Winslow, KY homes for sale & real estate

12 homes

Sort:

Recommended

430 Pierce St, Ashland, KY 41101
430 Pierce St, Ashland, KY 41101
430 Pierce St, Ashland, KY 41101
ABOUT THIS HOME
Winslow, KY Homes for Sale
Brick and vinyl ranch with covered front porch, close to all amenities, attached garage. Hold Harmless agreement to be signed by all persons before entering.

$41,600

3 beds1 bath1,379 sq ft

430 Pierce St, Ashland, KY 41101

6,098 sq ft lot • Garage • Car-dependent

152 Mcguire St, Ashland, KY 41101
152 Mcguire St, Ashland, KY 41101
152 Mcguire St, Ashland, KY 41101
ABOUT THIS HOME
Winslow, KY Homes for Sale
Venerable, older home in the classic style with bright, large rooms, modern kitchen, formal dining and living rooms, four bedrooms upstairs with a craft , sewing or baby's room. There are two bathrooms, one on each floor, porches for enjoying the outside and some unique landscaping with flowers. The yard is level and expansive. ADU (Auxillary Dwelling Unit - The two car garage has been converted to a one-bedroom cottage that is currently occupied by a family member. The kitchen and bathroom are both modern. This ADU could provide a home for a family member or could be rented. Extra LOT- Yep, adjacent to the home is an extra lot that measure 50' xx 140' which is in grass and was a garden are

$229,900

4 beds2 baths2,219 sq ft

152 Mcguire St, Ashland, KY 41101

0.32 acre lot • Car-dependent

2425-2427 Boone St, Ashland, KY 41101
2425-2427 Boone St, Ashland, KY 41101
2425-2427 Boone St, Ashland, KY 41101
ABOUT THIS HOME
Winslow, KY Homes for Sale
Here's your chance to own an income producing property! Tenants already in place and several tenants are 5 year tenants. 2425 - 4-Plex 2 Bed 1 Bath 800 sq. ft. - each unit has washer & dryer hook-ups-New flooring & new HV/AC 6/2025 - Tenant pays all utilities - Rent- $750 2427 -Townhouse - 2 Bed 1 Bath & 2 half baths - 1200 sq. ft. - each unit has washer & dryer hook-ups- Patio & fireplace - Tenant pays all utilities Rent is $900 Income of 4,800 monthly Here's your chance to start your investor portfolio!

$460,000

— beds— baths— sq ft

2425-2427 Boone St, Ashland, KY 41101

0.41 acre lot • Car-dependent

569 1/2 Blackburn Avenue Ave, Ashland, KY 41102
569 1/2 Blackburn Avenue Ave, Ashland, KY 41102
569 1/2 Blackburn Avenue Ave, Ashland, KY 41102
ABOUT THIS HOME
Winslow, KY Homes for Sale
Two Home's for the price of 1! 569 1/2 Blackburn Avenue is currently rented at $300 per month, tenant has been there for a very long time and good payment history. 2901 West Virginia Street is vacant. Get both homes for 1 great price, outstanding investment opportunity! 2901 West Virginia Street can be purchased separately as well at a list price of $59,900 See MLS 58672 for details.

$82,900

2 beds1 bath1,000 sq ft

569 1/2 Blackburn Avenue Ave, Ashland, KY 41102

Car-dependent

601 Pollard Road Rd, Ashland, KY 41101
601 Pollard Road Rd, Ashland, KY 41101
601 Pollard Road Rd, Ashland, KY 41101
ABOUT THIS HOME
Winslow, KY Homes for Sale
Square footage of lot and house per PVA.

$59,000

1 bed1 bath650 sq ft

601 Pollard Road Rd, Ashland, KY 41101

7,500 sq ft lot • Car-dependent

$49,900

— beds— baths— sq ft

0 Dee Ct, Ashland, KY 41101

Property at 0 Kirk St, Ashland, KY 41101

$149,900

— beds— baths— sq ft

0 Kirk St, Ashland, KY 41101

Property at 3200 Block Cogan St, Ashland, KY 41102

$40,000

— beds— baths— sq ft

3200 Block Cogan St, Ashland, KY 41102

Property at 0 Roberts Dr, Ashland, KY 41101

$25,000

— beds— baths— sq ft

0 Roberts Dr, Ashland, KY 41101

Property at 0 Boone St, Ashland, KY 41101

$19,900

— beds— baths— sq ft

0 Boone St, Ashland, KY 41101

Property at 0 Pollard Rd, Ashland, KY 41101

$125,000

— beds— baths— sq ft

0 Pollard Rd, Ashland, KY 41101

Property at Lot 5, 6, 7, 8 Gloria Ave, Ashland, KY 41101

$214,900

— beds— baths— sq ft

Lot 5, 6, 7, 8 Gloria Ave, Ashland, KY 41101

Viewing page 1 of 1

End of results

Nearby homes that match your criteria

620 Westview Dr, Ashland, KY 41102
620 Westview Dr, Ashland, KY 41102
620 Westview Dr, Ashland, KY 41102
ABOUT THIS HOME
Winslow, KY Homes for Sale
Looking for Affordable and 1 level? This Completely Renovated home is Ready and Priced to sell. Get keys at closing. Located on a quite street. Beautiful Updated kitchen with Stainless steel Appliances. 3 bedroom with spacious closets. Updated bath. Large backyard and nice size shed for extra storage.

$159,900

3 beds1 bath950 sq ft

620 Westview Dr, Ashland, KY 41102

Car-dependent

622 Westview Dr, Ashland, KY 41102
622 Westview Dr, Ashland, KY 41102
622 Westview Dr, Ashland, KY 41102
ABOUT THIS HOME
Winslow, KY Homes for Sale
This gorgeous home is ready to move into! Located on a quite street. Get your keys at closing! This 3 bedroom 2 full bath is completely renovated! Gorgeous kitchen with granite countertops, all stainless steel appliances. Open floor plan with large living space, dining area plus a pantry! Main suite has its own full bath. Bedrooms are spacious, Newer LVP flooring throughout home. Large attached garage. Back deck with private yard. Priced affordable.

$179,900

3 beds2 baths1,200 sq ft

622 Westview Dr, Ashland, KY 41102

6,675 sq ft lot • Garage • Car-dependent

2332 Sellars Street St, Ashland, KY 41101
2332 Sellars Street St, Ashland, KY 41101
2332 Sellars Street St, Ashland, KY 41101

$159,500

3 beds1.5 baths1,348 sq ft

2332 Sellars Street St, Ashland, KY 41101

6,250 sq ft lot • Car-dependent

3217 Devore Street St, Ashland, KY 41102
3217 Devore Street St, Ashland, KY 41102
3217 Devore Street St, Ashland, KY 41102
ABOUT THIS HOME
Winslow, KY Homes for Sale
Welcome to 3217 Devore Street in Ashland, KY! This charming 2-bedroom, 1-bath home offers far more than meets the eye, with two separate living areas—one on the main floor and another in the finished basement—giving you plenty of space to spread out and make it your own. Step outside and you’ll find multiple decks that invite you to relax and enjoy the day, whether it’s sipping morning coffee or unwinding in the evening breeze. Sitting on a large, flat lot, the property also features a detached two-car garage and gorgeous finishes throughout. Tucked just seconds from Oakview Elementary in one of Ashland’s most sought-after neighborhoods, this home blends style,

$199,500

2 beds1 bath2,014 sq ft

3217 Devore Street St, Ashland, KY 41102

6,000 sq ft lot • 2 garage spots • Car-dependent

1636 Maryland Parkway Pkwy, Ashland, KY 41101
1636 Maryland Parkway Pkwy, Ashland, KY 41101
1636 Maryland Parkway Pkwy, Ashland, KY 41101
ABOUT THIS HOME
Winslow, KY Homes for Sale
Welcome to 1636 Maryland Parkway, a charming colonial-style 2-story home nestled in a well-established neighborhood near Hager Elementary School. This 3-bedroom, 2-bath home offers 1,350 square feet of living space, an updated metal roof, and a full, unfinished basement for additional storage. Enjoy the privacy of the level, fenced-in back yard and spacious back deck ideal for pets, play, or quiet evenings of relaxing, or for fun gatherings and entertaining. Stylish updates include modern bathrooms and subway tile, updated vanities, a sliding barn door, and a convenient main-level laundry area. Don’t miss this timeless beauty! Schedule your private tour today and see why this Ashland

$139,900

3 beds2 baths1,350 sq ft

1636 Maryland Parkway Pkwy, Ashland, KY 41101

8,712 sq ft lot • Somewhat walkable

523 New Buckley Rd, Ashland, KY 41102
523 New Buckley Rd, Ashland, KY 41102
523 New Buckley Rd, Ashland, KY 41102
ABOUT THIS HOME
Winslow, KY Homes for Sale
corner location , nice screened in rear porch cent heat air

$192,500

3 beds1.5 baths1,620 sq ft

523 New Buckley Rd, Ashland, KY 41102

2 garage spots • Car-dependent

Property at 815 Wheatley Road (ww) Rd, Ashland, KY 41102, 4 beds, 3.5 baths

$199,900

4 beds3.5 baths2,040 sq ft

815 Wheatley Road (ww) Rd, Ashland, KY 41102

Property at 2429 Carroll Street St, Ashland, KY 41102, 4 beds, 1 bath

$99,500

4 beds1 bath1,125 sq ft

2429 Carroll Street St, Ashland, KY 41102

Property at 2720 Bruce Dr, Ashland, KY 41102, 4 beds, 2 baths

$184,900

4 beds2 baths1,582 sq ft

2720 Bruce Dr, Ashland, KY 41102

Property at 2920 Ranch Road Rd, Ashland, KY 41102, 5 beds, 3 baths

$206,000

5 beds3 baths3,134 sq ft

2920 Ranch Road Rd, Ashland, KY 41102

Property at 2660 Main St, Ashland, KY 41101

$299,900

— beds— baths— sq ft

2660 Main St, Ashland, KY 41101

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

$689,900

4 beds2.5 baths3,600 sq ft

1542 Prospect Place Pl, Ashland, KY 41101

Property at 1338 High St, Ashland, KY 41102, 2 beds, 1 bath

$54,900

2 beds1 bath850 sq ft

1338 High St, Ashland, KY 41102

Property at 1812 Creston Place Pl, Ashland, KY 41101, 4 beds, 2 baths

$229,900

4 beds2 baths2,965 sq ft

1812 Creston Place Pl, Ashland, KY 41101

Property at 3001 29th St, Ashland, KY 41101, 3 beds, 1 bath

$189,900

3 beds1 bath1,644 sq ft

3001 29th St, Ashland, KY 41101

Property at 1918 Prospect Ave, Ashland, KY 41101, 3 beds, 1 bath

$60,000

3 beds1 bath1,374 sq ft

1918 Prospect Ave, Ashland, KY 41101

Property at 2901 West Virginia Street St, Ashland, KY 41102, 1 bed, 1 bath

$59,900

1 bed1 bath800 sq ft

2901 West Virginia Street St, Ashland, KY 41102

Property at 1908 Weymouth Drive Dr, Ashland, KY 41101, 4 beds, 3 baths

$299,900

4 beds3 baths2,312 sq ft

1908 Weymouth Drive Dr, Ashland, KY 41101

Property at 217 Iowa St. St, Ashland, KY 41102, 3 beds, 1 bath

$89,900

3 beds1 bath1,225 sq ft

217 Iowa St. St, Ashland, KY 41102

Property at E Altamont Dr, Ashland, KY 41101

$29,500

— beds— baths— sq ft

E Altamont Dr, Ashland, KY 41101

Average home prices near Winslow, KY

Cities

Neighborhoods

Ashland City Center homes for sale
$77,000
13th Street-Boy Scout Road homes for sale
$189,900
Normal homes for sale
$130,000
Central Avenue-29th Street homes for sale
$139,000
Valley View homes for sale
$184,900
Oakview-Blackburn homes for sale
$218,900
Summit homes for sale
$198,500

Winslow, KY real estate trends

All Home Types trends in Winslow, KY

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$75,000

+15.4% YoY | Jun 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Jun 2025

Growth

% YoY

Winslow, KY

$75,000

+15.4%

See more Winslow, KY market insights

More to explore in Winslow, KY

How to buy a house in Winslow, KY

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Kentucky

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Subsidiaries

Countries

United States

Canada

Updated January 2023: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, TITLE FORWARD, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

Rocket Mortgage is an affiliated business of Redfin. All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York. For additional information on Rocket Mortgage or to receive lending services in the State of New York, please visit RocketMortgage.com.

Rocket Mortgage, LLC, Rocket Homes Real Estate LLC, Rocket Card, LLC, RockLoans Marketplace LLC (doing business as Rocket Loans), and Rocket Money, Inc., are separate operating subsidiaries of Rocket Limited Partnership. Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company is a separate legal entity operated and managed through its own management and governance structure. Rocket Limited Partnership is an indirect, wholly owned subsidiary of Rocket Companies, Inc. (NYSE: RKT).

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.