Winchester, KY Homes

• 

  

  

  /20

  $228,500

  $7K PRICE DROP Pending

  • 3 Beds
  • 2 Baths
  • 1,210 Sq Ft

  122 Spruce Ct, Winchester, KY 40391

  Don't miss this move-in ready brick ranch home offering the perfect blend of comfort, style and convenience. Whether you're relaxing indoors or enjoying the outdoor space, this home is ready for its next owner to move right in and start making memories. Conveniently located near shopping, dining, schools, and major roadways, this updated ranch is a must-see. Don't miss your opportunity to own

  Peggy Baldridge HomeFirst Real Estate

  122 Spruce Ct, 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 $391,349

  Last Listing Agent Dale Hatton Dream Maker Realty, LLC

  5705 Mount Sterling Rd, Winchester, KY 40391
• 

  

  

  /28

  Est $226,521

  Not Listed For Sale

  916 Muddy Creek Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,000 Sq Ft
  • Built 1943

  916 Muddy Creek Rd, Winchester, KY 40391

  Last Sold Summary

  • 39 Days On Market

  Last Listing Agent Janet Jones RE/MAX Elite Lexington
• 

  

  

  /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
• 

  

  

  /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 $546,377

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  1953 Cabin Creek Rd, Winchester, KY 40391
• 

  

  /21

  Est $206,451

  Not Listed For Sale

  17 Elizabeth St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,450 Sq Ft
  • Built 1950

  17 Elizabeth St, Winchester, KY 40391

  Last Sold Summary

  • 24 Days On Market

  Last Listing Agent Holly Goeing The Agency
• 

  

  /19

  $235,000

  $30K PRICE DROP

  • 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
• 

  

  /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 $615,502

  Last Listing Agent Terri McGraw FC Tucker Bluegrass

  315 The Woods Ln, Winchester, KY 40391
• 

  

  /20

  Est $248,712

  Not Listed For Sale

  1121 Muddy Creek Rd, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,498 Sq Ft
  • Built 1940

  1121 Muddy Creek Rd, Winchester, KY 40391

  Last Sold Summary

  • 9 Days On Market

  Last Listing Agent Cheri Shaffer Keller Williams Commonwealth
• 

  

  /29

  $219,900

  • Land
  • 23.83 Acres
  • $9,228 per Acre

  3686 Crowe Ridge Rd, Winchester, KY 40391

  Discover the possibilities with this unique dual-property offering at 3686 & 3688 Crowe Ridge Road. Enjoy the peace and privacy of a beautiful country setting with room to spread out and endless potential. Whether you're looking for a primary residence with additional living space, an investment opportunity, or housing for extended family, this property offers versatility that's hard to find.

  Josh Wood Freedom Realty & Property Management

  3686 Crowe Ridge Rd, 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 $186,864

  Last Listing Agent Dylan Justice Bluegrass Commercial Real Estate

  357 E Washington St, Winchester, KY 40391
• 

  

  /17

  Est $95,827

  Not Listed For Sale

  977 Muddy Creek Rd, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,030 Sq Ft
  • Built 1940

  977 Muddy Creek Rd, Winchester, KY 40391

  Last Sold Summary

  • 37 Days On Market

  Last Listing Agent Jason Szaks EXIT Town & Country Realtors
• 

  

  /31

  $89,900

  • 2 Beds
  • 2 Baths
  • 828 Sq Ft

  308 Market St, Winchester, KY 40391

  Newly built and ready for its first owner, this 2-bedroom, 2-bathroom home in Quick Shop delivers the layout and finishes most buyers want without the price tag of new site-built construction. The main living area opens directly into the kitchen, giving the space a connected, airy feel that suits quiet evenings and gatherings alike. Down the hall, 2 bedrooms are sized for real furniture and real

  Hailey Blaylock Quick Shop MHC

  308 Market St, 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 $230,992

  Last Listing Agent Kimberly Brunson Hunter Real Estate

  646 Laura Dr, Winchester, KY 40391
• 

  

  /79

  Est $207,445

  Not Listed For Sale

  205 French Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 946 Sq Ft
  • Built 1959

  205 French Ave, Winchester, KY 40391

  Last Sold Summary

  • 319 Days On Market

  Last Listing Agent Greg Wood Freedom Realty & Property Management
• 

  

  /14

  $199,000

  $16K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft

  104 Bay Hill Dr, Winchester, KY 40391

  You don't want to miss this desirable two primary bedroom home with 2 full bathrooms and large walk-in closets!! There is a gorgeous gas fireplace situated as the focal point of the main living space and an attached one car garage.

  Vanessa Highland Stewart & Co Realty LLC

  104 Bay Hill 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 $147,268

  Last Listing Agent Patricia Weiderman Kentucky Land and Home

  730 Byrd Ave, Winchester, KY 40391
• 

  

  /24

  Est $209,726

  Not Listed For Sale

  5 Kentucky St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,634 Sq Ft
  • Built 1930

  5 Kentucky St, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Melissa Brown Keller Williams Legacy Group
• 

  

  /4

  $35,000

  Pending

  • Land
  • 1 Acre
  • $35,000 per Acre

  2828 Athens Boonesboro Rd, Winchester, KY 40391

  Property has electric, water, and a septic tank located on site. The septic tank is underground and may need work as it is small and was constructed in the 90's for a two bedroom home capacity.

  Kristian Kiskaden Keller Williams Commonwealth

  2828 Athens Boonesboro Rd, Winchester, 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 $230,857

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  313 Snowden Dr, Winchester, KY 40391
• 

  

  /23

  Est $184,392

  Not Listed For Sale

  11 Kentucky St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,708 Sq Ft
  • Built 1920

  11 Kentucky St, Winchester, KY 40391

  Last Sold Summary

  • 9 Days On Market

  Last Listing Agent Darrell Lewis DIY Flat Fee.com
• 

  

  /63

  $785,000

  Pending

  • 5 Beds
  • 2.5 Baths
  • 4,676 Sq Ft

  217 Wades Mill Rd, Winchester, KY 40391

  Escape to the peace and privacy of country living with this spacious brick one-and-a-half story home situated on just over 5 acres. With plenty of room to spread out, the main level offers a welcoming foyer, formal dining room, living room with a wood-burning fireplace, kitchen featuring granite countertops, tile backsplash, breakfast nook, and laundry room, along with the primary suite, three

  Michelle Blackburn RE/MAX Creative, Winchester

  217 Wades Mill Rd, 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 $598,334

  Last Listing Agent Beckie Moore Bluegrass Properties Group

  304 Winterberry Dr, Winchester, KY 40391
• 

  

  /18

  Est $124,808

  Not Listed For Sale

  129 Kentucky St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,080 Sq Ft
  • Built 1940

  129 Kentucky St, Winchester, KY 40391

  Last Sold Summary

  • 46 Days On Market

  Last Listing Agent Austin Polley The Polley Group
• 

  

  /15

  $120,000

  • Land
  • 4.14 Acres
  • $28,986 per Acre

  3999 Bybee Rd, Winchester, KY 40391

  Discover the perfect setting for your dream home on this beautiful 4.14-acre tract at 3999 Bybee Road, Winchester, KY 40391. Nestled among the rolling hills of Kentucky's Bluegrass region, this picturesque property offers stunning panoramic countryside views and the peace and privacy you've been searching for. The gently rolling terrain provides multiple potential building sites, giving you the

  Kristey Wood eXp Realty, LLC

  3999 Bybee Rd, Winchester, KY 40391
• 

  /2

  $185,000

  Sold Nov 28, 2025

  23 Hillcrest Dr, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,557 Sq Ft
  • Built 1962

  Last Sold Summary

  • 12% Below List Price
  • $119/SF
  • 18 Days On Market

  Current Estimated Value $205,013

  Last Listing Agent Samantha Gray National Real Estate

  23 Hillcrest Dr, Winchester, KY 40391
• 

  

  /15

  Est $202,824

  Not Listed For Sale

  20 Elizabeth St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,258 Sq Ft
  • Built 1940

  20 Elizabeth St, Winchester, KY 40391

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Jessica Moreno SimpliHOM
• 

  

  /62

  $319,900

  $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,904 Sq Ft

  335 Newcastle Ln, Winchester, KY 40391

  Welcome to this well-maintained home located in a quiet, established neighborhood with convenient access to everything Winchester has to offer. The first floor features an open and inviting layout, creating a comfortable space for everyday living and entertaining alike. Upstairs, you'll find a traditional three-bedroom floor plan with generously sized bedrooms, including a spacious primary suite.

  Josh Wood Freedom Realty & Property Management

  335 Newcastle Ln, Winchester, KY 40391
• 

  

  /25

  $222,000

  Sold Jun 11, 2026

  213 Short St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,068 Sq Ft
  • Built 1955

  Last Sold Summary

  • 3% Below List Price
  • $208/SF
  • 2 Days On Market

  Current Estimated Value $223,859

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  213 Short St, Winchester, KY 40391
• 

  

  /46

  Est $197,769

  Not Listed For Sale

  115 Georgia St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,167 Sq Ft
  • Built 1940

  115 Georgia St, Winchester, KY 40391

  Last Sold Summary

  • 66 Days On Market

  Last Listing Agent Darrell Tackett Dream Maker Realty, LLC
• 

  /2

  $100,000

  $10K PRICE DROP

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

  115 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

  115 Duclair Dr, Winchester, KY 40391
• 

  

  /22

  $216,000

  Sold Feb 27, 2026

  521 Acadia Way, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,370 Sq Ft
  • Built 2001

  Last Sold Summary

  • 2% Below List Price
  • $158/SF
  • 17 Days On Market

  Current Estimated Value $215,450

  Last Listing Agent Tyler I Back The Brokerage

  521 Acadia Way, Winchester, KY 40391
• 

  

  /17

  Est $226,245

  Not Listed For Sale

  102 Kentucky St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,734 Sq Ft
  • Built 1940

  102 Kentucky St, Winchester, KY 40391

  Last Sold Summary

  • 41 Days On Market

  Last Listing Agent Holly Spradlin KY Realty Co
• 

  

  /45

  $361,000

  $54K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,803 Sq Ft

  608 Colby Rd, Winchester, KY 40391

  E Anthony Phillips RE/MAX Creative Realty

  608 Colby Rd, Winchester, KY 40391
• 

  

  /86

  $515,000

  Sold Apr 17, 2026

  125 Casa Landa Way, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 3,848 Sq Ft
  • Built 1999

  Last Sold Summary

  • 6% Below List Price
  • $134/SF
  • 88 Days On Market

  Current Estimated Value $520,628

  Last Listing Agent Maggie Napier Napier Realtors

  125 Casa Landa Way, Winchester, KY 40391
• 

  

  /16

  Est $372,753

  Not Listed For Sale

  122 French Ave, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 4,176 Sq Ft
  • Built 1920

  122 French Ave, Winchester, KY 40391

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Brenda Sipes Bridgewater Real Estate
• 

  

  /30

  $274,500

  $15K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,420 Sq Ft

  137 Eastridge Dr, Winchester, KY 40391

  Welcome to this delightful 1.5-story home perfectly situated on a spacious corner lot just off the Eastern Bypass and only minutes from I-64. Convenience meets comfort in this beautifully maintained property offering 3 bedrooms, 2 full baths, and an inviting layout designed for everyday living. Step inside to an open living area ideal for entertaining, a spacious kitchen and dining space, and

  Kathy Burton Coldwell Banker McMahan

  137 Eastridge Dr, Winchester, KY 40391
• 

  

  /65

  $385,000

  Sold Dec 11, 2025

  1731 Ford Hampton Rd, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,111 Sq Ft
  • Built 2001

  Last Sold Summary

  • 27% Below List Price
  • $182/SF
  • 157 Days On Market

  Current Estimated Value $409,389

  Last Listing Agent Julie Wiggington RE/MAX Creative, Winchester

  1731 Ford Hampton Rd, Winchester, KY 40391
• 

  

  /31

  Est $173,497

  Not Listed For Sale

  134 Central Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,946 Sq Ft
  • Built 1930

  134 Central Ave, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Mila Ensor Ensor Real Estate, LLC
• 

  

  /23

  $175,000

  $5K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,228 Sq Ft

  220 Jackson St, Winchester, KY 40391

  Welcome to 220 Jackson Street in Winchester, KY 40391 - a great opportunity to own a home full of character in a convenient location. Whether you're a first-time buyer, investor, or looking to downsize, this property offers both comfort and potential. Inside, you'll find a functional layout with inviting living spaces that make everyday living easy. The home provides a warm and welcoming feel,

  Hunter Miller GSP Homes

  220 Jackson St, Winchester, KY 40391

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