Homes in ZIP Code 40391

• 

  

  

  /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
• 

  

  

  /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
• 

  

  

  /34

  Est $355,843

  Not Listed For Sale

  3560 Wades Mill Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,305 Sq Ft
  • Built 1950

  3560 Wades Mill Rd, Winchester, KY 40391

  Last Sold Summary

  • 37 Days On Market

  Last Listing Agent Sarah MacHarg Kentucky Land and Home
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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

  

  Christa Joynt

  Keller Williams Commonwealth

  2725 Goshen 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
• 

  

  /12

  Est $159,504

  Not Listed For Sale

  406 W Washington St, Winchester, KY 40391

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

  406 W Washington St, Winchester, KY 40391

  Last Sold Summary

  • 19 Days On Market

  Last Listing Agent Jack Rookard Rookard Real Estate Consultants
• 

  

  /18

  $490,000

  $66K 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
• 

  

  /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 $740,996

  Last Listing Agent Lucy Martin Jenkins United Real Estate Bluegrass

  1783 Gay Evans Rd, Winchester, KY 40391
• 

  

  /41

  Est $258,378

  Not Listed For Sale

  3588 Stamper Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,530 Sq Ft
  • Built 1987

  3588 Stamper Dr, Winchester, KY 40391

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Zach Johnson The Brokerage
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  /64

  $379,000

  $41K 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
• 

  

  /6

  $1,300

  Total Monthly Price

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • House for Rent

  112 Old Bottom Rd, Winchester, KY 40391

  Great location! 3 bed 1 bath updated home with a huge backyard. Tenants pays water/sewer, electric and gas. Small dog accepted with a $300 pet fee and $25/month, Dog breed restrictions, Cats are not permitted.

  112 Old Bottom Rd, 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 $308,415

  Last Listing Agent Jonne Ursos Keller Williams Bluegrass Realty

  202 Dubuy Dr, Winchester, KY 40391
• 

  

  /19

  Est $225,324

  Not Listed For Sale

  521 Hidden Hills Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,335 Sq Ft
  • Built 2003

  521 Hidden Hills Way, Winchester, KY 40391

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Cathy Cornett-Wilson Rector Hayden Realtors
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  /84

  $649,000

  $150K 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
• 

  

  /11

  $1,295

  Total Monthly Price

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

  433 Country Club Dr, Winchester, KY 40391

  Yes, it is available. A application must be filled out and accepted prior to tours. Spacious clean townhome with a huge private backyard. 1 year lease. Convenient location. 1 small dog permitted. $350 pet fee. Dog breed restrictions apply.

  433 Country Club 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 $204,370

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

  2721 Pretty Run Rd, Winchester, KY 40391
• 

  

  /14

  Not Listed For Sale

  9711 Ironworks Rd, Winchester, KY 40391

  9711 Ironworks Rd, Winchester, KY 40391

  Last Sold Summary

  • 19 Days On Market

  Last Listing Agent Jessica Maloney Denniston Realty
• 

  

  /46

  $229,000

  $18K PRICE DROP Pending

  • 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
• 

  

  /29

  $1,995

  Total Monthly Price

  • 3 Beds
  • 2.5 Baths
  • 1,935 Sq Ft
  • House for Rent

  203 Inverness Ln, Winchester, KY 40391

  Spacious 3 Bedroom/2.5 Bath home for rent in one of the most sought after areas of Winchester!This beautiful home includes nearly 2,000 sq/ft of living space, real hardwood floors on the main level, a large kitchen, designated laundry room, oversized bedrooms, large master closet, backyard with a firepit, and a large 2 car garage!-Available 11/01/2026-Price does not include

  203 Inverness Ln, Winchester, KY 40391
• 

  

  /49

  $459,000

  Sold Aug 19, 2026

  105 Monet Blvd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 3,296 Sq Ft
  • Built 1995

  Last Sold Summary

  • 2% Below List Price
  • $139/SF
  • 27 Days On Market

  Current Estimated Value $458,737

  Last Listing Agent Kristey Wood Keller Williams Legacy Group

  105 Monet Blvd, Winchester, KY 40391
• 

  

  /47

  Est $380,111

  Not Listed For Sale

  714 Concord Ave, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,750 Sq Ft
  • Built 2017

  714 Concord Ave, Winchester, KY 40391

  Last Sold Summary

  • 23 Days On Market

  Last Listing Agent Josh Wood Freedom Realty & Property Management
• 

  

  /31

  $275,000

  $40K PRICE DROP

  • 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
• 

  

  /47

  $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
• 

  

  /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 $324,148

  Last Listing Agent Bradley Warford Century 21 Pinnacle

  329 Hanover Dr, Winchester, KY 40391
• 

  

  /11

  Est $302,190

  Not Listed For Sale

  435 Fairholme Way, Winchester, KY 40391

  435 Fairholme Way, Winchester, KY 40391

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent Kathryn Cheuvront Coldwell Banker McMahan
• 

  

  /26

  $249,900

  • 3 Beds
  • 2 Baths
  • 1,492 Sq Ft

  317 Vanover Way, Winchester, KY 40391

  Welcome to 317 Vanover Way! This beautiful, well-maintained 3-bedroom, 2-bath home is move-in ready and waiting for its next owner. Step inside to a spacious living room with the bedrooms conveniently located just off the main living area. Coming in from the garage, you'll find a functional mudroom and laundry area that leads directly into the kitchen. Outside, enjoy a nice-sized fenced backyard

  

  Austina Bruton

  Rector Hayden Realtors

  317 Vanover Way, Winchester, KY 40391
• 

  

  /7

  $985

  Total Monthly Price

  • 2 Beds
  • 1 Bath
  • 840 Sq Ft
  • Townhouse for Rent

  74 Holiday Rd, Winchester, KY 40391

  Now accepting applications for this very clean and well maintained 2-bedroom, 1-bathroom property. Located at 74 Holiday Road, this unit features new LVP flooring and offers 840 square feet of living space. The living room provides ample room for relaxation and features a ceiling fan for comfort. The kitchen is equipped with a dishwasher and includes a washer and dryer for added convenience. The

  74 Holiday Rd, Winchester, KY 40391
• 

  

  /52

  $255,000

  Sold Aug 31, 2026

  104 Jackson Ferry Rd, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,417 Sq Ft
  • Built 1850

  Last Sold Summary

  • 7% Below List Price
  • $106/SF
  • 106 Days On Market

  Current Estimated Value $270,671

  Last Listing Agent Bob Sophiea eXp Realty, LLC

  104 Jackson Ferry Rd, Winchester, KY 40391
• 

  

  /5

  Est $128,689

  Not Listed For Sale

  434 Fairholme Way, Winchester, KY 40391

  434 Fairholme Way, Winchester, KY 40391

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Justin Lee JL Realty Group, LLC
• 

  

  /50

  $239,900

  $15K 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

  

  Bill VanWinkle

  Joyce Marcum Realty

  377 Crescent Ave, Winchester, KY 40391
• 

  

  /17

  $2,500 Per Month

  • 4 Beds
  • 2 Baths
  • 1,950 Sq Ft
  • House for Rent

  104 Colby Hills Dr, Winchester, KY 40391

  Garry Milton Milton and Associates Real Estate

  104 Colby Hills Dr, 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 $445,323

  Last Listing Agent Kelli Hunt Berkshire Hathaway HomeServices Foster Realtors

  2 Stoney Brook Dr, Winchester, KY 40391
• 

  

  /16

  Est $261,744

  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
• 

  

  /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
• 

  

  /25

  $1,795 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,879 Sq Ft
  • House for Rent

  230 Prescott Ln, Winchester, KY 40391

  Located in a desirable neighborhood, this spacious house offers 3 bedrooms and 2.5 bathrooms, providing ample space for you and your loved ones. The backyard is complete with a privacy fence, ensuring a serene and secluded atmosphere for outdoor activities. Step out onto the deck and enjoy the fresh air, and enjoy gatherings with friends and family. With a 2 car oversized attached garage, you'll

  230 Prescott Ln, 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 $185,445

  Last Listing Agent Garnett Davis Tom Goebel & Company

  612 Boone Ave, Winchester, KY 40391
• 

  

  /24

  Est $231,024

  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

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