Clark County, KY Homes

/26
$184,000
- 2 Beds
- 1.5 Baths
- 1,102 Sq Ft
356 Colby Ridge Blvd, Winchester, KY 40391

This cozy 2-bedroom, 1.5-bath home is the perfect fit for first-time buyers or anyone looking to expand their investment portfolio. The inviting living room features a propane-operated fireplace that provides a reliable backup heat source. The spacious primary bedroom includes his-and-her closets, and both bedrooms are equipped with additional split units for personalized comfort. A full

Nena Honaker Tom Goebel & Company

356 Colby Ridge Blvd, Winchester, KY 40391
/35
$248,000 Sold May 22, 2025

206 Moss Cir, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,773 Sq Ft
- Built 1997
Last Sold Summary
- 6% Below List Price
- $140/SF
- 20 Days On Market
Current Estimated Value $259,201

Last Listing Agent David Baesler Kentucky Dreams Realty

206 Moss Cir, Winchester, KY 40391

/31
Est $217,968 Not Listed For Sale

208 Locust Grove Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,494 Sq Ft
- Built 1950
208 Locust Grove Rd, Winchester, KY 40391

Last Sold Summary
- 6% Above List Price
- $137/SF
- 9 Days On Market
Last Sold Price $205,000

Last Listing Agent Shane Underwood Keller Williams Commonwealth

/43
$269,000
- 3 Beds
- 2 Baths
- 1,960 Sq Ft
564 Trapp-Goffs Corner Rd, Winchester, KY 40391

Private 12-Acre Property in Winchester, KY - Convenient to Lexington & Red River Gorge This 3-bedroom, 2-bath single-family home with an office/flex room is situated on 12 acres in Winchester, KY, offering a combination of open and primarily wooded land. The property is located less than 40 minutes from Lexington and approximately 30 minutes from Red River Gorge. The home offers 1,960 square feet

Felicia Mayes The Real Estate Co.

564 Trapp-Goffs Corner Rd, Winchester, KY 40391
/3
$554,651 Sold Jul 10, 2025

426 Alexis Way, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 2,400 Sq Ft
- Built 2024
Last Sold Summary
- 4% Above List Price
- $231/SF
- 21 Days On Market
Current Estimated Value $548,631

Last Listing Agent Shane Underwood Keller Williams Commonwealth

426 Alexis Way, Winchester, KY 40391

/18
Est $160,331 Not Listed For Sale

108 Crawford Ave, Winchester, KY 40391
- 2 Beds
- 1 Bath
- 900 Sq Ft
- Built 1955
108 Crawford Ave, Winchester, KY 40391

Last Sold Summary
- 23% Above List Price
- $144/SF
- 0 Days On Market
Last Sold Price $130,000

Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

/103
$3,500,000
- 6 Beds
- 5.5 Baths
- 7,274 Sq Ft
5045 Van Meter Rd, Winchester, KY 40391

Welcome to a truly exceptional 78-acre estate, where luxury and nature converge. This custom-built, three-story home, completed in 2006 , offers 7274 sq ft of meticulously designed living space. With 6 bedrooms and 5.5 bathrooms, there's ample room for family and guests. The impressive 2432 sq ft, temperature-controlled 5-car garage provides extensive space for vehicles and hobbies. Beyond the

The Prather Team - Michael Prather Keller Williams Bluegrass Realty

5045 Van Meter Rd, Winchester, KY 40391
/48
$341,500 Sold Jun 27, 2025

401 Cedar Ct, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,834 Sq Ft
- Built 1996
Last Sold Summary
- 1% Above List Price
- $186/SF
- 2 Days On Market
Current Estimated Value $348,268

Last Listing Agent Geneva Wilder Stewart & Co Realty LLC

401 Cedar Ct, Winchester, KY 40391

/10
Est $196,134 Not Listed For Sale

24 Fairview Ave, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,265 Sq Ft
- Built 1940
24 Fairview Ave, Winchester, KY 40391

Last Sold Summary
- 23% Above List Price
- $126/SF
- 1 Day On Market
Last Sold Price $159,900

Last Listing Agent Sondra Clark Taylor Real Estate, LLC

/2
$85,000 Pending
- Land
- 3.68 Acres
- $23,098 per Acre
2465 Flanagan Station Rd, Winchester, KY 40391

Rare opportunity to own 3.68 acres of vacant land just outside Winchester, ideal for buyers seeking space to build a private custom home in a peaceful rural setting. With electric and water available at the road, this property offers a ready-to-build homesite while maintaining the privacy and open surroundings many buyers are looking for today. Providing quick access to downtown Winchester's

Shari Frasure Keller Williams Commonwealth

2465 Flanagan Station Rd, 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 $618,608

Last Listing Agent Natalie Avant Berkshire Hathaway HomeServices Foster Realtors

4560 Pine Ridge Rd, Winchester, KY 40391

/55
Est $182,253 Not Listed For Sale

30 Ashland Ave, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,416 Sq Ft
- Built 1983
30 Ashland Ave, Winchester, KY 40391

Last Sold Summary
- 9% Above List Price
- $118/SF
- 8 Days On Market
Last Sold Price $166,500

Last Listing Agent Christa Joynt Keller Williams Commonwealth

/2
$100,000
- Land
- 0.37 Acre
- $270,270 per Acre
225 Jacob Ct, 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

225 Jacob Ct, Winchester, KY 40391
/32
$263,000 Sold Sep 05, 2025

2 Chickadee Ln, Winchester, KY 40391
- 3 Beds
- 1.5 Baths
- 1,397 Sq Ft
- Built 1960
Last Sold Summary
- 1% Above List Price
- $188/SF
- 2 Days On Market
Current Estimated Value $256,602

Last Listing Agent Ashley Spencer Keller Williams Commonwealth

2 Chickadee Ln, Winchester, KY 40391

/30
Est $176,013 Not Listed For Sale

370 E Washington St, Winchester, KY 40391
- 2 Beds
- 1 Bath
- 1,126 Sq Ft
- Built 1930
370 E Washington St, Winchester, KY 40391

Last Sold Summary
- 17% Above List Price
- $133/SF
- 3 Days On Market
Last Sold Price $150,000

Last Listing Agent Meredith Story Story Realty

/2
$195,000
6699 Boonesboro Rd, Winchester, KY 40391

READY TO BUILD OR HUNT? We have the perfect spot for you! Mostly wooded 8.35 acres, tract 2B, of green, treed, Bluegrass Heaven. Close proximity to I 75 and I 64 as well as Lexington, Richmond, and Winchester. Bring your own builder or we can help you find one!

Jennifer Ray RE/MAX Elite Lexington

6699 Boonesboro Rd, Winchester, KY 40391
/35
$325,000 Sold Nov 21, 2025

130 Hibiscus Ln, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 1,900 Sq Ft
- Built 2000
Last Sold Summary
- 7% Below List Price
- $171/SF
- 19 Days On Market
Current Estimated Value $334,469

Last Listing Agent Ashley Barreto Indigo & Co

130 Hibiscus Ln, Winchester, KY 40391

/32
Est $193,923 Not Listed For Sale

203 Crawford Ct, Winchester, KY 40391
- 2 Beds
- 2 Baths
- 1,900 Sq Ft
- Built 1960
203 Crawford Ct, Winchester, KY 40391

Last Sold Summary
- 12% Above List Price
- $91/SF
- 17 Days On Market
Last Sold Price $173,000

Last Listing Agent Andrew Fugitt Coldwell Banker McMahan

/3
$670,000 New Construction
- 3 Beds
- 2 Baths
- 2,261 Sq Ft
113 Bella Shae Way, Winchester, KY 40391

Introducing the Hampton, a beautiful all-brick ranch home. This 3-bedroom, 2-bath split-bedroom design offers both privacy and comfort. The spacious primary suite is a true retreat, featuring a luxurious ensuite with double vanities, a walk-in shower, and dual walk-in closets. The open-concept kitchen and great room are perfect for entertaining, highlighted by a gas log fireplace, a large kitchen

Shane Underwood Keller Williams Commonwealth

113 Bella Shae Way, Winchester, KY 40391
/51
$303,000 Sold Jan 16, 2026

22 N Bloomfield Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,913 Sq Ft
- Built 1919
Last Sold Summary
- 5% Below List Price
- $158/SF
- 16 Days On Market
Current Estimated Value $302,839

Last Listing Agent Libby VanMeter Marshall Lane Real Estate - Lexington

22 N Bloomfield Rd, Winchester, KY 40391

/53
Est $208,774 Not Listed For Sale

29 Fairview Ave, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,631 Sq Ft
- Built 1960
29 Fairview Ave, Winchester, KY 40391

Last Sold Summary
- 111% Above List Price
- $61/SF
- 140 Days On Market
Last Sold Price $99,000

Last Listing Agent Bob Sophiea eXp Realty, LLC

/100
$429,900
- 4 Beds
- 2.5 Baths
- 1,500 Sq Ft
240 Athens Boonesboro Rd, Winchester, KY 40391

Rare Investment Opportunity on the Kentucky River! Two incredible homes on 3 beautiful acres — endless potential awaits. Live in the charming log cabin and let the second home pay the mortgage with its long term, reliable tenant already in place. This property offers room to dream: -Build a future campground -Create a private riverside retreat -Expand for additional rentals -Or simply enjoy your

Darrell Tackett Dream Maker Realty, LLC

240 Athens Boonesboro Rd, Winchester, KY 40391
/23
$244,895 Sold Jun 10, 2025

244 Bay Hill Ct, Winchester, KY 40391
- 3 Beds
- 3 Baths
- 2,536 Sq Ft
- Built 2006
Last Sold Summary
- 2% Below List Price
- $97/SF
- 10 Days On Market
Current Estimated Value $267,697

Last Listing Agent Destiny Darby Keller Williams Commonwealth

244 Bay Hill Ct, Winchester, KY 40391

/29
Est $164,276 Not Listed For Sale

4 Sylvania Ave, Winchester, KY 40391
- 2 Beds
- 1 Bath
- 832 Sq Ft
- Built 1960
4 Sylvania Ave, Winchester, KY 40391

Last Sold Summary
- 17% Above List Price
- $168/SF
- 4 Days On Market
Last Sold Price $140,000

Last Listing Agent Christal Browning Four Seasons Realty

/84
$799,900
- 4 Beds
- 3.5 Baths
- 4,922 Sq Ft
2509 Mount Sterling Rd, Winchester, KY 40391

Embrace Bluegrass living with this beautiful fieldstone ranch on 10+ acres in the heart of horse country. Just minutes from interstate access, yet surrounded by rolling hills and scenic views, this mini farm offers a larger barn with 6 stalls, including water and electric connection, 90 foot roof hangover on the barn, 5 paddocks, each with their own gate and water ran along each paddock. The home

Josh Wood Freedom Realty & Property Management

2509 Mount Sterling Rd, Winchester, KY 40391
/2
$89,000 Sold Dec 18, 2025

13067 Irvine Rd, Winchester, KY 40391
- Land
- 7.86 Acres
- $11,323 per Acre
Last Sold Summary
- 78 Days On Market
Last Listing Agent Mendel Tipton Natural Bridge Realty

13067 Irvine Rd, Winchester, KY 40391

/22
Est $182,326 Not Listed For Sale

21 Sylvania Ave, Winchester, KY 40391
- 2 Beds
- 1 Bath
- 1,016 Sq Ft
- Built 1970
21 Sylvania Ave, Winchester, KY 40391

Last Sold Summary
- 17% Above List Price
- $154/SF
- 1 Day On Market
Last Sold Price $156,000

Last Listing Agent Ciara Isaacs Hagedorn RE/MAX

/2
$100,000
- Land
- 1.1 Acres
- $90,909 per Acre
270 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

270 Duclair Dr, Winchester, KY 40391
/2
$4,900,000 Sold Dec 23, 2025

175 Chatham Place, Winchester, KY 40391
- 2 Beds
- 3 Baths
- 37,192 Sq Ft
- Built 2007
Last Sold Summary
- 13% Below List Price
- $132/SF
- 111 Days On Market
Current Estimated Value $4,910,294

Last Listing Agent Garry Milton Milton and Associates Real Estate

175 Chatham Place, Winchester, KY 40391

/30
Est $198,797 Not Listed For Sale

280 Winn Ave, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,432 Sq Ft
- Built 1960
280 Winn Ave, Winchester, KY 40391

Last Sold Summary
- 28% Above List Price
- $108/SF
- 3 Days On Market
Last Sold Price $155,000

Last Listing Agent Whitney Ensor Ensor Real Estate, LLC

/9
$500,000
- Land
- 1.52 Acres
- $328,947 per Acre
1005 Early Dr, Winchester, KY 40391

Visibility, Access, Utilities on site per seller/per plat-buyer to verify, zoned B-3. 1.52 acres located at I-64 exit 96, Right in front of the Hampton Inn, buyer to verify and satisfy themselves to all aspects and information on property. and inspections sold as is. Buyer to Check with all utilities companies to very water electric and gas availability and locations on all utilities.

Whitney Ensor Ensor Real Estate, LLC

1005 Early Dr, Winchester, KY 40391
/51
$340,000 Sold Oct 30, 2025

356 Boone Ave, Winchester, KY 40391
- 4 Beds
- 3 Baths
- 3,200 Sq Ft
- Built 1940
Last Sold Summary
- 5% Below List Price
- $106/SF
- 30 Days On Market
Current Estimated Value $344,847

Last Listing Agent Elizabeth Hodge Lifstyl Real Estate

356 Boone Ave, Winchester, KY 40391

/25
Est $110,880 Not Listed For Sale

248 Cook Ave, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,465 Sq Ft
- Built 1940
248 Cook Ave, Winchester, KY 40391

Last Sold Summary
- 122% Above List Price
- $34/SF
- 27 Days On Market
Last Sold Price $50,000

Last Listing Agent Chris Johnson Plum Tree Realty

/14
$650,000
- Land
- 3 Acres
- $216,667 per Acre
205 Codella Dr, Winchester, KY 40391

Great opportunity to buy and build just off the Winchester Bypass. This property is nicely located in the midst of a great deal of new development including a brand new, state-of-the-art CHI Saint Joseph Health Center. Other new development in the immediate area includes Zips Car Wash and Domino's Pizza. Additionally, Walmart and Kroger are located directly across the Bypass from this site. See

Greg Leveridge Block + Lot Real Estate

205 Codella Dr, Winchester, KY 40391
/28
$131,000 Sold Mar 12, 2026

46 Judy Ann Ct, Winchester, KY 40391
- 2 Beds
- 1.5 Baths
- 960 Sq Ft
Last Sold Summary
- 3% Below List Price
- $136/SF
- 0 Days On Market
Current Estimated Value $148,072

Last Listing Agent Lukas Owens The Brokerage

46 Judy Ann Ct, Winchester, KY 40391

/4
Est $96,967 Not Listed For Sale

Unlisted Address
- 2 Beds
- 1 Bath
- 940 Sq Ft
- Built 1940
Unlisted Address

Last Sold Summary
- 203% Above List Price
- $34/SF
Last Sold Price $32,000

Last Listing Agent Null Non-Member Non-Member Office

/109
$1,600,000
- 5 Beds
- 3 Baths
- 7,172 Sq Ft
351 Benton Rd, Mount Sterling, KY 40353

Set on 27± fully fenced acres of pristine Kentucky countryside, this custom-built luxury home exudes sophistication from the moment you arrive. Every inch has been thoughtfully designed with premium materials, refined finishes, and an effortless sense of elegance, offering privacy, space, and an unmatched lifestyle. Inside, the split floor plan opens into an expansive main living area highlighted

Courtney Mangold The Agency

351 Benton Rd, Mount Sterling, KY 40353
/4
$315,000 Sold Jun 30, 2025

4550 Schollsville Rd Unit 40391, Winchester, KY 40391
Last Sold Summary
- 2 Days On Market
Last Listing Agent Mila Ensor Ensor Real Estate, LLC

4550 Schollsville Rd Unit 40391, Winchester, KY 40391

/41
Est $201,360 Not Listed For Sale

31 Watts Rd, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,343 Sq Ft
- Built 1960
31 Watts Rd, Winchester, KY 40391

Last Sold Summary
- 1% Above List Price
- $149/SF
- 24 Days On Market
Last Sold Price $200,000

Last Listing Agent Christa Joynt Keller Williams Commonwealth

/2
$67,500
- Land
- 1.89 Acres
- $35,695 per Acre
250 Spencer Ln, Winchester, KY 40391

Unique triangular shaped lot in a wooded rural setting, interesting opportunities for privacy in a beautiful area of Clark County where you can enjoy the outdoors and create memories galore.

Craig Bridgewater Bridgewater Real Estate

250 Spencer Ln, Winchester, KY 40391

Showing Results 281 - 320, Page 8 of 18

Kentucky Clark County

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