Winchester, KY Homes

/69
Est $368,739 Not Listed For Sale

3975 Wills Rupard Rd, Winchester, KY 40391
- 4 Beds
- 3 Baths
- 3,021 Sq Ft
- Built 1986
3975 Wills Rupard Rd, Winchester, KY 40391

Last Sold Summary
- 13% Above List Price
- $108/SF
- 218 Days On Market
Last Sold Price $325,000

Last Listing Agent Tonya Morrow KY Local

/36
$345,000 Pending
- 2 Beds
- 2 Baths
- 1,568 Sq Ft
208 Citation Ct, Winchester, KY 40391

One owner, all electric, 2 BR/2Ba ranch with a bonus room that could be an office or a third bedroom. Great for downsizing or first time homeowner! The open floor great room with ample windows to brighten it supports the handicapped features of the primary bedroom, primary bathroom, garage and more. Enjoy the large pantry off the kitchen area and the island that has room to slide a chair under.

Garnett Davis Tom Goebel & Company

208 Citation Ct, 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 $225,733

Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

301 Cabin Creek Heights, Winchester, KY 40391

/45
Est $402,673 Not Listed For Sale

1600 Crowe Ridge Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 2,846 Sq Ft
- Built 2012
1600 Crowe Ridge Rd, Winchester, KY 40391

Last Sold Summary
- 34% Above List Price
- $105/SF
- 147 Days On Market
Last Sold Price $300,000

Last Listing Agent Joyce Ratliff Tom Goebel & Company

/33
$299,500
- 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
$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

/56
Est $642,198 Not Listed For Sale

9953 Ironworks Rd, Winchester, KY 40391
- 6 Beds
- 2.5 Baths
- 3,800 Sq Ft
- Built 2003
9953 Ironworks Rd, Winchester, KY 40391

Last Sold Summary
- 1% Below List Price
- $171/SF
- 7 Days On Market
Last Sold Price $650,000

Last Listing Agent Tara Smith Keller Williams Commonwealth

/45
$325,000
- 3 Beds
- 2.5 Baths
- 1,900 Sq Ft
120 Pilot View Rd, Winchester, KY 40391

Charming 1930 farmhouse that perfectly blends timeless character with modern updates, situated on 5 beautiful acres. This fully remodeled home offers 3 bedrooms, 2.5 baths, and a spacious bonus room currently used as a home office. Inside, you'll find a formal dining room, updated living spaces, and a large laundry room where the washer and dryer convey. Major improvements include a new roof

Jennifer Parsons RE/MAX Elite Lexington

120 Pilot View Rd, 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 $285,906

Last Listing Agent Teresa Richmond Freedom Realty & Property Management

225 Prescott Ln, Winchester, KY 40391

/17
Est $492,552 Not Listed For Sale

1026 Crowe Ridge Rd, Winchester, KY 40391
- 1 Bath
- Built 1945
1026 Crowe Ridge Rd, Winchester, KY 40391

Last Sold Summary
- 13% Above List Price
- $407/SF
- 56 Days On Market
Last Sold Price $435,000

Last Listing Agent Sophia Herald Herald Real Estate

/70
$335,000 Pending
- 6 Beds
- 4 Baths
- 3,544 Sq Ft
297 S Main St, Winchester, KY 40391

Completely remodeled duplex offering over 3,400 sq. ft. of living space! Featuring 6 bedrooms and 4 bathrooms, this property has been fully updated with granite countertops, new appliances, fresh flooring, and paint throughout. The layout is bright and inviting with plenty of natural light. Enjoy the covered front porch, separate utility room, and unfinished basement for extra storage or future

Silvia Torres Tru Life Real Estate

297 S Main St, 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 $448,624

Last Listing Agent Olivia White Deborah Ball Realty

321 Frontier Way, Winchester, KY 40391

/26
Est $325,763 Not Listed For Sale

11705 Irvine Rd, Winchester, KY 40391
- 3 Beds
- 1.5 Baths
- 2,668 Sq Ft
- Built 1988
11705 Irvine Rd, Winchester, KY 40391

Last Sold Summary
- 48% Above List Price
- $82/SF
- 81 Days On Market
Last Sold Price $220,000

Last Listing Agent Matthew J. Reffett Re/Max Legacy Group - Paintsville

/38
$359,900 New Construction
- 4 Beds
- 4.5 Baths
3600 Crowe Ridge Rd, Winchester, KY 40391

Newly constructed unfinished multigenerational home located on 4 acres. Separate level living with 2 kitchens, 2 laundry rooms, and an en-suite for every bedroom. The main floor features 20' cathedral ceilings, 8' doors and 15 3'x6' windows creating a spacious home boasting panoramic views. Includes an additional 20'x24' loft space and 2 flex rooms with ANSI standard windows. Secondary living

Maggie Napier Napier Realtors

3600 Crowe Ridge Rd, 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 $193,900

Last Listing Agent Dale Hatton Dream Maker Realty, LLC

605 Dixiana Dr, Winchester, KY 40391

/33
Est $305,001 Not Listed For Sale

510 Wills Rupard Rd, Winchester, KY 40391
- 2 Beds
- 1 Bath
- 1,592 Sq Ft
- Built 1990
510 Wills Rupard Rd, Winchester, KY 40391

Last Sold Summary
- 69% Above List Price
- $114/SF
- 2 Days On Market
Last Sold Price $181,000

Last Listing Agent Joe Marcum CENTURY 21 Advantage Realty

/34
$325,000 Pending
- 4 Beds
- 3 Baths
- 1,776 Sq Ft
213 Orchid Ct, Winchester, KY 40391

Kasey McCarty 5.23 Real Estate

213 Orchid Ct, 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 $342,213

Last Listing Agent Jo Gawthrop Keller Williams Bluegrass Realty

219 Hampton Ave, Winchester, KY 40391

/33
Est $270,726 Not Listed For Sale

7344 Ironworks Rd, Winchester, KY 40391
- 2 Beds
- 1 Bath
- 1,400 Sq Ft
- Built 1925
7344 Ironworks Rd, Winchester, KY 40391

Last Sold Summary
- 24% Above List Price
- $156/SF
- 2 Days On Market
Last Sold Price $219,000

Last Listing Agent Jason Rainey Executive Real Estate, LLC

/50
$359,000 Pending
- 3 Beds
- 2 Baths
- 2,080 Sq Ft
175 Overlooking Dr, Winchester, KY 40391

Relax on your front porch and enjoy the view of the lake or have a barbecue on your oversized rear deck and enjoy the countryside views. This 3-bedroom, 2-bathroom home features Living Room, Dining Room, Family Room, has two cozy fireplaces for your entertainment. Home has a full partially finished basement with a large recreation room and plenty of space to add additional rooms if needed. To

Keith Wilson Coldwell Banker McMahan

175 Overlooking Dr, 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 $844,083

Last Listing Agent Emily Miller Bluegrass Sotheby's International Realty

2158 Venable Rd, Winchester, KY 40391

/82
Est $353,966 Not Listed For Sale

380 L E Junction Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 3,173 Sq Ft
- Built 1976
380 L E Junction Rd, Winchester, KY 40391

Last Sold Summary
- 9% Above List Price
- $102/SF
- 13 Days On Market
Last Sold Price $324,000

Last Listing Agent Davin Smith Caswell Prewitt Realty, Inc

/67
$325,000
- 3 Beds
- 3 Baths
- 2,821 Sq Ft
3622 Stamper Dr, Winchester, KY 40391

This lovely and unique home sits at the end of a quiet street in a secluded circle and backs up to a privacy fenced yard and greenspace right in the heart of town. Properties like this are hard to find and the unique amenities inside truly set this home apart. Step through the front door to discover a spacious great room with gleaming laminate floors and a brick fireplace; the perfect place to

Josh Wood Freedom Realty & Property Management

3622 Stamper Dr, 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
Current Estimated Value $283,032

Last Listing Agent Josh Wood Freedom Realty & Property Management

227 Cross Brook Ln, Winchester, KY 40391

/51
Est $476,392 Not Listed For Sale

5600 Ecton Rd, Winchester, KY 40391
- 3 Beds
- 3 Baths
- 2,841 Sq Ft
- Built 1992
5600 Ecton Rd, Winchester, KY 40391

Last Sold Summary
- 4% Above List Price
- $162/SF
- 62 Days On Market
Last Sold Price $460,000

Last Listing Agent Kymberly McCreary Keller Williams Commonwealth

/34
$300,000
- 2 Beds
- 1 Bath
- 1,531 Sq Ft
1508 Ford Hampton Rd, Winchester, KY 40391

Welcome home to this adorable 2 bedroom, 1 bathroom farmhouse on 5 peaceful acres. Inside, the layout is open and inviting with LVP and hardwood flooring throughout with a tiled bath. The kitchen and family room flow together and feature beautiful exposed wood beams that are hundreds of years old and reclaimed from an old church. A wood-burning stove in the family room adds warmth and character

Michelle Blackburn RE/MAX Creative, Winchester

1508 Ford Hampton 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 $288,858

Last Listing Agent Jennifer Guyton White Realty, LLC

126 Ashley Dr, Winchester, KY 40391

/38
Est $368,631 Not Listed For Sale

3070 Goshen Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 2,866 Sq Ft
- Built 1998
3070 Goshen Rd, Winchester, KY 40391

Last Sold Summary
- $128/SF
- 2 Days On Market
Last Sold Price $367,000

Last Listing Agent Kevin Bradley Keller Williams Legacy Group

/51
$775,000
- 5 Beds
- 3.5 Baths
- 2,904 Sq Ft
1783 Gay Evans Rd, Winchester, KY 40391

Welcome to your dream homestead retreat! Tucked away on 7.27 beautiful acres, this stunning 5-bedroom, 4-bath home offers the perfect blend of comfort, function, and country living. From the inviting front porch sunsets to the resort-style outdoor space, this property has everything you've been searching for. Step inside to the two story foyer that leads to an open-concept main level featuring

Lucy Martin Jenkins United Real Estate Bluegrass

1783 Gay Evans Rd, 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
Current Estimated Value $356,712

Last Listing Agent Janna Smith United Real Estate Bluegrass

205 Chardonnay Ct, Winchester, KY 40391

/32
Est $282,257 Not Listed For Sale

810 Howard Creek Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,260 Sq Ft
- Built 2001
810 Howard Creek Rd, Winchester, KY 40391

Last Sold Summary
- 7% Above List Price
- $210/SF
- 17 Days On Market
Last Sold Price $264,900

Last Listing Agent Serena Cassidy Coldwell Banker McMahan

/30
$215,000 Pending
- 3 Beds
- 2 Baths
- 1,456 Sq Ft
2721 Pretty Run Rd, Winchester, KY 40391

Back on market due to buyer financing, no fault of the seller! Situated on 5 scenic acres along a highly sought-after country road, this 3-bedroom, 2-bath property presents an excellent opportunity to create your dream rural retreat. The home features a functional layout with a spacious living area, an eat-in kitchen, and a primary suite with its own bath. Two additional bedrooms offer

Michelle Blackburn RE/MAX Creative, Winchester

2721 Pretty Run 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 $215,899

Last Listing Agent Aaron Kendall Lifstyl Real Estate

305 Geronimo Ct, Winchester, KY 40391

/53
Est $286,317 Not Listed For Sale

1489 White Conkwright Rd, Winchester, KY 40391
- 3 Beds
- 1.5 Baths
- 1,126 Sq Ft
- Built 1995
1489 White Conkwright Rd, Winchester, KY 40391

Last Sold Summary
- 4% Above List Price
- $244/SF
- 45 Days On Market
Last Sold Price $275,000

Last Listing Agent Sabina Chambers Semonin Realty

/100
$1,789,000
- 3 Beds
- 2.5 Baths
- 4,518 Sq Ft
3166 Colby Rd, Winchester, KY 40391

PRICE REDUCED and sellers are offering a 25,000 allowance at closing to spend as you wish!! Welcome to this beautiful 33± acre estate, offering the perfect blend of country charm, modern comfort, and endless opportunity. The stately historical home, built in 1919, retains timeless character and can be registered with the Historical Home Society. Enjoy stunning mountain views — located at one of

Alyssa M Boley Coldwell Banker McMahan

3166 Colby Rd, Winchester, KY 40391
/44
$320,000 Sold Nov 21, 2025

104 Teakwood Ct, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 1,970 Sq Ft
- Built 2005
Last Sold Summary
- 3% Below List Price
- $162/SF
- 24 Days On Market
Current Estimated Value $319,295

Last Listing Agent Jessica Noto Century 21 Advantage Realty - Georgetown

104 Teakwood Ct, Winchester, KY 40391

/23
Est $321,675 Not Listed For Sale

440 White Conkwright Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,624 Sq Ft
- Built 2004
440 White Conkwright Rd, Winchester, KY 40391

Last Sold Summary
- 31% Above List Price
- $151/SF
- 3 Days On Market
Last Sold Price $245,000

Last Listing Agent Louis Baldwin Threshold Real Estate Services

/21
$200,000 Pending
- 2 Beds
- 2 Baths
- 1,262 Sq Ft
612 Boone Ave, Winchester, KY 40391

Newly remodeled brick ranch with two bedrooms. There are two bathrooms. One is remodeled and oversized with additional storage. The kitchen has new refrigerator, range and dishwasher. The laundry room is conveniently located at the back door off the concrete back porch. The large back yard is private. This would be a great home to downsize or have for a starter home. It could also be used as

Garnett Davis Tom Goebel & Company

612 Boone Ave, Winchester, KY 40391
/2
$195,000 Sold May 15, 2025

Unlisted Address
- 4 Beds
- 2 Baths
- 1,822 Sq Ft
- Built 1980
Last Sold Summary
- $107/SF
Current Estimated Value $204,139

Last Listing Agent Null Non-Member Non-Member Office

Unlisted Address

/78
Est $501,334 Not Listed For Sale

7625 Irvine Rd, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 2,689 Sq Ft
- Built 2006
7625 Irvine Rd, Winchester, KY 40391

Last Sold Summary
- 12% Below List Price
- $212/SF
- 42 Days On Market
Last Sold Price $570,000

Last Listing Agent Elizabeth Torchia Caswell Prewitt Realty, Inc

Showing Results 81 - 120, Page 3 of 18

Kentucky Clark County Winchester

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