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4884 Ridge Rd, Chesapeake Beach
$365,000
3 Beds ⋅ 1 Baths
Welcome to this charming, move-in-ready home in the coastal community of Breezy Point! Offering approximately 1,200 square feet, this inviting 3-bedroom, 1-bath home features an updated kitchen with a newer refrigerator and stove, beautiful hardwood floors, and a spacious living room with vaulted ceilings. The light-filled sunroom provides flexible space for relaxing, entertaining or working from home. Step outside onto the expansive wraparound deck, where you can enjoy the peaceful surroundings and seasonal views of the Chesapeake Bay. A lovely English-style backyard garden, mature fig tree offering fresh figs each August, colorful plantings and stone landscaping in the front yard add to the home’s storybook charm. Notable improvements include HardiePlank siding, a roof installed in September 2021, Andersen windows across the back of the home installed in June 2023, HVAC replaced in May 2025 and a new septic holding tank installed in April 2026. Community amenities include a private beach for residents and their guests, free access to the county park featuring approximately half a mile of Chesapeake Bay beachfront, a playground and fishing pier, plus a public marina. Enjoy the relaxed coastal lifestyle year-round or make this special property your weekend retreat!

4884 Ridge Rd, Chesapeake Beach

Listing courtesy of Samson Properties. Contact:

Selling Office: Berkshire Hathaway HomeServices PenFed Realty.

4820 Sherwood Ave, Chesapeake Beach
$340,000
3 Beds ⋅ 2 Baths
Opportunity to obtain a spacious home in a community with beach access. The Breezy Point Community has access to the beach through voluntary dues, not mandatory ones. The beautiful beach is within walking distance and also offers a large picnic area. The home is being sold as is by the estate. The special features include new carpet on the main level and a new roof between 2021 and 2022. Solar panels have been installed and will be paid in full at closing. The family is working on cleaning out the home, which is why we haven't displayed pictures of all the rooms. There are 2 bedrooms on the main level, and a 3rd bedroom was converted into a laundry/storage room. There is also a w/d hookup in the basement if you want to convert that room back to a bedroom. The lower level is partially finished and in need of renovation. There is a wood stove in the lower-level family room that heats the house during a cold spell. There are 2 spacious garages, currently full of belongings. The screened-in porch is large and great for entertaining. There is a covered area for parking 2 cars or grilling, and plenty of concrete driveway spaces for parking. The front yard is fenced in to keep the children and pets safe.

4820 Sherwood Ave, Chesapeake Beach

Listing courtesy of O'Brien Realty ERA Powered. Contact:

Selling Office: Non Subscribing Office.

5229 Breezy Point Rd, Chesapeake Beach
$370,000
2 Beds ⋅ 1 Baths
Chesapeake Beach Coastal Retreat 🌊 Welcome to 5229 Breezy Point Rd, Chesapeake Beach, MD — your perfect escape by the water! ✨ 2 Bedrooms, 1 Bath ✨ Sleeps 5–6 comfortably ✨ Steps from the beach ✨ Fully renovated & move-in ready ✨ Breathtaking sunrises and sunsets Imagine waking up to the sound of the waves, sipping coffee while watching the sunrise over the Chesapeake Bay, and ending your evenings with stunning sunset skies just steps from your door. This charming coastal retreat offers the perfect blend of relaxation and modern comfort, making it ideal as a primary residence, weekend getaway, vacation home, or investment property. Enjoy beach walks, salty breezes, peaceful mornings, and the laid-back Chesapeake Beach lifestyle — all at an incredible value. Whether you're entertaining guests, escaping city life, or searching for your own slice of waterfront paradise, this home delivers the lifestyle everyone dreams about. You've got to come to this “Affordable Coastal Living Home With Private Beach Access — Without the Million-Dollar Price Tag.” Still being within commuting distance to DC/MD/VA areas At $370K, this listing hits a sweet spot for: first-time buyers, downsizers, weekend/vacation-home buyers military buyers using VA buyers priced out of Annapolis waterfront living, remote workers wanting lifestyle over square footage. Come take a look and Say Yes to this Address! (The furnishings may be negotiable)

5229 Breezy Point Rd, Chesapeake Beach

Listing courtesy of Samson Properties. Contact:

Selling Office: Samson Properties.

3304 Burgess Rd, Chesapeake Beach
$185,000
2 Beds ⋅ 3 Baths
Back to market with a HUGE price reduction! Calling all investors! Welcome to Breezy Point, one of Chesapeake Beach's most desirable waterfront communities! Just a short stroll from the Chesapeake Bay, this charming home offers the opportunity to enjoy the relaxed coastal lifestyle you've been looking for. One of the larger homes in the neighborhood, this property features a full walk-out basement, a small garage parking space, and plenty of potential to create the home of your dreams. While it could benefit from some updates and repairs, its generous size, character, and inviting beach-town feel provide the perfect canvas for your vision. Residents enjoy access to a private, residents-only community beach featuring a sandy shoreline, expansive grassy areas, breathtaking sunrise views, and a pet-friendly atmosphere for leashed dogs. You'll also have free access to a nearby county park with a fishing pier, picnic areas, a playground, and nearly a half-mile of beautiful beachfront. A voluntary community civic association offers a beach key and hosts neighborhood events throughout the year, creating a welcoming sense of community. Whether you're looking for a year-round residence, a weekend getaway, or an investment opportunity, this home offers an incredible chance to add your personal style in a sought-after Chesapeake Beach location. Come discover the charm, the community, and the endless possibilities waiting for you in Breezy Point. This is an as-is where is sale.

3304 Burgess Rd, Chesapeake Beach

Listing courtesy of Keller Williams Flagship. Contact:

Selling Office: Redfin Corp.

5233 Breezy Point Rd, Chesapeake Beach
$370,000
2 Beds ⋅ 1 Baths
Chesapeake Beach Coastal Retreat 🌊 Welcome to 5237 Breezy Point Rd, Chesapeake Beach, MD — your perfect escape by the water! ✨ 2 Bedrooms, 1 Bath ✨ Sleeps 5–6 comfortably ✨ Steps from the beach ✨ Fully renovated & move-in ready ✨ Breathtaking sunrises and sunsets Imagine waking up to the sound of the waves, sipping coffee while watching the sunrise over the Chesapeake Bay, and ending your evenings with stunning sunset skies just steps from your door. This charming coastal retreat offers the perfect blend of relaxation and modern comfort, making it ideal as a primary residence, weekend getaway, vacation home, or investment property. Enjoy beach walks, salty breezes, peaceful mornings, and the laid-back Chesapeake Beach lifestyle — all at an incredible value. Whether you're entertaining guests, escaping city life, or searching for your own slice of waterfront paradise, this home delivers the lifestyle everyone dreams about. You've got to come to this “Affordable Coastal Living Home With Private Beach Access — Without the Million-Dollar Price Tag.” Still being within commuting distance to DC/MD/VA areas At $380K, this listing hits a sweet spot for: first-time buyers, downsizers, weekend/vacation-home buyers military buyers using VA buyers priced out of Annapolis waterfront living, remote workers wanting lifestyle over square footage Come take a look and Say Yes to this Address! (The furnishings are negotiable)

5233 Breezy Point Rd, Chesapeake Beach

Listing courtesy of Samson Properties. Contact:

Selling Office: CENTURY 21 New Millennium.

5237 Breezy Point Rd, Chesapeake Beach
$370,000
2 Beds ⋅ 1 Baths
Chesapeake Beach Coastal Retreat 🌊 Welcome to 5237 Breezy Point Rd, Chesapeake Beach, MD — your perfect escape by the water! ✨ 2 Bedrooms, 1 Bath ✨ Sleeps 5–6 comfortably ✨ Steps from the beach ✨ Fully renovated & move-in ready ✨ Breathtaking sunrises and sunsets Imagine waking up to the sound of the waves, sipping coffee while watching the sunrise over the Chesapeake Bay, and ending your evenings with stunning sunset skies just steps from your door. This charming coastal retreat offers the perfect blend of relaxation and modern comfort, making it ideal as a primary residence, weekend getaway, vacation home, or investment property. Enjoy beach walks, salty breezes, peaceful mornings, and the laid-back Chesapeake Beach lifestyle — all at an incredible value. Whether you're entertaining guests, escaping city life, or searching for your own slice of waterfront paradise, this home delivers the lifestyle everyone dreams about. You've got to come to this “Affordable Coastal Living Home With Private Beach Access — Without the Million-Dollar Price Tag.” Still being within commuting distance to DC/MD/VA areas At $380K, this listing hits a sweet spot for: first-time buyers, downsizers, weekend/vacation-home buyers military buyers using VA buyers priced out of Annapolis waterfront living, remote workers wanting lifestyle over square footage Come take a look and Say Yes to this Address! (The furnishings are negotiable)

5237 Breezy Point Rd, Chesapeake Beach

Listing courtesy of Samson Properties. Contact:

Selling Office: RE/MAX Plus.

4873 Highland Ter, Chesapeake Beach
$365,000
2 Beds ⋅ 2 Baths
Nestled in the charming Breezy Point neighborhood, this delightful split foyer home offers a perfect blend of comfort and functionality. Built in 1996, the exterior features a classic brick front and durable vinyl siding, ensuring lasting appeal. Step inside to discover a fully finished basement, ideal for relaxation or entertaining. The heart of the home boasts a combination kitchen and dining area, complete with essential appliances like a dishwasher, electric dryer, washer, stove, and refrigerator, making meal prep a breeze. Enjoy the gentle breeze from the ceiling fans throughout the home, enhancing the inviting atmosphere. Outside, the property features a well-maintained gutter system and an outbuilding for extra storage. With a manageable lot size of 0.13 acres, there's plenty of room for outdoor activities. Convenient shared driveway parking adds to the ease of living. Located near local amenities, this home is a true gem waiting to be cherished. REPAIRS 2023: New Heat Pump/Central Air. REPAIRS 2024: New Roof, New Gutters with Leaf Protection, New Well. REPAIRS 2026: See Receipt in Agent Docs. BGE Budget Plan 212/Month. Just S T E P S away from a Public Beach Access!

4873 Highland Ter, Chesapeake Beach

Listing courtesy of RE/MAX Leading Edge. Contact:

Selling Office: RE/MAX One.

3402 Hillside Pl, Chesapeake Beach
$465,000
3 Beds ⋅ 3 Baths
SELLER OFFERING 1-0 RATE BUY DOWN!!! Hillside Place is simple coastal class , meets Calvert County country. This thoughtfully, renovated rambler is truly the best of both worlds when it comes to design. On the main floor you will find gorgeous tiles, beachwood colored & water resistant laminate flooring, gold fixtures, stylish lighting, and lots of natural light from the expansive bay window. On this floor you will have seasonal views of the Chesapeake Bay. You will feel as though you are truly on top of the world while looking out from the almost top of the hill, corner lot property. The kitchen features a 9 foot galley style built-in buffet with a mermaid tile backsplash and gorgeous quartz countertops. It is generously accompanied by a large breakfast area that leads to the backyard. At the front of the house, you will find a formal dining room and a large living room. Down the hall there are two bedrooms and a full bath, along with the primary suite featuring an en suite bathroom. The shower extends that beachy vibe with sea glass tile inserts, and sandy white tiles covering the walls of the shower. Hillside Place also features a fully finished basement. You can access the basement from the kitchen or from outside through the side entrance. The basement has a warm and cozy feel with lush, new, neutral colored carpet, rustic, light, fixtures, two large bonus rooms and a recreational room already wired with in- wall set up for TV hook up. In the basement, you will also find a full bathroom complete with custom barn door entry. The laundry and utility room is also in the basement. Although some landscaping has been done, including a new retaining wall, gravel parking pad,seed. & straw, front walkway with pebbles and stepping stones, and lots, and lots of brush, shrub, tree and trailer removal, there is still plenty of room for you to create the backyard of your dreams. You’ve got a clean slate to work with, and the possibilities are endless. I would be remiss if I did not mention that the roof, soffit, gutters, siding, windows and doors, with the exception of one door have all been replaced brand new! The drain fields, 14 feet deep with above and beyond gravel and pipe, have been Majorly overdone and are only three years old. This home also has. an oversized 2 car, sideload attached garage. Enjoy all the neighborhood of Breezy point has to offer all year round. Most recently they decorated the meadow for the holidays. Throughout the year, they host various community events, as well as the year-round access to the private neighborhood beach, as well as the public beach, the marina and playground.

3402 Hillside Pl, Chesapeake Beach

Listing courtesy of RE/MAX United Real Estate. Contact:

Selling Office: Samson Properties.

2950 Tobacco Rd, Chesapeake Beach
$519,650
4 Beds ⋅ 3 Baths
SHOW FOR BACK UPS. NO HOA! Tucked away on a private, wooded five acre setting, this striking contemporary home offers space, privacy, and a story that sets it apart. Known by many in the Chesapeake Beach area and throughout Northern Calvert County, the home gained recognition after a renovation featured on The Ellen Show. Since then, it has been thoughtfully updated again while off the market, with a focus on the improvements that matter most. All major systems have been addressed. A BAT septic system with new drain fields was installed in 2021. The architectural shingle roof was fully replaced in 2022. A brand new electric HVAC system was installed in 2025, with the manufacturer warranty transferring to the new owner at closing. Beautifully refinished hardwood floors run throughout the main living spaces, giving the home a warm and polished feel. The main level is open and filled with natural light. The eat in kitchen features vaulted ceilings, skylights, marble countertops, and Viking oven, making it both functional and visually striking. The living room centers around a propane fireplace with a built in mantle and shelving, creating a comfortable space for everyday living or entertaining. Sliding barn doors lead to the MAIN LEVEL PRIMARY bedroom and private bath suite, offering convenience and separation from the rest of the home. At the rear of the house, a spacious Trex deck overlooks the wooded landscape. Thoughtful landscaping, stone, and pavers below the deck enhance the setting and make it easy to enjoy quiet mornings or relaxed evenings outdoors. The upper level includes two additional bedrooms and a full bath, ideal for guests or flexible use. The lower level is newly renovated. It already includes a third full bath, a recreation area, an additional room suitable for a possible fourth bedroom, and a rough in for a future wood burning stove. The property itself is a standout. Covered parking, a paved driveway, two storage sheds, and even a treehouse are already in place. The treehouse conveys as is, with condition unknown. With five wooded acres, this property is well suited for nature lovers, those seeking privacy, or anyone wanting a true retreat without giving up convenience. Despite the peaceful setting, the location offers easy access to local favorites like the farmers market, boardwalk, and well loved restaurants. Commuters will appreciate proximity to Joint Base Andrews, Annapolis, Patuxent River, and Washington, D.C.. This is a home where the heavy lifting has already been done. The systems are in place, the setting is exceptional, and the next chapter is ready to be written. Some photos are Virtually Staged.

2950 Tobacco Rd, Chesapeake Beach

Listing courtesy of RE/MAX One. Contact:

Selling Office: RE/MAX United Real Estate.

4790 Howard Pl, Chesapeake Beach
$390,000
3 Beds ⋅ 2 Baths
Welcome to your coastal retreat in Chesapeake Beach! This beautifully updated 3-bedroom, 2-bath single-family home offers over 2,000 square feet of thoughtfully designed living space, blending comfort, style, and modern convenience. Enjoy peace of mind with a brand-new HVAC system (2024), new washer and dryer (2024), and professionally cleaned air ducts and vents (October 2025). Additional upgrades include a chemical feeder and water softener system (2021), tastefully renovated bathrooms and more all contributing to a truly move-in-ready home. Inside, the spacious recreation room and dedicated exercise room offer endless possibilities for relaxation, entertainment, or wellness. Step outside to a generous deck—perfect for hosting gatherings or enjoying quiet evenings under the stars. The modernized kitchen includes granite countertops and stainless steel appliances. Located just a short stroll from Breezy Point Beach, this home captures the essence of coastal living. Whether you’re seeking a profitable Airbnb or investment property, a peaceful beach community getaway, or a comfortable primary residence, this versatile home checks every box. Don’t miss your chance to own a slice of Chesapeake Beach paradise—where modern upgrades meet timeless coastal charm, and every day feels like a vacation.

4790 Howard Pl, Chesapeake Beach

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

Selling Office: RE/MAX One.

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