Winchester, KY Homes

• 

  

  

  /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
• 

  

  

  /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 $143,535

  Last Listing Agent Samantha Gray National Real Estate

  37 Ashland Ave, Winchester, KY 40391
• 

  

  

  /26

  Est $262,909

  Not Listed For Sale

  20 Jackson St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,650 Sq Ft
  • Built 1940

  20 Jackson St, Winchester, KY 40391

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Jonathan Wood HomeLand Real Estate Inc - Mt Sterling
• 

  

  

  /35

  $258,900

  $16K 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
• 

  

  

  /20

  $217,500

  Sold Sep 30, 2025

  511 Acadia Way, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 2001

  Last Sold Summary

  • 3% Below List Price
  • $155/SF
  • 28 Days On Market

  Current Estimated Value $223,397

  Last Listing Agent Tyler I Back The Brokerage

  511 Acadia Way, Winchester, KY 40391
• 

  

  /25

  Est $217,723

  Not Listed For Sale

  21 Vine St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,080 Sq Ft
  • Built 1960

  21 Vine St, Winchester, KY 40391

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Kymberly McCreary eXp Realty, LLC
• 

  /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
• 

  

  /39

  $400,000

  Sold Aug 25, 2026

  215 Delaplain Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,304 Sq Ft
  • Built 1980

  Last Sold Summary

  • 4% Below List Price
  • $174/SF
  • 23 Days On Market

  Current Estimated Value $410,957

  Last Listing Agent Alyssa Ryan Marshall Lane Real Estate - Lexington

  215 Delaplain Rd, Winchester, KY 40391
• 

  

  /39

  Est $255,200

  Not Listed For Sale

  217 E Washington St, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,183 Sq Ft
  • Built 1940

  217 E Washington St, Winchester, KY 40391

  Last Sold Summary

  • 21 Days On Market

  Last Listing Agent Joshua Lynch The Brokerage
• 

  

  /56

  $249,000

  $6K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,664 Sq Ft

  127 Bay Hill Dr, Winchester, KY 40391

  Welcome home to this spacious, low-maintenance townhome offering 3 levels of living space in a well established neighborhood. Thoughtfully maintained, a 3 year old roof, with recently replaced windows. This home offers plenty of room to spread out while keeping everyday living comfortable and convenient. The main level features a generously sized kitchen and family room with plenty of space for

  Josh Wood Freedom Realty & Property Management

  127 Bay Hill Dr, Winchester, KY 40391
• 

  /2

  $99,500

  Sold Dec 01, 2025

  1295 Sewell Shop Rd, Winchester, KY 40391

  • Land
  • 8.39 Acres
  • $11,859 per Acre

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Zella Rosenthal Tom Goebel & Company

  1295 Sewell Shop Rd, Winchester, KY 40391
• 

  

  /29

  Est $252,274

  Not Listed For Sale

  167 E Washington St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,763 Sq Ft
  • Built 1940

  167 E Washington St, Winchester, KY 40391

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Kymberly McCreary eXp Realty, LLC
• 

  

  /25

  $110,000

  • Land
  • 4.14 Acres
  • $26,570 per Acre

  3999 Bybee Rd, Winchester, KY 40391

  Discover the perfect setting for your dream home on this beautiful 4.14-acre tract at 3999 Bybee Road, Winchester, KY 40391. Nestled among the rolling hills of Kentucky's Bluegrass region, this picturesque property offers stunning panoramic countryside views and the peace and privacy you've been searching for. The gently rolling terrain provides multiple potential building sites, giving you the

  Kristey Wood Keller Williams Legacy Group

  3999 Bybee Rd, Winchester, KY 40391
• 

  

  /13

  $140,000

  Sold Nov 24, 2025

  220 Pendleton St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 902 Sq Ft

  Last Sold Summary

  • 24% Below List Price
  • $155/SF
  • 37 Days On Market

  Current Estimated Value $140,063

  Last Listing Agent Steve Adams Steven D Adams Real Estate Services, LLC

  220 Pendleton St, Winchester, KY 40391
• 

  

  /26

  Est $194,870

  Not Listed For Sale

  150 W Broadway St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,696 Sq Ft
  • Built 1940

  150 W Broadway St, Winchester, KY 40391

  Last Sold Summary

  • 39 Days On Market

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

  

  /20

  $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
• 

  

  /55

  $340,000

  Sold Aug 14, 2026

  27 Hampton Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,835 Sq Ft
  • Built 1958

  Last Sold Summary

  • 6% Below List Price
  • $120/SF
  • 58 Days On Market

  Current Estimated Value $350,829

  Last Listing Agent Terra Long Keller Williams Commonwealth

  27 Hampton Ave, Winchester, KY 40391
• 

  

  /18

  Est $123,582

  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
• 

  

  /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
• 

  

  /21

  $195,000

  Sold Apr 10, 2026

  319 Essex Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,224 Sq Ft
  • Built 2000

  Last Sold Summary

  • 2% Below List Price
  • $159/SF
  • 3 Days On Market

  Current Estimated Value $199,729

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

  319 Essex Ct, Winchester, KY 40391
• 

  

  /11

  Est $134,931

  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
• 

  /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
• 

  /2

  $59,000

  Sold Dec 16, 2025

  1515 Sewell Shop Rd, Winchester, KY 40391

  • Land
  • 2.83 Acres
  • $20,848 per Acre

  Last Sold Summary

  • 2% Below List Price
  • 3 Days On Market

  Last Listing Agent Zella Rosenthal Tom Goebel & Company

  1515 Sewell Shop Rd, Winchester, KY 40391
• 

  

  /20

  Est $212,669

  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
• 

  

  /27

  $146,900

  $6K 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
• 

  

  /53

  $439,000

  Sold Dec 29, 2025

  129 Lana Ln, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,844 Sq Ft
  • Built 1968

  Last Sold Summary

  • 7% Below List Price
  • $154/SF
  • 110 Days On Market

  Current Estimated Value $433,777

  Last Listing Agent Jo Gawthrop Keller Williams Bluegrass Realty

  129 Lana Ln, Winchester, KY 40391
• 

  

  /22

  Est $193,171

  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
• 

  

  /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
• 

  

  /37

  $295,000

  Sold Dec 27, 2025

  115 College St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,839 Sq Ft
  • Built 1940

  Last Sold Summary

  • 2% Below List Price
  • $160/SF
  • 0 Days On Market

  Current Estimated Value $291,364

  Last Listing Agent Zova Rothchild Keller Williams Legacy Group

  115 College St, Winchester, KY 40391
• 

  

  /74

  Est $551,044

  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
• 

  

  /68

  $2,750,000

  • 8 Beds
  • 7.5 Baths
  • 13,433 Sq Ft

  4664 Lexington Rd, Winchester, KY 40391

  Welcome to 4664 Lexington Road—a magnificent private estate on 35 rolling acres of pristine Kentucky countryside that feels worlds away, yet sits just minutes from the charm of Winchester and the vibrancy of Lexington. A stately stone entry welcomes you down a graceful, winding driveway to a sweeping circular drive, leading to a grand 13,000+ square-foot residence built in 1997 with timeless

  Adam Boardman Block + Lot Homes

  4664 Lexington Rd, Winchester, KY 40391
• 

  

  /78

  $660,000

  Sold Dec 10, 2025

  420 Alexis Way, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,770 Sq Ft
  • Built 2022

  Last Sold Summary

  • 5% Below List Price
  • $238/SF
  • 26 Days On Market

  Current Estimated Value $689,907

  Last Listing Agent Edwin Burden McCormick Realty Inc.

  420 Alexis Way, Winchester, KY 40391
• 

  

  /43

  Est $271,296

  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
• 

  

  /15

  $450,000

  • Land
  • 9,583 Sq Ft
  • $2,045,455 per Acre

  1320 Fulton Rd, Winchester, KY 40391

  Prime commercial opportunity in an ideally located area of Winchester! This versatile commercial building offers an excellent location for an established business, growing company, or investor seeking a property with strong potential. Conveniently situated with easy access to major roadways and surrounding communities, the property provides excellent visibility and accessibility for customers and

  Holly Spradlin KY Realty Co

  1320 Fulton Rd, Winchester, KY 40391
• 

  

  /21

  $430,000

  Sold Mar 09, 2026

  870 Pilot View Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft
  • Built 2022

  Last Sold Summary

  • 2% Below List Price
  • $274/SF
  • 31 Days On Market

  Current Estimated Value $439,393

  Last Listing Agent Chelsea Morguson McCallie Real Estate

  870 Pilot View Rd, Winchester, KY 40391
• 

  

  /27

  Est $205,679

  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
• 

  

  /40

  $244,000

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

  54 Locust Dr, Winchester, KY 40391

  SHORT SALE OPPORTUNITY! 54 Locust Dr. is an all-brick ranch in Westland Park offering 3 bedrooms, 2 baths and 1,692 sq. ft. of finished living space, plus a full unfinished basement. The home features hardwood flooring, a 2-car attached garage, fenced backyard and covered patio. Previous owners completed structural work in the basement that includes a transferable lifetime warranty. The home

  Natalie Avant Berkshire Hathaway HomeServices Foster Realtors

  54 Locust Dr, Winchester, KY 40391
• 

  

  /21

  $207,500

  Sold Sep 10, 2026

  128 Abbeywood Ct, Winchester, KY 40391

  • 3 Beds
  • 3.5 Baths
  • 1,892 Sq Ft
  • Built 2000

  Last Sold Summary

  • 8% Below List Price
  • $110/SF
  • 1 Day On Market

  Current Estimated Value $224,246

  Last Listing Agent Judd Hisel ERA Select Real Estate

  128 Abbeywood Ct, Winchester, KY 40391
• 

  

  /27

  Est $370,411

  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
• 

  

  /5

  $29,000

  $4K PRICE DROP

  • Land
  • 20,037 Sq Ft
  • $63,043 per Acre

  102 Augusta Dr, Winchester, KY 40391

  This is a beautiful area to build your dream home. Backs up to a golf course for a magnificent view. Just minutes from Fort Boonesborough National Park.

  Dale Hatton Dream Maker Realty, LLC

  102 Augusta Dr, Winchester, KY 40391

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