Winchester, KY Homes

• 

  

  

  /28

  $203,900

  Sold Dec 10, 2025

  25 Hiawatha Trail, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 925 Sq Ft
  • Built 1968

  Last Sold Summary

  • 3% Below List Price
  • $220/SF
  • 35 Days On Market

  Current Estimated Value $204,810

  Last Listing Agent Sarah Hess Keller Williams Commonwealth

  25 Hiawatha Trail, Winchester, KY 40391
• 

  

  

  /22

  Est $193,381

  Not Listed For Sale

  113 Buffalo Trace, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 960 Sq Ft
  • Built 1998

  113 Buffalo Trace, Winchester, KY 40391

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Elizabeth Herrington Bluegrass Sotheby's International Realty
• 

  

  

  /10

  $575,000

  $75K PRICE DROP

  • Land
  • 2.6 Acres
  • $221,154 per Acre

  529 Bullion Blvd Unit 3B, Winchester, KY 40391

  Ideally located along the heart of Bypass Road (ADT: 24,801) in Winchester, Kentucky between and surrounding Kroger and Walmart shopping centers. These lots are offered as 1+ acres and may be subdivided. Winchester, KY is the county seat of Clark County, KY and is part of the Lexington-Fayette KY Metropolitan Statistical Area, and is supported by such industries such as Amazon, Ale-8-One, and

  Greg Leveridge Block + Lot Homes

  529 Bullion Blvd Unit 3B, Winchester, KY 40391
• 

  

  

  /90

  $650,000

  Sold Jun 17, 2026

  142 Clubhouse Dr, Winchester, KY 40391

  • 6 Beds
  • 4 Baths
  • 4,351 Sq Ft
  • Built 2001

  Last Sold Summary

  • $149/SF
  • 10 Days On Market

  Current Estimated Value $642,627

  Last Listing Agent Timothy Saylor Threshold Real Estate Services

  142 Clubhouse Dr, Winchester, KY 40391
• 

  

  

  /47

  Est $641,064

  Not Listed For Sale

  1305 Irvine Rd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 3,020 Sq Ft
  • Built 1918

  1305 Irvine Rd, Winchester, KY 40391

  Last Sold Summary

  • 406 Days On Market

  Last Listing Agent Bonnie Mays United Real Estate Bluegrass
• 

  

  /11

  $50,000

  • Land
  • 17,859 Sq Ft
  • $121,951 per Acre

  308 Duclair Dr, Winchester, KY 40391

  Tucked away on a quiet cul-de-sac in Mallard Place, this .41-acre lot is ready for your vision. Imagine your dream home in a neighborhood known for its charm and convenience. Bring your house plans—your future starts here!

  Joseph Miller Keller Williams Legacy Group

  308 Duclair Dr, Winchester, KY 40391
• 

  

  /57

  $350,000

  Sold May 20, 2026

  220 Hibiscus Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,640 Sq Ft
  • Built 2001

  Last Sold Summary

  • $213/SF
  • 4 Days On Market

  Current Estimated Value $346,038

  Last Listing Agent Timothy Saylor Threshold Real Estate Services

  220 Hibiscus Ln, Winchester, KY 40391
• 

  

  /99

  Est $273,233

  Not Listed For Sale

  514 E Broadway St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,394 Sq Ft
  • Built 1960

  514 E Broadway St, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Josh Wood Freedom Realty & Property Management
• 

  

  /22

  $665,000

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,643 Sq Ft

  414 Alexis Way, Winchester, KY 40391

  Introducing the Alexis, a stunning all-brick ranch home with incredible curb appeal and a charming front porch. This thoughtfully designed 3-bedroom, 2.5-bath home features a desirable split-bedroom layout, offering privacy and comfort. The spacious primary suite includes a luxurious ensuite with double vanities, a walk-in closet with direct access to the separate utility room for added

  Shane Underwood Keller Williams Commonwealth

  414 Alexis Way, Winchester, KY 40391
• 

  

  /41

  $300,300

  Sold Nov 07, 2025

  37 Lynnway Dr, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 3,220 Sq Ft
  • Built 1976

  Last Sold Summary

  • $93/SF
  • 58 Days On Market

  Current Estimated Value $331,506

  Last Listing Agent Donna Thwaites Thwaites Realtors LLC

  37 Lynnway Dr, Winchester, KY 40391
• 

  

  /30

  Est $187,152

  Not Listed For Sale

  1 Apache Trail, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,584 Sq Ft
  • Built 1969

  1 Apache Trail, Winchester, KY 40391

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Pete doCouto Plum Tree Realty
• 

  

  /9

  $785,000

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,476 Sq Ft

  425 Alexis Way, Winchester, KY 40391

  Introducing the Highland, an elegant all-brick ranch home offering 4 bedrooms and 2.5 full baths in a thoughtfully designed split-bedroom layout. The spacious primary suite is a true highlight, featuring a luxurious tile shower, separate soaking tub, double vanities, and a large walk-in closet. The open-concept kitchen flows seamlessly into the great room, creating the perfect space for

  Shane Underwood Keller Williams Commonwealth

  425 Alexis Way, Winchester, KY 40391
• 

  

  /41

  $247,000

  Sold Sep 19, 2025

  3588 Stamper Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,530 Sq Ft
  • Built 1987

  Last Sold Summary

  • 1% Below List Price
  • $161/SF
  • 4 Days On Market

  Current Estimated Value $251,494

  Last Listing Agent Zach Johnson The Brokerage

  3588 Stamper Dr, Winchester, KY 40391
• 

  

  /27

  Est $203,582

  Not Listed For Sale

  7 Pocahontas Trail, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,550 Sq Ft
  • Built 1969

  7 Pocahontas Trail, Winchester, KY 40391

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Mila Ensor Ensor Real Estate, LLC
• 

  

  /72

  $406,900

  New Construction

  • 3 - 6 Beds
  • 2.5 - 5.5 Baths
  • 2,570 Sq Ft

  Jackie Plan at Boone's Crossing, Winchester, KY 40391

  Unleash your creativity with the Jackie floor plan, a flexible and thoughtfully designed new construction home that empowers you to shape your ideal living space. Built by one of the most trusted home builders in Central Kentucky, the Jackie is a standout choice for buyers searching for new construction homes in Lexington KY and surrounding communities who want space, versatility, and modern

  James Monroe Homes Builder

  2070 Boonesboro Rd Unit 39824254, Winchester, KY 40391
• 

  

  /20

  $205,000

  Sold Aug 19, 2025

  202 Custer Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,113 Sq Ft
  • Built 1999

  Last Sold Summary

  • 8% Above List Price
  • $184/SF
  • 2 Days On Market

  Current Estimated Value $197,740

  Last Listing Agent Brittany Beer eXp Realty, LLC

  202 Custer Ct, Winchester, KY 40391
• 

  

  /57

  Est $197,642

  Not Listed For Sale

  17 Hiawatha Trail, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,000 Sq Ft
  • Built 1968

  17 Hiawatha Trail, Winchester, KY 40391

  Last Sold Summary

  • 32 Days On Market

  Last Listing Agent Josh Wood Freedom Realty & Property Management
• 

  

  /36

  $539,500

  $10K PRICE DROP

  • 4 Beds
  • 5 Baths
  • 4,173 Sq Ft

  600 Boone Ave, Winchester, KY 40391

  Step into the timeless elegance of this stunning Southern antebellum-style home, where classic charm meets modern luxury. Boasting four spacious bedrooms and five beautifully appointed bathrooms, this grand residence offers an unparalleled level of sophistication and comfort. A breathtaking foyer and entryway welcome you with a sweeping staircase, and exquisite architectural details, setting the

  Holly Goeing The Agency

  600 Boone Ave, Winchester, KY 40391
• 

  

  /15

  $176,000

  Sold Oct 17, 2025

  7575 Irvine Rd, Winchester, KY 40391

  Last Sold Summary

  • 6% Below List Price
  • 2 Days On Market

  Current Estimated Value $188,054

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  7575 Irvine Rd, Winchester, KY 40391
• 

  

  /15

  Est $199,034

  Not Listed For Sale

  13 Hiawatha Trail, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,006 Sq Ft
  • Built 1968

  13 Hiawatha Trail, Winchester, KY 40391

  Last Sold Summary

  • 50 Days On Market

  Last Listing Agent Patrick Arvin Keller Williams Commonwealth
• 

  

  /38

  $355,000

  $25K PRICE DROP

  • 1 Bed
  • 2 Baths
  • 2,179 Sq Ft

  3359 Trapp-Goffs Corner Rd, Winchester, KY 40391

  Home listed as one bedroom while unofficially has 3 but 2 of them are interior rooms without windows. ( Owners Now Offering to pay up to $5,000 in closing cost and pre-paids on behalf of buyers). Tired of the honking horns , congested traffic, sirens of town living and dreaming of country living, your own slice of paradise? Maybe raising your own garden , owning chickens , goats, horses ,

  Wayne Elkins RE/MAX Creative Realty

  3359 Trapp-Goffs Corner Rd, Winchester, KY 40391
• 

  

  /27

  $355,000

  Sold Jul 06, 2026

  17 W Lexington Ave, Winchester, KY 40391

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

  Last Sold Summary

  • 9% Below List Price
  • $89/SF
  • 25 Days On Market

  Current Estimated Value $382,102

  Last Listing Agent Libby VanMeter Marshall Lane Real Estate - Lexington

  17 W Lexington Ave, Winchester, KY 40391
• 

  

  /29

  Est $226,777

  Not Listed For Sale

  46 Hiawatha Trail, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Built 1970

  46 Hiawatha Trail, Winchester, KY 40391

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Christina Baker United Real Estate Louisville
• 

  

  /27

  $380,000

  • 3 Beds
  • 2 Baths
  • 2,358 Sq Ft

  125 Amiens Blvd, Winchester, KY 40391

  Welcome to 125 Amiens Boulevard, where quality craftsmanship, thoughtful design, and everyday comfort come together in one exceptional home. Built by respected local builder Marcus Moore, this beautifully maintained all-brick ranch has been lovingly cared for and is truly move-in ready. From the moment you arrive, you'll appreciate the inviting curb appeal, spacious floor plan, and attention to

  Christina Hall ERA Select Real Estate

  125 Amiens Blvd, Winchester, KY 40391
• 

  

  /21

  $240,000

  Sold Jun 09, 2026

  720 Estes Dr, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,494 Sq Ft
  • Built 1970

  Last Sold Summary

  • 2% Below List Price
  • $161/SF
  • 28 Days On Market

  Current Estimated Value $243,267

  Last Listing Agent Jonathan Wood HomeLand Real Estate Inc - Mt Sterling

  720 Estes Dr, Winchester, KY 40391
• 

  

  /24

  Est $265,569

  Not Listed For Sale

  108 Dixon Way, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,377 Sq Ft
  • Built 2006

  108 Dixon Way, Winchester, KY 40391

  Last Sold Summary

  • 124 Days On Market

  Last Listing Agent Angie Conley Dixon Dixon Properties
• 

  

  /19

  $125,000

  $10K PRICE DROP Pending

  • Land
  • 4.01 Acres
  • $31,172 per Acre

  1940 Athens Boonesboro Rd, Winchester, KY 40391

  Escape to tranquility with this beautiful 4-acre lot in Clark County, offering the perfect setting to build your dream home. Tucked away on a quiet road, this property is surrounded by expansive farmland, ensuring ultimate privacy and peaceful living. A serene pond adds to the charm, providing a perfect spot to relax and enjoy the natural beauty of the land. This lot sits directly across from the

  Laura Sizemore Kentucky Land and Home

  1940 Athens Boonesboro Rd, Winchester, KY 40391
• 

  

  /10

  $325,000

  Sold Aug 29, 2025

  210 Cabin Creek Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,584 Sq Ft
  • Built 1999

  Last Sold Summary

  • $205/SF

  Current Estimated Value $342,449

  Last Listing Agent Janine Shackelford LPT Realty

  210 Cabin Creek Rd, Winchester, KY 40391
• 

  

  /19

  Est $216,500

  Not Listed For Sale

  170 Center Dr, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,517 Sq Ft
  • Built 1961

  170 Center Dr, Winchester, KY 40391

  Last Sold Summary

  • 52 Days On Market

  Last Listing Agent Larry Moore CENTURY 21 Simpson & Associates
• 

  

  /4

  $137,500

  • Land
  • 3.94 Acres
  • $34,898 per Acre

  150 Spencer Ln, Winchester, KY 40391

  Build your dream home in the stunning ESKIPPAKITHIKI OVERLOOKS! Looking for your next investment? This 3.940 acre parcel offers unlimited potential-whether you dream of building or simply holding land as it grows in value. Offering unparalleled views of a serene, natural setting. Perfect for a private retreat or family estate, this property invites you to design your ideal lifestyle surrounded by

  Kathryn Cheuvront Coldwell Banker McMahan

  150 Spencer Ln, Winchester, KY 40391
• 

  

  /36

  $261,000

  Sold Feb 04, 2026

  433 Wellington Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,234 Sq Ft
  • Built 2010

  Last Sold Summary

  • 2% Below List Price
  • $212/SF
  • 60 Days On Market

  Current Estimated Value $262,444

  Last Listing Agent Nick Ratliff Realty Team - Nicholas Ratliff Real Broker, LLC - Lexington

  433 Wellington Way, Winchester, KY 40391
• 

  

  /48

  Est $225,865

  Not Listed For Sale

  217 Locust Grove Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,055 Sq Ft
  • Built 1955

  217 Locust Grove Rd, Winchester, KY 40391

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Robin Murray The Agency
• 

  

  /24

  $199,900

  • 3 Beds
  • 2 Baths
  • 915 Sq Ft

  225 Buffalo Trace, Winchester, KY 40391

  This move in ready ranch home offering 3 bedrooms and 2 full bathrooms is ready for a new owner. This home is in an income restricted community, 80% of LIHTC for Clark County. Property offers brand new cabinets, countertops, appliances, flooring, fresh painting and more. Contact listing agent to receive the income limits for buyers to qualify to purchase property. Set up your showing today!

  Tyler I Back The Brokerage

  225 Buffalo Trace, Winchester, KY 40391
• 

  

  /65

  $275,000

  Sold Aug 15, 2025

  151 Hilltop Dr, Winchester, KY 40391

  • 4 Beds
  • 1.5 Baths
  • 1,873 Sq Ft
  • Built 1960

  Last Sold Summary

  • 1% Below List Price
  • $147/SF
  • 130 Days On Market

  Current Estimated Value $278,703

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  151 Hilltop Dr, Winchester, KY 40391
• 

  

  /58

  Est $200,668

  Not Listed For Sale

  219 Locust Grove Rd, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,191 Sq Ft
  • Built 1955

  219 Locust Grove Rd, Winchester, KY 40391

  Last Sold Summary

  • 27 Days On Market

  Last Listing Agent Josh Wood Freedom Realty & Property Management
• 

  

  /84

  $1,500,000

  • 4 Beds
  • 3 Baths
  • 7,172 Sq Ft

  351 Benton Rd, Winchester, KY 40391

  Welcome to a truly one-of-a-kind Kentucky estate where luxury, craftsmanship, and country living come together on 27 breathtaking acres in Clark County—just 10 minutes from the interstate for an easy commute while still enjoying complete privacy. Built with exceptional quality and thoughtfully designed by its original owner, this custom home offers over 7,000 square feet of living space with 4

  Darienne Hensley Keller Williams Legacy Group

  351 Benton Rd, Winchester, KY 40391
• 

  

  /63

  $445,000

  Sold May 22, 2026

  1911 Trapp-Goffs Corner Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,288 Sq Ft
  • Built 2000

  Last Sold Summary

  • 3% Below List Price
  • $345/SF
  • 51 Days On Market

  Last Listing Agent Cheri Shaffer Lifstyl Real Estate

  1911 Trapp-Goffs Corner Rd, Winchester, KY 40391
• 

  

  /29

  Est $201,382

  Not Listed For Sale

  505 Bob o Link Dr, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,228 Sq Ft
  • Built 1960

  505 Bob o Link Dr, Winchester, KY 40391

  Last Sold Summary

  • 22 Days On Market

  Last Listing Agent Kathryn Cheuvront Coldwell Banker McMahan
• 

  

  /18

  $365,000

  $4K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,990 Sq Ft

  11 Stoney Brook Dr Unit 1, Winchester, KY 40391

  This three bedroom home has been updated, new painting interior and exterior, new flooring, new light fixtures, new bath vanities, new granite in kitchen plus much more. Owner/Broker

  Garry Milton Milton and Associates Real Estate

  11 Stoney Brook Dr Unit 1, Winchester, KY 40391
• 

  /2

  $610,000

  Sold Aug 29, 2025

  4560 Pine Ridge Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,848 Sq Ft
  • Built 1905

  Last Sold Summary

  • $330/SF
  • 1 Day On Market

  Current Estimated Value $602,378

  Last Listing Agent Natalie Avant Berkshire Hathaway HomeServices Foster Realtors

  4560 Pine Ridge Rd, Winchester, KY 40391

Showing Results 241 - 280, Page 7 of 18