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Colonial Homes for Sale in Chesapeake Beach, MD

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  • /60

    $739,900

    • 3 Beds
    • 2.5 Baths
    • 1,732 Sq Ft

    8337 Bay Crest Ct, Chesapeake Beach, MD 20732

    Rich solid bamboo flooring flows throughout the main living areas, while replacement windows maximize the breathtaking Bay views. The remodeled gourmet kitchen features quartz countertops, stainless steel appliances, and opens to a full-width waterfront deck—perfect for morning coffee, outdoor dining, or simply watching the boats pass by. The spacious family room also opens onto a private

    Agent Photo

    Gail Nyman

    RE/MAX United Real Estate

    8337 Bay Crest Ct, Chesapeake Beach, MD 20732
  • /40

    $650,000

    Coming Soon
    • 4 Beds
    • 3.5 Baths
    • 4,214 Sq Ft

    8475 Saint Andrews Dr, Chesapeake Beach, MD 20732

    Welcome to 8475 Saint Andrews Drive! This lovely home offers tons of space, and is the largest home in the neighborhood! The main level offers a living room, formal dining room, kitchen with granite countertops and stainless steel appliances, a breakfast room, a huge family room, and an expansive back deck. The 2nd level offers a palatial primary suite, including a full primary bathroom with a

    Agent Photo

    Andrew Cerrito

    Cerrito Realty, LLC

    8475 Saint Andrews Dr, Chesapeake Beach, MD 20732
  • /30

    $400,000

    Open Sun 11AM - 1PM
    • 4 Beds
    • 3 Baths
    • 1,876 Sq Ft

    8418 Clear Spring Dr Unit 1, Chesapeake Beach, MD 20732

    Welcome to this bright and airy end-unit townhome in the Richfield Station community of Chesapeake Beach. Sun-filled living spaces include a beautiful kitchen with an island and stainless-steel appliances that opens to the dining area and a spacious living room. The home backs onto serene, mature trees, filling the interior with abundant natural light through multiple windows and doors that lead

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    Gil Poudrier

    TTR Sotheby's International Realty

    8418 Clear Spring Dr Unit 1, Chesapeake Beach, MD 20732
  • /29

    $475,000

    • 4 Beds
    • 4 Baths
    • 2,074 Sq Ft

    3610 Glouster Dr, North Beach, MD 20714

    Experience net-zero living in this spacious three-level townhome located in the desirable San Francisco by the Bay community. Owned rooftop solar panels, energy-efficient design, and a smart thermostat have enabled nearly three years of zero electric bills. The open-concept main level showcases hardwood flooring, abundant natural light, granite countertops, center island, stone backsplash,

    Agent Photo

    Din Khaled

    Houwzer, LLC

    3610 Glouster Dr, North Beach, MD 20714
  • /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
  • /68

    $650,000

    Open Fri 4PM - 6PM $30K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 3,570 Sq Ft

    2425 Harrison Ct, Chesapeake Beach, MD 20732

    OPEN HOUSE FRIDAY, AUGUST 21st, 4 pm-6 pmASSUMABLE 2.25% VA LOAN AVAILABLE (Qualified Buyers – Inquire for Details)Welcome to one of the LARGEST & extensively updated homes in Richfield Station—3500 SF sitting on .69 acres where modern upgrades, spacious living, privacy and the coveted Chesapeake Beach lifestyle come together in perfect harmony.Refreshed for 2026, with NEW

    Dorothy Bistransin Redfin Corp

    2425 Harrison Ct, Chesapeake Beach, MD 20732
  • /38

    $599,900

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

    2630 Richfield Ln, Chesapeake Beach, MD 20732

    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 cabinet

    Jenna Bare-Anderkovitch CENTURY 21 New Millennium

    2630 Richfield Ln, Chesapeake Beach, MD 20732
  • /47

    $539,900

    Open Sat 11AM - 1PM
    • 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

    Haley Taylor Real Broker, LLC - Dunkirk

    3693 Brookeside Dr, Chesapeake Beach, MD 20732
  • /21

    $1,299,000

    • 6 Beds
    • 4.5 Baths
    • 6,037 Sq Ft

    4485 Bristol Dr, Chesapeake Beach, MD 20732

    Welcome Home to an Extraordinary Private Estate in Owens Soper EstatesHidden beyond a long, winding private driveway that gracefully meanders through 57 breathtaking acres of pristine woodland, this exceptional custom Colonial is the definition of luxury, privacy, and timeless elegance. Nestled within the prestigious Owens Soper Estates of Northern Calvert County, this is far more than a

    Chrystal Dove CENTURY 21 New Millennium

    4485 Bristol Dr, Chesapeake Beach, MD 20732
  • /64

    $624,700

    • 4 Beds
    • 4.5 Baths
    • 3,240 Sq Ft

    4325 Willows Rd, Chesapeake Beach, MD 20732

    Welcome home to this spacious colonial in the sought-after, water-privileged community of Willows Colony. Featuring 4 bedrooms, 4.5 bathrooms, and hardwood floors throughout, this home offers plenty of room and a flexible unfinished basement with a workshop. Outside, you can relax on the front porch or enjoy the private, wooded backyard with a deck, patio, fish pond, shed, and 2-car garage. Best

    Mike Benton Home Towne Real Estate

    4325 Willows Rd, Chesapeake Beach, MD 20732
  • /2

    $650,000

    • 5 Beds
    • 3.5 Baths
    • 3,060 Sq Ft

    2643 Richfield Ln, Chesapeake Beach, MD 20732

    Welcome to 2643 Richfield Lane! If you've been looking for a home with plenty of space, thoughtful updates, and room for everyone, this is one you won't want to miss. This beautifully maintained 5-bedroom Colonial offers the perfect blend of comfort, functionality, and classic style. From the moment you arrive, you'll appreciate the welcoming front porch—a great spot to enjoy your morning coffee

    Donna DeCesaris Taylor Properties

    2643 Richfield Ln, Chesapeake Beach, MD 20732
  • /33

    $359,900

    • 3 Beds
    • 2.5 Baths
    • 1,600 Sq Ft

    2221 Ivy Ln Unit 9, Chesapeake Beach, MD 20732

    Nestled in the charming Richfield Station Village, this delightful Colonial townhouse offers a perfect blend of comfort and style. Built in 2007, the home features a warm and inviting interior, highlighted by beautiful flooring and recessed lighting that create a cozy ambiance throughout. The spacious living area seamlessly flows into a dining area, ideal for gatherings and entertaining. The

    Mason Halsey ExecuHome Realty

    2221 Ivy Ln Unit 9, Chesapeake Beach, MD 20732
  • /61

    $650,000

    • 5 Beds
    • 3.5 Baths
    • 3,837 Sq Ft

    3555 Christiana Ct, Chesapeake Beach, MD 20732

    Looking for true privacy with NO HOA, then look no further to this quaint Colonial nested in 5.09 acres of wooded area in Chesapeake Beach. The sprawling acreage has so much to offer - sit in your screened in porch, on your back deck, or build a fire pit & experience the nature. Inside you will find a well designed floor plan with room where you need it-5 bedrooms, 3.5 baths and over 3800

    Terri McClain RE/MAX One

    3555 Christiana Ct, Chesapeake Beach, MD 20732
  • /33

    $1,200,000

    $100K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 3,100 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

    Sarah Reynolds Keller Williams Realty

    4011 27th St, Chesapeake Beach, MD 20732
  • /50

    $589,500

    $35K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,464 Sq Ft

    3955 Breezy Point Rd, Chesapeake Beach, MD 20732

    NEW PRICE, MOVE-IN READY, easy drive to Andrews AFB, Washington DC , the Beltway. Looking for the perfect blend of privacy and accessibility? This low maintenance Colonial-style home, nestled on a generous 2.49-acre lot offers just that! No HOA!! A private paved driveway and surrounding hardwood trees provide privacy and a quick drive to Route 4 provides the convenience. Built in 2016, this 4 BR/

    Chris McNelis Berkshire Hathaway HomeServices PenFed Realty

    3955 Breezy Point Rd, Chesapeake Beach, MD 20732
  • /34

    $749,900

    $75K PRICE DROP
    • 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
  • /31

    $535,000

    $15K PRICE DROP
    • 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
  • /40

    $362,500

    $3K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,658 Sq Ft

    2233 Ivy Ln Unit 3, Chesapeake Beach, MD 20732

    Enjoy easy, low-maintenance living in this beautifully maintained GROUND LEVEL 2-bedroom, 2.5-bath condo located in one of Chesapeake Beach's most sought-after communities, Richfield Station. Conveniently situated for commuters traveling to Washington, D.C., JBA, and Annapolis, this home also offers the opportunity to enjoy all the charm and amenities of Chesapeake Bay living. The bright, open

    Erika Kaine Samson Properties

    2233 Ivy Ln Unit 3, Chesapeake Beach, MD 20732
  • /50

    $475,000

    • 4 Beds
    • 3.5 Baths
    • 2,875 Sq Ft

    3781 Bedford Dr, North Beach, MD 20714

    Just a 10-minute stroll to the North Beach Boardwalk, sandy beach, shops & some great places for local dining! Plus a brewery with live music, café and Saturday farmers market right at your doorstep.This beautiful 4-bedroom, 3.5-bathroom townhome offers the full coastal lifestyle in a move-in ready package. The open floor plan features hardwood floors throughout the living, kitchen, and

    Monique Ligthart EXP Realty, LLC

    3781 Bedford Dr, North Beach, MD 20714
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