Winchester, KY Homes

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  /41

  Est $269,529 Not Listed For Sale

  21 Beckner St, Winchester, KY 40391

  • 6 Beds
  • 3.5 Baths
  • 3,072 Sq Ft
  • Built 1940

  21 Beckner St, Winchester, KY 40391

  Last Sold Summary

  • 17% Above List Price
  • $75/SF
  • 17 Days On Market

  • Last Sold Price $230,000
  • Aug 01, 2024

  Last Listing Agent Shane Underwood Keller Williams Commonwealth
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  /26

  $215,000 Pending

  • 2 Beds
  • 1.5 Baths
  • 1,120 Sq Ft

  271 April Way, Winchester, KY 40391

  This charming 2 - story townhouse is in a prime location.. Welcome to this beautifully maintained 2 bedroom, 1.5 bath townhouse offering the perfect blend of comfort, style and convenience. Spread over two spacious levels, this home features an inviting living area, a modern kitchen with ample cabinetry and a cozy dining space-perfect for every day living or entertaining guests. Upstairs,

  Kimberly Fugate Keller Williams Commonwealth

  271 April Way, Winchester, KY 40391
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  /32

  $360,000 Sold Aug 14, 2025

  418 Skylark Dr, Winchester, KY 40391

  • 5 Beds
  • 2.5 Baths
  • 2,746 Sq Ft
  • Built 1990

  Last Sold Summary

  • 3% Above List Price
  • $131/SF
  • 12 Days On Market

  Current Estimated Value $351,348

  Last Listing Agent Kymberly McCreary EXP Realty, LLC

  418 Skylark Dr, Winchester, KY 40391
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  /51

  Est $387,192 Not Listed For Sale

  200 College St, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 3,227 Sq Ft
  • Built 1887

  200 College St, Winchester, KY 40391

  Last Sold Summary

  • 19% Above List Price
  • $101/SF
  • 137 Days On Market

  • Last Sold Price $325,000
  • Jul 14, 2023

  Last Listing Agent Amy Diamond ERA Select Real Estate
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  /31

  $204,900 Pending

  • 3 Beds
  • 1 Bath
  • 1,290 Sq Ft

  60 Hiawatha Trail, Winchester, KY 40391

  Updated, affordable, and ready for you! This 3-bedroom, 1-bath home offers approximately 1,300 square feet of comfortable living space with tasteful updates that make it easy to move right in. The layout provides a welcoming feel with bright living areas and an updated kitchen and bath. Downstairs you have a possible 4th bedroom or office space. Conveniently located in Winchester close to

  Christina Bucher Keller Williams Legacy Group

  60 Hiawatha Trail, Winchester, KY 40391
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  /57

  $775,000 Sold Mar 02, 2026

  1700 Cabin Creek Rd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,695 Sq Ft
  • Built 1994

  Last Sold Summary

  • $288/SF
  • 33 Days On Market

  Current Estimated Value $759,500

  Last Listing Agent Alysia Niva Century 21 Advantage Realty - Georgetown

  1700 Cabin Creek Rd, Winchester, KY 40391
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  /12

  Est $247,495 Not Listed For Sale

  217 College St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,650 Sq Ft
  • Built 1940

  217 College St, Winchester, KY 40391

  Last Sold Summary

  • 4% Above List Price
  • $144/SF
  • 72 Days On Market

  • Last Sold Price $237,500
  • Oct 08, 2024

  Last Listing Agent Angie Conley Dixon Dixon Properties
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  /4

  $64,900 Pending

  • Land
  • 22,651 Sq Ft
  • $124,808 per Acre

  101 Royal Oak Dr, Winchester, KY 40391

  A Unique Opportunity to Build your Dream Home in the Estate Section of Royal Oaks in Clark County. Situated on..52 acres of land and Conveniently located off Exit 96 on I-64, with close proximity to the Industrial Park, Shopping, Dining and downtown Winchester. Call listing agent for additional details and information on the few lots left to build on in this subdivision!

  Melia Hord Keller Williams Legacy Group

  101 Royal Oak Dr, Winchester, KY 40391
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  /79

  $204,000 Sold Oct 30, 2025

  133 S Burns Ave, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 3,295 Sq Ft
  • Built 1915

  Last Sold Summary

  • 18% Below List Price
  • $62/SF
  • 20 Days On Market

  Current Estimated Value $213,849

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  133 S Burns Ave, Winchester, KY 40391
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  /54

  Est $357,674 Not Listed For Sale

  308 W Hickman St, Winchester, KY 40391

  • 5 Beds
  • 3 Baths
  • 2,681 Sq Ft
  • Built 1940

  308 W Hickman St, Winchester, KY 40391

  Last Sold Summary

  • 2% Above List Price
  • $131/SF
  • 136 Days On Market

  • Last Sold Price $350,000
  • Apr 04, 2025

  Last Listing Agent Dalis Alvarez GSP Homes
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  /4

  $10,000

  • Land
  • 7,274 Sq Ft
  • $59,880 per Acre

  117 4th St, Winchester, KY 40391

  Discover the potential of this spacious 0.17-acre residential property nestled in a neighborhood community on clear and level vacant lot located in a Cul-de-sac of Lincoln Park Subdivision. This could be an investment opportunity as well, for ideal savvy investors looking to diversify your portfolio this property would be perfect for building a custom home, holding for future value, or develop

  Anita McDermott Keller Williams Bluegrass Realty

  117 4th St, Winchester, KY 40391
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  /28

  $246,000 Sold Nov 06, 2025

  204 Moss Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,430 Sq Ft
  • Built 1998

  Last Sold Summary

  • 3% Above List Price
  • $172/SF
  • 1 Day On Market

  Current Estimated Value $247,692

  Last Listing Agent Brooke Martin RO&CO Real Estate

  204 Moss Ct, Winchester, KY 40391
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  /27

  Est $301,425 Not Listed For Sale

  118 Olde Potomac Ave, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 3,000 Sq Ft
  • Built 1935

  118 Olde Potomac Ave, Winchester, KY 40391

  Last Sold Summary

  • 6% Above List Price
  • $95/SF
  • 6 Days On Market

  • Last Sold Price $285,000
  • Jun 30, 2023

  Last Listing Agent Cheri Shaffer Keller Williams Commonwealth
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  /7

  $150,000

  • Land
  • 4.21 Acres
  • $35,629 per Acre

  1030 Craig Crossing Rd, Winchester, KY 40391

  Lot # 14 contains 4.21 acres of gently rolling land with small stream 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

  1030 Craig Crossing Rd, Winchester, KY 40391
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  /58

  $232,500 Sold Jul 12, 2025

  114 Holiday Rd, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,161 Sq Ft
  • Built 1980

  Last Sold Summary

  • 7% Below List Price
  • $200/SF
  • 235 Days On Market

  Current Estimated Value $231,424

  Last Listing Agent Karen Smith Emmerich Muzic Realty

  114 Holiday Rd, Winchester, KY 40391
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  /86

  Est $297,570 Not Listed For Sale

  112 Olde Potomac Ave, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 3,220 Sq Ft
  • Built 1935

  112 Olde Potomac Ave, Winchester, KY 40391

  Last Sold Summary

  • 1% Above List Price
  • $91/SF
  • 2 Days On Market

  • Last Sold Price $294,000
  • Sep 17, 2024

  Last Listing Agent Josh Wood Freedom Realty & Property Management
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  /14

  $154,900

  • Land
  • 2.66 Acres
  • $58,277 per Acre

  590 Craig Crossing, Winchester, KY 40391

  Don't let this opportunity pass you by again. This prime lot in Thoroughbred Estates is back on the market due to Current owners change of plans. This lot is ready for your new home with a beautiful setting and located close to Winchester and Lexington in a new Luxury Subdivision. Watch the sun set each night from your rear deck or pool. Call today!!!

  Keith Wilson Coldwell Banker McMahan

  590 Craig Crossing, Winchester, KY 40391
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  /28

  $234,500 Sold Jul 29, 2025

  108 Sturbridge Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 2004

  Last Sold Summary

  • 4% Below List Price
  • $195/SF
  • 45 Days On Market

  Current Estimated Value $241,608

  Last Listing Agent Jason Szaks EXIT TOWN & COUNTRY REALTORS

  108 Sturbridge Ln, Winchester, KY 40391
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  /30

  Est $236,916 Not Listed For Sale

  302 W Lexington Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,939 Sq Ft
  • Built 1935

  302 W Lexington Ave, Winchester, KY 40391

  Last Sold Summary

  • 14% Above List Price
  • $107/SF
  • 16 Days On Market

  • Last Sold Price $207,500
  • May 09, 2024

  Last Listing Agent Heather Justice Rector Hayden Realtors
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  /2

  $78,500

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

  Lot 3 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 3 Plantations Dr, Winchester, KY 40391
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  /52

  $230,000 Sold Jan 20, 2026

  19 Cherokee Ct, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,134 Sq Ft
  • Built 1968

  Last Sold Summary

  • 2% Above List Price
  • $203/SF
  • 2 Days On Market

  Current Estimated Value $227,908

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  19 Cherokee Ct, Winchester, KY 40391
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  /11

  Est $244,465 Not Listed For Sale

  25 Hays St, Winchester, KY 40391

  • 5 Beds
  • 3.5 Baths
  • 2,830 Sq Ft
  • Built 1940

  25 Hays St, Winchester, KY 40391

  Last Sold Summary

  • 32% Above List Price
  • $65/SF
  • 33 Days On Market

  • Last Sold Price $185,000
  • Jan 17, 2025

  Last Listing Agent Chase Pennington Team Pannell Real Estate
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  /2

  $150,000

  • Land
  • 2.77 Acres
  • $54,074 per Acre

  3385 Colby Rd, Winchester, KY 40391

  Parcel 4 in the photos. This 2.774 acre lot is available on Colby Road just 1.5 miles from the Winchester Bypass. No building restrictions other than no manufactured housing and a paved driveway must be completed within a year of finishing a residence.

  Steve Adams Steven D Adams Real Estate Services, LLC

  3385 Colby Rd, Winchester, KY 40391
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  /22

  $334,327 Sold Jul 01, 2025

  136 Gibson Way, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 1,997 Sq Ft
  • Built 2024

  Last Sold Summary

  • $167/SF
  • 219 Days On Market

  Current Estimated Value $344,381

  Last Listing Agent Neshia Gaines Christies International Real Estate Bluegrass

  136 Gibson Way, Winchester, KY 40391
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  /34

  Est $198,115 Not Listed For Sale

  397 College St, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,655 Sq Ft
  • Built 1940

  397 College St, Winchester, KY 40391

  Last Sold Summary

  • 14% Above List Price
  • $105/SF
  • 44 Days On Market

  • Last Sold Price $174,000
  • Apr 25, 2025

  Last Listing Agent Josh Wood Freedom Realty & Property Management
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  /23

  $250,000

  • Land
  • 14.51 Acres
  • $17,228 per Acre

  3056 Irvine Rd, Winchester, KY 40391

  Discover the perfect blend of beauty, privacy, and opportunity with this stunning 14.511-acre tract on Irvine Road. Featuring gently rolling hills, this property offers multiple ideal building sites to bring your dream home to life, whether you're envisioning a modern farmhouse, barndominium, or private country retreat. A barn is already in place, adding immediate functionality for storage,

  Christa Joynt Keller Williams Commonwealth

  3056 Irvine Rd, Winchester, KY 40391
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  /37

  $275,000 Sold Sep 10, 2025

  279 Ascot Ave, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,247 Sq Ft
  • Built 2000

  Last Sold Summary

  • 8% Below List Price
  • $122/SF
  • 2 Days On Market

  Current Estimated Value $293,988

  Last Listing Agent Chase Pennington Team Pannell Real Estate

  279 Ascot Ave, Winchester, KY 40391
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  /25

  Not Listed For Sale

  410 W Lexington Ave, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 4,154 Sq Ft
  • Built 1945

  410 W Lexington Ave, Winchester, KY 40391

  Last Sold Summary

  • 173% Above List Price
  • $29/SF
  • 13 Days On Market

  • Last Sold Price $121,000
  • Nov 09, 2016

  Last Listing Agent Kristin Ray Lifstyl Real Estate
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  /3

  $700,000 New Construction

  • 3 Beds
  • 2 Baths
  • 2,400 Sq Ft

  415 Alexis Way, Winchester, KY 40391

  Introducing the Merango, a classic all-brick ranch home designed for both comfort and style. With stunning double front doors and a 2-car attached garage, this home offers incredible curb appeal and modern living. The spacious 3-bedroom, 2-bath layout features a split-bedroom design for added privacy, along with a dedicated study perfect for a home office. The open-concept kitchen is ideal for

  Shane Underwood Keller Williams Commonwealth

  415 Alexis Way, Winchester, KY 40391
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  /24

  $198,000 Sold Jul 18, 2025

  113 Colonial Park Dr, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,075 Sq Ft
  • Built 1983

  Last Sold Summary

  • 2% Above List Price
  • $184/SF
  • 0 Days On Market

  Current Estimated Value $207,663

  Last Listing Agent Janet Baldwin Kentucky Land and Home

  113 Colonial Park Dr, Winchester, KY 40391
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  /16

  Est $175,730 Not Listed For Sale

  227 W Broadway St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 2008

  227 W Broadway St, Winchester, KY 40391

  Last Sold Summary

  • 13% Above List Price
  • $111/SF
  • 51 Days On Market

  • Last Sold Price $155,000
  • Aug 09, 2023

  Last Listing Agent Donna Elder RE/MAX
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  /84

  $274,950

  • 4 Beds
  • 3 Baths
  • 2,112 Sq Ft

  115 Watercrest Cir, Winchester, KY 40391

  Stunning Home in One of the Area's Most Coveted Neighborhoods!Experience spacious living with 3 generous bedrooms and 2 full baths on the main level, designed for comfort and everyday convenience. The walkout basement offers even more space with a large bedroom and an additional full bath, ideal for guests, extended family, or a private retreat. What truly sets this home apart? The sellers are

  Darrell Tackett Dream Maker Realty, LLC

  115 Watercrest Cir, Winchester, KY 40391
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  /24

  $90,000 Sold Mar 23, 2026

  701 Williamsburg Dr, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 996 Sq Ft
  • Built 1971

  Last Sold Summary

  • 7% Below List Price
  • $90/SF
  • 2 Days On Market

  Current Estimated Value $97,713

  Last Listing Agent Shane Underwood Keller Williams Commonwealth

  701 Williamsburg Dr, Winchester, KY 40391
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  /6

  Est $94,337 Not Listed For Sale

  231 W Broadway St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,150 Sq Ft
  • Built 1945

  231 W Broadway St, Winchester, KY 40391

  Last Sold Summary

  • 372% Above List Price
  • $17/SF
  • 667 Days On Market

  • Last Sold Price $20,000
  • Mar 28, 2025

  Last Listing Agent Will Childers WTC Realty LLC
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  /30

  $175,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,260 Sq Ft

  432 Country Club Dr, Winchester, KY 40391

  Fully remodeled and move-in ready, this 2-bedroom, 2 full bathroom townhome offers approximately 1,260 square feet of updated living space in a convenient Winchester location. Recent renovations include new dimensional shingle roofing, updated windows and doors, new siding, and a newly built rear deck?perfect for enjoying the outdoors. Inside, the home features luxury vinyl flooring, fresh carpet

  Ryan Sigler Rector Hayden Realtors

  432 Country Club Dr, Winchester, KY 40391
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  /27

  $335,000 Sold Dec 18, 2025

  2198 Goshen Rd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,730 Sq Ft
  • Built 1997

  Last Sold Summary

  • 5% Above List Price
  • $194/SF
  • 31 Days On Market

  Current Estimated Value $335,602

  Last Listing Agent Jason Szaks EXIT TOWN & COUNTRY REALTORS

  2198 Goshen Rd, Winchester, KY 40391
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  /26

  Est $194,174 Not Listed For Sale

  235 W Broadway St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,440 Sq Ft
  • Built 1945

  235 W Broadway St, Winchester, KY 40391

  Last Sold Summary

  • 19% Above List Price
  • $113/SF
  • 35 Days On Market

  • Last Sold Price $163,000
  • Dec 27, 2024

  Last Listing Agent Nena Honaker Tom Goebel & Company
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  /59

  $695,000 Pending

  • 3 Beds
  • 4 Baths
  • 4,008 Sq Ft

  1775 Irvine Rd, Winchester, KY 40391

  Absolutely fabulous all brick home with incredible views, one owner, what makes this home special is the feeling of elegance, a total renovation offers the ultimate in living, spacious lower level provides full bath, family room, firepalce, walk out door to a large patio, first level dining room, great room with firepalce, showcase kitchen, living room, upstairs with large master suite, side

  Mila Ensor Ensor Real Estate, LLC

  1775 Irvine Rd, Winchester, KY 40391
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  /28

  $370,000 Sold Sep 03, 2025

  220 Spring Valley Dr, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 3,078 Sq Ft
  • Built 1975

  Last Sold Summary

  • 7% Below List Price
  • $120/SF
  • 3 Days On Market

  Current Estimated Value $415,347

  Last Listing Agent Tracey Goebel Tom Goebel & Company

  220 Spring Valley Dr, Winchester, KY 40391
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  /40

  Est $220,346 Not Listed For Sale

  26 Taylor Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 2,404 Sq Ft
  • Built 1945

  26 Taylor Ave, Winchester, KY 40391

  Last Sold Summary

  • 194% Above List Price
  • $31/SF
  • 130 Days On Market

  • Last Sold Price $75,000
  • Aug 29, 2023

  Last Listing Agent Bob Sophiea eXp Realty, LLC

Showing Results 641 - 680, Page 17 of 18