Homes in ZIP Code 40391

• 

  

  

  /9

  $155,000

  $5K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,097 Sq Ft

  220 E Washington St, Winchester, KY 40391

  Charming 3-Bedroom Home with Great Investment Potential....Welcome to this charming 3-bedroom, 1-bath home offering comfortable living space and plenty of opportunity for homeowners or investors alike. Featuring an easy layout with generously sized bedrooms, a large eat-in kitchen, and a bright living area, Outside, you'll find a covered front porch perfect for relaxing, along with a private

  Whitney Ensor Ensor Real Estate, LLC

  220 E Washington St, Winchester, KY 40391
• 

  

  

  /32

  $310,000

  Sold May 01, 2026

  113 Strawberry Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,780 Sq Ft
  • Built 2023

  Last Sold Summary

  • 2% Below List Price
  • $174/SF
  • 1 Day On Market

  Current Estimated Value $317,437

  Last Listing Agent Rob Bolton Christies International Real Estate Bluegrass

  113 Strawberry Ln, Winchester, KY 40391
• 

  

  

  /22

  Est $217,678

  Not Listed For Sale

  44 Buckner St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,309 Sq Ft
  • Built 1935

  44 Buckner St, Winchester, KY 40391

  Last Sold Summary

  • 143 Days On Market
• 

  

  

  /40

  $315,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 1,899 Sq Ft

  305 Abbeywood Dr, Winchester, KY 40391

  Welcome to this updated home situated at the end of a cul de sac in desirable Colby Ridge. Updates include new flooring, appliances, paint & more! This adorable home features a first-floor primary suite, utilities on the first floor, a cozy gas fireplace, an eat-in kitchen, formal dining room & a large living room with a vaulted ceiling. Upstairs, you'll find 2 additional bedrooms, a full bath &

  Shevawn Akers Firefly Realty & Investments

  305 Abbeywood Dr, Winchester, KY 40391
• 

  

  

  /31

  $240,200

  Sold Oct 28, 2025

  203 Inverness Ln, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,935 Sq Ft
  • Built 2004

  Last Sold Summary

  • 2% Below List Price
  • $124/SF
  • 16 Days On Market

  Current Estimated Value $250,190

  Last Listing Agent Kymberly McCreary eXp Realty, LLC

  203 Inverness Ln, Winchester, KY 40391
• 

  

  /17

  Est $325,644

  Not Listed For Sale

  129 S Highland St, Winchester, KY 40391

  • 6 Beds
  • 4 Baths
  • 3,608 Sq Ft
  • Built 1940

  129 S Highland St, Winchester, KY 40391

  Last Sold Summary

  • 86 Days On Market
• 

  

  /21

  $199,900

  Pending

  • 3 Beds
  • 2 Baths
  • 1,140 Sq Ft

  265 Cunningham Ln, Winchester, KY 40391

  (back on the market due to buyers financing) Adventure is always within reach at this property! Located just 35 minutes from Red River Gorge and only 26 minutes from Natural Bridge State Resort Park, this home puts you close to some of Kentucky's most popular outdoor attractions. Spend your weekends hiking scenic trails, canoeing, kayaking, fishing, swimming, riding the sky lift, playing mini

  Kierstin Shaffer Berkshire Hathaway HomeServices Foster Realtors

  265 Cunningham Ln, Winchester, KY 40391
• 

  

  /19

  $221,000

  Sold Jun 16, 2026

  357 Silverton Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,502 Sq Ft
  • Built 1999

  Last Sold Summary

  • 90,847% Above List Price
  • $147/SF
  • 64 Days On Market

  Current Estimated Value $237,860

  Last Listing Agent Frank Mulder Tru Life Real Estate

  357 Silverton Way, Winchester, KY 40391
• 

  

  /17

  Est $169,875

  Not Listed For Sale

  21 Franklin Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,006 Sq Ft
  • Built 1940

  21 Franklin Ave, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market
• 

  

  /6

  $204,900

  Pending

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft

  500 Hidden Hills Way, Winchester, KY 40391

  Ranch with covered porch, new roof, new appliances and countertops, new bath vanity, new professional paint job. Vaulted ceiling in the living room. Clean and ready for occupancy.

  Sondra Clark Taylor Real Estate, LLC

  500 Hidden Hills Way, Winchester, KY 40391
• 

  

  /44

  $847,000

  Sold Apr 22, 2026

  7075 Ecton Rd, Winchester, KY 40391

  • Land
  • 83.71 Acres
  • $10,118 per Acre

  Last Sold Summary

  • 39 Days On Market

  Current Estimated Value $833,000

  Last Listing Agent Jonathan Noel Noel Auctioneers and Real Estate Advisors

  7075 Ecton Rd, Winchester, KY 40391
• 

  

  /23

  Est $181,658

  Not Listed For Sale

  353 E Broadway St, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,905 Sq Ft
  • Built 1940

  353 E Broadway St, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market
• 

  

  /21

  $104,900

  • 2 Beds
  • 2 Baths
  • 924 Sq Ft

  563 Constitution Dr, Winchester, KY 40391

  Affordable housing! Check out this newly remodeled and updated home! 2 bedroom, 2 full bath! All new flooring, cabinets, vanities, and so much more! No lot rent here! You will own the lot as well, making this a great option for starter, downsizing, investment property (previously rented for $925), or just an affordable home. Nice covered porch, 2 storage sheds, brand new metal roof! $150 per

  Jason Townsend Kentucky Residential Real Estate, LLC

  563 Constitution Dr, Winchester, KY 40391
• 

  

  /43

  $339,000

  Sold Feb 12, 2026

  106 Gibson Way, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,064 Sq Ft
  • Built 2021

  Last Sold Summary

  • $164/SF
  • 1 Day On Market

  Current Estimated Value $340,724

  Last Listing Agent Brittany Nester RO&CO Real Estate

  106 Gibson Way, Winchester, KY 40391
• 

  

  /53

  Est $130,254

  Not Listed For Sale

  307 Jackson St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,629 Sq Ft
  • Built 1950

  307 Jackson St, Winchester, KY 40391

  Last Sold Summary

  • 67 Days On Market
• 

  

  /9

  $1,350,000

  $350K PRICE INCREASE

  • Land
  • 3.02 Acres
  • $447,020 per Acre

  155 April Way, Winchester, KY 40391

  Ideally located along the heart of Bypass Road (ADT: 24,801) in Winchester, Kentucky between and surrounding Kroger and Walmart shopping centers. These lots are offered as 1+ acres and may be subdivided. Winchester, KY is the county seat of Clark County, KY and is part of the Lexington-Fayette KY Metropolitan Statistical Area, and is supported by such industries such as Amazon, Ale-8-One, and

  Greg Leveridge Block + Lot Homes

  155 April Way, Winchester, KY 40391
• 

  

  /36

  $472,500

  Sold Sep 09, 2025

  208 Royal Oak Dr, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,593 Sq Ft
  • Built 2007

  Last Sold Summary

  • 1% Above List Price
  • $182/SF
  • 1 Day On Market

  Current Estimated Value $485,191

  Last Listing Agent Megan McCoy Keller Williams Legacy Group

  208 Royal Oak Dr, Winchester, KY 40391
• 

  

  /32

  Est $200,617

  Not Listed For Sale

  230 Winn Ave, Winchester, KY 40391

  • 4 Beds
  • 1.5 Baths
  • 1,400 Sq Ft
  • Built 1940

  230 Winn Ave, Winchester, KY 40391

  Last Sold Summary

  • 73 Days On Market
• 

  

  /38

  $294,900

  $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,128 Sq Ft

  147 Sunset Heights, Winchester, KY 40391

  This charming 3-bedroom, 2-bath home offers the perfect blend of comfort, space, and potential! On a large corner lot in a cute, established neighborhood, this property features a spacious detached garage ideal for storage, hobbies, or workshop space. Inside, you'll find a functional layout with plenty of natural light and room to make it your own. The large partially unfinished basement provides

  Lyndsey Martin Kentucky Land and Home

  147 Sunset Heights, Winchester, KY 40391
• 

  

  /32

  $259,000

  Sold Apr 30, 2026

  414 Wellington Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,251 Sq Ft
  • Built 2007

  Last Sold Summary

  • $207/SF
  • 53 Days On Market

  Current Estimated Value $257,273

  Last Listing Agent Amy Diamond ERA Select Real Estate

  414 Wellington Way, Winchester, KY 40391
• 

  

  /17

  Est $172,606

  Not Listed For Sale

  30 Rowland Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 956 Sq Ft
  • Built 1952

  30 Rowland Ave, Winchester, KY 40391

  Last Sold Summary

  • 0 Days On Market
• 

  

  /35

  $274,900

  • 2 Beds
  • 1 Bath
  • 849 Sq Ft

  955 Right Angle Rd, Winchester, KY 40391

  Newly renovated Cabin sitting on +- 5 acres. Renovations began in 2024 and were completed in 2026. An ideal property for a first-time home buyer or anyone looking for a remote quiet location located within 20 minutes of downtown Winchester.

  Rhett Hughes WTC Realty LLC

  955 Right Angle Rd, Winchester, KY 40391
• 

  

  /23

  $135,000

  Sold Jul 02, 2025

  2100 Old Log Lick Rd, Winchester, KY 40391

  • Land
  • 5 Acres
  • $27,000 per Acre

  Last Sold Summary

  • 10% Below List Price
  • 69 Days On Market

  Current Estimated Value $150,258

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

  2100 Old Log Lick Rd, Winchester, KY 40391
• 

  

  /20

  Est $206,618

  Not Listed For Sale

  314 E Broadway St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,188 Sq Ft
  • Built 1950

  314 E Broadway St, Winchester, KY 40391

  Last Sold Summary

  • 22 Days On Market
• 

  /2

  $100,000

  $10K PRICE DROP

  • Land
  • 13,503 Sq Ft
  • $322,581 per Acre

  215 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

  215 Duclair Dr, Winchester, KY 40391
• 

  

  /15

  $139,000

  Sold May 29, 2026

  37 Ashland Ave, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 904 Sq Ft
  • Built 1940

  Last Sold Summary

  • $154/SF
  • 5 Days On Market

  Current Estimated Value $140,994

  Last Listing Agent Samantha Gray National Real Estate

  37 Ashland Ave, Winchester, KY 40391
• 

  

  /27

  Est $194,079

  Not Listed For Sale

  37 Jackson St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,400 Sq Ft
  • Built 1940

  37 Jackson St, Winchester, KY 40391

  Last Sold Summary

  • 30 Days On Market
• 

  

  /21

  $249,900

  New Construction Pending

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

  12 Pocahontas Trail, Winchester, KY 40391

  Here is your opportunity to purchase a new construction home built in an established neighborhood. Approaching the home you notice the large covered front porch with plenty of room for seating. When you walk in the home, you have white oak LVP flooring running throughout the living room, kitchen and dining area that are all open to one another. The kitchen has white Shaker style cabinets, granite

  Brian England Keller Williams Bluegrass Realty

  12 Pocahontas Trail, Winchester, KY 40391
• 

  

  /20

  $217,500

  Sold Sep 30, 2025

  511 Acadia Way, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 2001

  Last Sold Summary

  • 3% Below List Price
  • $155/SF
  • 28 Days On Market

  Current Estimated Value $219,006

  Last Listing Agent Tyler I Back The Brokerage

  511 Acadia Way, Winchester, KY 40391
• 

  

  /23

  Est $212,247

  Not Listed For Sale

  42 Park Ave, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,129 Sq Ft
  • Built 1940

  42 Park Ave, Winchester, KY 40391

  Last Sold Summary

  • 54 Days On Market
• 

  

  /7

  $800,000

  Pending

  • Land
  • 4.87 Acres
  • $164,271 per Acre

  1108 W Lexington Ave, Winchester, KY 40391

  Rare opportunity to purchase a large multi-family development in the heart of Winchester! Directly across the street from Legacy Grove Park with Lexington Avenue frontage. All building and engineering plans available to build 66 approved townhomes with the possibility of adding 4 more. Currently zoned PD (Planned Development), could possibly be changed to commercial due to neighboring commercial

  Jason Townsend Kentucky Residential Real Estate, LLC

  1108 W Lexington Ave, Winchester, KY 40391
• 

  /2

  $99,500

  Sold Dec 01, 2025

  1295 Sewell Shop Rd, Winchester, KY 40391

  • Land
  • 8.39 Acres
  • $11,859 per Acre

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Zella Rosenthal Tom Goebel & Company

  1295 Sewell Shop Rd, Winchester, KY 40391
• 

  

  /43

  Est $141,225

  Not Listed For Sale

  116 Park Ave, Winchester, KY 40391

  • 1 Bed
  • 1 Bath
  • 1,576 Sq Ft
  • Built 1940

  116 Park Ave, Winchester, KY 40391

  Last Sold Summary

  • 23 Days On Market
• 

  

  /5

  $154,900

  • Land
  • 2.53 Acres
  • $61,250 per Acre

  750 Craig Crossing Unit Lot 7, Winchester, KY 40391

  Great opportunity to own a prime lot in the exclusive Thoroughbred Estates, Winchester's most exclusive subdivision. Located between Winchester and Lexington this location is close to shopping, schools, hospitals and interstates. If your tired of living on a postage stamp lot then this lot is for you. Select your dream house plan and select your builder before it's too late.

  Keith Wilson Coldwell Banker McMahan

  750 Craig Crossing Unit Lot 7, Winchester, KY 40391
• 

  

  /13

  $140,000

  Sold Nov 24, 2025

  220 Pendleton St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 902 Sq Ft

  Last Sold Summary

  • 24% Below List Price
  • $155/SF
  • 37 Days On Market

  Current Estimated Value $143,812

  Last Listing Agent Steve Adams Steven D Adams Real Estate Services, LLC

  220 Pendleton St, Winchester, KY 40391
• 

  

  /25

  Est $223,633

  Not Listed For Sale

  21 Vine St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,080 Sq Ft
  • Built 1960

  21 Vine St, Winchester, KY 40391

  Last Sold Summary

  • 0 Days On Market
• 

  /2

  $100,000

  $10K PRICE DROP

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

  155 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

  155 Duclair Dr, Winchester, KY 40391
• 

  

  /21

  $195,000

  Sold Apr 10, 2026

  319 Essex Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,224 Sq Ft
  • Built 2000

  Last Sold Summary

  • 2% Below List Price
  • $159/SF
  • 3 Days On Market

  Current Estimated Value $196,398

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

  319 Essex Ct, Winchester, KY 40391
• 

  

  /39

  Est $267,790

  Not Listed For Sale

  217 E Washington St, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,183 Sq Ft
  • Built 1940

  217 E Washington St, Winchester, KY 40391

  Last Sold Summary

  • 21 Days On Market
• 

  

  /38

  $284,900

  $12K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,116 Sq Ft

  618 Westmeade Dr, Winchester, KY 40391

  Conveniently located, this charming well kept home features a functional floor plan offering space that can be tailored for those who love to entertain or the growing family. On the main level you'll find the living room, an eat in kitchen, 3 bedrooms and a full bathroom. Off of the kitchen is a large deck that's perfect for get togethers with family or friends. Downstairs has a second living

  Kristi Donaldson United Real Estate Bluegrass

  618 Westmeade Dr, Winchester, KY 40391

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