Winchester, KY Homes

/2
$10,000
- Land
- 0.06 Acre
- $166,667 per Acre
75 4th St, Winchester, KY 40391

Explore the opportunity to build your next home or investment property on this 0.06-acre residential lot located at 75 4th Street. Nestled in an established neighborhood, this lot offers convenient access to local amenities, schools, and nearby roadways. With public utilities available in the area, it's a great option for new construction or future development. Whether you're a builder, investor,

Bob Sophiea eXp Realty, LLC

75 4th St, 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 $228,354

Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

301 Cabin Creek Heights, Winchester, KY 40391

/56
Est $644,935 Not Listed For Sale
- 6 Beds
- 2.5 Baths
- 3,800 Sq Ft
9953 Ironworks Rd, Winchester, KY 40391

9953 Ironworks Rd, Winchester, KY 40391

/2
$110,000
- Land
- 0.47 Acre
- $234,043 per Acre
139 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

139 Jacob Ct, 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

/26
Est $321,927 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 2,668 Sq Ft
11705 Irvine Rd, Winchester, KY 40391

11705 Irvine Rd, Winchester, KY 40391

/32
$249,900
- 3 Beds
- 2 Baths
- 1,904 Sq Ft
528 Estes Dr, Winchester, KY 40391

Don't miss out on seeing this 3/2 brick ranch home in a convenient location to shopping, dining, parks, pool and more. Large open family room and kitchen with bamboo flooring. The kitchen has a large granite counter top island with newer stainless appliances and a gas range. This home is complete with an Aurora above ground pool for all the summer fun. The seller has already planted garden

Josh Wood Freedom Realty & Property Management

528 Estes Dr, 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 $284,711

Last Listing Agent Teresa Richmond Freedom Realty & Property Management

225 Prescott Ln, Winchester, KY 40391

/33
Est $309,824 Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,592 Sq Ft
510 Wills Rupard Rd, Winchester, KY 40391

510 Wills Rupard Rd, Winchester, KY 40391

/2
$882,000
- Land
- 3.93 Acres
- $224,427 per Acre
Lot 1 - 12 Plantations Dr, Winchester, KY 40391

NOW SELLING PHASE ONE: 12 Buildable Lots (minimum lot is 9600+ sqft) of PHASE ONE of Deerlawn's Development located at 2395 Paris Rd (Parent Listing). Earmarked as Winchester, Ky's most anticipated residential development consisting of an ambitious 274+-acre expansion formerly known as the well-established Royal Oaks/Plantation neighborhoods, Phase One has 12 lots ready for you to build your New

Melia Hord Keller Williams Legacy Group

Lot 1 - 12 Plantations Dr, Winchester, KY 40391
/32
$235,000 Sold Jan 31, 2025

603 Westmeade Dr, Winchester, KY 40391
- 4 Beds
- 2 Baths
- 1,866 Sq Ft
- Built 1977
Last Sold Summary
- 13% Below List Price
- $126/SF
- 49 Days On Market
Current Estimated Value $264,057

Last Listing Agent Patrick Arvin Keller Williams Commonwealth

603 Westmeade Dr, Winchester, KY 40391

/33
Est $253,204 Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,400 Sq Ft
7344 Ironworks Rd, Winchester, KY 40391

7344 Ironworks Rd, Winchester, KY 40391

/2
$150,000
- Land
- 2.11 Acres
- $71,090 per Acre
125 Knox 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

125 Knox Ct, Winchester, KY 40391
/49
$442,500 Sold Apr 18, 2025

321 Frontier Way, Winchester, KY 40391
- 6 Beds
- 3.5 Baths
- 3,882 Sq Ft
- Built 2005
Last Sold Summary
- 10% Below List Price
- $114/SF
- 134 Days On Market
Current Estimated Value $440,782

Last Listing Agent Olivia White Deborah Ball Realty

321 Frontier Way, Winchester, KY 40391

/82
Est $363,475 Not Listed For Sale
- 3 Beds
- 2 Baths
- 3,173 Sq Ft
380 L E Junction Rd, Winchester, KY 40391

380 L E Junction Rd, Winchester, KY 40391

/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
/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 $192,092

Last Listing Agent Dale Hatton Dream Maker Realty, LLC

605 Dixiana Dr, Winchester, KY 40391

/51
Est $476,993 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,841 Sq Ft
5600 Ecton Rd, Winchester, KY 40391

5600 Ecton Rd, Winchester, KY 40391

/92
$1,200,000 Pending
- 5 Beds
- 7 Baths
- 8,236 Sq Ft
6237 Bybee Rd, Winchester, KY 40391

Step into timeless elegance with this breathtaking modern Victorian-style masterpiece, perfectly positioned on 4.39 acres with panoramic views of sunrises, sunsets, and distant mountains. Designed and built by Tom Padgett, this home is rich in character and detail—from hand-hewn wood beam ceilings to Waterford crystal chandeliers. The grand 2-story foyer welcomes you into a flowing layout that

Amanda Marcum Berkshire Hathaway HomeServices Foster Realtors

6237 Bybee Rd, 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 $345,710

Last Listing Agent Jo Gawthrop Keller Williams Bluegrass Realty

219 Hampton Ave, Winchester, KY 40391

/38
Est $398,747 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,866 Sq Ft
3070 Goshen Rd, Winchester, KY 40391

3070 Goshen Rd, Winchester, KY 40391

/17
$129,900
- 2 Beds
- 1 Bath
- 876 Sq Ft
122 Calloway St, Winchester, KY 40391

Investment Opportunity or Perfect Starter Home This charming 2-bedroom, 1-bath property is full of potential! With a strong rental history and an excellent lease track record, it's ideal for investors or first-time buyers. Recently vacated, the home requires only light maintenance, and the seller is even willing to fund minor repairs. Don't miss your chance to own a property with great value and

Darrell Tackett Dream Maker Realty, LLC

122 Calloway St, 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 $826,668

Last Listing Agent Emily Miller Bluegrass Sotheby's International Realty

2158 Venable Rd, Winchester, KY 40391

/32
Est $314,347 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,260 Sq Ft
810 Howard Creek Rd, Winchester, KY 40391

810 Howard Creek Rd, Winchester, KY 40391

/22
$167,500 Pending
- 3 Beds
- 1 Bath
- 1,274 Sq Ft
146 Cook Ave, Winchester, KY 40391

Sellers willing to pay towards closing cost! Welcome to 146 Cook Avenue in Winchester, Kentucky — an updated home combining classic charm with modern style. This 3-bedroom, 1-bath property offers around 1,274 sq. ft. of comfortable living space with an open-concept layout, newer flooring throughout, and a completely renovated kitchen. The tiled bathroom includes space for a washer and dryer, and

Autumn Johannes National Real Estate

146 Cook Ave, Winchester, KY 40391
/38
$221,700 Sold Feb 10, 2025

104 Caudill Dr, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,952 Sq Ft
Last Sold Summary
- 15% Below List Price
- $114/SF
- 63 Days On Market
Current Estimated Value $257,401

Last Listing Agent Joshua Brown Mike Brown Real Estate & Auction Co, LLC

104 Caudill Dr, Winchester, KY 40391

/53
Est $301,436 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,126 Sq Ft
1489 White Conkwright Rd, Winchester, KY 40391

1489 White Conkwright Rd, Winchester, KY 40391

/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
/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
Last Listing Agent Josh Wood Freedom Realty & Property Management

227 Cross Brook Ln, Winchester, KY 40391

/23
Est $318,496 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,624 Sq Ft
440 White Conkwright Rd, Winchester, KY 40391

440 White Conkwright Rd, Winchester, KY 40391

/71
$419,000 Pending
- 4 Beds
- 2.5 Baths
- 2,388 Sq Ft
188 Big Stoner Rd, Winchester, KY 40391

48 hr kick-out- Come home every day to this 2-story beauty! You need country life? Well here is it! A little over 1 acre to spread out & enjoy the outdoors w/farm views & beautiful sunsets in the evening. This home opens up to a huge living room with hardwood floors and a vaulted ceiling. Kitchen has all stainless steel appliances & granite counter tops. First floor has a primary suite

Trina Penn RE/MAX Creative Realty

188 Big Stoner Rd, 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 $286,934

Last Listing Agent Jennifer Guyton White Realty, LLC

126 Ashley Dr, Winchester, KY 40391

/78
Est $576,509 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,689 Sq Ft
7625 Irvine Rd, Winchester, KY 40391

7625 Irvine Rd, Winchester, KY 40391

/4
$64,900
- Land
- 0.64 Acre
- $101,406 per Acre
102 Royal Oak Dr, Winchester, KY 40391

A Unique Opportunity to Build your Dream Home in the Estate Section of Royal Oaks in Clark County. Situated on..64 acres of land and Conveniently located off Exit 96 on I-64, with close proximity to the Industrial Park, Shopping, Dining and downtown Winchester. Call listing agent for additional details and information on the few lots left to build on in this subdivision!

Melia Hord Keller Williams Legacy Group

102 Royal Oak Dr, 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
Last Listing Agent Janna Smith United Real Estate Bluegrass

205 Chardonnay Ct, Winchester, KY 40391

/76
Est $479,282 Not Listed For Sale
- 5 Beds
- 3 Baths
- 1,623 Sq Ft
110 White Conkwright Rd, Winchester, KY 40391

110 White Conkwright Rd, Winchester, KY 40391

/8
$1,500,000
1015 Old Stone Church Rd, Winchester, KY 40391

Right off of Boonesboro Road lies 60.65± acres of Kentucky history waiting for its next chapter! This remarkable property sits along historic Howard's Creek and is located on the site of the original Bush Settlement—one of the earliest settlements in Kentucky. Formerly a working tobacco farm, this versatile acreage offers opportunities for cattle, hay, or crops, with timber and mineral rights

Walker Mack Bluegrass Property Exchange

1015 Old Stone Church 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 $212,058

Last Listing Agent Aaron Kendall Lifstyl Real Estate

305 Geronimo Ct, Winchester, KY 40391

/52
Est $353,684 Not Listed For Sale
- 4 Beds
- 1.5 Baths
- 2,340 Sq Ft
3282 Old Ruckerville Rd, Winchester, KY 40391

3282 Old Ruckerville Rd, Winchester, KY 40391

/87
$3,100,000
- 6 Beds
- 5 Baths
- 3,693 Sq Ft
3049 Ironworks Rd, Winchester, KY 40391

150 acres of pure Kentucky beauty in Winchester, on the market for the first time ever. This incredible cattle farm has been owned by the same family since 1803 and is now ready for its next chapter. With rolling land, four barns, two storage sheds, four ponds, a creek, and two homes, this estate is truly unmatched. If you've been waiting for your dream property, this is it.

Zova Rothchild Keller Williams Legacy Group

3049 Ironworks Rd, Winchester, KY 40391

Showing Results 81 - 120, Page 3 of 18

Kentucky Clark County Winchester

How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Homes in Nearby Neighborhoods

Homes in Nearby Cities

Homes in Nearby Counties

Homes in Nearby Zip Codes

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage