Winchester, KY Homes

• 

  

  

  /35

  Est $403,979

  Not Listed For Sale

  2195 Pretty Run Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,062 Sq Ft
  • Built 2000

  2195 Pretty Run Rd, Winchester, KY 40391

  Last Sold Summary

  • 46 Days On Market

  Last Listing Agent Josh Wood Freedom Realty & Property Management
• 

  

  

  /3

  $42,500

  Pending

  • Land
  • 8,712 Sq Ft
  • $212,500 per Acre

  108 Dorset Ln, Winchester, KY 40391

  The restictions state that if it is a ranch plan, there is a minimun of 1300 sq ft. It it is a 1 1/2 story or two story then 1800 sq ft will be required. A two car garage must be attached. Developer will need to approve plans before starting construction This lot is ideal for a walkout basement. Perfect setting for watching the sunsets

  Jo Gawthrop Keller Williams Bluegrass Realty

  108 Dorset Ln, Winchester, KY 40391
• 

  

  

  /30

  $292,000

  Sold Aug 07, 2026

  872 Stratton Ln, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,285 Sq Ft
  • Built 1984

  Last Sold Summary

  • 6% Below List Price
  • $128/SF
  • 15 Days On Market

  Current Estimated Value $306,709

  Last Listing Agent Kathryn Cheuvront Coldwell Banker McMahan

  872 Stratton Ln, Winchester, KY 40391
• 

  

  

  /38

  Est $333,954

  Not Listed For Sale

  3635 Jackson Ferry Rd, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,201 Sq Ft
  • Built 1920

  3635 Jackson Ferry Rd, Winchester, KY 40391

  Last Sold Summary

  • 17 Days On Market

  Last Listing Agent Betsy Brown United Real Estate Bluegrass
• 

  

  

  /18

  $169,000

  $10K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,046 Sq Ft

  175 Magnolia St, Winchester, KY 40391

  Two homes on one lot. Informaton in listing is for the home in the front of the lot. Behind this home is a second home consisting of 2 bedrooms, 1, bath, Living room and kitchen. Main home has been completely remodeled but guest home will require major renevations. The home in the front of the property is vacant but there is a tenant in the home in the rear of the property. The lease is month to

  A. Rebecca Woods Woods Realty Group

  175 Magnolia St, Winchester, KY 40391
• 

  

  /12

  $9,000

  Sold Sep 18, 2025

  406 W Washington St, Winchester, KY 40391

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

  Last Sold Summary

  • 10% Below List Price
  • $6/SF
  • 19 Days On Market

  Current Estimated Value $144,199

  Last Listing Agent Jack Rookard Rookard Real Estate Consultants

  406 W Washington St, Winchester, KY 40391
• 

  

  /105

  Est $801,330

  Not Listed For Sale

  1039 Cole Rd, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,557 Sq Ft
  • Built 1977

  1039 Cole Rd, Winchester, KY 40391

  Last Sold Summary

  • 11 Days On Market

  Last Listing Agent Josh Wood Freedom Realty & Property Management
• 

  

  /7

  $270,000

  $50K PRICE DROP

  • Land
  • 36,590 Sq Ft
  • $321,429 per Acre

  800 Interstate Dr, Winchester, KY 40391

  Visibility, Access, Utilities on site per seller/per plat buyer to verify, zoned B-3. .84 acres located and visible at I-64 exit 96, buyer to verify and satisfy themselves to all aspects and information on property and or inspections sold as is. Buyer to verify water, gas, and electric locations and availability.

  Whitney Ensor Ensor Real Estate, LLC

  800 Interstate Dr, Winchester, KY 40391
• 

  

  /26

  $175,000

  Sold Apr 22, 2026

  10 Pocahontas Trail, Winchester, KY 40391

  • 2 Beds
  • 1.5 Baths
  • 924 Sq Ft
  • Built 1988

  Last Sold Summary

  • $189/SF
  • 7 Days On Market

  Current Estimated Value $177,717

  Last Listing Agent Libby VanMeter Marshall Lane Real Estate - Lexington

  10 Pocahontas Trail, Winchester, KY 40391
• 

  

  /44

  Est $393,825

  Not Listed For Sale

  207 Citation Ct, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 3,304 Sq Ft
  • Built 2005

  207 Citation Ct, Winchester, KY 40391

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Megan McCoy Keller Williams Legacy Group
• 

  

  /19

  $269,900

  Open Sun 2PM - 4PM

  • 3 Beds
  • 1 Bath
  • 2,444 Sq Ft

  2379 Big Stoner Rd, Winchester, KY 40391

  SELLING "AS IS" Welcome to country living!! approximately 1 acre lot with 3-car garage. updates include; new basement doctor system, new range, refrigerator, dishwasher, and washer/dryer. New LVP flooring, new light fixtures inside and out. New septic system, new front storm door and new sliding glass door in dining room. New electric outlets and switch plates. New garage door on lower one car

  Melisa McDonald Wrenn Realty

  2379 Big Stoner Rd, Winchester, KY 40391
• 

  

  /79

  $425,000

  Sold Feb 23, 2026

  1410 Dry Fork Creek Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,064 Sq Ft

  Last Sold Summary

  • 15% Below List Price
  • $399/SF
  • 78 Days On Market

  Last Listing Agent Skyler Lewis Dream Maker Realty, LLC

  1410 Dry Fork Creek Rd, Winchester, KY 40391
• 

  

  /8

  Est $480,806

  Not Listed For Sale

  419 Fairholme Way, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 4,447 Sq Ft
  • Built 2022

  419 Fairholme Way, Winchester, KY 40391

  Last Sold Summary

  • 231 Days On Market

  Last Listing Agent Vickie Skeens RE/MAX Elite Lexington
• 

  /2

  $490,000

  $60K PRICE DROP

  • Land
  • 1.53 Acres
  • $320,261 per Acre

  33-41 Winn Ave, Winchester, KY 40391

  Discover a rare opportunity in downtown Winchester with this assemblage of four vacant lots being sold together as a single offering. Zoned L1 and totaling approximately 1.53 acres, this property presents exceptional potential for redevelopment, infill housing, multiunit residential, mixeduse, or commercial concepts in a central location. Situated just steps from local shops, restaurants,

  Bob Sophiea eXp Realty, LLC

  33-41 Winn Ave, Winchester, KY 40391
• 

  

  /53

  $268,000

  Sold Jul 31, 2026

  311 Geronimo Ct, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 1,510 Sq Ft
  • Built 1999

  Last Sold Summary

  • $177/SF
  • 14 Days On Market

  Current Estimated Value $268,713

  Last Listing Agent Brenda Sipes WEICHERT REALTORS - ABG Properties

  311 Geronimo Ct, Winchester, KY 40391
• 

  

  /20

  Est $406,029

  Not Listed For Sale

  307 Gallahadion Ct, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,487 Sq Ft
  • Built 2004

  307 Gallahadion Ct, Winchester, KY 40391

  Last Sold Summary

  • 18 Days On Market

  Last Listing Agent Lindsay Rhodus Keller Williams Legacy Group
• 

  

  /17

  $69,000

  • 2 Beds
  • 2 Baths
  • 924 Sq Ft

  546 Constitution Dr, Winchester, KY 40391

  This 2 bedroom 2 bath home is perfect for an investor or a family looking for a nice home. All new flooring throughout. New bathroom sinks and commodes. The home backs up to the community park. It is located just minutes from Hamburg or the Winchester Bypass.

  Dale Hatton Dream Maker Realty, LLC

  546 Constitution Dr, Winchester, KY 40391
• 

  

  /24

  $188,000

  Sold Jan 29, 2026

  27 Ashland Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,653 Sq Ft
  • Built 1950

  Last Sold Summary

  • 6% Below List Price
  • $114/SF
  • 112 Days On Market

  Current Estimated Value $188,085

  Last Listing Agent Robin Mobley-Mosher Marshall Lane Real Estate - Lexington

  27 Ashland Ave, Winchester, KY 40391
• 

  

  /33

  Est $302,295

  Not Listed For Sale

  305 Gallahadion Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,475 Sq Ft
  • Built 2004

  305 Gallahadion Ct, Winchester, KY 40391

  Last Sold Summary

  • 55 Days On Market

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC
• 

  /2

  $150,000

  • Land
  • 2.16 Acres
  • $69,444 per Acre

  120 Knox Ct, Winchester, KY 40391

  Looking for a place to build a Upscale home in Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

  John Wilson Bluegrass Properties Group

  120 Knox Ct, Winchester, KY 40391
• 

  

  /52

  $448,000

  Sold Jul 10, 2026

  207 Hibiscus Ln, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 3,126 Sq Ft
  • Built 1999

  Last Sold Summary

  • $143/SF
  • 2 Days On Market

  Current Estimated Value $448,899

  Last Listing Agent Jonathan Wood HomeLand Real Estate Inc - Mt Sterling

  207 Hibiscus Ln, Winchester, KY 40391
• 

  

  /16

  Est $180,111

  Not Listed For Sale

  430 Country Club Dr, Winchester, KY 40391

  • 2 Beds
  • 2 Baths
  • 1,260 Sq Ft
  • Built 1982

  430 Country Club Dr, Winchester, KY 40391

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Brian England Keller Williams Bluegrass Realty
• 

  

  /63

  $1,149,000

  $30K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 3,672 Sq Ft

  2100 Irvine Rd Unit 40391, Winchester, KY 40391

  Seller will need 48 Hours to show, This log cabin is located on gently rolling 28 acres very few miles from town, you will think you are on vacation in the sparking pool, tastefully landscaped, fireplace in the great room which leads into a in law quarters, large kitchen that has been wonderfully remodeled with extensive detail, master suite is located on first floor, mud room, 3 1/2 baths,

  Mila Ensor Ensor Real Estate, LLC

  2100 Irvine Rd Unit 40391, Winchester, KY 40391
• 

  

  /62

  $453,200

  Sold Jul 23, 2026

  1661 Waterworks Rd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,793 Sq Ft
  • Built 1983

  Last Sold Summary

  • 6% Above List Price
  • $162/SF
  • 3 Days On Market

  Current Estimated Value $443,506

  Last Listing Agent Jim Woodrum RE/MAX Creative, Winchester

  1661 Waterworks Rd, Winchester, KY 40391
• 

  

  /86

  Est $300,665

  Not Listed For Sale

  222 Vaught Rd, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,904 Sq Ft
  • Built 1970

  222 Vaught Rd, Winchester, KY 40391

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Josh Wood Freedom Realty & Property Management
• 

  

  /23

  $205,000

  New Construction $5K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft

  30 Hughes Ave, Winchester, KY 40391

  Welcome to this charming newer construction home nestled on a quiet dead-end street in Winchester! Offering 3 bedrooms and 1 full bath, this move-in-ready home features a bright, functional layout with modern finishes throughout. A standout feature is the spacious crawlspace, providing an abundance of storage for seasonal items, tools, or outdoor equipment. Enjoy the peace and privacy of

  Autumn Johannes National Real Estate

  30 Hughes Ave, Winchester, KY 40391
• 

  

  /26

  $165,000

  Sold Apr 23, 2026

  52 Judy Ann Ct, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,312 Sq Ft
  • Built 1981

  Last Sold Summary

  • $126/SF
  • 0 Days On Market

  Current Estimated Value $167,887

  Last Listing Agent Cathleen Gedeon CENTURY 21 Advantage Realty

  52 Judy Ann Ct, Winchester, KY 40391
• 

  

  /38

  Est $282,641

  Not Listed For Sale

  2020 Two Mile Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,320 Sq Ft
  • Built 1950

  2020 Two Mile Rd, Winchester, KY 40391

  Last Sold Summary

  • 37 Days On Market

  Last Listing Agent Dale Hatton Dream Maker Realty, LLC
• 

  

  /37

  $219,000

  $14K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,261 Sq Ft

  14 Cook Ave, Winchester, KY 40391

  Remodeled and move-in ready! Conveniently located in downtown Winchester just minutes from Main Street and I-64, this charming home offers the perfect blend of character and modern updates. Major improvements include a near complete replacement of the heating, plumbing, and electrical systems, giving buyers peace of mind for years to come. Inside, you'll find all new flooring throughout, a

  Janna Chalfant Smith United Real Estate Bluegrass

  14 Cook Ave, Winchester, KY 40391
• 

  

  /20

  $230,000

  Sold Jul 23, 2026

  86 Brink Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,136 Sq Ft
  • Built 2000

  Last Sold Summary

  • $202/SF
  • 12 Days On Market

  Current Estimated Value $216,409

  Last Listing Agent Jennifer Hukill RE/MAX Elite Lexington

  86 Brink Ave, Winchester, KY 40391
• 

  

  /13

  Est $191,661

  Not Listed For Sale

  4 Burton Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,330 Sq Ft
  • Built 1948

  4 Burton Ave, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Amanda McMillian RE/MAX Elite Realty
• 

  

  /39

  $315,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,932 Sq Ft

  13 Lakeview Dr, Winchester, KY 40391

  Beautifully updated brick ranch with a partially finished basement offering 3 bedrooms and 2 full baths! The main level features a welcoming living room with a masonry gas log fireplace that opens into the updated kitchen complete with island bar seating, eat-in dining area, and access to the screened-in deck, perfect for relaxing or entertaining. Down the hall, you'll find two bedrooms, a full

  Michelle Blackburn RE/MAX Creative, Winchester

  13 Lakeview Dr, Winchester, KY 40391
• 

  

  /25

  $375,000

  Sold Aug 29, 2025

  317 Hanover Dr, Winchester, KY 40391

  • 5 Beds
  • 3.5 Baths
  • 3,111 Sq Ft
  • Built 2001

  Last Sold Summary

  • 1% Below List Price
  • $121/SF
  • 8 Days On Market

  Current Estimated Value $382,439

  Last Listing Agent Mike Wheatley Bluegrass Properties Group

  317 Hanover Dr, Winchester, KY 40391
• 

  

  /19

  Est $191,952

  Not Listed For Sale

  223 Blair Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,025 Sq Ft

  223 Blair Ave, Winchester, KY 40391

  Last Sold Summary

  • 82 Days On Market

  Last Listing Agent Jordan James Lifstyl Real Estate
• 

  /2

  $100,000

  $10K PRICE DROP

  • Land
  • 13,939 Sq Ft
  • $312,500 per Acre

  169 Duclair Dr, Winchester, KY 40391

  Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

  John Wilson Bluegrass Properties Group

  169 Duclair Dr, Winchester, KY 40391
• 

  

  /60

  $545,000

  Sold Oct 31, 2025

  445 Lynnway Dr, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 3,649 Sq Ft
  • Built 1993

  Last Sold Summary

  • $149/SF
  • 4 Days On Market

  Current Estimated Value $555,129

  Last Listing Agent Janna Chalfant Smith United Real Estate Bluegrass

  445 Lynnway Dr, Winchester, KY 40391
• 

  

  /26

  Est $193,214

  Not Listed For Sale

  64 Bond Ct, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,025 Sq Ft
  • Built 1987

  64 Bond Ct, Winchester, KY 40391

  Last Sold Summary

  • 18 Days On Market

  Last Listing Agent Jim Woodrum RE/MAX Creative, Winchester
• 

  

  /11

  $139,900

  $15K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 864 Sq Ft

  19 3rd St, Winchester, KY 40391

  3BR/1BA | Winchester, KY Affordable single-family homes are hard to come by at this price — here's your chance. This cozy 3-bedroom, 1-bath home in Winchester sits on a generous lot with a large backyard, long driveway with plenty of parking, a welcoming covered front porch, and accessible front entry with both steps and a ramp. it's efficient and easy to maintain — and don't let the square

  Anthony Gigilo ListWithFreedom.com

  19 3rd St, Winchester, KY 40391
• 

  

  /27

  $263,500

  Sold Apr 10, 2026

  222 Bracken Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,456 Sq Ft
  • Built 2006

  Last Sold Summary

  • 2% Below List Price
  • $181/SF
  • 121 Days On Market

  Current Estimated Value $263,130

  Last Listing Agent Jim Woodrum RE/MAX Creative, Winchester

  222 Bracken Ct, Winchester, KY 40391
• 

  

  /22

  Est $187,979

  Not Listed For Sale

  101 Baldwin Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 925 Sq Ft

  101 Baldwin Ave, Winchester, KY 40391

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent James Jeffries Brickhouse Real Estate

Showing Results 401 - 440, Page 11 of 18