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Chesapeake Beach, MD Homes for Sale with Pool

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  • /50

    $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. Because of

    Greg Beckman Coldwell Banker Realty

    8047 Windward Key Dr, Chesapeake Beach, MD 20732
  • /41

    $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
  • /49

    $570,000 Coming Soon

    • 4 Beds
    • 2.5 Baths
    • 2,006 Sq Ft

    3713 28th St, Chesapeake Beach, MD 20732

    Welcome to your dream home in the heart of beautiful Chesapeake Beach! This charming 4-bedroom, 2.5-bath ranch-style home offers comfortable single-level living just five blocks from the sparkling shores of the Chesapeake Bay. Perfectly situated in a quiet neighborhood, this home blends coastal charm with everyday convenience. Step inside to find a spacious and inviting floor plan featuring a

    Richard Polish Sid Sells Maryland Realty

    3713 28th St, Chesapeake Beach, MD 20732
  • /15

    $355,000 Open Sun 1PM - 4PM

    • 1 Bed
    • 1.5 Baths
    • 862 Sq Ft

    8501 Bayside Rd, Chesapeake Beach, MD 20732

    Horizons On The Bay is a gated seaside community, with too many amenities to list! Relax at the rooftop pool, enjoy a meal at picnic point, work out along the bay in your new gym, or simply watch the tide from the pier. Walking distance to beaches, boardwalks, shops, dining, entertainment, and more! This unit has fantastic views from the deck. Features a 1 bedroom 1.5 bath. This community has

    Valerie Henderson Berkshire Hathaway HomeServices PenFed Realty

    8501 Bayside Rd, Chesapeake Beach, MD 20732
  • /102

    $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
  • /30

    $450,000

    • 2 Beds
    • 2 Baths
    • 984 Sq Ft

    8501 Bayside Rd, Chesapeake Beach, MD 20732

    Stunning Chesapeake Bay panoramic water views from this luxury condominium. Features two bedrooms and 2 full baths kitchen with breakfast bar and a large balcony overlooking the Bay. Enjoy watching the Osprey, Bald Eagles, Dolphins, Sailboats, and other water sports . Wake up to the gorgeous sunrise, over the Bay, from the primary bedroom that has access to the balcony. The Primary suite has a

    Paulette Ladas RLAH @properties

    8501 Bayside Rd, Chesapeake Beach, MD 20732

Home Trends in Chesapeake Beach, MD

Housing Trends

Median Sale Price
$450,000
Median Single Family Sale Price
$493,000
Median Townhouse Sale Price
$409,000
Median 2 Bedroom Sale Price
$462,500
Median 1 Bedroom Sale Price
$355,000
Average Price Per Sq Ft
$219
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
2%
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