Chestertown, located in Queen Anne's County, Maryland, is a charming and historic riverside town known for its picturesque architecture, vibrant arts community, and rich history. Nestled along the banks of the Chester River, Chestertown offers a peaceful yet engaging lifestyle, surrounded by beautiful landscapes and a welcoming community. This article explores the best residential areas in Chestertown, highlighting their features, housing options, and average prices, making it easier for prospective residents to find their perfect home.
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Historic Downtown

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Historic Downtown Chestertown is the cultural and social heart of the town, known for its cobblestone streets and historic buildings. It is ideal for those who appreciate art, history, and an active lifestyle.
Characteristics of the Historic Downtown
* Culture: Art galleries, theaters, historic sites
* Transportation: Walkable area with bike-friendly paths
* Services: Restaurants, shops, and community services
* Environment: Lively and artistic
Housing Options in the Historic Downtown
Restored historic homes, Townhouses, Apartments
Average Home Prices in the Historic Downtown
* Buying: $300,000 – $500,000
* Renting: $1,200 – $2,000/month
Chestertown Waterfront

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The Waterfront area offers beautiful views of the Chester River, making it perfect for those who enjoy boating and water activities. The ambiance is relaxing, with parks and recreational options nearby.
Characteristics of the Chestertown Waterfront
* Culture: Maritime activities, festivals
* Transportation: Easy access to marinas, walkable pathways
* Services: Waterfront parks, fishing spots, local shops
* Environment: Tranquil and scenic
Housing Options in the Chestertown Waterfront
Waterfront homes, Condominiums
Average Home Prices in the Chestertown Waterfront
* Buying: $400,000 – $700,000
* Renting: $1,800 – $2,500/month
Town Hill

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The Town Hill neighborhood is a peaceful residential area characterized by tree-lined streets and family-friendly ambiance. Ideal for families seeking a suburban feel with access to city amenities.
Characteristics of the Town Hill
* Culture: Community-centered activities
* Transportation: Car-friendly with nearby public transport
* Services: Schools, parks, grocery stores
* Environment: Quiet and friendly
Housing Options in the Town Hill
Single-family homes, Larger lots
Average Home Prices in the Town Hill
* Buying: $250,000 – $450,000
* Renting: $1,000 – $1,800/month
East Chestertown

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East Chestertown is a dynamic neighborhood with a blend of historic charm and modern amenities. It appeals to young professionals and families looking for a vibrant community.
Characteristics of the East Chestertown
* Culture: Young community, diverse dining options
* Transportation: Access to major roads, bike connections
* Services: Local markets, cafes, and retail shops
* Environment: Energetic and diverse
Housing Options in the East Chestertown
Modern homes, Townhouses
Average Home Prices in the East Chestertown
* Buying: $280,000 – $480,000
* Renting: $1,300 – $2,000/month
Kent County Locality

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Kent County is known for its spacious properties and rural setting, providing a serene lifestyle while being close to Chestertown's amenities. This area is perfect for nature lovers and those seeking space.
Characteristics of the Kent County Locality
* Culture: Nature-focused lifestyle, farms
* Transportation: Car necessary, rural roads
* Services: Limited, self-reliant living with small shops nearby
* Environment: Rural and peaceful
Housing Options in the Kent County Locality
Farmhouses, Large estates
Average Home Prices in the Kent County Locality
* Buying: $350,000 – $600,000
* Renting: $1,200 – $1,800/month
High Street District

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The High Street District features diverse housing options and is close to schools and amenities, making it a desirable area for families and young professionals.
Characteristics of the High Street District
* Culture: Community events, local eateries
* Transportation: Public transport options, bike-friendly
* Services: Schools, community centers, shops
* Environment: Family-friendly and welcoming
Housing Options in the High Street District
Single-family homes, Duplexes
Average Home Prices in the High Street District
* Buying: $275,000 – $475,000
* Renting: $1,100 – $1,700/month
Frequently Asked Questions About the Best Residential Areas in Chestertown:
The best residential areas in Chestertown include Historic Downtown, Waterfront, Town Hill, East Chestertown, Kent County, and High Street District.
Town Hill and the High Street District are highly recommended for families due to proximity to schools and parks.
Yes, areas like East Chestertown and Town Hill offer more affordable housing options suitable for different budgets.
The average home prices in Chestertown generally range from $250,000 to $500,000 depending on the neighborhood.
Rental prices for apartments in Chestertown typically range from $1,000 to $2,500/month.
Chestertown has limited public transport options; it is more car-friendly, but many areas are walkable and bike-friendly.
Chestertown hosts various cultural events, art galleries, farmers markets, and community festivals throughout the year.
Yes, Chestertown is served by quality public and private schools, making it suitable for families with children.
Residents can enjoy parks, water sports on the Chester River, hiking trails, and community events.
Chestertown is considered to be a safe and friendly community with a low crime rate, making it attractive for families and retirees.
Conclusion on the Best Residential Areas in Chestertown:
Chestertown, Maryland, presents an array of residential neighborhoods that cater to diverse lifestyles. Whether you prefer the lively Historic Downtown, the peaceful Town Hill, or the tranquil Kent County, Chestertown offers ample opportunities for residents to find their ideal home. The community's rich cultural offerings, excellent schools, and variety of outdoor activities make it an attractive place to live. With housing options that range from historic homes to modern properties, Chestertown provides a unique living experience enriched by its history and natural beauty.
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.