Chesapeake Beach Homes with Colonial Style

Chesapeake Beach Homes with Colonial Style

Welcome to Chesapeake Beach, Maryland—a charming coastal town nestled in Calvert County that perfectly captures the essence of waterfront living. With its picturesque views of the Chesapeake Bay and a vibrant community, Chesapeake Beach is an idyllic destination for those seeking a serene lifestyle combined with the allure of coastal adventures.

This quaint town is known for its rich history, stunning beaches, and a plethora of recreational activities. From fishing and boating to hiking along scenic trails, residents and visitors alike can immerse themselves in the natural beauty that surrounds them. The local dining scene offers a delightful selection of seafood restaurants where you can savor the freshest catch, all while enjoying breathtaking views of the bay.

When it comes to real estate, Chesapeake Beach boasts an array of charming homes, including the timeless Colonial-style residences that grace its streets. These homes are characterized by their classic architecture, with symmetrical facades, gabled roofs, and inviting front porches that exude warmth and charm. Many of these Colonial homes are situated on spacious lots, providing ample outdoor space for family gatherings, gardening, or simply enjoying the peaceful surroundings.

Living in Chesapeake Beach means embracing a community that values its rich heritage while offering modern conveniences. With excellent schools, friendly neighbors, and a strong sense of community, it’s no wonder that this town is a sought-after destination for families and retirees alike. Discover your dream Colonial-style home in Chesapeake Beach, where coastal living meets timeless elegance.

Newest Chesapeake Beach Homes with Colonial Style

$739,900
3 Beds ⋅ 3 Baths
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 waterfront deck, creating seamless indoor and outdoor living. Upstairs, the primary suite becomes your personal waterfront retreat with its own private deck overlooking the Chesapeake Bay, beautifully updated bath, and the convenience of a dedicated washer and dryer. Two additional bedrooms enjoy water views as well, allowing family and guests to wake up to the beauty of the Bay every day. The walk-out lower level offers even more flexibility with a second washer and dryer, access to a stamped concrete waterfront patio, and a covered sitting area just steps from the shoreline—an ideal place to unwind after a day on the water. Residents enjoy exclusive access to a private community pier complete with a boat lift and fishing opportunities. Every Independence Day, neighbors gather to watch the spectacular fireworks display reflected across the Chesapeake Bay, creating a tradition you'll look forward to year after year. Located less than an hour from Washington, D.C., this home offers an exceptional primary residence, weekend escape, or second home without the hassle of Bay Bridge traffic. Enjoy the charm of Chesapeake Beach with its waterfront boardwalk, community beach, farmers markets, local breweries, boutique shopping, restaurants, outdoor concerts, marinas, and year-round events—all just minutes from your door. If you've been searching for true Chesapeake Bay waterfront living with modern updates, unforgettable views, and an unbeatable coastal lifestyle, this is the one.

8337 Bay Crest Ct, Chesapeake Beach

Listing courtesy of RE/MAX United Real Estate. Contact:

$365,000
2 Beds ⋅ 3 Baths
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 main level is ideal for both everyday living and entertaining. The updated kitchen features stainless steel appliances, large kitchen island and opens to spacious living areas, creating a comfortable and functional layout. A convenient half bath completes the main level. Upstairs, the spacious primary suite includes two walk-in closets and a private en suite bath. A second generously sized bedroom, a full hall bath, and an upper-level laundry area provide comfort and convenience for family or guests. Spend less time on home maintenance and more time enjoying everything the Twin Beach area has to offer. The HOA/COA alleviate most exterior maintenance responsibilities, making homeownership easy and stress-free. Take advantage of easy access to walking trails, Bayside Beach, trash service, and other local amenities. This property is move-in ready and ideally located, and offers the perfect combination of comfort, convenience, and Chesapeake Beach living.

2233 Ivy Ln Unit #3, Chesapeake Beach

Listing courtesy of Samson Properties. Contact: 4439757555
$650,000
4 Beds ⋅ 4 Baths
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 stall shower and separate soaking tub, a walk-in closet, and a private office. There are also three more bedrooms on the 2nd level along with another full bathroom. The basement features a rec room, plenty of storage space, a laundry/utility room, and an office/theater room with a separate outside entrance! The side yard area is fenced and there is also a storage shed in the back yard. The home is located in the awesome Highlands neighborhood, with recreation fields and a playground, and you're only a few minutes from everything that Chesapeake Beach and North Beach have to offer! This house is currently tenant-occupied, the tenants plan to move out by August 31st. Owner plans to repaint and clean property before going on the market.

8475 Saint Andrews Dr, Chesapeake Beach

Listing courtesy of Cerrito Realty, LLC. Contact: (301) 780-5880
$599,900
4 Beds ⋅ 3 Baths
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 space, brand new SS appliances, and an easy flow into the main living areas. Deck off of kitchen to enjoy peaceful mornings sipping coffee. Major updates include a new roof and new siding, giving added peace of mind for the next owner. Upstairs, you’ll find four spacious bedrooms, including a comfortable primary suite with its own private bath w/ dual sinks. The unfinished basement offers tons of potential and is already partially divided into usable areas, making it perfect for future finished living space, a home gym, storage, office, playroom, or hobby area. Located in desirable Chesapeake Beach, this home is ready for its next chapter and offers the perfect opportunity to move in now and customize over time.

2630 Richfield Ln, Chesapeake Beach

Listing courtesy of CENTURY 21 New Millennium. Contact: 3016099000
$599,900
4 Beds ⋅ 3 Baths
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/ 2.5 BA residence features 2,464 square feet of living space plus an unfinished basement for storage and future improvements. The kitchen has been upgraded to include app-controlled LG Thin-Q appliances and granite counters, connected to a spacious family room with modern electric fireplace. It is a great entertaining flow! The lot is very private, and from the newer rear deck you will enjoy the hardwood trees and changing seasonal colors, also many varieties of birds. The parking area is plentiful, with a front-entry attached two car garage and a detached carport that is equipped with two 240v EV-ready NEMA 14-50 outlets. This home is more than just a property; it's a sanctuary where you can create memories that last forever. Chesapeake Beach town center with stores and restaurants is close by, and Prince Frederick is a 10 minute drive for more shopping and services. The lot has a Forest Retention Area (FRA) and a natural path for hikes and discovery! See boundary line survey notes for details.

3955 Breezy Point Rd, Chesapeake Beach

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: 4103940990
$1,299,000
6 Beds ⋅ 5 Baths
Welcome Home to an Extraordinary Private Estate in Owens Soper Estates Hidden 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 home—it is a once-in-a-lifetime opportunity to own an irreplaceable estate where every day feels like a private retreat surrounded by natural beauty, refined craftsmanship, and an unmistakable sense of grandeur. From the moment you enter the driveway, the outside world begins to disappear. Towering hardwoods, peaceful streams, abundant wildlife, and the soothing sounds of nature create an unforgettable arrival, leading you home to a place where serenity and sophistication exist in perfect harmony. Properties offering this level of privacy, luxury, and recreation are exceptionally rare and nearly impossible to replicate. Built in 2022, this stunning residence offers over 6,000 square feet of beautifully designed living space that blends refined craftsmanship with modern comfort. Every room has been thoughtfully designed to maximize elegance, functionality, and the breathtaking views surrounding the home. The expansive floor plan features four spacious bedrooms with the flexibility to easily accommodate up to six bedrooms, making it ideal for multigenerational living, guests, or personalized spaces. The home also offers 4.5 luxurious bathrooms, including a spa-inspired owner’s suite featuring a spectacular custom tiled dual shower, relaxing Jacuzzi soaking tub, and elegant finishes that create the perfect private retreat. At the heart of the home is a magnificent chef’s kitchen complete with premium finishes, an oversized center island, abundant cabinetry, and an impressive walk-in pantry. Whether hosting elegant gatherings or enjoying quiet evenings at home, this space was designed to bring people together. Two beautiful wood-burning fireplaces add warmth, charm, and timeless character throughout the living areas. The fully finished lower level expands the home’s versatility with an impressive recreation room, oversized home gym, additional flex rooms, guest accommodations, and abundant storage. Designed for today’s lifestyle, high-speed internet and two dedicated home offices allow you to work remotely while enjoying complete privacy and breathtaking natural surroundings. Outside, approximately 2.5 acres surrounding the home have already been cleared, providing the perfect canvas for a future resort-style pool, outdoor kitchen, guest house, gardens, or luxury entertaining space while preserving the beauty and privacy of the surrounding forest. Beyond the homesite, your own private outdoor paradise awaits. Miles of established trails, wide enough for ATVs, utility vehicles, horseback riding, or peaceful hikes, wind through mature hardwood forests alongside picturesque streams. Private bridge crossings provide easy access throughout the property, making every acre an adventure waiting to be explored. Rich with deer, turkey, and abundant native wildlife, this property is a dream for hunters, outdoor enthusiasts, photographers, hikers, and nature lovers alike. Mature walnut, pawpaw, and valuable hardwood trees further enhance the property’s beauty while offering future stewardship opportunities. With no HOA, you’ll enjoy the freedom to create the lifestyle you’ve always envisioned. Whether your dream includes a family compound, luxury outdoor amenities, a private homestead, or simply preserving your own secluded sanctuary, the possibilities are endless. Despite its incredible privacy, you’re only minutes from top-rated Calvert County schools, shopping, restaurants, hospitals, parks, marinas, and the charming waterfront communities of Chesapeake Beach and North Beach, offering waterfront dining, fishing boutique shops.

4485 Bristol Dr, Chesapeake Beach

Listing courtesy of CENTURY 21 New Millennium. Contact: 4439689595
$370,000
3 Beds ⋅ 3 Baths
Coming Soon! Impeccably maintained 3-bedroom, 2.5-bath penthouse-style condo offering over 2,600 sq ft of living space and an attached garage in sought-after Richfield Station. This spacious open floor plan is filled with abundant natural light and features premium cabinetry, granite countertops, and a luxurious primary suite with dual walk-in closets and a spa-like bath with a dual shower. Additional highlights include fresh interior paint and EV-ready garage wiring. Conveniently located just minutes from Chesapeake Beach, North Beach, shopping, dining, and commuter routes. Professional photos coming soon.

2328 Forest Ridge Ter Unit #6, Chesapeake Beach

Listing courtesy of Fairfax Realty Premier. Contact: 3014399500
$650,000
5 Beds ⋅ 4 Baths
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 or unwind in the evening. Inside, you'll find bright, inviting living spaces with updates throughout, making this home truly move-in ready. The kitchen is the heart of the home and opens to a sunny four-season sunroom that's perfect for casual meals, relaxing with a book, or simply enjoying the view of the backyard. Just outside, the spacious deck provides the ideal setting for cookouts, entertaining friends, or spending time with family. The fully finished basement adds even more living space and includes a fifth bedroom, making it perfect for guests, a home office, a recreation room, gym, or whatever fits your lifestyle. Whether you need space for a growing family, work from home, or simply enjoy having room to spread out, this home offers the flexibility you've been searching for. Located in the desirable Richfield Station community, you'll enjoy the convenience of being just minutes from Chesapeake Beach, North Beach, marinas, restaurants, shopping, parks, and commuter routes while still coming home to a quiet, established neighborhood. This is more than just a house—it's a place to make memories. Schedule your private showing today and come see everything 2643 Richfield Lane has to offer.

2643 Richfield Ln, Chesapeake Beach

Listing courtesy of Taylor Properties. Contact:

$719,900
5 Beds ⋅ 4 Baths
Price reduction and One year home warranty included!!!! Welcome to 4416 Snowy Egret Court, a stunning 5-bedroom, 3 full bath, 1 half bath home located at the end of a quiet cul-de-sac in the highly desirable Breezy Point Estates community of Chesapeake Beach. Just one mile from the Chesapeake Bay, residents enjoy beach passes and private water access all year, offering the perfect blend of coastal living and everyday convenience. This beautifully maintained home is packed with upgrades and designed for both comfortable living and entertaining. Major improvements include a new roof and expansive deck installed in 2021, new vinyl plank flooring throughout the entire home, a whole-house water softener system, updated well plumbing with a new pressure tank, and fresh paint throughout. The bright and inviting kitchen features classic white cabinetry, stainless steel appliances, generous counter space, and an open layout that flows seamlessly into the main living areas. Spacious rooms throughout the home provide flexibility for family living, guests, home offices, or hobby spaces. Step outside and discover your own private backyard retreat. The saltwater pool is perfect for cooling off on warm summer days, while the large deck offers plenty of space for grilling, entertaining, or simply relaxing and enjoying the peaceful setting. Nestled in one of Chesapeake Beach's most sought-after neighborhoods, this home offers the rare combination of community amenities, water privileges, modern updates, and exceptional outdoor living. With beach access and passes, Chesapeake Bay privileges, and a prime cul-de-sac location, 4416 Snowy Egret Court is the perfect place to enjoy the Maryland waterfront lifestyle.

4416 Snowy Egret Ct, Chesapeake Beach

Listing courtesy of Deep Roots Real Estate. Contact: 4439676687
$659,900
4 Beds ⋅ 3 Baths
BACK ON THE MARKET due to the buyer getting cold feet. ASSUMABLE 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 and truly move-in ready, this beautifully maintained 4-bedroom, 2.5-bath, 2-car garage home offers a rare opportunity to own a property where virtually every major system has already been upgraded. Simply move in, unpack, and enjoy. The heart of the home is a spacious kitchen featuring granite countertops, a center island, abundant cabinetry, and newer Samsung and KitchenAid appliances—perfect for everyday living and entertaining alike. Recent 2026 updates include fresh interior paint and bathroom enhancements, creating a bright, modern, and welcoming atmosphere throughout. What truly sets this home apart is the extensive list of recent capital improvements, including: • Rare 2.25% VA assumable mortgage (subject to lender approval) • Two new HVAC systems (2024/2025) • Brand-new deck (2026) • Smart Nest thermostats (2024/2025) • Roof replaced with architectural shingles (2017) • New water service line from meter to home (2023) • New 6" gutters and downspouts (2023) • New chimney cap (2025) • New garage door (2025) • New washer and dryer (2025) • Updated lighting throughout • Commercial-grade 2 HP garbage disposal • Newer Samsung appliances and KitchenAid dishwasher • Bathroom updates completed in 2026 The main level features rich hardwood flooring, soaring foyer and dining ceilings, oversized windows, and an inviting sunroom overlooking the backyard—ideal for morning coffee while watching families of deer sunbathe, reading, or gathering with family and friends. Upstairs, you'll find four generously sized bedrooms, including an impressive owner's retreat complete with walk-in closet, a private sitting area, and a spacious ensuite bath featuring a soaking tub and refreshed finishes. The finished lower level provides exceptional flexibility and can easily serve as a recreation room, media room, fitness area, home office, or additional entertaining space. Step outside to your private backyard retreat featuring a brand-new Trex deck and fenced yard—perfect for grilling, relaxing, entertaining, pets, or play. Residents of Richfield Station enjoy direct access to the Chesapeake Rail Trail System and Fishing Creek Boardwalk, while Chesapeake Beach residents also enjoy access to exceptional schools, sandy Bay beaches, waterfront dining, farmers markets, local shops, community events, playgrounds, and recreational amenities throughout the Twin Beaches. Conveniently located for commuters with easy access to Andrews Air Force Base, Annapolis, Washington, D.C., and major transportation routes, this home offers the perfect balance of coastal charm and everyday convenience. Not a townhouse or condominium. Quarterly HOA fee is only $84.

2425 Harrison Ct, Chesapeake Beach

Listing courtesy of Redfin Corp. Contact: 3016586186
$685,000
5 Beds ⋅ 4 Baths
Welcome to 3671 Middle Ground Court, where comfort, space, and the Chesapeake lifestyle come together in one exceptional home. This beautifully maintained traditional Colonial offers five bedrooms, three and a half bathrooms, and a thoughtfully designed floor plan that's perfect for everyday living and entertaining alike. Step inside to discover refreshed hardwood floors (2026), new carpet in the front living room (2026), and spacious living areas filled with natural light. The fully finished lower level expands your living space with brand-new flooring (2018), a full bathroom, and a versatile bonus room that's already wired for a theater system—ideal as a media room, home gym, or fifth bedroom. Outside, the fully fenced backyard provides a private retreat where children and pets can safely run and play, while the oversized attached two-car garage offers ample room for vehicles, storage, and hobbies. Recent updates provide peace of mind, including a new dishwasher (2024), privacy fence (2022), custom primary closet system (2021), and sump pump (2018), making this home truly move-in ready. Located just steps from Bayfront Park and Brownie's Beach, you'll love being able to walk to the waterfront, enjoy beach days, fossil hunting, stunning Chesapeake Bay sunsets, and all the charm that Chesapeake Beach has to offer. Don't miss this opportunity to settle into your new home just in time to enjoy everything summer on the Bay has to offer!

3671 Middle Ground Ct, Chesapeake Beach

Listing courtesy of Real Broker, LLC - Severna Park. Contact: 8445517325
$1,200,000
5 Beds ⋅ 4 Baths
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, D.C. Offering approximately 3,100 square feet, the main residence features five spacious bedrooms and four full bathrooms, along with a newly installed HVAC system for modern comfort while preserving its timeless character. Enjoy exceptional waterfront living with a commercial-style private pier featuring approximately 5 feet of water depth, deeper than most in the area, making it ideal for boating, fishing, and waterfront entertaining. Best of all, no flood insurance is required for this location. The property also includes a one-car garage and a livable studio with a full bathroom and kitchenette, ideal for a guest suite, private office, artist retreat, or bed-and-breakfast use. The entire third floor functions as a private apartment with its own separate exterior entrance. This fully self-contained suite includes a bedroom, living room, kitchenette, built-in washer and dryer, and a private balcony with breathtaking waterfront views, perfect for rental income, extended family, or independent guest accommodations. Ideally located within walking distance to the Chesapeake Beach Resort & Spa, as well as the boardwalk, marina, and a variety of waterfront attractions, this home offers easy access to nearby restaurants, shops, local entertainment, the water park, concerts, gaming, and seasonal events. Enjoy the best of coastal living with Bay breezes all summer long, historic charm throughout, and spectacular waterfront views from multiple rooms, including two bedrooms on the upper level. Rich with original heart of pine flooring, architectural character, and modern updates, this home stands apart from anything else on the Bay. Set on a block-long parcel that is nearly impossible to find, it offers space, privacy, and long-term value. Whether you are seeking a primary residence, vacation retreat, or income-producing investment, this truly rare Chesapeake Bay waterfront property delivers it all.

4011 27th St, Chesapeake Beach

Listing courtesy of Keller Williams Realty. Contact: (703) 679-1700
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