Chesapeake Beach Real Estate

Chesapeake Beach Real Estate

Welcome to Chesapeake Beach, a charming waterfront town nestled in Calvert County, Maryland. Known for its picturesque views of the Chesapeake Bay, this coastal community offers a perfect blend of small-town charm and modern amenities.

Chesapeake Beach boasts a rich history dating back to the 19th century when it was a popular vacation destination for city dwellers looking to escape the summer heat. Today, the town continues to attract visitors and residents alike with its sandy beaches, marinas, and scenic boardwalks.

In addition to its natural beauty, Chesapeake Beach offers a variety of recreational activities for outdoor enthusiasts. From fishing and boating to hiking and birdwatching, there is no shortage of ways to enjoy the great outdoors in this waterfront paradise.

With its convenient location just a short drive from Washington, D.C., Chesapeake Beach provides the perfect retreat for those looking to escape the hustle and bustle of city life without sacrificing convenience.

Whether you're looking for a weekend getaway or a place to call home, Chesapeake Beach has something for everyone. Come explore all that this charming coastal town has to offer and discover why it's one of Maryland's best-kept secrets.

Newest Listings in Chesapeake Beach

$517,000
3 Beds ⋅ 3 Baths
Nestled on a tranquil 1.2-acre lot, this beautifully updated 3-bedroom, 2.5-bath colonial is the perfect family retreat just minutes from Washington DC, Joint Base Andrews, and Annapolis. Imagine your kids playing in the expansive yard while you relax in the sunroom, warmed by the cozy wood-burning stove. This home features a 50 year roof (2018), newly updated bathrooms (2024), new hardscaping/landscaping (2024) and a 12x24 Shed (2023)! HVAC was replaced in 2021. This meticously maintained home offers the perfect mix of privacy, space, and convenience for your growing family!

5530 Cheryl Ln, Chesapeake Beach

Listing courtesy of CENTURY 21 New Millennium. Contact: (443) 968-9595
$650,000
4 Beds ⋅ 2 Baths
Looking to move to the quaint town of Chesapeake Beach? Fully renovated and furnished turn key home located close to the Restaurants, Private Beach, Casinos, Water Park, New Library, Community Center, Boating and Boardwalks, yet tucked back out of the hustle and bustle of downtown. Updates to the home include: Kitchen, Baths, Hardwood, finished lower level, Large Screen TV, Washer, Dryer, HVAC, bedrooms, leather couches, love seats and recliners, kitchen island, gaming table, loads of closets, new shelving units, siding & gutters, windows, and roof! Features 4 bedrooms, 2 full bathrooms, a large deck off the kitchen overlooking a large & level back yard with a mature shade tree, walkout sliding glass door to the private, newly vinyl-fenced yard. Muskogee Crape Myrtles strategically planted between your deck and the neighbors will add to your privacy. Brand new shed / workshop, 15'x8'. In the highly desirable and safe Northern Calvert County with easy access from Rt260, this home is an absolute Gem and fully move in ready. Don't miss out!

3709 29th St, Chesapeake Beach

Listing courtesy of Hawkins Real Estate Company. Contact: (410) 413-3575
$374,900
3 Beds ⋅ 4 Baths
Photos and additional information COMING SOON * Updated kitchen, hardwood flooring through main level, lower level finished with entertaining kitchenette, deluxe primary suite * walking distance to beaches, trails, shops, dining and more!

8244 Silverton Ct, Chesapeake Beach

Listing courtesy of RE/MAX One. Contact:

$299,000
2 Beds ⋅ 1 Baths
Exciting professional photos are on the way for this charming 2-bedroom, 1-bath rambler located just three blocks from the beautiful Chesapeake Bay and the beach. Renovated in 1989, this home features a spacious, flat, fenced yard perfect for relaxation and outdoor activities. With two generously sized bedrooms and the added benefit of being zoned for both residential and town commercial use, this property is ideal for those looking to work from home. Seize this incredible opportunity—schedule your appointment today!

3728 Chesapeake Beach Rd E, Chesapeake Beach

Listing courtesy of CENTURY 21 New Millennium. Contact: (443) 968-9595
$359,000
3 Beds ⋅ 1 Baths
Exciting professional photos are on the way! Here’s your chance to embrace a lifestyle by the beach while working in a vibrant community! This charming 3-bedroom, 1-bath residence is situated just three blocks from the Bay and offers the unique advantage of being zoned for both Town Commercial and Residential use. The possibilities are endless—seize this opportunity to explore your future home! Schedule your tour today!

3718 Chesapeake Beach Rd E, Chesapeake Beach

Listing courtesy of CENTURY 21 New Millennium. Contact: (443) 968-9595
$359,900
2 Beds ⋅ 2 Baths
This home was updated in 2023 with new landscaping, deck, stainless steel appliances, a holding tank alarm, and a water softener system. The spacious basement features a rec room, while the first floor includes a kitchen, bedroom, full bathroom, large living room, and access to a spacious deck perfect for entertaining. The loft on the top floor has its own bedroom and private full bathroom. Whether you're looking for a new home or a potential Airbnb investment, this property is ideally located near the water and popular landmarks. Landmark distances: • Bayfront Beach and Park: 0.4 miles • US Naval Research Laboratory: 0.8 miles • Chesapeake Beach Water Park: 1.9 miles • Chesapeake Beach Veterans Memorial Park: 2 miles • North Beach Boardwalk: 2.9 miles • Chesapeake Beach Railway Trail: 3.2 miles

4119 Chesapeake Ave, Chesapeake Beach

Listing courtesy of Samson Properties. Contact: (703) 378-8810
$950,000
6 Beds ⋅ 5 Baths
Welcome to this one-of-a-kind Calvert County home, just off Plum Point Creek, with unobstructed views of the creek and Chesapeake Bay! This property is situated on 3.53 acres and provides abundant privacy and unmatched outdoor living space. The home was updated in 2024, featuring new carpet, updated bathrooms (2), hardwood floors, a finished basement, paint, and more! The house boasts 6 spacious bedrooms with 4 1/2 baths, including a master bedroom on the first floor with an en-suite bathroom! Laundry facilities are conveniently located on both the first and second floors, with the option to add another in the finished basement. The attached 3-car garage features an abundance of space for cars and trucks, with plenty of room for a workshop if desired. Enjoy the oversized Trex deck off the rear with incredible views of Plum Point Creek, perfect for entertaining family and friends. In 2024, new exterior hardscaping was added, including a walkway and patio. The fire pit location captures some of the most stunning views of this property overlooking the Chesapeake Bay and Sharps Point Lighthouse, the perfect spot to enjoy those crisp fall evenings soon to come. Nestled in the woods sits a full sized treehouse which conveys! Where the backyard meets the creek, there is a kayak and paddleboard launch to explore the natural beauty of the winding creek and its abundant wildlife year-round! For boating enthusiasts, Breezy Point Marina is just a 5-minute drive away, offering deep-water slips for both powerboats and sailboats. The community HOA also provides access to a private, gated beach just north of the marina—an excellent spot for a beach day or picnic. Convivence, convenience, convenience! Breezy Point Market is just a 5-minute drive from the house for all of your food, beer, and wine needs. This home is truly the finest in the neighborhood, offering unmatched views and water access that no other lot provides. An additional 20 acres of protected community property w/ nature trail is located to the right of the driveway as you decent towards the home. Just 34 miles from historic Downtown Annapolis and 43 miles from DC! Take advantage of this rare opportunity and schedule a showing today! Assumable VA loan at 2.25%. Carpet allowance for upstairs is being offered. ***Public records are incorrect. Total finished square footage is 4,272***

3101 Blue Heron Dr S, Chesapeake Beach

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$427,000
3 Beds ⋅ 2 Baths
Wonderful 2 level home with 3 bedrooms and 2 baths. Home boasts New wood laminate flooring on main level and New carpet in the lower level an inviting eat in kitchen and a cozy screened in porch appointed with a new gorgeous wood ceiling. All this and a wonderful wrap around deck, large fenced in back yard and shed. All it needs is you!

8779 Saint Andrews Dr, Chesapeake Beach

Listing courtesy of MDC Realty. Contact:

$259,900
3 Beds ⋅ 2 Baths
Welcome to this rancher home in the water-oriented community of Chesapeake Beach. Home features three spacious bedrooms with built-in closet, a full bathroom with soaking tub, a formal living room that leads to the kitchen-dining room combo with wood cabinets, tile floors and appliances. This home offers the wonderful blend of convenience and coastal charm. It is closely located to the beaches with beautiful water views of the Chesapeake Bay and a few minutes away from local dining and shopping center. So, embrace this wonderful opportunity and schedule your showings today.

7533 Bayside Rd, Chesapeake Beach

Listing courtesy of Century 21 Downtown. Contact:

$599,999
4 Beds ⋅ 4 Baths
Welcome Home! It may look like just a lot, but the new home that will be built there will be everything you want it to be. Really! Since this home hasn't been built yet, our builder is open and allowing for customizations and luxurious upgrades to suit your specific needs and style. Imagine choosing your finishes and making this home truly yours! The home we chose for this property is called the "Ramsey" model. This model is adorned with 3 sizeable bedrooms and an Owner's Suite. The Owner's Suite has an enormous walk-in-closet that is big enough for a center island and space for dressing. The Ensuite is slated for a dual vanity with a tub/shower combo. Just remember, you can make that into a large soaking tub and stand up shower, or however else you prefer. When you walk into the front door, you are greeted with an abundance of natural light that just pours into the room. You are able to see straight through the home with no obstructions and look straight into your backyard! It's like getting the feeling of openness, but on a whole new level. The This home is designed to provide both luxury and convenience. The stone, propane fireplace in the family room adds warmth to the living space, creating a cozy atmosphere for those chilly Maryland evenings. Located just minutes from the Chesapeake Bay, you’ll enjoy easy access to the area's stunning waterfront, boardwalk, and beaches. Chesapeake Beach is home to local marinas, seafood restaurants, and scenic parks like Bayfront Park and Veterans Memorial Park. It's in close proximity to top-rated schools and offers a vibrant yet relaxed coastal community atmosphere. Outdoor enthusiasts will appreciate the many trails and nearby fishing spots, while the nearby Chesapeake Bay Resort waits for you to enjoy it's wonderful ambience. Don’t miss this opportunity to build your custom dream home in one of Maryland’s most sought-after areas. Contact us today for more details!

4327 Dalrymple Rd, Chesapeake Beach

Listing courtesy of O'Brien Realty ERA Powered. Contact: 4103263133
$699,000
5 Beds ⋅ 4 Baths
WELCOME HOME! Located and nestled in this highly sought-after North Calvert Woods, you'll find this beautifully maintained home that offers so much to your family. Inside, you'll find gleaming hardwood floors, a wide open floor plan featuring a kitchen and family room with a propane fireplace, and formal living and dining rooms. The kitchen offers ample amount of counter space, a large island, barn style sink a large pantry. There is a large covered front porch perfect for your early morning coffee. While the back deck offers tranquility and privacy and plenty of space for entertaining. Nothing tops the beauty of the serene night star gazing this backyard has to offer. The privacy and just so much peace as it is treelined. The back deck offers the right spot for your evening glass of wine. Upstairs, you'll find the master bedroom and bath with a deluxe 2-person shower, and soaking tub. A large walk-in closet offers tons of space. You'll find three generously sized secondary bedrooms with large closets. BONUS upper level laundry room! The side-walkout basement is fully finished, with tons of natural lighting. GREAT FOR ENTERTAINING! Lower level offers a 5th bedroom and Jack and Jill full bath. This property is close proximity to the top local beaches, Shopping, restaurants, farmer's markets, community events, and more are all located in North Beach. The boardwalk offers some of the best sunrises in the morning. Marines local to dock your boat for a waterman's dream. THIS location is excellent for commuters to DC, Annapolis, Joint Base Andrews. Neighborhood events, playground and much more!

3636 Estelle Ct, Chesapeake Beach

Listing courtesy of CENTURY 21 New Millennium. Contact: (443) 968-9595
$99,990
This is a rare opportunity to own land and build new construction in the heart of Chesapeake Beach. Walk to everything the town has to offer. Just a short stroll to the boardwalk where you can watch the ships go by, see the sunrise, or walk to the town beach. This location is also walkable to restaurants, marinas, and concerts at the resort. It's the perfect spot to build your dream beach cottage. Less than an hour away from Washington, D.C. it's the perfect commuter location too. You don't want to miss this rare find. Bring your own builder or ask us about ours.

7536 C St, Chesapeake Beach

Listing courtesy of Keller Williams Flagship of Maryland. Contact:

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