Winchester, KY Homes

• 

  

  

  /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
• 

  

  

  /33

  $240,000

  Sold Sep 10, 2025

  752 Wayland Dr, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,472 Sq Ft
  • Built 1969

  Last Sold Summary

  • 11% Below List Price
  • $97/SF
  • 18 Days On Market

  Current Estimated Value $266,196

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate

  752 Wayland Dr, Winchester, KY 40391
• 

  

  

  /18

  Est $128,877

  Not Listed For Sale

  27 Oliver St, Winchester, KY 40391

  • 2 Beds
  • 2 Baths
  • 1,242 Sq Ft
  • Built 1940

  27 Oliver St, Winchester, KY 40391

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent Daniel Ellis Metro Max Realty
• 

  

  

  /24

  $245,000

  Pending

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

  5977 Mount Sterling Rd, Winchester, KY 40391

  Welcome home to this charming 3 bedroom, 2 bath property situated on a beautiful 1.45 acre lot, offering the perfect blend of privacy and convenience. Freshly painted walls throughout, this move in ready home features stylish granite countertops and inviting living spaces. Step outside to enjoy the mature trees that provide shade and character, along with a nicely fenced backyard that's perfect

  Jennifer Guyton White Realty, LLC

  5977 Mount Sterling Rd, 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 $275,764

  Last Listing Agent Joshua Davis The Agency

  434 Paisley Ct, Winchester, KY 40391
• 

  

  /11

  Est $133,872

  Not Listed For Sale

  30 Madison Ave, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft
  • Built 1996

  30 Madison Ave, Winchester, KY 40391

  Last Sold Summary

  • 18 Days On Market

  Last Listing Agent Michelle Newman Team Pannell Real Estate
• 

  

  /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
• 

  

  /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 $187,391

  Last Listing Agent Garnett Davis Tom Goebel & Company

  616 Boone Ave, Winchester, KY 40391
• 

  

  /20

  Est $210,947

  Not Listed For Sale

  2 1st St, Winchester, KY 40391

  • 5 Beds
  • 2 Baths
  • 1,776 Sq Ft
  • Built 1945

  2 1st St, Winchester, KY 40391

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Whitney Ensor Ensor Real Estate, LLC
• 

  

  /9

  $1,350,000

  $350K PRICE INCREASE

  • Land
  • 3.02 Acres
  • $447,020 per Acre

  155 April Way, Winchester, KY 40391

  Ideally located along the heart of Bypass Road (ADT: 24,801) in Winchester, Kentucky between and surrounding Kroger and Walmart shopping centers. These lots are offered as 1+ acres and may be subdivided. Winchester, KY is the county seat of Clark County, KY and is part of the Lexington-Fayette KY Metropolitan Statistical Area, and is supported by such industries such as Amazon, Ale-8-One, and

  Greg Leveridge Block + Lot Homes

  155 April Way, 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 $263,461

  Last Listing Agent Monica Marcum Century 21 Pinnacle

  410 Wellington Way, Winchester, KY 40391
• 

  

  /16

  Est $190,522

  Not Listed For Sale

  123 2nd St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,298 Sq Ft

  123 2nd St, Winchester, KY 40391

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Roscoe Riley Blu Horizon Real Estate
• 

  

  /35

  $268,900

  $6K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 849 Sq Ft

  955 Right Angle Rd, Winchester, KY 40391

  Newly renovated Cabin sitting on +- 5 acres. Renovations began in 2024 and were completed in 2026. An ideal property for a first-time home buyer or anyone looking for a remote quiet location located within 20 minutes of downtown Winchester.

  Rhett Hughes WTC Realty LLC

  955 Right Angle Rd, 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 $236,474

  Last Listing Agent Nena Honaker Tom Goebel & Company

  318 Buffalo Trace, Winchester, KY 40391
• 

  

  /22

  Est $191,152

  Not Listed For Sale

  160 Autumn Ct, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,287 Sq Ft
  • Built 1960

  160 Autumn Ct, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Phillip Neeley-Morrison Bluegrass Home Group
• 

  /2

  $100,000

  $10K PRICE DROP

  • Land
  • 13,503 Sq Ft
  • $322,581 per Acre

  215 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

  215 Duclair Dr, 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 $309,962

  Last Listing Agent Rob Bolton Christies International Real Estate Bluegrass

  113 Strawberry Ln, Winchester, KY 40391
• 

  

  /74

  Est $546,648

  Not Listed For Sale

  4 Moundale Ave, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,941 Sq Ft
  • Built 1945

  4 Moundale Ave, Winchester, KY 40391

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Janna Chalfant Smith United Real Estate Bluegrass
• 

  

  /12

  $239,000

  $116K PRICE DROP

  • 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. 1130 has a new HVAC. Selling As Is Inspections Welcome.

  Brian Hatfield Coldwell Banker McMahan

  1128 Dale Dr, Winchester, KY 40391
• 

  

  /31

  $240,200

  Sold Oct 28, 2025

  203 Inverness Ln, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,935 Sq Ft
  • Built 2004

  Last Sold Summary

  • 2% Below List Price
  • $124/SF
  • 16 Days On Market

  Current Estimated Value $255,864

  Last Listing Agent Kymberly McCreary eXp Realty, LLC

  203 Inverness Ln, Winchester, KY 40391
• 

  

  /43

  Est $270,949

  Not Listed For Sale

  373 Crescent Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,009 Sq Ft
  • Built 1940

  373 Crescent Ave, Winchester, KY 40391

  Last Sold Summary

  • 28 Days On Market

  Last Listing Agent Janna Chalfant Smith United Real Estate Bluegrass
• 

  

  /7

  $185,000

  Pending

  • Land
  • 2.71 Acres
  • $68,190 per Acre

  2191 Mcclure Rd, Winchester, KY 40391

  2.7 acres of vacant land offering a great opportunity to build your dream home. Enjoy a peaceful setting with room to spread out while remaining conveniently located to nearby amenities.

  Michelle Blackburn RE/MAX Creative, Winchester

  2191 Mcclure 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 $225,015

  Last Listing Agent Frank Mulder Tru Life Real Estate

  357 Silverton Way, Winchester, KY 40391
• 

  

  /27

  Est $204,103

  Not Listed For Sale

  374 S Main St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 972 Sq Ft
  • Built 1940

  374 S Main St, Winchester, KY 40391

  Last Sold Summary

  • 206 Days On Market

  Last Listing Agent Mila Ensor Ensor Real Estate, LLC
• 

  

  /5

  $154,900

  • Land
  • 2.53 Acres
  • $61,250 per Acre

  750 Craig Crossing Unit Lot 7, Winchester, KY 40391

  Great opportunity to own a prime lot in the exclusive Thoroughbred Estates, Winchester's most exclusive subdivision. Located between Winchester and Lexington this location is close to shopping, schools, hospitals and interstates. If your tired of living on a postage stamp lot then this lot is for you. Select your dream house plan and select your builder before it's too late.

  Keith Wilson Coldwell Banker McMahan

  750 Craig Crossing Unit Lot 7, 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 $850,390

  Last Listing Agent Jonathan Noel Noel Auctioneers and Real Estate Advisors

  7075 Ecton Rd, Winchester, KY 40391
• 

  

  /27

  Est $388,776

  Not Listed For Sale

  200 Moundale Ave, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 3,428 Sq Ft
  • Built 1960

  200 Moundale Ave, Winchester, KY 40391

  Last Sold Summary

  • 84 Days On Market

  Last Listing Agent Kelly Nisbet Coldwell Banker McMahan
• 

  /2

  $100,000

  $10K PRICE DROP

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

  155 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

  155 Duclair Dr, 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 $337,444

  Last Listing Agent Brittany Nester RO&CO Real Estate

  106 Gibson Way, Winchester, KY 40391
• 

  

  /28

  Est $236,630

  Not Listed For Sale

  358 Crescent Ave, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,764 Sq Ft
  • Built 1950

  358 Crescent Ave, Winchester, KY 40391

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Lucy Martin Jenkins United Real Estate Bluegrass
• 

  

  /42

  $399,000

  $21K PRICE DROP Pending

  • 3 Beds
  • 2.5 Baths
  • 2,235 Sq Ft

  19 Fontaine Blvd, Winchester, KY 40391

  Charming story and a half home nestled in a well established neighborhood, featuring beautiful hardwood floors and an updated kichen with modern finishes and ample cabinet space. Relax and entertain with ease on the screened back deck overlooking the large fenced backyard and enjoy the added bonus of a charming gazebo, perect for outdoor gathers or peaceful evenings. This well maintaned home

  Kathryn Cheuvront Coldwell Banker McMahan

  19 Fontaine Blvd, Winchester, KY 40391
• 

  

  /36

  $472,500

  Sold Sep 09, 2025

  208 Royal Oak Dr, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,593 Sq Ft
  • Built 2007

  Last Sold Summary

  • 1% Above List Price
  • $182/SF
  • 1 Day On Market

  Current Estimated Value $489,207

  Last Listing Agent Megan McCoy Keller Williams Legacy Group

  208 Royal Oak Dr, Winchester, KY 40391
• 

  

  /77

  Est $286,607

  Not Listed For Sale

  328 S Main St, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,709 Sq Ft
  • Built 1900

  328 S Main St, Winchester, KY 40391

  Last Sold Summary

  • 26 Days On Market

  Last Listing Agent Josh Wood Freedom Realty & Property Management
• 

  

  /27

  $149,900

  $3K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,680 Sq Ft

  65 Fitch Ave, Winchester, KY 40391

  Lovely older home, located witin waking distance to collage park whice offers Pickle Ball, Pool, Tennis, play gound and Walking Trail, also walking distance to Historic Downtown Winchester, with a little love house brings large rooms and a nostlogic atmosphire, take a look, view today, this a a great price for 3 bedrooms, 1 1/2 baths, nice back yard, with parking, call today! Selling "AS IS",

  Mila Ensor Ensor Real Estate, LLC

  65 Fitch Ave, 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 $257,208

  Last Listing Agent Amy Diamond ERA Select Real Estate

  414 Wellington Way, Winchester, KY 40391
• 

  

  /57

  Est $374,087

  Not Listed For Sale

  286 S Main St, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 3,689 Sq Ft
  • Built 1910

  286 S Main St, Winchester, KY 40391

  Last Sold Summary

  • 9 Days On Market

  Last Listing Agent Kelly Nisbet Coldwell Banker McMahan
• 

  

  /3

  $825,000

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,995 Sq Ft

  111 Bella Shae Way, Winchester, KY 40391

  Welcome Home to the Park Place Floor Plan by CP Builders. This elegant ranch home features all-brick construction and a thoughtfully designed split bedroom layout for maximum privacy. The open floor plan seamlessly connects the living, dining, and kitchen areas, creating a warm and inviting atmosphere. Thespacious kitchen is a chef's dream, boasting a large island, a convenient pantry, and a

  Shane Underwood Keller Williams Commonwealth

  111 Bella Shae Way, Winchester, KY 40391
• 

  

  /15

  $139,000

  Sold May 29, 2026

  37 Ashland Ave, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 904 Sq Ft
  • Built 1940

  Last Sold Summary

  • $154/SF
  • 5 Days On Market

  Current Estimated Value $139,441

  Last Listing Agent Samantha Gray National Real Estate

  37 Ashland Ave, Winchester, KY 40391
• 

  

  /34

  Est $281,367

  Not Listed For Sale

  312 S Main St, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 2,355 Sq Ft
  • Built 1920

  312 S Main St, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Susan Baldwin Threshold Real Estate Services
• 

  

  /29

  $294,900

  $5K PRICE DROP Pending

  • 5 Beds
  • 3 Baths
  • 3,314 Sq Ft

  4603 Paris Rd, Winchester, KY 40391

  If you've been looking for an amazing "light" renovation opportunity, this is it! Over 3300 sq ft w tons of character situated on an acre of land w gorgeous mature trees. *Seller's are contributing $5,000 towards buyer's prepaids/closing costs.* Flooring, roof, HVAC heat pumps are under 6 years old. New windows & gutters installed May 2026. Under 5 minutes to 64. Don't let this one pass you by.

  Jeff Green Keller Williams Commonwealth

  4603 Paris Rd, Winchester, KY 40391

Showing Results 561 - 600, Page 15 of 18