Homes in ZIP Code 40391

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  /20

  Est $234,447 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

  • 17% Above List Price
  • $134/SF
  • 9 Days On Market

  Last Sold Price $200,000

  Last Listing Agent Cheri Shaffer Keller Williams Commonwealth
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  /8

  $175,000

  • Land
  • 6.59 Acres
  • $26,555 per Acre

  990 Craig Crossing Rd, Winchester, KY 40391

  Lot # 13 contains 6.588 acres of gently rolling land perfect for your new home. This is a rare opportunity to own a piece of western Clark County real estate in the sought-after McClure Road area. Thoroughbred Estates is Winchester's newest upscale development containing 33 lots from 2 acres to nearly 7 acres. Lots are located just minutes from Winchester and Lexington.

  Keith Wilson Coldwell Banker McMahan

  990 Craig Crossing Rd, Winchester, KY 40391
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  /60

  $545,000 Sold Oct 31, 2025

  445 Lynnway Dr, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 3,649 Sq Ft
  • Built 1993

  Last Sold Summary

  • $149/SF
  • 4 Days On Market

  Current Estimated Value $546,710

  Last Listing Agent Janna Chalfant Smith United Real Estate Bluegrass

  445 Lynnway Dr, Winchester, KY 40391
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  /79

  Est $198,116 Not Listed For Sale

  205 French Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 946 Sq Ft
  • Built 1959

  205 French Ave, Winchester, KY 40391

  Last Sold Summary

  • 2% Above List Price
  • $206/SF
  • 319 Days On Market

  Last Sold Price $195,000

  Last Listing Agent Greg Wood Freedom Realty & Property Management
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  /62

  $319,500

  • 8 Beds
  • 5 Baths
  • 3,637 Sq Ft

  144 Holly Ave, Winchester, KY 40391

  Excellent investment opportunity featuring two income-producing buildings on one lot, offered together as a package deal. This unique multifamily property includes a triplex and a separate duplex, making it ideal for investors looking to expand their portfolio with multiple units in one purchase. The triplex (Building A) consists of three units: Unit A-1: 2 bedrooms, 1 bathroom Unit A-2: 1

  Shane Underwood Keller Williams Commonwealth

  144 Holly Ave, Winchester, KY 40391
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  /27

  $380,000 Sold Nov 10, 2025

  5705 Mount Sterling Rd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,980 Sq Ft
  • Built 1971

  Last Sold Summary

  • 5% Below List Price
  • $128/SF
  • 50 Days On Market

  Current Estimated Value $378,028

  Last Listing Agent Dale Hatton Dream Maker Realty, LLC

  5705 Mount Sterling Rd, Winchester, KY 40391
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  /24

  Est $201,199 Not Listed For Sale

  5 Kentucky St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,634 Sq Ft
  • Built 1930

  5 Kentucky St, Winchester, KY 40391

  Last Sold Summary

  • 19% Above List Price
  • $103/SF
  • 1 Day On Market

  Last Sold Price $169,000

  Last Listing Agent Melissa Brown Keller Williams Legacy Group
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  /31

  $505,000

  • 8 Beds
  • 4 Baths
  • 5,058 Sq Ft

  265 S Highland St, Winchester, KY 40391

  Great investment opportunity in downtown Winchester! This spacious quadplex has been updated throughout and offers a true turn-key multi-family property. Each unit features two bedrooms, one bathroom, a full kitchen, and its own private laundry area. Utilities are separately metered, allowing tenants to handle their own services and helping keep operating costs manageable. With a total of 8

  J Corey Griffo RE/MAX Elite Lexington

  265 S Highland St, 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
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  /23

  Est $181,969 Not Listed For Sale

  11 Kentucky St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,708 Sq Ft
  • Built 1920

  11 Kentucky St, Winchester, KY 40391

  Last Sold Summary

  • 70% Above List Price
  • $63/SF
  • 9 Days On Market

  Last Sold Price $107,000

  Last Listing Agent Darrell Lewis DIY Flat Fee.com
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  /2

  $78,500

  • Land
  • 0.22 Acre
  • $356,818 per Acre

  Lot 5 Plantations Dr, Winchester, KY 40391

  NOW SELLING SFH Buildable Lots of PHASE ONE: 12 Buildable Lots (minimum lot is 9600+ sqft) of PHASE ONE of Deerlawn's Development located at 2395 Paris Rd (Parent Listing). Earmarked as Winchester, Ky's most anticipated residential development consisting of an ambitious 274+-acre expansion formerly known as the well-established Royal Oaks/Plantation neighborhoods, Phase One has 12 lots ready for

  Melia Hord Keller Williams Legacy Group

  Lot 5 Plantations Dr, Winchester, KY 40391
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  /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 $377,734

  Last Listing Agent Jordan James Lifstyl Real Estate

  512 Boone Ave, Winchester, KY 40391
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  /24

  Est $199,866 Not Listed For Sale

  21 Kentucky St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,340 Sq Ft
  • Built 1920

  21 Kentucky St, Winchester, KY 40391

  Last Sold Summary

  • 5% Above List Price
  • $141/SF
  • 80 Days On Market

  Last Sold Price $189,500

  Last Listing Agent Anthony Gigilo ListWithFreedom.com
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  /36

  $199,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft

  58 Hughes Ave, Winchester, KY 40391

  Nice remodeled 3 bedroom and 2 bath home...Ranch on a basement...2 bed 1 bath upstairs and Basement has another living area with 1 bedroom and 1 bath. Fresh paint , new lights, newer hvac and newer windows. Kitchen has been updated with granite, appliances and fresh paint....agent owner

  E Anthony Phillips RE/MAX Creative Realty

  58 Hughes Ave, Winchester, KY 40391
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  /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 $394,855

  Last Listing Agent ROBIN TRIMBLE HomeFirst Real Estate

  399 Stonecrest Rd, Winchester, KY 40391
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  /18

  Est $120,102 Not Listed For Sale

  129 Kentucky St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,080 Sq Ft
  • Built 1940

  129 Kentucky St, Winchester, KY 40391

  Last Sold Summary

  • 60% Above List Price
  • $69/SF
  • 46 Days On Market

  Last Sold Price $75,000

  Last Listing Agent Austin Polley The Polley Group
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  /12

  $269,900

  • 4 Beds
  • 1 Bath
  • 1,610 Sq Ft

  120 Windsor Dr, Winchester, KY 40391

  Welcome home to this cozy brick charmer in the desirable Belair Subdivision of Winchester, KY! This inviting 4 bedroom, 1 bath home offers comfortable living with a warm electric fireplace perfect for relaxing evenings. The spacious layout provides flexibility for family, guests, or a home office. Step outside to a fully fenced backyard ideal for pets, play, or enjoying quiet mornings with your

  Team Farthing - Mitch Farthing Southern Legacy Realty

  120 Windsor Dr, 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 $622,074

  Last Listing Agent Terri McGraw FC Tucker Bluegrass

  315 The Woods Ln, Winchester, KY 40391
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  /15

  Est $194,856 Not Listed For Sale

  20 Elizabeth St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,258 Sq Ft
  • Built 1940

  20 Elizabeth St, Winchester, KY 40391

  Last Sold Summary

  • 1% Above List Price
  • $153/SF
  • 7 Days On Market

  Last Sold Price $192,588

  Last Listing Agent Jessica Moreno SimpliHOM
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  /29

  $389,900

  • 8 Beds
  • 8 Baths
  • 4,000 Sq Ft

  17 W Lexington Ave, Winchester, KY 40391

  Investment Opportunity in the Heart of Downtown Winchester! Discover 17 W. Lexington Ave, a converted commercial building now featuring 8 studio/one-bedroom apartments. Each unit includes a full kitchen and private bath, offering the perfect blend of comfort and convenience for tenants. This multifamily property is ideally situated in historic downtown Winchester, within walking distance to

  Joshua Lynch The Brokerage

  17 W Lexington Ave, Winchester, KY 40391
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  /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 $196,139

  Last Listing Agent Dylan Justice GSP Homes

  357 E Washington St, Winchester, KY 40391
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  /17

  Est $217,736 Not Listed For Sale

  102 Kentucky St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,734 Sq Ft
  • Built 1940

  102 Kentucky St, Winchester, KY 40391

  Last Sold Summary

  • 1% Above List Price
  • $124/SF
  • 41 Days On Market

  Last Sold Price $215,000

  Last Listing Agent Holly Spradlin KY Realty Co
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  /6

  $49,500

  • Land
  • 0.98 Acre
  • $50,510 per Acre

  204 Wigeon Ct, Winchester, KY 40391

  Choose your preferred builder to construct your dream home in Mallard Place. Located in a quiet cul-de-sac at the rear of the subdivision. Only a 20 minute drive to Hamburg/Lexington and only a 5 minute drive to the Winchester Bypass. Enjoy the serenity of living in a private setting AND the convenience of being close to schools, shopping and I-64 and I-75.

  Jim Woodrum RE/MAX Creative, Winchester

  204 Wigeon Ct, 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 $188,332

  Last Listing Agent Brenda Sipes Bridgewater Real Estate

  517 Hidden Hills Way, Winchester, KY 40391
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  /16

  Est $339,976 Not Listed For Sale

  122 French Ave, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 4,176 Sq Ft
  • Built 1920

  122 French Ave, Winchester, KY 40391

  Last Sold Summary

  • 13% Above List Price
  • $72/SF
  • 4 Days On Market

  Last Sold Price $300,000

  Last Listing Agent Brenda Sipes Bridgewater Real Estate
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  /34

  $260,000

  • Land
  • 6.08 Acres
  • $42,763 per Acre

  190 Privacy Ln, Winchester, KY 40391

  6.08 acres settled in Clark County with access from both Privacy Ln and Little Stoner Rd. This property boasts a 30x56 with 10 foot wall Kentucky Steel Truss building with concrete floors, gas and wood burning heat, full bath, and a car lift. Additionally, there is a barn with a 3 bay shed attached.

  Jason Joseph Keller Williams Commonwealth

  190 Privacy Ln, Winchester, KY 40391
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  /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 $225,405

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  313 Snowden Dr, Winchester, KY 40391
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  /31

  Est $198,523 Not Listed For Sale

  134 Central Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,946 Sq Ft
  • Built 1930

  134 Central Ave, Winchester, KY 40391

  Last Sold Summary

  • 42% Above List Price
  • $72/SF
  • 1 Day On Market

  Last Sold Price $140,000

  Last Listing Agent Mila Ensor Ensor Real Estate, LLC
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  /3

  $395,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,855 Sq Ft

  205 Evergreen Dr, Winchester, KY 40391

  Introducing The Mulberry floor plan - a beautifully designed proposed construction home in the scenic Locust Hill Acres community. This open-concept floor plan offers the perfect blend of comfort and functionality with 3 bedrooms, 2 full bathrooms, and thoughtful living spaces throughout.The spacious primary suite features a large walk-in closet and a private ensuite bath, providing a

  Rex Hall United Real Estate Bluegrass

  205 Evergreen Dr, Winchester, KY 40391
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  /53

  $80,000 Sold Apr 30, 2025

  307 Jackson St, Winchester, KY 40391

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

  Last Sold Summary

  • 33% Below List Price
  • $49/SF
  • 67 Days On Market

  Current Estimated Value $89,829

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  307 Jackson St, Winchester, KY 40391
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  /19

  Est $205,668 Not Listed For Sale

  130 Central Ave, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,322 Sq Ft
  • Built 1930

  130 Central Ave, Winchester, KY 40391

  Last Sold Summary

  • 11% Above List Price
  • $140/SF
  • 1 Day On Market

  Last Sold Price $185,000

  Last Listing Agent Lukas Owens The Brokerage
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  /61

  $925,000 New Construction

  • 5 Beds
  • 3.5 Baths
  • 2,842 Sq Ft

  1150 Craig Crossing, Winchester, KY 40391

  Stunning new construction offering 5 bedrooms, 3.5 bathrooms, sitting on roughly 2.5 serene acres. This home is surrounded by picturesque farmland and panoramic views. 4 bedrooms are located on the main level for ultimate convenience. Offering the perfect blend of space, style, and serenity. Features include open concept layout, spacious kitchen with kitchen island, granite counter tops, hidden

  Stephanie Hacker Kentucky Residential Real Estate, LLC

  1150 Craig Crossing, Winchester, KY 40391
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  /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 $287,760

  Last Listing Agent Ryan O'Gara Real Broker, LLC

  602 Laura Dr, Winchester, KY 40391
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  /8

  Est $244,324 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

  • 8% Above List Price
  • $167/SF
  • 9 Days On Market

  Last Sold Price $227,000

  Last Listing Agent Andrew Fugitt Coldwell Banker McMahan
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  /24

  $286,000 Pending

  • 12 Beds
  • 4 Baths
  • 4,010 Sq Ft

  149 Winn Ave, Winchester, KY 40391

  Welcome to this quad plex income producing property. It is a large lot and the property sits back on the lot away from the road. There are 4 units, each with 3 beds and 1 bath. The whole building has a total of bedrooms of 12 beds and 4 baths. Each unit has its own kitchen. The pictures are of the only vacant unit on the bottom left. The two lower units rent for $950 and $925. The upper units

  Libby VanMeter Marshall Lane Real Estate - Lexington

  149 Winn Ave, Winchester, KY 40391
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  /2

  $401,500 Sold May 15, 2025

  Unlisted Address

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft
  • Built 1998

  Last Sold Summary

  • $201/SF

  Current Estimated Value $409,226

  Last Listing Agent Null Non-Member Non-Member Office

  Unlisted Address
• 

  

  /23

  Est $196,247 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

  • 23% Above List Price
  • $92/SF
  • 8 Days On Market

  Last Sold Price $160,000

  Last Listing Agent Wayne Elkins RE/MAX
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  /39

  $429,900

  • 3 Beds
  • 2.5 Baths
  • 2,258 Sq Ft

  233 Cunningham Ln, Winchester, KY 40391

  Welcome to 233 Cunningham Lane in Winchester, KY — a versatile mini farm offering 6.7 acres, multiple outbuildings, and a functional one-level ranch floor plan designed for comfort and flexibility. Conveniently located less than two miles from the Mountain Parkway, this property combines rural space with easy accessibility for commuting and everyday travel. The ranch-style home features 3

  Amanda Marcum Berkshire Hathaway HomeServices Foster Realtors

  233 Cunningham Ln, 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 $592,964

  Last Listing Agent Beckie Moore Bluegrass Properties Group

  304 Winterberry Dr, Winchester, KY 40391
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  /48

  Est $247,668 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

  Last Listing Agent Libby VanMeter Marshall Lane Real Estate - Lexington

Showing Results 441 - 480, Page 12 of 18