Winchester, KY Homes

• 

  

  

  /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
• 

  

  

  /26

  $239,900

  Sold Jun 23, 2025

  134 Boone Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,878 Sq Ft
  • Built 1920

  Last Sold Summary

  • 3% Below List Price
  • $128/SF
  • 74 Days On Market

  Current Estimated Value $268,271

  Last Listing Agent Steve Lindsey CENTURY 21 Commonwealth Real Estate

  134 Boone 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
• 

  

  

  /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
• 

  

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
  • 13,503 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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /29

  Est $251,363

  Not Listed For Sale

  167 E Washington St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,763 Sq Ft
  • Built 1940

  167 E Washington St, Winchester, KY 40391

  Last Sold Summary

  • 5 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
• 

  

  /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
• 

  

  /26

  Est $192,198

  Not Listed For Sale

  150 W Broadway St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,696 Sq Ft
  • Built 1940

  150 W Broadway St, Winchester, KY 40391

  Last Sold Summary

  • 39 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
• 

  

  /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
• 

  

  /11

  Est $130,957

  Not Listed For Sale

  30 Madison Ave, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft
  • Built 1996

  30 Madison Ave, Winchester, KY 40391

  Last Sold Summary

  • 18 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
• 

  

  /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 $175,502

  Not Listed For Sale

  2 1st St, Winchester, KY 40391

  • 5 Beds
  • 2 Baths
  • 1,776 Sq Ft
  • Built 1945

  2 1st St, Winchester, KY 40391

  Last Sold Summary

  • 0 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
• 

  

  /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
• 

  

  /16

  Est $186,107

  Not Listed For Sale

  123 2nd St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,298 Sq Ft

  123 2nd St, Winchester, KY 40391

  Last Sold Summary

  • 0 Days On Market
• 

  

  /42

  $420,000

  • 3 Beds
  • 2.5 Baths
  • 2,235 Sq Ft

  19 Fontaine Blvd, Winchester, KY 40391

  Charming story and a half home nestled in a well established neighborhood, featuring beautiful hardwood floors and an updated kichen with modern finishes and ample cabinet space. Relax and entertain with ease on the screened back deck overlooking the large fenced backyard and enjoy the added bonus of a charming gazebo, perect for outdoor gathers or peaceful evenings. This well maintaned home

  Kathryn Cheuvront Coldwell Banker McMahan

  19 Fontaine Blvd, 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
• 

  

  /22

  Est $202,022

  Not Listed For Sale

  160 Autumn Ct, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,287 Sq Ft
  • Built 1960

  160 Autumn Ct, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market
• 

  

  /27

  $152,500

  • 3 Beds
  • 1.5 Baths
  • 1,680 Sq Ft

  65 Fitch Ave, Winchester, KY 40391

  Lovely older home, located witin waking distance to collage park whice offers Pickle Ball, Pool, Tennis, play gound and Walking Trail, also walking distance to Historic Downtown Winchester, with a little love house brings large rooms and a nostlogic atmosphire, take a look, view today, this a a great price for 3 bedrooms, 1 1/2 baths, nice back yard, with parking, call today! Selling "AS IS",

  Mila Ensor Ensor Real Estate, LLC

  65 Fitch 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
• 

  

  /74

  Est $604,872

  Not Listed For Sale

  4 Moundale Ave, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,941 Sq Ft
  • Built 1945

  4 Moundale Ave, Winchester, KY 40391

  Last Sold Summary

  • 3 Days On Market
• 

  

  /3

  $825,000

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,995 Sq Ft

  111 Bella Shae Way, Winchester, KY 40391

  Welcome Home to the Park Place Floor Plan by CP Builders. This elegant ranch home features all-brick construction and a thoughtfully designed split bedroom layout for maximum privacy. The open floor plan seamlessly connects the living, dining, and kitchen areas, creating a warm and inviting atmosphere. Thespacious kitchen is a chef's dream, boasting a large island, a convenient pantry, and a

  Shane Underwood Keller Williams Commonwealth

  111 Bella Shae Way, 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
• 

  

  /43

  Est $263,534

  Not Listed For Sale

  373 Crescent Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,009 Sq Ft
  • Built 1940

  373 Crescent Ave, Winchester, KY 40391

  Last Sold Summary

  • 28 Days On Market
• 

  

  /27

  $235,000

  Pending

  • 4 Beds
  • 2 Baths
  • 1,431 Sq Ft

  13 Arlington Rd, Winchester, KY 40391

  One Level Living!!!! This home boasts all the curb appeal with new vinyl siding, new roof and new leaf filter gutter system on home all in 2025!! A vinyl style privacy fenced in back yard, mature trees and beautiful landscaping! 4 bedrooms, 2 full bathrooms, Kitchen with all appliances (range, dishwasher, refrigerator, microwave) with updated flooring! Hardwood floors are showcased in the main

  Whitney Ensor Ensor Real Estate, LLC

  13 Arlington Rd, Winchester, KY 40391

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