Winchester, KY Homes

• 

  

  

  /19

  $250,000

  $15K 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
• 

  

  

  /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 $190,222

  Last Listing Agent Dylan Justice GSP Homes

  357 E Washington St, Winchester, KY 40391
• 

  

  

  /8

  Est $487,932

  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
• 

  

  

  /43

  $299,900

  Pending

  • 3 Beds
  • 3 Baths
  • 2,821 Sq Ft

  3622 Stamper Dr, Winchester, KY 40391

  This lovely and unique home sits at the end of a quiet street in a secluded circle and backs up to a privacy fenced yard and greenspace right in the heart of town. With recently installed vinyl siding, gutters and gutter guard properties like this are hard to find and the unique amenities inside truly set this home apart. Step through the front door to discover a spacious great room with gleaming

  Josh Wood Freedom Realty & Property Management

  3622 Stamper Dr, 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 $230,813

  Last Listing Agent Kimberly Brunson Hunter Real Estate

  646 Laura Dr, Winchester, KY 40391
• 

  

  /20

  Est $395,533

  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
• 

  

  /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
• 

  

  /32

  $183,000

  Sold Jul 30, 2025

  517 Hidden Hills Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 2001

  Last Sold Summary

  • $163/SF
  • 78 Days On Market

  Current Estimated Value $212,456

  Last Listing Agent Brenda Sipes Bridgewater Real Estate

  517 Hidden Hills Way, Winchester, KY 40391
• 

  

  /33

  Est $313,562

  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
• 

  

  /54

  $649,900

  $100K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 3,388 Sq Ft

  1480 Irvine Rd, Winchester, KY 40391

  Beautifully remodeled farmhouse on 10 fenced acres! This 3 bedroom, 3.5 bath home with a fully finished basement offers the perfect blend of modern upgrades and country living. Inside, you'll find refinished hardwood floors and fresh paint throughout. The custom kitchen is designed to impress with new cabinetry, granite countertops, glass subway tile backsplash, double ovens, two dishwashers, and

  Ivanna Barko National Real Estate

  1480 Irvine Rd, 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 $145,107

  Last Listing Agent Patricia Weiderman Kentucky Land and Home

  730 Byrd Ave, Winchester, KY 40391
• 

  

  /16

  Est $194,999

  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
• 

  

  /20

  $354,900

  New Construction Open Sun 2PM - 4PM $14K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,266 Sq Ft

  107 Gibson Way, Winchester, KY 40391

  A beautiful designed spacious house that offers 3 bedrooms, 3 full bathrooms, and 2266 sq ft og thoughtfully designed living space. Step inside to discover an open-concept layout perfect for both everyday living and entertaining. The well-appointed kitchen flows seamlessly into the main living areas, creating a warm and inviting atmosphere. Generously sized bedrooms provide comfort and privacy,

  Vanessa Highland Stewart & Co Realty LLC

  107 Gibson Way, 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 $231,647

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  313 Snowden Dr, Winchester, KY 40391
• 

  

  /86

  Est $303,769

  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
• 

  

  /62

  $329,900

  • 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
• 

  

  /32

  $285,000

  Sold Jul 03, 2025

  602 Laura Dr, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,690 Sq Ft
  • Built 1976

  Last Sold Summary

  • 11% Below List Price
  • $169/SF
  • 168 Days On Market

  Current Estimated Value $289,370

  Last Listing Agent Ryan O'Gara Real Broker, LLC

  602 Laura Dr, Winchester, KY 40391
• 

  

  /38

  Est $298,125

  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
• 

  /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
• 

  

  /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 $592,900

  Last Listing Agent Beckie Moore Bluegrass Properties Group

  304 Winterberry Dr, Winchester, KY 40391
• 

  

  /13

  Est $189,291

  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
• 

  

  /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
• 

  /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 $204,467

  Last Listing Agent Samantha Gray National Real Estate

  23 Hillcrest Dr, Winchester, KY 40391
• 

  

  /19

  Est $199,366

  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
• 

  

  /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
• 

  

  /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 $227,317

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  213 Short St, Winchester, KY 40391
• 

  

  /26

  Est $193,286

  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
• 

  /2

  $110,000

  • Land
  • 14,810 Sq Ft
  • $323,529 per Acre

  230 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

  230 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 $218,083

  Last Listing Agent Tyler I Back The Brokerage

  521 Acadia Way, Winchester, KY 40391
• 

  

  /22

  Est $187,480

  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
• 

  

  /37

  $1,575,000

  $20K PRICE DROP

  • 37 Beds
  • 19.5 Baths
  • 26,124 Sq Ft

  2 N Main St, Winchester, KY 40391

  Major CAPEX in 2022 & 2024 — Facade transformation, fully restored and renovated.Current grossing $168,000 annual rent, with $4,000/month upside — beats the 1% rule! The Kerr Building, the largest downtown historical landmark, features structural repairs, new roofing, brick tuck-pointing, secure key-fob entrances, central HVAC, modern kitchens, updated baths, and new flooring. 18 LIHTC

  Blanca Cheung Tsubaki Group, LLC

  2 N Main St, 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 $522,883

  Last Listing Agent Maggie Napier Napier Realtors

  125 Casa Landa Way, Winchester, KY 40391
• 

  

  /28

  Est $239,664

  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
• 

  

  /4

  $625,000

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,405 Sq Ft

  424 Alexis Way, Winchester, KY 40391

  Introducing the Castleton, a stunning home designed to impress in the sought-after Mallard Cove neighborhood. This exquisite floor plan features a side-turned garage and captivating curb appeal with double front entry doors. Inside, you'll find a thoughtfully designed split-bedroom layout with a spacious primary suite that includes a luxurious ensuite with a walk-in closet, double vanity, tile

  Shane Underwood Keller Williams Commonwealth

  424 Alexis Way, Winchester, KY 40391
• 

  

  /27

  $269,000

  Sold Apr 20, 2026

  916 Stratton Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1988

  Last Sold Summary

  • $192/SF
  • 0 Days On Market

  Current Estimated Value $269,256

  Last Listing Agent Joshua Davis The Agency

  916 Stratton Ln, Winchester, KY 40391
• 

  

  /21

  Est $218,862

  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
• 

  

  /25

  $255,000

  $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,809 Sq Ft

  316 Maryland Ave, Winchester, KY 40391

  Brick ranch on a partially finished basement offering 3 bedrooms and 2 full baths! The main level welcomes you into a comfortable living room featuring a masonry wood-burning fireplace, along with a spacious kitchen, all three bedrooms, and a full bath located down the hall. The kitchen provides access to the basement where you'll find additional living space in the cozy den area complete with a

  Michelle Blackburn RE/MAX Creative, Winchester

  316 Maryland Ave, 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 $411,446

  Last Listing Agent Julie Wiggington RE/MAX Creative, Winchester

  1731 Ford Hampton Rd, Winchester, KY 40391
• 

  

  /20

  Est $244,759

  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
• 

  

  /14

  $1,115,000

  • Land
  • 120 Acres
  • $9,292 per Acre

  345 Providence Ln, Winchester, KY 40391

  Possible option to purchase the full 202 acres! Rare opportunity to own approximately 120 acres of beautiful rolling farmland in Clark County! This versatile property offers a mix of cleared pasture and wooded acreage, ideal for cattle, horses, recreation, or your dream homestead. Including a large pond plus county water available at the road this property is well-suited for agricultural use. The

  Megan McCoy Keller Williams Legacy Group

  345 Providence Ln, Winchester, KY 40391

Showing Results 441 - 480, Page 12 of 18