Henderson, a quaint town in Caroline County, Maryland, offers a charming and peaceful environment perfect for families and individuals alike. Known for its rich agricultural heritage, friendly community, and beautiful landscapes, Henderson combines small-town charm with convenience. Our guide explores the best residential areas of Henderson, detailing their unique characteristics, housing options, and average prices.
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Downtown Henderson

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Downtown Henderson serves as the center of the town's activities, showcasing local businesses, eateries, and a welcoming community. It's perfect for those who enjoy a vibrant lifestyle close to amenities.
Characteristics of the Downtown Henderson
* Culture: Strong sense of community, local events, and festivals
* Transportation: Primarily car-dependent with limited public transport options
* Services: Grocery stores, cafes, shops, and post office
* Environment: Friendly and lively with a hometown feel
Housing Options in the Downtown Henderson
Single-family homes, Townhouses
Average Home Prices in the Downtown Henderson
* Buying: $210,000 – $350,000
* Renting: $1,200 – $1,800/month
Henderson Point

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Henderson Point offers a scenic waterfront living experience characterized by access to beautiful views and outdoor recreation. Ideal for families and outdoor enthusiasts.
Characteristics of the Henderson Point
* Culture: Nature-focused, family-friendly activities around the water
* Transportation: Car essential; walking paths along the waterfront
* Services: Cafes, parks, and recreational areas
* Environment: Quiet, peaceful, and inviting
Housing Options in the Henderson Point
Waterfront homes, Bungalows, and Villas
Average Home Prices in the Henderson Point
* Buying: $250,000 – $400,000
* Renting: $1,500 – $2,200/month
Country Estates

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Country Estates offers spacious living amidst a backdrop of farmland and natural beauty. It's ideal for those who seek a blend of countryside tranquility and suburban amenities.
Characteristics of the Country Estates
* Culture: Agricultural community with local farmers' markets
* Transportation: Car required; rural roads
* Services: Local shops, utility services, and farm stands
* Environment: Serene and spacious
Housing Options in the Country Estates
Large single-family homes, Ranch-style houses
Average Home Prices in the Country Estates
* Buying: $300,000 – $450,000
* Renting: $1,800 – $2,500/month
Pine Hollow

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Pine Hollow is known for its family-friendly environment, excellent schools, and tight-knit community. A great area for families looking for a safe and nurturing place to live.
Characteristics of the Pine Hollow
* Culture: Community-oriented with strong educational support
* Transportation: Transit connections within the county, car recommended
* Services: Parks, schools, and recreational facilities
* Environment: Safe, family-centric, and welcoming
Housing Options in the Pine Hollow
Single-family homes, Duplexes
Average Home Prices in the Pine Hollow
* Buying: $275,000 – $400,000
* Renting: $1,400 – $2,100/month
East Henderson

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East Henderson features a mix of modern conveniences and established neighborhoods. It is perfect for those who enjoy a suburban lifestyle while being close to urban amenities.
Characteristics of the East Henderson
* Culture: Diverse community, supportive local groups
* Transportation: Good road access, limited public transport
* Services: Shopping centers, dining options, and services
* Environment: Busy, connected, and vibrant
Housing Options in the East Henderson
Townhomes, Condos, Single-family homes
Average Home Prices in the East Henderson
* Buying: $220,000 – $370,000
* Renting: $1,100 – $1,700/month
West Shore Estates

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West Shore Estates is perfect for those looking for a semi-rural lifestyle close to the water. The homes are modern and spacious, set in a tranquil environment.
Characteristics of the West Shore Estates
* Culture: Peaceful living with strong outdoor activities, boating culture
* Transportation: Car required; close proximity to main roads
* Services: Basic amenities, recreational parks, and waterfront access
* Environment: Relaxed and harmonious
Housing Options in the West Shore Estates
Single-family homes, Custom-built homes
Average Home Prices in the West Shore Estates
* Buying: $280,000 – $420,000
* Renting: $1,600 – $2,300/month
Frequently Asked Questions About the Best Residential Areas in Henderson:
The best neighborhoods in Henderson include Downtown Henderson, Henderson Point, Country Estates, Pine Hollow, East Henderson, and West Shore Estates.
Pine Hollow is known for being particularly family-friendly, with great schools and a supportive community.
Henderson Point and West Shore Estates offer excellent waterfront living options.
East Henderson boasts several shopping centers, dining options, and local services.
Home prices in Henderson generally range from $210,000 to $450,000, depending on the area and property type.
Pine Hollow and Henderson Point have excellent parks and recreational areas for families and outdoor enthusiasts.
Most neighborhoods are car-dependent with some limited public transport options within the county.
Yes, Henderson offers a peaceful environment, scenic views, and a friendly community which is attractive for retirees.
Pine Hollow is highly recommended for new families due to its excellent schools and community atmosphere.
Yes, Downtown Henderson and parts of Pine Hollow provide more affordable housing options in the area.
Conclusion on the Best Residential Areas in Henderson:
Henderson, MD offers a variety of charming residential areas suitable for families, retirees, and individuals seeking a peaceful lifestyle. From the vibrant community feel of Downtown Henderson to the waterfront tranquility of Henderson Point, each neighborhood presents unique advantages. With its rich agricultural heritage and friendly locals, Henderson is a wonderful place to call home. Choosing the right residential area will depend on your lifestyle preferences—be it community engagement, outdoor activities, or access to amenities. Overall, Henderson is a hidden gem in Caroline County, providing a fulfilling and enriching living experience.
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.