Winchester, KY Homes

• 

  

  

  /22

  $180,000

  • Land
  • 10.05 Acres
  • $17,919 per Acre

  3925 Jackson Ferry Rd, Winchester, KY 40391

  This 10.045-acre tract offers the total package...scenic surroundings, river access, and improvements already in place. Situated along a quiet, picturesque drive, the property features a solid barn that has recently been painted and structurally reinforced, adding both character and functionality. With a picturesque build site available, this land is ready for your dream home, hobby farm, and

  

  Christa Joynt

  Keller Williams Commonwealth

  (859) 765-6501

  3925 Jackson Ferry Rd, Winchester, KY 40391
• 

  

  

  /14

  $1,449 Per Month

  • 3 Beds
  • 1.5 Baths
  • 1,670 Sq Ft
  • House for Rent

  308 Graves Dr, Winchester, KY 40391

  Available May 20, 2026 – Recently Renovated Winchester Home!Welcome to your next home in the heart of Winchester! This beautifully updated 3-bedroom, 1.5-bath single-family residence is nestled just off Colby Rd and W Lexington Ave- across the street from Wiseman Park and close to downtown!At Bluegrass Rental Management, we strive to provide an experience that is cost-effective

  308 Graves 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 $436,530

  Last Listing Agent Kelli Hunt Berkshire Hathaway HomeServices Foster Realtors

  2 Stoney Brook Dr, Winchester, KY 40391
• 

  

  

  /27

  Est $289,461

  Not Listed For Sale

  216 Prescott Ln, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,726 Sq Ft
  • Built 2008

  216 Prescott Ln, Winchester, KY 40391

  Last Sold Summary

  • 129 Days On Market
• 

  

  /2

  $78,500

  • Land
  • 9,600 Sq Ft
  • $356,171 per Acre

  Lot 3 Plantations Dr, Winchester, KY 40391

  NOW SELLING SFH Buildable Lots of PHASE ONE: 12 Buildable Lots (minimum lot is 9600+ sqft) of PHASE ONE of Deerlawn's Development located at 2395 Paris Rd (Parent Listing). Earmarked as Winchester, Ky's most anticipated residential development consisting of an ambitious 274+-acre expansion formerly known as the well-established Royal Oaks/Plantation neighborhoods, Phase One has 12 lots ready for

  

  Melia Hord

  MELIA Realty LLC

  (859) 376-1813

  Lot 3 Plantations Dr, Winchester, KY 40391
• 

  

  /14

  $970 Per Month

  • 2 Beds
  • 1 Bath
  • Condo for Rent

  265 S Highland St Unit 4, Winchester, KY 40391

  Welcome to our charming apartment in Winchester, KY! This apartment boasts beautiful wood floors throughout, creating a warm and inviting atmosphere. Enjoy the convenience of a large yard and an in-unit laundry room. Located close to downtown and shopping, you'll have easy access to all the amenities Winchester has to offer. Don't miss out on the opportunity to call this unique apartment

  265 S Highland St 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 $182,660

  Last Listing Agent Garnett Davis Tom Goebel & Company

  612 Boone Ave, Winchester, KY 40391
• 

  

  /65

  Est $425,159

  Not Listed For Sale

  399 Stonecrest Rd, Winchester, KY 40391

  • 3 Beds
  • 4 Baths
  • 4,572 Sq Ft
  • Built 1976

  399 Stonecrest Rd, Winchester, KY 40391

  Last Sold Summary

  • 3 Days On Market
• 

  

  /53

  $268,900

  Pending

  • 4 Beds
  • 2.5 Baths
  • 1,510 Sq Ft

  311 Geronimo Ct, Winchester, KY 40391

  Spacious and well - maintained 4 bedroom home featuring 2 full bathrooms, one half bath which is ready to be upgraded with the addition of a shower to function as an additional full bathroom. This home offers a comfortable layout with replacement windows, a cozy wood burning fireplace and updated stainless steel appliances incuding the range, refrigerator, dishwasher and microwave. Enjoy outdoor

  

  Brenda Sipes

  WEICHERT REALTORS - ABG Properties

  (859) 549-3201

  311 Geronimo Ct, Winchester, KY 40391
• 

  

  /18

  $1,995 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,830 Sq Ft
  • Elevated Living Starts Here Now Pre-Leasing in Winchester, KY

  102 Bellbrook Ln, Winchester, KY 40391

  Now Pre-Leasing in Winchester, KYDiscover luxury two-story living in this brand-new home community. These beautifully designed homes offer 3 bedrooms, 2.5 bathrooms, and an attached two-car garage, blending comfort, style, and convenience. Each residence features modern luxury finishes and spacious layouts perfect for today’s lifestyle.Enjoy resort-style community amenities,

  102 Bellbrook Ln, Winchester, KY 40391
• 

  

  /24

  $277,500

  Sold Aug 21, 2025

  10 Howard Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,588 Sq Ft
  • Built 1961

  Last Sold Summary

  • 3% Below List Price
  • $175/SF
  • 0 Days On Market

  Current Estimated Value $287,231

  Last Listing Agent Holly Goeing The Agency

  10 Howard Dr, Winchester, KY 40391
• 

  

  /33

  Est $340,670

  Not Listed For Sale

  107 Morning Glory Ct, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 1,876 Sq Ft
  • Built 2002

  107 Morning Glory Ct, Winchester, KY 40391

  Last Sold Summary

  • 22 Days On Market
• 

  

  /89

  $939,000

  • 3 Beds
  • 2 Baths
  • 4,019 Sq Ft

  200 Old Log Lick Rd, Winchester, KY 40391

  Behind a private, gated entrance on 14.38 acres, this 3,481 sq ft all-wood cabin estate is a truly rare find in Central Kentucky. Offering 3 bedrooms, 2 bathrooms, and a flexible bonus room perfect as a 4th bedroom or home office, every inch of this home reflects true craftsmanship — rich wood features throughout, a large sunroom, and a screened-in back porch made for long evenings and unhurried

  

  Brad Smith

  RE/MAX Creative, Winchester

  (859) 374-7374

  200 Old Log Lick Rd, Winchester, KY 40391
• 

  /2

  $1,125 Per Month

  • 2 Beds
  • 1.5 Baths
  • 1,150 Sq Ft
  • 292/294 April way

  292-294 April Way Unit 292 april way, Winchester, KY 40391

  292-294 April Way Unit 292 april way, Winchester, KY 40391
• 

  

  /14

  $320,000

  Sold Oct 17, 2025

  3431 Colby Rd, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 5,237 Sq Ft
  • Built 1955

  Last Sold Summary

  • 3% Below List Price
  • $61/SF
  • 7 Days On Market

  Current Estimated Value $348,495

  Last Listing Agent Holly Goeing The Agency

  3431 Colby Rd, Winchester, KY 40391
• 

  

  /65

  Est $303,806

  Not Listed For Sale

  13 Robyn Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,844 Sq Ft
  • Built 1980

  13 Robyn Dr, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market
• 

  /2

  $14,100,000

  • Land
  • 274.52 Acres
  • $51,362 per Acre

  2395 Paris Rd, Winchester, KY 40391

  NOW PRE-SELLING: Deerlawn Development is Winchester, Ky's most anticipated residential development--an ambitious 274+-acre expansion formerly known as the well-established Royal Oaks/Plantation neighborhoods. Located at 2395 Paris Road, and positioned off I-64 at Exit 96 across from the rapidly expanding Industrial Park, Deerlawn is a master-planned community offering 438 single-family homes, and

  

  Melia Hord

  MELIA Realty LLC

  (859) 695-6965

  2395 Paris Rd, Winchester, KY 40391
• 

  

  /41

  $265,000

  Sold Nov 12, 2025

  130 Village Ct, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 1,988 Sq Ft
  • Built 1970

  Last Sold Summary

  • 2% Below List Price
  • $133/SF
  • 4 Days On Market

  Current Estimated Value $271,665

  Last Listing Agent Joyce Ratliff Tom Goebel & Company

  130 Village Ct, Winchester, KY 40391
• 

  

  /35

  Est $291,429

  Not Listed For Sale

  606 Laura Dr, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,240 Sq Ft
  • Built 1974

  606 Laura Dr, Winchester, KY 40391

  Last Sold Summary

  • 82 Days On Market
• 

  

  /17

  $97,500

  • Land
  • 7.99 Acres
  • $12,201 per Acre

  3991 Jackson Ferry Rd, Winchester, KY 40391

  Offering the same peaceful setting and rare river access, this tract provides a fantastic opportunity for recreational land ownership at an affordable price. Backing directly to the Kentucky River, it's an ideal spot for camping, weekend retreats, arrowhead hunting or enjoying the outdoors with kayaking, fishing, and more right at your fingertips. This property's fertile soil opens the door for

  

  Christa Joynt

  Keller Williams Commonwealth

  (859) 600-6640

  3991 Jackson Ferry Rd, Winchester, KY 40391
• 

  

  /31

  $231,000

  Sold Jun 30, 2025

  619 Laura Dr, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,404 Sq Ft
  • Built 1980

  Last Sold Summary

  • $165/SF
  • 17 Days On Market

  Current Estimated Value $245,286

  Last Listing Agent Kevin Bradley KB Realty Group

  619 Laura Dr, Winchester, KY 40391
• 

  

  /51

  Est $585,108

  Not Listed For Sale

  520 Gay Evans Rd, Winchester, KY 40391

  • 3 Beds
  • 4 Baths
  • 3,160 Sq Ft
  • Built 2012

  520 Gay Evans Rd, Winchester, KY 40391

  Last Sold Summary

  • 11 Days On Market
• 

  

  /23

  $150,000

  • Land
  • 9.39 Acres
  • $15,971 per Acre

  3821 Jackson Ferry Rd, Winchester, KY 40391

  If you've been dreaming of building a home with river access, this is it. Located along a breathtaking stretch of Jackson Ferry Road, this 9.392-acre tract offers a rare combination of a viable build site and direct access to the scenic Kentucky River. Whether it's morning coffee overlooking the countryside or afternoons spent kayaking and fishing, this property delivers a lifestyle that's hard

  

  Christa Joynt

  Keller Williams Commonwealth

  (859) 696-7578

  3821 Jackson Ferry Rd, Winchester, KY 40391
• 

  

  /64

  $929,000

  Sold Sep 05, 2025

  1110 Craig Crossing, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,670 Sq Ft
  • Built 2025

  Last Sold Summary

  • 6% Below List Price
  • $348/SF
  • 23 Days On Market

  Current Estimated Value $863,879

  Last Listing Agent Michael Hilario The Agency

  1110 Craig Crossing, Winchester, KY 40391
• 

  

  /12

  Est $156,768

  Not Listed For Sale

  120 Jacob Ct, Winchester, KY 40391

  120 Jacob Ct, Winchester, KY 40391

  Last Sold Summary

  • 210 Days On Market
• 

  

  /72

  $775,000

  • 5 Beds
  • 3 Baths
  • 4,437 Sq Ft

  465 Morris Rd, Winchester, KY 40391

  Dreaming of wide-open spaces and country charm? This beautiful 16-acre property in Clark County offers the perfect blend of comfort and functionality. The stately brick home provides generous living space with classic appeal, offering endless potential. With five bedrooms and three full baths, the home accommodates a variety of living arrangements, whether you need space for guests, a home

  

  Brenda Leigh Walters

  United Real Estate Bluegrass

  (859) 459-0504

  465 Morris Rd, Winchester, KY 40391
• 

  

  /35

  $285,000

  Sold May 01, 2026

  192 Prescott Ln, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,550 Sq Ft
  • Built 2007

  Last Sold Summary

  • 4% Above List Price
  • $184/SF
  • 1 Day On Market

  Current Estimated Value $280,092

  Last Listing Agent Joy Murphy United Real Estate Bluegrass

  192 Prescott Ln, Winchester, KY 40391
• 

  

  /34

  Est $381,870

  Not Listed For Sale

  112 Gibson Way, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,496 Sq Ft
  • Built 2020

  112 Gibson Way, Winchester, KY 40391

  Last Sold Summary

  • 56 Days On Market
• 

  /2

  $882,000

  • Land
  • 3.93 Acres
  • $224,427 per Acre

  Lot 1 - 7 Plantations Dr, Winchester, KY 40391

  NOW SELLING PHASE ONE: 7 of the 12 Buildable Lots (minimum lot is 9600+ sqft) of PHASE ONE of Deerlawn's Development located at 2395 Paris Rd (Parent Listing). Earmarked as Winchester, Ky's most anticipated residential development consisting of an ambitious 274+-acre expansion formerly known as the well-established Royal Oaks/Plantation neighborhoods, Phase One has 12 lots ready for you to build

  

  Melia Hord

  MELIA Realty LLC

  (859) 587-3785

  Lot 1 - 7 Plantations Dr, Winchester, KY 40391
• 

  

  /29

  $285,000

  Sold Jun 12, 2026

  426 E Broadway St, Winchester, KY 40391

  • 5 Beds
  • 2 Baths
  • 1,838 Sq Ft
  • Built 1945

  Last Sold Summary

  • 1% Below List Price
  • $155/SF
  • 12 Days On Market

  Current Estimated Value $285,416

  Last Listing Agent Alyssa M Boley Coldwell Banker McMahan

  426 E Broadway St, Winchester, KY 40391
• 

  

  /77

  Est $488,057

  Not Listed For Sale

  275 Runnymeade Dr, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,495 Sq Ft
  • Built 2017

  275 Runnymeade Dr, Winchester, KY 40391

  Last Sold Summary

  • 21 Days On Market
• 

  

  /17

  $97,500

  • Land
  • 8.46 Acres
  • $11,522 per Acre

  3961 Jackson Ferry Rd, Winchester, KY 40391

  Escape to your own slice of Kentucky countryside with this 8.462-acre tract nestled along a scenic stretch of Jackson Ferry Road. Backing up to the Kentucky River, this property is perfect for recreational use, whether you're looking to camp, garden, or create a weekend getaway. This land provides plenty of space for campers and outdoor enjoyment throughout much of the year. The soil is rich and

  

  Christa Joynt

  Keller Williams Commonwealth

  (859) 295-6825

  3961 Jackson Ferry Rd, Winchester, KY 40391
• 

  

  /19

  $288,500

  Sold Feb 24, 2026

  729 Wayland Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,966 Sq Ft
  • Built 1980

  Last Sold Summary

  • 4% Below List Price
  • $147/SF
  • 92 Days On Market

  Current Estimated Value $289,121

  Last Listing Agent Brittany Beer eXp Realty, LLC

  729 Wayland Dr, Winchester, KY 40391
• 

  

  /16

  Est $260,716

  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
• 

  /2

  $78,500

  • Land
  • 9,600 Sq Ft
  • $356,171 per Acre

  Lot 4 Plantations Dr, Winchester, KY 40391

  NOW SELLING SFH Buildable Lots of PHASE ONE: 12 Buildable Lots (minimum lot is 9600+ sqft) of PHASE ONE of Deerlawn's Development located at 2395 Paris Rd (Parent Listing). Earmarked as Winchester, Ky's most anticipated residential development consisting of an ambitious 274+-acre expansion formerly known as the well-established Royal Oaks/Plantation neighborhoods, Phase One has 12 lots ready for

  

  Melia Hord

  MELIA Realty LLC

  (859) 696-1024

  Lot 4 Plantations Dr, Winchester, KY 40391
• 

  

  /14

  $125,000

  Sold Apr 01, 2026

  464 Ecton Rd, Winchester, KY 40391

  • Land
  • 1.03 Acres
  • $121,359 per Acre

  Last Sold Summary

  • 16% Below List Price
  • 3 Days On Market

  Current Estimated Value $143,008

  Last Listing Agent Vickie Skeens RE/MAX Elite Lexington

  464 Ecton Rd, Winchester, KY 40391
• 

  

  /24

  Est $234,877

  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
• 

  

  /23

  $250,000

  • Land
  • 14.51 Acres
  • $17,228 per Acre

  3056 Irvine Rd, Winchester, KY 40391

  Discover the perfect blend of beauty, privacy, and opportunity with this stunning 14.511-acre tract on Irvine Road. Featuring gently rolling hills, this property offers multiple ideal building sites to bring your dream home to life, whether you're envisioning a modern farmhouse, barndominium, or private country retreat. A barn is already in place, adding immediate functionality for storage,

  

  Christa Joynt

  Keller Williams Commonwealth

  (859) 534-9808

  3056 Irvine Rd, Winchester, KY 40391
• 

  

  /33

  $332,000

  Sold Oct 14, 2025

  1831 Kiddville Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,756 Sq Ft
  • Built 1963

  Last Sold Summary

  • 5% Below List Price
  • $189/SF
  • 82 Days On Market

  Current Estimated Value $328,075

  Last Listing Agent Joshua Davis The Agency

  1831 Kiddville Rd, Winchester, KY 40391
• 

  

  /70

  Est $323,098

  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

Showing Results 41 - 80, Page 2 of 18