Winchester, KY Homes

/32
Est $279,736 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,893 Sq Ft
13 Euclid Ave, Winchester, KY 40391

13 Euclid Ave, Winchester, KY 40391

/2
$78,500
- Land
- 0.22 Acre
- $356,818 per Acre
Lot 4 Plantations Dr, Winchester, KY 40391

NOW SELLING SFH Buildable Lots of 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

Melia Hord Keller Williams Legacy Group

Lot 4 Plantations Dr, Winchester, KY 40391
/49
$390,000 Sold Jun 30, 2025

1094 Ford Hampton Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,900 Sq Ft
- Built 1940
Last Sold Summary
- 2% Below List Price
- $205/SF
- 26 Days On Market
Current Estimated Value $390,411

Last Listing Agent Tom D. Thomas The Real Estate Co.

1094 Ford Hampton Rd, Winchester, KY 40391

/43
Est $356,877 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,513 Sq Ft
201 Boone Ave, Winchester, KY 40391

201 Boone Ave, Winchester, KY 40391

/26
$248,900
- 5 Beds
- 3 Baths
- 3,007 Sq Ft
221 S Highland St, Winchester, KY 40391

INVESTOR SPECIAL, You have the opportunity to purchase a fully occupied tri-plex in the heart of Winchester with instant cash flow. Main level unit is a large 2 bed, one bath. Upstairs unit is also a 2 bed, one bath, and lower level is a 1 bed, one bath unit. There is street parking and alley access with parking in the rear. All units have their own exterior entrance. Some utilities are metered

Joshua Lynch The Brokerage

221 S Highland St, Winchester, KY 40391
/61
$545,000 Sold Jul 15, 2025

1063 Wades Mill Rd, Winchester, KY 40391
- 4 Beds
- 3.5 Baths
- 3,958 Sq Ft
- Built 2000
Last Sold Summary
- 11% Below List Price
- $138/SF
- 180 Days On Market
Current Estimated Value $556,382

Last Listing Agent Joseph (Alex) Smallwood Christies International Real Estate Bluegrass

1063 Wades Mill Rd, Winchester, KY 40391

/45
Est $430,478 Not Listed For Sale
- 4 Beds
- 3 Baths
- 3,012 Sq Ft
142 College St, Winchester, KY 40391

142 College St, Winchester, KY 40391

/17
$229,000 Pending
- 4 Beds
- 2 Baths
- 1,858 Sq Ft
394 S Main St, Winchester, KY 40391

Welcome home to this beautifully remodeled home, originally built in 1900 but completely renewed for today's lifestyle. This spacious 4 bedroom, 2 bath home features new tile and carpeting with some of the original hardwood maintained in the living room area and downstairs bedroom. The kitchen has new cabinets, countertops, range, dishwasher and refrigerator. There is a new water heater for your

Tracey Goebel Tom Goebel & Company

394 S Main St, Winchester, KY 40391
/65
$290,000 Sold Jun 18, 2025

13 Robyn Dr, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,844 Sq Ft
- Built 1980
Last Sold Summary
- 2% Below List Price
- $157/SF
- 1 Day On Market
Current Estimated Value $293,270

Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

13 Robyn Dr, Winchester, KY 40391

/32
Est $254,729 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 1,255 Sq Ft
8 Nunnelly Ct, Winchester, KY 40391

8 Nunnelly Ct, Winchester, KY 40391

/79
$435,000 Pending
- 3 Beds
- 2 Baths
- 1,064 Sq Ft
1410 Dry Fork Creek Rd, Winchester, KY 40391

This breathtaking 92.3 +/- acre turnkey property is a nature lover's dream, offering endless opportunities for recreation, relaxation, and country living at its finest. Enjoy gently rolling terrain with a perfect blend of pasture, woods, and scenic trails, along with approximately one mile of road and creek frontage in a peaceful, private setting. Roughly 25 acres of hay field provide excellent

Skyler Lewis Dream Maker Realty, LLC

1410 Dry Fork Creek Rd, Winchester, KY 40391
/32
$360,000 Sold Aug 14, 2025

418 Skylark Dr, Winchester, KY 40391
- 5 Beds
- 2.5 Baths
- 2,746 Sq Ft
- Built 1990
Last Sold Summary
- 3% Above List Price
- $131/SF
- 12 Days On Market
Current Estimated Value $354,250

Last Listing Agent Kymberly McCreary EXP Realty, LLC

418 Skylark Dr, Winchester, KY 40391

/47
Est $342,226 Not Listed For Sale
- 4 Beds
- 2 Baths
- 3,299 Sq Ft
113 S Burns Ave, Winchester, KY 40391

113 S Burns Ave, Winchester, KY 40391

/37
$224,000
- 3 Beds
- 1 Bath
- 1,188 Sq Ft
314 E Broadway St, Winchester, KY 40391

Welcome to this beautifully maintained 3-bedroom, 1-bath ranch offering 1,188 sqft of classic charm on a spacious 0.26-acre lot! This home blends timeless character with thoughtful updates, featuring an inviting single-level layout, bright living areas, well-sized bedrooms, and an updated kitchen with an added pantry for extra storage. Out back, enjoy an attached and enclosed sunroom perfect for

Ashley Spencer Keller Williams Commonwealth

314 E Broadway St, Winchester, KY 40391
/79
$204,000 Sold Oct 30, 2025

133 S Burns Ave, Winchester, KY 40391
- 4 Beds
- 2 Baths
- 3,295 Sq Ft
- Built 1915
Last Sold Summary
- 18% Below List Price
- $62/SF
- 20 Days On Market
Last Listing Agent Josh Wood Freedom Realty & Property Management

133 S Burns Ave, Winchester, KY 40391

/35
Est $357,398 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,498 Sq Ft
123 W Hickman St, Winchester, KY 40391

123 W Hickman St, Winchester, KY 40391

/10
$775,000
- Land
- 3 Acres
- $258,333 per Acre
609 Bullion Blvd Unit 3A, Winchester, KY 40391

Ideally located along the heart of Bypass Road (ADT: 24,801) in Winchester, Kentucky between and surrounding Kroger and Walmart shopping centers. These lots are offered as 1+ acres and may be subdivided. Winchester, KY is the county seat of Clark County, KY and is part of the Lexington-Fayette KY Metropolitan Statistical Area, and is supported by such industries such as Amazon, Ale-8-One, and

Greg Leveridge Block + Lot Real Estate

609 Bullion Blvd Unit 3A, Winchester, KY 40391
/28
$246,000 Sold Nov 06, 2025

204 Moss Ct, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,430 Sq Ft
- Built 1998
Last Sold Summary
- 3% Above List Price
- $172/SF
- 1 Day On Market
Last Listing Agent Brooke Martin RO&CO Real Estate

204 Moss Ct, Winchester, KY 40391

/49
Est $287,697 Not Listed For Sale
- 3 Beds
- 1 Bath
- 2,018 Sq Ft
115 Olde Potomac Ave, Winchester, KY 40391

115 Olde Potomac Ave, Winchester, KY 40391

/2
$2,000,000
- Land
- 17.87 Acres
- $111,919 per Acre
1509 Boonesboro Rd, Winchester, KY 40391

17.87 Acre farm available for sale. Ideal location for redevelopment. Gently rolling topography. Corner lot with excellent visibility. Water, electric, sewer, gas and telecommunications available. Conveniently located near RD Campbell Junior High School, George Rogers Clark High School & Winchester Country Club. Located 3 miles south of Interstate 64. Signalized corner lot at Boonesboro Rd. &

Cheryl Johnston CMI Properties

1509 Boonesboro Rd, Winchester, KY 40391
/58
$232,500 Sold Jul 12, 2025

114 Holiday Rd, Winchester, KY 40391
- 3 Beds
- 1.5 Baths
- 1,161 Sq Ft
- Built 1980
Last Sold Summary
- 7% Below List Price
- $200/SF
- 235 Days On Market
Current Estimated Value $238,360

Last Listing Agent Karen Smith Emmerich Muzic Realty

114 Holiday Rd, Winchester, KY 40391

/35
Est $302,480 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,588 Sq Ft
231 W Hickman St, Winchester, KY 40391

231 W Hickman St, Winchester, KY 40391

/20
$139,900
- 3 Beds
- 1 Bath
- 1,150 Sq Ft
103 Yorktowne Ct, Winchester, KY 40391

Affordable and move-in ready! This home will qualify for FHA, VA &/or Rural Housing Loan. This charming 3 bedroom, 1 bath home offers the perfect opportunity for first-time buyers, down-sizers, or investors. With a welcoming layout, comfortable living spaces, and a great location in Winchester, this property is an excellent value in today's market. Enjoy the convenience of nearby shopping,

Susy Esquivel Allied Realty

103 Yorktowne Ct, Winchester, KY 40391
/28
$234,500 Sold Jul 29, 2025

108 Sturbridge Ln, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,200 Sq Ft
- Built 2004
Last Sold Summary
- 4% Below List Price
- $195/SF
- 45 Days On Market
Current Estimated Value $241,211

Last Listing Agent Jason Szaks EXIT TOWN & COUNTRY REALTORS

108 Sturbridge Ln, Winchester, KY 40391

/36
Est $234,410 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,755 Sq Ft
242 W Lexington Ave, Winchester, KY 40391

242 W Lexington Ave, Winchester, KY 40391

/31
$295,000
- 3 Beds
- 3 Baths
- 1,738 Sq Ft
420 Willowbrook Rd, Winchester, KY 40391

Tucked near the cul-de-sac on a dead-end street in the Windridge neighborhood, this 3 bedroom, 3 bath ranch offers easy access to the Bypass and Boone Ave along with a functional, spacious layout. A foyer entry opens to a formal living room featuring a wood-burning fireplace, built-in shelving, and a charming cased opening that provides sightlines into the kitchen and dining area, while a den

Michelle Blackburn RE/MAX Creative, Winchester

420 Willowbrook Rd, Winchester, KY 40391
/22
$334,327 Sold Jul 01, 2025

136 Gibson Way, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 1,997 Sq Ft
- Built 2024
Last Sold Summary
- $167/SF
- 219 Days On Market
Current Estimated Value $339,086

Last Listing Agent Neshia Gaines Christies International Real Estate Bluegrass

136 Gibson Way, Winchester, KY 40391

/41
Est $294,170 Not Listed For Sale
- 6 Beds
- 3.5 Baths
- 3,072 Sq Ft
21 Beckner St, Winchester, KY 40391

21 Beckner St, Winchester, KY 40391

/42
$259,900 Pending
- 3 Beds
- 2 Baths
- 1,333 Sq Ft
125 Summerhill Way, Winchester, KY 40391

Welcome home to this darling farmhouse-style gem on a quiet street in Winchester! You'll love the inviting covered front porch, spacious great room with vaulted ceiling, and convenient first-floor primary suite. The kitchen features stainless steel appliances, and the current owners have added fresh flooring and paint so it's truly move-in ready. Step out back to enjoy the screened porch and the

Gwen Mathews Bluegrass Sotheby's International Realty

125 Summerhill Way, Winchester, KY 40391
/6
$50,000 Sold Mar 17, 2025

221 Ashton Oak Way, Winchester, KY 40391
- Land
- 0.39 Acre
- $128,205 per Acre
Last Sold Summary
- 9% Below List Price
- 264 Days On Market
Current Estimated Value $62,110

Last Listing Agent Melia Hord Keller Williams Legacy Group

221 Ashton Oak Way, Winchester, KY 40391

/52
Est $315,930 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,092 Sq Ft
328 S Burns Ave, Winchester, KY 40391

328 S Burns Ave, Winchester, KY 40391

/13
$140,000
- 2 Beds
- 1 Bath
- 1,254 Sq Ft
208 4th St, Winchester, KY 40391

Discover the potential of this spacious 0.27-acre residential home nestled in a neighborhood community on clear and level land located in a Cul-de-sac of Lincoln Park Subdivision. This Property features 2-bedrooms, 1-Bathroom, a large family room with a fireplace. There is also a large versatile barn on the property as well. This could be an investment opportunity as well, for ideal savvy

Anita McDermott Keller Williams Bluegrass Realty

208 4th St, Winchester, KY 40391
/37
$275,000 Sold Sep 10, 2025

279 Ascot Ave, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 2,247 Sq Ft
- Built 2000
Last Sold Summary
- 8% Below List Price
- $122/SF
- 2 Days On Market
Current Estimated Value $290,485

Last Listing Agent Chase Pennington Team Pannell Real Estate

279 Ascot Ave, Winchester, KY 40391

/32
Est $312,593 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,794 Sq Ft
322 S Burns Ave, Winchester, KY 40391

322 S Burns Ave, Winchester, KY 40391

/10
$374,900 Pending
- Land
- 1.29 Acres
- $290,620 per Acre
395 Croxton Way, Winchester, KY 40391

1.29 acre Commercial Lot zoned B-3 that's slightly elevated with maximum visibility for your business. Ideal location for a gas station, fast food restaurant or retail shop. Lot near Clark Medical Center Hospital. To the south is Lexington Road (US 60), to the west is Floyd Clay Drive, and to the North is Croxton Way. Making three (3) different entrances to enhance accessibility to any business.

Rich Decker Rector Hayden Realtors

395 Croxton Way, Winchester, KY 40391
/24
$198,000 Sold Jul 18, 2025

113 Colonial Park Dr, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,075 Sq Ft
- Built 1983
Last Sold Summary
- 2% Above List Price
- $184/SF
- 0 Days On Market
Current Estimated Value $204,526

Last Listing Agent Janet Baldwin Kentucky Land and Home

113 Colonial Park Dr, Winchester, KY 40391

/51
Est $408,819 Not Listed For Sale
- 4 Beds
- 2 Baths
- 3,227 Sq Ft
200 College St, Winchester, KY 40391

200 College St, Winchester, KY 40391

/28
$799,900
- Land
- 13.19 Acres
- $60,644 per Acre
1600 Ironworks Rd, Winchester, KY 40391

This property has it all! Easy access to Veterans Memorial Bypass, I-64, and downtown Winchester, plus entrances on Ironworks and clear visibility from the Bypass. This does have sewer and water located on the property. Full of potential possibilities zoned Planned Development and more acreage is available if needed. The property access is a driveway off Ironworks Road across from Center Drive

Josh Wood Freedom Realty & Property Management

1600 Ironworks Rd, Winchester, KY 40391
/2
$415,000 Sold Mar 03, 2025

1480 White Turley Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 2,470 Sq Ft
Last Sold Summary
- $168/SF
- 0 Days On Market
Last Listing Agent Hannah Porter DEE'S REAL ESTATE SERVICE

1480 White Turley Rd, Winchester, KY 40391

/12
Est $257,158 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,650 Sq Ft
217 College St, Winchester, KY 40391

217 College St, Winchester, KY 40391

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Kentucky Clark County Winchester

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