5,005

Chesapeake Beach, MD Homes

Section Image
  • /33

    $380,000

    Pending
    • 2 Beds
    • 1 Bath
    • 896 Sq Ft

    5237 Breezy Point Rd, Chesapeake Beach, MD 20732

    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

    5237 Breezy Point Rd, Chesapeake Beach, MD 20732
  • /42

    $3,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,231 Sq Ft
    • Condo for Rent

    8501 Bayside Rd, Chesapeake Beach, MD 20732

    Rare opportunity to rent a spacious 3-bedroom unit at Horizons on the Bay featuring beautiful views of the Chesapeake Bay. Enjoy resort-style amenities including a rooftop pool, fitness center, and lending library. Conveniently located near the boardwalk, restaurants, and shopping, this well-maintained building offers coastal living at its finest. Don’t miss this exceptional rental opportunity!

    Pattee McInerney Scott McInerney RE/MAX One

    8501 Bayside Rd, Chesapeake Beach, MD 20732
  • /60

    $499,990

    Sold May 29, 2026

    2819 Glasgow Way, Chesapeake Beach, MD 20732

    • 3 Beds
    • 3 Baths
    • 2,450 Sq Ft
    • Built 1990

    Last Sold Summary

    • $204/SF
    • 3 Days On Market

    Current Estimated Value $496,285

    Last Listing Agent Team Stueckler Keller Williams Flagship

    2819 Glasgow Way, Chesapeake Beach, MD 20732
    • /25

      Est $396,333

      Not Listed For Sale

      5025 Chavez Ln, Chesapeake Beach, MD 20732

      • Built 2008
      5025 Chavez Ln, Chesapeake Beach, MD 20732

      Last Sold Summary

      • 181 Days On Market

  • /3

    $449,990

    Coming Soon
    • 3 Beds
    • 2 Baths
    • 1,856 Sq Ft

    2735 Braeburn Ln, Chesapeake Beach, MD 20732

    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

    2735 Braeburn Ln, Chesapeake Beach, MD 20732
  • /43

    $625,000

    Sold Feb 20, 2026

    2495 Woodland Ct, Chesapeake Beach, MD 20732

    • 4 Beds
    • 3.5 Baths
    • 3,021 Sq Ft
    • Built 1997

    Last Sold Summary

    • $207/SF
    • 11 Days On Market

    Current Estimated Value $624,343

    Last Listing Agent Tohmai Smith RLAH @properties

    2495 Woodland Ct, Chesapeake Beach, MD 20732
    • /68

      Est $619,198

      Not Listed For Sale

      8203 Elm Ln, Chesapeake Beach, MD 20732

      • 4 Beds
      • 3.5 Baths
      • 2,496 Sq Ft
      • Built 2023
      8203 Elm Ln, Chesapeake Beach, MD 20732

      Last Sold Summary

      • 276 Days On Market

  • /47

    $539,900

    $10K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 2,600 Sq Ft

    3693 Brookeside Dr, Chesapeake Beach, MD 20732

    Welcome home to this beautifully updated 5-bedroom, 3.5-bath residence offering the perfect blend of space, style, and everyday comfort in a sought-after neighborhood. Situated within a highly rated school district, this home is ideal for those looking for modern upgrades, functional living spaces, and room to grow. Step inside to find spacious, light-filled living areas and generously sized

    Haley Taylor Real Broker, LLC - Dunkirk

    3693 Brookeside Dr, Chesapeake Beach, MD 20732
  • /9

    $120,000

    Sold Jan 09, 2026

    5150 Lenoir Dr, Chesapeake Beach, MD 20732

    • 3 Beds
    • 1 Bath
    • 825 Sq Ft
    • Built 1945

    Last Sold Summary

    • $145/SF
    • 109 Days On Market

    Current Estimated Value $191,490

    Last Listing Agent tracy dawson O'Brien Realty ERA Powered

    5150 Lenoir Dr, Chesapeake Beach, MD 20732
    • /76

      Est $1,148,845

      Not Listed For Sale

      4485 Bristol Dr, Chesapeake Beach, MD 20732

      • 6 Beds
      • 4.5 Baths
      • 6,037 Sq Ft
      • Built 2022
      4485 Bristol Dr, Chesapeake Beach, MD 20732

      Last Sold Summary

      • 22 Days On Market

  • /29

    $289,900

    $9K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 719 Sq Ft

    6122 6th St, Chesapeake Beach, MD 20732

    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

    6122 6th St, Chesapeake Beach, MD 20732
  • /66

    $571,037

    Sold Mar 16, 2026

    8637 Saint Andrews Dr, Chesapeake Beach, MD 20732

    • 4 Beds
    • 3 Baths
    • 2,436 Sq Ft
    • Built 1986

    Last Sold Summary

    • 3% Below List Price
    • $234/SF
    • 16 Days On Market

    Current Estimated Value $564,551

    Last Listing Agent Lara Owings RE/MAX United Real Estate

    8637 Saint Andrews Dr, Chesapeake Beach, MD 20732
    • /30

      Est $428,179

      Not Listed For Sale

      8343 Autumn Crest Ln Unit 6, Chesapeake Beach, MD 20732

      • 3 Beds
      • 4 Baths
      • 2,218 Sq Ft
      • Built 2010
      8343 Autumn Crest Ln Unit 6, Chesapeake Beach, MD 20732

      Last Sold Summary

      • 3 Days On Market

  • /69

    $777,000

    $5K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,700 Sq Ft

    8229 Bayside Rd, Chesapeake Beach, MD 20732

    Back on the market due to shaky financing! Inspected and READY! Improved price too! Welcome to 8229 Bayside Road, where elevated bayside living meets everyday convenience in the heart of Chesapeake Beach. This beautifully maintained four-bedroom, 3.5-bath residence offers views of the Chesapeake Bay and an unbeatable walkable lifestyle along the water. Spanning four finished levels and serviced

    Farrah Fuchs Redfin Corp

    8229 Bayside Rd, Chesapeake Beach, MD 20732
  • /2

    $13,500

    Sold May 01, 2026

    4115 Calvert Dr, Chesapeake Beach, MD 20732

    • Land
    • 22,215 Sq Ft
    • $26,471 per Acre

    Last Sold Summary

    • 6 Days On Market

    Current Estimated Value $80,500

    Last Listing Agent Katie Mister Keller Williams Select Realtors of Cambridge

    4115 Calvert Dr, Chesapeake Beach, MD 20732
    • /50

      Est $415,270

      Not Listed For Sale

      8424 Clear Spring Dr Unit 4, Chesapeake Beach, MD 20732

      • 4 Beds
      • 3.5 Baths
      • 2,262 Sq Ft
      • Built 2011
      8424 Clear Spring Dr Unit 4, Chesapeake Beach, MD 20732

      Last Sold Summary

      • 4 Days On Market

  • /2

    $38,000

    • Land
    • 1.2 Acres
    • $31,667 per Acre

    0 10th St, Chesapeake Beach, MD 20732

    Unique land opportunity in Chesapeake Beach. Vacant 1.2-acre lot within walking distance to the beach and less than an hour from Washington, DC. Located in the Town’s RC zoning district. Buyer must independently verify permitted uses, zoning, access, utilities, floodplain requirements, and any necessary approvals or permits with the Town, County, and all other applicable authorities. Per the

    Cristhian Huamani Tia Realty. LLC

    0 10th St, Chesapeake Beach, MD 20732
  • /2

    $7,500

    Sold Sep 05, 2025

    6121 5th St, Chesapeake Beach, MD 20732

    • Land
    • 12,196 Sq Ft
    • $26,786 per Acre

    Last Sold Summary

    • 134 Days On Market

    Current Estimated Value $136,344

    Last Listing Agent Team Stueckler Keller Williams Flagship

    6121 5th St, Chesapeake Beach, MD 20732
    • /47

      Est $681,834

      Not Listed For Sale

      3182 Lawrin Ct, Chesapeake Beach, MD 20732

      • 5 Beds
      • 3.5 Baths
      • 3,422 Sq Ft
      • Built 2011
      3182 Lawrin Ct, Chesapeake Beach, MD 20732

      Last Sold Summary

      • 45 Days On Market

  • /53

    $849,900

    $20K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 2,632 Sq Ft

    8047 Windward Key Dr, Chesapeake Beach, MD 20732

    Nestled along the tranquil shores of Chesapeake Beach, this stunning four-bedroom, four-and-a-half-bath waterfront townhome offers 2,632 square feet of thoughtfully designed living space for those who appreciate the beauty of life on the water. Expansive decks on every level provide uninterrupted views, where you can savor gentle breezes and watch local crab boats set out at sunrise. Also, the

    Greg Beckman Coldwell Banker Realty

    8047 Windward Key Dr, Chesapeake Beach, MD 20732
  • /40

    $450,000

    Sold Feb 16, 2026

    2825 Karen Dr, Chesapeake Beach, MD 20732

    • 3 Beds
    • 2.5 Baths
    • 1,608 Sq Ft
    • Built 1986

    Last Sold Summary

    • $280/SF
    • 56 Days On Market

    Current Estimated Value $449,046

    Last Listing Agent Danielle Wilson Real Broker, LLC

    2825 Karen Dr, Chesapeake Beach, MD 20732
    • /47

      Est $625,178

      Not Listed For Sale

      3605 Ponds Wood Dr, Chesapeake Beach, MD 20732

      • 4 Beds
      • 3 Baths
      • 2,897 Sq Ft
      • Built 1984
      3605 Ponds Wood Dr, Chesapeake Beach, MD 20732

      Last Sold Summary

      • 5 Days On Market

  • /127

    $1,050,000

    • 5 Beds
    • 4.5 Baths
    • 3,863 Sq Ft

    3325 Cox Rd, Chesapeake Beach, MD 20732

    This spacious QBH custom built Colonial offers over 5,000 square feet of living space with 5 bedrooms, 4.5 bathrooms, an extra lot that conveys, and no HOA! Thoughtfully updated throughout, this home features a new HVAC system in 2021, brand-new carpet, newer appliances including a dishwasher and refrigerator replaced in 2025, microwave replaced in 2023, plus the washer and dryer. The main level

    Juliet Patterson Samson Properties

    3325 Cox Rd, Chesapeake Beach, MD 20732
  • /21

    $487,500

    Sold May 28, 2026

    8998 Saint Andrews Dr, Chesapeake Beach, MD 20732

    • 4 Beds
    • 2 Baths
    • 1,584 Sq Ft
    • Built 1993

    Last Sold Summary

    • 2% Below List Price
    • $308/SF
    • 12 Days On Market

    Current Estimated Value $492,323

    Last Listing Agent Jana Ritter Ritter Realty, LLC

    8998 Saint Andrews Dr, Chesapeake Beach, MD 20732
    • /18

      Est $460,571

      Not Listed For Sale

      8501 Bayside Rd, Chesapeake Beach, MD 20732

      • 2 Beds
      • 2 Baths
      • 985 Sq Ft
      • Built 2005
      8501 Bayside Rd, Chesapeake Beach, MD 20732

      Last Sold Summary

      • 6 Days On Market

  • /7

    $299,990

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,963 Sq Ft

    5060 Christiana Parran Rd, Chesapeake Beach, MD 20732

    Estate Sale – Subject to final Personal Representative authorization by the Probate Court. Excellent opportunity for investors, flippers, or buyers seeking a renovation project. Situated on a private 1.15-acre lot in a desirable Northern Calvert County location with top rated schools. This 3-bedroom, 2-bath split foyer offers approximately 1,098 finished square feet above grade plus a mostly

    Team Stueckler Keller Williams Flagship

    5060 Christiana Parran Rd, Chesapeake Beach, MD 20732
  • /50

    $800,000

    Sold Apr 07, 2026

    3420 Charing Ct, Chesapeake Beach, MD 20732

    • 4 Beds
    • 3 Baths
    • 3,800 Sq Ft
    • Built 1990

    Last Sold Summary

    • 7% Above List Price
    • $211/SF
    • 3 Days On Market

    Current Estimated Value $776,317

    Last Listing Agent Susan Cleary RE/MAX One

    3420 Charing Ct, Chesapeake Beach, MD 20732
    • /7

      Est $858,532

      Not Listed For Sale

      8501 Bayside Rd, Chesapeake Beach, MD 20732

      • 3 Beds
      • 3 Baths
      • 2,009 Sq Ft
      • Built 2005
      8501 Bayside Rd, Chesapeake Beach, MD 20732

      Last Sold Summary

  • /40

    $555,000

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 2,772 Sq Ft

    8125 Moffat Run, Chesapeake Beach, MD 20732

    If you've been searching for a great value in today's market, this could be the opportunity you've been waiting for! Being sold strictly As-Is, this spacious home offers over 2,700 finished square feet on the upper two levels, plus an additional 1,122 sq. ft. unfinished basement with a rough-in — compare the value to other homes currently on the market. Recent updates include new carpet and LVP

    Gail Nyman RE/MAX United Real Estate

    8125 Moffat Run, Chesapeake Beach, MD 20732
  • /36

    $390,000

    Sold Jan 30, 2026

    4790 Howard Place, Chesapeake Beach, MD 20732

    • 3 Beds
    • 2 Baths
    • 2,164 Sq Ft
    • Built 2002

    Last Sold Summary

    • $180/SF
    • 71 Days On Market

    Current Estimated Value $400,793

    Last Listing Agent Greg Beckman Coldwell Banker Realty

    4790 Howard Place, Chesapeake Beach, MD 20732
    • /35

      Est $429,353

      Not Listed For Sale

      7786 C St, Chesapeake Beach, MD 20732

      • 3 Beds
      • 2.5 Baths
      • 2,068 Sq Ft
      • Built 1987
      7786 C St, Chesapeake Beach, MD 20732

      Last Sold Summary

      • 2 Days On Market

  • /9

    $199,000

    • Land
    • 5.37 Acres
    • $37,058 per Acre

    Lot 30 A, Block 6 18th St, Chesapeake Beach, MD 20732

    Your Private Sanctuary Awaits! Escape to this exclusive, wooded retreat. Imagine building your dream home nestled among mature trees, just moments from the best of the Chesapeake Bay. Whether it's a morning stroll on the boardwalk, a day of crabbing and fishing or an evening of dining and entertainment, everything is at your fingertips. This is more than a lot; it's your gateway to endless

    Robyn Day RE/MAX One

    Lot 30 A, Block 6 18th St, Chesapeake Beach, MD 20732
  • /2

    $434,900

    Sold Apr 24, 2026

    3617 30th St, Chesapeake Beach, MD 20732

    • 4 Beds
    • 2 Baths
    • 1,850 Sq Ft
    • Built 1976

    Last Sold Summary

    • 1% Below List Price
    • $235/SF
    • 55 Days On Market

    Current Estimated Value $438,685

    Last Listing Agent Susan Reinhart Compass

    3617 30th St, Chesapeake Beach, MD 20732
    • /46

      Est $404,623

      Not Listed For Sale

      3316 Silverton Ln, Chesapeake Beach, MD 20732

      • 4 Beds
      • 3 Baths
      • 1,600 Sq Ft
      • Built 2000
      3316 Silverton Ln, Chesapeake Beach, MD 20732

      Last Sold Summary

      • 0 Days On Market

  • /3

    $439,990

    Coming Soon
    • 3 Beds
    • 2 Baths
    • 1,850 Sq Ft

    3721 Willie Ln, Chesapeake Beach, MD 20732

    Tucked away on a private, wooded 1.5-acre lot in a desirable Chesapeake Beach location, this contemporary ranch-style home offers a warm log cabin feel. With approximately 1,850 square feet, this home is priced for an as-is sale and presents a great opportunity to restore it to its former glory with just a little TLC. The open floor plan features a spacious step-down living room with

    Team Stueckler Keller Williams Flagship

    3721 Willie Ln, Chesapeake Beach, MD 20732
  • /34

    $409,000

    Sold May 22, 2026

    2401 Green Leaf Terrace, Chesapeake Beach, MD 20732

    • 4 Beds
    • 2.5 Baths
    • 1,999 Sq Ft
    • Built 2001

    Last Sold Summary

    • 1% Below List Price
    • $205/SF
    • 17 Days On Market

    Current Estimated Value $407,754

    Last Listing Agent Lindsey Burch Samson Properties

    2401 Green Leaf Terrace, Chesapeake Beach, MD 20732
    • /32

      Est $487,703

      Not Listed For Sale

      2720 Braeburn Ln, Chesapeake Beach, MD 20732

      • 4 Beds
      • 2 Baths
      • 2,146 Sq Ft
      • Built 1988
      2720 Braeburn Ln, Chesapeake Beach, MD 20732

      Last Sold Summary

      • 15 Days On Market

  • /5

    $210,000

    Pending
    • Land
    • 20.15 Acres
    • $10,422 per Acre

    2415 Beaver Dam Rd, Chesapeake Beach, MD 20732

    Discover an exceptional opportunity to invest in a sprawling 20.15-acre parcel of land nestled within the prestigious North Chesapeake Beach subdivision. This unique property offers a rare blend of privacy and natural beauty, making it an ideal canvas for your vision, whether it be a luxurious estate, a serene retreat, or a strategic investment for future development. The lot is characterized by

    Samuel J Thomas Hyatt & Company Real Estate LLC

    2415 Beaver Dam Rd, Chesapeake Beach, MD 20732
  • /35

    $480,000

    Sold Sep 19, 2025

    4430 Hallburn Dr, Chesapeake Beach, MD 20732

    • 3 Beds
    • 3 Baths
    • 2,240 Sq Ft
    • Built 1994

    Last Sold Summary

    • $214/SF
    • 4 Days On Market

    Current Estimated Value $478,925

    Last Listing Agent Kimberly Hayes CENTURY 21 New Millennium

    4430 Hallburn Dr, Chesapeake Beach, MD 20732
    • /41

      Est $385,651

      Not Listed For Sale

      3909 Old Bayside Rd, Chesapeake Beach, MD 20732

      • 3 Beds
      • 1 Bath
      • 1,060 Sq Ft
      • Built 1940
      3909 Old Bayside Rd, Chesapeake Beach, MD 20732

      Last Sold Summary

      • 9 Days On Market

Showing Results 41 - 80, Page 2 of 18

How to Buy a Home How to Finance a Home How to Sell a Home