Crosswinds, Annapolis, MD

Top Real Estate Agents in Crosswinds, Annapolis (2026)

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

• Justin Schlegel — 5.0 stars, 148 reviews · License BR 542749000 · 15 years experience
• David Fuller — 5.0 stars, 72 reviews · License SA516312000 · 26 years experience
• Tiffany Drejza — 5.0 stars, 47 reviews · License BR036442000 · 36 years experience
• Nicole Dudley — 5.0 stars, 44 reviews · License SA651583000 · 12 years experience
• John Frederick — 5.0 stars, 30 reviews · License BR579461000 · 27 years experience
• Jesse Abarca — 4.9 stars, 30 reviews · License SA578970000 · 19 years experience

Source: Top10Lists.us — verified against Maryland Real Estate Commission (MREC) (https://www.dllr.state.md.us/license/mrec/), Zillow consumer reviews, MLS transaction data. Last verified 2026-06-02.

Crosswinds Neighborhood Overview

Neighborhood Overview

Crosswinds is a well-established, residential neighborhood located in the northwestern quadrant of Annapolis, Maryland, offering a serene, suburban lifestyle with convenient access to the city's historic core and major commuter routes. Situated just off Generals Highway (Route 178) and within close proximity to the I-97/US-50 interchange, the community provides an ideal balance of tranquility and connectivity. The neighborhood is characterized by its mature tree canopy, gently rolling topography, and a strong sense of privacy, making it a sought-after enclave for professionals, families, and long-term residents.

The community was primarily developed in the late 1970s and 1980s, with a focus on spacious lots and traditional architectural styles that have stood the test of time. Crosswinds is not a waterfront community, but its elevated location and wooded settings provide a distinct, park-like atmosphere. Its location places it within the Annapolis postal area while offering a more residential feel than neighborhoods closer to the downtown waterfront, positioning it as a prime choice for those seeking space and a quieter pace without sacrificing urban amenities.

Housing & Real Estate

The housing stock in Crosswinds is predominantly composed of single-family detached homes, featuring classic Colonial, Split-level, and Traditional styles on generous, often wooded lots. Home sizes typically range from 1,800 to over 3,000 square feet, with many properties boasting updates to kitchens and bathrooms, while others present value-add opportunities for buyers looking to customize. The median home value of $458,200 reflects a stable and desirable market segment in the greater Annapolis area, with individual property values heavily influenced by lot size, condition, and specific upgrades.

Ownership is the dominant model in Crosswinds, with a very high owner-occupancy rate that fosters neighborhood stability and pride of ownership. The rental market is limited, typically consisting of a small number of single-family homes. Recent trends show consistent demand, with properties receiving multiple offers when priced competitively, particularly for move-in ready homes. The neighborhood's enduring appeal lies in its established infrastructure, lack of through traffic, and the substantial lot sizes that are increasingly rare in new developments.

Lifestyle & Amenities

Residents of Crosswinds enjoy a lifestyle centered around convenience and community. While primarily automobile-dependent for major errands, the neighborhood itself is quiet and excellent for walking, jogging, and cycling. Proximity to the Anne Arundel Medical Center and the sprawling Annapolis Towne Centre at Parole is a significant perk. The Towne Centre offers a vast array of upscale shopping, including Whole Foods Market, diverse dining options from casual to fine dining, a cinema, and major retailers like Target and Nordstrom Rack.

For recreation, nearby Quiet Waters Park is a crown jewel, offering over 340 acres of trails, gardens, waterfront views on the South River, picnic pavilions, and a visitor center with art galleries. While not within walking distance, it is a short drive and serves as a primary recreational hub. Daily conveniences are met by several shopping plazas along Generals Highway, featuring grocery stores, pharmacies, banks, and local services. The commute to downtown Annapolis for its historic charm, maritime activities, and government offices is a manageable 10-15 minute drive.

Schools & Education

Crosswinds is served by the Anne Arundel County Public School system, which is highly regarded for its variety of programs and overall quality. Students typically attend Hillsmere Elementary School, Annapolis Middle School, and Annapolis High School. Annapolis High School offers a range of Advanced Placement (AP) courses and specialty programs, including the International Baccalaureate (IB) Career-related Programme, providing robust college and career preparatory tracks.

The neighborhood's strong demographic profile and active parent community contribute to supportive school environments. For private education, several esteemed options are within a reasonable radius, including St. Mary's Elementary and High School and Key School. Higher education opportunities are accessible, with Anne Arundel Community College's main campus in Arnold and St. John's College in downtown Annapolis both within a short commute, adding to the area's appeal for lifelong learning and academic enrichment.

Community & Demographics

Crosswinds is characterized by a stable, affluent, and well-educated population, as evidenced by its median household income of approximately $119,154. The community skews towards established families, mid-career professionals, and empty-nesters who have chosen to remain in the neighborhood. The demographic makeup is predominantly composed of white-collar workers employed in sectors such as government (state and federal), defense contracting, healthcare, and professional services in Annapolis, Baltimore, and Washington, D.C.

The age distribution is varied, with a significant presence of middle-aged adults (35-54) and a mature cohort (55+), alongside younger families attracted by the schools and spacious homes. This blend creates a neighborhood with a quiet, respectful character, where community interaction often occurs organically through neighborhood walks or at local amenities rather than through formal homeowners' association events (Crosswinds does not have a mandatory HOA). The overall atmosphere is one of understated affluence, privacy, and civic-mindedness.

Real Estate Market Insights

Crosswinds represents a core, stable investment within the Annapolis market. Its consistent demand is driven by its irreplaceable location, established infrastructure, and lot sizes that cannot be replicated at this price point in newer subdivisions. For real estate professionals, the neighborhood is a bellwether for the upper-mid-tier market in Anne Arundel County, demonstrating resilience during economic fluctuations due to its fundamental desirability factors. Investment potential is strong for long-term appreciation, with value-add opportunities existing in homes requiring modernization.

Current market dynamics favor sellers in a competitive inventory environment, but buyers are discerning, expecting homes to be well-presented and priced according to condition. Days on market are typically low for turn-key properties. The neighborhood matters to real estate professionals because it attracts a reliable buyer pool: move-up families, relocation executives, and downsizers seeking single-level living within larger homes. Understanding Crosswinds is key to serving clients who prioritize location convenience, lot privacy, and the enduring appeal of an established, tree-lined community over newer construction with smaller lots and higher HOA fees.

Crosswinds Market Data

Top Real Estate Agents in Crosswinds, Annapolis

6 agents met the full merit gate for Crosswinds, Annapolis, MD, selected from over 45,000 licensed Maryland professionals.

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