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Explore Similar Homes Within 2 Miles of 20689, MD

  • /2

    $685,000 Open House 4/17

    • 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
  • /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
  • /34

    $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
  • /67

    $780,000 Open Sat 1PM - 3PM

    • 4 Beds
    • 3.5 Baths
    • 4,018 Sq Ft

    7005 Napa Dr, Chesapeake Beach, MD 20732

    Welcome to 7005 Napa Drive in Chesapeake Beach, Maryland, a beautiful and modern 4-bedroom, 3.5-bathroom rambler offering the convenience of main-level living in Calvert County with space for guests, entertaining, and everyday comfort. This spacious Chesapeake Beach home features a thoughtful layout with generous living areas, comfortable bedrooms, and a primary ensuite that is an oasis. The

    Brenda Huelle EXP Realty, LLC

    7005 Napa Dr, Chesapeake Beach, MD 20732
  • /49

    $570,000

    • 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
  • /37

    $415,000 Open Sat 11AM - 1PM

    • 4 Beds
    • 2.5 Baths
    • 1,999 Sq Ft

    2401 Green Leaf Terrace, Chesapeake Beach, MD 20732

    Open House Saturday, April 4th 10-12!Welcome to 2401 Green Leaf Terrace in Chesapeake Beach! This well-maintained end-unit townhome offers 4 bedrooms, including a basement bedroom that provides great flexibility for guests, a home office, or additional living space, along with 2 full baths and 1 half bath. SELLERS OFFERING A FLOORING CREDIT!! Backing to trees for added privacy, the home

    Lindsey Burch Samson Properties

    2401 Green Leaf Terrace, Chesapeake Beach, MD 20732
  • /27

    $750,000 Open Sat 10AM - 12PM

    • 4 Beds
    • 3.5 Baths
    • 3,072 Sq Ft

    490 W Mount Harmony Rd, Owings, MD 20736

    This beautifully renovated home is thoughtfully designed with both style and comfort in mind. As you step inside, you’ll be greeted by a spacious family room featuring a built-in bookcase, adding a touch of elegance to the heart of the home. The open, inviting atmosphere flows seamlessly throughout, with accent walls guiding you upstairs and down to the basement. The updated kitchen is a true

    Sarah Reynolds Keller Williams Realty

    490 W Mount Harmony Rd, Owings, MD 20736
  • /43

    $499,900 Open Sat 1PM - 2PM

    • 4 Beds
    • 2.5 Baths
    • 1,844 Sq Ft

    3604 Cox Ct, Huntingtown, MD 20639

    4 beds, 2.5 baths on 0.61 acres with a two-car garage in a location that makes day-to-day life easier. Main level is open with wood floors and an updated kitchen that connects well to the living space. Three bedrooms upstairs with updated baths. Lower level adds a second living area with a wood-burning fireplace, plus a fourth bedroom and half bath that is useful for guests, work, or giving

    Neil Smith Blackwell Real Estate, LLC

    3604 Cox Ct, Huntingtown, MD 20639
  • /63

    $700,000

    • 4 Beds
    • 3 Baths
    • 4,218 Sq Ft

    300 Owings Hill Ct, Owings, MD 20736

    Tucked quietly into Owings Hills, this home feels like it was pulled from the pages of a storybook.Follow the brick steps to the front door, and you’ll pass through perennial gardens that bloom and change with the seasons. Stone walls frame the landscape. Winding paths lead you to hidden corners. There’s even a fire pit tucked into the woods, reached by its own set of brick steps, ready for

    Dawn Riley RE/MAX One

    300 Owings Hill Ct, Owings, MD 20736
  • /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
  • /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
  • /64

    $499,900

    • 4 Beds
    • 2.5 Baths
    • 1,500 Sq Ft

    2972 Tartan Ln, Chesapeake Beach, MD 20732

    Nestled in the charming community of The Highlands, this delightful Colonial-style home offers a perfect blend of comfort and convenience. This well-maintained residence boasts 1,860 square feet of inviting living space, featuring four spacious bedrooms and two and a half bathrooms. The heart of the home is a cozy living area with a warm fireplace, ideal for creating lasting memories with loved

    Kelly DePaulo Keller Williams Capital Properties

    2972 Tartan Ln, Chesapeake Beach, MD 20732
  • /39

    $599,900

    • 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
  • /52

    $685,000

    • 4 Beds
    • 3.5 Baths
    • 3,016 Sq Ft

    7120 Bluegrass Way, Owings, MD 20736

    **New professional photos coming soon to reflect the newly installed flooring.** From the moment you step onto the wide front porch, something shifts. Ceiling fans stir a soft breeze, the sun settles through the trees, and you can already picture slow mornings with a cup of coffee, a dog curled at your feet, and the kind of peace most homes only hope to offer. It feels like home before you even

    Sarah Faisal Compass

    7120 Bluegrass Way, Owings, MD 20736
  • /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
  • /36

    $439,900

    • 4 Beds
    • 2 Baths
    • 1,850 Sq Ft

    3617 30th St, Chesapeake Beach, MD 20732

    NEW ROOF INSTALLED!! NEW EXTERIOR PAINT!!This well-maintained home offers bright, open living spaces within the Chesapeake Beach town limits. Natural light, hardwood floors, and an easy flow between the living, dining, and kitchen areas create a comfortable setting for everyday living and entertaining.The updated kitchen features a center island, ample cabinetry, and an open dining area

    Susan Reinhart Compass

    3617 30th St, Chesapeake Beach, MD 20732
  • /64

    $849,950

    • 4 Beds
    • 2.5 Baths
    • 2,300 Sq Ft

    9000 Bay Ave Unit 401 & 402, North Beach, MD 20714

    Welcome to this stunning, one-of-a-kind penthouse condo, offering unparalleled views of the Chesapeake Bay and the beach. Located in the coveted town of North Beach , this unique home combines two original units (401 & 402), creating a vast and luxurious living space that truly showcases the best of waterfront living. As you step through the front door, you’re greeted by breathtaking views

    Pattee McInerney Scott McInerney RE/MAX One

    9000 Bay Ave Unit 401 & 402, North Beach, MD 20714
  • /54

    $589,990 Coming Soon

    • 4 Beds
    • 2.5 Baths
    • 2,398 Sq Ft

    2614 Apple Way, Dunkirk, MD 20754

    Welcome to this beautifully maintained 4-bedroom, 2.5-bathroom single-family home in one of Dunkirk’s most desirable neighborhoods — with absolutely no HOA. Perfectly situated on approximately three-quarters of an acre and backing to untouched woodland, this property offers the privacy, space, and serenity that are increasingly hard to find. Every inch of this home has been cared for with pride,

    Tyler Charles Long & Foster Real Estate, Inc.

    2614 Apple Way, Dunkirk, MD 20754
  • /54

    $525,000 Open House 4/19

    • 4 Beds
    • 2.5 Baths
    • 2,288 Sq Ft

    9607 Cortland Ln, Dunkirk, MD 20754

    BUYER CLOSING COST ASSISTANCE & HOME WARRANTY!The Ultimate Dunkirk Retreat – Modern Luxury Meets Colonial CharmWelcome to 9607 Cortland Lane, a stunning 3-story Colonial where timeless architecture meets a massive list of modern upgrades. From the moment you arrive, the charming front porch with its wide, inviting entry stairs sets the tone for a home built for both relaxation and

    Karen Reisdorf Berkshire Hathaway HomeServices PenFed Realty

    9607 Cortland Ln, Dunkirk, MD 20754
  • /79

    $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
  • /15

    $549,900 Open House 5/09

    • 4 Beds
    • 3 Baths
    • 2,037 Sq Ft

    3913 6th St, North Beach, MD 20714

    Welcome to exceptional coastal living in the heart of North Beach, where ease of living and lifestyle come together. Perfectly positioned on 6th Street, this beautifully appointed residence offers versatile living space, thoughtfully designed for both everyday comfort and effortless entertaining. North Beach is beloved for its vibrant yet relaxed coastal atmosphere, featuring a scenic boardwalk,

    Emily McGann Compass

    3913 6th St, North Beach, MD 20714
  • /2

    $799,990 Coming Soon

    • 4 Beds
    • 3.5 Baths
    • 4,000 Sq Ft

    1050 Fowler Rd, Owings, MD 20736

    Fantastic location for this custom-built rancher offering over 4,000 square feet of living space and an open, contemporary floor plan--perfect for everyday living and entertaining! The main-level primary suite provides convenience and privacy, featuring double vanities, dual closets, and even a relaxing sauna. The stately brick front exterior is complemented by a 3+ car garage, additional storage

    Team Stueckler Keller Williams Flagship

    1050 Fowler Rd, Owings, MD 20736
  • /2

    $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
  • /2

    $939,900 Open Sat 11AM - 1PM

    • 4 Beds
    • 3.5 Baths
    • 4,305 Sq Ft

    1015 Pondcypress Ln, Huntingtown, MD 20639

    Welcome to this exceptional rambler with a fully finished lower level, ideally located in the highly sought-after Twin Ponds community in Huntingtown. Built in 2021 by Quality Built Homes, this stunning residence showcases over 5,700 finished square feet of thoughtfully designed living space, blending modern luxury with everyday comfort. Perfectly situated on a level 2-acre lot with room for a

    Laura Peruzzi RE/MAX One

    1015 Pondcypress Ln, Huntingtown, MD 20639
  • /2

    $495,000 Open House 4/19

    • 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
  • /2

    $875,000 Coming Soon

    • 4 Beds
    • 3.5 Baths
    • 4,009 Sq Ft

    90 Oxford Way, Huntingtown, MD 20639

    Karen Rider-Tabor O'Brien Realty ERA Powered

    90 Oxford Way, Huntingtown, MD 20639
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