Princess Anne, located in Somerset County, Maryland, embodies the charm of small-town living while being close to the coast. This picturesque town is home to a thriving educational community, rich history, and beautiful natural surroundings. Residents enjoy a slower pace of life surrounded by nature, with access to amenities and services. This article highlights the best residential areas in Princess Anne, offering insights into their characteristics, housing options, and average prices.
Table of Contents
Downtown Princess Anne

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The heart of Princess Anne, Downtown offers a blend of historic buildings and modern conveniences. It's ideal for those who appreciate community events and easy access to local businesses.
Characteristics of the Downtown Princess Anne
* Culture: Local arts and crafts, historic architecture
* Transportation: Public transportation available, walkable
* Services: Shops, cafes, restaurants, post office
* Environment: Vibrant and community-oriented
Housing Options in the Downtown Princess Anne
Historic homes, townhouses, apartments
Average Home Prices in the Downtown Princess Anne
* Buying: $150,000 – $250,000
* Renting: $1,200 – $1,600/month
UMES Community

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Adjacent to the University of Maryland Eastern Shore (UMES), this community is heavily influenced by the presence of students and faculty. It's perfect for those who want a lively environment with educational resources.
Characteristics of the UMES Community
* Culture: Educational and cultural activities at UMES
* Transportation: Bicycle-friendly, bus services available
* Services: University amenities, cafes, student centers
* Environment: Energetic and youthful
Housing Options in the UMES Community
Multi-family homes, student housing, single-family homes
Average Home Prices in the UMES Community
* Buying: $130,000 – $220,000
* Renting: $900 – $1,400/month
Old Princess Anne

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This area boasts some of the oldest homes in the region, reflecting the rich history of Princess Anne. It’s perfect for history enthusiasts and those seeking charming architecture.
Characteristics of the Old Princess Anne
* Culture: Historical significance, preservation efforts
* Transportation: Limited public transport, walking distance to amenities
* Services: Local restaurants, historical sites, parks
* Environment: Quiet and nostalgic
Housing Options in the Old Princess Anne
Victorian homes, single-family houses
Average Home Prices in the Old Princess Anne
* Buying: $180,000 – $300,000
* Renting: $1,000 – $1,500/month
Parson’s Mill

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Located slightly outside of the main town, Parson’s Mill offers a more rural setting. It’s perfect for families and those looking for larger lots with more room.
Characteristics of the Parson’s Mill
* Culture: Family-friendly, community-oriented
* Transportation: Car necessary, proximity to main roads
* Services: Grocery store, recreational areas, schools
* Environment: Spacious and peaceful
Housing Options in the Parson’s Mill
Single-family homes, larger property lots
Average Home Prices in the Parson’s Mill
* Buying: $200,000 – $350,000
* Renting: $1,300 – $1,800/month
Smith Island

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A unique community accessible by boat, Smith Island offers an unparalleled waterfront living experience. It’s perfect for those who cherish maritime life and a close-knit community.
Characteristics of the Smith Island
* Culture: Fishing and maritime lifestyle
* Transportation: Ferry service only, minimal traffic
* Services: Local markets, fishing facilities, community events
* Environment: Quiet and close-knit
Housing Options in the Smith Island
Waterfront homes, cottages
Average Home Prices in the Smith Island
* Buying: $150,000 – $300,000
* Renting: $1,000 – $1,500/month
Sandy Point

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This area is known for its beautiful waterfront properties and recreational opportunities. It is a favorite for those who enjoy boating, fishing, and beach activities.
Characteristics of the Sandy Point
* Culture: Water sports and outdoor activities
* Transportation: Car recommended, scenic routes
* Services: Marinas, parks, picnic areas
* Environment: Relaxed and recreational
Housing Options in the Sandy Point
Beach houses, modern single-family homes
Average Home Prices in the Sandy Point
* Buying: $250,000 – $400,000
* Renting: $1,800 – $2,500/month
Frequently Asked Questions About the Best Residential Areas in Princess Anne:
The best residential areas in Princess Anne include Downtown Princess Anne, UMES Community, Old Princess Anne, Parson’s Mill, Smith Island, and Sandy Point.
Parson’s Mill is highly recommended for families due to its spacious housing and proximity to schools.
The UMES Community tends to have more affordable housing options, especially for students and young professionals.
Downtown Princess Anne offers the most amenities, including shops, cafes, and community centers.
Yes, each area, especially Downtown and the UMES Community, has active neighborhood events that foster community engagement.
The average cost of living can vary, with housing prices generally ranging from $130,000 to $400,000 depending on the area.
Yes, Princess Anne is served by a number of well-rated public schools, and proximity to UMES adds educational value.
Residents can enjoy boating, fishing, hiking, and community events throughout the year, particularly in Sandy Point and Parson’s Mill.
Public transportation is limited; thus, owning a car is recommended for getting around.
Smith Island offers the most tranquility with its remote, close-knit community and scenic waterfront.
Conclusion on the Best Residential Areas in Princess Anne:
Princess Anne, MD, presents a variety of residential options suitable for many lifestyles, from families to students to retirees. Whether you prefer the hustle and bustle of Downtown, the educational vibe near UMES, or the serene nature of Smith Island, there is something for everyone in this charming town. Its unique blend of culture, community, and natural beauty makes Princess Anne a truly inviting place to call home.
About the Author

Published by:Eribert De Oliveira
Mechatronics Engineer and founder of Mi Inmueble Online, with a background in real estate. I combine technology and analysis to help you find the best areas to live.