
CHESTER
Bentons Pleasure
Bentons Pleasure is a well-established residential community located in Chester, Maryland, on Kent Island. This neighborhood is known for its spacious single-family homes, many of which are situated on large lots that provide residents with privacy and a serene living environment. Architectural styles in Bentons Pleasure vary, with homes often featuring Colonial and contemporary designs that blend seamlessly with the natural surroundings.
The community's proximity to Cox Creek offers residents picturesque water views and opportunities for various water-related activities. While specific community amenities such as marinas, basketball courts, or tot lots are not highlighted in the available information, the generous property sizes and natural landscapes provide ample space for outdoor recreation and leisure.
Bentons Pleasure's location in Chester provides convenient access to local shopping centers, dining options, and recreational facilities. The community is also served by reputable schools within the Queen Anne's County Public School System, making it an appealing choice for families seeking quality education for their children. Additionally, its location offers easy access to major highways, facilitating commutes to nearby cities such as Annapolis and Baltimore.
With its combination of spacious homes, natural beauty, and community spirit, Bentons Pleasure offers a desirable living environment for those seeking a balanced lifestyle in Chester, Maryland.
By The Numbers
DATA BASED ON INFORMATION SINCE JAN 1 2020 to jan 1 2025
AVERAGE SALES PRICE
AVERAGE NUMBER OF ANNUAL SALES
AVERAGE LIST TO SALES PRICE RATIO
AVERAGE DAYS ON MARKET
AVERAGE PRICE PER SQUARE FOOT
AVERAGE BEDROOMS
AVERAGE BATHROOMS
$623,950- $1,355,000
5.5
97.2 %
57
$291.57
4
3
Highlights
lifestyle
community association
community amenities
SUBURBAN, WATER ACCESS
N/A
N/A

About the Area
Regional Background
The Eastern Shore is characterized by waterfront towns, agricultural landscapes, and a slower, more intentional pace of life. Buyers are often motivated by lifestyle considerations, privacy, and long-term ownership, including second-home purchasers and those seeking an alternative to more densely populated markets. Real estate activity in the region reflects a strong connection to place and a preference for quality over speed.
Lifestyle Pillars
Waterfront, Second-Home, Historic towns, Agriculture, Quiet luxury
Related Market Reports
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2077 Somerville Rd
suite 200
Annapolis, MD 21401



























