Living Local - May

Blake Wood
May 18
4 min read

Welcome

First off, thank you for subscribing and following along as we launch The Wood Group.

Each month, you will receive two newsletters from us. At the beginning of the month, you will receive a market update focused specifically on Anne Arundel County real estate. Rather than flooding you with national headlines and clickbait, we will break down what actually matters locally, what trends we are watching, and what buyers and sellers should realistically pay attention to.

The second is Living Local (this newsletter), a more hyper-local look at how the Annapolis lifestyle and real estate intersect. Expect neighborhood spotlights, local insight, community trends, and the kinds of details you only really notice when you spend your life around Annapolis.

What you will not receive are spammed emails, copied-and-pasted national content, or generic information that has nothing to do with the Annapolis market.

We are excited to build this alongside all of you.

Where Annapolis living and real estate intersect

Commissioning Week, an Annapolis Real Estate Cheat Code

Photo Credit: Chesapeake Bay Magazine

Commissioning Week has always marked the unofficial start of summer in Annapolis. For one week each May, the city becomes immersed with out-of-town families and one tradition after another. Hotel rooms become nearly impossible to find, while events like the Herndon climb and the arrival of the Blue Angels take over the city, two traditions dating back to the 1940s that never seem to get old.

What most people outside Annapolis do not realize is how much demand this creates for housing. Thousands of family members come into town during Commissioning Week, and hotels near downtown and the Academy are typically booked far in advance. Similar to Augusta during Masters week, many visitors end up looking to local homeowners for short-term rentals instead.

That has become even more valuable recently as Annapolis has heavily restricted new short-term rentals. One unique carveout still remains though. During major events like Commissioning Week and the spring and fall boat shows, homeowners are still allowed to legally rent their properties during these short event windows.

For many locals, it has become one of the more unique perks of living here. Some families leave town for the week, rent out their home, and use the income to offset a meaningful portion of their annual housing costs. In our case, just a few major Annapolis event weeks have covered nearly 20% of our yearly mortgage payment. Others simply use it as an excuse to take a great vacation while demand for Annapolis is at its peak.

It is one of those uniquely Annapolis dynamics where local tradition, real estate, and the rhythm of the city all intersect.

Neighborhood Spotlight

Hillsmere

Lifestyle: A laid-back waterfront community with a strong neighborhood feel where residents spend as much time outside as possible. Walking, boating, paddleboarding, beach days, and community events are a big part of daily life here.

Amenities: Features a private community beach on the South River, a marina, boat ramp, playgrounds, pool, and a very active community association with events throughout the year. Quiet Waters Park is also located directly next to the neighborhood and becomes an extension of the community for many residents.

Location: Located just south of downtown Annapolis off Forest Drive, Hillsmere offers quick access to downtown, Eastport, and Route 50 while still feeling tucked away from the busier parts of the city.

Environment: Known for its mature trees, water access, and proximity to Quiet Waters Park, Hillsmere blends a wooded neighborhood feel with easy access to the Chesapeake lifestyle. The community beach and South River views give parts of the neighborhood a true coastal feel despite being only minutes from downtown Annapolis.

Real Estate: Hillsmere has averaged roughly 54 home sales per year over the last five years, with a wide range of values from $225,000 to $2.7M. While the median sales price over the last five years sits around $600,000, the median price over the last 12 months has climbed to $700,000 as demand for the neighborhood continues to grow.

Most homes were originally built in the 1960s and average around 1,700 square feet with 4 bedrooms, 3 bathrooms, and lot sizes near one-third of an acre. Architectural styles vary throughout the neighborhood, though original split foyers and ranchers make up a large portion of the housing stock alongside colonials, contemporary homes, and newer renovations.

The market here has been especially competitive recently, with median days on market sitting at just 8 days. Over the last year, Hillsmere has appreciated at roughly 10% annually, significantly outpacing Anne Arundel County as a whole. Even over a full five-year period, the neighborhood has averaged approximately 7.5% annual appreciation, making it one of the stronger-performing waterfront-adjacent communities in the Annapolis area.

Thank you for reading and supporting The Wood Group.

If you or someone you know is thinking about buying or selling in the Annapolis area, we would love the opportunity to help.

Blake Wood

Blake@thewoodgroupre.com

(410) 507-9854