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Chesapeake Beach, MD Homes for Sale with Garage

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    $685,000 Open Fri 5PM - 7PM

    • 4 Beds
    • 3.5 Baths
    • 3,142 Sq Ft

    3683 Middle Ground Ct, Chesapeake Beach, MD 20732

    Situated in the sought-after community of Chesapeake Village, this home offers a lifestyle of convenience, mindful living and community connection! Enjoy a stroll to the front of the community and cross the road to enjoy Brownies Beach at Bayfront Park– a pet-friendly excursion for the entire family. Enjoy the serenity of the water, search for shark teeth, view the beauty of the cliffs and mother

    Agent Photo

    Gene Summers

    Real Broker, LLC

    (443) 332-7997

    3683 Middle Ground Ct, Chesapeake Beach, MD 20732
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    $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
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    $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
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    $630,000

    • 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
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    $449,900

    • 4 Beds
    • 2 Baths
    • 1,704 Sq Ft

    6309 Brookeview Ct, Chesapeake Beach, MD 20732

    This beautiful split level home with lots of space, a large back deck, breakfast nook/ dining room, detached garage, a carport and more. This home highlights the incredible care and maintenance shown over the last 14 years. The roof on the second level replaced in 2014, the main and garage roof replaced in 2025 as well as a new skylight and insulation. Retaining walls replaced in 2017. Brand new

    James Dick Long & Foster Real Estate, Inc.

    6309 Brookeview Ct, Chesapeake Beach, MD 20732
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    $524,700

    • 3 Beds
    • 3 Baths
    • 1,952 Sq Ft

    3305 Chesapeake Beach Rd, Chesapeake Beach, MD 20732

    Welcome to this expansive 3BR, 3BA split-foyer in Chesapeake Beach! The light-filled upper level boasts a seamless flow between the living area and an updated kitchen with granite countertops and stainless steel appliances. Step into the stunning sunroom off the kitchen—your private sanctuary for morning coffee with views of the fully fenced-in backyard that backs to trees! The finished lower

    Mike Benton Home Towne Real Estate

    3305 Chesapeake Beach Rd, Chesapeake Beach, MD 20732
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    $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
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    $735,000

    • 4 Beds
    • 3.5 Baths
    • 3,300 Sq Ft

    3221 Smiths Retreat, Chesapeake Beach, MD 20732

    Tucked away on a quiet cul-de-sac in sought-after Chesapeake Beach, this home offers a comfortable blend of space, function, and location—just a 3-minute drive to the Chesapeake Bay. Enjoy easy access to waterfront dining, local restaurants, and entertainment, all while coming home to a peaceful setting. The property features 5 bedrooms, 3.5 bathrooms, and a custom-built gunite pool. A covered

    Danny Martin Keller Williams Flagship

    3221 Smiths Retreat, Chesapeake Beach, MD 20732
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    $869,900

    • 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 townhouse offers 2,632 square feet of thoughtfully designed living space for those who appreciate the beauty of life by 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, this

    Greg Beckman Coldwell Banker Realty

    8047 Windward Key Dr, Chesapeake Beach, MD 20732
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    $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
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    $850,000

    • 4 Beds
    • 5 Baths
    • 3,049 Sq Ft

    8074 Windward Key Dr, Chesapeake Beach, MD 20732

    Welcome to 8074 Windward Key Drive – a stunning four-level coastal townhome offering sweeping double sided water views, stylish updates, and exceptional outdoor living on every floor! Perfectly situated in the sought-after Windward Key community, this residence delivers the best of Chesapeake Bay living with resort-style amenities and thoughtful modern design throughout. Step inside to a bright,

    Pattee McInerney Scott McInerney RE/MAX One

    8074 Windward Key Dr, Chesapeake Beach, MD 20732
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    $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
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    $220,000

    • 3 Beds
    • 2 Baths
    • 2,597 Sq Ft

    6231 8th St, Chesapeake Beach, MD 20732

    This property is being sold as-is and is perfect for investors, flippers, or buyers looking for a renovation opportunity. With solid bones and endless potential, this home is a blank canvas ready for your vision. Whether you’re looking to fix and flip, hold as a rental, or bring new life to a great location—this is the one. Cash, hard money, or renovation loan preferred. Don’t miss this chance to

    Teairra Jones Samson Properties

    6231 8th St, Chesapeake Beach, MD 20732
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    $525,000 Coming Soon

    • 3 Beds
    • 3 Baths
    • 1,756 Sq Ft

    5910 Karen Ct, Chesapeake Beach, MD 20732

    Lakefront Community Living Meets Modern Country Comfort!Escape to the best of country living in this stunning 3 bedroom, 3 bathroom Split-Level home, perfectly situated on an over 1 -acre cul-de-sac lot in the highly sought-after, lake-privileged community of Lake Karylbrook. Whether you are an avid angler or a nature lover, you’ll enjoy exclusive access to a private lake renowned for some of

    Thomas Herritt Samson Properties

    5910 Karen Ct, Chesapeake Beach, MD 20732
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    $620,000 Coming Soon

    • 4 Beds
    • 2.5 Baths
    • 2,274 Sq Ft

    2637 Richfield Ln, Chesapeake Beach, MD 20732

    Welcome to this beautifully maintained 2-story Colonial located in private, sought-after community of Richfield Station in Chesapeake Beach. Offering 4 spacious bedrooms and 2.5 bathrooms, this home sits on just over 1/3 acre and includes a two-car garage and fully fenced backyard. The oversized Trex deck is perfect for outdoor enjoyment and overlooks the peaceful yard shaded by mature trees.

    Vanessa Gill O'Brien Realty ERA Powered

    2637 Richfield Ln, Chesapeake Beach, MD 20732
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    $719,000 Coming Soon

    • 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
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    $495,000 Open Sun 12PM - 3PM

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

    8998 Saint Andrews Dr, Chesapeake Beach, MD 20732

    Coming soon! Open House 04/19/2026 from 12noon-3pm.Experience refined coastal living in this impeccably maintained 4-bedroom, 2-bath residence, gracefully situated on a private 2-acre lot in the prestigious Highlands community of Chesapeake Beach. Tucked away on a quiet cul-de-sac, this exceptional property offers a rare combination of tranquility, space, and understated elegance—all with a

    Jana Ritter Ritter Realty, LLC

    8998 Saint Andrews Dr, Chesapeake Beach, MD 20732
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    $568,000 Coming Soon

    • 5 Beds
    • 3 Baths
    • 2,800 Sq Ft

    2914 Tartan Ln, Chesapeake Beach, MD 20732

    Photos Coming 4/ 21 ** MANY Updates and Upgrades to this Inviting Cape Cod * Home has been entirely Re-Modeled since 2016 including but not limited to: All new Double - Hung Windows 2016 * New Doors 2016 * Finished Lower Level with 2nd Full Kitchen and Island * Porcelain "wood-look" Tile on Main Level * Large Primary Suite above the garage with Dual WICs and Primary BA with Double vanities * New

    Lara Owings RE/MAX Realty Group

    2914 Tartan Ln, Chesapeake Beach, MD 20732
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    $349,000 Coming Soon

    • 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
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    $650,000 Open House 4/25

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

    2269 Sansbury Dr, Chesapeake Beach, MD 20732

    5 bedroom 3.5 bath home located in the sought-after Richfield Station neighborhood, you’ll have access to fantastic community amenities such as playgrounds, walking trails, sports courts, and more — all in a friendly, well-kept environment close to shopping, schools, and commuter routes. Don’t miss this opportunity to make this wonderful house your new home!Pictures will be coming soon !!!

    Theresa Mills Samson Properties

    2269 Sansbury Dr, Chesapeake Beach, MD 20732

Home Trends in Chesapeake Beach, MD

Housing Trends

Median Sale Price
$451,315
Median Single Family Sale Price
$499,990
Median Townhouse Sale Price
$408,950
Median 2 Bedroom Sale Price
$475,000
Median 1 Bedroom Sale Price
$349,000
Average Price Per Sq Ft
$216
Number of Homes for Sale
36
Last 12 months Home Sales
130
Months of Supply
3.30
Median List Price
$458,450
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
4%
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