Features & Amenities

Interior

  • Other Interior Features

    Ceiling Fan(s), Pantry, Walk-In Closet(s), Built-in Features, Open Floorplan

  • Total Bedrooms

    4

  • Bathrooms

    4

  • 1/2 Bathrooms

    1

  • Above Grade Finished Area

    2190.0

  • Basement YN

    NO

  • Cooling YN

    YES

  • Cooling

    Central Air, Heat Pump, Ceiling Fan(s), Electric

  • Fireplace YN

    YES

  • Heating YN

    YES

  • Heating

    Electric, Heat Pump

  • Pet friendly

    N/A

Exterior

  • Garage

    Yes

  • Garage spaces

    1

  • Construction Materials

    Frame

  • Other Exterior Features

    Barbecue, Awning(s)

  • Parking

    Private, Paved, Garage, Parking Lot, Driveway, Inside Entrance, Attached

  • Pool

    Yes

  • Pool Features

    Community

  • Waterfront YN

    YES

  • View

    Water, Bay, Panoramic, Scenic

Area & Lot

  • Lot Features

    Other, Cleared, Waterfront

  • Lot Size(acres)

    0.04

  • Lot Size(square feet)

    1743.0

  • Property Type

    Residential

  • Property Sub Type

    Townhouse

  • Architectural Style

    Transitional, Other

Price

  • Sales Price

    $885,000

  • Tax Amount

    $6,810

  • Sq. Footage

    2, 513

  • Price/SqFt

    $352

HOA

  • Association

    Yes

  • Association Fee

    $410

  • Association Fee Frequency

    Monthly

  • Association Fee Includes

    N/A

School District

  • Elementary School

    BEACH

  • Middle School

    WINDY HILL

  • High School

    NORTHERN

Property Features

  • New Construction

    NO

  • Association Amenities

    Beach Access

  • Foundation Details

    Slab

  • Senior Community YN

    NO

  • Sewer

    Public Sewer

  • Tax Lot

    66

  • Water Source

    Public

Schedule a Showing

Showing scheduled successfully.

<
>
IN PERSON
VIA CHAT

What is 3 + 4 ?


Change time

Mortgage calculator

Estimate your monthly mortgage payment, including the principal and interest, property taxes, and HOA. Adjust the values to generate a more accurate rate.

Your payment

Principal and Interest:

$

Property taxes:

$

HOA fees:

$

Total loan payment:

$

Total interest amount:

$

Location

County

CALVERT

Elementary School

BEACH

Middle School

WINDY HILL

High School

NORTHERN

Listing Courtesy of Sally L. D. Showalter , Deep Roots Real Estate

RealHub Information is provided exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All information deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change or withdrawal. RealHub website owner shall not be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless.

Agent Kasey Wootton

AGENT

Kasey Wootton

Call Kasey today to schedule a private showing.


* Listings on this website come from the FMLS IDX Compilation and may be held by brokerage firms other than the owner of this website. The listing brokerage is identified in any listing details. Information is deemed reliable but is not guaranteed. If you believe any FMLS listing contains material that infringes your copyrighted work please click here to review our DMCA policy and learn how to submit a takedown request.© 2024 FMLS.
Experience exceptional Chesapeake Bay waterfront living in this stunning four-level townhome offering unobstructed Bay views from nearly every room. Ideally located in Chesapeake Beach, this home provides convenient access to Annapolis, Washington, D.C., and the surrounding Metro area while embracing the relaxed lifestyle of Maryland's waterfront communities.
Enjoy all that Chesapeake Beach and neighboring North Beach have to offer, including award-winning restaurants, seasonal events, a scenic boardwalk perfect for walking, running, charming local shops, and friendly coastal living.
This is the only BAYFRONT home currently available in the highly desirable Windward Key community. Wake up to breathtaking sunrises, launch your kayak directly from your yard, hunt for shark teeth along the shoreline, and enjoy the sights of passing sailboats, fishing vessels, and cruise ships—all from the comfort of home.
Inside, an open-concept floor plan showcases beautiful Brazilian Koa hardwood flooring throughout the main living areas. The spacious kitchen features abundant cabinetry, elegant marble countertops, and a premium Bluestar gas range fueled by a dedicated propane tank. The adjoining dining area flows seamlessly into the light-filled living room, where a wall of windows and two sets of sliding glass doors open to a large waterfront deck—perfect for entertaining or simply relaxing while taking in the ever-changing Bay views.
The upper level features a spacious waterfront primary suite with a private balcony, ideal for enjoying morning coffee while watching the sunrise over the Bay. The luxurious primary bath offers a beautifully tiled walk-in shower. Two additional bedrooms and a full bath complete this level.
The top floor provides a private retreat currently used as an office but easily serving as a fourth bedroom or guest suite. Complete with a full bath and its own private deck, this space offers incredible flexibility and privacy.
The finished lower level expands the home's versatility with space for a recreation room, gym, studio, office, or additional bedroom, along with a full bath and laundry room featuring exterior access. A covered waterfront patio provides easy access to the community pool and outdoor amenities.
Windward Key residents enjoy exclusive access to a private beach, pickleball court, community pool, and marina, where boat slips may be purchased separately. HOA services include lawn maintenance and trash removal, allowing for truly low-maintenance waterfront living. (length  of footage is approx.)
Additional upgrades and features include:
• New Trex decking and railings throughout
• Built-in bookshelves that convey with the home
• Main-level deck grill connected to the propane system
• Attached garage with space for one vehicle plus extensive storage
• More than 3,000 square feet of living space
• Four levels of outdoor living areas designed to maximize the waterfront lifestyle
Opportunities to own a true Bayfront home in Windward Key are rare. Combining spectacular views, generous living space, exceptional amenities, and an affordable price point, this home offers the very best of Chesapeake Bay living.

8183 WINDWARD KEY DRIVE

Message successfully sent.

What would you like to know?

What is 3 + 4 ?

I agree to receive email communication and understand I can unsubscribe at any time.

I agree to be contacted by Charis Realty Group via call, email, and text for real estate services. To opt out, you can reply 'stop' at any time or reply 'help' for assistance. You can also click the unsubscribe link in the emails. Message and data rates may apply. Message frequency may vary. Privacy Policy

Related Properties

Wake up to breathtaking sunrises and sweeping waterfront views in this charming coastal retreat with access to the Chesapeake Bay and a sandy beach area. Perfect as a vacation getaway or year-round residence, this property offers the ideal blend of relaxation and waterfront living.

An additional building lot is included, 3711 Bayview Dr. providing endless possibilities — keep it separate for added value or combine the parcels to create your dream waterfront estate with room for a much larger home. Enjoy boating, beach days, and peaceful coastal living in a truly special setting. A very unique and rare opportunity!
#MDCA2027056

CHESAPEAKE BEACH

3713 & 3711 BAYVIEW DRIVE

2 Beds

1 Baths

869 Sq.Ft.

$865,000

MLS#: MDCA2027056

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 upscale amenities throughout. Designed for both comfort and entertaining, the home features 4 bedrooms, 4 full baths, and 1 half bath across four spacious levels filled with natural light. The main living level showcases a well-appointed kitchen, dining area, and expansive great room with a cozy gas fireplace — all enhanced by water views and an open, airy feel. The upper level hosts the primary suite along with two additional bedrooms, while vaulted ceilings create an inviting sense of space and elegance. The top level offers exceptional flexibility with its own full bath, wet bar, and private deck, ideal for a home office, guest suite, lounge, or entertainment space overlooking the Bay. The entry level provides additional finished living space with a full bath, perfect for guests, recreation, fitness, or flex living. Direct access to the attached one-car garage adds convenience and functionality. Outdoor living is elevated with multiple decks on every level, creating seamless indoor-outdoor enjoyment and endless opportunities to relax and take in the coastal setting. Residents of Windward Key enjoy exclusive amenities including a waterfront pool overlooking the Chesapeake Bay and a private beach. Located within walking distance to restaurants, shops, parks, boardwalks, marinas, nature trails, and local entertainment, this is Chesapeake coastal living at its finest.
#MDCA2026440

CHESAPEAKE BEACH

8076 WINDWARD KEY DRIVE

4 Beds

4 Baths

2,950 Sq.Ft.

$775,000

MLS#: MDCA2026440

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 storage, and more. Whether you're an avid boater or simply love the water, this property has you covered with on-site boat slips (not deeded).

Picture yourself savoring every sunrise and sunset from your private decks or hosting friends and family as you take in the dazzling Chesapeake Beach fireworks right from the comfort of your home. It’s a lifestyle of relaxation, natural beauty, and endless opportunity.

With so much more to discover, this is your chance to own a slice of paradise. Don't wait—this coastal retreat won't last long!
#MDCA2026816

CHESAPEAKE BEACH

8048 WINDWARD KEY DRIVE

3 Beds

4 Baths

2,583 Sq.Ft.

$759,900

MLS#: MDCA2026816

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, illuminating rich cherry hardwood floors that flow throughout the main and upper levels. The main living level is designed for both elegant entertaining and everyday comfort, featuring a spacious great room with a gas fireplace, an inviting dining area, and a well-appointed gourmet kitchen with stainless steel appliances, pantry, and wine refrigerator. Step onto the private deck to take in tranquil bay and fishing creek views—perfect for morning coffee or evening gatherings. The lower level offers a versatile recreation space with a full bath and dedicated laundry room, ideal for guests or extended living, with seamless access from the attached garage. From here, step outside to your deck and connect directly to the waterfront walkway, embracing the true essence of coastal living. Upstairs, the primary suite serves as a luxurious retreat, complete with a custom closet system, additional storage, and a spa-inspired bath featuring a jetted soaking tub and separate shower. A private deck off the suite captures breathtaking water views, creating a serene escape. This level also includes an additional bedroom and full bath. The top level provides exceptional flexibility, offering a private suite with full bath and walk-in closet—perfect as a fourth bedroom, executive office, or fitness studio—opening to yet another deck with sweeping, unobstructed views of the bay. An attached garage, additional storage, and private driveway ensure convenience, while Windward Key residents enjoy exclusive amenities including a pool and private beach. Just moments from and walking distance to local dining, shopping, marinas, water sports, and the Chesapeake Beach Water Park, this home also offers easy access to Washington DC, Annapolis, Joint Base Andrews, and Northern Virginia. Live where you play—and indulge in the luxury of waterfront living every day.
#MDCA2025332

CHESAPEAKE BEACH

8054 WINDWARD KEY DRIVE

4 Beds

4 Baths

2,876 Sq.Ft.

$849,900

MLS#: MDCA2025332

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 home has 2 brand new HVAC systems, new carpet and has been freshly painted.  Move right in and start enjoying your new beach life! Because of its location within the community, you can also sit on any one of your decks and catch all the summer concerts, for free, being held in the resort's bandshell directly across the creek.  This is also the perfect location to catch the famous, Chesapeake Beach, 4th of July fireworks without ever leaving home. 

Residents enjoy exclusive access to a private community beach, beach side pool, pickleball courts, and even has a marina (marina slips are extra and are not deeded to the unit)—creating an effortless blend of leisure and coastal charm.  Whether you are launching a kayak right outside your backdoor or taking a scenic hike along Chesapeake Beach's Old Raildroad trail or shark tooth hunting on the beach, there are endless possibilities.  Whether you dock your own boat at the Rod &Reel or Marina West, or hire a charter, world class fishing and crabbing are just footsteps away. You can also walk to the Rod & Reel Resort and all it has to offer, as well as other in-town restaurants and shopping within Chesapeake Beach.  Within walking distance of Windward Key are multiple marinas. Pull your boat up to the boardwalk, right outside your door, to load it up and enjoy life on the bay!  Whether you’re seeking a peaceful weekend retreat or a full-time sanctuary, only 45 minutes from Annapolis and less than an hour from Washington, DC, this exceptional home offers an inviting opportunity to experience refined waterfront living at its finest.
#MDCA2025610

CHESAPEAKE BEACH

8047 WINDWARD KEY DRIVE

4 Beds

4 Baths

2,632 Sq.Ft.

$849,900

MLS#: MDCA2025610

Back on the market due to shaky financing! Inspected and READY! Improved price too! Welcome to 8229 Bayside Road, where elevated bayside living meets everyday convenience in the heart of Chesapeake Beach. This beautifully maintained four-bedroom, 3.5-bath residence offers views of the Chesapeake Bay and an unbeatable walkable lifestyle along the water. Spanning four finished levels and serviced by a private elevator reaching every floor, this home was designed for comfort and accessibility. The top-level primary suite is a true retreat, complete with private elevator access, stunning bay views, private bathroom and your very own lighthouse beacon that can actually be seen from the bay! Wake up each morning to the shimmer of the water and end your evenings on your private balcony with a cool breeze and your beverage of choice. 

The home is in excellent condition and thoughtfully laid out to maximize both space and light. Generously sized bedrooms, multiple gathering areas, and well-appointed baths provide flexibility for everyday living and hosting guests. Garage and driveway parking are off-street. Whether you’re looking for a full-time residence or a weekend escape, this home offers the perfect balance of function and relaxation.



Step outside and embrace the lifestyle that makes Chesapeake Beach so special. Everything you need is within walking distance - restaurants, local shops, a grocery store, marinas, fishing spots, and water activities. Spend your afternoons strolling the boardwalk, enjoying waterfront dining at local favorites like Rod ‘N’ Reel Restaurant, Traders & Baia Coastal, exploring the marina, or watching the boats roll in. Jet ski rentals, beaches, live entertainment, and even more dining options are just moments from your front door. In fact, you’re only a short walk to neighboring North Beach, expanding your access to even more waterfront charm, restaurants events, and recreation.

Here, you truly can park your car and leave it—this is bayside living at its most convenient and vibrant. Select photos are virtually staged.
#MDCA2024816

CHESAPEAKE BEACH

8229 BAYSIDE ROAD

4 Beds

3 Baths

2,700 Sq.Ft.

$777,000

MLS#: MDCA2024816

This spacious QBH custom built Colonial offers over 5,000 square feet of living space with 5 bedrooms, 4.5 bathrooms, an extra lot that conveys, and no HOA! Thoughtfully updated throughout, this home features a new HVAC system in 2021, brand-new carpet, newer appliances including a dishwasher and refrigerator replaced in 2025, microwave replaced in 2023, plus the washer and dryer. The main level offers a spacious office, perfect for working from home, and a beautiful kitchen with granite countertops, a large island, and plenty of room for a farmhouse table. The primary suite is a true retreat with a large sitting area, walk-in closet, walk-in tiled shower, and soaking Jacuzzi tub. Upstairs, one bedroom includes a private bathroom, while two additional bedrooms share a convenient Jack-and-Jill bath. The finished basement offers 9-foot ceilings, a built-in bar, the fifth bedroom, a full bathroom, and an additional flex space ideal for a workout room, art studio, office, or playroom. The fully fenced backyard is an outdoor oasis- resort style living features an in-ground heated saltwater pool with an electric pool cover, propane pool heater, waterfalls, lights, and updated pool equipment (including a pool pump and filter replaced in 2024, waterfall pump replaced in 2025, and new pool cleaner in 2026). Enjoy the deck with a retractable awning for added shade, outdoor kitchen with a propane grill (connected to the main propane system), an in-ground sprinkler system, landscaping lights, and tint on all back-facing windows, including the slider, to help with efficiency and comfort. Beautiful landscaping surrounds the property with lilies, hydrangeas, and more. Additional features include a dual active radon mitigation system, installed security system (that could be connected), 12x20 shed with 6x6 double doors, ramp, and dormers, plus a gravel pad perfect for RV, boat, or trailer parking. Town residents enjoy private access to Bay Front Park, also known as Brownie’s Beach, along with nearby walking paths on the Chesapeake Beach Railway Trail. With updated systems, incredible outdoor amenities, extra parking, an additional lot (totaling .96 acre), and no HOA, this home offers space, flexibility, and so much to love.
#MDCA2027870

CHESAPEAKE BEACH

3325 COX ROAD

5 Beds

4 Baths

3,863 Sq.Ft.

$1,050,000

MLS#: MDCA2027870

New on site 2 days ago
Not very often will you find a home with 5 bedrooms upstairs and a two bedroom  in-law wing on the main level with a separate entrance!  This house was built for comfortable living and lots of people! With 4200+ sq ft above grade, you won't want for more space!   Plenty of room for entertaining with a family room off the kitchen , a huge recreation room next door , a front porch for easy living and huge decks off the back from the kitchen and in law wing exiting to the fenced in  inground  pool !  Of course you have to have a screened gazebo for crabs too!  There are two additional storage sheds and a 2.5 car detached garage with loads of paved driveway parking for everyone living there!  Lots of recent updates include, new pool liner, pump and cover, within a few years, all new kitchen appliances, cabinets and Quartz counter tops.  Hvac 2019, well is 5 years old and hot water heater 5 years old. All of this and you are only 3 minutes away from North Beach and Chesapeake Beach with the board walk, restaurants, farmers markets and so  much more!  Crawl space is insulated with a vapor barrier .
#MDCA2027856

CHESAPEAKE BEACH

8407 WESLEY STINNETT BOULEVARD

7 Beds

3 Baths

4,278 Sq.Ft.

$724,500

MLS#: MDCA2027856

 - property

Send a message

Message successfully sent.

Your message

What is 3 + 4 ?

Reason for contacting?

I agree to receive email communication and understand I can unsubscribe at any time.

I agree to be contacted by Charis Realty Group via call, email, and text for real estate services. To opt out, you can reply 'stop' at any time or reply 'help' for assistance. You can also click the unsubscribe link in the emails. Message and data rates may apply. Message frequency may vary. Privacy Policy

Sign Out

Virtual Assistant

Would you like to take the next step with this property? We can help you schedule a showing or virtual tour, or send you more details.

Yes, I would like more information.

Thank You for Your Reply, One of Our Agents will contact you as soon as possible

No, maybe later.

Thank you, you can always contact me via email, phone number or through the contact form.

Realhub AI

Lucy - Your AI-Powered Realtor

Update Your Temporary Password

Personalize your search

Enter your email and we'll notify you immediately when new listings match what you're looking for.

or enter email address

Already have an account ? Login here

Continue your home search

I agree to receive communications and understand I can unsubscribe at any time.

I agree to be contacted by Charis Realty Group via call, email, and text for real estate services. To opt out, you can reply 'stop' at any time or reply 'help' for assistance. You can also click the unsubscribe link in the emails. Message and data rates may apply. Message frequency may vary. Privacy Policy

Already have an account ? Login here

We use cookies

We use cookies primarily for analytics to enhance your experience. By accepting, you agree to our use of these cookies. You can manage your preferences or learn more about our cookies policy.