16,242

Winchester, KY Homes

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  • /74

    $385,000

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft

    2725 Goshen Rd, Winchester, KY 40391

    Welcome to this one-owner home offering the perfect combination of space, thoughtful updates, and country living! Built in 1996 and situated on 1.67 beautiful acres, this well-maintained 3-bedroom, 2-bath home features 1,344 square feet of comfortable living space with numerous improvements already completed for its next owner. Inside, you'll find updated interior paint, durable LifeProof

    Agent Photo

    Christa Joynt

    Keller Williams Commonwealth

    2725 Goshen Rd, Winchester, KY 40391
  • /28

    Call for Price

    • 1 - 3 Beds

    300 C G Stephenson Dr, Winchester, KY 40391

    This community is open by appt only. Office hours are 9am to 12pm and 1pm to 4pm. Please call to schedule your appt!Cambridge Square is a community with beautifully maintained grounds, offering one, two and three bedroom apartment homes with some one bedroom homes reserved for the elderly/dis-abled, all rent based on income. We are located in quiet Winchester, Kentucky, with easy

    Cambridge Square Apartments - Income Based

    300 C G Stephenson Dr, Winchester, KY 40391
  • /8

    $15,000

    Sold Dec 30, 2025

    61 Melbourne St, Winchester, KY 40391

    • Land
    • 4,356 Sq Ft
    • $150,000 per Acre

    Last Sold Summary

    • 40% Below List Price
    • 57 Days On Market

    Current Estimated Value $108,274

    Last Listing Agent Brian Lewis Guide Realty, Inc.

    61 Melbourne St, Winchester, KY 40391
    • /53

      Est $904,192

      Not Listed For Sale

      511 Boone Ave, Winchester, KY 40391

      • 4 Beds
      • 4.5 Baths
      • 4,698 Sq Ft
      • Built 1885
      511 Boone Ave, Winchester, KY 40391

      Last Sold Summary

      • 318 Days On Market

      Last Listing Agent Greg Leveridge Block + Lot Homes

  • /18

    $515,000

    $41K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 3,102 Sq Ft

    110 White Conkwright Rd, Winchester, KY 40391

    Brick ranch with 3 upstairs bedrooms and 2 bedrooms in your mother in law suite and full finished basement, complete with kitchen. 2 gazebos with one attached to walk out porch over looking almost 3 acres of beautiful land. Attached 2 car garage and detached 2 car garage. Barn/workshop included, along with another metal building for storage.

    Agent Photo

    Philip 'PJ' Elder

    Omega Real Estate Brokerage LLC

    110 White Conkwright Rd, Winchester, KY 40391
  • /35

    Starting at $800 Per Month

    • 1 - 3 Beds

    260 Oxford Dr, Winchester, KY 40391

    The Summit located in Winchester; KY is just minutes away from major employers. We are just a short drive from Lexington, KY. Come see our pet friendly community with lots of green space. We have spacious one-, two-, and three-bedroom apartment homes with caring on-site management. Our homes feature walk-in closets, new Laminate Vinyl Plank Flooring, fully equipped kitchens, washer/dryer

    Summit Apartments

    260 Oxford Dr, Winchester, KY 40391
  • /20

    $189,500

    Sold Dec 18, 2025

    13015 Irvine Rd, Winchester, KY 40391

    Last Sold Summary

    • 17% Below List Price
    • 134 Days On Market

    Last Listing Agent Mendel Tipton Natural Bridge Realty

    13015 Irvine Rd, Winchester, KY 40391
    • /32

      Est $336,222

      Not Listed For Sale

      275 Cross Brook Ct, Winchester, KY 40391

      • 3 Beds
      • 2.5 Baths
      • 2,111 Sq Ft
      • Built 1998
      275 Cross Brook Ct, Winchester, KY 40391

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Amanda Stewart Stewart & Co Realty LLC

  • /64

    $399,000

    $21K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,978 Sq Ft

    107 Hibiscus Ln, Winchester, KY 40391

    Welcome to 107 Hibiscus, where thoughtful updates, quality craftsmanship, and exceptional maintenance come together in this spacious 4-bedroom, 2.5-bath home. Offering a versatile floor plan with generous living spaces, this move-in-ready property has benefited from approximately nearly $70,000 in improvements over the past several years, providing peace of mind and modern finishes throughout.

    Agent Photo

    Christa Joynt

    Keller Williams Commonwealth

    107 Hibiscus Ln, Winchester, KY 40391
  • /28

    Call for Price

    • 1 - 3 Beds

    900 Westwood Dr, Winchester, KY 40391

    Pick up your application for our WAIT LIST at the office door! Westwood is a charming property in a great location in Winchester, Kentucky with rents based on income. Spacious one, two and three bedroom apartments for rent, each featuring a fully equipped kitchen, your choice of a patio or balcony, and they are wired for cable. Fun in the sun is just a outside your door at our playground, or

    Westwood Apartments - Income Based

    900 Westwood Dr, Winchester, KY 40391
  • /51

    $750,000

    Sold May 21, 2026

    1783 Gay Evans Rd, Winchester, KY 40391

    • 5 Beds
    • 3.5 Baths
    • 2,904 Sq Ft
    • Built 1998

    Last Sold Summary

    • 6% Below List Price
    • $258/SF
    • 135 Days On Market

    Current Estimated Value $731,156

    Last Listing Agent Lucy Martin Jenkins United Real Estate Bluegrass

    1783 Gay Evans Rd, Winchester, KY 40391
    • /16

      Est $258,021

      Not Listed For Sale

      13385 Ironworks Rd, Winchester, KY 40391

      • 3 Beds
      • 2 Baths
      • 1,350 Sq Ft
      • Built 1980
      13385 Ironworks Rd, Winchester, KY 40391

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Joshua Davis The Agency

  • /84

    $675,000

    $124K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 4,928 Sq Ft

    186 Chardonnay Ct, Winchester, KY 40391

    Fontaine Estates, a great place to call home. This spacious 4 bedroom 3 bath property offers an abundance of storage,, including charming window seats. Enjoy the convenience of an oversized driveway and garage, along with a beautifully designed outdoor setting, feauring a fire pit and a dedicated entertainment space. The thoughtfully planned, custom designed landscaping enhances the home's curb

    Agent Photo

    Brenda Sipes

    WEICHERT REALTORS - ABG Properties

    186 Chardonnay Ct, Winchester, KY 40391
  • /2

    Starting at $814 Per Month

    • Studio

    27 E Washington St, Winchester, KY 40391

    *One Month Free Rent!* All Utilities Included! Nice Studio Apt Near Downtown Winchester!Marketing DescriptionStudio Apartment Available at Studio 29 Apartments, Winchester, KY! One Bath; Only 5 Minutes from Downtown! Off-Street Parking, Small Pets Ok; All Utilities Included! Kitchen includes a Stove, Refrigerator, and Microwave; Non-smoking.Conveniently located near Shopping, Grocery

    Studio 28

    27 E Washington St, Winchester, KY 40391
  • /41

    $302,500

    Sold Jan 05, 2026

    202 Dubuy Dr, Winchester, KY 40391

    • 3 Beds
    • 2.5 Baths
    • 1,800 Sq Ft
    • Built 2022

    Last Sold Summary

    • 1% Below List Price
    • $168/SF
    • 5 Days On Market

    Current Estimated Value $307,636

    Last Listing Agent Jonne Ursos Keller Williams Bluegrass Realty

    202 Dubuy Dr, Winchester, KY 40391
    • /24

      Est $226,961

      Not Listed For Sale

      13365 Ironworks Rd, Winchester, KY 40391

      • 3 Beds
      • 1 Bath
      • 1,420 Sq Ft
      • Built 1973
      13365 Ironworks Rd, Winchester, KY 40391

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Joshua Davis The Agency

  • /55

    $239,900

    $10K PRICE DROP Pending
    • 3 Beds
    • 1 Bath
    • 1,204 Sq Ft

    10 Chickadee Ln, Winchester, KY 40391

    Welcome to 10 Chickadee Lane, Winchester, KY—a beautifully updated 3-bedroom, 1-bath ranch offering the perfect combination of modern upgrades, timeless character, and an unbeatable location. If you're searching for a move-in ready home in Winchester, Kentucky, this one deserves a spot at the top of your list. Extensively renovated in 2020, this home provides peace of mind with major improvements

    Agent Photo

    Christa Joynt

    Keller Williams Commonwealth

    10 Chickadee Ln, Winchester, KY 40391
  • /3

    Starting at $1,049 Per Month

    • 2 - 3 Beds

    510 College St, Winchester, KY 40391

    Lovely 2 Bedroom and One Bath Apartment at the Lofts of Winchester, located at 508 College Street, Winchester, KY! Near Downtown, Shopping, Restaurants, Hwy 64 and Hwy 60. Off-street Parking; Small Pets Ok! Beautiful Updated Flooring and Stainless Steel Appliances. Kitchen includes Stove and Refrigerator. Central Heat & AC.Local Schools are: Willis H. Justice Elementary; Robert D.

    The Lofts at Winchester

    510 College St, Winchester, KY 40391
  • /31

    $88,500

    Sold Aug 08, 2025

    15 Sycamore St, Winchester, KY 40391

    • 3 Beds
    • 1 Bath
    • 1,144 Sq Ft
    • Built 1945

    Last Sold Summary

    • 12% Below List Price
    • $77/SF
    • 28 Days On Market

    Current Estimated Value $115,881

    Last Listing Agent Rony Jo Ballou Power House Realty

    15 Sycamore St, Winchester, KY 40391
    • /70

      Est $315,852

      Not Listed For Sale

      705 Oil Springs Rd, Winchester, KY 40391

      • 4 Beds
      • 2 Baths
      • 1,572 Sq Ft
      • Built 1979
      705 Oil Springs Rd, Winchester, KY 40391

      Last Sold Summary

      • 35 Days On Market

      Last Listing Agent Victoria Byrd HomeFirst Real Estate

  • /46

    $229,000

    $18K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,050 Sq Ft

    30 Virginia Ave, Winchester, KY 40391

    Welcome to a well maintained 3 bedroom 1 full bath home that has been lovingly cared for by only two owners since 1962. Recent updates include new flooring and completed repairs, makiing this property ready for a new owner, while preserving its timeless character. Beautiful hardwood floors add warmth and charm throughout the home. Enjoy relaxing or entertaining on the comfortable spacious patio

    Agent Photo

    Brenda Sipes

    WEICHERT REALTORS - ABG Properties

    30 Virginia Ave, Winchester, KY 40391
  • /41

    $2,595 Per Month

    • 4 Beds
    • 3 Baths
    • 2,160 Sq Ft
    • House for Rent

    721 Wayland Dr, Winchester, KY 40391

    Welcome home to the perfect blend of peaceful country living and modern convenience. Located in Winchester, Kentucky, this beautifully remodeled 4-bedroom, 3 full-bath home offers an easy commute to Hamburg and all the shopping, dining, and entertainment Lexington has to offer. Step inside to discover a stunning kitchen designed to be the heart of the home—perfect for gathering with family and

    S Ann Wesley Assurance Realty & Property Management

    721 Wayland Dr, Winchester, KY 40391
  • /30

    $190,000

    Sold Mar 06, 2026

    2721 Pretty Run Rd, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 1,456 Sq Ft
    • Built 2000

    Last Sold Summary

    • 37% Below List Price
    • $130/SF
    • 12 Days On Market

    Current Estimated Value $199,336

    Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

    2721 Pretty Run Rd, Winchester, KY 40391
    • /44

      Est $462,121

      Not Listed For Sale

      1927 Kiddville Rd, Winchester, KY 40391

      • 5 Beds
      • 4 Baths
      • 2,056 Sq Ft
      • Built 2001
      1927 Kiddville Rd, Winchester, KY 40391

      Last Sold Summary

      • 22 Days On Market

      Last Listing Agent Megan McCoy Keller Williams Legacy Group

  • /24

    $280,000

    • 4 Beds
    • 3.5 Baths
    • 3,276 Sq Ft

    133 Bay Hill Dr, Winchester, KY 40391

    Welcome to 133 Bay Hill Drive in Winchester, Kentucky — a spacious and beautifully maintained home offering over 3,200 square feet of living space in one of the area's desirable subdivisions. Conveniently located just minutes from town and close to local factories and major employers, this property offers the perfect blend of comfort, convenience, and neighborhood living. Inside, you'll find

    Agent Photo

    Dustin Pennington

    Keller Williams Legacy Group

    133 Bay Hill Dr, Winchester, KY 40391
  • /6

    $1,145 Per Month

    • 1 Bed
    • 1 Bath
    • 700 Sq Ft
    • Condo for Rent

    1028 W Lexington Ave Unit 4, Winchester, KY 40391

    Welcome to 1028 W Lexington Ave, a cozy and well-maintained 1-bedroom, 1-bathroom apartment offering comfortable and affordable living in the heart of Winchester, KY. With a spacious living area, a functional kitchen, and a thoughtfully designed layout, this home is perfect for students, working professionals, or anyone looking to downsize.Property Features:1 Bedroom1 Full

    1028 W Lexington Ave Unit 4, Winchester, KY 40391
  • /35

    $308,000

    Sold Oct 03, 2025

    329 Hanover Dr, Winchester, KY 40391

    • 3 Beds
    • 2.5 Baths
    • 1,903 Sq Ft
    • Built 2003

    Last Sold Summary

    • 3% Below List Price
    • $162/SF
    • 5 Days On Market

    Current Estimated Value $322,800

    Last Listing Agent Bradley Warford Century 21 Pinnacle

    329 Hanover Dr, Winchester, KY 40391
    • /47

      Est $446,317

      Not Listed For Sale

      372 Arrowhead Ln, Winchester, KY 40391

      • 4 Beds
      • 3 Baths
      • 2,744 Sq Ft
      • Built 2001
      372 Arrowhead Ln, Winchester, KY 40391

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Lori Tolson Lifstyl Real Estate

  • /31

    $315,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,512 Sq Ft

    4305 Old Boonesboro Rd, Winchester, KY 40391

    Enjoy peaceful country living on this beautiful 2+ acre property featuring a nearly new manufactured home and a spacious barn. Surrounded by scenic countryside views, this property offers plenty of privacy, comfort, and room to enjoy the outdoors. The well-kept home provides a cozy place to relax, while the large barn and open space give you plenty of options for storage, hobbies, gardening,

    Agent Photo

    Brenda Sipes

    WEICHERT REALTORS - ABG Properties

    4305 Old Boonesboro Rd, Winchester, KY 40391
  • /2

    $1,700 Per Month

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft
    • Condo for Rent

    135 Winn Ave Unit A, Winchester, KY 40391

    Welcome to this beautifully renovated 3-bedroom, 2-bathroom home, offering the perfect combination of modern style and everyday comfort. The bright and spacious living area flows seamlessly into a stylish, updated kitchen, creating an inviting space for relaxing or entertaining. Thoughtfully designed with contemporary finishes and a functional layout, this move-in-ready home is ideal for

    135 Winn Ave Unit A, Winchester, KY 40391
  • /81

    $599,500

    Sold Aug 18, 2025

    2615 Crowe Ridge Rd, Winchester, KY 40391

    • 3 Beds
    • 2 Baths
    • 2,222 Sq Ft
    • Built 2018

    Last Sold Summary

    • $270/SF
    • 1 Day On Market

    Current Estimated Value $579,068

    Last Listing Agent ROBIN TRIMBLE HomeFirst Real Estate

    2615 Crowe Ridge Rd, Winchester, KY 40391
    • /112

      Est $786,112

      Not Listed For Sale

      703 Kiddville Rd, Winchester, KY 40391

      • 3 Beds
      • 3 Baths
      • 2,311 Sq Ft
      • Built 1980
      703 Kiddville Rd, Winchester, KY 40391

      Last Sold Summary

      • 276 Days On Market

      Last Listing Agent Tyson Walters Kassie & Associates

  • /64

    $420,000

    • 3 Beds
    • 2 Baths
    • 2,027 Sq Ft

    187 Hawthorne Dr, Winchester, KY 40391

    Welcome to 187 Hawthorne Drive, a beautifully maintained brick home in one of Winchester's most sought-after neighborhoods. Offering convenient one-level living, this 3-bedroom, 2-bath home features an inviting open floor plan that's perfect for everyday living and entertaining. The spacious living room is anchored by a cozy natural gas fireplace with gas logs, creating a warm and welcoming

    Agent Photo

    Christa Joynt

    Keller Williams Commonwealth

    187 Hawthorne Dr, Winchester, KY 40391
  • /2

    $1,300 Per Month

    • 3 Beds
    • 1 Bath
    • House for Rent

    101 E Lexington Ave, Winchester, KY 40391

    Make yourself at home in this charming 2-bedroom, 1-bathroom house, offering a spacious yet practical layout designed for comfortable everyday living. With bright living spaces, a functional kitchen, and two well-sized bedrooms, this home is ideal for small families, roommates, or anyone looking for extra space.This well-maintained home provides a welcoming atmosphere and the convenience

    101 E Lexington Ave, Winchester, KY 40391
  • /62

    $431,000

    Sold May 12, 2026

    2 Stoney Brook Dr, Winchester, KY 40391

    • 3 Beds
    • 3.5 Baths
    • 3,633 Sq Ft
    • Built 1983

    Last Sold Summary

    • 1% Below List Price
    • $119/SF
    • 1 Day On Market

    Current Estimated Value $433,148

    Last Listing Agent Kelli Hunt Berkshire Hathaway HomeServices Foster Realtors

    2 Stoney Brook Dr, Winchester, KY 40391
    • /43

      Est $410,459

      Not Listed For Sale

      700 Vienna Rd, Winchester, KY 40391

      • 3 Beds
      • 2 Baths
      • 1,826 Sq Ft
      • Built 2004
      700 Vienna Rd, Winchester, KY 40391

      Last Sold Summary

      • 18 Days On Market

      Last Listing Agent Sheridan Sims Keller Williams Commonwealth

  • /49

    $247,500

    $7K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,533 Sq Ft

    377 Crescent Ave, Winchester, KY 40391

    "Motivated sellers—bring your offers!" Step into this charming 3-bedroom, 2-bath home that's full of character and timeless appeal. From the beautiful hardwood floors to the inviting living spaces, this older home offers warmth and personality you simply don't find in newer construction. The spacious living room provides plenty of room to relax or entertain, while the separate dining room is

    Agent Photo

    Bill VanWinkle

    Joyce Marcum Realty

    377 Crescent Ave, Winchester, KY 40391
  • /3

    $1,550 Per Month

    • 2 Beds
    • 1 Bath
    • Condo for Rent

    202 S Maple St Unit C, Winchester, KY 40391

    Bright and comfortable 2-bedroom, 1-bathroom upstairs unit with all bills paid! Conveniently located at the corner of Hickman and Maple, directly across from Walgreens and Speedway gas station.Move-In Special:Free application50% off on your first month’s rent if you apply within 24 hourSecurity Deposit: $1,550.00Contact us today to schedule a showing or

    202 S Maple St Unit C, Winchester, KY 40391
  • /21

    $175,000

    Sold Nov 18, 2025

    612 Boone Ave, Winchester, KY 40391

    • 2 Beds
    • 2 Baths
    • 1,262 Sq Ft
    • Built 1958

    Last Sold Summary

    • 12% Below List Price
    • $139/SF
    • 13 Days On Market

    Current Estimated Value $182,810

    Last Listing Agent Garnett Davis Tom Goebel & Company

    612 Boone Ave, Winchester, KY 40391
    • /96

      Est $480,530

      Not Listed For Sale

      2430 Log Lick Rd, Winchester, KY 40391

      • 5 Beds
      • 3 Baths
      • 2,700 Sq Ft
      • Built 1938
      2430 Log Lick Rd, Winchester, KY 40391

      Last Sold Summary

      • 184 Days On Market

      Last Listing Agent E Anthony Phillips RE/MAX Creative Realty

Showing Results 1 - 40, Page 1 of 18

Home Price Trends

Median Sale Price
$265,000
Median Single Family Sale Price
$270,000
Median Townhouse Sale Price
$192,000
Median 2 Bedroom Sale Price
$167,500
Median 1 Bedroom Sale Price
$107,450
Average Price Per Sq Ft
$161
Number of Homes for Sale
79
Last 12 months Home Sales
309
Months of Supply
3.10
Median List Price
$275,000
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
10%
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