Bentons Pleasure Homes for Sale

Welcome to Bentons Pleasure, a hidden gem nestled in the heart of Chester, Maryland, within the picturesque Queen Anne's County. This charming legal subdivision offers a unique blend of serene living and vibrant community spirit, making it an ideal place for families, retirees, and anyone seeking a peaceful retreat while still being close to modern conveniences.

Bentons Pleasure is characterized by its beautiful landscapes, featuring lush greenery and scenic views that create a tranquil ambiance. The homes here boast a variety of architectural styles, from cozy cottages to spacious family residences, each offering a unique charm and character. Whether you’re looking for a weekend getaway or a permanent residence, Bentons Pleasure has something to suit every taste and budget.

Currently, there are homes for sale in this delightful community, providing a fantastic opportunity for prospective buyers to invest in a lifestyle that combines relaxation and recreation. With easy access to local parks, waterfront activities, and community events, residents can enjoy a vibrant outdoor lifestyle. The nearby Chester River offers fishing, boating, and stunning sunsets, perfect for those who appreciate nature's beauty.

Living in Bentons Pleasure means being part of a welcoming community where neighbors become friends. With its convenient proximity to shopping, dining, and excellent schools, this subdivision is not just a place to live, but a place to thrive. Explore the homes for sale in Bentons Pleasure today and discover the perfect blend of comfort, community, and charm in this idyllic Maryland locale. Your dream home awaits!

Newest Bentons Pleasure Homes for Sale

$629,900

3 Beds ⋅ 2 Baths

This 3 bedroom 2 full bath brick rancher is located 1.88 for plenty of privacy and plenty of room to expand. Not many large lots left in this community, check with county for very possible sub dividing for 2 additional lots. Home is in need of updating with lots of potential to add your own touch and design. More pictures coming soon. Currently on septic but sewer is available.

315 Bentons Pleasure Rd, Chester

Listing courtesy of Douglas Realty LLC. Contact: (866) 987-3937

$2,840,000

3 Beds ⋅ 2 Baths

Rare Find - 2 houses on one waterfront property! Each with unobstructed views of the water! Privacy without isolation. This will change your mind if you think you need 5 acres or more to have wide open spaces and not have neighbors breathing down your neck! Discover a captivating blend of traditional charm in the vintage cape cod - the main 3-bedroom, 2-bathroom residence, recently updated in spring 2026. Nestled in a serene rural setting, this home boasts picturesque views along the banks of Cox Creek, offering panoramic western vistas that will take your breath away, especially as the sun sets on the horizon. Step inside to find a thoughtfully designed interior featuring rich wood floors and upgraded countertops that elevate the kitchen, a home perfect for gatherings. The cozy living room, complete with a brick fireplace and mantel, invites warmth and relaxation. Enjoy the convenience of an entry-level bedroom and a traditional floor plan that flows seamlessly throughout. The exterior is equally impressive, featuring a private beach and a circular gravel driveway that accommodates ample parking. With 548 feet of waterfrontage, indulge in fishing, boating, or simply soaking in the tranquil surroundings. The property includes a private dock with electric hoist and ramp, making water access effortless. Additional highlights include a guest house(2BR, 1.5 BA, KT,screened porch) and a storage building providing versatility for equipment or hobbies. The secluded parcel offers year-round access, ensuring your retreat is always within reach. This home is not just a residence; it's a lifestyle waiting to be embraced. Don't miss the opportunity to make this serene haven your own! Less than 30 minutes to Annapolis, 50 minutes to Baltimore or DC.. Convenient to area restaurants and points of interest. Not under subdivision restrictions. Perfect for multi-generational living, private guest quarters, or possible rental income. Room for expansion of living spaces, outdoor sports court, horseshoes, bocci, or garden. Former waterside pool could be revitalized, subject to county approval.

300 Woods Point Rd, Chester

Listing courtesy of Tidewater Properties. Contact:

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