The most expensive neighborhoods in Owensboro

Homebuyers and sellers are navigating a slow and expensive housing market, with rising prices and stagnant demand keeping many on the sidelines. This comes amid rising economic uncertainty and growing wealth concentration. But luxury homes—multimillion-dollar estates, sleek penthouses, and one-of-a-kind custom builds—are still selling, even as most buyers pull back.

Most people can't afford high-end homes, although they're still fun to dream about. So, to highlight where luxury real estate is commanding the highest prices, Redfin analyzed the most expensive neighborhoods in the Owensboro metro area—and showcased a few of the area's standout listings (when possible).

Note: Redfin's analysis focused on metro areas, meaning some neighborhoods fell within smaller nearby cities. Listings and data were gathered on October 15, 2025.

#1. Hillcrest (Owensboro, KY)

Median sale price: $415,000 | Median days on market: 38 days

1318 Woodmere Ln, Owensboro, KY 42303
- List price: $524,900
- Beds: 5 | Baths: 3.5 | Square feet: 4,196
- See 1318 Woodmere Ln, Owensboro, KY 42303 on Redfin.com

4230 Edgewood Ct, Owensboro, KY 42303
- List price: $329,500
- Beds: 3 | Baths: 2 | Square feet: 1,953
- See 4230 Edgewood Ct, Owensboro, KY 42303 on Redfin.com

4524 Loftwood Dr, Owensboro, KY 42303
- List price: $349,900
- Beds: 4 | Baths: 2.5 | Square feet: 2,376
- See 4524 Loftwood Dr, Owensboro, KY 42303 on Redfin.com

4950 Ridge Creek Rd, Owensboro, KY 42303
- List price: $589,900
- Beds: 4 | Baths: 2.5 | Square feet: 3,123
- See 4950 Ridge Creek Rd, Owensboro, KY 42303 on Redfin.com

#2. Shifley (Owensboro, KY)

Median sale price: $257,500 | Median days on market: 25 days

1664 Roosevelt Rd, Owensboro, KY 42301
- List price: $299,900
- Beds: 4 | Baths: 4 | Square feet: 3,220
- See 1664 Roosevelt Rd, Owensboro, KY 42301 on Redfin.com

2205 Turnbury Cv, Owensboro, KY 42301
- List price: $429,900
- Beds: 3 | Baths: 3 | Square feet: 2,719
- See 2205 Turnbury Cv, Owensboro, KY 42301 on Redfin.com

2516 Carryback Ct, Owensboro, KY 42301
- List price: $214,900
- Beds: 3 | Baths: 1 | Square feet: 1,421
- See 2516 Carryback Ct, Owensboro, KY 42301 on Redfin.com

2520 Middleground Dr N, Owensboro, KY 42301
- List price: $225,000
- Beds: 3 | Baths: 2 | Square feet: 1,595
- See 2520 Middleground Dr N, Owensboro, KY 42301 on Redfin.com

#3. Wesleyan (Owensboro, KY)

Median sale price: $245,000 | Median days on market: 6 days

2548 Farrier Pl, Owensboro, KY 42301
- List price: $329,900
- Beds: 3 | Baths: 2.5 | Square feet: 2,222
- See 2548 Farrier Pl, Owensboro, KY 42301 on Redfin.com

2641 Windsor Ave, Owensboro, KY 42301
- List price: $205,000
- Beds: 3 | Baths: 1.5 | Square feet: 1,356
- See 2641 Windsor Ave, Owensboro, KY 42301 on Redfin.com

3418 Queens Way, Owensboro, KY 42301
- List price: $269,900
- Beds: 3 | Baths: 2 | Square feet: 2,092
- See 3418 Queens Way, Owensboro, KY 42301 on Redfin.com

3610 Monticello Dr, Owensboro, KY 42301
- List price: $375,900
- Beds: 3 | Baths: 3 | Square feet: 3,132
- See 3610 Monticello Dr, Owensboro, KY 42301 on Redfin.com

#4. Dogwood Azalea (Owensboro, KY)

Median sale price: $241,450 | Median days on market: 7 days

1053 Hill Ave, Owensboro, KY 42301
- List price: $595,900
- Beds: 3 | Baths: 2.5 | Square feet: 3,537
- See 1053 Hill Ave, Owensboro, KY 42301 on Redfin.com

1212 Hill Ave, Owensboro, KY 42301
- List price: $264,900
- Beds: 4 | Baths: 2 | Square feet: 1,870
- See 1212 Hill Ave, Owensboro, KY 42301 on Redfin.com

1314 Werner Ave, Owensboro, KY 42301
- List price: $124,999
- Beds: 2 | Baths: 1 | Square feet: 898
- See 1314 Werner Ave, Owensboro, KY 42301 on Redfin.com

816 W 13Th St, Owensboro, KY 42301
- List price: $69,999
- Beds: 2 | Baths: 1 | Square feet: 1,424
- See 816 W 13Th St, Owensboro, KY 42301 on Redfin.com

#5. Seven Hills (Owensboro, KY)

Median sale price: $212,000 | Median days on market: 24 days

1408 Jackson St, Owensboro, KY 42303
- List price: $79,999
- Beds: 1 | Baths: 1 | Square feet: 608
- See 1408 Jackson St, Owensboro, KY 42303 on Redfin.com

1714 Leitchfield Rd, Owensboro, KY 42303
- List price: $199,900
- Beds: 4 | Baths: 2 | Square feet: 1,498
- See 1714 Leitchfield Rd, Owensboro, KY 42303 on Redfin.com

2644 Epworth Ln, Owensboro, KY 42303
- List price: $174,900
- Beds: 3 | Baths: 1 | Square feet: 1,189
- See 2644 Epworth Ln, Owensboro, KY 42303 on Redfin.com

2942 Trails Way, Owensboro, KY 42303
- List price: $279,500
- Beds: 3 | Baths: 2 | Square feet: 1,505
- See 2942 Trails Way, Owensboro, KY 42303 on Redfin.com