Homes in ZIP Code 40391

• 

  

  

  /20

  $235,000

  • 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
• 

  

  

  /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
• 

  

  

  /49

  Est $313,514

  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
• 

  

  

  /42

  $350,000

  $10K 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
• 

  

  

  /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
• 

  

  /75

  Est $300,254

  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
• 

  

  /34

  $349,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 2,274 Sq Ft

  405 Tremont Ln, Winchester, KY 40391

  Welcome to this beautifully maintained 4 bedroom, 2.5 bathroom home over 2,200 square feet of comfortable living space. Built in 2005, this two story home features a functional layout with the primary suite and laundry conveniently located on the main level. Step into fresh paint, undated vinyl flooring and a spacious living area complete with a cozy fireplace perfect for entertaining or

  Darryl Bond Guide Realty, Inc.

  405 Tremont Ln, 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
• 

  

  /35

  Est $265,184

  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
• 

  

  /59

  $274,900

  Pending

  • 3 Beds
  • 2 Baths
  • 1,311 Sq Ft

  403 Pueblo Ct, Winchester, KY 40391

  Built in 2020, this well-maintained Craftsman-style ranch offers the benefits of newer construction without the wait or added cost. Located in Winchester, KY, this home combines comfort, functionality, and convenience in one clean package. Featuring 3 bedrooms and 2 full baths, the layout is designed for everyday living with an open feel and thoughtful flow throughout. The kitchen includes

  Josh Wood Freedom Realty & Property Management

  403 Pueblo Ct, 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
• 

  

  /35

  Est $293,928

  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
• 

  

  /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
• 

  

  /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
• 

  

  /35

  Est $412,025

  Not Listed For Sale

  2195 Pretty Run Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,062 Sq Ft
  • Built 2000

  2195 Pretty Run Rd, Winchester, KY 40391

  Last Sold Summary

  • 46 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
• 

  

  /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
• 

  

  /38

  Est $357,211

  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
• 

  

  /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
• 

  /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
• 

  

  /105

  Est $778,748

  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
• 

  

  /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
• 

  

  /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
• 

  

  /44

  Est $382,194

  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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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 $411,446

  Last Listing Agent Julie Wiggington RE/MAX Creative, Winchester

  1731 Ford Hampton Rd, 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
• 

  

  /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
• 

  

  /79

  $584,900

  Sold Feb 17, 2026

  180 Casa Landa Way, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 4,779 Sq Ft
  • Built 2000

  Last Sold Summary

  • 10% Below List Price
  • $122/SF
  • 46 Days On Market

  Current Estimated Value $595,170

  Last Listing Agent Janna Chalfant Smith United Real Estate Bluegrass

  180 Casa Landa Way, 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
• 

  /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

Showing Results 441 - 480, Page 12 of 18