Homes in ZIP Code 40391

• 

  

  

  /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

  $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 $172,150

  Last Listing Agent Cathleen Gedeon CENTURY 21 Advantage Realty

  52 Judy Ann Ct, Winchester, KY 40391
• 

  

  

  /37

  Est $312,846

  Not Listed For Sale

  311 Fern Ct, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,326 Sq Ft
  • Built 1999

  311 Fern Ct, Winchester, KY 40391

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent Robyn Bradley Woods Realty Group
• 

  

  

  /19

  $259,900

  $10K PRICE DROP

  • 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
• 

  

  

  /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 $220,531

  Last Listing Agent Jennifer Hukill RE/MAX Elite Lexington

  86 Brink Ave, Winchester, KY 40391
• 

  

  /49

  Est $308,597

  Not Listed For Sale

  317 Fern Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,588 Sq Ft
  • Built 1999

  317 Fern Ct, Winchester, KY 40391

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Sherry Stephens Murphy Realty Group
• 

  

  /24

  $229,900

  $6K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,100 Sq Ft

  125 Kittison Dr, Winchester, KY 40391

  Charming ranch home featuring 3 bedrooms, 1 full bath with a spacious layout and inviting curb appeal. Enjoy relaxing or entertaining on the covered back patio overlooking the large backyard with plenty of room for pets, play, or gardening. The kitchen offers beautiful granite countertops, ample cabinet space, and all appliances stay for added convenience. A wonderful opportunity for comfortable

  Kathryn Cheuvront Coldwell Banker McMahan

  125 Kittison 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 $549,782

  Last Listing Agent Janna Chalfant Smith United Real Estate Bluegrass

  445 Lynnway Dr, Winchester, KY 40391
• 

  

  /75

  Est $288,583

  Not Listed For Sale

  314 Fern Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,844 Sq Ft
  • Built 1999

  314 Fern Ct, Winchester, KY 40391

  Last Sold Summary

  • 23 Days On Market

  Last Listing Agent Sherry Stephens Murphy Realty Group
• 

  

  /53

  $519,900

  Pending

  • 4 Beds
  • 3 Baths
  • 3,792 Sq Ft

  123 Winterberry Cir, Winchester, KY 40391

  Welcome to this beautiful 4-bedroom, 3-bath home in the Royal Oak Estates featuring exceptional curb appeal, a welcoming front porch, and a large yard. Inside, the spacious living room boasts vaulted ceilings and a fireplace, creating a warm and inviting atmosphere. The formal dining room is perfect for entertaining, while the split-bedroom floor plan provides privacy and functionality. The large

  Autumn Johannes National Real Estate

  123 Winterberry Cir, 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 $267,863

  Last Listing Agent Jim Woodrum RE/MAX Creative, Winchester

  222 Bracken Ct, Winchester, KY 40391
• 

  

  /35

  Est $262,762

  Not Listed For Sale

  206 Moss Cir, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,773 Sq Ft
  • Built 1997

  206 Moss Cir, Winchester, KY 40391

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent David Baesler Kentucky Dreams Realty
• 

  /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
• 

  

  /27

  $380,000

  Sold Nov 10, 2025

  5705 Mount Sterling Rd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,980 Sq Ft
  • Built 1971

  Last Sold Summary

  • 5% Below List Price
  • $128/SF
  • 50 Days On Market

  Current Estimated Value $389,353

  Last Listing Agent Dale Hatton Dream Maker Realty, LLC

  5705 Mount Sterling Rd, Winchester, KY 40391
• 

  

  /35

  Est $277,410

  Not Listed For Sale

  1896 Mount Sterling Rd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 1,942 Sq Ft
  • Built 1960

  1896 Mount Sterling Rd, Winchester, KY 40391

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Keith Wilson Coldwell Banker McMahan
• 

  

  /17

  $66,000

  $3K PRICE DROP

  • 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
• 

  

  /102

  $525,000

  Sold Dec 22, 2025

  1953 Cabin Creek Rd, Winchester, KY 40391

  • 6 Beds
  • 4.5 Baths
  • 3,846 Sq Ft
  • Built 1980

  Last Sold Summary

  • 4% Below List Price
  • $137/SF
  • 9 Days On Market

  Current Estimated Value $544,934

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  1953 Cabin Creek Rd, Winchester, KY 40391
• 

  

  /38

  Est $319,195

  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
• 

  /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
• 

  

  /59

  $770,000

  Sold Jul 15, 2026

  8353 Wades Mill Rd, Mount Sterling, KY 40353

  • 3 Beds
  • 2 Baths
  • 1,826 Sq Ft
  • Built 1995

  Last Sold Summary

  • 19% Below List Price
  • $422/SF
  • 82 Days On Market

  Current Estimated Value $800,695

  Last Listing Agent Alysia Niva Century 21 Advantage Realty - Georgetown

  8353 Wades Mill Rd, Mount Sterling, KY 40353
• 

  

  /105

  Est $804,527

  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
• 

  

  /23

  $205,000

  New Construction $5K PRICE DROP Pending

  • 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
• 

  

  /114

  $635,000

  Sold Sep 30, 2025

  315 The Woods Ln, Winchester, KY 40391

  • 5 Beds
  • 4.5 Baths
  • 5,524 Sq Ft
  • Built 1995

  Last Sold Summary

  • 2% Below List Price
  • $115/SF
  • 63 Days On Market

  Current Estimated Value $633,193

  Last Listing Agent Terri McGraw FC Tucker Bluegrass

  315 The Woods Ln, Winchester, KY 40391
• 

  

  /44

  Est $382,505

  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
• 

  

  /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
• 

  

  /30

  $189,900

  Sold Mar 16, 2026

  357 E Washington St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,328 Sq Ft
  • Built 1940

  Last Sold Summary

  • 5% Below List Price
  • $143/SF
  • 26 Days On Market

  Current Estimated Value $192,899

  Last Listing Agent Dylan Justice Bluegrass Commercial Real Estate

  357 E Washington St, Winchester, KY 40391
• 

  

  /8

  Est $467,674

  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
• 

  

  /27

  $279,500

  Pending

  • 3 Beds
  • 2.5 Baths
  • 1,963 Sq Ft

  304 Newcastle Ln, Winchester, KY 40391

  This house is located within walking distance of Clark County Preschool, Strode Station and Baker and is within minutes of Winchester Bypass and I-64. The house has 3 bedrooms and 2.5 baths and a bonus room on the 2nd floor that would make a great game room or office. The bonus room would also make a nice 4th bedroom. The owner of the house has replaced all of the kitchen appliances and replaced

  Craig Bridgewater Bridgewater Real Estate

  304 Newcastle Ln, Winchester, KY 40391
• 

  

  /33

  $159,200

  Sold Oct 09, 2025

  646 Laura Dr, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,534 Sq Ft
  • Built 1980

  Last Sold Summary

  • 6% Below List Price
  • $104/SF
  • 16 Days On Market

  Current Estimated Value $243,111

  Last Listing Agent Kimberly Brunson Hunter Real Estate

  646 Laura Dr, Winchester, KY 40391
• 

  

  /20

  Est $383,880

  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
• 

  /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
• 

  

  /31

  $145,000

  Sold May 11, 2026

  730 Byrd Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,160 Sq Ft
  • Built 1960

  Last Sold Summary

  • 6% Below List Price
  • $125/SF
  • 11 Days On Market

  Current Estimated Value $150,524

  Last Listing Agent Patricia Weiderman Kentucky Land and Home

  730 Byrd Ave, Winchester, KY 40391
• 

  

  /33

  Est $304,460

  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

  $108,500

  $77K PRICE DROP

  • Land
  • 11.34 Acres
  • $9,572 per Acre

  4590 Four Mile Rd, Ford, KY 40391

  !!!MAJOR REDUCTION!!! Check It Out! Nature lovers property. There is a rock wall at the top with the Four Mile Creek which runs into the Kentucky River across the road. Nearby are restaurants, boat landings, kayaks and historical sights. The trees will keep it private. Take advantage of this PRICE CHANGE to have a property close to the river!!!

  Garnett Davis Tom Goebel & Company

  4590 Four Mile Rd, Ford, KY 40391
• 

  

  /61

  $220,000

  Sold Nov 10, 2025

  313 Snowden Dr, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,232 Sq Ft
  • Built 1960

  Last Sold Summary

  • 12% Below List Price
  • $179/SF
  • 51 Days On Market

  Current Estimated Value $231,327

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  313 Snowden Dr, Winchester, KY 40391
• 

  

  /16

  Est $188,364

  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
• 

  

  /42

  $340,000

  $20K PRICE DROP

  • 4 Beds
  • 5 Baths
  • 4,798 Sq Ft

  502 W Lexington Ave, Winchester, KY 40391

  Investment opportunity in the heart of Winchester! Brick Triplex featuring a main level, high visibility commercial space with Lexington Avenue frontage and two apartments on the upper level! Each apartment has two bedrooms, one bath. One unit has been recently remodeled, the other has potential for value add. The flexible commercial space contains 3 half baths. Laundry hook-ups in all 3 units!

  Jason Townsend Kentucky Residential Real Estate, LLC

  502 W Lexington Ave, Winchester, KY 40391
• 

  

  /17

  $595,000

  Sold Nov 17, 2025

  304 Winterberry Dr, Winchester, KY 40391

  • 7 Beds
  • 4 Baths
  • 4,386 Sq Ft
  • Built 1999

  Last Sold Summary

  • 1% Below List Price
  • $136/SF
  • 10 Days On Market

  Current Estimated Value $594,512

  Last Listing Agent Beckie Moore Bluegrass Properties Group

  304 Winterberry Dr, Winchester, KY 40391
• 

  

  /86

  Est $299,664

  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
• 

  

  /19

  $220,000

  $45K PRICE DROP Pending

  • 4 Beds
  • 3 Baths
  • 2,445 Sq Ft

  130 E Broadway St, Winchester, KY 40391

  Turnkey downtown triplex with tenants already in place. An excellent addition to any investor's portfolio. Two units have been recently updated, while the third features a long-term tenant with future value-add potential. Property includes two 1BD/1BA units and one 2BD/1BA unit. Tenants pay all utilities directly except water, which is on a RUB system, keeping operating costs low. Strong income

  Sarah May Mayca Property Solutions

  130 E Broadway St, Winchester, KY 40391

Showing Results 401 - 440, Page 11 of 18