Winchester, KY Homes

/49
Est $321,143 Not Listed For Sale
- 5 Beds
- 2.5 Baths
- 2,333 Sq Ft
373 Old Ironworks Rd, Winchester, KY 40391

373 Old Ironworks Rd, Winchester, KY 40391

/36
$262,500 Pending
- 3 Beds
- 2 Baths
- 1,234 Sq Ft
433 Wellington Way, Winchester, KY 40391

Completely renovated and move-in ready! This 3-bedroom, 2-bath home offers 1,234 sq. ft. of stylish living with beautiful hardwood floors, fresh finishes, and a bright open layout. The vaulted ceiling in the main living area adds space and light, while the updated kitchen features modern cabinetry and new appliances. Both bathrooms have been tastefully redone, and every detail reflects quality

Stephen Brashear Real Broker LLC

433 Wellington Way, Winchester, KY 40391
/47
$330,000 Sold Mar 31, 2025

150 Privacy Ln, Winchester, KY 40391
- 3 Beds
- 3 Baths
- 2,784 Sq Ft
- Built 1987
Last Sold Summary
- 6% Below List Price
- $119/SF
- 103 Days On Market
Current Estimated Value $347,015

Last Listing Agent Jason Joseph Keller Williams Commonwealth

150 Privacy Ln, Winchester, KY 40391

/45
Est $517,747 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,244 Sq Ft
1159 Cabin Creek Rd, Winchester, KY 40391

1159 Cabin Creek Rd, Winchester, KY 40391

/17
$439,000
- 4 Beds
- 2 Baths
- 1,950 Sq Ft
104 Colby Hills Dr, Winchester, KY 40391

(Reducted 50,000) for fast sell. Welcome to this beautiful ranch home, located in this desirable Colby Hill subdivision this house has been updated with new interior painting, new flooring, new kitchen cabinets, and tops, new bathrooms, large new lighting, 2 car garage, 2 fireplaces, living room, family room, dinning area, large new deck ,all this on a large corner lot. Owner/Broker

Garry Milton Milton and Associates Real Estate

104 Colby Hills Dr, Winchester, KY 40391
/73
$325,000 Sold Sep 23, 2025

407 Fairholme Way, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,805 Sq Ft
- Built 2021
Last Sold Summary
- 4% Below List Price
- $180/SF
- 123 Days On Market
Current Estimated Value $328,033

Last Listing Agent Josh Wood Freedom Realty & Property Management

407 Fairholme Way, Winchester, KY 40391

/15
Est $313,847 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,580 Sq Ft
158 Cabin Creek Heights, Winchester, KY 40391

158 Cabin Creek Heights, Winchester, KY 40391

/3
$380,000 New Construction
- 3 Beds
- 2 Baths
- 1,677 Sq Ft
230 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.The large primary suite is a true retreat, complete with a generously sized walk-in closet and a well-appointed ensuite

Rex Hall United Real Estate Bluegrass

230 Evergreen Dr, Winchester, KY 40391
/55
$785,000 Sold Feb 25, 2025

280 Penny Ln, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 2,885 Sq Ft
- Built 2014
Last Sold Summary
- 1% Below List Price
- $272/SF
- 13 Days On Market
Current Estimated Value $822,804

Last Listing Agent Nora Williams Keller Williams Commonwealth

280 Penny Ln, Winchester, KY 40391

/43
Est $501,232 Not Listed For Sale
- 4 Beds
- 2 Baths
- 2,060 Sq Ft
2100 Ecton Rd, Winchester, KY 40391

2100 Ecton Rd, Winchester, KY 40391

/22
$265,000
- 4 Beds
- 2 Baths
- 2,332 Sq Ft
35 Cherokee Ct, Winchester, KY 40391

Step into this 4-bedroom, 2 full bath split-foyer home, perfectly designed for comfortable everyday living. The upper level features three generously sized bedrooms, a full bath, a bright living room, kitchen, and dining area—ideal for gathering with family and friends. Just off the kitchen, enjoy easy access to the covered deck overlooking a spacious backyard. The lower level offers even more

Brenda Rue Keller Williams Bluegrass Realty

35 Cherokee Ct, Winchester, KY 40391
/40
$210,000 Sold Sep 11, 2025

635 Lisletown Ln, Winchester, KY 40391
- 2 Beds
- 2 Baths
- 1,628 Sq Ft
- Built 1981
Last Sold Summary
- 12% Below List Price
- $129/SF
- 31 Days On Market
Current Estimated Value $217,546

Last Listing Agent Robin Jones Keller Williams Legacy Group

635 Lisletown Ln, Winchester, KY 40391

/44
Est $512,629 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,070 Sq Ft
601 Wades Mill Rd, Winchester, KY 40391

601 Wades Mill Rd, Winchester, KY 40391

/29
$219,000
- 3 Beds
- 2 Baths
- 2,050 Sq Ft
52 Hillcrest Dr, Winchester, KY 40391

3-bedroom, 2-bath home located in Winchester featuring a full walk-out basement that adds flexibility and usable space. This property offers a great opportunity for buyers looking to update and customize to their vision. Solid layout with strong potential for added value through improvements. Ideal for investors or owner-occupants seeking a well-priced home with upside.

Karan Singh 85W Real Estate

52 Hillcrest Dr, Winchester, KY 40391
/43
$485,000 Sold Jun 23, 2025

430 Fairholme Way, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 2,414 Sq Ft
- Built 2017
Last Sold Summary
- 4% Below List Price
- $201/SF
- 55 Days On Market
Current Estimated Value $489,309

Last Listing Agent Robyn Bradley Woods Realty Group

430 Fairholme Way, Winchester, KY 40391

/127
Est $701,489 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,514 Sq Ft
1924 Wades Mill Rd, Winchester, KY 40391

1924 Wades Mill Rd, Winchester, KY 40391

/2
$110,000
- Land
- 0.32 Acre
- $343,750 per Acre
250 Duclair Dr, Winchester, KY 40391

Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

John Wilson Bluegrass Properties Group

250 Duclair Dr, Winchester, KY 40391
/24
$186,000 Sold May 14, 2025

205 Arbor Ct, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,188 Sq Ft
- Built 1994
Last Sold Summary
- 3% Above List Price
- $157/SF
- 77 Days On Market
Current Estimated Value $188,185

Last Listing Agent Kathryn Cheuvront Coldwell Banker McMahan

205 Arbor Ct, Winchester, KY 40391

/3
Est $347,095 Not Listed For Sale
- 3 Beds
- 1,260 Sq Ft
1591 Gay Evans Rd, Winchester, KY 40391

1591 Gay Evans Rd, Winchester, KY 40391

/21
$139,000
- 2 Beds
- 1 Bath
- 886 Sq Ft
9 Linden Ave, Winchester, KY 40391

Back on Market due to: Buyer's financing fell through. Very nice home with hardwood floors in main areas featuring 2 bedrooms, 1 bath, permanent stairs to attic that has windows and could possibly be 2 bedrooms or bonus room. Enjoy your coffee on the front porch in the mornings! The storage shed in the back yard conveys with property. Home being sold as-is, where-is, sale pending court approval,

Emily Hacker-Todd CENTURY 21 Advantage Realty

9 Linden Ave, Winchester, KY 40391
/30
$310,900 Sold Sep 12, 2025

115 Hampton Ave, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 3,042 Sq Ft
- Built 1960
Last Sold Summary
- 4% Below List Price
- $102/SF
- 2 Days On Market
Current Estimated Value $315,253

Last Listing Agent Lauren Ball Deborah Ball Realty

115 Hampton Ave, Winchester, KY 40391

/50
Est $676,287 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 3,200 Sq Ft
1909 Gay Evans Rd, Winchester, KY 40391

1909 Gay Evans Rd, Winchester, KY 40391

/2
$89,100 Pending
- Land
- 7.86 Acres
- $11,336 per Acre
13067 Irvine Rd, Winchester, KY 40391

Mendel Tipton Natural Bridge Realty

13067 Irvine Rd, Winchester, KY 40391
/82
$385,000 Sold Nov 07, 2025

1138 Lafayette Blvd, Winchester, KY 40391
- 3 Beds
- 3 Baths
- 2,300 Sq Ft
- Built 1995
Last Sold Summary
- 4% Above List Price
- $167/SF
- 1 Day On Market
Last Listing Agent Josh Wood Freedom Realty & Property Management

1138 Lafayette Blvd, Winchester, KY 40391

/96
Est $866,326 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 3,272 Sq Ft
1995 Gay Evans Rd, Winchester, KY 40391

1995 Gay Evans Rd, Winchester, KY 40391

/10
$591,650 Pending
- 3 Beds
- 2.5 Baths
- 2,200 Sq Ft
104 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

104 Bella Shae Way, Winchester, KY 40391
/17
$190,000 Sold Sep 10, 2025

114 Sunset Heights, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,059 Sq Ft
- Built 1960
Last Sold Summary
- 3% Below List Price
- $179/SF
- 50 Days On Market
Current Estimated Value $189,996

Last Listing Agent Susan Baldwin Threshold Real Estate Services

114 Sunset Heights, Winchester, KY 40391

/60
Est $164,767 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,492 Sq Ft
1333 Jackson Ferry Rd, Winchester, KY 40391

1333 Jackson Ferry Rd, Winchester, KY 40391

/2
$5,646,000 Pending
- 2 Beds
- 3 Baths
- 37,192 Sq Ft
175 Chatham Place, Winchester, KY 40391

36 Townhomes ,located behind Lowes,Winchester,Ky.Great rental property, owner will do some owner financing

Garry Milton Milton and Associates Real Estate

175 Chatham Place, Winchester, KY 40391
/48
$222,500 Sold Jul 28, 2025

217 Locust Grove Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 2,055 Sq Ft
- Built 1955
Last Sold Summary
- 1% Above List Price
- $108/SF
- 2 Days On Market
Current Estimated Value $223,776

Last Listing Agent Robin Murray The Agency

217 Locust Grove Rd, Winchester, KY 40391

/10
Est $1,102,758 Not Listed For Sale
- Studio
- 3,351 Sq Ft
4479 Muddy Creek Rd, Winchester, KY 40391

4479 Muddy Creek Rd, Winchester, KY 40391

/54
$312,000 Open Sun 2PM - 5PM
- 4 Beds
- 1.5 Baths
- 2,170 Sq Ft
214 S Burns Ave, Winchester, KY 40391

Own a beautifully maintained piece of Winchester, KY history on desirable South Burns Avenue. This charming home features an inviting wrap-around porch perfect for year-round enjoyment and outstanding curb appeal. Step into a warm and welcoming entryway where refinished hardwood floors flow throughout the main level. Original pocket doors open into the library, showcasing the home's timeless

Christa Joynt Keller Williams Commonwealth

214 S Burns Ave, Winchester, KY 40391
/34
$342,000 Sold Sep 16, 2025

3560 Wades Mill Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,305 Sq Ft
- Built 1950
Last Sold Summary
- 10% Below List Price
- $262/SF
- 37 Days On Market
Current Estimated Value $344,847

Last Listing Agent Sarah MacHarg Kentucky Land and Home

3560 Wades Mill Rd, Winchester, KY 40391

/91
Est $419,400 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,514 Sq Ft
2184 Cole Rd, Winchester, KY 40391

2184 Cole Rd, Winchester, KY 40391

/36
$379,000
- 3 Beds
- 2 Baths
- 2,000 Sq Ft
133 Shala-Mar Rue, Winchester, KY 40391

Welcome to your next home in one of Clark County's most desirable neighborhoods—Shala Mar Estates! This beautifully updated 3-bedroom, 2-bathroom home offers the perfect blend of comfort, space, and modern convenience. Step into the expansive primary bedroom, a true retreat, complete with a stunning ensuite bathroom featuring a brand-new soaking tub and a separate tiled shower. The additional

Nena Honaker Tom Goebel & Company

133 Shala-Mar Rue, Winchester, KY 40391
/32
$195,700 Sold Mar 10, 2025

162 French Ave, Winchester, KY 40391
- 4 Beds
- 1 Bath
- 2,327 Sq Ft
- Built 1920
Last Sold Summary
- 11% Below List Price
- $84/SF
- 15 Days On Market
Current Estimated Value $219,512

Last Listing Agent Dale Hatton Dream Maker Realty, LLC

162 French Ave, Winchester, KY 40391

/23
Est $272,480 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,487 Sq Ft
421 Jameson Way, Winchester, KY 40391

421 Jameson Way, Winchester, KY 40391

/38
$389,900
- 4 Beds
- 2 Baths
- 2,659 Sq Ft
6239 Old Boonesboro Rd, Winchester, KY 40391

Welcome Home to the beautiful country! If you've been looking for quiet, space, and a place that truly feels like home, this charming Cape Cod on nearly 2 acres in Clark County checks all the boxes. Tucked into a peaceful rural setting yet conveniently located near I-75, I-64 and the Winchester Bypass, this property offers the best of country living with easy access to town. With over 2,600

Kenya Woods United Real Estate Bluegrass

6239 Old Boonesboro Rd, Winchester, KY 40391
/5
$41,500 Sold Sep 15, 2025

434 Fairholme Way, Winchester, KY 40391
- Land
- 0.36 Acre
- $115,278 per Acre
Last Sold Summary
- 8% Below List Price
- 6 Days On Market
Current Estimated Value $53,685

Last Listing Agent Justin Lee JL Realty Group, LLC

434 Fairholme Way, Winchester, KY 40391

/54
Est $277,385 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,776 Sq Ft
427 Jameson Way, Winchester, KY 40391

427 Jameson Way, Winchester, KY 40391

Showing Results 161 - 200, Page 5 of 18

Kentucky Clark County Winchester

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