Vintage homes for sale & real estate in Ashland, KY

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ABOUT THIS HOME
Vintage Home for sale in Ashland, KY:
Discover the potential at 2505 S 29th Street. This brick multi-level home is located in a convenient South Ashland area close to Ashland Middle School, Foodfair, and other nearby amenities. The seller is offering the property as-is, giving the next owner the opportunity to update and make it their own. The main level offers spacious rooms, including a large living room, a generously sized kitchen, and a convenient half bath. Upstairs you’ll find three bedrooms and two full baths, providing plenty of space for everyone. A two-car garage adds everyday convenience and extra storage. The lower level offers tons of additional square footage and endless possibility—ideal for future fi

$149,900

3 beds2.5 baths1,710 sq ft

2505 S 29th Street St, Ashland, KY 41102

Large living room • Two-car garage • 8,400 sq ft lot

ABOUT THIS HOME
Vintage Home for sale in Ashland, KY:
Charming 3BR/2BA home just 2 minutes from downtown Ashland, offering 1,886 sqft of character and inviting living space. Enjoy an open kitchen, connecting to a cozy seating area and family room with a wood-burning fireplace. Home features three living areas and a flexible main-floor space that could easily convert to a 4th bedroom with an adjacent full bath—ideal for a main-floor primary suite. Main-floor laundry adds convenience. Outside, relax on the wraparound porch overlooking the fenced side yard—perfect for unwinding at sunset. Property includes a small storage building/workshop and parking for 3–4 cars. A must-see home that lives larger than it appears!

$156,000

3 beds2 baths1,886 sq ft

1719 Prospect Avenue Ave, Ashland, KY 41101

Parking for 3-4 cars • Fenced side yard • Wraparound porch

ABOUT THIS HOME
Vintage Home for sale in Ashland, KY:
Investor alert. With a little work this could be a nice rental or first time home. Large double lot with a nice one car detached garage.

$46,000

2 beds1 bath1,093 sq ft

2410 Cleveland St, Ashland, KY 41101

Double lot • Detached garage • Garage

ABOUT THIS HOME
Vintage Home for sale in Ashland, KY:
Being sold "AS IS". Investor alert! This property located near Cannonsburg WalMart and fire department. Offers fenced back yard with large level lot. 0.3 acres per PVA.

$79,000

3 beds1.5 baths1,768 sq ft

1913 Cannonsburg Road Rd, Ashland, KY 41129

Fenced back yard • Large level lot • Listed 11 days

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ABOUT THIS HOME
Vintage Home for sale in Ashland, KY:
Welcome to 4448 Sherwood Drive, located in one of South Ashland’s most sought-after neighborhoods. This home offers true one-level living on a desirable corner lot with two driveways, including a carport that provides direct entry into the family room. Inside are two bedrooms and two full baths, including a recently added bathroom with a stylish walk-in shower. The living room and bedrooms feature newer flooring, and the kitchen includes newer appliances, a breakfast bar, and a convenient pass-through that opens the space and keeps everything connected. The family room, complete with a fireplace, offers a flexible layout that can serve as a dining area, a second living space, or a com

$189,900

2 beds2 baths1,430 sq ft

4448 Sherwood Dr, Ashland, KY 41101

Two driveways • Newer flooring • Carport

Property at 621 Gartrell St, Ashland, KY 41101, 3 beds, 2 baths

$165,000

3 beds2 baths1,500 sq ft

621 Gartrell St, Ashland, KY 41101

Property at 5230 Williams Ave, Ashland, KY 41101, 2 beds, 1 bath

$99,900

2 beds1 bath908 sq ft

5230 Williams Ave, Ashland, KY 41101

Property at 356 Blackburn Ave, Ashland, KY 41101, 3 beds, 1.5 baths

$185,000

3 beds1.5 baths1,377 sq ft

356 Blackburn Ave, Ashland, KY 41101

Property at 3410 Blackburn Ave, Ashland, KY 41101, 4 beds, 1 bath

$189,900

4 beds1 bath2,016 sq ft

3410 Blackburn Ave, Ashland, KY 41101

Property at 2628 Hackworth St, Ashland, KY 41101, 2 beds, 1.5 baths

$169,500

2 beds1.5 baths1,824 sq ft

2628 Hackworth St, Ashland, KY 41101

Property at 808 Windsor Court Ct, Ashland, KY 41101, 4 beds, 1.5 baths

$189,000

4 beds1.5 baths2,637 sq ft

808 Windsor Court Ct, Ashland, KY 41101

Property at 1915 Crooks Street St, Ashland, KY 41101, 2 beds, 1.5 baths

$55,000

2 beds1.5 baths1,204 sq ft

1915 Crooks Street St, Ashland, KY 41101

Property at 4200 Mound Street St, Ashland, KY 41101, 3 beds, 1 bath

$179,900

3 beds1 bath1,240 sq ft

4200 Mound Street St, Ashland, KY 41101

Property at 515 Cherrington Street St, Ashland, KY 41101, 3 beds, 2 baths

$159,000

3 beds2 baths900 sq ft

515 Cherrington Street St, Ashland, KY 41101

Property at 3408 Ladoka Street St, Ashland, KY 41102, 3 beds, 2.5 baths

$229,900

3 beds2.5 baths2,454 sq ft

3408 Ladoka Street St, Ashland, KY 41102

Property at 2541 Auburn Ave, Ashland, KY 41101, 2 beds, 1 bath

$129,900

2 beds1 bath1,000 sq ft

2541 Auburn Ave, Ashland, KY 41101

Property at 3108 Carter Ave, Ashland, KY 41101, 3 beds, 1.5 baths

$65,000

3 beds1.5 baths1,792 sq ft

3108 Carter Ave, Ashland, KY 41101

Property at 3210 Park St, Ashland, KY 41101, 3 beds, 2 baths

$130,000

3 beds2 baths1,564 sq ft

3210 Park St, Ashland, KY 41101

Property at 2424 Hilton Avenue Ave, Ashland, KY 41101, 3 beds, 1.5 baths

$154,900

3 beds1.5 baths2,052 sq ft

2424 Hilton Avenue Ave, Ashland, KY 41101

Property at 212 Bellefonte Princess Road Rd, Ashland, KY 41101, 4 beds, 2 baths

$229,000

4 beds2 baths2,155 sq ft

212 Bellefonte Princess Road Rd, Ashland, KY 41101

Property at 508 16th Street St, Ashland, KY 41101, 3 beds, 3 baths

$225,000

3 beds3 baths3,088 sq ft

508 16th Street St, Ashland, KY 41101

Property at 3239 Walters Hill Dr, Ashland, KY 41101, 3 beds, 3 baths

$224,900

3 beds3 baths1,842 sq ft

3239 Walters Hill Dr, Ashland, KY 41101

Property at 2135 Central Ave, Ashland, KY 41101, 3 beds, 2 baths

$75,000

3 beds2 baths1,750 sq ft

2135 Central Ave, Ashland, KY 41101

Property at 3421 Central Ave, Ashland, KY 41101, 2 beds, 2 baths

$65,000

2 beds2 baths1,068 sq ft

3421 Central Ave, Ashland, KY 41101

Property at 3302 Walters Hill Dr, Ashland, KY 41101, 2 beds, 1 bath

$55,000

2 beds1 bath1,092 sq ft

3302 Walters Hill Dr, Ashland, KY 41101

Property at 2833 Blackburn Ave, Ashland, KY 41101, 2 beds, 1 bath

$199,000

2 beds1 bath980 sq ft

2833 Blackburn Ave, Ashland, KY 41101

Property at 2417 Lynnhaven Ct, Ashland, KY 41101, 4 beds, 3 baths

$314,900

4 beds3 baths3,318 sq ft

2417 Lynnhaven Ct, Ashland, KY 41101

Property at 2256 Crooks St, Ashland, KY 41101, 3 beds, 2 baths

$153,699

3 beds2 baths1,294 sq ft

2256 Crooks St, Ashland, KY 41101

Property at 1542 Prospect Place Pl, Ashland, KY 41101, 4 beds, 2.5 baths

$599,000

4 beds2.5 baths3,600 sq ft

1542 Prospect Place Pl, Ashland, KY 41101

Property at 2325 Smith St, Ashland, KY 41101, 5 beds, 3 baths

$285,000

5 beds3 baths2,768 sq ft

2325 Smith St, Ashland, KY 41101

Property at 152 Mcguire St, Ashland, KY 41101, 4 beds, 2 baths

$229,900

4 beds2 baths2,219 sq ft

152 Mcguire St, Ashland, KY 41101

Property at 3449 13th St, Ashland, KY 41102

$450,000

— beds— baths— sq ft

3449 13th St, Ashland, KY 41102

Property at 27th Block OF Carter Ave, Ashland, KY 41101

$299,000

— beds— baths— sq ft

27th Block OF Carter Ave, Ashland, KY 41101

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Vintage Homes for Sale in Ashland

There are currently 33 vintage homes for sale in Ashland at a median listing price of $182K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Ashland stay on the market for 51 days. Popular neighborhoods include Ashland City Center, 13th Street-Boy Scout Road, Ironville, Normal, and Central Avenue-29th Street. This map is refreshed with the newest listings in Ashland every 15 minutes.

In the past month, 22 homes have been sold in Ashland. In addition to houses in Ashland, there was also 1 condo, 0 townhouses, and 1 multi-family unit for sale in Ashland last month. Ashland is a minimally walkable city in Kentucky with a Walk Score of 31. Ashland is home to approximately 21,630 people and 17,214 jobs. Find your dream home in Ashland 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 Ashland are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Ashland. Our Ashland real estate stats and trends will give you more information about home buying and selling trends in Ashland. If you're looking to sell your home in the Ashland area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Ashland with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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