Winchester, KY Homes

/19
$499,000
- Land
- 36.94 Acres
- $13,508 per Acre
1455B Ky-89 Lot Unit Wp001, Winchester, KY 40391

Don't miss this rare chance to own 36.45 premium acres on the outskirts of Winchesteran unbeatable blend of open farmland, development potential, and a truly top-tier location. Just minutes from I-64 and a quick drive to Lexington, this tract offers the convenience buyers want with the space and freedom they rarely find. The gorgeous rolling fields make this property ideal for farming, hay

Greg Meade Whitetail Properties Real Estate

1455B Ky-89 Lot Unit Wp001, Winchester, KY 40391
/33
$332,000 Sold Oct 14, 2025

1831 Kiddville Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,756 Sq Ft
- Built 1963
Last Sold Summary
- 5% Below List Price
- $189/SF
- 82 Days On Market
Current Estimated Value $329,089

Last Listing Agent Joshua Davis The Agency

1831 Kiddville Rd, Winchester, KY 40391

/17
Est $477,667 Not Listed For Sale

1026 Crowe Ridge Rd, Winchester, KY 40391
- 1 Bath
- Built 1945
1026 Crowe Ridge Rd, Winchester, KY 40391

Last Sold Summary
- 10% Above List Price
- $407/SF
- 56 Days On Market
- Last Sold Price $435,000
- Jan 09, 2025
Last Listing Agent Sophia Herald Herald Real Estate

/62
$435,000 Pending
- 3 Beds
- 3.5 Baths
- 3,633 Sq Ft
2 Stoney Brook Dr, Winchester, KY 40391

Welcome to this spacious brick ranch with a finished walkout basement, perfectly positioned on a corner lot in the desirable Stoney Brook neighborhood. Sitting on nearly half an acre, this home brings the space and flexibility buyers are looking for with multiple living areas including a family room, living room, and formal dining room. The main level offers a primary en suite, an additional full

Kelli Hunt Berkshire Hathaway HomeServices Foster Realtors

2 Stoney Brook Dr, Winchester, KY 40391
/25
$223,000 Sold Nov 04, 2025

204 Crawford Ct, Winchester, KY 40391
- 4 Beds
- 2 Baths
- 1,636 Sq Ft
- Built 1960
Last Sold Summary
- 3% Below List Price
- $136/SF
- 1 Day On Market
Current Estimated Value $227,436

Last Listing Agent Tisha Monte Bluegrass Properties Group

204 Crawford Ct, Winchester, KY 40391

/26
Est $348,322 Not Listed For Sale

11705 Irvine Rd, Winchester, KY 40391
- 3 Beds
- 1.5 Baths
- 2,668 Sq Ft
- Built 1988
11705 Irvine Rd, Winchester, KY 40391

Last Sold Summary
- 58% Above List Price
- $82/SF
- 81 Days On Market
- Last Sold Price $220,000
- Jan 09, 2024
Last Listing Agent Matthew J. Reffett Re/Max Legacy Group - Paintsville

/57
$499,900
- 4 Beds
- 3 Baths
- 5,646 Sq Ft
16 Manor Dr, Winchester, KY 40391

One Time Homeowner! Beautiful fieldstone ranch on full finished basement. 4 Bedrooms, 3 full bathrooms. This home has a very large great room, perfect for entertaining! Home has a new roof and siding as of 2024, new windows as of 2025. Home has tons of storage and tons of character. Come see this wonderful house and make it your forever home!

Zella Rosenthal Tom Goebel & Company

16 Manor Dr, Winchester, KY 40391
/29
$227,500 Sold Sep 11, 2025

301 Cabin Creek Heights, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,220 Sq Ft
- Built 1970
Last Sold Summary
- 1% Above List Price
- $186/SF
- 0 Days On Market
Current Estimated Value $226,786

Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

301 Cabin Creek Heights, Winchester, KY 40391

/33
Est $222,789 Not Listed For Sale

510 Wills Rupard Rd, Winchester, KY 40391
- 2 Beds
- 1 Bath
- 1,592 Sq Ft
- Built 1990
510 Wills Rupard Rd, Winchester, KY 40391

Last Sold Summary
- 23% Above List Price
- $114/SF
- 2 Days On Market
- Last Sold Price $181,000
- May 25, 2023
Last Listing Agent Joe Marcum CENTURY 21 Advantage Realty

/29
$289,000 Pending
- 5 Beds
- 2 Baths
- 1,838 Sq Ft
426 E Broadway St, Winchester, KY 40391

Welcome home to this beautifully reimagined property in Winchester! Originally built in 1945, this 1.5-story home has been completely transformed from the ground up, offering the perfect blend of classic charm and modern peace of mind. With approximately 1,838 square feet, this home has been fully gutted to the studs and thoughtfully rebuilt—featuring all-new electrical, plumbing, HVAC system,

Alyssa M Boley Coldwell Banker McMahan

426 E Broadway St, Winchester, KY 40391
/2
$125,000 Sold May 23, 2025

265 Duclair Dr, Winchester, KY 40391
- Land
- 1.01 Acres
- $123,762 per Acre
Last Sold Summary
- 0 Days On Market
Last Listing Agent John Wilson Bluegrass Properties Group

265 Duclair Dr, Winchester, KY 40391

/33
Est $277,056 Not Listed For Sale

7344 Ironworks Rd, Winchester, KY 40391
- 2 Beds
- 1 Bath
- 1,400 Sq Ft
- Built 1925
7344 Ironworks Rd, Winchester, KY 40391

Last Sold Summary
- 27% Above List Price
- $156/SF
- 2 Days On Market
- Last Sold Price $219,000
- Mar 07, 2024
Last Listing Agent Jason Rainey Executive Real Estate, LLC

/56
$325,000 Pending
- 3 Beds
- 2 Baths
- 1,450 Sq Ft
215 Old Log Lick Rd, Winchester, KY 40391

Price drop plus Seller will credit Buyer $1,000 for carpet repair/replacement. Enjoy where you live! Zen like grounds will bring inner peace in this 1,450 sq foot home on over 3 private acres. Covered front and back porches span the width of the house. Get off the grid with the solar panels on the roof (25 yr warranty), six raised garden beds, and fenced chicken coop! Average utility bill $50 in

Kerry Ball Local First Realty, LLC

215 Old Log Lick Rd, Winchester, KY 40391
/41
$279,900 Sold Aug 12, 2025

225 Prescott Ln, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,808 Sq Ft
- Built 2006
Last Sold Summary
- $155/SF
- 8 Days On Market
Current Estimated Value $285,664

Last Listing Agent Teresa Richmond Freedom Realty & Property Management

225 Prescott Ln, Winchester, KY 40391

/82
Est $391,136 Not Listed For Sale

380 L E Junction Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 3,173 Sq Ft
- Built 1976
380 L E Junction Rd, Winchester, KY 40391

Last Sold Summary
- 21% Above List Price
- $102/SF
- 13 Days On Market
- Last Sold Price $324,000
- Jul 14, 2023
Last Listing Agent Davin Smith Caswell Prewitt Realty, Inc

/57
$350,000
- 4 Beds
- 2 Baths
- 3,261 Sq Ft
443 S Maple St, Winchester, KY 40391

Full of history and charm, this 1905 home sits on one of Winchester's most beloved and cherished streets, a place where homes like this are held onto for generations. It offers a rare opportunity to own a piece of the past while creating something truly your own. The inviting, oversized front porch sets the tone, perfect for quiet mornings, evening conversations, and the simple moments that make

Terra Long Keller Williams Commonwealth

443 S Maple St, Winchester, KY 40391
/24
$185,000 Sold Jun 23, 2025

605 Dixiana Dr, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,044 Sq Ft
- Built 1990
Last Sold Summary
- 3% Below List Price
- $177/SF
- 23 Days On Market
Current Estimated Value $191,968

Last Listing Agent Dale Hatton Dream Maker Realty, LLC

605 Dixiana Dr, Winchester, KY 40391

/51
Est $461,945 Not Listed For Sale

5600 Ecton Rd, Winchester, KY 40391
- 3 Beds
- 3 Baths
- 2,841 Sq Ft
- Built 1992
5600 Ecton Rd, Winchester, KY 40391

Last Sold Summary
- $162/SF
- 62 Days On Market
- Last Sold Price $460,000
- Dec 29, 2023
Last Listing Agent Kymberly McCreary Keller Williams Commonwealth

/38
$329,900
- 4 Beds
- 1 Bath
- 2,327 Sq Ft
162 French Ave, Winchester, KY 40391

Could 162 French Ave., Winchester, KY 40391 be your new address? This stunning, updated Craftsman home feels like it was pulled straight from the pages of Southern Living Magazine, blending modern updates with timeless character and charm. Recent improvements including new windows, doors, wiring, and fresh landscaping enhance the home while preserving its original appeal. This move-in ready

Jonathan Wood HomeLand Real Estate Inc - Mt Sterling

162 French Ave, Winchester, KY 40391
/39
$340,000 Sold Oct 10, 2025

219 Hampton Ave, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 2,929 Sq Ft
- Built 1972
Last Sold Summary
- 7% Below List Price
- $116/SF
- 48 Days On Market
Current Estimated Value $344,663

Last Listing Agent Jo Gawthrop Keller Williams Bluegrass Realty

219 Hampton Ave, Winchester, KY 40391

/38
Est $373,764 Not Listed For Sale

3070 Goshen Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 2,866 Sq Ft
- Built 1998
3070 Goshen Rd, Winchester, KY 40391

Last Sold Summary
- 2% Above List Price
- $128/SF
- 2 Days On Market
- Last Sold Price $367,000
- Apr 22, 2024
Last Listing Agent Kevin Bradley Keller Williams Legacy Group

/24
$369,900 New Construction
- 3 Beds
- 2 Baths
- 1,635 Sq Ft
206 Jett Dr, Winchester, KY 40391

New Construction, come view, great house plan, ranch on a crawl space, 3 bedrooms, 2 bath, you will love this inviting neighborhood, plan shown on line could vary, this is a spec home, all the colors have been decided, fixtures, flooring, brick, siding, cabinets, countertops have been ordered, restrictions apply, no HOA, buyer to verify sq ft of home and lot. This home is close to I-64, I-75,

Mila Ensor Ensor Real Estate, LLC

206 Jett Dr, Winchester, KY 40391
/58
$850,000 Sold Jun 27, 2025

2158 Venable Rd, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 2,980 Sq Ft
- Built 1988
Last Sold Summary
- $285/SF
- 1 Day On Market
Current Estimated Value $851,707

Last Listing Agent Emily Miller Bluegrass Sotheby's International Realty

2158 Venable Rd, Winchester, KY 40391

/88
Est $635,668 Not Listed For Sale

865 Sugar Ridge Rd, Winchester, KY 40391
- 3 Beds
- 3 Baths
- 2,146 Sq Ft
- Built 1997
865 Sugar Ridge Rd, Winchester, KY 40391

Last Sold Summary
- 14% Below List Price
- $345/SF
- 88 Days On Market
- Last Sold Price $740,000
- Apr 25, 2025
Last Listing Agent Alysia Niva Century 21 Advantage Realty - Georgetown

/10
$550,000 New Construction
- 3 Beds
- 2.5 Baths
- 2,200 Sq Ft
107 Bella Shae Way, Winchester, KY 40391

Welcome Home to the Winchester Floor Plan by CP Builders. This elegant ranch home features all-brick construction, a welcoming front porch, and a two-car garage. Step inside and be greeted by soaring 9-foot ceilings and a spacious open floor plan. The split bedroom design offers privacy and comfort, with a luxurious primary suite boasting an ensuite bathroom and a walk-in closet. Enjoy easy

Shane Underwood Keller Williams Commonwealth

107 Bella Shae Way, Winchester, KY 40391
/28
$89,900 Pending
- 3 Beds
- 2 Baths
32 Hays St, Winchester, KY 40391

Investor special! This property has been fully gutted and is ready for your vision. Major groundwork has already begun, including new PEX plumbing lines installed for water service, updated framing, and electrical improvements underway. Designed to accommodate a 3-bedroom, 2-bath layout, this property offers a true blank slate for investors, flippers, or contractors looking to customize finishes

Christa Joynt Keller Williams Commonwealth

32 Hays St, Winchester, KY 40391

/76
Est $794,322 Not Listed For Sale

775 Sugar Ridge Rd, Winchester, KY 40391
- 4 Beds
- 3 Baths
- 2,860 Sq Ft
- Built 1996
775 Sugar Ridge Rd, Winchester, KY 40391

Last Sold Summary
- 15% Above List Price
- $241/SF
- 2 Days On Market
- Last Sold Price $690,000
- Feb 24, 2025
Last Listing Agent Cassie Foley CENTURY 21 Advantage Realty

/3
$380,000 Pending
- 3 Beds
- 2 Baths
- 1,677 Sq Ft
270 Evergreen Dr, Winchester, KY 40391

Welcome to The Run for the Roses - a thoughtfully designed proposed construction home located in the desirable Locust Hill Acres community. This charming home offers an open concept floor plan perfect for modern living, featuring 3 spacious bedrooms and 2 full bathrooms on unfinished walkout basement.The large primary suite is a true retreat, complete with a generously sized walk-in closet

Rex Hall United Real Estate Bluegrass

270 Evergreen Dr, Winchester, KY 40391
/69
$282,500 Sold Sep 30, 2025

227 Cross Brook Ln, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,508 Sq Ft
- Built 2001
Last Sold Summary
- 1% Below List Price
- $187/SF
- 9 Days On Market
Current Estimated Value $280,903

Last Listing Agent Josh Wood Freedom Realty & Property Management

227 Cross Brook Ln, Winchester, KY 40391

/32
Est $305,463 Not Listed For Sale

810 Howard Creek Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,260 Sq Ft
- Built 2001
810 Howard Creek Rd, Winchester, KY 40391

Last Sold Summary
- 15% Above List Price
- $210/SF
- 17 Days On Market
- Last Sold Price $264,900
- Jun 09, 2023
Last Listing Agent Serena Cassidy Coldwell Banker McMahan

/29
$344,900
- 3 Beds
- 2 Baths
- 1,858 Sq Ft
23 Windridge Dr, Winchester, KY 40391

Welcome home!!! This beautifully updated all-brick ranch that perfectly blends charm and modern upgrades in a well established, desirable neighborhood is sure to please. Step inside to a bright open-concept living space featuring luxury vinyl flooring, a stunning wood-burning fireplace, and exposed wood ceiling beams that create a warm, inviting atmosphere in the spacious family room. The

Holly Goeing The Agency

23 Windridge Dr, Winchester, KY 40391
/75
$289,900 Sold Aug 11, 2025

126 Ashley Dr, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,429 Sq Ft
- Built 1992
Last Sold Summary
- $203/SF
- 0 Days On Market
Current Estimated Value $288,570

Last Listing Agent Jennifer Guyton White Realty, LLC

126 Ashley Dr, Winchester, KY 40391

/53
Est $291,334 Not Listed For Sale

1489 White Conkwright Rd, Winchester, KY 40391
- 3 Beds
- 1.5 Baths
- 1,126 Sq Ft
- Built 1995
1489 White Conkwright Rd, Winchester, KY 40391

Last Sold Summary
- 6% Above List Price
- $244/SF
- 45 Days On Market
- Last Sold Price $275,000
- Mar 11, 2024
Last Listing Agent Sabina Chambers Semonin Realty

/57
$350,000 Pending
- 3 Beds
- 2 Baths
- 1,640 Sq Ft
220 Hibiscus Ln, Winchester, KY 40391

Welcome home to this immaculate gem nestled in the charming Hibiscus Terrace Subdivision! This beautifully maintained three-bedroom, two-bathroom home offers 1,640 square feet of thoughtfully designed living space that blends comfort with everyday functionality. Inside, discover a warm, inviting interior where fresh carpet installed in 2022 greets you with plush softness throughout. The

Timothy Saylor Threshold Real Estate Services

220 Hibiscus Ln, Winchester, KY 40391
/58
$345,000 Sold Nov 14, 2025

205 Chardonnay Ct, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 2,179 Sq Ft
- Built 1991
Last Sold Summary
- 8% Below List Price
- $158/SF
- 59 Days On Market
Current Estimated Value $357,768

Last Listing Agent Janna Chalfant Smith United Real Estate Bluegrass

205 Chardonnay Ct, Winchester, KY 40391

/23
Est $305,385 Not Listed For Sale

440 White Conkwright Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,624 Sq Ft
- Built 2004
440 White Conkwright Rd, Winchester, KY 40391

Last Sold Summary
- 25% Above List Price
- $151/SF
- 3 Days On Market
- Last Sold Price $245,000
- Jun 21, 2023
Last Listing Agent Louis Baldwin Threshold Real Estate Services

/31
$299,900 Pending
- 4 Beds
- 2 Baths
- 1,840 Sq Ft
306 Trapp-Goffs Corner Rd, Winchester, KY 40391

Beautiful Four Bedroom 2 Bathroom Ranch Home On A Finished Basement With Over 2 Acres!! Bring Your Family, Toys, Animals And Enjoy Country Living Close To Mountain Parkway And Close To Two Country Restaurants! Sellers Have Finished Basement To Add An Additional Bedroom, Bathroom And Lots Of Storage!! And Dont Miss The Large Deck With a View!

Patrick Arvin Keller Williams Commonwealth

306 Trapp-Goffs Corner Rd, Winchester, KY 40391
/27
$210,000 Sold Sep 04, 2025

305 Geronimo Ct, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,150 Sq Ft
- Built 1999
Last Sold Summary
- 5% Below List Price
- $183/SF
- 1 Day On Market
Current Estimated Value $216,633

Last Listing Agent Aaron Kendall Lifstyl Real Estate

305 Geronimo Ct, Winchester, KY 40391

/78
Est $525,547 Not Listed For Sale

7625 Irvine Rd, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 2,689 Sq Ft
- Built 2006
7625 Irvine Rd, Winchester, KY 40391

Last Sold Summary
- 8% Below List Price
- $212/SF
- 42 Days On Market
- Last Sold Price $570,000
- Aug 14, 2023
Last Listing Agent Elizabeth Torchia Caswell Prewitt Realty, Inc

/15
$294,900
- 4 Beds
- 2.5 Baths
- 1,693 Sq Ft
327 Newcastle Ln, Winchester, KY 40391

Seller is offering $2000 total towards buyers concession (can be used for downpayment, prepaids and closing cost)!! Welcome home to this cozy cute FOUR bedroom house with 2 full bath/ 1 half bath! Rare to find- Primary bedroom and full bath on first floor. Large living area with plenty of sunlight through insulated windows and skylights. This open floorpan also showcases a nice open staircase

Huong Dunn Bluegrass Property Exchange

327 Newcastle Ln, Winchester, KY 40391

Showing Results 81 - 120, Page 3 of 18

Kentucky Clark County Winchester

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