Clark County, KY Homes

/33
$285,000
- 3 Beds
- 2 Baths
- 1,790 Sq Ft
211 Lindsey Ct, Winchester, KY 40391

Nicely updated split-level home with a large, fenced backyard, located on a quiet cul-de-sac. This energy-efficient home boasts a brand-new HVAC system, a recently replaced roof, fresh paint and stylish new LVP flooring throughout the house. The large kitchen has updated countertops and cabinets, as well as brand-new stainless steel appliances with three-year warranties. Both bathrooms have been

Lesley Ward Biederman Real Estate

211 Lindsey Ct, Winchester, KY 40391
/2
$85,000 Sold Dec 12, 2025

1385 Sewell Shop Rd, Winchester, KY 40391
- Land
- 6.43 Acres
- $13,219 per Acre
Last Sold Summary
- 6% Below List Price
- 6 Days On Market
Last Listing Agent Zella Rosenthal Tom Goebel & Company

1385 Sewell Shop Rd, Winchester, KY 40391

/27
Est $187,873 Not Listed For Sale

37 Jackson St, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,400 Sq Ft
- Built 1940
37 Jackson St, Winchester, KY 40391

Last Sold Summary
- 16% Above List Price
- $116/SF
- 30 Days On Market
Last Sold Price $162,000

Last Listing Agent O. Debbie Pennington CENTURY 21 Advantage Realty

/18
$99,000
- 2 Beds
- 1 Bath
- 910 Sq Ft
114 Magnolia St, Winchester, KY 40391

Great opportunity for investors, flippers, or anyone looking for a project with tons of potential! This 2 bedroom, 1 bath home features a 2 year old roof, giving you a solid head start on future updates. With its convenient location and plenty of possibilities, this property is ready for someone to bring their vision! Selling as is. Cash or conventional financing only.

Michelle Blackburn RE/MAX Creative, Winchester

114 Magnolia St, Winchester, KY 40391
/53
$867,500 Sold Aug 01, 2025

511 Boone Ave, Winchester, KY 40391
- 4 Beds
- 4.5 Baths
- 4,698 Sq Ft
- Built 1885
Last Sold Summary
- 11% Below List Price
- $185/SF
- 318 Days On Market
Current Estimated Value $908,797

Last Listing Agent Greg Leveridge Block + Lot Real Estate

511 Boone Ave, Winchester, KY 40391

/43
Est $144,485 Not Listed For Sale

116 Park Ave, Winchester, KY 40391
- 1 Bed
- 1 Bath
- 1,576 Sq Ft
- Built 1940
116 Park Ave, Winchester, KY 40391

Last Sold Summary
- 33% Above List Price
- $69/SF
- 23 Days On Market
Last Sold Price $108,500

Last Listing Agent Christa Joynt Keller Williams Commonwealth

/9
$1,350,000
- Land
- 3.02 Acres
- $447,020 per Acre
155 April Way, 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,

Greg Leveridge Block + Lot Real Estate

155 April Way, Winchester, KY 40391
/36
$420,000 Sold Feb 25, 2026

134 Fontaine Blvd, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 2,747 Sq Ft
- Built 1994
Last Sold Summary
- 7% Below List Price
- $153/SF
- 126 Days On Market
Current Estimated Value $421,734

Last Listing Agent Craig Bridgewater Bridgewater Real Estate

134 Fontaine Blvd, Winchester, KY 40391

/19
Est $164,963 Not Listed For Sale

Unlisted Address
- 3 Beds
- 1 Bath
- 1,683 Sq Ft
- Built 2023
Unlisted Address

Last Sold Summary
- 41% Above List Price
- $70/SF
- 6 Days On Market
Last Sold Price $117,000

Last Listing Agent Darrell Lewis DIY Flat Fee.com

/2
$100,000
- Land
- 0.31 Acre
- $322,581 per Acre
215 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

215 Duclair Dr, Winchester, KY 40391
/41
$310,000 Sold Dec 29, 2025

1996 White Conkwright Rd, Winchester, KY 40391
- 2 Beds
- 1 Bath
- 1,055 Sq Ft
- Built 1966
Last Sold Summary
- 9% Below List Price
- $294/SF
- 45 Days On Market
Current Estimated Value $320,605

Last Listing Agent Lucy Martin Jenkins United Real Estate Bluegrass

1996 White Conkwright Rd, Winchester, KY 40391

/26
Est $250,442 Not Listed For Sale

20 Jackson St, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,650 Sq Ft
- Built 1940
20 Jackson St, Winchester, KY 40391

Last Sold Summary
- 4% Above List Price
- $146/SF
- 10 Days On Market
Last Sold Price $240,900

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

/65
$667,700 Pending
- 5 Beds
- 4.5 Baths
- 4,712 Sq Ft
20 Stoney Brook Dr, Winchester, KY 40391

Welcome to 20 Stoney Brook Drive. Step into luxury with this meticulously maintained executive home where no expense has been spared and every detail has been thoughtfully curated. Offering 5 bedrooms and 4.5 baths, a walk-out basement, this stunning residence features a grand two-story foyer that sets the tone for the elegance found throughout. Entering the home on the right, you will find a

Lucy Martin Jenkins United Real Estate Bluegrass

20 Stoney Brook Dr, Winchester, KY 40391
/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 $584,967

Last Listing Agent Shane Underwood Keller Williams Commonwealth

102 Bella Shae Way, Winchester, KY 40391

/25
Est $209,510 Not Listed For Sale

21 Vine St, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,080 Sq Ft
- Built 1960
21 Vine St, Winchester, KY 40391

Last Sold Summary
- 2% Above List Price
- $190/SF
- 0 Days On Market
Last Sold Price $204,900

Last Listing Agent Kymberly McCreary EXP Realty, LLC

/34
$275,700
- 3 Beds
- 2 Baths
- 1,682 Sq Ft
404 Wellington Way, Winchester, KY 40391

This house is located minutes from the Winchester Bypass and within walking distance of the new Clark County Pre-school. The house features 3 bedrooms and 2 full baths. The kitchen is supplied with all the appliances. And the house also has a washer and dryer. The large great room is perfect for watching the favorite sports teams and movies with family and friends. The sellers added fiber optics

Craig Bridgewater Bridgewater Real Estate

404 Wellington Way, Winchester, KY 40391
/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 $337,463

Last Listing Agent Melissa Brown Keller Williams Legacy Group

366 Hanover Dr, Winchester, KY 40391

/39
Est $260,173 Not Listed For Sale

217 E Washington St, Winchester, KY 40391
- 4 Beds
- 3 Baths
- 2,183 Sq Ft
- Built 1940
217 E Washington St, Winchester, KY 40391

Last Sold Summary
- 11% Above List Price
- $108/SF
- 21 Days On Market
Last Sold Price $235,000

Last Listing Agent Joshua Lynch The Brokerage

/2
$100,000
- Land
- 0.32 Acre
- $312,500 per Acre
155 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

155 Duclair Dr, Winchester, KY 40391
/10
$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 $144,535

Last Listing Agent Darrell Lewis DIYFlatFee.Com

17 Waveland Ave, Winchester, KY 40391

/29
Est $232,841 Not Listed For Sale

167 E Washington St, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,763 Sq Ft
- Built 1940
167 E Washington St, Winchester, KY 40391

Last Sold Summary
- 8% Above List Price
- $122/SF
- 5 Days On Market
Last Sold Price $215,000

Last Listing Agent Kymberly McCreary EXP Realty, LLC

/47
$499,000
- 5 Beds
- 3.5 Baths
- 3,823 Sq Ft
595 Earlymeade Dr, Winchester, KY 40391

Entertaining the idea of entertaining family and friends? Looking for space for living the good life in a fun house in a great neighborhood? Then look no further. This house is ready for you to make it your new home. Located in the desirable neighborhood of Earlymeade, this house is minutes from the Winchester Bypass, I- 64 corridor and the Hamburg area of Lexington. Along with 5 bedrooms and 3.5

Craig Bridgewater Bridgewater Real Estate

595 Earlymeade Dr, Winchester, KY 40391
/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 $218,554

Last Listing Agent Elizabeth Hodge Lifstyl Real Estate

213 Blair Ave, Winchester, KY 40391

/27
Est $157,422 Not Listed For Sale

47 Buckner St, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,632 Sq Ft
- Built 1930
47 Buckner St, Winchester, KY 40391

Last Sold Summary
- 57% Above List Price
- $61/SF
- 17 Days On Market
Last Sold Price $100,000

Last Listing Agent Keith Wilson Coldwell Banker McMahan

/15
$600,000
- 8 Beds
- 4 Baths
- 5,046 Sq Ft
101 S Burns Ave Unit 1,2,3,4, Winchester, KY 40391

Step into a rare investment opportunity in the heart of downtown Winchester! This beautifully renovated 4-plex offers charm, space, and convenience — all within a fully restored historic building. Each of the four spacious units boasts approximately 1,296 sq ft, blending timeless character with modern updates. The entire property has been thoughtfully renovated in 2021, including a brand-new

Priya Patel-Rossetti Big Blue Realty

101 S Burns Ave Unit 1,2,3,4, Winchester, KY 40391
/2
$110,000 Sold May 13, 2025

140 Duclair Dr, Winchester, KY 40391
- Land
- 0.42 Acre
- $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

/26
Est $186,730 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
- 29% Above List Price
- $85/SF
- 39 Days On Market
Last Sold Price $145,000

Last Listing Agent Michelle Blackburn RE/MAX

/4
$67,500
- Land
- 1.92 Acres
- $35,156 per Acre
12569 Ironworks Rd, Winchester, KY 40391

Build your dream home in the stunning ESKIPPAKITHIKI OVERLOOKS! Or hold as investment property and watch this land grow in value. This lot containing 1.919 acres, offer 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 the beauty and tranquility. Don't miss your opportunity to own

Kathryn Cheuvront Coldwell Banker McMahan

12569 Ironworks Rd, Winchester, KY 40391
/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 $545,180

Last Listing Agent Kelly Nisbet Coldwell Banker McMahan

31 Bonnie Brook Ln, Winchester, KY 40391

/11
Est $128,967 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

Last Listing Agent Michelle Newman Team Pannell Real Estate

/3
$825,000 New Construction
- 3 Beds
- 2.5 Baths
- 2,995 Sq Ft
111 Bella Shae Way, Winchester, KY 40391

Welcome Home to the Park Place Floor Plan by CP Builders. This elegant ranch home features all-brick construction and a thoughtfully designed split bedroom layout for maximum privacy. The open floor plan seamlessly connects the living, dining, and kitchen areas, creating a warm and inviting atmosphere. Thespacious kitchen is a chef's dream, boasting a large island, a convenient pantry, and a

Shane Underwood Keller Williams Commonwealth

111 Bella Shae Way, Winchester, KY 40391
/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

/25
Est $167,935 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
- 13% Above List Price
- $155/SF
- 1 Day On Market
Last Sold Price $149,000

Last Listing Agent Tyanne Whitworth RE/MAX

/68
$2,450,000
- 5 Beds
- 5 Baths
- 6,284 Sq Ft
5039 Combs Ferry Rd, Ford, KY 40391

This 5 Bedroom, 5 Bathroom home is quietly located in the highly desired Combs Ferry area of Clark County. Location is evident as you are approximately an 8-minute drive to Hamburg as well as 8-minute drive to downtown Winchester. This complete custom home was constructed in 2022. The 6284 sqft boasts custom features including built in appliances, in-ground oversized heated pool with outdoor

Michael Hilario The Agency

5039 Combs Ferry Rd, Ford, KY 40391
/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 $464,023

Last Listing Agent O Eve Stern Threshold Real Estate Services

497 Goose Creek Rd, Winchester, KY 40391

/20
Est $147,746 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

Last Listing Agent Whitney Ensor Ensor Real Estate, LLC

/4
$225,000
- Land
- 8.09 Acres
- $27,812 per Acre
2110 Athens Boonesboro Rd, Ford, KY 40391

Prime building lot - 8.092 acres ready for your new dream home! Come pick your dream lot and enjoy the great views of the countryside and farmland. Rural living with the convenience of being just 15-20 minutes away from Lexington, Winchester and the interstate (I-75). 2110 approved for its own entrance. Multiple lots to choose from ranging from 4-8 acres +/-. Call today to get the first choice on

Megan McCoy Keller Williams Legacy Group

2110 Athens Boonesboro Rd, Ford, KY 40391
/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 $298,976

Last Listing Agent Alyssa M Boley Coldwell Banker McMahan

220 Mcdowell Dr, Winchester, KY 40391

/16
Est $170,389 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
- 29% Above List Price
- $101/SF
- 0 Days On Market
Last Sold Price $131,723

Last Listing Agent Roscoe Riley Blu Horizon Real Estate

/62
$399,900 Pending
- 3 Beds
- 3 Baths
- 2,475 Sq Ft
601 Gilbert Ct, Winchester, KY 40391

Welcome to 601 Gilbert Court in Winchester, KY. Tucked away in a quiet cul de sac in a desirable neighborhood, this spacious 3 bedroom, 3 full bathroom home offers room to spread out with a large open concept living room and kitchen that is perfect for gathering, entertaining, or simply enjoying everyday life. The oversized living space flows effortlessly into the kitchen and dining area,

Brooke Otis Mullins RO&CO Real Estate

601 Gilbert Ct, Winchester, KY 40391

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Kentucky Clark County

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