Winchester, KY Homes

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  /26

  Est $199,494 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

  • 38% Above List Price
  • $85/SF
  • 39 Days On Market

  • Last Sold Price $145,000
  • Jul 25, 2024

  Last Listing Agent Michelle Blackburn RE/MAX
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  /62

  $308,500 Pending

  • 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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  /38

  $599,500 Sold Sep 08, 2025

  102 Bella Shae Way, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,204 Sq Ft
  • Built 2025

  Last Sold Summary

  • $272/SF
  • 72 Days On Market

  Current Estimated Value $595,217

  Last Listing Agent Shane Underwood Keller Williams Commonwealth

  102 Bella Shae Way, Winchester, KY 40391
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  /11

  Est $129,167 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

  • 17% Above List Price
  • $143/SF
  • 18 Days On Market

  • Last Sold Price $110,000
  • Nov 17, 2023

  Last Listing Agent Michelle Newman Team Pannell Real Estate
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  /31

  $479,000

  • 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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  /34

  $333,900 Sold Jul 28, 2025

  366 Hanover Dr, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,162 Sq Ft
  • Built 2001

  Last Sold Summary

  • $154/SF
  • 2 Days On Market

  Current Estimated Value $337,731

  Last Listing Agent Melissa Brown Keller Williams Legacy Group

  366 Hanover Dr, Winchester, KY 40391
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  /25

  Est $170,780 Not Listed For Sale

  15 Madison Ave, Winchester, KY 40391

  • 2 Beds
  • 1.5 Baths
  • 960 Sq Ft
  • Built 1996

  15 Madison Ave, Winchester, KY 40391

  Last Sold Summary

  • 15% Above List Price
  • $155/SF
  • 1 Day On Market

  • Last Sold Price $149,000
  • May 22, 2023

  Last Listing Agent Tyanne Whitworth RE/MAX
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  /2

  $78,500

  • Land
  • 9,600 Sq Ft
  • $356,171 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
• 

  $100,000 Sold Feb 20, 2026

  17 Waveland Ave, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,061 Sq Ft
  • Built 1950

  Last Sold Summary

  • 9% Below List Price
  • $94/SF
  • 4 Days On Market

  Current Estimated Value $140,984

  Last Listing Agent Darrell Lewis DIY Realty Flat Fee MLS

  17 Waveland Ave, Winchester, KY 40391
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  /20

  Est $147,762 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

  • 100% Above List Price
  • $42/SF
  • 0 Days On Market

  • Last Sold Price $74,000
  • Jun 20, 2024

  Last Listing Agent Whitney Ensor Ensor Real Estate, LLC
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  /43

  $450,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 3,444 Sq Ft

  222 Ashton Oak Way, Winchester, KY 40391

  World class Residence, this magnificent home is now available, built without compromise the home reflects the very best, all brick, electric firepalce in the living room, basement partial finished with 2 car garage and storage room, This american classic has 3 bedrooms, 2 full baths, 1/2 bath, kitchen is better than great, you must call today!

  Mila Ensor Ensor Real Estate, LLC

  222 Ashton Oak Way, Winchester, KY 40391
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  /37

  $220,000 Sold Sep 23, 2025

  213 Blair Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,025 Sq Ft
  • Built 1979

  Last Sold Summary

  • 2% Below List Price
  • $215/SF
  • 4 Days On Market

  Current Estimated Value $217,583

  Last Listing Agent Elizabeth Hodge Lifstyl Real Estate

  213 Blair Ave, Winchester, KY 40391
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  /16

  Est $177,841 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

  • 35% Above List Price
  • $101/SF
  • 0 Days On Market

  • Last Sold Price $131,723
  • Aug 31, 2023

  Last Listing Agent Roscoe Riley Blu Horizon Real Estate
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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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  /2

  $110,000 Sold May 13, 2025

  140 Duclair Dr, Winchester, KY 40391

  • Land
  • 18,295 Sq Ft
  • $261,905 per Acre

  Last Sold Summary

  • 900 Days On Market

  Last Listing Agent John Wilson Bluegrass Properties Group

  140 Duclair Dr, Winchester, KY 40391
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  /74

  Est $566,687 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

  • 4% Below List Price
  • $201/SF
  • 3 Days On Market

  • Last Sold Price $590,000
  • Jul 19, 2024

  Last Listing Agent Janna Chalfant Smith United Real Estate Bluegrass
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  /2

  $224,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft

  11 Shelley Dr, Winchester, KY 40391

  Remodeled 3 bed 2 full bath, all-brick ranch in a quiet neighborhood. This well-maintained ranch on a full, unfinished, walk-out basement has been beautifully remodeled and is move-in-ready. Huge 25x25 detached garage

  Mark Wallace Transactionbroker.com

  11 Shelley Dr, Winchester, KY 40391
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  /44

  $515,000 Sold May 19, 2025

  31 Bonnie Brook Ln, Winchester, KY 40391

  • 5 Beds
  • 3.5 Baths
  • 4,091 Sq Ft
  • Built 1958

  Last Sold Summary

  • 10% Below List Price
  • $126/SF
  • 294 Days On Market

  Current Estimated Value $559,000

  Last Listing Agent Kelly Nisbet Coldwell Banker McMahan

  31 Bonnie Brook Ln, Winchester, KY 40391
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  /43

  Est $262,247 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

  • 10% Above List Price
  • $119/SF
  • 28 Days On Market

  • Last Sold Price $238,500
  • Nov 30, 2023

  Last Listing Agent Janna Chalfant Smith United Real Estate Bluegrass
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  /21

  $259,900

  • 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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  /14

  $200,000 Sold Sep 19, 2025

  9711 Ironworks Rd, Winchester, KY 40391

  Last Sold Summary

  • 11% Below List Price
  • 19 Days On Market

  Last Listing Agent Jessica Maloney Denniston Realty

  9711 Ironworks Rd, Winchester, KY 40391
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  /38

  Est $247,367 Not Listed For Sale

  377 Crescent Ave, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,540 Sq Ft
  • Built 1940

  377 Crescent Ave, Winchester, KY 40391

  Last Sold Summary

  • 12% Above List Price
  • $143/SF
  • 0 Days On Market

  • Last Sold Price $219,900
  • Feb 02, 2024

  Last Listing Agent Lori Tolson Lifstyl Real Estate
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  /6

  $49,500

  • Land
  • 42,688 Sq Ft
  • $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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  /75

  $490,000 Sold Sep 26, 2025

  497 Goose Creek Rd, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 2,972 Sq Ft
  • Built 1993

  Last Sold Summary

  • 1% Below List Price
  • $165/SF
  • 2 Days On Market

  Current Estimated Value $465,493

  Last Listing Agent O Eve Stern Threshold Real Estate Services

  497 Goose Creek Rd, Winchester, KY 40391
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  /27

  Est $210,078 Not Listed For Sale

  374 S Main St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 972 Sq Ft
  • Built 1940

  374 S Main St, Winchester, KY 40391

  Last Sold Summary

  • 5% Above List Price
  • $205/SF
  • 206 Days On Market

  • Last Sold Price $199,500
  • Apr 30, 2025

  Last Listing Agent Mila Ensor Ensor Real Estate, LLC
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  /34

  $249,000

  • Land
  • 6.08 Acres
  • $40,954 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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  /25

  $287,000 Sold Aug 20, 2025

  220 Mcdowell Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,402 Sq Ft
  • Built 1987

  Last Sold Summary

  • 12% Below List Price
  • $205/SF
  • 36 Days On Market

  Current Estimated Value $297,768

  Last Listing Agent Alyssa M Boley Coldwell Banker McMahan

  220 Mcdowell Dr, Winchester, KY 40391
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  /27

  Est $377,569 Not Listed For Sale

  200 Moundale Ave, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 3,428 Sq Ft
  • Built 1960

  200 Moundale Ave, Winchester, KY 40391

  Last Sold Summary

  • 8% Above List Price
  • $102/SF
  • 84 Days On Market

  • Last Sold Price $350,000
  • Sep 16, 2024

  Last Listing Agent Kelly Nisbet Coldwell Banker McMahan
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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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  /33

  $240,000 Sold Sep 10, 2025

  752 Wayland Dr, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,472 Sq Ft
  • Built 1969

  Last Sold Summary

  • 11% Below List Price
  • $97/SF
  • 18 Days On Market

  Current Estimated Value $258,178

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate

  752 Wayland Dr, Winchester, KY 40391
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  /28

  Est $235,728 Not Listed For Sale

  358 Crescent Ave, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,764 Sq Ft
  • Built 1950

  358 Crescent Ave, Winchester, KY 40391

  Last Sold Summary

  • 5% Above List Price
  • $127/SF
  • 2 Days On Market

  • Last Sold Price $224,900
  • Dec 06, 2024

  Last Listing Agent Lucy Martin Jenkins United Real Estate Bluegrass
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  /2

  $600,000

  • Land
  • 6.13 Acres
  • $97,879 per Acre

  722 Colby Rd Unit 2, Winchester, KY 40391

  Discover an exceptional opportunity for retail investment in the thriving Winchester area. Zoned B-4, this versatile property offers a wide array of possibilities for retail development, providing a strategic location for businesses seeking to establish a prominent presence. With its prime zoning and desirable position within the Winchester area, this property presents a compelling prospect for

  Cheryl Johnston CMI Properties

  722 Colby Rd Unit 2, Winchester, KY 40391
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  /24

  $275,000 Sold Mar 02, 2026

  434 Paisley Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,678 Sq Ft
  • Built 2012

  Last Sold Summary

  • $164/SF
  • 1 Day On Market

  Current Estimated Value $270,493

  Last Listing Agent Joshua Davis The Agency

  434 Paisley Ct, Winchester, KY 40391
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  /77

  Est $288,512 Not Listed For Sale

  328 S Main St, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,709 Sq Ft
  • Built 1900

  328 S Main St, Winchester, KY 40391

  Last Sold Summary

  • 20% Above List Price
  • $89/SF
  • 26 Days On Market

  • Last Sold Price $240,000
  • Dec 15, 2023

  Last Listing Agent Josh Wood Freedom Realty & Property Management
• 

  

  /31

  $189,000

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft

  5434 Pine Ridge Rd, Winchester, KY 40391

  Jim Woodrum RE/MAX Creative, Winchester

  5434 Pine Ridge Rd, Winchester, KY 40391
• 

  

  /27

  $185,000 Sold Mar 23, 2026

  616 Boone Ave, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,223 Sq Ft
  • Built 1955

  Last Sold Summary

  • 7% Below List Price
  • $151/SF
  • 16 Days On Market

  Current Estimated Value $197,049

  Last Listing Agent Garnett Davis Tom Goebel & Company

  616 Boone Ave, Winchester, KY 40391
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  /57

  Est $359,255 Not Listed For Sale

  286 S Main St, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 3,689 Sq Ft
  • Built 1910

  286 S Main St, Winchester, KY 40391

  Last Sold Summary

  • 6% Above List Price
  • $92/SF
  • 9 Days On Market

  • Last Sold Price $340,000
  • Oct 18, 2024

  Last Listing Agent Kelly Nisbet Coldwell Banker McMahan
• 

  

  /34

  $875,000 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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  /29

  $262,500 Sold Feb 18, 2026

  410 Wellington Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,192 Sq Ft
  • Built 2007

  Last Sold Summary

  • 2% Below List Price
  • $220/SF
  • 69 Days On Market

  Current Estimated Value $259,652

  Last Listing Agent Monica Marcum Century 21 Pinnacle

  410 Wellington Way, Winchester, KY 40391
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  /34

  Est $274,835 Not Listed For Sale

  312 S Main St, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 2,355 Sq Ft
  • Built 1920

  312 S Main St, Winchester, KY 40391

  Last Sold Summary

  • 4% Above List Price
  • $113/SF
  • 1 Day On Market

  • Last Sold Price $265,000
  • Jun 25, 2024

  Last Listing Agent Susan Baldwin Threshold Real Estate Services

Showing Results 521 - 560, Page 14 of 18