Winchester, KY 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.

  

  Philip 'PJ' Elder

  Omega Real Estate Brokerage LLC

  110 White Conkwright Rd, Winchester, KY 40391
• Explore Winchester

• 

  

  

  /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
• 

  

  

  /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.

  

  Christa Joynt

  Keller Williams Commonwealth

  107 Hibiscus Ln, 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
• 

  

  /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

  

  Brenda Sipes

  WEICHERT REALTORS - ABG Properties

  186 Chardonnay Ct, 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
• 

  

  /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

  

  Christa Joynt

  Keller Williams Commonwealth

  10 Chickadee Ln, 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
• 

  

  /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

  

  Brenda Sipes

  WEICHERT REALTORS - ABG Properties

  30 Virginia Ave, 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
• 

  

  /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

  

  Dustin Pennington

  Keller Williams Legacy Group

  133 Bay Hill Dr, 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
• 

  

  /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,

  

  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
• 

  

  /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
• 

  

  /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

  

  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
• 

  

  /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
• 

  

  /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

  

  Christa Joynt

  Keller Williams Commonwealth

  2725 Goshen Rd, 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
• 

  

  /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
• 

  

  /46

  $749,900

  • 3 Beds
  • 2.5 Baths
  • 2,735 Sq Ft

  2180 Big Stoner Rd, Winchester, KY 40391

  Welcome to peaceful country living on 7.14 beautiful acres in Winchester! Built in 2022, this custom one-level home offers 3 bedrooms, 2.5 bathrooms, and 2,735 square feet of thoughtfully designed living space. The open floor plan features hardwood flooring, a spacious great room with a gas fireplace, and a stylish kitchen with a large island and ample cabinetry. The split-bedroom layout provides

  

  Ashley Barreto

  Indigo & Co

  2180 Big Stoner Rd, 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
• 

  

  /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