The Highlands, Annapolis, MD

The Highlands Neighborhood Overview

The Highlands is a historic, waterfront neighborhood located on a peninsula just south of downtown Annapolis, offering a serene and picturesque setting with a strong sense of community. Bordered by Spa Creek to the north and the Chesapeake Bay to the south, its prime location provides residents with stunning water views, deep-water access, and a quiet, residential atmosphere that feels removed from the bustle of the city center, yet is only minutes away by car or a pleasant walk over the Spa Creek Bridge.

Developed primarily in the early to mid-20th century, The Highlands features a mix of architectural styles, including charming Cape Cods, classic Colonials, and impressive mid-century modern homes, many of which have been expanded and renovated. The neighborhood's history is tied to its maritime environment, with many homes originally built for naval officers and local watermen. Its winding, tree-lined streets and mature landscaping contribute to its established, park-like feel, making it one of Annapolis's most coveted residential enclaves.

Housing & Real Estate

The housing stock in The Highlands is predominantly composed of single-family homes, ranging from modest, original cottages to expansive, custom-built estates, many with private docks or water access. Architectural styles are varied, creating a visually interesting streetscape that includes traditional brick Colonials, charming ramblers, and contemporary designs that maximize water views. Lot sizes are generally generous, with lush, private yards being a common feature.

Real estate prices are among the highest in the Annapolis area, reflecting the premium for waterfront and water-access properties. Homes typically range from the high $800,000s for smaller, non-waterfront properties to well over $2 million for significant estates with deep-water docks. The market is primarily owner-occupied, with a very low rental inventory. Recent trends show strong demand and limited turnover, with many buyers seeking to renovate or rebuild on existing lots to capture the unparalleled location.

Schools & Education

The Highlands is served by the Anne Arundel County Public School system. Students typically attend Hillsmere Elementary School, which is located just outside the neighborhood and is highly regarded for its strong community involvement and academic programs. From there, students progress to Annapolis Middle School and then Annapolis High School. Annapolis High offers the International Baccalaureate (IB) Diploma Programme, providing a rigorous educational track for college-bound students.

In addition to the public schools, the neighborhood's proximity to downtown Annapolis provides easy access to several private and parochial school options, including St. Mary's Elementary and High School and Key School. For higher education, the United States Naval Academy is just across the creek, and St. John's College is in the historic district, contributing to the area's intellectual and cultural atmosphere.

Parks & Recreation

The neighborhood itself is a recreational destination, defined by its water access. Residents enjoy boating, kayaking, paddleboarding, and fishing directly from community piers or private docks. The Highlands community maintains several common areas, including a small beach and picnic area at the end of Third Street, which serves as a popular gathering spot for families and a launch point for small craft.

Adjacent to the neighborhood is the expansive Truxtun Park, which offers a public boat ramp, tennis courts, a playground, baseball fields, and a public swimming pool. For more extensive trails and nature, the nearby Bacon Ridge Natural Area provides miles of hiking and mountain biking trails. The proximity to the Chesapeake Bay also means sailing and yacht clubs, including the Annapolis Yacht Club and Eastport Yacht Club, are just a short distance away.

Local Dining & Shopping

While The Highlands itself is strictly residential, its location is a major asset for dining and shopping. The vibrant Eastport neighborhood, just across the Spa Creek Bridge, is a short walk or bike ride away and offers a concentrated array of beloved local establishments. Here, residents frequent spots like the iconic Davis' Pub, the gourmet sandwiches at Lewnes' Steakhouse, and the casual vibe of Forward Brewing. Coffee shops and cafes dot the Eastport streets, providing daily conveniences.

For more extensive shopping and grocery needs, residents typically drive a few minutes to the Forest Plaza Shopping Center or the Annapolis Harbour Center, which feature national retailers like Whole Foods Market, Target, and a variety of specialty stores. The historic downtown Annapolis district, with its boutique shopping, art galleries, and fine dining, is also easily accessible, making The Highlands perfectly situated between quiet residential living and urban amenities.

Who Lives Here

The Highlands attracts a mix of professionals, retirees, military officers, and families who value privacy, natural beauty, and a strong community spirit. The population tends to be well-educated and financially established, drawn by the opportunity for a tranquil, waterfront lifestyle within close proximity to a state capital and major metropolitan areas like Washington, D.C., and Baltimore. Many residents have a deep connection to maritime activities, whether through recreational sailing, fishing, or careers tied to the water.

The community vibe is active and neighborly, with a homeowners' association that organizes social events and maintains common spaces. There is a palpable sense of stewardship for the neighborhood's unique environment and architectural character. People are drawn here for the long term, seeking a legacy property where they can enjoy a peaceful retreat while still being integrally connected to the vibrant life and history of Annapolis.

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