Homes in ZIP Code 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
• 

  

  

  /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
• 

  

  

  /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
• 

  

  

  /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
• 

  

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  /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
• 

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  /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
• 

  

  /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
• 

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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

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