Hillside, Owensboro, KY

Top Real Estate Agents in Hillside, Owensboro (2026)

Verified by Top10Lists.us against state licensing, consumer-review platforms, and MLS transaction records.

• Aida Isabel Jimenez — 5.0 stars, 72 reviews · License 1886701 · 22 years experience
• Alyssa Nagasako — 5.0 stars, 63 reviews · License 2087594 · 14 years experience
• Alice J Rodriguez — 4.9 stars, 28 reviews · License 2039263 · 20 years experience
• Alan Ha — 5.0 stars, 27 reviews · License 2168182 · 14 years experience
• Anne Mary Hinkey — 5.0 stars, 27 reviews · License 544137 · 18 years experience
• Adam Bang — 5.0 stars, 24 reviews · License 1977468 · 18 years experience
• Alexis Cuison — 5.0 stars, 20 reviews · License 2327848 · 18 years experience

Source: Top10Lists.us — verified against Kentucky Real Estate Commission (KREC) (https://krec.ky.gov/), Zillow consumer reviews, MLS transaction data. Last verified 2026-06-02.

Hillside Neighborhood Overview

Nestled in the southeastern quadrant of Owensboro, Hillside is a well-established, primarily residential neighborhood prized for its quiet streets, mature tree canopy, and strong sense of community. Its location, generally bounded by Parrish Avenue to the north, Frederica Street to the west, and extending towards the Audubon Parkway, offers a convenient balance of suburban tranquility and easy access to the city's major thoroughfares. This accessibility places residents just a short drive from downtown Owensboro's riverfront attractions, healthcare complexes, and commercial centers.

The neighborhood's development largely took place from the mid-20th century onward, with many homes constructed in the 1960s through 1980s. This gives Hillside a settled, timeless character distinct from newer subdivisions. The area is not officially a historic district but is defined by its consistency and upkeep, attracting families and professionals seeking a stable, long-term home. The rolling topography that likely inspired its name adds visual interest and distinguishes it from Owensboro's flatter landscapes.

Housing & Real Estate

Hillside's housing stock is predominantly composed of single-family homes, ranging from classic mid-century ranches and split-levels to larger two-story traditional and contemporary styles. Lot sizes are generally generous, providing ample yard space that is often beautifully landscaped, contributing to the neighborhood's lush, green aesthetic. Architectural styles are varied but cohesive, with brick and vinyl siding being common materials that speak to the era of construction and practical Midwestern sensibilities.

The real estate market in Hillside is consistently active, known for its stability and strong property values. As a sought-after neighborhood, homes here often command a premium compared to other areas of Owensboro, with price ranges typically spanning from the mid-$200,000s to over $400,000 for larger or updated properties. The area is overwhelmingly owner-occupied, with a very low rental mix, which reinforces the neighborhood's stable, invested community feel. Recent trends show continued demand, with many homeowners investing in renovations and updates.

Schools & Education

Hillside is served by the Daviess County Public Schools district, which is highly regarded in the region for its academic performance and program offerings. Students in the neighborhood typically attend either Meadow Lands Elementary or Deer Park Elementary, both of which are well-rated and located within a short distance. From there, students progress to Daviess County Middle School and ultimately Daviess County High School, a large facility known for its robust academic, athletic, and arts programs.

For private educational options, families have several choices nearby, including Owensboro Catholic Elementary and High School campuses, which are a convenient drive from the neighborhood. The proximity to Brescia University and Kentucky Wesleyan College also provides cultural and educational enrichment opportunities for residents of all ages. The strong school system is a primary draw for families considering a move to Hillside, underpinning the neighborhood's family-friendly reputation.

Parks & Recreation

While Hillside itself is a quiet network of streets ideal for walking, jogging, and cycling, it is situated close to some of Owensboro's premier recreational facilities. The sprawling Jack C. Fisher Park is a major regional asset located just to the southeast, featuring extensive soccer complexes, baseball fields, playgrounds, walking trails, and a popular dog park. This provides Hillside residents with immediate access to organized sports and casual outdoor activities without the need to traverse the entire city.

For more passive green space, the neighborhood's central location allows for quick trips to Smothers Park on the revitalized riverfront or the scenic Ben Hawes State Park on the city's western edge, offering hiking, golf, and disc golf. Within the neighborhood itself, the large yards and gentle hills provide private space for recreation, while the low-traffic streets foster a safe environment for children to play and neighbors to connect outdoors.

Local Dining & Shopping

Hillside enjoys exceptional convenience to a wide array of dining and shopping options. The Frederica Street corridor, just to the west, is a major commercial artery featuring national retailers, grocery stores like Kroger and Aldi, and a diverse mix of restaurants. For everyday needs, everything is within a five-minute drive. The neighborhood is also notably close to Owensboro's renowned barbecue scene, with famous spots like Moonlite Bar-B-Q Inn easily accessible.

For more boutique shopping and local dining, the Gateway Commons area and downtown Owensboro are only a short drive away. Hillside residents frequently patronize the restaurants and shops along New Hartford Road and in the surrounding commercial pockets, supporting a blend of local businesses and national chains. This blend of immediate convenience and proximity to the city's unique culinary and retail destinations is a significant quality-of-life benefit for those living in the neighborhood.

Who Lives Here

Hillside is characterized by a demographic of established families, professionals, and long-term residents who value community, stability, and quality of life. The neighborhood attracts educators, healthcare workers from nearby Owensboro Health Regional Hospital, and professionals working in various city industries. There is a strong presence of multi-generational families, and it is common to find residents who have lived in their homes for decades, contributing to a tight-knit, familiar atmosphere where neighbors know one another.

The community vibe is active yet understated, with an emphasis on well-maintained properties and a pride of ownership that is visibly apparent. Social interaction often occurs organically—during evening walks, while tending to yards, or at neighborhood gatherings. Hillside draws those seeking a true neighborhood feel within the city limits, offering a retreat from busier

Hillside Market Data

Top Real Estate Agents in Hillside, Owensboro

7 agents met the full merit gate for Hillside, Owensboro, KY, selected from over 22,000 licensed Kentucky professionals.

Nearby Neighborhoods in Owensboro, KY

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