Osprey Property Management Blog

Top 5 Neighborhoods in Chesapeake, VA for Real Estate Investors

Written by Osprey Property Management | May 6, 2025 4:07:00 PM

Looking to invest in a growing real estate market with strong rental potential and long-term value? Chesapeake, VA is one of the most investor-friendly cities in the region. 

Whether you're a first-time investor or building your portfolio, the right neighborhood can make all the difference in your return on investment.

Let’s explore the best areas to invest in Chesapeake and why this city stands out.

Why Chesapeake Is an Investor-Friendly Market

Chesapeake offers a unique mix of suburban comfort and strong economic drivers, making it a smart choice for real estate investment.

Located in the heart of Coastal Virginia, Chesapeake is part of the Hampton Roads metro area. It's home to a diverse population, top-rated schools, and plenty of natural beauty. 

However, for investors, the real appeal lies in its stability and demand.

Key Benefits for Real Estate Investors in Chesapeake

Chesapeake continues to attract real estate investors for several reasons:

  • High rental demand due to its proximity to several major military bases, including Naval Station Norfolk and Joint Expeditionary Base Little Creek.
  • Consistent property appreciation and steady population growth.
  • A strong local economy supported by healthcare, defense, logistics, and education sectors.
  • Investor-friendly regulations and landlord support throughout Virginia.

Best Neighborhoods in Chesapeake for Real Estate Investing

Each neighborhood below brings something valuable to the table. Here are the top five areas that stand out in Chesapeake, VA, for real estate investors.

1. Great Bridge

Great Bridge is a well-established neighborhood known for its family-friendly atmosphere and strong community ties.​

  • Neighborhood Profile: Features a mix of residential and commercial areas with access to quality schools and parks.
  • Types of Properties: Primarily single-family homes with some townhouses.
  • Typical Home Values and Rent Range: Median home value is around $501,268, with rents averaging $1,989 per month.
  • Rental Demand and Amenities: High demand due to excellent schools and proximity to shopping centers and recreational facilities.

Why Invest in Great Bridge

Great Bridge attracts long-term tenants (especially military families and professionals), making it a prime neighborhood for investors who want stability, minimal turnover, and steady cash flow.

2. Greenbrier

Greenbrier is a bustling neighborhood that combines residential comfort with commercial convenience.​

  • Neighborhood Profile: Known for its shopping centers, restaurants, and easy access to major highways.
  • Types of Properties: A mix of single-family homes, townhouses, and apartments.
  • Typical Home Values and Rent Range: The median home value is approximately $342,321, and rents range from $1,630 to $2,498, depending on unit size.
  • Rental Demand and Amenities: Strong demand from professionals and families seeking convenience and access to amenities.​

Why Invest in Greenbrier

Greenbrier is perfect for investors seeking consistent occupancy and appeal to young professionals. Its mix of affordability and amenities supports strong rent yields and year-round demand.

3. South Norfolk

South Norfolk offers a blend of historic charm and revitalization, attracting investors interested in value-add opportunities.​

  • Neighborhood Profile: Features historic homes and is undergoing revitalization efforts.
  • Types of Properties: Primarily older single-family homes with some new developments.
  • Typical Home Values and Rent Range: The median home value is around $284,248, and rents for two-bedroom units average $1,614.
  • Rental Demand and Amenities: Affordable housing options attract a diverse tenant base; proximity to downtown Norfolk adds to its appeal.​

Why Invest in South Norfolk

South Norfolk offers a lower barrier to entry and strong appreciation potential. It’s ideal for investors looking to rehab or flip homes or buy and hold in a trending upward market.

4. Western Branch

Western Branch is a suburban neighborhood known for its excellent schools and family-friendly environment.

  • Neighborhood Profile: Offers a mix of residential areas with access to shopping and dining options.
  • Types of Properties: Single-family homes, townhouses, and some apartments.
  • Typical Home Values and Rent Range: Median home price is approximately $389,700, with rents ranging from $1,412 for one-bedroom to $1,780 for three-bedroom units.
  • Rental Demand and Amenities: High demand from families due to quality schools and community amenities.​

Why Invest in Western Branch

Western Branch is a smart pick for long-term rental strategies. With low turnover and a reliable tenant base, this area is well-suited for building a portfolio of steady-income properties.

5. Hickory

Hickory is a semi-rural neighborhood offering larger properties and a quieter lifestyle, appealing to those seeking space and tranquility.​

  • Neighborhood Profile: Known for its spacious lots and rural charm.
  • Types of Properties: Primarily single-family homes on large lots.
  • Typical Home Values and Rent Range: Home prices range from $400,000 to $600,000, with rents varying based on property size and features.
  • Rental Demand and Amenities: Attracts tenants seeking larger homes and a peaceful environment; good schools add to its desirability.

Why Invest in Hickory

Hickory is ideal for investors who want high-end, low-maintenance tenants and excellent appreciation potential. The neighborhood’s quality of life draws renters willing to pay a premium for space and school access.

Top Rental Property Neighborhoods in Chesapeake Comparison

Neighborhood

Home Prices

Average Rent

Best For

Great Bridge

$475K–$525K

$1,900–$2,100

Stable SFH with low turnover

Greenbrier

$300K–$375K

$1,630–$2,500

Professionals and convenience seekers

South Norfolk

$250K–$300K

$1,400–$1,700

Entry-level investors, value-add strategy

Western Branch

$350K–$425K

$1,400–$1,800

Long-term family renters, steady growth

Hickory

$400K–$600K+

$2,400–$3,000

Premium tenants, high ROI potential

Should You Own a Rental Property in Chesapeake, VA?

Chesapeake offers something for every type of real estate investor, whether you're looking for value, cash flow, appreciation, or all three. With strong rental demand, proximity to major employers, and neighborhoods that cater to different budgets and lifestyles, this city continues to be a top pick in Coastal Virginia.

Before making a move, take the time to explore each neighborhood and align your investment strategy with the area’s strengths. That’s how you’ll set yourself up for long-term success.

Choose the Right Neighborhood for Your Investment Property with Osprey Property Management

Choosing the right neighborhood is just the beginning. Osprey Property Management offers expert insight into the Chesapeake market, from rental trends to tenant placement to full-service property management.

Whether you're buying your first rental property or expanding your portfolio, our team is here to help you make smart, informed decisions.

Contact us today to schedule a neighborhood analysis or learn how we can help you grow your rental investments with confidence.