Winchester, KY Real Estate & Homes For Sale

122 homes

  • 3070 Goshen Rd, Winchester, KY 40391
    Use arrow keys to navigate
    NEW - 4 HRS AGO10 ACRES
    $379,900
    3bd
    2ba
    2,866 sqft (on 10 acres)
    3070 Goshen Rd,
    Winchester, KY 40391
    Keller Williams Legacy Group, Bluegrass REALTORS®
  • 704 W  Lexington Ave, Winchester, KY 40391
    Use arrow keys to navigate
    NEW - 11 HRS AGO
    The Agency, Bluegrass REALTORS®
  • 132 Gadwall Ln, Winchester, KY 40391
    Use arrow keys to navigate
    NEW - 14 HRS AGO0.61 ACRES
    $509,000
    3bd
    3ba
    2,511 sqft (on 0.61 acres)
    132 Gadwall Ln,
    Winchester, KY 40391
    Bridgewater Real Estate, Bluegrass REALTORS®
  • 105 Linden Ave, Winchester, KY 40391
    Use arrow keys to navigate
    NEW - 2 DAYS AGO
    $212,000
    3bd
    2ba
    1,496 sqft
    105 Linden Ave,
    Winchester, KY 40391
    The Agency, Bluegrass REALTORS®
  • 100 Dallas Aly, Winchester, KY 40391
    Use arrow keys to navigate
    Re/Max Creative Realty, Bluegrass REALTORS®
  • 1124 Ironworks Rd, Winchester, KY 40391
    Use arrow keys to navigate
    Coldwell Banker Mcmahan, Bluegrass REALTORS®
  • 302 W  Lexington Ave, Winchester, KY 40391
    Use arrow keys to navigate
    Rector Hayden Realtors, Bluegrass REALTORS®
  • 302 Briarwood Ln, Winchester, KY 40391
    Keller Williams Legacy Group, Bluegrass REALTORS®
  • 14 Cook Ave, Winchester, KY 40391
    $59,900
    3bd
    1ba
    1,261 sqft
    14 Cook Ave,
    Winchester, KY 40391
    Metro Max Realty, Bluegrass REALTORS®
  • 18 A St, Winchester, KY 40391
    NEW CONSTRUCTION
    $198,400
    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®
  • 885 Log Lick Rd, Winchester, KY 40391
    42.65 ACRES
    Re/Max Creative, Winchester, Bluegrass REALTORS®
  • 1060 L E Junction Rd, Winchester, KY 40391
    1.34 ACRES
    $195,000
    2bd
    1ba
    1,300 sqft (on 1.34 acres)
    1060 L E Junction Rd,
    Winchester, KY 40391
    Ensor Real Estate, LLC, Bluegrass REALTORS®
  • 12 Casa Landa Way, Winchester, KY 40391
    0.53 ACRES
    $379,900
    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®
  • 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®
  • 2380 Athens Boonesboro Rd, Winchester, KY 40391
    8.04 ACRES
    Keller Williams Legacy Group, Bluegrass REALTORS®
  • 2010 Athens Boonesboro Rd, Winchester, KY 40391
    8.03 ACRES
    Keller Williams Legacy Group, Bluegrass REALTORS®
  • 404 Corinne Ct, Winchester, KY 40391
    $292,000
    3bd
    3ba
    1,616 sqft
    404 Corinne Ct,
    Winchester, KY 40391
    Sandy Stuart Realty, Bluegrass REALTORS®
  • 124 Winterberry Cir, Winchester, KY 40391
    0.57 ACRES
    Christie's International Real Estate Bluegrass, Bluegrass REALTORS®
  • 1275 Old Log Lick Rd, Winchester, KY 40391
    202.61 ACRES
    $825,000
    3bd
    2ba
    1,392 sqft (on 202.61 acres)
    1275 Old Log Lick Rd,
    Winchester, KY 40391
    Bluegrass Properties Group, Bluegrass REALTORS®
  • 711 Terry Dr, Winchester, KY 40391
    $275,000
    3bd
    2ba
    2,110 sqft
    711 Terry Dr,
    Winchester, KY 40391
    Re/Max Creative, Winchester, Bluegrass REALTORS®
  • 4353 Old Boonesboro Rd, Winchester, KY 40391
    1.24 ACRES
    $445,900
    5bd
    3ba
    2,952 sqft (on 1.24 acres)
    4353 Old Boonesboro Rd,
    Winchester, KY 40391
    Kassie & Associates, Bluegrass REALTORS®
  • 3385 Colby Rd, Winchester, KY 40391
    2.77 ACRES
    Steven D Adams Real Estate Services, LLC, Bluegrass REALTORS®
  • 140 Westside Dr, Winchester, KY 40391
    Coldwell Banker Mcmahan, Bluegrass REALTORS®
  • 3327 Mina Station Rd, Winchester, KY 40391
    1.01 ACRES
    $225,000
    3bd
    2ba
    1,296 sqft (on 1.01 acres)
    3327 Mina Station Rd,
    Winchester, KY 40391
    Re/Max Creative, Winchester, Bluegrass REALTORS®
  • 308 Duclair Dr, Winchester, KY 40391
    0.41 ACRES
    Bridgewater Real Estate, Bluegrass REALTORS®
  • 121 Summerhill Way, Winchester, KY 40391
    Plum Tree Realty, Bluegrass REALTORS®
  • 330 Epperson Rd, Winchester, KY 40391
    10 ACRES
    Keller Williams Commonwealth, Bluegrass REALTORS®
  • 37 Lincoln St, Winchester, KY 40391
    Plum Tree Realty, Bluegrass REALTORS®
  • 580 McClure Rd, Winchester, KY 40391
    1.5 ACRES
    $435,000
    4bd
    2ba
    2,500 sqft (on 1.50 acres)
    580 McClure Rd,
    Winchester, KY 40391
    Keller Williams Commonwealth, Bluegrass REALTORS®
  • 410 Fairholme Way, Winchester, KY 40391
    0.4 ACRES
    Tom Goebel & Company, Bluegrass REALTORS®
  • 418 Fairholme Way, Winchester, KY 40391
    0.38 ACRES
    Tom Goebel & Company, Bluegrass REALTORS®
  • 416 Fairholme Way, Winchester, KY 40391
    0.38 ACRES
    Tom Goebel & Company, Bluegrass REALTORS®
  • 414 Fairholme Way, Winchester, KY 40391
    0.37 ACRES
    Tom Goebel & Company, Bluegrass REALTORS®
  • 1255 The Ridings Rd, Winchester, KY 40391
    5.12 ACRES
    $645,000
    5bd
    4ba
    3,594 sqft (on 5.12 acres)
    1255 The Ridings Rd,
    Winchester, KY 40391
    United Real Estate Bluegrass, 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 $225,560
MonthMedian home value
March 2023$208k
April 2023$209k
May 2023$211k
June 2023$213k
July 2023$215k
August 2023$217k
September 2023$218k
October 2023$220k
November 2023$222k
December 2023$223k
January 2024$224k
February 2024$226k
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 13 new listings and 122 homes for sale in Winchester.
Home SizeHome Value*
2 bedrooms (1 home)$141,052
3 bedrooms (36 homes)$221,862
4 bedrooms (12 homes)$295,818
*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. "
    0
    Flag
  • 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 "
    0
    Flag
  • 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 "
    8
    Flag
  • Joyce S.
    "Great neighborhood that looks out for each other and sits on the Golf Course. Very clean, quiet neighborhood"
    4
    Flag
  • Karen K.
    "Community yard sales, lots of children and the parents watch out for each other’s children. Schools are very good. "
    2
    Flag
  • Alishacorley23
    "downtown is kind of shady but I'm from here so I know alot of people. and its cute and historic thank you."
    4
    Flag
  • 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."
    0
    Flag
  • Awallace08
    "Quiet neighborhood close to schools and shopping. Low crime area, low traffic area, properties are kept cut and clean "
    0
    Flag
  • Barb H.
    "My neighborhood is an excellent place to call home. I always see people out walking their dogs. The neighbors are friendly. "
    0
    Flag
  • 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. "
    0
    Flag
  • 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."
    0
    Flag
  • Bridgetgwyn27
    "I travel over 25 miles a day to the next county. Can be busy especially during the 5’ o’clock hour. "
    1
    Flag
  • 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."
    1
    Flag
  • 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!!! "
    0
    Flag
  • 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. "
    0
    Flag
  • Barbarataulbee
    "They would love to live here cause people watch out for each other and their doggie. Dogs are very safe in our neighborhood. "
    0
    Flag
  • 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."
    0
    Flag
  • 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."
    4
    Flag
  • 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. "
    0
    Flag
  • 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!!"
    0
    Flag
  • Cristy J.
    "very safe and friendly area, no through traffic. walk to elementary and secondary school"
    0
    Flag
  • 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. "
    6
    Flag
  • 123qwe
    "This is a horribly run down area.No sidewalks,rough people,LOTS of loose viciuos dogs.Crime,drugs."
    15
    Flag
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.