Chesapeake Beach, MD Homes for Sale

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  $99,000

  • Land
  • 20,908 Sq Ft
  • $206,250 per Acre

  Lot 22R Block 7 18th St, Chesapeake Beach, MD 20732

  Your chance to build your dream home above it all. Perched on a hill in the coveted Chesapeake Beach area, this nearly 1/2 acre lot offers an unparalleled lifestyle. You're just minutes to the Boardwalks, beach, resort style dining, charter fishing, and more! Don't miss this rare opportunity. Come see the potential for yourself.

  Robyn Day RE/MAX One

  Lot 22R Block 7 18th St, Chesapeake Beach, MD 20732
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  $674,900

  Open Sun 1PM - 3PM

  • 4 Beds
  • 2.5 Baths
  • 2,706 Sq Ft

  3611 Karen Dr, Chesapeake Beach, MD 20732

  Welcome home to this stunning property in the highly sought‐after Lake Karylbrook community, offering a serene, private setting on over 3 acres. This immaculate, professionally designed 4‐level home features 4 finished levels, nearly 3500 sqft of finished living space, 4 bedrooms, 2.5 baths, and a welcoming front porch, a spacious deck perfect for outdoor enjoyment. Step outside and enjoy summer

  Denis Guma RE/MAX Advantage Realty

  3611 Karen Dr, Chesapeake Beach, MD 20732
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  /50

  $759,900

  • 3 Beds
  • 4.5 Baths
  • 2,583 Sq Ft

  8048 Windward Key Dr, Chesapeake Beach, MD 20732

  Discover coastal living at its finest at 8048 Windward Key Dr, Chesapeake Beach! This "as-is" gem offers breathtaking views of the canal and the iconic Chesapeake Bay, placing you right in the heart of everything this charming waterfront town has to offer. Located just steps away from the renowned Rod 'N' Reel Resort, you'll enjoy the convenience of walking to local restaurants, marina boat

  Chris Moore Compass

  8048 Windward Key Dr, Chesapeake Beach, MD 20732
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  $535,000

  $15K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,296 Sq Ft

  4010 Beach Dr, Chesapeake Beach, MD 20732

  Tucked into the sought-after Holiday Beach community in Chesapeake Beach, this classic colonial offers the perfect blend of comfort, charm, and the relaxed southern Maryland lifestyle so many buyers are searching for. Enjoy community water access along with easy proximity to all the dining, shopping, marinas, and recreation that make the Chesapeake Bay lifestyle so special. Inside, hardwood

  Dee Dee Miller Paul Wesley Real Estate

  4010 Beach Dr, Chesapeake Beach, MD 20732
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  $390,000

  $15K PRICE DROP

  • 6 Beds
  • 2 Baths
  • 2,080 Sq Ft

  6337 Dory Ct, Chesapeake Beach, MD 20732

  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

  6337 Dory Ct, Chesapeake Beach, MD 20732
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  $369,990

  • 3 Beds
  • 2.5 Baths
  • 2,600 Sq Ft

  2336 Forest Ridge Terrace, Chesapeake Beach, MD 20732

  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

  2336 Forest Ridge Terrace, Chesapeake Beach, MD 20732
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  $365,000

  Coming Soon

  • 2 Beds
  • 2.5 Baths
  • 1,658 Sq Ft

  2233 Ivy Ln Unit 3, Chesapeake Beach, MD 20732

  Enjoy easy, low-maintenance living in this beautifully maintained GROUND LEVEL 2-bedroom, 2.5-bath condo located in one of Chesapeake Beach's most sought-after communities, Richfield Station. Conveniently situated for commuters traveling to Washington, D.C., JBA, and Annapolis, this home also offers the opportunity to enjoy all the charm and amenities of Chesapeake Bay living. The bright, open

  Erika Kaine Samson Properties

  2233 Ivy Ln Unit 3, Chesapeake Beach, MD 20732
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  /17

  $165,000

  $34K PRICE DROP

  • Land
  • 6,534 Sq Ft
  • $1,100,000 per Acre

  8314 Bayside Rd, Chesapeake Beach, MD 20732

  PRICE IMPROVEMENT on this amazing lot in Chesapeake Beach. Rare opportunity to build your custom home on a prime lot with Chesapeake Bay views. Located at 8314 Bayside Road, this property offers year-round water views, coastal charm, and the convenience of public water, sewer hookups, and electric availability. Relax on your new front porch soaking in the bay breeze and peaceful surroundings.

  Erin Roccapriore JPAR Real Estate Professionals

  8314 Bayside Rd, Chesapeake Beach, MD 20732
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  /23

  $399,900

  $58K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,444 Sq Ft

  3606 27th St, Chesapeake Beach, MD 20732

  ** 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

  3606 27th St, Chesapeake Beach, MD 20732
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  $989,000

  • 5 Beds
  • 4 Baths
  • 6,659 Sq Ft

  3640 Estelle Ct, Chesapeake Beach, MD 20732

  Situated on 2+ private acres, you'll find this home truly has it all! Beautifully built in 2018 and impeccably maintained inside and out, its timeless stone-front façade is as elegant as it is enduring — the perfect setting for the whole family or comfortable multi-generational living. Inside, a bright and open modern layout welcomes you. The heart of the home is a large eat-in kitchen complete

  Holly Bennett Curtis Real Estate Company

  3640 Estelle Ct, Chesapeake Beach, MD 20732
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  /50

  $475,000

  Open Sun 10AM - 12PM

  • 4 Beds
  • 3.5 Baths
  • 2,875 Sq Ft

  3781 Bedford Dr, North Beach, MD 20714

  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

  3781 Bedford Dr, North Beach, MD 20714

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