Clark County, KY Homes

/57
Est $440,462

Not Listed For Sale

402 S Maple St, Winchester, KY 40391
- 4 Beds
- 2 Baths
- 3,864 Sq Ft
- Built 1896
402 S Maple St, Winchester, KY 40391

Last Sold Summary
- 24 Days On Market
Last Listing Agent Kristy Hall The Agency

/52
$785,000

Pending
- 4 Beds
- 3 Baths
- 3,311 Sq Ft
7300 Old Boonesboro Rd, Winchester, KY 40391

This beautiful home sits on over 7 acres of peaceful countryside. Bring your horse! The back portion of the land is completely fenced. The private outdoor space includes a huge deck with a lovely view and an inviting covered front porch. The backyard would make the perfect space for your own dream swimming pool. Since the property has a 3-car detached garage; a 2-car attached garage plus a 1275

Vickie Skeens RE/MAX Elite Lexington

7300 Old Boonesboro Rd, Winchester, KY 40391
/21
$430,000

Sold Mar 09, 2026

870 Pilot View Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,568 Sq Ft
- Built 2022
Last Sold Summary
- 2% Below List Price
- $274/SF
- 31 Days On Market
Current Estimated Value $464,230

Last Listing Agent Chelsea Morguson McCallie Real Estate

870 Pilot View Rd, Winchester, KY 40391

/60
Est $407,517

Not Listed For Sale

405 Boone Ave, Winchester, KY 40391
- 3 Beds
- 4 Baths
- 2,718 Sq Ft
- Built 1945
405 Boone Ave, Winchester, KY 40391

Last Sold Summary
- 16 Days On Market
Last Listing Agent Diane K Scott The Brokerage

/4
$635,000

New Construction
- 4 Beds
- 2.5 Baths
- 2,537 Sq Ft
422 Alexis Way, Winchester, KY 40391

Introducing the Denver, a gorgeous all-brick ranch home offering 4 bedrooms and 2.5 baths, designed for both luxury and practicality. With its stunning curb appeal, front porch, and beam accents, this home makes a lasting first impression. Inside, the split-bedroom layout offers privacy and space for everyone, with a large primary suite featuring a walk-in closet, soaking tub, separate shower,

Shane Underwood Keller Williams Commonwealth

422 Alexis Way, Winchester, KY 40391
/29
$235,000

Sold Feb 09, 2026

142 Sturbridge Ln, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,220 Sq Ft
- Built 2005
Last Sold Summary
- 6% Below List Price
- $193/SF
- 1 Day On Market
Current Estimated Value $245,874

Last Listing Agent Donna Mink Mink Realty

142 Sturbridge Ln, Winchester, KY 40391

/57
Est $301,534

Not Listed For Sale

10 Northern Ave, Winchester, KY 40391
- 4 Beds
- 3 Baths
- 2,270 Sq Ft
- Built 1957
10 Northern Ave, Winchester, KY 40391

Last Sold Summary
- 0 Days On Market
Last Listing Agent Jeanne Beaven Rector Hayden Realtors

/2
$110,000
- Land
- 21,780 Sq Ft
- $220,000 per Acre
260 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

260 Duclair Dr, Winchester, KY 40391
/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 $358,398

Last Listing Agent Kymberly McCreary eXp Realty, LLC

418 Skylark Dr, Winchester, KY 40391

/92
Est $396,512

Not Listed For Sale

31 Mockingbird Valley Rd, Winchester, KY 40391
- 4 Beds
- 2 Baths
- 2,520 Sq Ft
- Built 1962
31 Mockingbird Valley Rd, Winchester, KY 40391

Last Sold Summary
- 209 Days On Market
Last Listing Agent Josh Wood Freedom Realty & Property Management

/12
$264,900

$40K PRICE DROP Pending
- 5 Beds
- 2 Baths
- 2,214 Sq Ft
55 Hillcrest Dr, Winchester, KY 40391

**Don't miss this exciting opportunity to pick out the new flooring for the basement and kitchen with a full price offer.****New roof (8 months old), one year old AC and heating unit, new large storage shed, and one year old wooden fence All of the expensive upgrades have been done. Come make this home your own. All-brick ranch with a full walk-out basement! This charming home offers excellent

Nina Vanetten RE/MAX Elite Lexington

55 Hillcrest Dr, Winchester, KY 40391
/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 $773,511

Last Listing Agent Alysia Niva Century 21 Advantage Realty - Georgetown

1700 Cabin Creek Rd, Winchester, KY 40391

/28
Est $379,662

Not Listed For Sale

29 Manor Dr, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 2,148 Sq Ft
- Built 1962
29 Manor Dr, Winchester, KY 40391

Last Sold Summary
- 247 Days On Market
Last Listing Agent John Patterson Rector Hayden Realtors

/16
$168,500

$21K PRICE DROP
- 3 Beds
- 1 Bath
- 950 Sq Ft
41 Hiawatha Trail, Winchester, KY 40391

Great Opportunity for First-Time Homebuyers! This charming 3-bedroom, 1-bath home features beautiful hardwood floors, an updated kitchen, and a fenced backyard perfect for relaxing, entertaining, or pets. Move-in ready and full of value, this is a wonderful opportunity to own a home with both character and convenience. Schedule your showing today!

Hannah Toole Coldwell Banker McMahan

41 Hiawatha Trail, Winchester, KY 40391
/32
$217,500

Sold Jul 13, 2026

525 Colby Ridge Blvd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,197 Sq Ft
- Built 2001
Last Sold Summary
- 1% Below List Price
- $182/SF
- 11 Days On Market
Current Estimated Value $220,426

Last Listing Agent Craig Bridgewater Bridgewater Real Estate

525 Colby Ridge Blvd, Winchester, KY 40391

/35
Est $370,059

Not Listed For Sale

121 Hampton Ave, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 2,248 Sq Ft
- Built 1958
121 Hampton Ave, Winchester, KY 40391

Last Sold Summary
- 60 Days On Market
Last Listing Agent Patrick Arvin Keller Williams Commonwealth

/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
/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 $240,082

Last Listing Agent Josh Wood Freedom Realty & Property Management

133 S Burns Ave, Winchester, KY 40391

/50
Est $428,159

Not Listed For Sale

33 Hampton Ave, Winchester, KY 40391
- 4 Beds
- 3 Baths
- 3,580 Sq Ft
- Built 1958
33 Hampton Ave, Winchester, KY 40391

Last Sold Summary
- 16 Days On Market
Last Listing Agent Robert Coburn Kentucky Realty Group, LLC

/21
$326,000

$1K PRICE INCREASE Pending
- Land
- 48.54 Acres
- $6,716 per Acre
380 Howard Creek Rd Unit 380, Winchester, KY 40391

Escape to the peace and privacy of this beautiful 48.54-acre unimproved property in a remote rural setting. Featuring a mix of rolling pasture and wooded acreage with gentle slopes, this versatile tract is ideal for farming, cattle, horses, recreation, hunting, or building your dream country retreat. Whether you're looking for productive agricultural land or a private getaway, this property

Kathy Burton Coldwell Banker McMahan

380 Howard Creek Rd Unit 380, Winchester, KY 40391
/62
$260,000

Sold Jun 09, 2026

144 Holly Ave, Winchester, KY 40391
- 8 Beds
- 5 Baths
- 3,637 Sq Ft
- Built 2001
Last Sold Summary
- 19% Below List Price
- $71/SF
- 69 Days On Market
Current Estimated Value $270,427

Last Listing Agent Shane Underwood Keller Williams Commonwealth

144 Holly Ave, Winchester, KY 40391

/27
Est $242,757

Not Listed For Sale

118 Southern Ct, Winchester, KY 40391
- 4 Beds
- 1.5 Baths
- 1,598 Sq Ft
- Built 1943
118 Southern Ct, Winchester, KY 40391

Last Sold Summary
- 31 Days On Market
Last Listing Agent Susan Baldwin Threshold Real Estate Services

/4
$10,000

$15K PRICE DROP Pending
- 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
/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 $251,127

Last Listing Agent Brooke Martin RO&CO Real Estate

204 Moss Ct, Winchester, KY 40391

/46
Est $333,144

Not Listed For Sale

14 Western Ave, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,676 Sq Ft
- Built 2023
14 Western Ave, Winchester, KY 40391

Last Sold Summary
- 79 Days On Market
Last Listing Agent Dale Hatton Dream Maker Realty, LLC

/7
$150,000

$30K PRICE DROP
- 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
/26
$390,000

Sold Jul 22, 2026

178 Hawthorne Dr, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 2,156 Sq Ft
- Built 2018
Last Sold Summary
- $181/SF
- 6 Days On Market
Current Estimated Value $392,941

Last Listing Agent Tiffani Casey Waizenhofer Real Estate

178 Hawthorne Dr, Winchester, KY 40391

/18
Est $200,529

Not Listed For Sale

6 Western Ave, Winchester, KY 40391
- 2 Beds
- 2 Baths
- 2,109 Sq Ft
- Built 1950
6 Western Ave, Winchester, KY 40391

Last Sold Summary
- 46 Days On Market
Last Listing Agent Steven G King CENTURY 21 Advantage Realty

/27
$234,900
- 3 Beds
- 2 Baths
- 1,108 Sq Ft
227 Leslie Dr, Winchester, KY 40391

This 3 Bedroom, 2 bath home is quietly nestled within the Saddle Brook subdivision. Conveniently located just outside of Winchester New Bypass, this property also qualifies for zero down rural housing financing. Updates can be seen throughout along with spacious master bedroom with on-suite, large back yard and open concept living. Schedule your showing today!

Michael Hilario The Agency

227 Leslie Dr, Winchester, KY 40391
/43
$450,000

Sold May 26, 2026

222 Ashton Oak Way, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 3,444 Sq Ft
- Built 2006
Last Sold Summary
- $131/SF
- 4 Days On Market
Current Estimated Value $439,079

Last Listing Agent Mila Ensor Ensor Real Estate, LLC

222 Ashton Oak Way, Winchester, KY 40391

/37
Est $284,018

Not Listed For Sale

120 Milwood Dr, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,853 Sq Ft
- Built 1965
120 Milwood Dr, Winchester, KY 40391

Last Sold Summary
- 80 Days On Market
Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

/38
$285,000

$5K PRICE INCREASE Pending
- 3 Beds
- 2 Baths
- 1,955 Sq Ft
108 Milwood Dr, Winchester, KY 40391

Welcome to 108 Milwood Drive\! Nestled in one of Winchester's most desirable neighborhoods, this well\-maintained 3\-bedroom, 2\-bath ranch offers a functional floor plan and peaceful backyard setting\. The spacious living room features a gas log fireplace, while the primary suite includes a private en suite bath\. A cozy den opens to a wooden deck overlooking the fenced backyard and wooded

Laura Disney Disney & Company

108 Milwood Dr, Winchester, KY 40391
/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 $229,579

Last Listing Agent Josh Wood Freedom Realty & Property Management

19 Cherokee Ct, Winchester, KY 40391

/26
Est $266,176

Not Listed For Sale

134 Boone Ave, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,878 Sq Ft
- Built 1920
134 Boone Ave, Winchester, KY 40391

Last Sold Summary
- 74 Days On Market
Last Listing Agent Steve Lindsey CENTURY 21 Commonwealth Real Estate

/14
$152,500

$7K PRICE DROP Pending
- Land
- 2.66 Acres
- $57,374 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
/36
$202,000

Sold Mar 18, 2026

58 Hughes Ave, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,456 Sq Ft
Last Sold Summary
- 6% Below List Price
- $139/SF
- 15 Days On Market
Current Estimated Value $193,219

Last Listing Agent E Anthony Phillips RE/MAX Creative Realty

58 Hughes Ave, Winchester, KY 40391

/32
Est $257,417

Not Listed For Sale

13 Euclid Ave, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,893 Sq Ft
- Built 1917
13 Euclid Ave, Winchester, KY 40391

Last Sold Summary
- 75 Days On Market
Last Listing Agent Jim Woodrum RE/MAX Creative, Winchester

/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
/39
$395,000

Sold Jun 18, 2026

18 Casa Landa Way, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,883 Sq Ft
- Built 1975
Last Sold Summary
- $210/SF
- 0 Days On Market
Current Estimated Value $395,130

Last Listing Agent Steve Charles Freedom Realty & Property Management

18 Casa Landa Way, Winchester, KY 40391

/45
Est $433,271

Not Listed For Sale

142 College St, Winchester, KY 40391
- 4 Beds
- 3 Baths
- 3,012 Sq Ft
- Built 1940
142 College St, Winchester, KY 40391

Last Sold Summary
- 87 Days On Market
Last Listing Agent Patrick Arvin Keller Williams Commonwealth

Showing Results 641 - 680, Page 17 of 18

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Clark County, KY Homes

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