Winchester, KY Real Estate & Homes For Sale

127 homes

  • 218 Ashton Oak Way, Winchester, KY 40391
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    NEW - 3 HRS AGO0.34 ACRES
    $374,900
    3bd
    2ba
    1,931 sqft (on 0.34 acres)
    218 Ashton Oak Way,
    Winchester, KY 40391
    Freedom Realty & Property Management, Bluegrass REALTORS®
  • 102 Kentucky St, Winchester, KY 40391
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    Ky Realty Co, Bluegrass REALTORS®
  • 142 Sunset Hts, Lexington, KY 40391
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    $249,000
    3bd
    2ba
    1,422 sqft
    142 Sunset Hts,
    Lexington, KY 40391
    Milton And Associates Real Estate, Bluegrass REALTORS®
  • 427 Jameson Way, Winchester, KY 40391
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    0.28 ACRES
    $268,500
    3bd
    2ba
    1,776 sqft (on 0.28 acres)
    427 Jameson Way,
    Winchester, KY 40391
    Keller Williams Commonwealth, Bluegrass REALTORS®
  • 511 Boone Ave, Winchester, KY 40391
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    2.6 ACRES
    $975,000
    4bd
    5ba
    4,698 sqft (on 2.60 acres)
    511 Boone Ave,
    Winchester, KY 40391
    Block + Lot Real Estate, Bluegrass REALTORS®
  • 127 Hibiscus Ln, Winchester, KY 40391
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    NEW CONSTRUCTION
    Freedom Realty & Property Management, Bluegrass REALTORS®
  • 1159 Cabin Creek Rd, Winchester, KY 40391
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    5.57 ACRES
    $469,000
    3bd
    3ba
    2,244 sqft (on 5.57 acres)
    1159 Cabin Creek Rd,
    Winchester, KY 40391
    Coldwell Banker Mcmahan, Bluegrass REALTORS®
  • 12 Denny Ave, Winchester, KY 40391
    $175,000
    3bd
    2ba
    1,093 sqft
    12 Denny Ave,
    Winchester, KY 40391
    Re/Max Creative, Winchester, Bluegrass REALTORS®
  • 610 Old Ruckerville Rd, Winchester, KY 40391
    5.66 ACRES
    $399,900
    2bd
    3ba
    1,800 sqft (on 5.66 acres)
    610 Old Ruckerville Rd,
    Winchester, KY 40391
    Tom Goebel & Company, Bluegrass REALTORS®
  • 42 Mockingbird Valley Rd, Winchester, KY 40391
    0.33 ACRES
    $499,900
    3bd
    3ba
    3,148 sqft (on 0.33 acres)
    42 Mockingbird Valley Rd,
    Winchester, KY 40391
    Freedom Realty & Property Management, Bluegrass REALTORS®
  • 737 Williamsburg Dr, Winchester, KY 40391
    Dream Maker Realty, LLC, Bluegrass REALTORS®
  • 129 Kentucky St, Winchester, KY 40391
    Distinctive Living, Bluegrass REALTORS®
  • 210 Hood Ave, Winchester, KY 40391
    1.03 ACRES
    Dixon Properties, Bluegrass REALTORS®
  • 1905 McClure Rd, Winchester, KY 40391
    4.07 ACRES
    $349,000
    6bd
    2ba
    3,820 sqft (on 4.07 acres)
    1905 McClure Rd,
    Winchester, KY 40391
    Freedom Realty & Property Management, Bluegrass REALTORS®
  • 225 Connie Ln, Winchester, KY 40391
    Dixon Properties, Bluegrass REALTORS®
  • 115 Dixon Way, Winchester, KY 40391
    4.15 ACRES
    Dixon Properties, Bluegrass REALTORS®
  • 104 Teal Ln, Winchester, KY 40391
    0.34 ACRES
    $559,900
    5bd
    4ba
    4,456 sqft (on 0.34 acres)
    104 Teal Ln,
    Winchester, KY 40391
    Re/Max Elite Realty, Bluegrass REALTORS®
  • 31 Bonnie Brook Ln, Winchester, KY 40391
    0.61 ACRES
    $650,000
    5bd
    4ba
    4,091 sqft (on 0.61 acres)
    31 Bonnie Brook Ln,
    Winchester, KY 40391
    Coldwell Banker Mcmahan, Bluegrass REALTORS®
  • 27 Fontaine Blvd, Winchester, KY 40391
    0.38 ACRES
    $379,900
    4bd
    4ba
    2,610 sqft (on 0.38 acres)
    27 Fontaine Blvd,
    Winchester, KY 40391
    Kentucky Realty Group, LLC, Bluegrass REALTORS®
  • 1410 Dry Fork Creek Rd, Winchester, KY 40391
    92.31 ACRES
    Keller Williams Commonwealth, Bluegrass REALTORS®
  • 1995 Gay Evans Rd, Winchester, KY 40391
    8 ACRES
    $799,000
    4bd
    4ba
    3,272 sqft (on 8 acres)
    1995 Gay Evans Rd,
    Winchester, KY 40391
    Lifstyl Real Estate, Bluegrass REALTORS®
  • 335 S  Main St, Winchester, KY 40391
    $289,000
    4bd
    2ba
    1,968 sqft
    335 S Main St,
    Winchester, KY 40391
    Keller Williams Commonwealth, Bluegrass REALTORS®
  • 623 Ecton Rd, Winchester, KY 40391
    NEW CONSTRUCTION
    $324,900
    2bd
    2ba
    1,523 sqft
    623 Ecton Rd,
    Winchester, KY 40391
    The Agency, Bluegrass REALTORS®
  • 130 E  Broadway St, Winchester, KY 40391
    Team Pannell Real Estate, Bluegrass REALTORS®
  • 25 Hays St, Winchester, KY 40391
    0.26 ACRES
    $224,000
    5bd
    4ba
    2,830 sqft (on 0.26 acres)
    25 Hays St,
    Winchester, KY 40391
    Team Pannell Real Estate, Bluegrass REALTORS®
  • 242 W  Lexington Ave, Winchester, KY 40391
    Thwaites Realtors LLC, Bluegrass REALTORS®
  • 20 Edgewood Dr, Winchester, KY 40391
    0.47 ACRES
    $385,000
    3bd
    3ba
    2,366 sqft (on 0.47 acres)
    20 Edgewood Dr,
    Winchester, KY 40391
    Lawson Real Estate, Inc, Bluegrass REALTORS®
  • 108 Dixon Way, Winchester, KY 40391
    $269,900
    3bd
    3ba
    1,377 sqft
    108 Dixon Way,
    Winchester, KY 40391
    Dixon Properties, Bluegrass REALTORS®
  • 3622 Stamper Dr, Winchester, KY 40391
    0.26 ACRES
    $425,000
    3bd
    3ba
    2,821 sqft (on 0.26 acres)
    3622 Stamper Dr,
    Winchester, KY 40391
    Dream Maker Realty, LLC, Bluegrass REALTORS®
  • 327 Maryland Ave, Winchester, KY 40391
    Bluegrass Property Exchange, Bluegrass REALTORS®
  • 18 A St, Winchester, KY 40391
    NEW CONSTRUCTION
    $189,900
    3bd
    1ba
    1,200 sqft
    18 A St,
    Winchester, KY 40391
    Tom Goebel & Company, Bluegrass REALTORS®
  • 129 Buckner St, Winchester, KY 40391
    $205,000
    3bd
    2ba
    1,328 sqft
    129 Buckner St,
    Winchester, KY 40391
    Bluegrass Sotheby's International Realty, Bluegrass REALTORS®
  • 12 Casa Landa Way, Winchester, KY 40391
    0.53 ACRES
    $369,900
    3bd
    2ba
    2,120 sqft (on 0.53 acres)
    12 Casa Landa Way,
    Winchester, KY 40391
    Marshall Lane Real Estate - Lexington, Bluegrass REALTORS®
  • 118 Spruce Ct, Winchester, KY 40391
    $210,000
    3bd
    2ba
    1,798 sqft
    118 Spruce Ct,
    Winchester, KY 40391
    Christie's International Real Estate Bluegrass, Bluegrass REALTORS®
  • 2020 Two Mile Rd, Winchester, KY 40391
    3.99 ACRES
    $289,900
    3bd
    2ba
    1,320 sqft (on 3.99 acres)
    2020 Two Mile Rd,
    Winchester, KY 40391
    Dream Maker Realty, LLC, Bluegrass REALTORS®
  • 3999 Bybee Rd, Winchester, KY 40391
    4.14 ACRES
    Rector Hayden Realtors, Bluegrass REALTORS®
  • 301 Hanover Dr, Winchester, KY 40391
    0.26 ACRES
    $280,000
    3bd
    2ba
    1,540 sqft (on 0.26 acres)
    301 Hanover Dr,
    Winchester, KY 40391
    Dream Maker Realty, LLC, Bluegrass REALTORS®
  • 2514 Athens Boonesboro Rd, Winchester, KY 40391
    4 ACRES
    Keller Williams Legacy Group, Bluegrass REALTORS®
  • 2110 Athens Boonesboro Rd, Winchester, KY 40391
    8.09 ACRES
    Keller Williams Legacy Group, Bluegrass REALTORS®
  • 2416 Athens Boonesboro Rd, Winchester, KY 40391
    8 ACRES
    Keller Williams Legacy Group, Bluegrass REALTORS®

Winchester, KY Real Estate Trends

Learn about the Winchester, KY housing market through trends and averages.

Affordability of Living in Winchester, KY

The median home value is $232,012
MonthMedian home value
April 2023$213k
May 2023$215k
June 2023$217k
July 2023$219k
August 2023$221k
September 2023$223k
October 2023$224k
November 2023$226k
December 2023$227k
January 2024$228k
February 2024$230k
March 2024$232k
View as a graph
Trends and affordability stats are provided by third party data sources.

Average Home Value in Winchester, KY, by Home Size

Currently, there are 14 new listings and 127 homes for sale in Winchester.
Home SizeHome Value*
2 bedrooms (5 homes)$146,466
3 bedrooms (35 homes)$227,795
4 bedrooms (14 homes)$303,742
*Home value over the past month

What Locals Say about Winchester

  • Ccharles
    "Where I live, there are lots of space for dogs to roam and run to get their energy out. Coyotes do inhabit the area so just be mindful when your dogs are outside. "
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  • Clarissa R. C.
    "Beer cheese festival is the best and The brewery is awesome. Lumas is cool too. It’s a great place to live and feel safe "
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  • Joyce S.
    "Great neighborhood for walking dogs. Plenty of room to walk and areas are easy to pick up waste. Neighbors are friendly for people and pets "
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  • Joyce S.
    "Great neighborhood that looks out for each other and sits on the Golf Course. Very clean, quiet neighborhood"
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  • Karen K.
    "Community yard sales, lots of children and the parents watch out for each other’s children. Schools are very good. "
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  • Alishacorley23
    "downtown is kind of shady but I'm from here so I know alot of people. and its cute and historic thank you."
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  • Garrison9908
    "We Have a neighborhood association with a dedicated group of families that live in the area and are personally involved and educated on issues surrounding them."
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  • Awallace08
    "Quiet neighborhood close to schools and shopping. Low crime area, low traffic area, properties are kept cut and clean "
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  • Barb H.
    "My neighborhood is an excellent place to call home. I always see people out walking their dogs. The neighbors are friendly. "
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  • Garrison9908
    "My neighborhood is a neighborhood of avid boaters and fisherman who like to live near the Kentucky River. There are a few clubs that people gather together for as well as a couple of local restaurants that are hang outs. "
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  • Garrison9908
    "I’ve lived in this neighborhood for over 30 years. It is a close knit community with individuals residing here that love nature, love the Kentucky River, and all things outdoors."
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  • Bridgetgwyn27
    "I travel over 25 miles a day to the next county. Can be busy especially during the 5’ o’clock hour. "
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  • StephanieD
    "This is a beautiful neighborhood. On the forth of July you can sit on your deck or porch and watch the most spectacular fire work shows. It is an easy picturesque drive to Hamburg or Richmond and a quick five minute jaunt if you need a gallon of milk. Everybody I met is polite and courteous and it is very dog friendly- I once had a neighbor on another street put water out for the dogs walking by his house to drink. I wouldn't want to live anywhere else."
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  • Barbara.smith13
    "There’s a pit bull that lives on east broadway that has tried to kill my dog on more than 1 occasion. I called the cops the first They did Nothing bout the attack. Put the Pitt back in his lot hooked him bk up to the car chain he was attached too!!! "
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  • Barbarataulbee
    "I live here. The neighbors a great. It’s also very dog and cat friendly. Every body helps each other that lives here. They also watch out for each other. There’s never any crime in out neighborhood. "
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  • Barbarataulbee
    "They would love to live here cause people watch out for each other and their doggie. Dogs are very safe in our neighborhood. "
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  • Shelby G.
    "lots of street dances, 3 festivals, many community events put on by the local churches. Christmas and homecoming parades are themed, downtown does a "trick or treat on main" which is also where the street dances and beer cheese festival are."
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  • Townsend m.
    "you will see dogs and their owners walking all the time in colonial park. it is a very quiet neighborhood. everyone is very nice and sweet all the kids do fundraisers for school and everyone participates."
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  • Dana B.
    "Some areas are great for walking or biking but a car is needed in most areas. The traffic and commute are generally worry free. "
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  • Heatherbcass
    "I have lived in my current residence for 3 years and my neighbors are like family and we all have a babysitter anytime we need one!!"
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  • Cristy J.
    "very safe and friendly area, no through traffic. walk to elementary and secondary school"
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  • katonaboat47
    "Lovely older homes, big shade trees, nice sidewalks, friendly, old-fashioned atmosphere. Lots of grandparents and empty nesters in this neighborhood. Less than 2 blocks from the country club with golf, tennis and swimming. "
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  • 123qwe
    "This is a horribly run down area.No sidewalks,rough people,LOTS of loose viciuos dogs.Crime,drugs."
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IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.
The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed.