 1955

  Last Sold Summary

  • 7% Below List Price
  • $151/SF
  • 16 Days On Market

  Current Estimated Value $190,395

  Last Listing Agent Garnett Davis Tom Goebel & Company

  616 Boone Ave, Winchester, KY 40391
• 

  

  /17

  Est $316,320

  Not Listed For Sale

  129 S Highland St, Winchester, KY 40391

  • 6 Beds
  • 4 Baths
  • 3,608 Sq Ft
  • Built 1940

  129 S Highland St, Winchester, KY 40391

  Last Sold Summary

  • 86 Days On Market

  Last Listing Agent Joshua Lynch The Brokerage
• 

  

  /78

  $329,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,480 Sq Ft

  358 Hanover Dr, Winchester, KY 40391

  This beautiful 3 bedroom 2 bath home has so much to offer. The HVAC is only 1 year old and is still under warranty. Appliances are just 3 years old. The backyard has privacy fence all around that was built last year. The home has an above ground pool with a deck built around it. The pool liner and pump was replaced last year. This home is in an excellent location. Just minutes from retail shops,

  Dale Hatton Dream Maker Realty, LLC

  358 Hanover Dr, Winchester, KY 40391
• 

  

  /29

  $262,500

  Sold Feb 18, 2026

  410 Wellington Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,192 Sq Ft
  • Built 2007

  Last Sold Summary

  • 2% Below List Price
  • $220/SF
  • 69 Days On Market

  Current Estimated Value $259,598

  Last Listing Agent Monica Marcum Century 21 Pinnacle

  410 Wellington Way, Winchester, KY 40391
• 

  

  /17

  Est $159,261

  Not Listed For Sale

  21 Franklin Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,006 Sq Ft
  • Built 1940

  21 Franklin Ave, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Austin Polley The Polley Group
• 

  /2

  $600,000

  • Land
  • 6.13 Acres
  • $97,879 per Acre

  722 Colby Rd Unit 2, 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 2, Winchester, KY 40391
• 

  

  /15

  $241,500

  Sold May 01, 2026

  318 Buffalo Trace, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 2026

  Last Sold Summary

  • 3% Above List Price
  • $201/SF
  • 1 Day On Market

  Current Estimated Value $241,205

  Last Listing Agent Nena Honaker Tom Goebel & Company

  318 Buffalo Trace, Winchester, KY 40391
• 

  

  /53

  Est $136,051

  Not Listed For Sale

  307 Jackson St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,629 Sq Ft
  • Built 1950

  307 Jackson St, Winchester, KY 40391

  Last Sold Summary

  • 67 Days On Market

  Last Listing Agent Josh Wood Freedom Realty & Property Management
• 

  

  /32

  $189,000

  $20K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,152 Sq Ft

  32 Jackson St, Winchester, KY 40391

  This beautiful home is located just minutes from historic downtown Winchester. It has 3 spacious bedrooms and 1 full bath. The home has a new roof. When you walk out back you will find an oversized garage. The huge backyard is all fenced in. Make an appointment to tour this one before it's gone.

  Dale Hatton Dream Maker Realty, LLC

  32 Jackson St, Winchester, KY 40391
• 

  

  /32

  $310,000

  Sold May 01, 2026

  113 Strawberry Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,780 Sq Ft
  • Built 2023

  Last Sold Summary

  • 2% Below List Price
  • $174/SF
  • 1 Day On Market

  Current Estimated Value $317,642

  Last Listing Agent Rob Bolton Christies International Real Estate Bluegrass

  113 Strawberry Ln, Winchester, KY 40391
• 

  

  /32

  Est $192,439

  Not Listed For Sale

  230 Winn Ave, Winchester, KY 40391

  • 4 Beds
  • 1.5 Baths
  • 1,400 Sq Ft
  • Built 1940

  230 Winn Ave, Winchester, KY 40391

  Last Sold Summary

  • 73 Days On Market

  Last Listing Agent Cindy Walker Sandy Stuart Realty
• 

  

  /54

  $390,000

  • 4 Beds
  • 1 Bath
  • 2,063 Sq Ft

  7353 Ironworks Rd, Winchester, KY 40391

  7353 Ironworks Road and 3015 Pilot View Road are deeded separate but being sold together. 7353 Ironworks includes the house and barn and 3.348 acres. 3015 Pilot View is the adjacent lot and has 3.38 acres. Total acreage is 6.728. There are 2 bedrooms upstairs that need cosmetic work. The historic barn is large, has electric and needs some repair. There is plenty of space to build your dream home.

  Nancy Smith Rector Hayden Realtors

  7353 Ironworks Rd, Winchester, KY 40391
• 

  

  /19

  $221,000

  Sold Jun 16, 2026

  357 Silverton Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,502 Sq Ft
  • Built 1999

  Last Sold Summary

  • 90,847% Above List Price
  • $147/SF
  • 64 Days On Market

  Current Estimated Value $223,572

  Last Listing Agent Frank Mulder Tru Life Real Estate

  357 Silverton Way, Winchester, KY 40391
• 

  

  /20

  Est $202,248

  Not Listed For Sale

  314 E Broadway St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,188 Sq Ft
  • Built 1950

  314 E Broadway St, Winchester, KY 40391

  Last Sold Summary

  • 22 Days On Market

  Last Listing Agent Amanda Stewart Stewart & Co Realty LLC
• 

  

  /6

  $204,900

  Pending

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft

  500 Hidden Hills Way, Winchester, KY 40391

  Ranch with covered porch, new roof, new appliances and countertops, new bath vanity, new professional paint job. Vaulted ceiling in the living room. Clean and ready for occupancy.

  Sondra Clark Taylor Real Estate, LLC

  500 Hidden Hills Way, Winchester, KY 40391
• 

  

  /44

  $847,000

  Sold Apr 22, 2026

  7075 Ecton Rd, Winchester, KY 40391

  • Land
  • 83.71 Acres
  • $10,118 per Acre

  Last Sold Summary

  • 39 Days On Market

  Current Estimated Value $853,783

  Last Listing Agent Jonathan Noel Noel Auctioneers and Real Estate Advisors

  7075 Ecton Rd, Winchester, KY 40391
• 

  

  /27

  Est $182,987

  Not Listed For Sale

  37 Jackson St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,400 Sq Ft
  • Built 1940

  37 Jackson St, Winchester, KY 40391

  Last Sold Summary

  • 30 Days On Market

  Last Listing Agent O. Debbie Pennington CENTURY 21 Advantage Realty
• 

  

  /22

  $243,500

  • 3 Beds
  • 2.5 Baths
  • 1,856 Sq Ft

  102 Quail Ridge Rd, Winchester, KY 40391

  This move-in ready townhome is located in Greenfield subdivision and sits on a quiet street with no through traffic. On the main level you will find 2 nicely sized bedrooms , 2 full baths, laundry closet along with a fully closed in sun-porch. The living room is spacious and the kitchen is equipped with top notch appliances. Below you will find the walkout basement where there is another bedroom,

  Tracey Goebel Tom Goebel & Company

  102 Quail Ridge Rd, Winchester, KY 40391
• 

  

  /43

  $339,000

  Sold Feb 12, 2026

  106 Gibson Way, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,064 Sq Ft
  • Built 2021

  Last Sold Summary

  • $164/SF
  • 1 Day On Market

  Current Estimated Value $346,220

  Last Listing Agent Brittany Nester RO&CO Real Estate

  106 Gibson Way, Winchester, KY 40391
• 

  

  /23

  Est $218,205

  Not Listed For Sale

  42 Park Ave, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,129 Sq Ft
  • Built 1940

  42 Park Ave, Winchester, KY 40391

  Last Sold Summary

  • 54 Days On Market

  Last Listing Agent Jonathan McMahan Coldwell Banker McMahan
• 

  

  /21

  $99,500

  $5K PRICE DROP Pending

  • 2 Beds
  • 2 Baths
  • 924 Sq Ft

  563 Constitution Dr, Winchester, KY 40391

  Affordable housing! Check out this newly remodeled and updated home! 2 bedroom, 2 full bath! All new flooring, cabinets, vanities, and so much more! No lot rent here! You will own the lot as well, making this a great option for starter, downsizing, investment property (previously rented for $925), or just an affordable home. Nice covered porch, 2 storage sheds, brand new metal roof! $150 per

  Jason Townsend Kentucky Residential Real Estate, LLC

  563 Constitution Dr, Winchester, KY 40391
• 

  

  /32

  $259,000

  Sold Apr 30, 2026

  414 Wellington Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,251 Sq Ft
  • Built 2007

  Last Sold Summary

  • $207/SF
  • 53 Days On Market

  Current Estimated Value $261,792

  Last Listing Agent Amy Diamond ERA Select Real Estate

  414 Wellington Way, Winchester, KY 40391
• 

  

  /43

  Est $153,820

  Not Listed For Sale

  116 Park Ave, Winchester, KY 40391

  • 1 Bed
  • 1 Bath
  • 1,576 Sq Ft
  • Built 1940

  116 Park Ave, Winchester, KY 40391

  Last Sold Summary

  • 23 Days On Market

  Last Listing Agent Christa Joynt Keller Williams Commonwealth

Showing Results 521 - 560, Page 14 of 18