Winchester, KY Homes

/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
/79
$584,900 Sold Feb 17, 2026

180 Casa Landa Way, Winchester, KY 40391
- 4 Beds
- 3.5 Baths
- 4,779 Sq Ft
- Built 2000
Last Sold Summary
- 10% Below List Price
- $122/SF
- 46 Days On Market
Current Estimated Value $598,625

Last Listing Agent Janna Smith United Real Estate Bluegrass

180 Casa Landa Way, Winchester, KY 40391

/27
Est $242,945 Not Listed For Sale

335 S Main St, Winchester, KY 40391
- 4 Beds
- 2 Baths
- 1,968 Sq Ft
- Built 1920
335 S Main St, Winchester, KY 40391

Last Sold Summary
- 3% Below List Price
- $127/SF
- 41 Days On Market
Last Sold Price $249,500

Last Listing Agent Shari Frasure Keller Williams Commonwealth

/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
/21
$338,000 Sold Mar 19, 2025

240 Athens Boonesboro Rd, Winchester, KY 40391
- 3 Beds
- 1.5 Baths
- 1,841 Sq Ft
- Built 1983
Last Sold Summary
- 170% Above List Price
- $184/SF
- 26 Days On Market
Current Estimated Value $272,722

Last Listing Agent Damon Ballinger C Roger Lewis Agency

240 Athens Boonesboro Rd, Winchester, KY 40391

/35
Est $210,407 Not Listed For Sale

24 Hughes Ave, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,200 Sq Ft
- Built 2024
24 Hughes Ave, Winchester, KY 40391

Last Sold Summary
- 11% Above List Price
- $158/SF
- 24 Days On Market
Last Sold Price $189,900

Last Listing Agent Nena Honaker Tom Goebel & Company

/2
$110,000
- Land
- 0.32 Acre
- $343,750 per Acre
135 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

135 Jacob Ct, Winchester, KY 40391
/15
$110,000 Sold Sep 04, 2025

706 Williamsburg Dr, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 924 Sq Ft
- Built 2024
Last Sold Summary
- 21% Below List Price
- $119/SF
Current Estimated Value $117,834

Last Listing Agent Andrew Fugitt Coldwell Banker McMahan

706 Williamsburg Dr, Winchester, KY 40391

/20
Est $191,329 Not Listed For Sale

38 Hughes Ave, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,344 Sq Ft
- Built 1940
38 Hughes Ave, Winchester, KY 40391

Last Sold Summary
- 16% Above List Price
- $123/SF
- 8 Days On Market
Last Sold Price $165,000

Last Listing Agent Destiny Darby Keller Williams Commonwealth

/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
/30
$185,000 Sold Feb 06, 2026

40 Garner St, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,354 Sq Ft
- Built 1950
Last Sold Summary
- 16% Below List Price
- $137/SF
- 217 Days On Market
Current Estimated Value $204,801

Last Listing Agent Nicole Seals Guide Realty, Inc.

40 Garner St, Winchester, KY 40391

/35
Est $306,465 Not Listed For Sale

8 French Ave, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 2,769 Sq Ft
- Built 1950
8 French Ave, Winchester, KY 40391

Last Sold Summary
- 43% Above List Price
- $78/SF
- 10 Days On Market
Last Sold Price $215,000

Last Listing Agent K Lyndi Huddleston Lifstyl Real Estate

/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
/19
$189,500 Pending
- 2 Beds
- 2.5 Baths
- 1,197 Sq Ft
111 Quail Ridge Rd, Winchester, KY 40391

Move-In Ready Brick Townhome with Garage and Fireplace Step into this charming brick townhome offering comfort, style, and convenience in every detail. The spacious living room features a cozy fireplace, soft neutral tones, and natural light that make it easy to feel at home. The open layout flows to the kitchen and dining area, creating the perfect setting for everyday living or entertaining

Kim Dice EXP Realty, LLC

111 Quail Ridge Rd, Winchester, KY 40391

/41
Est $277,122 Not Listed For Sale

254 S Highland St, Winchester, KY 40391
- 4 Beds
- 2 Baths
- 3,395 Sq Ft
- Built 1935
254 S Highland St, Winchester, KY 40391

Last Sold Summary
- 39% Above List Price
- $59/SF
- 10 Days On Market
Last Sold Price $200,000

Last Listing Agent Michelle Blackburn RE/MAX

/2
$110,000
- Land
- 0.32 Acre
- $343,750 per Acre
115 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

115 Jacob Ct, Winchester, KY 40391
/2
$160,000 Sold Sep 19, 2025

8 Village Dr, Winchester, KY 40391
- 3 Beds
- 1.5 Baths
- 1,414 Sq Ft
- Built 1970
Last Sold Summary
- 9% Below List Price
- $113/SF
- 0 Days On Market
Current Estimated Value $274,035

Last Listing Agent Joyce Ratliff Tom Goebel & Company

8 Village Dr, Winchester, KY 40391

/24
Est $177,127 Not Listed For Sale

54 Winn Ave, Winchester, KY 40391
- 5 Beds
- 2 Baths
- 1,530 Sq Ft
- Built 1940
54 Winn Ave, Winchester, KY 40391

Last Sold Summary
- 2% Below List Price
- $118/SF
- 90 Days On Market
Last Sold Price $180,000

Last Listing Agent Lukas Owens 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
/22
$193,000 Sold Jun 06, 2025

116 Linden Ave, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,164 Sq Ft
- Built 1945
Last Sold Summary
- 2% Below List Price
- $166/SF
- 3 Days On Market
Current Estimated Value $200,121

Last Listing Agent Jeremy Perryman United Real Estate Bluegrass

116 Linden Ave, Winchester, KY 40391

/33
Est $273,356 Not Listed For Sale

144 E Broadway St, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 2,544 Sq Ft
- Built 1930
144 E Broadway St, Winchester, KY 40391

Last Sold Summary
- 33% Above List Price
- $81/SF
- 119 Days On Market
Last Sold Price $205,000

Last Listing Agent Thomas Harper Tom Harper and Associates

/27
$160,000
- 2 Beds
- 1 Bath
- 1,088 Sq Ft
233 E Washington St, Winchester, KY 40391

Welcome to 233 E. Washington Street, a charming ranch-style home offering comfort, space, and convenience in the heart of Winchester. The Roof, Windows and HVAC are updated. This 2-bedroom, 1-bath residence features an open-concept layout designed for easy living and everyday functionality. LVP flooring runs throughout the home, providing a clean, modern look that's both durable and low

Lukas Owens The Brokerage

233 E Washington St, Winchester, KY 40391
/19
$220,000 Sold Apr 23, 2025

112 Central Ave, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,200 Sq Ft
- Built 2025
Last Sold Summary
- 1% Above List Price
- $183/SF
- 1 Day On Market
Current Estimated Value $224,113

Last Listing Agent Nena Honaker Tom Goebel & Company

112 Central Ave, Winchester, KY 40391

/10
Est $246,292 Not Listed For Sale

130 E Broadway St, Winchester, KY 40391
- 5 Beds
- 3 Baths
- 2,445 Sq Ft
- Built 1940
130 E Broadway St, Winchester, KY 40391

Last Sold Summary
- 15% Above List Price
- $88/SF
- 38 Days On Market
Last Sold Price $215,000

Last Listing Agent Chase Pennington Team Pannell Real Estate

/22
$145,000 Pending
- 3 Beds
- 2 Baths
- 1,300 Sq Ft
417 Mount Vernon Dr, Winchester, KY 40391

A 3 bedroom 2 bath home with a 2 car garage under 150k? Unbelievable! Start off your new year with a new home! Spacious manufactured home in Yorktowne Estates where YOU own your lot! Large primary bedroom, nice living room, huge family room, plenty of dining space, gas range, updated cabinets and sink. Check out that garage!! Private driveway with plenty of parking space, covered porches, metal

Jason Townsend Kentucky Residential Real Estate, LLC

417 Mount Vernon Dr, Winchester, KY 40391
/2
$85,000 Sold Dec 12, 2025

1385 Sewell Shop Rd, Winchester, KY 40391
- Land
- 6.43 Acres
- $13,219 per Acre
Last Sold Summary
- 6% Below List Price
- 6 Days On Market
Last Listing Agent Zella Rosenthal Tom Goebel & Company

1385 Sewell Shop Rd, Winchester, KY 40391

/17
Est $308,096 Not Listed For Sale

129 S Highland St, Winchester, KY 40391
- 6 Beds
- 4 Baths
- 3,608 Sq Ft
- Built 1940
129 S Highland St, Winchester, KY 40391

Last Sold Summary
- 15% Above List Price
- $75/SF
- 86 Days On Market
Last Sold Price $269,000

Last Listing Agent Joshua Lynch The Brokerage

/2
$110,000
- Land
- 0.5 Acre
- $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
/53
$867,500 Sold Aug 01, 2025

511 Boone Ave, Winchester, KY 40391
- 4 Beds
- 4.5 Baths
- 4,698 Sq Ft
- Built 1885
Last Sold Summary
- 11% Below List Price
- $185/SF
- 318 Days On Market
Current Estimated Value $911,417

Last Listing Agent Greg Leveridge Block + Lot Real Estate

511 Boone Ave, Winchester, KY 40391

/17
Est $141,387 Not Listed For Sale

21 Franklin Ave, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,006 Sq Ft
- Built 1940
21 Franklin Ave, Winchester, KY 40391

Last Sold Summary
- 9% Above List Price
- $129/SF
- 1 Day On Market
Last Sold Price $130,000

Last Listing Agent Austin Polley The Polley Group

/55
$419,900
- 5 Beds
- 3.5 Baths
- 2,564 Sq Ft
6504 Combs Ferry Rd, Winchester, KY 40391

PRICE IMPROVEMENT PLUS SELLERS ARE OFFERING UP TO $7,500 TOWARD BUYERS CLOSING COSTS, PREPAIDS OR RATE BUYDOWN. Welcome to an extraordinary residence where luxury, craftsmanship, and natural beauty come together. This house has been taken down to the studs, and thoughtfully rebuilt. This two story home with a walk-out basement sits on 8 acres, adjoining the Lower Howard Creek Preserve, offering

Lucy Martin Jenkins United Real Estate Bluegrass

6504 Combs Ferry Rd, Winchester, KY 40391
/36
$420,000 Sold Feb 25, 2026

134 Fontaine Blvd, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 2,747 Sq Ft
- Built 1994
Last Sold Summary
- 7% Below List Price
- $153/SF
- 126 Days On Market
Current Estimated Value $421,734

Last Listing Agent Craig Bridgewater Bridgewater Real Estate

134 Fontaine Blvd, Winchester, KY 40391

/23
Est $190,606 Not Listed For Sale

353 E Broadway St, Winchester, KY 40391
- 4 Beds
- 2 Baths
- 1,905 Sq Ft
- Built 1940
353 E Broadway St, Winchester, KY 40391

Last Sold Summary
- 189% Above List Price
- $35/SF
- 1 Day On Market
Last Sold Price $66,000

Last Listing Agent Keith Wilson Coldwell Banker McMahan

/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
/41
$310,000 Sold Dec 29, 2025

1996 White Conkwright Rd, Winchester, KY 40391
- 2 Beds
- 1 Bath
- 1,055 Sq Ft
- Built 1966
Last Sold Summary
- 9% Below List Price
- $294/SF
- 45 Days On Market
Current Estimated Value $336,000

Last Listing Agent Lucy Martin Jenkins United Real Estate Bluegrass

1996 White Conkwright Rd, Winchester, KY 40391

/32
Est $200,467 Not Listed For Sale

230 Winn Ave, Winchester, KY 40391
- 4 Beds
- 1.5 Baths
- 1,400 Sq Ft
- Built 1940
230 Winn Ave, Winchester, KY 40391

Last Sold Summary
- 12% Above List Price
- $128/SF
- 73 Days On Market
Last Sold Price $179,500

Last Listing Agent Cindy Walker Sandy Stuart Realty

/37
$949,950 Pending
- 3 Beds
- 2.5 Baths
- 2,400 Sq Ft
700 Nick Ln, Winchester, KY 40391

🚨 BIG PRICE DROP ALERT! 🚨 Motivated sellers are ready to make a deal—this is your chance to snag an unbeatable offer! 💰🏡Step into country living with this amazing 120-acre working farm! You'll love the brand-new 3-bedroom, 2.5-bath home that features an open floor plan, perfect for hanging out with family or hosting friends. It's got all the modern touches, so you

Darrell Tackett Dream Maker Realty, LLC

700 Nick Ln, Winchester, KY 40391
/38
$599,500 Sold Sep 08, 2025

102 Bella Shae Way, Winchester, KY 40391
- 4 Beds
- 2 Baths
- 2,204 Sq Ft
- Built 2025
Last Sold Summary
- $272/SF
- 72 Days On Market
Current Estimated Value $591,256

Last Listing Agent Shane Underwood Keller Williams Commonwealth

102 Bella Shae Way, Winchester, KY 40391

/17
Est $170,326 Not Listed For Sale

30 Rowland Ave, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 956 Sq Ft
- Built 1952
30 Rowland Ave, Winchester, KY 40391

Last Sold Summary
- 34% Above List Price
- $133/SF
- 0 Days On Market
Last Sold Price $127,000

Last Listing Agent Lyndsey Ryles Kentucky Elite Real Estate

/27
$175,000
- 3 Beds
- 2 Baths
- 1,305 Sq Ft
6 Monroe Ave, Winchester, KY 40391

Charming Home in the Heart of Winchester! Welcome to 6 Monroe Ave - a 3-bedroom, 2-bath home full of character and modern touches. Step inside to find an inviting family room with an updated shiplap fireplace surround, perfect for cozy evenings. The kitchen is filled with natural light and features granite countertops, making it both stylish and functional. Recent updates include an HVAC system

Lindsey Bivens Berkshire Hathaway de Movellan Properties

6 Monroe Ave, Winchester, KY 40391

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Kentucky Clark County Winchester

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