Winchester, KY Homes

• 

  

  

  /47

  Est $613,343

  Not Listed For Sale

  1305 Irvine Rd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 3,020 Sq Ft
  • Built 1918

  1305 Irvine Rd, Winchester, KY 40391

  Last Sold Summary

  • 406 Days On Market
• 

  

  

  /21

  $139,000

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 886 Sq Ft

  9 Linden Ave, Winchester, KY 40391

  Back on Market due to: Buyer's financing fell through. Very nice home with hardwood floors in main areas featuring 2 bedrooms, 1 bath, permanent stairs to attic that has windows and could possibly be 2 bedrooms or bonus room. Enjoy your coffee on the front porch in the mornings! The storage shed in the back yard conveys with property. Home being sold as-is, where-is, sale pending court approval,

  Emily Hacker-Todd CENTURY 21 Advantage Realty

  9 Linden Ave, Winchester, KY 40391
• 

  

  

  /63

  $445,000

  Sold May 22, 2026

  1911 Trapp-Goffs Corner Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,288 Sq Ft
  • Built 2000

  Last Sold Summary

  • 3% Below List Price
  • $345/SF
  • 51 Days On Market

  Last Listing Agent Cheri Shaffer Lifstyl Real Estate

  1911 Trapp-Goffs Corner Rd, Winchester, KY 40391
• 

  

  

  /99

  Est $266,084

  Not Listed For Sale

  514 E Broadway St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,394 Sq Ft
  • Built 1960

  514 E Broadway St, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market
• 

  

  /2

  $188,500

  Pending

  • Land
  • 12.1 Acres
  • $15,579 per Acre

  155 Spring Ridge Way, Winchester, KY 40391

  Great opportunity to develop/ build on 12+ acres. The property has three street stubs adjoining it. Three different concepts are included under documents. They are- R-1E, 4000 sq. Ft lots for 80 lots R-4- 14 Duplexes and 6 4plexes for 52 units R-1D - 6000 sq. Ft. Lots for 41 lots. Utilities are to the property and sewer availability should not be an issue.

  Jo Gawthrop Keller Williams Bluegrass Realty

  155 Spring Ridge Way, Winchester, KY 40391
• 

  

  /48

  $341,500

  Sold Jun 27, 2025

  401 Cedar Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,834 Sq Ft
  • Built 1996

  Last Sold Summary

  • 1% Above List Price
  • $186/SF
  • 2 Days On Market

  Current Estimated Value $350,317

  Last Listing Agent Geneva Wilder Stewart & Co Realty LLC

  401 Cedar Ct, Winchester, KY 40391
• 

  

  /30

  Est $196,019

  Not Listed For Sale

  1 Apache Trail, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,584 Sq Ft
  • Built 1969

  1 Apache Trail, Winchester, KY 40391

  Last Sold Summary

  • 10 Days On Market
• 

  

  /10

  $591,650

  New Construction Pending

  • 3 Beds
  • 2.5 Baths
  • 2,200 Sq Ft

  104 Bella Shae Way, Winchester, KY 40391

  Welcome Home to the Winchester Floor Plan by CP Builders. This elegant ranch home features all-brick construction, a welcoming front porch, and a two-car garage. Step inside and be greeted by soaring 9-foot ceilings and a spacious open floor plan. The split bedroom design offers privacy and comfort, with a luxurious primary suite boasting an ensuite bathroom and a walk-in closet. Enjoy easy

  Shane Underwood Keller Williams Commonwealth

  104 Bella Shae Way, Winchester, KY 40391
• 

  /2

  $610,000

  Sold Aug 29, 2025

  4560 Pine Ridge Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,848 Sq Ft
  • Built 1905

  Last Sold Summary

  • $330/SF
  • 1 Day On Market

  Current Estimated Value $630,348

  Last Listing Agent Natalie Avant Berkshire Hathaway HomeServices Foster Realtors

  4560 Pine Ridge Rd, Winchester, KY 40391
• 

  

  /27

  Est $210,839

  Not Listed For Sale

  7 Pocahontas Trail, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,550 Sq Ft
  • Built 1969

  7 Pocahontas Trail, Winchester, KY 40391

  Last Sold Summary

  • 7 Days On Market
• 

  

  /15

  $284,900

  $12K PRICE DROP Pending

  • 4 Beds
  • 2.5 Baths
  • 1,693 Sq Ft

  327 Newcastle Ln, Winchester, KY 40391

  PRICE REDUCTION!!! Perfect for investment or primary residence. Welcome home to this cozy cute FOUR bedroom house with 2 full bath/ 1 half bath! Rare to find- Primary bedroom and full bath on first floor. Large living area with plenty of sunlight through insulated windows and skylights. This open floorpan also showcases a nice open staircase that overlooks the main floor. Upstairs are 3

  Huong Dunn Bluegrass Property Exchange

  327 Newcastle Ln, Winchester, KY 40391
• 

  

  /32

  $263,000

  Sold Sep 05, 2025

  2 Chickadee Ln, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,397 Sq Ft
  • Built 1960

  Last Sold Summary

  • 1% Above List Price
  • $188/SF
  • 2 Days On Market

  Current Estimated Value $266,968

  Last Listing Agent Ashley Spencer Keller Williams Commonwealth

  2 Chickadee Ln, Winchester, KY 40391
• 

  

  /57

  Est $204,635

  Not Listed For Sale

  17 Hiawatha Trail, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,000 Sq Ft
  • Built 1968

  17 Hiawatha Trail, Winchester, KY 40391

  Last Sold Summary

  • 32 Days On Market
• 

  

  /33

  $339,900

  Pending

  • 3 Beds
  • 2.5 Baths
  • 1,608 Sq Ft

  740 Pilot Ridge Ln, Winchester, KY 40391

  Tucked away on 1.25 fully fenced acres, this custom-built home offers some of the most breathtaking views in Winchester. Designed with charm and comfort in mind, this 3-bedroom, 2.5-bath home blends modern convenience with timeless farmhouse style. Step inside to an open, inviting layout filled with natural light and warm finishes throughout. The spacious vaulted master suite is a true retreat,

  Holly Goeing The Agency

  740 Pilot Ridge Ln, Winchester, KY 40391
• 

  

  /35

  $325,000

  Sold Nov 21, 2025

  130 Hibiscus Ln, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 1,900 Sq Ft
  • Built 2000

  Last Sold Summary

  • 7% Below List Price
  • $171/SF
  • 19 Days On Market

  Current Estimated Value $341,455

  Last Listing Agent Ashley Barreto Indigo & Co

  130 Hibiscus Ln, Winchester, KY 40391
• 

  

  /15

  Est $206,563

  Not Listed For Sale

  13 Hiawatha Trail, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,006 Sq Ft
  • Built 1968

  13 Hiawatha Trail, Winchester, KY 40391

  Last Sold Summary

  • 50 Days On Market
• 

  

  /31

  $249,900

  • 3 Beds
  • 2 Baths
  • 1,284 Sq Ft

  312 Buffalo Trace, Winchester, KY 40391

  Welcome home to this inviting 3 Bedroom 2 bath home situated on a spacious 0.41 Acre lot. This home offers the perfect blend of comfort and functionality that offers a well designed layout with ample living space. Step into the spacious living room where beautiful Hardwood floors add warmth, character,and timeless appeal. Perfect for relaxing with family or entertaining guests. The Master bedroom

  Paula Cole The Agency

  312 Buffalo Trace, Winchester, KY 40391
• 

  

  /31

  $292,500

  Sold May 22, 2026

  306 Trapp-Goffs Corner Rd, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,840 Sq Ft
  • Built 1974

  Last Sold Summary

  • 2% Below List Price
  • $159/SF
  • 1 Day On Market

  Current Estimated Value $299,774

  Last Listing Agent Patrick Arvin Keller Williams Commonwealth

  306 Trapp-Goffs Corner Rd, Winchester, KY 40391
• 

  

  /29

  Est $227,021

  Not Listed For Sale

  46 Hiawatha Trail, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Built 1970

  46 Hiawatha Trail, Winchester, KY 40391

  Last Sold Summary

  • 2 Days On Market
• 

  /2

  $1,800,000

  $2M PRICE INCREASE

  • Land
  • 4.36 Acres
  • $412,844 per Acre

  722 Colby Rd Unit 1, 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 1, Winchester, KY 40391
• 

  

  /22

  $255,000

  Sold May 26, 2026

  35 Cherokee Ct, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,332 Sq Ft
  • Built 1968

  Last Sold Summary

  • 6% Below List Price
  • $109/SF
  • 123 Days On Market

  Current Estimated Value $259,838

  Last Listing Agent Brenda Rue Keller Williams Bluegrass Realty

  35 Cherokee Ct, Winchester, KY 40391
• 

  

  /24

  Est $257,210

  Not Listed For Sale

  108 Dixon Way, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,377 Sq Ft
  • Built 2006

  108 Dixon Way, Winchester, KY 40391

  Last Sold Summary

  • 124 Days On Market
• 

  

  /103

  $3,500,000

  $170K PRICE INCREASE

  • 6 Beds
  • 5.5 Baths
  • 7,274 Sq Ft

  5045 Van Meter Rd, Winchester, KY 40391

  Welcome to a truly exceptional 78-acre estate, where luxury and nature converge. This custom-built, three-story home, completed in 2006 , offers 7274 sq ft of meticulously designed living space. With 6 bedrooms and 5.5 bathrooms, there's ample room for family and guests. The impressive 2432 sq ft, temperature-controlled 5-car garage provides extensive space for vehicles and hobbies. Beyond the

  The Prather Team - Michael Prather Keller Williams Bluegrass Realty

  5045 Van Meter Rd, Winchester, KY 40391
• 

  

  /51

  $303,000

  Sold Jan 16, 2026

  22 N Bloomfield Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,913 Sq Ft
  • Built 1919

  Last Sold Summary

  • 5% Below List Price
  • $158/SF
  • 16 Days On Market

  Current Estimated Value $307,297

  Last Listing Agent Libby VanMeter Marshall Lane Real Estate - Lexington

  22 N Bloomfield Rd, Winchester, KY 40391
• 

  

  /19

  Est $221,588

  Not Listed For Sale

  170 Center Dr, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,517 Sq Ft
  • Built 1961

  170 Center Dr, Winchester, KY 40391

  Last Sold Summary

  • 52 Days On Market
• 

  /2

  $100,000

  $10K PRICE DROP

  • Land
  • 16,117 Sq Ft
  • $270,270 per Acre

  225 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

  225 Jacob Ct, Winchester, KY 40391
• 

  /2

  $89,000

  Sold Dec 18, 2025

  13067 Irvine Rd, Winchester, KY 40391

  • Land
  • 7.86 Acres
  • $11,323 per Acre

  Last Sold Summary

  • 78 Days On Market

  Last Listing Agent Mendel Tipton Natural Bridge Realty

  13067 Irvine Rd, Winchester, KY 40391
• 

  

  /58

  Est $206,581

  Not Listed For Sale

  219 Locust Grove Rd, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,191 Sq Ft
  • Built 1955

  219 Locust Grove Rd, Winchester, KY 40391

  Last Sold Summary

  • 27 Days On Market
• 

  

  /7

  $365,900

  New Construction $4K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,558 Sq Ft

  204 Jett Dr, Winchester, KY 40391

  New Construction, don't wait this one will not last, 3 bed/2 bath ranch, great floor plan, close to I-64 and I-75, lexington, richmond, call today! All colors, fixtures, granite, siding, outside landscaping, stone/brick, deck size, flooring have been ordered, New photos will be posted as house construction continues

  Mila Ensor Ensor Real Estate, LLC

  204 Jett Dr, Winchester, KY 40391
• 

  /2

  $4,900,000

  Sold Dec 23, 2025

  175 Chatham Place, Winchester, KY 40391

  • 2 Beds
  • 3 Baths
  • 37,192 Sq Ft
  • Built 2007

  Last Sold Summary

  • 13% Below List Price
  • $132/SF
  • 111 Days On Market

  Current Estimated Value $5,022,391

  Last Listing Agent Garry Milton Milton and Associates Real Estate

  175 Chatham Place, Winchester, KY 40391
• 

  

  /29

  Est $203,259

  Not Listed For Sale

  505 Bob o Link Dr, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,228 Sq Ft
  • Built 1960

  505 Bob o Link Dr, Winchester, KY 40391

  Last Sold Summary

  • 22 Days On Market
• 

  /2

  $195,000

  $2M PRICE DROP

  6699 Boonesboro Rd, Winchester, KY 40391

  READY TO BUILD OR HUNT? We have the perfect spot for you! Mostly wooded 8.35 acres, tract 2B, of green, treed, Bluegrass Heaven. Close proximity to I 75 and I 64 as well as Lexington, Richmond, and Winchester. Bring your own builder or we can help you find one!

  Jennifer Ray RE/MAX Elite Lexington

  6699 Boonesboro Rd, Winchester, KY 40391
• 

  

  /51

  $340,000

  Sold Oct 30, 2025

  356 Boone Ave, Winchester, KY 40391

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

  Last Sold Summary

  • 5% Below List Price
  • $106/SF
  • 30 Days On Market

  Current Estimated Value $352,551

  Last Listing Agent Elizabeth Hodge Lifstyl Real Estate

  356 Boone Ave, Winchester, KY 40391
• 

  

  /12

  Est $215,628

  Not Listed For Sale

  303 Hummingbird Rd, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,169 Sq Ft
  • Built 1960

  303 Hummingbird Rd, Winchester, KY 40391

  Last Sold Summary

  • 27 Days On Market
• 

  

  /3

  $670,000

  New Construction

  • 3 Beds
  • 2 Baths
  • 2,261 Sq Ft

  113 Bella Shae Way, Winchester, KY 40391

  Introducing the Hampton, a beautiful all-brick ranch home. This 3-bedroom, 2-bath split-bedroom design offers both privacy and comfort. The spacious primary suite is a true retreat, featuring a luxurious ensuite with double vanities, a walk-in shower, and dual walk-in closets. The open-concept kitchen and great room are perfect for entertaining, highlighted by a gas log fireplace, a large kitchen

  Shane Underwood Keller Williams Commonwealth

  113 Bella Shae Way, Winchester, KY 40391
• 

  

  /28

  $131,000

  Sold Mar 12, 2026

  46 Judy Ann Ct, Winchester, KY 40391

  • 2 Beds
  • 1.5 Baths
  • 960 Sq Ft

  Last Sold Summary

  • 3% Below List Price
  • $136/SF
  • 0 Days On Market

  Current Estimated Value $136,182

  Last Listing Agent Lukas Owens The Brokerage

  46 Judy Ann Ct, Winchester, KY 40391
• 

  

  /7

  Est $190,443

  Not Listed For Sale

  301 Hummingbird Rd, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,106 Sq Ft
  • Built 1955

  301 Hummingbird Rd, Winchester, KY 40391

  Last Sold Summary

  • 41 Days On Market
• 

  

  /100

  $429,900

  • 4 Beds
  • 2.5 Baths
  • 1,500 Sq Ft

  240 Athens Boonesboro Rd, Winchester, KY 40391

  Rare Investment Opportunity on the Kentucky River! Two incredible homes on 3 beautiful acres — endless potential awaits. Live in the charming log cabin and let the second home pay the mortgage with its long term, reliable tenant already in place. This property offers room to dream: -Build a future campground -Create a private riverside retreat -Expand for additional rentals -Or simply enjoy your

  Darrell Tackett Dream Maker Realty, LLC

  240 Athens Boonesboro Rd, Winchester, KY 40391
• 

  

  /4

  $315,000

  Sold Jun 30, 2025

  4550 Schollsville Rd Unit 40391, Winchester, KY 40391

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Mila Ensor Ensor Real Estate, LLC

  4550 Schollsville Rd Unit 40391, Winchester, KY 40391
• 

  

  /30

  Est $176,370

  Not Listed For Sale

  222 Locust Grove Rd, Winchester, KY 40391

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

  222 Locust Grove Rd, Winchester, KY 40391

  Last Sold Summary

  • 2 Days On Market

Showing Results 281 - 320, Page 8 of 18