Winchester, KY Homes

/34
$220,000
- 3 Beds
- 2 Baths
- 1,680 Sq Ft
37 7th St, Winchester, KY 40391

Check out this charming, well-maintained single-story brick ranch! Featuring 3 bedrooms, 2 full bathrooms, and a spacious living room, this home offers comfort and convenience. Recent updates over the past 10 years include a new HVAC system, roof, windows, water heater, and appliances. The oversized 2-car garage provides ample indoor parking, with additional off-street parking for two more

Andrew Fugitt Coldwell Banker McMahan

37 7th St, Winchester, KY 40391
/25
$375,000 Sold Aug 29, 2025

317 Hanover Dr, Winchester, KY 40391
- 5 Beds
- 3.5 Baths
- 3,111 Sq Ft
- Built 2001
Last Sold Summary
- 1% Below List Price
- $121/SF
- 8 Days On Market
Current Estimated Value $371,679

Last Listing Agent Mike Wheatley Bluegrass Properties Group

317 Hanover Dr, Winchester, KY 40391

/16
Est $190,594 Not Listed For Sale
- 4 Beds
- 2 Baths
- 2,122 Sq Ft
141 Alabama St, Winchester, KY 40391

141 Alabama St, Winchester, KY 40391

/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
/60
$545,000 Sold Oct 31, 2025

445 Lynnway Dr, Winchester, KY 40391
- 4 Beds
- 3.5 Baths
- 3,649 Sq Ft
- Built 1993
Last Sold Summary
- $149/SF
- 4 Days On Market
Last Listing Agent Janna Smith United Real Estate Bluegrass

445 Lynnway Dr, Winchester, KY 40391

/16
Est $407,336 Not Listed For Sale
- 4 Beds
- 2 Baths
- 4,176 Sq Ft
122 French Ave, Winchester, KY 40391

122 French Ave, Winchester, KY 40391

/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
/15
$182,000 Sold Feb 19, 2025

514 Cs-1383, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,120 Sq Ft
- Built 2001
Last Sold Summary
- 1% Above List Price
- $162/SF
- 5 Days On Market
Current Estimated Value $191,028

Last Listing Agent Craig Bridgewater Bridgewater Real Estate

514 Cs-1383, Winchester, KY 40391

/31
Est $205,546 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,946 Sq Ft
134 Central Ave, Winchester, KY 40391

134 Central Ave, Winchester, KY 40391

/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
/54
$360,000 Sold Jan 17, 2025

1455 Irvine Rd, Winchester, KY 40391
- 4 Beds
- 3 Baths
- 2,901 Sq Ft
- Built 1940
Last Sold Summary
- 6% Below List Price
- $124/SF
- 35 Days On Market
Current Estimated Value $417,005

Last Listing Agent Shari Frasure Keller Williams Commonwealth

1455 Irvine Rd, Winchester, KY 40391

/19
Est $221,203 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,322 Sq Ft
130 Central Ave, Winchester, KY 40391

130 Central Ave, Winchester, KY 40391

/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
/27
$380,000 Sold Nov 10, 2025

5705 Mount Sterling Rd, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 2,980 Sq Ft
- Built 1971
Last Sold Summary
- 5% Below List Price
- $128/SF
- 50 Days On Market
Last Listing Agent Dale Hatton Dream Maker Realty, LLC

5705 Mount Sterling Rd, Winchester, KY 40391

/8
Est $244,567 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,359 Sq Ft
109 Alabama St, Winchester, KY 40391

109 Alabama St, Winchester, KY 40391

/32
$359,900 Open Sun 2PM - 4PM
- 3 Beds
- 2.5 Baths
- 1,628 Sq Ft
538 S Maple St, Winchester, KY 40391

24 hour kickout in place. Be the first to call this stunning new construction home! Perfectly situated in the heart of Winchester, this two-story residence offers a fresh, modern feel with convenience at your doorstep. Step inside to discover a bright and airy open-concept main level, featuring durable and stylish Luxury Vinyl Plank (LVP) flooring throughout. The kitchen is a true showstopper,

Heather Kuykendoll Bluegrass Properties Group

538 S Maple St, Winchester, KY 40391
/102
$525,000 Sold Dec 22, 2025

1953 Cabin Creek Rd, Winchester, KY 40391
- 6 Beds
- 4.5 Baths
- 3,846 Sq Ft
- Built 1980
Last Sold Summary
- 4% Below List Price
- $137/SF
- 9 Days On Market
Last Listing Agent Josh Wood Freedom Realty & Property Management

1953 Cabin Creek Rd, Winchester, KY 40391

/23
Est $230,649 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,738 Sq Ft
112 Georgia St, Winchester, KY 40391

112 Georgia St, Winchester, KY 40391

/13
$74,900
- Land
- 2.14 Acres
- $35,000 per Acre
1751 Little Stoner Rd, Winchester, KY 40391

Located at 1751 Little Stoner Rd in Winchester, this 2.139 acre building lot offers the kind of space and setting that's getting harder to find. Open land, rolling country views, and room to create something truly your own, all while staying conveniently connected to the places that matter most. Enjoy the rare balance of peaceful surroundings with easy access. You're just 20 minutes to Lexington,

Kymberly McCreary EXP Realty, LLC

1751 Little Stoner Rd, Winchester, KY 40391
/28
$345,000 Sold Jun 19, 2025

512 Boone Ave, Winchester, KY 40391
- 4 Beds
- 3 Baths
- 3,149 Sq Ft
- Built 1950
Last Sold Summary
- 14% Below List Price
- $110/SF
- 58 Days On Market
Current Estimated Value $371,595

Last Listing Agent Jordan James Lifstyl Real Estate

512 Boone Ave, Winchester, KY 40391

/48
Est $265,805 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,758 Sq Ft
104 Georgia St, Winchester, KY 40391

104 Georgia St, Winchester, KY 40391

/43
$269,900
- 7 Beds
- 3 Baths
- 3,393 Sq Ft
146 W Lexington Ave, Winchester, KY 40391

This investment property has strong rent potential to add to your portfolio. Property is conveniently located in the heart of Downtown Winchester and is zoned R-4. There's a great opportunity to use this property for house hacking -- leverage your money by living in one unit and renting out the other! Downstairs unit has 4 bedrooms and 2 full bathrooms, and its currently leased for $1,495 a

Kevin Bradley KB Realty Group

146 W Lexington Ave, Winchester, KY 40391
/65
$380,000 Sold Jun 19, 2025

399 Stonecrest Rd, Winchester, KY 40391
- 3 Beds
- 4 Baths
- 4,572 Sq Ft
- Built 1976
Last Sold Summary
- 4% Below List Price
- $83/SF
- 3 Days On Market
Current Estimated Value $397,273

Last Listing Agent ROBIN TRIMBLE HomeFirst Real Estate

399 Stonecrest Rd, Winchester, KY 40391

/44
Est $181,270 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,408 Sq Ft
118 Alabama St, Winchester, KY 40391

118 Alabama St, Winchester, KY 40391

/70
$335,000
- 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
/114
$635,000 Sold Sep 30, 2025

315 The Woods Ln, Winchester, KY 40391
- 5 Beds
- 4.5 Baths
- 5,524 Sq Ft
- Built 1995
Last Sold Summary
- 2% Below List Price
- $115/SF
- 63 Days On Market
Last Listing Agent Terri McGraw FC Tucker Bluegrass

315 The Woods Ln, Winchester, KY 40391

/28
Est $270,219 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,626 Sq Ft
116 Alabama St, Winchester, KY 40391

116 Alabama St, Winchester, KY 40391

/5
$29,000
- Land
- 0.46 Acre
- $63,043 per Acre
102 Augusta Dr, Winchester, KY 40391

This is a beautiful area to build your dream home. Backs up to a golf course for a magnificent view. Just minutes from Fort Boonesborough National Park.

Dale Hatton Dream Maker Realty, LLC

102 Augusta Dr, Winchester, KY 40391
/32
$183,000 Sold Jul 30, 2025

517 Hidden Hills Way, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,120 Sq Ft
- Built 2001
Last Sold Summary
- $163/SF
- 78 Days On Market
Current Estimated Value $189,671

Last Listing Agent Brenda Sipes Bridgewater Real Estate

517 Hidden Hills Way, Winchester, KY 40391

/27
Est $268,989 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,968 Sq Ft
335 S Main St, Winchester, KY 40391

335 S Main St, Winchester, KY 40391

/62
$259,500
- 3 Beds
- 2 Baths
- 1,247 Sq Ft
3614 Stamper Dr, Winchester, KY 40391

Fully renovated to perfection, this exceptional home showcases high-end upgrades throughout. Enjoy newly installed windows, doors, and sleek flooring, all complemented by modern appliances and updated cabinetry. A brand-new deck creates the perfect spot for outdoor relaxation, while the freshly built storage building out back adds extra convenience. The attached garage offers attic access with

Darrell Tackett Dream Maker Realty, LLC

3614 Stamper Dr, Winchester, KY 40391
/17
$175,000 Sold May 07, 2025

220 Jackson St, Winchester, KY 40391
- 2 Beds
- 1 Bath
- 1,228 Sq Ft
- Built 1940
Last Sold Summary
- $143/SF
- 1 Day On Market
Current Estimated Value $172,901

Last Listing Agent Joanna Howell Bluegrass Properties Group

220 Jackson St, Winchester, KY 40391

/20
Est $204,868 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,344 Sq Ft
38 Hughes Ave, Winchester, KY 40391

38 Hughes Ave, Winchester, KY 40391

/3
$345,000 New Construction
- 3 Beds
- 2 Baths
- 1,677 Sq Ft
225 Evergreen Dr, Winchester, KY 40391

Welcome to The Run for the Roses - a thoughtfully designed proposed construction home located in the desirable Locust Hill Acres community. This charming home offers an open concept floor plan perfect for modern living, featuring 3 spacious bedrooms and 2 full bathrooms.The large primary suite is a true retreat, complete with a generously sized walk-in closet and a well-appointed ensuite

Rex Hall United Real Estate Bluegrass

225 Evergreen Dr, Winchester, KY 40391
/35
$189,900 Sold Jan 16, 2025

24 Hughes Ave, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,200 Sq Ft
- Built 2024
Last Sold Summary
- $158/SF
- 24 Days On Market
Current Estimated Value $216,329

Last Listing Agent Nena Honaker Tom Goebel & Company

24 Hughes Ave, Winchester, KY 40391

/12
Est $120,628 Not Listed For Sale
- 2 Beds
- 1 Bath
- 679 Sq Ft
46 Hughes Ave, Winchester, KY 40391

46 Hughes Ave, Winchester, KY 40391

/27
$72,500
- 3 Beds
- 2 Baths
- 1,128 Sq Ft
725 Berry Ct, Winchester, KY 40391

Looking for affordable homeownership in Winchester, KY? This move-in ready 3-bedroom, 2-bath manufactured home offers modern living at an incredible value. Built just 3 years ago and meticulously maintained, this home feels like new from the moment you step inside. Located in the heart of Winchester, you'll enjoy easy access to local restaurants, shopping, grocery stores, parks, and everyday

Christa Joynt Keller Williams Commonwealth

725 Berry Ct, Winchester, KY 40391
/61
$220,000 Sold Nov 10, 2025

313 Snowden Dr, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,232 Sq Ft
- Built 1960
Last Sold Summary
- 12% Below List Price
- $179/SF
- 51 Days On Market
Last Listing Agent Josh Wood Freedom Realty & Property Management

313 Snowden Dr, Winchester, KY 40391

/35
Est $325,749 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,769 Sq Ft
8 French Ave, Winchester, KY 40391

8 French Ave, Winchester, KY 40391

/6
$200,000
- Land
- 0.81 Acre
- $246,914 per Acre
550 Bullion Blvd, Winchester, KY 40391

Rarely available Bypass frontage lot for sale! Exciting opportunity to locate alongside a new Chipotle that is soon to be under construction. Retention in place, leaving approximately 1/2-acre developable. Perfect location for a national retailer. Ideally located along the heart of Bypass Road in Winchester, Kentucky between Kroger and Walmart shopping centers. Winchester, Kentucky is the county

Greg Leveridge Block + Lot Real Estate

550 Bullion Blvd, Winchester, KY 40391

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Kentucky Clark County Winchester

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