17

Chesapeake Beach, MD Homes for Sale with Garage

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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
  • /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
  • /53

    $849,900

    Open Fri 6:30PM - 8:30PM $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
  • /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
  • /2

    $190,000

    • 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
  • /40

    $385,000

    Open Sat 1PM - 3PM Coming Soon
    • 3 Beds
    • 2.5 Baths
    • 2,641 Sq Ft

    2243 Ivy Ln, Chesapeake Beach, MD 20732

    This bright, spacious 2,600 sq. ft. townhome in Chesapeake Beach's desirable Richfield Station features 3 bedrooms, 2.5 baths, and a 1-car garage plus assigned space. Enjoy new HVAC and appliances, plus neighborhood walking trails, a playground, and basketball court—just a short distance to the Chesapeake Beach boardwalk and dining!

    Tresha Davis Coldwell Banker Realty

    2243 Ivy Ln, Chesapeake Beach, MD 20732
  • /30

    $849,900

    $49K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 2,876 Sq Ft

    8054 Windward Key Dr, Chesapeake Beach, MD 20732

    Experience an elevated waterfront lifestyle in the coveted Windward Key community, ideally positioned along the shores of the Chesapeake Bay in the heart of Chesapeake Beach. This exceptional four-level townhome blends refined design with water views, offering 3 bedrooms, 4 full baths, and 1 half bath across thoughtfully designed living spaces. Sunlight pours through expansive windows,

    Doug Smith RE/MAX Realty Group

    8054 Windward Key Dr, Chesapeake Beach, MD 20732
  • /39

    $575,000

    $25K PRICE DROP
    • 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, with bay views right from your deck. 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,

    Greg Beckman Coldwell Banker Realty

    8236 Bayside Rd, Chesapeake Beach, MD 20732
  • /2

    $1,300,000

    Coming Soon
    • 4 Beds
    • 3 Baths
    • 2,598 Sq Ft

    4011 27th St, Chesapeake Beach, MD 20732

    Everything you want in a true Chesapeake Bay waterfront property is right here. Nestled on a rare, oversized double corner lot in Chesapeake Beach, this one-of-a-kind historic waterfront estate offers unmatched charm, versatility, and income-producing potential. With a location that simply cannot be duplicated, this property delivers the ultimate coastal lifestyle just 35 minutes from Washington,

    Sarah Reynolds Keller Williams Realty

    4011 27th St, Chesapeake Beach, MD 20732
  • /34

    $824,900

    • 4 Beds
    • 4.5 Baths
    • 2,950 Sq Ft

    8076 Windward Key Dr, Chesapeake Beach, MD 20732

    COASTAL LUXURY MEETS EVERYDAY VACATION LIVING in Windward Key on the Chesapeake Bay. Experience the ultimate waterfront lifestyle in this four-level townhome nestled in the sought-after Windward Key community in the heart of Chesapeake Beach. Whether you are searching for a full-time residence or the perfect weekend retreat, this exceptional home offers resort-style living with water views and

    Doug Smith RE/MAX Realty Group

    8076 Windward Key Dr, Chesapeake Beach, MD 20732
  • /2

    $619,900

    Coming Soon
    • 4 Beds
    • 2.5 Baths
    • 2,276 Sq Ft

    2630 Richfield Ln, Chesapeake Beach, MD 20732

    COMING SOON! Welcome to 2630 Richfield Lane in Chesapeake Beach! This beautiful 4-bedroom, 2 full bath, 1 half bath home offers a fresh, updated feel with plenty of space to make your own. The main level features luxury vinyl plank flooring throughout main level, fresh paint, and a bright, functional layout perfect for everyday living and entertaining. The kitchen offers a spacious island, great

    Jenna Bare-Anderkovitch CENTURY 21 New Millennium

    2630 Richfield Ln, 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
  • /70

    $350,000

    $9K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,600 Sq Ft

    2183 Ivy Ln Unit 4, Chesapeake Beach, MD 20732

    Welcome to 2183 Ivy Lane in Chesapeake Beach, MD, where comfort, convenience, and low-maintenance living come together in one beautifully updated home, now with incredible buyer incentives! The seller is offering 3% closing cost assistance, providing exceptional value and added flexibility for buyers. This sought-after “2 over 2” condo floor plan offers the spacious feel of a townhome while

    DJ Hayes RLAH @properties

    2183 Ivy Ln Unit 4, Chesapeake Beach, MD 20732
  • /65

    $1,099,000

    $26K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 6,659 Sq Ft

    3640 Estelle Ct, Chesapeake Beach, MD 20732

    ***VA Assumable @ 2.375%! 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

    Heather Hall Hyatt & Company Real Estate LLC

    3640 Estelle Ct, Chesapeake Beach, MD 20732
  • /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
  • /2

    $549,900

    Coming Soon
    • 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
  • /55

    $599,000

    • 4 Beds
    • 3 Baths
    • 2,196 Sq Ft

    4111 Pinewood Terrace, Chesapeake Beach, MD 20732

    Move-in ready and offering exceptional space throughout, this classic split-level home delivers a flexible layout designed for comfortable living and everyday functionality. Featuring three attached garage spaces including a two-car front-entry garage and an additional rear garage, this home is ideal for those who are mechanically inclined, need extra storage, or want the freedom to create a

    Tina Marie Biggs EXP Realty, LLC

    4111 Pinewood Terrace, Chesapeake Beach, MD 20732

Home Prices in Chesapeake Beach, MD

Home Price Trends

Median Sale Price
$460,250
Median Single Family Sale Price
$496,495
Median Townhouse Sale Price
$412,500
Median 2 Bedroom Sale Price
$462,450
Average Price Per Sq Ft
$225
Number of Homes for Sale
30
Last 12 months Home Sales
140
Months of Supply
2.60
Median List Price
$463,500
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
6%
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