Homes in ZIP Code 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
• 

  

  

  /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
• 

  

  

  /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
• 

  

  

  /33

  Est $340,816

  Not Listed For Sale

  543 S Maple St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,527 Sq Ft
  • Built 1946

  543 S Maple St, Winchester, KY 40391

  Last Sold Summary

  • 38 Days On Market

  Last Listing Agent Lucy Martin Jenkins 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
• 

  

  /29

  $235,000

  Sold Feb 09, 2026

  142 Sturbridge Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,220 Sq Ft
  • Built 2005

  Last Sold Summary

  • 6% Below List Price
  • $193/SF
  • 1 Day On Market

  Current Estimated Value $245,507

  Last Listing Agent Donna Mink Mink Realty

  142 Sturbridge Ln, Winchester, KY 40391
• 

  

  /28

  Est $242,882

  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
• 

  

  /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
• 

  

  /57

  $775,000

  Sold Mar 02, 2026

  1700 Cabin Creek Rd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,695 Sq Ft
  • Built 1994

  Last Sold Summary

  • $288/SF
  • 33 Days On Market

  Current Estimated Value $787,625

  Last Listing Agent Alysia Niva Century 21 Advantage Realty - Georgetown

  1700 Cabin Creek Rd, Winchester, KY 40391
• 

  

  /77

  Est $292,954

  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
• 

  

  /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
• 

  

  /32

  $217,500

  Sold Jul 13, 2026

  525 Colby Ridge Blvd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,197 Sq Ft
  • Built 2001

  Last Sold Summary

  • 1% Below List Price
  • $182/SF
  • 11 Days On Market

  Current Estimated Value $218,405

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate

  525 Colby Ridge Blvd, Winchester, KY 40391
• 

  

  /57

  Est $376,557

  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
• 

  /2

  $110,000

  • Land
  • 13,939 Sq Ft
  • $343,750 per Acre

  135 Jacob Ct, 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

  135 Jacob Ct, Winchester, KY 40391
• 

  

  /79

  $204,000

  Sold Oct 30, 2025

  133 S Burns Ave, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 3,295 Sq Ft
  • Built 1915

  Last Sold Summary

  • 18% Below List Price
  • $62/SF
  • 20 Days On Market

  Current Estimated Value $244,786

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  133 S Burns Ave, Winchester, KY 40391
• 

  

  /34

  Est $278,704

  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
• 

  

  /33

  $225,000

  • 3 Beds
  • 2.5 Baths
  • 1,522 Sq Ft

  115 Quail Ridge Rd, Winchester, KY 40391

  Looking for low-maintenance living without giving up space? This Winchester townhouse offers three bedrooms, 2.5 baths and a comfortable two-story layout with room to spread out. The main level features a spacious living room with a fireplace, dining area, kitchen and half bath. Just off the dining area, the back deck gives you a nice spot to relax or enjoy some time outside. Upstairs, the

  Michelle Blackburn RE/MAX Creative, Winchester

  115 Quail Ridge Rd, Winchester, KY 40391
• 

  

  /27

  $135,000

  Sold Sep 09, 2026

  60 Fitch Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,775 Sq Ft
  • Built 1950

  Last Sold Summary

  • 10% Below List Price
  • $76/SF
  • 5 Days On Market

  Current Estimated Value $207,315

  Last Listing Agent Mila Ensor Ensor Real Estate, LLC

  60 Fitch Ave, Winchester, KY 40391
• 

  

  /52

  Est $278,837

  Not Listed For Sale

  14 Lisle Ln, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,673 Sq Ft
  • Built 1955

  14 Lisle Ln, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Meredith Walker Bluegrass Sotheby's International Realty
• 

  /2

  $110,000

  • Land
  • 13,939 Sq Ft
  • $343,750 per Acre

  115 Jacob Ct, 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

  115 Jacob Ct, Winchester, KY 40391
• 

  

  /62

  $260,000

  Sold Jun 09, 2026

  144 Holly Ave, Winchester, KY 40391

  • 8 Beds
  • 5 Baths
  • 3,637 Sq Ft
  • Built 2001

  Last Sold Summary

  • 19% Below List Price
  • $71/SF
  • 69 Days On Market

  Current Estimated Value $270,917

  Last Listing Agent Shane Underwood Keller Williams Commonwealth

  144 Holly Ave, Winchester, KY 40391
• 

  

  /20

  Est $223,083

  Not Listed For Sale

  18 Lisle Ln, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,082 Sq Ft
  • Built 1950

  18 Lisle Ln, Winchester, KY 40391

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Lukas Owens The Brokerage
• 

  

  /23

  $184,900

  $20K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,046 Sq Ft

  143 Spruce Ct, Winchester, KY 40391

  Welcome to 143 Spruce Court in Winchester! This charming brick ranch offers comfortable one-level living with 3 bedrooms and 1 full bath. Inside, you'll find beautiful hardwood flooring and a warm, inviting layout. Outside, enjoy a well-manicured large corner lot (0.20 ac) with plenty of space to relax or entertain. Conveniently located near a local park featuring a splash park and recreational

  John Wilson Bluegrass Properties Group

  143 Spruce Ct, Winchester, KY 40391
• 

  

  /28

  $246,000

  Sold Nov 06, 2025

  204 Moss Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,430 Sq Ft
  • Built 1998

  Last Sold Summary

  • 3% Above List Price
  • $172/SF
  • 1 Day On Market

  Current Estimated Value $249,303

  Last Listing Agent Brooke Martin RO&CO Real Estate

  204 Moss Ct, Winchester, KY 40391
• 

  

  /54

  Est $331,527

  Not Listed For Sale

  35 Lisle Ln, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,816 Sq Ft
  • Built 1953

  35 Lisle Ln, Winchester, KY 40391

  Last Sold Summary

  • 27 Days On Market

  Last Listing Agent Whitney Ensor Ensor Real Estate, LLC
• 

  

  /23

  $204,900

  Pending

  • 3 Beds
  • 1 Bath
  • 1,128 Sq Ft

  38 Mackay Ave, Winchester, KY 40391

  Beautiful 3-bedroom, 1-bath home located at the end of a quiet, well established neighborhood within walking distance to downtown Winchester. This home features hardwood floors, a versatile in home office or bonus room, and several recent upgrades including a new stove, microwave, refrigerator, cabinets, and HVAC (1 year old). The property offers a backyard with a storage shed, providing

  Nena Honaker Tom Goebel & Company

  38 Mackay Ave, Winchester, KY 40391
• 

  

  /26

  $390,000

  Sold Jul 22, 2026

  178 Hawthorne Dr, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,156 Sq Ft
  • Built 2018

  Last Sold Summary

  • $181/SF
  • 6 Days On Market

  Current Estimated Value $393,652

  Last Listing Agent Tiffani Casey Waizenhofer Real Estate

  178 Hawthorne Dr, Winchester, KY 40391
• 

  

  /28

  Est $379,155

  Not Listed For Sale

  512 Boone Ave, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 3,149 Sq Ft
  • Built 1950

  512 Boone Ave, Winchester, KY 40391

  Last Sold Summary

  • 58 Days On Market

  Last Listing Agent Jordan James Lifstyl Real Estate
• 

  

  /4

  $635,000

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,537 Sq Ft

  422 Alexis Way, Winchester, KY 40391

  Introducing the Denver, a gorgeous all-brick ranch home offering 4 bedrooms and 2.5 baths, designed for both luxury and practicality. With its stunning curb appeal, front porch, and beam accents, this home makes a lasting first impression. Inside, the split-bedroom layout offers privacy and space for everyone, with a large primary suite featuring a walk-in closet, soaking tub, separate shower,

  Shane Underwood Keller Williams Commonwealth

  422 Alexis Way, Winchester, KY 40391
• 

  

  /43

  $450,000

  Sold May 26, 2026

  222 Ashton Oak Way, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 3,444 Sq Ft
  • Built 2006

  Last Sold Summary

  • $131/SF
  • 4 Days On Market

  Current Estimated Value $453,186

  Last Listing Agent Mila Ensor Ensor Real Estate, LLC

  222 Ashton Oak Way, Winchester, KY 40391
• 

  

  /49

  Est $411,351

  Not Listed For Sale

  228 Moundale Ave, Winchester, KY 40391

  • 3 Beds
  • 3.5 Baths
  • 3,200 Sq Ft
  • Built 1940

  228 Moundale Ave, Winchester, KY 40391

  Last Sold Summary

  • 261 Days On Market

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

  

  /23

  $199,900

  $6K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,154 Sq Ft

  606 College St, Winchester, KY 40391

  606 College Street is such a cute Winchester home, with more space than you might expect and so many thoughtful improvements already completed. This 2-bedroom, 1-bath ranch offers 1,154 square feet, a bright kitchen with a breakfast bar and newer appliances, an open living and dining area, and a renovated bathroom. New LVP flooring, fresh paint, light fixtures, and new kitchen and bathroom

  Alyssa Ryan Marshall Lane Real Estate - Lexington

  606 College St, Winchester, KY 40391
• 

  

  /52

  $230,000

  Sold Jan 20, 2026

  19 Cherokee Ct, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,134 Sq Ft
  • Built 1968

  Last Sold Summary

  • 2% Above List Price
  • $203/SF
  • 2 Days On Market

  Current Estimated Value $229,839

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  19 Cherokee Ct, Winchester, KY 40391
• 

  

  /34

  Est $348,434

  Not Listed For Sale

  214 Boone Ave, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,928 Sq Ft
  • Built 1930

  214 Boone Ave, Winchester, KY 40391

  Last Sold Summary

  • 107 Days On Market

  Last Listing Agent Whitney Ensor Ensor Real Estate, LLC
• 

  

  /22

  $229,500

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,130 Sq Ft

  527 Hidden Hills Way, Winchester, KY 40391

  NEW roof, NEW kitchen appliances, NEW deck, and more! Welcome to 527 Hidden Hills Way! Located on a quiet cul-de-sac, this renovated one level home is ready for you to move right in. Vaulted ceilings give an open and airy feel, while fresh paint throughout offers a neutral palette for any design style. The spacious kitchen includes plenty of oak cabinetry, a separate pantry, stainless steel

  Jarran Thomas The Agency

  527 Hidden Hills Way, Winchester, KY 40391
• 

  

  /36

  $202,000

  Sold Mar 18, 2026

  58 Hughes Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft

  Last Sold Summary

  • 6% Below List Price
  • $139/SF
  • 15 Days On Market

  Current Estimated Value $201,159

  Last Listing Agent E Anthony Phillips RE/MAX Creative Realty

  58 Hughes Ave, Winchester, KY 40391
• 

  

  /65

  Est $354,295

  Not Listed For Sale

  408 S Maple St, Winchester, KY 40391

  • 5 Beds
  • 3 Baths
  • 3,372 Sq Ft
  • Built 1910

  408 S Maple St, Winchester, KY 40391

  Last Sold Summary

  • 62 Days On Market

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate
• 

  /2

  $110,000

  • Land
  • 21,780 Sq Ft
  • $220,000 per Acre

  260 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

  260 Duclair Dr, Winchester, KY 40391
• 

  

  /39

  $395,000

  Sold Jun 18, 2026

  18 Casa Landa Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,883 Sq Ft
  • Built 1975

  Last Sold Summary

  • $210/SF
  • 0 Days On Market

  Current Estimated Value $390,635

  Last Listing Agent Steve Charles Freedom Realty & Property Management

  18 Casa Landa Way, Winchester, KY 40391
• 

  

  /57

  Est $441,239

  Not Listed For Sale

  402 S Maple St, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 3,864 Sq Ft
  • Built 1896

  402 S Maple St, Winchester, KY 40391

  Last Sold Summary

  • 24 Days On Market

  Last Listing Agent Kristy Hall The Agency

Showing Results 601 - 640, Page 16 of 18