Bentons Pleasure Real Estate

Bentons Pleasure Real Estate

Welcome to Bentons Pleasure, a charming legal subdivision nestled in the picturesque town of Chester, Maryland. Located in the heart of Queen Anne’s County, Bentons Pleasure offers a unique blend of serene living and vibrant community spirit, making it an ideal place to call home.

This delightful subdivision features a variety of residential properties, each designed to cater to diverse lifestyles. Whether you’re seeking a cozy cottage or a spacious family home, Bentons Pleasure has something for everyone. The lush greenery and well-maintained landscapes create a tranquil atmosphere, perfect for those who appreciate the beauty of nature.

Residents of Bentons Pleasure enjoy easy access to the stunning Chesapeake Bay, with its breathtaking views and recreational opportunities. Boating, fishing, and kayaking are just a stone’s throw away, allowing you to embrace the outdoor lifestyle. The area is also rich in history, with charming local shops, restaurants, and cultural attractions that reflect the heritage of Queen Anne’s County.

Families will appreciate the excellent school district and community programs that foster a sense of belonging among neighbors. The friendly atmosphere encourages gatherings and events, making it easy to form lasting friendships.

With its prime location, Bentons Pleasure offers the perfect balance of peaceful living and accessibility to nearby urban amenities. Experience the warmth and charm of this inviting community, where you can create lasting memories and enjoy the best of Maryland living. Come explore Bentons Pleasure, where your dream home awaits!

Newest Listings in Bentons Pleasure

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

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:

Kent Island Waterfront on Cox Creek!! Public Sewer available, road frontage is 45ft. This is a flag lot with opening on the waterfront of 108 ft. This property does not have a pier, so please do not go on pier. This is the perfect lot to build your dream home. The natural environment has wildlife and waterfowl and as well as good fishing and crabbing. If you want a piece of the shore-life this is the property you have been looking for. Seller will consider holding a note for purchaser.

Parks Rd, Chester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

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