16,348

Winchester, KY Homes

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    • /22

      Est $191,325 Not Listed For Sale

      101 Baldwin Ave, Winchester, KY 40391

      • 3 Beds
      • 1 Bath
      • 925 Sq Ft
      101 Baldwin Ave, Winchester, KY 40391

      Last Sold Summary

      • 23% Above List Price
      • $168/SF
      • 2 Days On Market
      • Last Sold Price $155,000
      • Jul 12, 2024

      Last Listing Agent James Jeffries Brickhouse Real Estate

  • /3

    $42,500 Pending

    • Land
    • 8,712 Sq Ft
    • $212,500 per Acre

    108 Dorset Ln, Winchester, KY 40391

    The restictions state that if it is a ranch plan, there is a minimun of 1300 sq ft. It it is a 1 1/2 story or two story then 1800 sq ft will be required. A two car garage must be attached. Developer will need to approve plans before starting construction This lot is ideal for a walkout basement. Perfect setting for watching the sunsets

    Jo Gawthrop Keller Williams Bluegrass Realty

    108 Dorset Ln, Winchester, KY 40391
  • /28

    $265,000 Sold Jul 02, 2025

    609 Clintonville Rd, Winchester, KY 40391

    • 3 Beds
    • 1.5 Baths
    • 1,305 Sq Ft
    • Built 1980

    Last Sold Summary

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

    Current Estimated Value $268,683

    Last Listing Agent Craig Bridgewater Bridgewater Real Estate

    609 Clintonville Rd, Winchester, KY 40391
    • /28

      Est $231,240 Not Listed For Sale

      916 Muddy Creek Rd, Winchester, KY 40391

      • 3 Beds
      • 2 Baths
      • 1,000 Sq Ft
      • Built 1943
      916 Muddy Creek Rd, Winchester, KY 40391

      Last Sold Summary

      • 19% Above List Price
      • $195/SF
      • 39 Days On Market
      • Last Sold Price $195,000
      • Feb 11, 2025

      Last Listing Agent Janet Jones RE/MAX

  • /12

    $179,000

    • 3 Beds
    • 1 Bath
    • 1,046 Sq Ft

    175 Magnolia St, Winchester, KY 40391

    Two homes on one lot. Informaton in listing is for the home in the front of the lot. Behind this home is a second home consisting of 2 bedrooms, 1, bath, Living room and kitchen. Main home has been completely remodeled but guest home will require major renevations. The home in the front of the property is vacant but there is a tenant in the home in the rear of the property. The lease is month to

    A. Rebecca Woods Woods Realty Group

    175 Magnolia St, Winchester, KY 40391
  • /12

    $9,000 Sold Sep 18, 2025

    406 W Washington St, Winchester, KY 40391

    • 2 Beds
    • 1 Bath
    • 1,428 Sq Ft
    • Built 1945

    Last Sold Summary

    • 10% Below List Price
    • $6/SF
    • 19 Days On Market

    Current Estimated Value $124,932

    Last Listing Agent Jack Rookard Rookard Real Estate Consultants

    406 W Washington St, Winchester, KY 40391
    • /21

      Est $212,535 Not Listed For Sale

      17 Elizabeth St, Winchester, KY 40391

      • 3 Beds
      • 2 Baths
      • 1,450 Sq Ft
      • Built 1950
      17 Elizabeth St, Winchester, KY 40391

      Last Sold Summary

      • 12% Above List Price
      • $130/SF
      • 24 Days On Market
      • Last Sold Price $189,000
      • Feb 28, 2025

      Last Listing Agent Holly Goeing The Agency

  • /25

    $229,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,068 Sq Ft

    213 Short St, Winchester, KY 40391

    Welcome Home! All one level, easy access to this adorable brick ranch featuring 3 bedrooms and 2 full baths! Check out that amazing porch to relax on! Recent total remodel including new HVAC system and all appliances for worry free living for years to come! LVP flooring throughout, tile showers, breakfast bar, off street parking and private driveway, large backyard, and convenient to everything

    Jason Townsend Kentucky Residential Real Estate, LLC

    213 Short St, Winchester, KY 40391
  • /26

    $175,000 Sold Apr 22, 2026

    10 Pocahontas Trail, Winchester, KY 40391

    • 2 Beds
    • 1.5 Baths
    • 924 Sq Ft
    • Built 1988

    Last Sold Summary

    • $189/SF
    • 7 Days On Market

    Current Estimated Value $175,599

    Last Listing Agent Libby VanMeter Marshall Lane Real Estate - Lexington

    10 Pocahontas Trail, Winchester, KY 40391
    • /20

      Est $241,207 Not Listed For Sale

      1121 Muddy Creek Rd, Winchester, KY 40391

      • 3 Beds
      • 1.5 Baths
      • 1,498 Sq Ft
      • Built 1940
      1121 Muddy Creek Rd, Winchester, KY 40391

      Last Sold Summary

      • 21% Above List Price
      • $134/SF
      • 9 Days On Market
      • Last Sold Price $200,000
      • Aug 11, 2023

      Last Listing Agent Cheri Shaffer Keller Williams Commonwealth

  • /7

    $270,000

    • Land
    • 36,590 Sq Ft
    • $321,429 per Acre

    800 Interstate Dr, Winchester, KY 40391

    Visibility, Access, Utilities on site per seller/per plat buyer to verify, zoned B-3. .84 acres located and visible at I-64 exit 96, buyer to verify and satisfy themselves to all aspects and information on property and or inspections sold as is. Buyer to verify water, gas, and electric locations and availability.

    Whitney Ensor Ensor Real Estate, LLC

    800 Interstate Dr, Winchester, KY 40391
  • /79

    $425,000 Sold Feb 23, 2026

    1410 Dry Fork Creek Rd, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 1,064 Sq Ft

    Last Sold Summary

    • 15% Below List Price
    • $399/SF
    • 78 Days On Market

    Last Listing Agent Skyler Lewis Dream Maker Realty, LLC

    1410 Dry Fork Creek Rd, Winchester, KY 40391
    • /79

      Est $202,678 Not Listed For Sale

      205 French Ave, Winchester, KY 40391

      • 3 Beds
      • 1 Bath
      • 946 Sq Ft
      • Built 1959
      205 French Ave, Winchester, KY 40391

      Last Sold Summary

      • 4% Above List Price
      • $206/SF
      • 319 Days On Market
      • Last Sold Price $195,000
      • Nov 20, 2023

      Last Listing Agent Greg Wood Freedom Realty & Property Management

  • /39

    $559,999

    • 4 Beds
    • 5 Baths
    • 4,374 Sq Ft

    600 Boone Ave, Winchester, KY 40391

    Step into the timeless elegance of this stunning Southern antebellum-style home, where classic charm meets modern luxury. Boasting four spacious bedrooms and five beautifully appointed bathrooms, this grand residence offers an unparalleled level of sophistication and comfort. A breathtaking foyer and entryway welcome you with a sweeping staircase, and exquisite architectural details, setting the

    Holly Goeing The Agency

    600 Boone Ave, Winchester, KY 40391
  • /55

    $520,000 Sold May 15, 2025

    427 Calmes Blvd, Winchester, KY 40391

    • 4 Beds
    • 3.5 Baths
    • 4,659 Sq Ft
    • Built 1995

    Last Sold Summary

    • 4% Below List Price
    • $112/SF
    • 61 Days On Market

    Current Estimated Value $535,131

    Last Listing Agent Kymberly McCreary EXP Realty, LLC

    427 Calmes Blvd, Winchester, KY 40391
    • /24

      Est $199,204 Not Listed For Sale

      5 Kentucky St, Winchester, KY 40391

      • 2 Beds
      • 1 Bath
      • 1,634 Sq Ft
      • Built 1930
      5 Kentucky St, Winchester, KY 40391

      Last Sold Summary

      • 18% Above List Price
      • $103/SF
      • 1 Day On Market
      • Last Sold Price $169,000
      • Aug 23, 2023

      Last Listing Agent Melissa Brown Keller Williams Legacy Group

  • /31

    $255,900

    • 3 Beds
    • 2 Baths
    • 1,446 Sq Ft

    123 Sunset Heights, Winchester, KY 40391

    You will love the atmosphere of this remodeled 3 bedroom, 2 bath home located in a secluded location. The large privacy fenced back yard is perfect for the children or pets. Renovated kitchen includes granite countertops, new range, dishwasher , and refrigerator. Home has a full partially finished walk out basement. You will love the large outbuilding as well as storage closet off of carport.

    Keith Wilson Coldwell Banker McMahan

    123 Sunset Heights, Winchester, KY 40391
  • /24

    $188,000 Sold Jan 29, 2026

    27 Ashland Ave, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 1,653 Sq Ft
    • Built 1950

    Last Sold Summary

    • 6% Below List Price
    • $114/SF
    • 112 Days On Market

    Current Estimated Value $187,679

    Last Listing Agent Robin Mobley-Mosher Marshall Lane Real Estate - Lexington

    27 Ashland Ave, Winchester, KY 40391
    • /23

      Est $191,753 Not Listed For Sale

      11 Kentucky St, Winchester, KY 40391

      • 3 Beds
      • 1 Bath
      • 1,708 Sq Ft
      • Built 1920
      11 Kentucky St, Winchester, KY 40391

      Last Sold Summary

      • 79% Above List Price
      • $63/SF
      • 9 Days On Market
      • Last Sold Price $107,000
      • Dec 27, 2023

      Last Listing Agent Darrell Lewis DIY Flat Fee.com

  • /2

    $490,000

    • Land
    • 1.53 Acres
    • $320,261 per Acre

    33-41 Winn Ave, Winchester, KY 40391

    Discover a rare opportunity in downtown Winchester with this assemblage of four vacant lots being sold together as a single offering. Zoned L1 and totaling approximately 1.53 acres, this property presents exceptional potential for redevelopment, infill housing, multiunit residential, mixeduse, or commercial concepts in a central location. Situated just steps from local shops, restaurants,

    Bob Sophiea eXp Realty, LLC

    33-41 Winn Ave, Winchester, KY 40391
  • /26

    $165,000 Sold Apr 23, 2026

    52 Judy Ann Ct, Winchester, KY 40391

    • 3 Beds
    • 1.5 Baths
    • 1,312 Sq Ft
    • Built 1981

    Last Sold Summary

    • $126/SF
    • 0 Days On Market

    Current Estimated Value $166,469

    Last Listing Agent Cathleen Gedeon CENTURY 21 Advantage Realty

    52 Judy Ann Ct, Winchester, KY 40391
    • /18

      Est $111,343 Not Listed For Sale

      129 Kentucky St, Winchester, KY 40391

      • 2 Beds
      • 1 Bath
      • 1,080 Sq Ft
      • Built 1940
      129 Kentucky St, Winchester, KY 40391

      Last Sold Summary

      • 48% Above List Price
      • $69/SF
      • 46 Days On Market
      • Last Sold Price $75,000
      • Jul 11, 2024

      Last Listing Agent Austin Polley The Polley Group

  • /36

    $435,000 Pending

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

    3886 Jackson Ferry Rd, Winchester, KY 40391

    Take in the scenery, enjoy the quite county life, sitting on 5 acres, this brick ranch home offers easy living and peaceful country life. Four Bedrooms 2 full updated baths, Primary Suite with walk in closet, hardwood floors, beautiful brick fireplace in Living Room with Vaulted ceiling and built in shelving, Dining Room, Kitchen with breakfast area granite counter tops and all appliances (range,

    Whitney Ensor Ensor Real Estate, LLC

    3886 Jackson Ferry Rd, Winchester, KY 40391
  • /25

    $375,000 Sold Aug 29, 2025

    317 Hanover Dr, Winchester, KY 40391

    • 5 Beds
    • 3.5 Baths
    • 3,111 Sq Ft
    • Built 2001

    Last Sold Summary

    • 1% Below List Price
    • $121/SF
    • 8 Days On Market

    Current Estimated Value $378,401

    Last Listing Agent Mike Wheatley Bluegrass Properties Group

    317 Hanover Dr, Winchester, KY 40391
    • /15

      Est $198,325 Not Listed For Sale

      20 Elizabeth St, Winchester, KY 40391

      • 3 Beds
      • 2 Baths
      • 1,258 Sq Ft
      • Built 1940
      20 Elizabeth St, Winchester, KY 40391

      Last Sold Summary

      • 3% Above List Price
      • $153/SF
      • 7 Days On Market
      • Last Sold Price $192,588
      • Nov 22, 2024

      Last Listing Agent Jessica Moreno SimpliHOM

  • /2

    $150,000

    • Land
    • 2.16 Acres
    • $69,444 per Acre

    120 Knox Ct, Winchester, KY 40391

    Looking for a place to build a Upscale home in 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

    120 Knox Ct, Winchester, KY 40391
  • /60

    $545,000 Sold Oct 31, 2025

    445 Lynnway Dr, Winchester, KY 40391

    • 4 Beds
    • 3.5 Baths
    • 3,649 Sq Ft
    • Built 1993

    Last Sold Summary

    • $149/SF
    • 4 Days On Market

    Current Estimated Value $543,544

    Last Listing Agent Janna Chalfant Smith United Real Estate Bluegrass

    445 Lynnway Dr, Winchester, KY 40391
    • /17

      Est $221,953 Not Listed For Sale

      102 Kentucky St, Winchester, KY 40391

      • 3 Beds
      • 2 Baths
      • 1,734 Sq Ft
      • Built 1940
      102 Kentucky St, Winchester, KY 40391

      Last Sold Summary

      • 3% Above List Price
      • $124/SF
      • 41 Days On Market
      • Last Sold Price $215,000
      • Jul 01, 2024

      Last Listing Agent Holly Spradlin KY Realty Co

  • /63

    $1,149,000

    • 3 Beds
    • 3.5 Baths
    • 3,672 Sq Ft

    2100 Irvine Rd Unit 40391, Winchester, KY 40391

    Seller will need 48 Hours to show, This log cabin is located on gently rolling 28 acres very few miles from town, you will think you are on vacation in the sparking pool, tastefully landscaped, fireplace in the great room which leads into a in law quarters, large kitchen that has been wonderfully remodeled with extensive detail, master suite is located on first floor, mud room, 3 1/2 baths,

    Mila Ensor Ensor Real Estate, LLC

    2100 Irvine Rd Unit 40391, Winchester, KY 40391
  • /27

    $263,500 Sold Apr 10, 2026

    222 Bracken Ct, Winchester, KY 40391

    • 3 Beds
    • 2.5 Baths
    • 1,456 Sq Ft
    • Built 2006

    Last Sold Summary

    • 2% Below List Price
    • $181/SF
    • 121 Days On Market

    Current Estimated Value $263,905

    Last Listing Agent Jim Woodrum RE/MAX Creative, Winchester

    222 Bracken Ct, Winchester, KY 40391
    • /16

      Est $368,006 Not Listed For Sale

      122 French Ave, Winchester, KY 40391

      • 4 Beds
      • 2 Baths
      • 4,176 Sq Ft
      • Built 1920
      122 French Ave, Winchester, KY 40391

      Last Sold Summary

      • 23% Above List Price
      • $72/SF
      • 4 Days On Market
      • Last Sold Price $300,000
      • Aug 30, 2023

      Last Listing Agent Brenda Sipes Bridgewater Real Estate

  • /47

    $445,500

    • 3 Beds
    • 2.5 Baths
    • 2,961 Sq Ft

    42 Mockingbird Valley Rd, Winchester, KY 40391

    This is a perfect home for EVERY season.....enjoy multiple, interior gathering spaces and the glow and warmth of either the L R or Dining Room fireplace on the main level or the coziness of the mesmerizing fireplace in the lower level family room during the winter. Watch the backyard come alive with rich and lush vegetation during the Spring from the large, glass walled sun room. For Summer, tons

    Markus Cross McCallie Real Estate

    42 Mockingbird Valley Rd, Winchester, KY 40391
  • /27

    $380,000 Sold Nov 10, 2025

    5705 Mount Sterling Rd, Winchester, KY 40391

    • 4 Beds
    • 2.5 Baths
    • 2,980 Sq Ft
    • Built 1971

    Last Sold Summary

    • 5% Below List Price
    • $128/SF
    • 50 Days On Market

    Current Estimated Value $376,818

    Last Listing Agent Dale Hatton Dream Maker Realty, LLC

    5705 Mount Sterling Rd, Winchester, KY 40391
    • /31

      Est $210,243 Not Listed For Sale

      134 Central Ave, Winchester, KY 40391

      • 3 Beds
      • 2 Baths
      • 1,946 Sq Ft
      • Built 1930
      134 Central Ave, Winchester, KY 40391

      Last Sold Summary

      • 50% Above List Price
      • $72/SF
      • 1 Day On Market
      • Last Sold Price $140,000
      • Aug 23, 2024

      Last Listing Agent Mila Ensor Ensor Real Estate, LLC

  • /2

    $100,000

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

    169 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

    169 Duclair Dr, Winchester, KY 40391
  • /102

    $525,000 Sold Dec 22, 2025

    1953 Cabin Creek Rd, Winchester, KY 40391

    • 6 Beds
    • 4.5 Baths
    • 3,846 Sq Ft
    • Built 1980

    Last Sold Summary

    • 4% Below List Price
    • $137/SF
    • 9 Days On Market

    Current Estimated Value $528,414

    Last Listing Agent Josh Wood Freedom Realty & Property Management

    1953 Cabin Creek Rd, Winchester, KY 40391
    • /19

      Est $207,959 Not Listed For Sale

      130 Central Ave, Winchester, KY 40391

      • 3 Beds
      • 1.5 Baths
      • 1,322 Sq Ft
      • Built 1930
      130 Central Ave, Winchester, KY 40391

      Last Sold Summary

      • 12% Above List Price
      • $140/SF
      • 1 Day On Market
      • Last Sold Price $185,000
      • Mar 22, 2024

      Last Listing Agent Lukas Owens The Brokerage

  • /11

    $148,000

    • 3 Beds
    • 1 Bath
    • 864 Sq Ft

    19 3rd St, Winchester, KY 40391

    3BR/1BA | Winchester, KY Affordable single-family homes are hard to come by at this price — here's your chance. This cozy 3-bedroom, 1-bath home in Winchester sits on a generous lot with a large backyard, long driveway with plenty of parking, a welcoming covered front porch, and accessible front entry with both steps and a ramp. it's efficient and easy to maintain — and don't let the square

    Anthony Gigilo ListWithFreedom.com

    19 3rd St, Winchester, KY 40391
  • /28

    $345,000 Sold Jun 19, 2025

    512 Boone Ave, Winchester, KY 40391

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

    Last Sold Summary

    • 14% Below List Price
    • $110/SF
    • 58 Days On Market

    Current Estimated Value $382,030

    Last Listing Agent Jordan James Lifstyl Real Estate

    512 Boone Ave, Winchester, KY 40391
    • /19

      Est $222,001 Not Listed For Sale

      112 Central Ave, Winchester, KY 40391

      • 3 Beds
      • 2 Baths
      • 1,200 Sq Ft
      • Built 2025
      112 Central Ave, Winchester, KY 40391

      Last Sold Summary

      • 1% Above List Price
      • $183/SF
      • 1 Day On Market
      • Last Sold Price $220,000
      • Apr 23, 2025

      Last Listing Agent Nena Honaker Tom Goebel & Company

Showing Results 401 - 440, Page 11 of 18

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