Homes in ZIP Code 40391

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  /47

  $445,500

  • 3 Beds
  • 2.5 Baths
  • 2,961 Sq Ft

  42 Mockingbird Valley Rd, Winchester, KY 40391

  This is a perfect home for EVERY season.....enjoy multiple, interior gathering spaces and the glow and warmth of either the L R or Dining Room fireplace on the main level or the coziness of the mesmerizing fireplace in the lower level family room during the winter. Watch the backyard come alive with rich and lush vegetation during the Spring from the large, glass walled sun room. For Summer, tons

  Markus Cross McCallie Real Estate

  42 Mockingbird Valley Rd, Winchester, KY 40391
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  /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 $528,414

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  1953 Cabin Creek Rd, Winchester, KY 40391
• 

  

  

  /19

  Est $222,001 Not Listed For Sale

  112 Central Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 2025

  112 Central Ave, Winchester, KY 40391

  Last Sold Summary

  • 1% Above List Price
  • $183/SF
  • 1 Day On Market

  • Last Sold Price $220,000
  • Apr 23, 2025

  Last Listing Agent Nena Honaker Tom Goebel & Company
• 

  

  /2

  $100,000

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

  169 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

  169 Duclair Dr, Winchester, KY 40391
• 

  

  

  /28

  $345,000 Sold Jun 19, 2025

  512 Boone Ave, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 3,149 Sq Ft
  • Built 1950

  Last Sold Summary

  • 14% Below List Price
  • $110/SF
  • 58 Days On Market

  Current Estimated Value $382,030

  Last Listing Agent Jordan James Lifstyl Real Estate

  512 Boone Ave, Winchester, KY 40391
• 

  

  /8

  Est $240,319 Not Listed For Sale

  109 Alabama St, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,359 Sq Ft
  • Built 1930

  109 Alabama St, Winchester, KY 40391

  Last Sold Summary

  • 6% Above List Price
  • $167/SF
  • 9 Days On Market

  • Last Sold Price $227,000
  • May 31, 2023

  Last Listing Agent Andrew Fugitt Coldwell Banker McMahan
• 

  

  /11

  $148,000

  • 3 Beds
  • 1 Bath
  • 864 Sq Ft

  19 3rd St, Winchester, KY 40391

  3BR/1BA | Winchester, KY Affordable single-family homes are hard to come by at this price — here's your chance. This cozy 3-bedroom, 1-bath home in Winchester sits on a generous lot with a large backyard, long driveway with plenty of parking, a welcoming covered front porch, and accessible front entry with both steps and a ramp. it's efficient and easy to maintain — and don't let the square

  Anthony Gigilo ListWithFreedom.com

  19 3rd St, Winchester, KY 40391
• 

  

  /65

  $380,000 Sold Jun 19, 2025

  399 Stonecrest Rd, Winchester, KY 40391

  • 3 Beds
  • 4 Baths
  • 4,572 Sq Ft
  • Built 1976

  Last Sold Summary

  • 4% Below List Price
  • $83/SF
  • 3 Days On Market

  Current Estimated Value $403,866

  Last Listing Agent ROBIN TRIMBLE HomeFirst Real Estate

  399 Stonecrest Rd, Winchester, KY 40391
• 

  

  /23

  Est $199,506 Not Listed For Sale

  112 Georgia St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,738 Sq Ft
  • Built 1930

  112 Georgia St, Winchester, KY 40391

  Last Sold Summary

  • 25% Above List Price
  • $92/SF
  • 8 Days On Market

  • Last Sold Price $160,000
  • Nov 07, 2023

  Last Listing Agent Wayne Elkins RE/MAX
• 

  

  /101

  $1,290,000 Pending

  • 5 Beds
  • 5 Baths
  • 5,666 Sq Ft

  3760 Old Boonesboro Rd, Winchester, KY 40391

  Step through the striking red front doors and into a home where craftsmanship, character, and comfort come together. This beautifully maintained property sits on nearly 13 acres at the edge of Winchester, offering a peaceful retreat with the charm of a mid century floorplan and rich woodwork, tile, and hardwood floors throughout. The spacious kitchen and all three full baths feature high end

  Josh Wood Freedom Realty & Property Management

  3760 Old Boonesboro Rd, Winchester, KY 40391
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  /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 $624,817

  Last Listing Agent Terri McGraw FC Tucker Bluegrass

  315 The Woods Ln, Winchester, KY 40391
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  /48

  Est $247,455 Not Listed For Sale

  104 Georgia St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,758 Sq Ft
  • Built 1930

  104 Georgia St, Winchester, KY 40391

  Last Sold Summary

  • 1% Above List Price
  • $139/SF
  • 9 Days On Market

  • Last Sold Price $245,000
  • Dec 23, 2024

  Last Listing Agent Libby VanMeter Marshall Lane Real Estate - Lexington
• 

  /2

  $108,500

  • Land
  • 11.34 Acres
  • $9,572 per Acre

  4590 Four Mile Rd, Ford, KY 40391

  !!!MAJOR REDUCTION!!! Check It Out! Nature lovers property. There is a rock wall at the top with the Four Mile Creek which runs into the Kentucky River across the road. Nearby are restaurants, boat landings, kayaks and historical sights. The trees will keep it private. Take advantage of this PRICE CHANGE to have a property close to the river!!!

  Garnett Davis Tom Goebel & Company

  4590 Four Mile Rd, Ford, 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 $186,740

  Last Listing Agent Dylan Justice GSP Homes

  357 E Washington St, Winchester, KY 40391
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  /44

  Est $187,907 Not Listed For Sale

  118 Alabama St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,408 Sq Ft
  • Built 1940

  118 Alabama St, Winchester, KY 40391

  Last Sold Summary

  • 32% Above List Price
  • $101/SF
  • 1 Day On Market

  • Last Sold Price $142,000
  • Jul 18, 2024

  Last Listing Agent Susan Moore Keller Williams Legacy Group
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  /55

  $645,000

  • 4 Beds
  • 3.5 Baths
  • 3,431 Sq Ft

  7919 Mount Sterling Rd, Winchester, KY 40391

  Don't let this stunning, 3,431sqft home featuring 4 bed rooms and 3 full baths, sitting on 3 acres, slip through your hands! Custom built brick home nestled in a serene, park like setting overlooking Stoner Creek. Step into to the dramatic two story entryway welcoming you with custom cabinetry and detailed finishes throughout. One of the most captivating features is the sunroom, overlooking the

  Hannah Toole Coldwell Banker McMahan

  7919 Mount Sterling Rd, Winchester, KY 40391
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  /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 $230,218

  Last Listing Agent Kimberly Brunson Hunter Real Estate

  646 Laura Dr, Winchester, KY 40391
• 

  

  /28

  Est $250,266 Not Listed For Sale

  116 Alabama St, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,626 Sq Ft
  • Built 1940

  116 Alabama St, Winchester, KY 40391

  Last Sold Summary

  • 8% Above List Price
  • $142/SF
  • 95 Days On Market

  • Last Sold Price $231,000
  • Mar 14, 2024

  Last Listing Agent Cheri Shaffer Keller Williams Commonwealth
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  /42

  $360,000

  • 4 Beds
  • 4.5 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 2 full and 1 half bath. Laundry hook-ups in all

  Jason Townsend Kentucky Residential Real Estate, LLC

  502 W Lexington Ave, Winchester, KY 40391
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  /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 $207,489

  Last Listing Agent Brenda Sipes Bridgewater Real Estate

  517 Hidden Hills Way, Winchester, KY 40391
• 

  

  /27

  Est $253,655 Not Listed For Sale

  335 S Main St, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,968 Sq Ft
  • Built 1920

  335 S Main St, Winchester, KY 40391

  Last Sold Summary

  • 2% Above List Price
  • $127/SF
  • 41 Days On Market

  • Last Sold Price $249,500
  • Jul 19, 2024

  Last Listing Agent Shari Frasure Keller Williams Commonwealth
• 

  

  /59

  $274,900

  • 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 $227,370

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  313 Snowden Dr, Winchester, KY 40391
• 

  

  /35

  Est $232,391 Not Listed For Sale

  24 Hughes Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Built 2024

  24 Hughes Ave, Winchester, KY 40391

  Last Sold Summary

  • 22% Above List Price
  • $158/SF
  • 24 Days On Market

  • Last Sold Price $189,900
  • Jan 16, 2025

  Last Listing Agent Nena Honaker Tom Goebel & Company
• 

  

  /19

  $265,000

  • 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 $287,110

  Last Listing Agent Ryan O'Gara Real Broker, LLC

  602 Laura Dr, Winchester, KY 40391
• 

  

  /20

  Est $199,596 Not Listed For Sale

  38 Hughes Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 1940

  38 Hughes Ave, Winchester, KY 40391

  Last Sold Summary

  • 21% Above List Price
  • $123/SF
  • 8 Days On Market

  • Last Sold Price $165,000
  • May 22, 2023

  Last Listing Agent Destiny Darby Keller Williams Commonwealth
• 

  

  /54

  $719,900

  • 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
• 

  

  /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 $587,249

  Last Listing Agent Beckie Moore Bluegrass Properties Group

  304 Winterberry Dr, Winchester, KY 40391
• 

  

  /41

  Est $239,661 Not Listed For Sale

  254 S Highland St, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 3,395 Sq Ft
  • Built 1935

  254 S Highland St, Winchester, KY 40391

  Last Sold Summary

  • 20% Above List Price
  • $59/SF
  • 10 Days On Market

  • Last Sold Price $200,000
  • Apr 30, 2024

  Last Listing Agent Michelle Blackburn RE/MAX
• 

  

  /33

  $209,900 Pending

  • 3 Beds
  • 1 Bath
  • 1,050 Sq Ft

  59 Holiday Rd, Winchester, KY 40391

  Don't Wait - this home is priced to Sell! All one level brick ranch features 3 Bedrooms, 1-bath. Newer updates include interior paint and laminate flooring giving the home a clean modern feel. The living spaces are filled with natural light, making the home feel warm and inviting. Step out to a spacious deck and large backyard - great for entertaining or just enjoying the outdoor space. Need

  Kathy Burton Coldwell Banker McMahan

  59 Holiday 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 $198,967

  Last Listing Agent Samantha Gray National Real Estate

  23 Hillcrest Dr, Winchester, KY 40391
• 

  

  /24

  Est $195,618 Not Listed For Sale

  54 Winn Ave, Winchester, KY 40391

  • 5 Beds
  • 2 Baths
  • 1,530 Sq Ft
  • Built 1940

  54 Winn Ave, Winchester, KY 40391

  Last Sold Summary

  • 9% Above List Price
  • $118/SF
  • 90 Days On Market

  • Last Sold Price $180,000
  • Oct 01, 2024

  Last Listing Agent Lukas Owens The Brokerage
• 

  /2

  $100,000

  • 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
• 

  

  /18

  $246,500 Sold May 16, 2025

  6278 Irvine Rd, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,176 Sq Ft
  • Built 1978

  Last Sold Summary

  • 7% Below List Price
  • $210/SF
  • 35 Days On Market

  Current Estimated Value $271,143

  Last Listing Agent Angela Yonts EXP Realty, LLC

  6278 Irvine Rd, Winchester, KY 40391
• 

  

  /33

  Est $249,308 Not Listed For Sale

  144 E Broadway St, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,544 Sq Ft
  • Built 1930

  144 E Broadway St, Winchester, KY 40391

  Last Sold Summary

  • 22% Above List Price
  • $81/SF
  • 119 Days On Market

  • Last Sold Price $205,000
  • Jan 19, 2024

  Last Listing Agent Thomas Harper Tom Harper and Associates
• 

  

  /23

  $175,000

  • 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
• 

  

  /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 $221,677

  Last Listing Agent Tyler I Back The Brokerage

  521 Acadia Way, Winchester, KY 40391
• 

  

  /22

  Est $222,473 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

  • 18% Above List Price
  • $144/SF
  • 143 Days On Market

  • Last Sold Price $188,000
  • Mar 31, 2025

  Last Listing Agent W Tyce McCullough Rector Hayden Realtors
• 

  /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

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