Chesapeake Beach MD Real Estate & Homes for Sale

****CHESAPEAKE BAY VIEWS*** Welcome to this charming 2-bedroom, 1-bath bungalow nestled in the intimate waterfront community of Baycrest in Chesapeake Beach. Completely renovated in 2025, this home offers the peace of mind of all-new systems and finishes while maintaining its coastal charm. Perfectly blending comfort and coastal charm, this home offers an easygoing lifestyle just steps from the Chesapeake Bay. Savor outdoor living at its best with a private hot tub in the fenced backyard and bay views from the deck, perfect for relaxing or entertaining. Baycrest is a hidden gem, quiet, well-maintained, and neighborly ideal for those seeking a relaxed waterfront setting. Enjoy direct access to the bay with the community's kayak launch and lift system or unwind on the shared pier while taking in the stunning bay views. Located in one of the Chesapeake Bay's beloved twin beaches, Chesapeake Beach paired with neighboring North Beach offers a unique coastal lifestyle rich in charm and activities. Minutes away from the boardwalk, Bayfront Park, local restaurants, eclectic shops and seasonal events. The area also features the Chesapeake Beach Railway Museum, scenic Chesapeake Beach Rail Trail, fishing piers, and the commemorative Veterans' Memorial Park. Outdoor enthusiasts will appreciate nearby Brownie's Beach/Bayfront Park, known for fossil hunting and sharks' teeth, along with charter fishing excursions, full-service marinas, and convenient boat ramps. With Washington, DC and Baltimore both about an hour away, you'll appreciate the convenient commute without sacrificing that true bayfront feel. Whether you're looking for a weekend escape or a full-time retreat, this delightful bungalow offers you the perfect place to call home.

Lakefront Community Living Meets Country Comfort! Escape to the best of country living in this stunning 3 bedroom, 3 bathroom Split-Level home, perfectly situated on an over 1 -acre cul-de-sac lot in the highly sought-after, lake-privileged community of Lake Karylbrook. Whether you are an avid angler or a nature lover, you'll enjoy exclusive access to a private lake known for some of the best fishing in the state. Designed for Living & Entertaining, the main level boasts a, beautifully opened-up kitchen featuring a large center island, built in pantry, mainly all stainless steel appliances, and a seamless flow into the living areas, it's the perfect hub for hosting or quiet morning meals. The spacious lower-level family room offers a warm retreat centered around a classic brick fireplace, now updated with a propane freestanding stove. This level also provides direct access to the rear deck, perfectly blending indoor comfort with outdoor tranquility. Exterior & Accessibility Curb appeal shines with elegant stone veneer accents and a charming front porch, which includes a handicap ramp for easy accessibility. The backyard is a private, wooded sanctuary where natural beauty abounds. With scenic views located directly behind the property, (it backs up to BGE's right of way) your backyard is a gateway for hiking, exploring, or horseback riding. The Hobbyist's Dream 2-Car Garage features a large enclosed addition, ideal for a workshop, home gym, or storage. The oversized paved driveway provides plenty of space for parking and storing an RV, boat, or trailer. Enjoy peace of mind with major updates already handled: the roof and HVAC were both replaced in 2017. Located just minutes from the vibrant attractions of Chesapeake Beach and the Bay, this home offers a serene lifestyle with an easy commute to Joint Base Andrews (JBA), Pax River, Annapolis, and DC. All this is nestled within an exceptional community with a voluntary HOA of only $50/year! Don't miss your chance to own this rare piece of paradise - schedule your tour today!

3-bedroom, 3-bath home with a renovated interior and hardwood flooring throughout. Functional layout with updated finishes, including stainless steel appliances. Includes a sunroom addition that provides additional living space, along with a fenced-in yard offering privacy and usability. Solid overall layout with good interior and exterior features.

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 remarkably low HOA fee. Thoughtfully designed to accommodate both effortless everyday living and sophisticated entertaining, the home features a versatile floor plan with main-level living options, including two spacious bedrooms, a full bath, and a conveniently located laundry area. The upper level provides two additional well-appointed bedrooms and a second full bath, offering comfort and privacy for family and guests alike. Inside, main-level hardwood flooring sets a warm and inviting tone throughout, while the beautifully updated kitchen showcases stainless steel appliances, granite countertops, and timeless finishes. A stylish standalone electric fireplace serves as a focal point, creating an atmosphere of comfort and charm. Outdoors, the property transforms into a private retreat. Enjoy serene moments or host gatherings in the well-maintained backyard, complete with an outdoor hot tub - perfect for unwinding beneath the stars. Car enthusiasts and boating aficionados will appreciate the impressive detached two-car garage with a high ceiling, ideal for additional storage or accommodating one larger recreational vehicle such as a boat. A generous driveway provides ample additional parking. Modern comfort is ensured with a dual-zone commercial-grade HVAC system, delivering efficient climate control year-round. Ideally located just minutes from the Chesapeake Bay, residents enjoy convenient access to beaches, the boardwalk, boutique shopping, dining, and entertainment. Nearby Herrington Harbour Marina Resort offers premier waterfront amenities, including boat slips, private beaches, and upscale dining. With seamless connectivity to Washington, DC, Annapolis, and Joint Base Andrews - as well as weekday commuter bus service - this residence offers the perfect balance of coastal serenity and metropolitan accessibility.

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 nature or take the opportunity to exercise along the way! The beach connects to the boardwalk which allows for a scenic walk/jog/run into downtown Chesapeake Beach. With 4 bedrooms and 3.5 bathrooms this home offers a thoughtful design for both privacy and connected living. A dedicated office space at the front entrance of the home is perfect for those who work from home. Or utilize it as a formal dining room - you have options! The blended kitchen, dining and family room provide fluidity while getting the chores of the day accomplished. You'll love the walk-in pantry in the kitchen and the propane fireplace in the family room for cozy evenings. The recently enhanced Trex deck is located just off of the dining area and flows into the fenced back yard. The property also includes a standalone shed that provides ample additional storage for tools, outdoor equipment, or seasonal items. Enjoy the convenience of upstairs laundry just off of the spacious primary suite with walk-in closet and large en suite bathroom. Two more bedrooms and another full bath round out the upstairs. In the lower level you'll find plenty of room for activities, a fourth bedroom and full bathroom. A two-car garage provides covered parking and additional storage space! Equipped with a whole-house generator (Generac) and smart control panel, worry-free living awaits the new owners. Updates include an under sink Reverse Osmosis drinking water system (2023) with filters replaced annually (March 2026), Trex decking (2025), a new dishwasher (2025), and a 50 amp outlet alongside the garage for EV fast charging or RV use (2024).

Location, Location, Location! Enjoy the best of coastal living just minutes from the Chesapeake Bay, boardwalk, and fishing pier. Ideally positioned less than five minutes from the beach, Chesapeake Beach Railway Trail, and the charming waterfront towns of North Beach and Chesapeake Beach, this home places you right in the heart of it all. Welcome to your new home! This well-maintained 3-bedroom, 2-bath raised ranch offers the perfect balance of comfort, functionality, and lifestyle. The fully finished lower level expands your living space with a versatile bonus/flex room - perfect for a recreation area, home theater, game room, or guest suite. Live in the Chesapeake Beach lifestyle - just minutes from resident-only Bayfront Park Beach, with seasonal access to paddleboarding and kayaking. Enjoy a vibrant community with local events including summer festivals, waterfront fireworks, outdoor movie nights, and holiday markets - all just moments from your doorstep. Convenient to Washington, Baltimore, Annapolis, Joint Base Andrews, Naval Air Station Patuxent River Whether you're looking to upsize, settle into your forever home, or enjoy life near the coast, this home delivers on every level. Don't miss your opportunity to own a slice of coastal Maryland living - schedule your private showing today!

Beach cottage in a small, private, Chesapeake front community with bay access where you can swim, sunbathe and hunt for shark's teeth and fossils. This community is tucked along the shore of The Chesapeake Bay. The cottage has a fireplace that adds to its charm. Plentiful driveway (2) parking and a yard with a treed view. Chesapeake Beach boasts lots of activities within a reasonable commute to DC, Virginia and PAX River Naval base.

Step inside and feel at home in this spacious interior townhome at Richfield Station. As one of the community's larger models, it features a sunroom bump-out off the kitchen, perfect for relaxing or entertaining. The eat-in kitchen offers abundant space and possibilities for your dream upgrades. Sunlight pours across the main level, highlighting the stylish LVP flooring. Upstairs, discover three inviting bedrooms, including a primary suite with a walk-in closet and private bath. A second full bath adds convenience for family or guests. Freshly shampooed carpeting covers the upper level and basement, with most replaced within the last few years. The fully finished basement provides a generous storage room, a rough-in for a future bath, and a dedicated laundry area. Step out back to enjoy peaceful wooded views, and take advantage of two assigned parking spots at your doorstep. The community offers amenities like basketball and tennis courts, winding sidewalks, open green spaces, and a playground. Embrace the local lifestyle with nearby farmers markets, scenic boardwalks and piers, and great restaurants. All this, just 35 minutes from Joint Base Andrews and within 45 minutes of both Washington, DC and Annapolis. The seller is in the process of replacing the outdoor porch light fixture.

Welcome to 3905 26th Street - a 3-bedroom, 3 full and 1 half bath home set just moments from the Chesapeake Bay in the heart of Chesapeake Beach, where a flexible layout and multiple suite options come together in a setting that feels both comfortable and connected to the water. The main level opens into a series of well-defined living spaces, including a large living room and a separate family room centered around a fireplace that creates a warm focal point. The dining area offers space to host comfortably without feeling formal, positioned just off the kitchen for an easy, natural flow. The kitchen features extensive cabinetry, generous counter space, and room for a breakfast table, along with direct access to the rear deck - making everyday living and outdoor dining feel seamless. Also on this level, a bedroom with its own attached full bath provides a highly functional option for guests, a private office, or a main-level suite. A separate half bath completes the space. Upstairs, the primary suite offers a spacious layout with its own full bath and dedicated closet space, creating a comfortable retreat. A second upper-level bedroom is paired with an additional full bath, giving each space the support and privacy it needs without compromise. The lower level remains unfinished, offering a clean, open footprint for storage, workshop use, or future expansion. Outdoor living continues with a covered front porch, rear deck, and patio area, along with a detached garage that adds flexibility for parking, storage, or hobbies. The yard is usable and manageable, offering space to enjoy without extensive upkeep. Just down the street, Chesapeake Beach Veterans Memorial Park opens to sweeping Chesapeake Bay views, walking paths, and open green space - an everyday extension of the home that invites you outside. Nearby marinas, local dining, and small-town conveniences shape the rhythm of daily life here, while Bayfront Park - known locally as Brownie's Beach - is just about a mile away, offering a more private waterfront setting for Chesapeake Beach residents and their guests. With convenient access to Route 260 and Route 4, commuting to Annapolis, Washington, and surrounding areas is straightforward, while the setting itself offers a relaxed coastal pace that's hard to replicate. Enjoy close proximity to the Chesapeake Bay, the Rod 'N' Reel Resort, the Chesapeake Beach Water Park, nearby restaurants, shops, marinas, and the waterfront attractions that make this community such a special place to call home.

Welcome to this expansive 3BR, 3BA split-foyer in Chesapeake Beach! The light-filled upper level boasts a seamless flow between the living area and an updated kitchen with granite countertops and stainless steel appliances. Step into the stunning sunroom off the kitchen - your private sanctuary for morning coffee with views of the fully fenced-in backyard that backs to trees! The finished lower level features a classic brick fireplace with a pellet stove insert, a bar area, a full bathroom, and additional space for a hobby room, access to the garages, etc! Great location! Minutes to the Chesapeake Beach Resort & Spa, marinas, boardwalk, Bayfront Park, and local dining. Enjoy the best of the beaches, shopping, and waterfront lifestyle right at your doorstep!

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.

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 washer and dryer. Two additional bedrooms on the opposite side from owner's suite. Enjoy the backyard from the large sunroom just off the kitchen. The finished lower level includes stylish trim work, a full bath with ceramic tile shower, and additional storage space, plus den / bedroom for guests. Behind the garage is a large bonus room, perfect for entertainment. Two car garage with additional storage under bonus room, plus additional parking for vehicles or an RV. Built with 2x6 construction and equipped with a high-efficiency 3-zone, 21 SEER HVAC system, keeping utility bills low. Pellet Stove for extra heating in the basement. A large private backyard completes this exceptional property. Contact Listing Agent for more details!

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.

Welcome to 3238 Rector Lookout in the sought-after community of Chesapeake Beach, MD 20732 - a beautifully maintained single-family home offering space, comfort, and versatile living areas throughout. This impressive home features an attached two-car garage and a thoughtfully designed floor plan ideal for both everyday living and entertaining. The main level boasts a bright living room and formal dining room, along with a convenient half bathroom. The spacious kitchen is the heart of the home, complete with granite countertops, a center island, stainless steel appliances, and a charming breakfast nook highlighted by skylights. From the breakfast area, step directly out to the patio - perfect for outdoor dining and relaxation. Just off the kitchen, the inviting family room features a cozy gas fireplace, creating a warm and welcoming atmosphere. A versatile bonus room on the main level offers endless possibilities as an additional family room, recreational space, playroom, or home gym. Upstairs, the expansive primary suite provides a private retreat with a luxurious en-suite bathroom featuring a jetted soaking tub, separate shower, and dual vanities. Two additional generously sized bedrooms, a full hall bathroom, and a convenient upper-level laundry room complete the second floor. The partially finished basement adds even more flexible living space, including a full bathroom and an additional room that can easily function as a home office or guest bedroom. Major updates provide peace of mind, including a brand-new roof installed in 2025 with a 50-year transferable warranty and a new HVAC system installed in 2024, offering efficiency and long-term value. With its spacious layout, multiple living areas, and desirable location in Chesapeake Beach, this home offers the perfect blend of functionality, comfort, and thoughtful updates - ready to welcome its next owner. Mortgage savings may be available for buyers of this listing.

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.

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 into the kitchen with a large center island - perfect for everyday living and entertaining. Upstairs, the primary suite includes a private en suite bath, complemented by three additional bedrooms, a full hall bath, and a conveniently located laundry room. An attached garage and driveway offer ample parking. Pictures and renditions are examples only. Price will vary depending on model and selected options. Available upgrades include a larger front porch, screened porch, patio, or deck for enhanced outdoor living. A finished basement may also be an option. Additional home models are available. Ideally located with convenient access to the North Beach boardwalk, marinas, and Brownie's Beach. Enjoy walkability to local restaurants and an easy commute to Annapolis, Washington, D.C., Joint Base Andrews, Baltimore, and Northern Virginia. TO BE BUILT home. Price shown includes base house price, lot and estimated lot finishing cost only. Lot and home are sold under separate contracts. Pricing is subject to change. Site development costs may vary.

Great price for this 4-Level home with a total of 2,482 sf -- including 447 sf of unfinished storage space on bottom level! Almost one acre (.81) of land surrounded by mature trees and in great Northern Calvert location of top-rated schools. Kitchen has stainless steel appliances, and has real wood cabinets that a new owner could paint to easily update! Kitchen has a pantry, a breakfast bar and durable wide-plank laminate flooring. The main level has cathedral ceilings that give the home a spacious, contemporary feel. Perfect home for entertaining-- or for family members to spread out. Has three bedrooms upstairs, including the primary suite with a renovated bathroom with a tile shower. Downstairs, the finished lower level has a large, family room centered around a cool brick electric fireplace, along with a practical, oversized laundry area that opens to the back yard. The bonus, unfinished basement level provides excellent potential for customization - whether adding living space, a home office, gym, or just maximum storage space. The backyard is ideal for summertime fun with a huge deck for grilling and relaxing outdoors. Home has major improvements that include a newer roof and a newer HVAC system. Excellent location near beaches, restaurants, shopping and marinas. Easy commute to Washington, D.C. and Joint Base Andrews (JBA).

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 anything else you want it to be. It currently accommodates gym equipment and a full-size hot tub. Enjoy spectacular views from the upper level and the rare ability to walk to everything both Chesapeake Beach and North Beach have to offer - restaurants, boardwalks, marinas, and local attractions. Whether you're searching for a full-time coastal residence or the quintessential weekend beach retreat, this home offers the space, flexibility, and location to make it your own. The size, structure, and possibilities are all here - bring your vision and create the beach home you've been dreaming of.

This 5-bedroom, 3-bathroom home is ready for new owners! Located on a quiet cul-de-sac with a huge fenced-in backyard and a spacious deck off the kitchen. Convenient Chesapeake Beach location, close to the Chesapeake Bay, and all the amenities that Chesapeake Beach has to offer! Bayfront Park, shopping, restaurants, the water park, ballparks, playgrounds, community center, marina, boardwalks, and nature trails! Easy commute to Joint Base Andrews, Pax River, Annapolis, and DC.

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.

This 3-bedroom, 1-bath home on 4th Street blends modern updates with coastal charm in a prime Chesapeake Beach location. And it comes with a bonus: the sale includes the additional lot directly across the street. The exterior features fresh paint and blue accents that enhance its curb appeal, while the fenced yard adds privacy and function. "New septic system has just been installed" Inside, hardwood floors flow through the open living area, highlighted by a fireplace that creates a natural focal point. The kitchen showcases white cabinetry, sleek hardware, stainless steel appliances, and direct access to a new deck, ideal for outdoor dining and gatherings. The full bath has been thoughtfully renovated with stylish tile, contemporary fixtures, and a skylight that fills the space with natural light. Three bedrooms provide comfortable living areas with neutral finishes and closet storage. A laundry nook with a washer and dryer enhances daily living, and a one-car driveway ensures off-street parking. The new rear deck extends the living space outdoors, overlooking a fenced yard with space for pets, gardening, or relaxation. With no HOA restrictions, the property offers flexibility for future projects or personal touches. Located minutes from the boardwalk, beaches, restaurants, and local shops, this home presents an appealing lifestyle opportunity in a sought-after setting. "Some images may reflect virtual staging or digital editing, including removal of personal property, to help showcase the home."