Vintage homes for sale & real estate in Winchester, KY

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ABOUT THIS HOME
Vintage Home for sale in Winchester, KY:
Own a beautifully maintained piece of Winchester, KY history on desirable South Burns Avenue. This charming home features an inviting wrap-around porch perfect for year-round enjoyment and outstanding curb appeal. Step into a warm and welcoming entryway where refinished hardwood floors flow throughout the main level. Original pocket doors open into the library, showcasing the home's timeless character. A secondary entry into the spacious living room adds everyday convenience, and the unique angled dining room with built-in cabinetry provides both charm and functionality. The kitchen features classic harlequin pattern flooring and sits just steps from a combined pantry/laundry room—id

$318,500

4 beds1.5 baths2,170 sq ft

214 S Burns Ave, Winchester, KY 40391

8,276 sq ft lot • Community pool • Built 1940

ABOUT THIS HOME
Vintage Home for sale in Winchester, KY:
Welcome to this charming 3-bedroom, 1.5-bath home situated on a lovely corner lot. Step inside to discover a well-maintained interior with a thoughtful layout that flows effortlessly from room to room. The cozy living area opens to the dining space. You'll also find two versatile flex spaces, each filled with natural light from large windows-perfect for a home office, playroom, or creative studio. The kitchen and adjoining butler's pantry showcase the home's timeless craftsmanship, featuring original built-in cabinetry that blends charm with functionality. A convenient first-floor laundry and mudroom add to the home's practicality. Outside, enjoy a private, fully fenced yard, perfect for pe

$255,000

3 beds1.5 baths2,188 sq ft

357 Crescent Ave, Winchester, KY 40391

Butler's pantry • Flex spaces • Corner lot

ABOUT THIS HOME
Vintage Home for sale in Winchester, KY:
Get a piece of Bluegrass heaven in this move-in ready modern farmhouse on just under 5acres in Clark County. Dreaming of the country life? This is it, originally built in 1865 this timeless home has been completely updated and seamlessly blended the history with modern elegant design and livability. Classic farmhouse style with tons of natural light that bring the outside in. Spacious great room and even larger eat in kitchen with access to the large covered back porch. Chef's kitchen with quartz countertops and butler's pantry with open shelving. First floor primary suite that is a true sanctuary with room for lounging. Spa-like bathroom with freestanding tub and a walk-in closet dreams ar

$420,000

5 beds2.5 baths2,924 sq ft

1857 Ironworks Rd, Winchester, KY 40391

Freestanding tub • Walk-in closet • Modern farmhouse

ABOUT THIS HOME
Vintage Home for sale in Winchester, KY:
FLIP This House!!! Seller Has Added A Large Primary Addition And Front Porch. This 4 Bedroom 2 1/1 Bath Home Is Ready For Your Finishes And Has A Fantastic Floor Plan With Large Loft (Whole Home At Stud Level). Great Opportunity To Make Money Or Live In This Beautiful Home!

$130,000

4 beds2.5 baths2,131 sq ft

205 E Washington St, Winchester, KY 40391

Large loft • Front porch • 5,662 sq ft lot

ABOUT THIS HOME
Vintage Home for sale in Winchester, KY:
Do you ever wonder what it would be like to live in the days of "Gone with the Wind"? Well, here is your chance to own your own personal "Tara". Spacious country home with acreage suitable for children, pets, and livestock. This home is perfect for escaping city life and crowds. Home consists of 5 bedrooms, 3 full bathrooms, Living Room, Dining Room, large Kitchen, room for an office or craft room. Home is complimented by a beautiful front staircase as well as a back staircase for added convenience. Home has covered porches on both the front and rear of home to enjoy the beautiful sunrises and sunsets or just sit back and take in the country views from your own 5 acres.

$475,000

5 beds3 baths3,718 sq ft

1503 Schollsville Rd, Winchester, KY 40391

Covered porches • Country views • 5 acre lot

Property at 121 Fitch Ave, Winchester, KY 40391, 4 beds, 3 baths

$349,000

4 beds3 baths2,100 sq ft

121 Fitch Ave, Winchester, KY 40391

Property at 6239 Old Boonesboro Rd, Winchester, KY 40391, 4 beds, 2 baths

$399,000

4 beds2 baths2,659 sq ft

6239 Old Boonesboro Rd, Winchester, KY 40391

Property at 114 Magnolia St, Winchester, KY 40391, 2 beds, 1 bath

$115,000

2 beds1 bath910 sq ft

114 Magnolia St, Winchester, KY 40391

Property at 12 Linden Ave, Winchester, KY 40391, 3 beds, 2 baths

$240,000

3 beds2 baths— sq ft

12 Linden Ave, Winchester, KY 40391

Property at 101 S Burns Ave Unit 1,2,3,4, Winchester, KY 40391, 8 beds, 4 baths

$675,000

8 beds4 baths5,046 sq ft

101 S Burns Ave Unit 1,2,3,4, Winchester, KY 40391

Property at 245 Ecton Rd, Winchester, KY 40391, 3 beds, 1 bath

$209,900

3 beds1 bath1,074 sq ft

245 Ecton Rd, Winchester, KY 40391

Property at 174 Hidden Grove Ln, Winchester, KY 40391, 2 beds, 2 baths

$265,000

2 beds2 baths1,521 sq ft

174 Hidden Grove Ln, Winchester, KY 40391

Property at 3166 Colby Rd, Winchester, KY 40391, 3 beds, 2.5 baths

$1,889,000

3 beds2.5 baths4,518 sq ft

3166 Colby Rd, Winchester, KY 40391

Property at 221 S Highland St, Winchester, KY 40391, 5 beds, 3 baths

$257,500

5 beds3 baths3,007 sq ft

221 S Highland St, Winchester, KY 40391

Property at 146 Cook Ave, Winchester, KY 40391, 3 beds, 1 bath

$167,500

3 beds1 bath1,274 sq ft

146 Cook Ave, Winchester, KY 40391

Property at 27 Ashland Ave, Winchester, KY 40391, 3 beds, 2 baths

$189,900

3 beds2 baths1,653 sq ft

27 Ashland Ave, Winchester, KY 40391

Property at 6 Monroe Ave, Winchester, KY 40391, 3 beds, 2 baths

$182,000

3 beds2 baths1,305 sq ft

6 Monroe Ave, Winchester, KY 40391

Property at 218 E Washington St, Winchester, KY 40391, 4 beds, 1 bath

$225,000

4 beds1 bath1,743 sq ft

218 E Washington St, Winchester, KY 40391

Property at 23 Kittison Dr, Winchester, KY 40391, 3 beds, 2 baths

$235,000

3 beds2 baths1,346 sq ft

23 Kittison Dr, Winchester, KY 40391

Property at 605 College St, Winchester, KY 40391, 2 beds, 1 bath

$230,000

2 beds1 bath1,484 sq ft

605 College St, Winchester, KY 40391

Property at 1508 Ford Hampton Rd, Winchester, KY 40391, 2 beds, 1 bath

$325,000

2 beds1 bath1,531 sq ft

1508 Ford Hampton Rd, Winchester, KY 40391

Property at 528 Estes Dr, Winchester, KY 40391, 3 beds, 2 baths

$249,900

3 beds2 baths1,904 sq ft

528 Estes Dr, Winchester, KY 40391

Property at 130 E Broadway St, Winchester, KY 40391, 5 beds, 3 baths

$245,000

5 beds3 baths2,445 sq ft

130 E Broadway St, Winchester, KY 40391

Property at 600 Boone Ave, Winchester, KY 40391, 4 beds, 4 baths

$612,900

4 beds4 baths4,374 sq ft

600 Boone Ave, Winchester, KY 40391

Property at 228 Jackson St, Winchester, KY 40391, 3 beds, 1 bath

$146,000

3 beds1 bath1,020 sq ft

228 Jackson St, Winchester, KY 40391

Property at 20 Bon-haven Ave, Winchester, KY 40391, 4 beds, 3 baths

$275,000

4 beds3 baths1,850 sq ft

20 Bon-haven Ave, Winchester, KY 40391

Property at 39 S Highland St, Winchester, KY 40391, 2 beds, 1 bath

$102,000

2 beds1 bath552 sq ft

39 S Highland St, Winchester, KY 40391

Property at 42 Mockingbird Valley Rd, Winchester, KY 40391, 3 beds, 2.5 baths

$457,900

3 beds2.5 baths2,961 sq ft

42 Mockingbird Valley Rd, Winchester, KY 40391

Property at 175 Magnolia St, Winchester, KY 40391, 3 beds, 1 bath

$199,000

3 beds1 bath1,046 sq ft

175 Magnolia St, Winchester, KY 40391

Property at 1363 Clintonville Rd, Winchester, KY 40391, 2 beds, 1 bath

$312,975

2 beds1 bath1,116 sq ft

1363 Clintonville Rd, Winchester, KY 40391

Property at 40 Garner St, Winchester, KY 40391, 3 beds, 1 bath

$210,500

3 beds1 bath1,354 sq ft

40 Garner St, Winchester, KY 40391

Property at 410 W Lexington Ave, Winchester, KY 40391, 6 beds, 4 baths

$340,000

6 beds4 baths4,456 sq ft

410 W Lexington Ave, Winchester, KY 40391

Property at 150 Cook Ave, Winchester, KY 40391, 3 beds, 1 bath

$144,000

3 beds1 bath805 sq ft

150 Cook Ave, Winchester, KY 40391

Property at 102 W Hickman St, Winchester, KY 40391, 2 beds, 1 bath

$171,000

2 beds1 bath870 sq ft

102 W Hickman St, Winchester, KY 40391

Property at 101 E Lexington Ave, Winchester, KY 40391, 5 beds, 3 baths

$388,000

5 beds3 baths2,762 sq ft

101 E Lexington Ave, Winchester, KY 40391

Property at 104 Colby Hills Dr, Winchester, KY 40391, 4 beds, 2 baths

$439,000

4 beds2 baths1,950 sq ft

104 Colby Hills Dr, Winchester, KY 40391

Property at 1509 Boonesboro Rd, Winchester, KY 40391

$2,000,000

— beds— baths— sq ft

1509 Boonesboro Rd, Winchester, KY 40391

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Vintage Homes for Sale in Winchester

There are currently 37 vintage homes for sale in Winchester at a median listing price of $265K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Winchester stay on the market for 56 days. This map is refreshed with the newest listings in Winchester every 15 minutes.

In the past month, 17 homes have been sold in Winchester. In addition to houses in Winchester, there were also 0 condos, 4 townhouses, and 5 multi-family units for sale in Winchester last month. Winchester is a minimally walkable city in Kentucky with a Walk Score of 36. Winchester is home to approximately 17,893 people and 8,688 jobs. Find your dream home in Winchester using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Winchester are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Winchester. Our Winchester real estate stats and trends will give you more information about home buying and selling trends in Winchester. If you're looking to sell your home in the Winchester area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Winchester with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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