Chesapeake Beach, MD Homes for Sale under $500,000

All New Carpet has been installed Since pictures and 3D tour was made!!!!!!!!! Come check it out.... its even better than the Pictures now!!!! Recent updates include new HVAC (2025), new roof (April 2026), new roof and wall insulation (2019), and remodeled powder room (2022), Freshly painted throughout. Move-in ready townhome in the sought-after San Francisco on the Bay community in North Beach,

Tara Kirby RE/MAX One

Private 1.28-acre cul-de-sac lot in the highly sought-after Highlands community * This home offers the perfect blend of comfort, privacy, and convenience. Backing to woods and featuring a large, private backyard, it's a peaceful setting while remaining close to everything the area has to offer. Recent updates include: New Luxury Vinyl Plank (LVP) Flooring – June 2026; New Hot Water Heater – 2025;

Lara Owings RE/MAX United Real Estate

Fabulous opportunity to own this well-maintained 3-bedroom, 2-bath split foyer in the desirable Highlands community of Chesapeake Beach! Situated on one of the best lots in the neighborhood, this home backs to woods and features a large, level backyard fully fenced with a privacy wood fence and rear chain-link fence with gate—perfect for pets, play, and outdoor enjoyment. The updated kitchen

Team Stueckler Keller Williams Flagship

Welcome to charming 6122 6th St, nestled within the Chesapeake Beach community. This home is back on the market with a new well, new roof, covered outdoor living area, separate fenced in yard, and overall refresh. This cozy home features two bedrooms, a remolded bathroom, and a spacious kitchen with lots of storage and brand-new appliances. The open floor plan allows unlimited opportunities for

Tiffany Oliver RE/MAX One

Discover an exquisite opportunity in the prestigious Summer City subdivision, where luxury meets tranquility. This stunning split foyer residence, boasts a generous 1,978 sq. ft. of thoughtfully designed living space, perfect for an exclusive lifestyle. Step inside to find a harmonious blend of elegance and functionality. The interior features a second kitchen and a traditional floor plan that

Gary Hart TCB Realtor, LLC.

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

Felicia Watkins White Samson Properties

Welcome to the end-unit penthouse you've been waiting for! This beautifully maintained 3-bedroom, 2.5-bath condo offers the perfect blend of comfort, convenience, and low-maintenance living in one of Chesapeake Beach's most desirable locations.Ideally situated for an easy commute to Washington, D.C., Joint Base Andrews, and Annapolis, you'll love coming home to the charm of the Chesapeake

Haley Taylor Real Broker, LLC - Dunkirk

BEAUTIFULLY UPDATED IN RICHFIELD STATION!! Welcome to this beautifully updated 4-bedroom, 3.5-bath interior townhome offering spacious, flexible living in the Richfield Station community of Chesapeake Beach. With fresh modern finishes, an open floor plan, and multiple living spaces, this home is move-in ready and designed to fit today's lifestyle. Step inside to find gleaming hardwood floors,

Mark Frisco CENTURY 21 New Millennium

*The sellers have set a deadline for Sunday, July 12th by 9PM. All offers will be reviewed and a decision will be made by Monday, July 13th no later than 12PM.* Welcome to easy one-level living in the sought-after Richfield Station community! This well-maintained home offers the functionality of a one level home, and the convenience of a spacious open layout designed for everyday living. The

Delaney Clarke RE/MAX United Real Estate

This 3-bedroom, 1-bath home on 4th Street blends modern updates with coastal charm in a prime Chesapeake Beach location. And it comes with a bonus: the sale includes the additional lot directly across the street. The exterior features fresh paint and blue accents that enhance its curb appeal, while the fenced yard adds privacy and function. "New septic system has just been installed"Inside,

Chris Craddock EXP Realty, LLC

Welcome to 4013 Seagate Square, ideally situated in the heart of Chesapeake Beach—one of the most desirable waterfront communities in Calvert County. This property offers the perfect blend of coastal charm and everyday convenience, just moments away.This spacious 3-level townhome nestled in the sought-after waterfront community of Seagate. Offering over 2,000 square feet of living space, this

Cynthia Taylor-Hicks Long & Foster Real Estate, Inc.

Fantastic opportunity to own this beautifully maintained END UNIT townhome situated on arguably the best lot in the highly desirable Bayview Hills community! Backing to open space and offering exceptional privacy, this home combines a peaceful setting with an unbeatable location for outdoor enthusiasts. Just steps from the Fishing Creek Rail Trail, you'll enjoy easy access to jogging, biking,

Team Stueckler Keller Williams Flagship

Coming Soon! Impeccably maintained 3-bedroom, 2.5-bath penthouse-style condo with over 2,600 sq ft and an attached garage in sought-after Richfield Station. Spacious open floor plan, abundant natural light, granite countertops, cherry cabinetry, and a luxurious primary suite with dual walk-in closets. Conveniently located near Chesapeake Beach, North Beach, shopping, dining, and commuter routes.

Joel Smith Fairfax Realty Premier

Motivated Sellers with Incredible 2.75% FHA Assumable Interest Rate Available! Escape to your own private woodland sanctuary at the end of a peaceful, quiet cul-de-sac. This enchanting home is truly an artist’s dream, bathed in dappled sunshine and offering a level of tranquility that is hard to find. The interior serves as a creative canvas, currently featuring vibrant custom murals that can

Genna Fleming Hyatt & Company Real Estate LLC

Enjoy the Chesapeake Beach lifestyle in this 2,600 sf penthouse condo in Northern Calvert! Plenty of parking for three cars here with a 1-car garage, separate driveway and one assigned parking space too! There is also additional visitor parking available. You'll love the extra privacy offered by this condo located across from open space-- with gorgeous views of mature flowering trees from the

Team Stueckler Keller Williams Flagship

*OPEN HOUSE HAS BEEN CANCELED FOR 7/12/2026* Beautifully updated 2-bedroom, 2-bath ranch home situated on a spacious fenced corner lot just two blocks from the Chesapeake Bay. This home features an open, airy floor plan with modern updates throughout and is conveniently located within walking distance to local restaurants, shops, marinas, beaches, and other town amenities. Recent upgrades include

Michelle Strickland Real Broker, LLC - Dunkirk

** PRICED UNDER VALUE - OWNER READY TO GO ** - Location location location - Lovely Chesapeake Beach split foyer with enclosed sunroom. Upper-level updated in 2021 with hardwood flooring, ceramic tile and huge kitchen. Seller owned solar panels are added plus for managing lower utility costs. Seller still clearing our rooms. Being sold AS-IS for simple transaction. Inspections for informational

Lisa Rosser Keller Williams Preferred Properties

Architecturally distinctive and thoughtfully designed, this exceptional Acorn Deck Home offers a rare opportunity to own one of the area's most celebrated post-and-beam residences. Located in the heart of Chesapeake Beach, 8205 F Street showcases the timeless craftsmanship and design principles Acorn Deck Homes are known for—soaring ceilings, warm natural materials, dramatic walls of glass, and

Doug Smith RE/MAX Realty Group

Just a 10-minute stroll to the North Beach Boardwalk, sandy beach, shops & some great places for local dining! Plus a brewery with live music, café and Saturday farmers market right at your doorstep. This beautiful 4-bedroom, 3.5-bathroom townhome offers the full coastal lifestyle in a move-in ready package. The open floor plan features hardwood floors throughout the living, kitchen, and dining

Monique Ligthart EXP Realty, LLC