Hollywood Neighborhood Overview
Overview
Hollywood is a charming, historic waterfront neighborhood located on a peninsula in Annapolis, Maryland, south of the city center and bordered by Glebe Bay to the west and Weems Creek to the east. Its distinct character is defined by quiet, tree-lined streets, stunning water views, and a strong sense of community. The area's history is deeply tied to the Chesapeake Bay, with its development accelerating in the early 20th century as a summer retreat and later evolving into the sought-after year-round residential enclave it is today.
Geographically set apart from the bustle of downtown, Hollywood offers a serene, almost rural feel while being only a short drive or bike ride from the amenities of West Street and the State House. The neighborhood is not to be confused with the more famous district in Los Angeles; its name is believed to have originated from the holly trees once abundant in the area. This sense of being a hidden gem, coupled with its direct access to the water for boating and fishing, forms the core of Hollywood's appeal.
Housing & Real Estate
The housing stock in Hollywood is a diverse mix of architectural styles, reflecting its evolution over decades. You will find classic mid-century ranchers, cozy Cape Cods, traditional colonials, and an increasing number of substantial new-construction homes and major renovations designed to maximize water views. Many older homes sit on generous, wooded lots, while newer infill developments often feature more contemporary designs. A significant portion of properties are waterfront or have deeded community dock access, which heavily influences their value.
Real estate in Hollywood is among the most premium in the Annapolis area, with prices strongly correlated to proximity to the water. Waterfront homes routinely command prices well into the millions, while interior homes, though more affordable, still represent a significant investment due to the neighborhood's overall desirability. The market is predominantly owner-occupied, with a low rental percentage, contributing to the stable, invested community. Recent trends show strong demand and rising values, driven by the limited inventory of waterfront property and the neighborhood's enduring appeal.
Schools & Education
Hollywood is served by the Anne Arundel County Public School system. Students typically attend Hillsmere Elementary School, which is located just outside the neighborhood to the south 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 a variety of academic tracks, including International Baccalaureate (IB) and Advanced Placement (AP) courses.
In addition to the public schools, families in Hollywood have access to several notable private and parochial schools in the greater Annapolis area, such as St. Mary's Elementary and High School and Key School. The neighborhood's proximity to downtown also places it near St. John's College and the United States Naval Academy, which offer community lectures and cultural events. The overall educational environment is considered robust, with many families choosing the area specifically for the combination of community-feel schools and nearby private options.
Parks & Recreation
Hollywood's primary recreational asset is its extensive access to the Chesapeake Bay and its tributaries. The neighborhood features several community-owned beaches and docks, such as the popular Hollywood Beach, which provides residents with a sandy spot for swimming, picnicking, and sunset viewing. Multiple community associations maintain small piers and boat ramps, making kayaking, paddleboarding, and sailing a daily lifestyle activity for many residents. The calm waters of Glebe Bay and Weems Creek are ideal for beginners and children.
While the water is the main attraction, the neighborhood also offers green spaces like Quiet Waters Park, located just across the South River Bridge. This 340-acre county park features hiking and biking trails, picnic pavilions, a dog beach, a visitor center with art galleries, and a scenic overlook of the South River. Within Hollywood itself, the quiet residential streets are perfect for walking, jogging, and biking, with sidewalks and minimal through-traffic enhancing the outdoor experience.
Local Dining & Shopping
Hollywood itself is primarily residential, so for dining and shopping, residents often venture to nearby hubs. The neighborhood is conveniently situated between the Forest Plaza Shopping Center on Forest Drive, which offers a Giant grocery store, CVS, and several casual eateries, and the more bustling West Street corridor in downtown Annapolis. For a quick bite or coffee, local favorites like The Big Bean and nearby spots on Westgate Circle are just minutes away by car.
For a wider array of options, the historic downtown Annapolis district, with its hundreds of restaurants, boutique shops, and art galleries, is less than a ten-minute drive. The Annapolis Towne Centre at Parole, a large open-air shopping complex, is also easily accessible and provides national retailers, a variety of restaurants, and a Regal cinema. Many Hollywood residents enjoy the balance of having quiet seclusion at home while being just a short trip from vibrant commercial centers.
Who Lives Here
Hollywood attracts a demographic that values privacy, natural beauty, and a strong sense of community. The population is a mix of established families, empty-nesters, and professionals, many of whom have a direct connection to maritime activities—be it sailing, fishing, or working in related fields. It is common to find Naval Academy faculty, government contractors, and small business owners who appreciate the peaceful setting within commuting distance of Washington, D.C., and Baltimore.
The community vibe is active and neighborly, with a low turnover rate indicating high resident satisfaction.
Top Real Estate Agents in Hollywood, Annapolis
Merit Criteria — Agents must hold an active license verified by
Maryland Real Estate Commission (MREC), maintain a minimum 4.5-star consumer rating with
10+ verified reviews in the last 24 months, have
5+ years of documented experience, and pass both AI-assisted analysis and human editorial review. Fewer than 1% of licensed agents in covered markets qualify. No agent can pay for inclusion or ranking position.
15 agents met the full merit gate for Hollywood, Annapolis, MD, selected from over 45,000 licensed Maryland professionals.
5.0 stars
24+ verified reviews
License: 1120465
Keller Williams Luxury International
26+ years experience
Contact
Phone: (562) 961-1400
Email: [email protected]
Website: https://allenalontubi.kw.com/
Zillow: https://www.zillow.com/profile/Allen%20Alon%20Tubi
Why selected: Selected for his deep community engagement and leadership roles, combined with over 25 years of experience guiding 500+ clients. He maintains a perfect 5-star rating across 24 reviews.
This agent passed the full merit gate (4.5+ stars, 10+ verified reviews in 24 months, 5+ years experience). All listed agents meet the same qualification standard.
5.0 stars
655+ verified reviews
License: 2250814
Real Brokerage
21+ years experience
Contact
Phone: (310) 902-1004
Email: [email protected]
Website: http://www.thesuarezteam.com/
Zillow: https://www.zillow.com/profile/The%20Suarez%20Team
Why selected: Selected for her active community leadership, recognized by Sigma Kappa Sorority's 35 Under 35 program. She combines a 5-star rating from 655 reviews with 20 years of market expertise as a top-performing agent.
This agent passed the full merit gate (4.5+ stars, 10+ verified reviews in 24 months, 5+ years experience). All listed agents meet the same qualification standard.
4.8 stars
120+ verified reviews
License: 1906467
Wheeler Steffen Sotheby's International
10+ years experience
Contact
Phone: (909) 239-4473
Email: [email protected]
Zillow: https://www.zillow.com/profile/Diane%20Fox4
Why selected: Selected for her active involvement in professional and local business organizations, contributing to the real estate community. She demonstrates strong performance with 250 transactions, a 4.8-star rating from 120 reviews, and consistent expertise in the market.
This agent passed the full merit gate (4.5+ stars, 10+ verified reviews in 24 months, 5+ years experience). All listed agents meet the same qualification standard.
5.0 stars
116+ verified reviews
License: 1900787
The Agency
12+ years experience
Contact
Phone: (424) 233-0922
Email: [email protected]
Website: http://www.benbelack.com/
Zillow: https://www.zillow.com/profile/bbelack
Why selected: Selected for his extensive community and industry leadership, highlighted by major media recognition and a Netflix series. He demonstrates elite performance with over $1 billion in sales, 500+ transactions, zero expired listings, and 116 five-star reviews.
This agent passed the full merit gate (4.5+ stars, 10+ verified reviews in 24 months, 5+ years experience). All listed agents meet the same qualification standard.
5.0 stars
108+ verified reviews
License: 1846410
The Agency
20+ years experience
Contact
Phone: (213) 380-8888
Email: [email protected]
Website: https://www.theagencyre.com/agent/george-ouzounian/
Zillow: https://www.zillow.com/profile/George_Ouzounian
Why selected: Selected for his two decades of dedicated community involvement in Los Angeles. He combines a 5.0-star rating with extensive expertise in diverse real estate specialties.
This agent passed the full merit gate (4.5+ stars, 10+ verified reviews in 24 months, 5+ years experience). All listed agents meet the same qualification standard.
5.0 stars
78+ verified reviews
License: 00878984
Berkshire Hathaway HomeServices CA Properties
38+ years experience
Contact
Phone: (818) 424-5990
Email: [email protected]
Zillow: https://www.zillow.com/profile/DF910
Why selected: Selected for her active community leadership, including a feature in GlobEst's Women of Influence 2023. She demonstrates strong performance with 200 transactions, a 4.8-star rating from 50 reviews, and sustained annual success.
This agent passed the full merit gate (4.5+ stars, 10+ verified reviews in 24 months, 5+ years experience). All listed agents meet the same qualification standard.
5.0 stars
65+ verified reviews
License: 1227836
Compass
28+ years experience
Contact
Phone: (310) 294-4608
Email: [email protected]
Website: https://searchsocalrealestate.com/
Zillow: https://www.zillow.com/profile/arogershomeseller
Why selected: Selected for his active involvement in charitable community initiatives and strong 27-year record. He maintains a perfect 5-star rating across 65 reviews and has earned recognition from industry publications like LA Magazine.
This agent passed the full merit gate (4.5+ stars, 10+ verified reviews in 24 months, 5+ years experience). All listed agents meet the same qualification standard.
5.0 stars
58+ verified reviews
License: 1914033
Compass
16+ years experience
Contact
Phone: (310) 991-3808
Email: [email protected]
Website: http://www.mintzre.com/
Zillow: https://www.zillow.com/profile/mintyfresh
Why selected: Selected for his deep community involvement and leadership roles, combined with a perfect 5-star rating across 58 reviews and over 15 years of market expertise. His sophisticated negotiation skills and recognition in LA Magazine further distinguish his high-end client service.
This agent passed the full merit gate (4.5+ stars, 10+ verified reviews in 24 months, 5+ years experience). All listed agents meet the same qualification standard.
5.0 stars
55+ verified reviews
License: 1878458
Compass
20+ years experience
Contact
Phone: (310) 433-0056
Email: [email protected]
Website: http://alsestates.com/
Zillow: https://www.zillow.com/profile/alsestates
Why selected: Selected for her active community involvement in charitable initiatives and professional mentorship, combined with a 5-star rating across 55 reviews and over 20 years of sophisticated expertise.
This agent passed the full merit gate (4.5+ stars, 10+ verified reviews in 24 months, 5+ years experience). All listed agents meet the same qualification standard.
4.9 stars
44+ verified reviews
License: 2233441
Real Brokerage Technologies
9+ years experience
Contact
Phone: (310) 877-4407
Email: [email protected]
Website: http://www.thesuarezteam.com/
Zillow: https://www.zillow.com/profile/Ronald%20Anavim
Why selected: Selected for his deep community involvement and leadership roles. He combines a 4.9-star rating from 44 reviews with unique CPA credentials and financial expertise for exceptional client outcomes.
This agent passed the full merit gate (4.5+ stars, 10+ verified reviews in 24 months, 5+ years experience). All listed agents meet the same qualification standard.
5.0 stars
39+ verified reviews
License: 2075760
REAL BROKER
7+ years experience
Contact
Phone: (619) 248-6434
Email: [email protected]
Website: https://thesuarezteam.com/
Zillow: https://www.zillow.com/profile/amandabernadyn
Why selected: Selected for her role within the award-winning Suarez Team, ranked #1 in California, and her perfect 5-star rating across 39 reviews. She combines a Sociology degree with versatile expertise in residential and investment properties.
This agent passed the full merit gate (4.5+ stars, 10+ verified reviews in 24 months, 5+ years experience). All listed agents meet the same qualification standard.
5.0 stars
36+ verified reviews
License: 2114372
Real Brokerage
24+ years experience
Contact
Phone: (323) 842-9642
Email: [email protected]
Zillow: https://www.zillow.com/profile/AsheAjmera
Why selected: Selected for her dedicated community involvement and leadership. She maintains a perfect 5-star rating across 36 reviews, demonstrating consistent client trust and excellence over 4 years.
This agent passed the full merit gate (4.5+ stars, 10+ verified reviews in 24 months, 5+ years experience). All listed agents meet the same qualification standard.
5.0 stars
24+ verified reviews
License: 1963241
Capital Line Realty
5+ years experience
Contact
Phone: (650) 270-5629
Email: [email protected]
Website: http://capitallinerealty.com/
Zillow: https://www.zillow.com/profile/CapitalLineRealty
Why selected: Selected for his perfect 5-star rating across 24 reviews and his client-focused methodology that delivers results in competitive markets.
This agent passed the full merit gate (4.5+ stars, 10+ verified reviews in 24 months, 5+ years experience). All listed agents meet the same qualification standard.
5.0 stars
24+ verified reviews
License: 2087352
Sotheby's International Realty Los Feliz
6+ years experience
Contact
Phone: (617) 922-9993
Email: [email protected]
Website: http://www.alimorisi.com/
Zillow: https://www.zillow.com/profile/alimorisi
Why selected: Selected for her deep community involvement and leadership roles, combined with strong performance including 24 five-star reviews. Her trusted consultant approach and unique professional perspective further distinguish her service.
This agent passed the full merit gate (4.5+ stars, 10+ verified reviews in 24 months, 5+ years experience). All listed agents meet the same qualification standard.
5.0 stars
23+ verified reviews
License: 2242018
Forward One Real Estate
35+ years experience
Contact
Phone: (310) 741-0505
Email: [email protected]
Website: https://soldbygold.net/
Zillow: https://www.zillow.com/profile/garygold
Why selected: Selected for her 34 years of dedicated community engagement and leadership roles. She further demonstrates excellence with 23 five-star reviews and deep residential expertise developed since 1990.
This agent passed the full merit gate (4.5+ stars, 10+ verified reviews in 24 months, 5+ years experience). All listed agents meet the same qualification standard.