25

Chesapeake Beach, MD Houses for Sale

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  • /16

    $699,999 New Construction

    • 4 Beds
    • 2.5 Baths
    • 1,802 Sq Ft

    8314 Bayside Rd, Chesapeake Beach, MD 20732

    TO BE BUILT HOME in the sought-after Chesapeake Beach community. This exceptional NEW CONSTRUCTION opportunity co-marketed with Schaefer Homes allows you to build your dream home on a prime lot with views of the Chesapeake Bay. The featured Eastport model blends Colonial and Coastal architectural elements with an open-concept layout. The main level offers a spacious family room flowing seamlessly

    Erin Roccapriore JPAR Real Estate Professionals

    8314 Bayside Rd, Chesapeake Beach, MD 20732
  • /49

    $625,000

    • 3 Beds
    • 3.5 Baths
    • 3,058 Sq Ft

    3238 Rector Lookout, Chesapeake Beach, MD 20732

    Welcome to 3238 Rector Lookout in the sought-after community of Chesapeake Beach, MD 20732—a beautifully maintained single-family home offering space, comfort, and versatile living areas throughout. This impressive home features an attached two-car garage and a thoughtfully designed floor plan ideal for both everyday living and entertaining. The main level boasts a bright living room and formal

    Tig Wright Redfin Corp

    3238 Rector Lookout, Chesapeake Beach, MD 20732
  • /48

    $625,000

    • 4 Beds
    • 4.5 Baths
    • 3,616 Sq Ft

    8499 Saint Andrews Dr, Chesapeake Beach, MD 20732

    Beautifully customized home featuring a stunning kitchen with abundant custom cabinetry, sparkling black granite countertops, and ample seating. Brazilian cherry hardwood floors add warmth and elegance throughout the main living areas. The spacious great room offers vaulted ceilings and a cozy propane fireplace. The private owner’s suite features vaulted ceilings, a walk-in closet, and convenient

    Ryan Hutchins Hutchins Properties

    8499 Saint Andrews Dr, Chesapeake Beach, MD 20732
  • /43

    $649,990 Coming Soon

    • 4 Beds
    • 3.5 Baths
    • 2,440 Sq Ft

    2465 Woodland Ct, Chesapeake Beach, MD 20732

    BEAUTIFUL COLONIAL HOME IN RICHFIELD STATION!!! Beautifully Landscaped!!! Nice level lot! Crown Molding, 9' Ceilings and dimmer switches on lighting throughout * this Beautiful Home has been very well maintained and updated! Entrance foyer * Spacious Living Room * Separate Dining Room with hardwood flooring and bay window * Updated Kitchen with LVT flooring, Island/Breakfast Bar, Pantry, Ceramic

    Debbie Balderson O'Brien Realty ERA Powered

    2465 Woodland Ct, Chesapeake Beach, MD 20732
  • /53

    $570,000 Open Sat 11AM - 1PM

    • 4 Beds
    • 3 Baths
    • 3,178 Sq Ft

    6311 Deerbrooke Ct, Chesapeake Beach, MD 20732

    Welcome to 6311 Deerbrooke Ct in Chesapeake Beach—a beautifully maintained split-level home offering the perfect blend of comfort, space, and versatility! Situated on a generous 0.96-acre lot, this property features 4 spacious bedrooms and 3 full bathrooms, ideal for families of all sizes.A standout feature is the private in-law suite, perfect for multi-generational living, guest

    Marizel Brewington JPAR Real Estate Professionals

    6311 Deerbrooke Ct, Chesapeake Beach, MD 20732
  • /88

    $640,000

    • 5 Beds
    • 3.5 Baths
    • 2,636 Sq Ft

    2269 Sansbury Dr, Chesapeake Beach, MD 20732

    This 5-bedroom, 3.5-bath home is located in the highly sought-after Richfield Station neighborhood. Residents enjoy access to exceptional community amenities, including playgrounds, scenic walking trails, sports courts, and more—all within a welcoming, well-maintained setting. Conveniently situated near shopping, schools, and major commuter routes, this home offers both comfort and accessibility.

    Theresa Mills Samson Properties

    2269 Sansbury Dr, Chesapeake Beach, MD 20732
  • /79

    $719,000

    • 5 Beds
    • 3.5 Baths
    • 4,210 Sq Ft

    3436 Hill Gail Dr, Chesapeake Beach, MD 20732

    This beautifully maintained home is located in the highly sought-after Chesapeake Village community! The spacious primary suite is a true retreat, featuring two walk-in closets, a luxurious soaking tub, separate tiled shower, and double vanities. The heart of the home is the stunning kitchen, complete with granite countertops, a large center island, stylish, tiled backsplash, built-in microwave,

    Team Stueckler Keller Williams Flagship

    3436 Hill Gail Dr, Chesapeake Beach, MD 20732
  • /72

    $699,000

    • 4 Beds
    • 3.5 Baths
    • 2,856 Sq Ft

    2944 Heritage Dr, Chesapeake Beach, MD 20732

    Welcome to 2944 Heritage Dr., Chesapeake Beach, MD 20732. This Colonial features a finished basement, fenced yard, and brand-new composite deck. It sits on a quiet cul-de-sac in sought-after Heritage Woods, where newer construction, thoughtful upgrades, and coastal lifestyle convenience come together in one exceptional home. This residence offers an open floor plan, upgraded kitchen, and turnkey

    Tom Walsh RE/MAX One

    2944 Heritage Dr, Chesapeake Beach, MD 20732
  • /3

    $530,000

    • 5 Beds
    • 3 Baths
    • 1,872 Sq Ft

    3907 16th St, Chesapeake Beach, MD 20732

    5 bedrooms, 3 full bathrooms, 4 car garage, 3 attics, no HOA, parking for RV's, boats, trailers, large deck, near boardwalk and beach, near grocery store and restaurants, near casino, City water and sewer, refurbishing completed years ago, current rental.

    Pamela Debnam Houwzer, LLC

    3907 16th St, Chesapeake Beach, MD 20732
  • /28

    $499,900 Open Sat 12PM - 2PM

    • 4 Beds
    • 3 Baths
    • 1,925 Sq Ft

    7601 I St, Chesapeake Beach, MD 20732

    Welcome to this meticulously maintained home in Chesapeake Beach, offering nearly 2K sqft of living space on over an acre of beautifully landscaped land, and access to Bayfront Park! This property stands out with its oversized and freshly painted front porch, a stone façade, expansive driveway with ample parking, and no HOA - perfect for RVs, boats, and all your toys. The outdoor space is a true

    Delaney Clarke RE/MAX United Real Estate

    7601 I St, Chesapeake Beach, MD 20732
  • /2

    $485,000 Open Sat 10AM - 12PM

    • 4 Beds
    • 2 Baths
    • 1,344 Sq Ft

    3817 Bayview Dr, Chesapeake Beach, MD 20732

    Beautiful rancher in sought-after Willows Colony offering the perfect blend of comfort, updates, and Chesapeake Bay charm! This well-maintained home features a gorgeous kitchen with granite countertops, stainless steel energy-efficient appliances, and maple cabinetry. The upgraded bathrooms include newer vanities, ceramic tile, and radiant heat for added comfort. Major exterior and system updates

    Amber Mabry Samson Properties

    3817 Bayview Dr, Chesapeake Beach, MD 20732
  • /35

    $525,000

    • 3 Beds
    • 3.5 Baths
    • 2,156 Sq Ft

    3905 26th St, Chesapeake Beach, MD 20732

    Welcome to 3905 26th Street — a 3-bedroom, 3 full and 1 half bath home set just moments from the Chesapeake Bay in the heart of Chesapeake Beach, where a flexible layout and multiple suite options come together in a setting that feels both comfortable and connected to the water. The main level opens into a series of well-defined living spaces, including a large living room and a separate family

    Carolyn Young Samson Properties

    3905 26th St, Chesapeake Beach, MD 20732
  • /26

    $330,000

    • 3 Beds
    • 3 Baths
    • 960 Sq Ft

    4037 1st St, Chesapeake Beach, MD 20732

    3-bedroom, 3-bath home with a renovated interior and hardwood flooring throughout. Functional layout with updated finishes, including stainless steel appliances. Includes a sunroom addition that provides additional living space, along with a fenced-in yard offering privacy and usability. Solid overall layout with good interior and exterior features.

    Ben Garner Cummings & Co. Realtors

    4037 1st St, Chesapeake Beach, MD 20732
  • /35

    $439,000

    • 3 Beds
    • 1.5 Baths
    • 1,164 Sq Ft

    3908 Old Bayside Rd, Chesapeake Beach, MD 20732

    Turnkey coastal charmer in the heart of Chesapeake Beach! This fully renovated 3-bed, 1.5 bath home offers modern living just steps from Brownie’s Beach Natural Area with seasonal Chesapeake Bay views and that private boardwalk feel you love. Step inside to an open-concept layout with vaulted ceilings in the kitchen and primary bedroom. The cozy kitchen shines with all-new Maytag appliances and

    Heather Hall Hyatt & Company Real Estate LLC

    3908 Old Bayside Rd, Chesapeake Beach, MD 20732
  • /69

    $777,000

    • 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
  • /39

    $595,500

    • 4 Beds
    • 2 Baths
    • 2,857 Sq Ft

    8236 Bayside Rd, Chesapeake Beach, MD 20732

    Beach living at its best in the heart of Chesapeake Beach! Embrace the coastal lifestyle in this spacious home offering over 2,800 square feet, four well-appointed bedrooms, and the convenience of an elevator. The property also features a fully fenced yard, a two-car garage, and a versatile detached outbuilding that can easily serve as a gym, workshop, office, guest space, creative studio or

    Greg Beckman Coldwell Banker Realty

    8236 Bayside Rd, Chesapeake Beach, MD 20732
  • /53

    $349,000

    • 2 Beds
    • 1 Bath
    • 882 Sq Ft

    8329 Bayside Rd, Chesapeake Beach, MD 20732

    ****CHESAPEAKE BAY VIEWS*** Welcome to this charming 2-bedroom, 1-bath bungalow nestled in the intimate waterfront community of Baycrest in Chesapeake Beach. Completely renovated in 2025, this home offers the peace of mind of all-new systems and finishes while maintaining its coastal charm. Perfectly blending comfort and coastal charm, this home offers an easygoing lifestyle just steps from the

    Lynn Knapp Long & Foster Real Estate, Inc.

    8329 Bayside Rd, Chesapeake Beach, MD 20732
  • /40

    $349,986

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    6130 4th St, Chesapeake Beach, MD 20732

    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

    6130 4th St, Chesapeake Beach, MD 20732
  • /19

    $379,950

    • 2 Beds
    • 1 Bath
    • 828 Sq Ft

    5130 Rosemary Dr, Chesapeake Beach, MD 20732

    Beach cottage in a small, private, Chesapeake front community with bay access where you can swim, sunbathe and hunt for shark's teeth and fossils. This community is tucked along the shore of The Chesapeake Bay. The cottage has a fireplace that adds to its charm. Plentiful driveway (2) parking and a yard with a treed view. New HVAC system 2026. Chesapeake Beach boasts lots of activities within a

    Ronald Watson Flag Real Estate Inc.

    5130 Rosemary Dr, Chesapeake Beach, MD 20732
  • /42

    $429,990

    • 3 Beds
    • 2 Baths
    • 1,854 Sq Ft

    3632 Brookeside Dr, Chesapeake Beach, MD 20732

    Great price for this 4-Level home with a total of 2,482 sf -- including 600+ sf of unfinished storage space on bottom level! Almost one acre (.81) of land surrounded by mature trees and in great Northern Calvert location of top-rated schools. Kitchen has stainless steel appliances, and has real wood cabinets that a new owner could paint to easily update! Kitchen has a pantry, a breakfast bar and

    Conor Stueckler Keller Williams Flagship

    3632 Brookeside Dr, Chesapeake Beach, MD 20732
  • /2

    $260,000

    • 2 Beds
    • 1 Bath
    • 1,364 Sq Ft

    3728 Chesapeake Beach Rd, Chesapeake Beach, MD 20732

    Don't miss out on this fantastic chance to acquire a delightful 2-bedroom, 1-bath rambler situated merely three blocks from the stunning Chesapeake Bay and the beach. Renovated in 1989, this residence boasts a roomy, flat, fenced yard that is perfect for unwinding and enjoying outdoor pursuits. With two spacious bedrooms and the added advantage of being zoned for both residential and town

    Chrystal Dove CENTURY 21 New Millennium

    3728 Chesapeake Beach Rd, Chesapeake Beach, MD 20732
  • /15

    $423,700

    • 5 Beds
    • 3 Baths
    • 1,868 Sq Ft

    6572 12th St, Chesapeake Beach, MD 20732

    This 5-bedroom, 3-bathroom home is ready for new owners! Located on a quiet cul-de-sac with a huge fenced-in backyard and a spacious deck off the kitchen. Convenient Chesapeake Beach location, close to the Chesapeake Bay, and all the amenities that Chesapeake Beach has to offer! Bayfront Park, shopping, restaurants, the water park, ballparks, playgrounds, community center, marina, boardwalks, and

    Mike Benton Home Towne Real Estate

    6572 12th St, Chesapeake Beach, MD 20732
  • /65

    $1,125,000 Coming Soon

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

    3640 Estelle Ct, Chesapeake Beach, MD 20732

    Welcome to 3640 Estelle Ct—where space, function, and location come together on 2.25 private acres in Chesapeake Beach. This thoughtfully designed home offers flexibility for today’s lifestyle, featuring a dedicated main-level home office and a potential main-level bedroom—ideal for guests or multi-generational living. The open-concept layout flows into a stunning two-story family room and

    Heather Hall Hyatt & Company Real Estate LLC

    3640 Estelle Ct, Chesapeake Beach, MD 20732
  • /36

    $349,000

    • 4 Beds
    • 2.5 Baths
    • 1,824 Sq Ft

    3815 13th St, Chesapeake Beach, MD 20732

    Welcome to 3815 13th Street, a rare opportunity to own a 3-bedroom, 2.5-bath home in the highly desirable Chesapeake Estates—one of the final neighborhoods in Chesapeake Beach with no HOA. Perfectly positioned in a prime coastal setting, this property offers an unmatched lifestyle just a short walk from the community beach, boardwalk, marinas, waterfront dining, local shops, and endless

    Matthew Burgan Infinitas Realty Group

    3815 13th St, Chesapeake Beach, MD 20732
  • /2

    $405,000 Coming Soon

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

    6337 Dory Ct, Chesapeake Beach, MD 20732

    Genna Fleming Hyatt & Company Real Estate LLC

    6337 Dory Ct, Chesapeake Beach, MD 20732

Why Live in Chesapeake Beach

Chesapeake Beach, Maryland, is a growing destination on the shores of the Chesapeake Bay, offering a mix of residential and commercial development. The town features a variety of home styles, including contemporary townhouses, pastel-colored bungalows, and Dutch colonial split-levels, primarily situated on small lots. The northern end of Chesapeake Beach is more densely developed, while the southern end remains largely residential. The local schools, part of the Calvert County School District, are highly rated, with Beach Elementary, Windy Hill Middle, and Northern High all earning commendable scores and recognition for their teaching staff and green initiatives.

Residents enjoy private beach access at Brownie's Beach, a popular spot for picnics and searching for sharks' teeth and sea glass. Veterans Memorial Park offers stunning views of the Bay and a place to honor America's veterans. Fishing Creek provides freshwater angling opportunities and access to the Chesapeake Beach Railway Trail, which is set to offer 28 miles of scenic greenway across Southern Maryland once completed. Currently, sections of the Trail allow for biking through natural habitats.

Dining options in Chesapeake Beach are plentiful, with a recent boom in restaurants. Baia Coastal Italian Kitchen and Wine Bar offers bay views and Italian seafood dishes, while Abners Crab House is known for its soft-shell crab sandwich. Residents also benefit from Roland's Supermarket, which provides delivery and online ordering. With its active lifestyle, exciting amenities, and valuable investments, Chesapeake Beach is becoming a cultural hub on the upper Chesapeake Bay.

Home Trends in Chesapeake Beach, MD

Housing Trends

Median Sale Price
$450,000
Median Single Family Sale Price
$496,450
Median Townhouse Sale Price
$380,000
Median 2 Bedroom Sale Price
$475,000
Average Price Per Sq Ft
$215
Number of Homes for Sale
35
Last 12 months Home Sales
131
Months of Supply
3.20
Median List Price
$450,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
4%
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