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$650,000

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.

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:

$459,900

**LESS THAN 2 MILES TO THE CHESAPEAKE BAY!** Live the Salt Life Year-Round in Chesapeake Beach! Situated on **1.28 private acres** and backing to woods, this home offers space, privacy and a fantastic location in **The Highlands**. Recent updates include **NEW LVP flooring – June 2026 * Stainless Steel Kitchen Appliances & Hot Water Heater – 2025 * Shed & Lower-Level Flooring – 2024 * Heat Pump – 2022 * Metal Roof – 2014.** Enjoy new flooring throughout the main level plus a **FULLY FINISHED LOWER LEVEL** offering plenty of additional living and entertaining space. The Highlands offers walking trails, playgrounds and sports courts with an HOA of only **$85/year**. Just minutes to the Twin Beaches and all the Chesapeake Bay lifestyle has to offer—beaches, marinas, fishing piers, boardwalks, restaurants, Farmers Market and more! Convenient to **D.C., Annapolis, Baltimore & Joint Base Andrews.** Great schools, great neighborhood, and your chance to enjoy Chesapeake Beach living!

3 Beds ⋅ 2 Baths

**LESS THAN 2 MILES TO THE CHESAPEAKE BAY!** Live the Salt Life Year-Round in Chesapeake Beach! Situated on **1.28 private acres** and backing to woods, this home offers space, privacy and a fantastic location in **The Highlands**. Recent updates include **NEW LVP flooring – June 2026 * Stainless Steel Kitchen Appliances & Hot Water Heater – 2025 * Shed & Lower-Level Flooring – 2024 * Heat Pump – 2022 * Metal Roof – 2014.** Enjoy new flooring throughout the main level plus a **FULLY FINISHED LOWER LEVEL** offering plenty of additional living and entertaining space. The Highlands offers walking trails, playgrounds and sports courts with an HOA of only **$85/year**. Just minutes to the Twin Beaches and all the Chesapeake Bay lifestyle has to offer—beaches, marinas, fishing piers, boardwalks, restaurants, Farmers Market and more! Convenient to **D.C., Annapolis, Baltimore & Joint Base Andrews.** Great schools, great neighborhood, and your chance to enjoy Chesapeake Beach living!

2811 Glasgow Way, Chesapeake Beach

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

$360,000

Opportunity to obtain a spacious home in a community with beach access. The Breezy Point Community has access to the beach through voluntary dues, not mandatory ones. The beautiful beach is within walking distance and also offers a large picnic area. The home is being sold as is by the estate. The special features include new carpet on the main level and a new roof between 2021 and 2022. Solar panels have been installed and will be paid in full at closing. The family is working on cleaning out the home, which is why we haven't displayed pictures of all the rooms. There are 2 bedrooms on the main level, and a 3rd bedroom was converted into a laundry/storage room. There is also a w/d hookup in the basement if you want to convert that room back to a bedroom. The lower level is partially finished and in need of renovation. There is a wood stove in the lower-level family room that heats the house during a cold spell. There are 2 spacious garages, currently full of belongings. The screened-in porch is large and great for entertaining. There is a covered area for parking 2 cars or grilling, and plenty of concrete driveway spaces for parking. The front yard is fenced in to keep the children and pets safe.

3 Beds ⋅ 2 Baths

Opportunity to obtain a spacious home in a community with beach access. The Breezy Point Community has access to the beach through voluntary dues, not mandatory ones. The beautiful beach is within walking distance and also offers a large picnic area. The home is being sold as is by the estate. The special features include new carpet on the main level and a new roof between 2021 and 2022. Solar panels have been installed and will be paid in full at closing. The family is working on cleaning out the home, which is why we haven't displayed pictures of all the rooms. There are 2 bedrooms on the main level, and a 3rd bedroom was converted into a laundry/storage room. There is also a w/d hookup in the basement if you want to convert that room back to a bedroom. The lower level is partially finished and in need of renovation. There is a wood stove in the lower-level family room that heats the house during a cold spell. There are 2 spacious garages, currently full of belongings. The screened-in porch is large and great for entertaining. There is a covered area for parking 2 cars or grilling, and plenty of concrete driveway spaces for parking. The front yard is fenced in to keep the children and pets safe.

4820 Sherwood Ave, Chesapeake Beach

Listing courtesy of O'Brien Realty ERA Powered. Contact: 3018632400

$685,000

BUYER failed to perform so we are BACK on the MARKET! Now is your opportunity! 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!

5 Beds ⋅ 4 Baths

BUYER failed to perform so we are BACK on the MARKET! Now is your opportunity! 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

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.

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

$515,000

Tucked into the sought-after Holiday Beach community in Chesapeake Beach, this classic colonial offers the perfect blend of comfort, charm, and the relaxed southern Maryland lifestyle so many buyers are searching for. Enjoy community water access along with easy proximity to all the dining, shopping, marinas, and recreation that make the Chesapeake Bay lifestyle so special. Inside, hardwood floors, plush carpeting, and a beautifully appointed kitchen create warm and inviting living spaces designed for both everyday living and entertaining. Formal living and dining rooms flank the dramatic two-story foyer, while the eat in kitchen is the perfect place to unwind and take in peaceful wooded views that surround the home from every room. Upstairs, the spacious primary suite features a walk-in closet and private full bath, complemented by two generously sized secondary bedrooms and an additional hall bath. The unfinished walk-out lower level provides endless possibilities for future expansion, recreation space, or storage — ready for your personal vision and finishing touches. Located just minutes from local favorites, waterfront dining, beaches, boating, and the highly anticipated reopening of the Chesapeake Beach Water Park in 2027, this home offers a lifestyle that feels worlds away from the city while remaining convenient to everything you need.

3 Beds ⋅ 3 Baths

Tucked into the sought-after Holiday Beach community in Chesapeake Beach, this classic colonial offers the perfect blend of comfort, charm, and the relaxed southern Maryland lifestyle so many buyers are searching for. Enjoy community water access along with easy proximity to all the dining, shopping, marinas, and recreation that make the Chesapeake Bay lifestyle so special. Inside, hardwood floors, plush carpeting, and a beautifully appointed kitchen create warm and inviting living spaces designed for both everyday living and entertaining. Formal living and dining rooms flank the dramatic two-story foyer, while the eat in kitchen is the perfect place to unwind and take in peaceful wooded views that surround the home from every room. Upstairs, the spacious primary suite features a walk-in closet and private full bath, complemented by two generously sized secondary bedrooms and an additional hall bath. The unfinished walk-out lower level provides endless possibilities for future expansion, recreation space, or storage — ready for your personal vision and finishing touches. Located just minutes from local favorites, waterfront dining, beaches, boating, and the highly anticipated reopening of the Chesapeake Beach Water Park in 2027, this home offers a lifestyle that feels worlds away from the city while remaining convenient to everything you need.

4010 Beach Dr, Chesapeake Beach

Listing courtesy of Paul Wesley Real Estate. Contact: 7032822709

$190,000

This property is being sold as-is and is perfect for investors, flippers, or buyers looking for a renovation opportunity. With solid bones and endless potential, this home is a blank canvas ready for your vision. Whether you’re looking to fix and flip, hold as a rental, or bring new life to a great location—this is the one. Cash, hard money, or renovation loan preferred. Don’t miss this chance to invest in a property with serious upside!

3 Beds ⋅ 2 Baths

This property is being sold as-is and is perfect for investors, flippers, or buyers looking for a renovation opportunity. With solid bones and endless potential, this home is a blank canvas ready for your vision. Whether you’re looking to fix and flip, hold as a rental, or bring new life to a great location—this is the one. Cash, hard money, or renovation loan preferred. Don’t miss this chance to invest in a property with serious upside!

6231 8th St, Chesapeake Beach

Listing courtesy of Samson Properties. Contact: 7033788810

$799,000

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!

2 Beds ⋅ 1 Baths

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!

3713 & 3711 Bayview Dr, Chesapeake Beach

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$759,900

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!

3 Beds ⋅ 5 Baths

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!

8048 Windward Key Dr, Chesapeake Beach

Listing courtesy of Compass. Contact: (410) 429-7425

$749,900

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.

4 Beds ⋅ 5 Baths

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.

8076 Windward Key Dr, Chesapeake Beach

Listing courtesy of RE/MAX Realty Group. Contact:

$774,900

MAJOR PRICE IMPROVEMENT. 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.

4 Beds ⋅ 5 Baths

MAJOR PRICE IMPROVEMENT. 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.

8054 Windward Key Drive, Chesapeake Beach

Listing courtesy of RE/MAX Realty Group. Contact:

$179,000

Build you coastal escape! Large Corner lot is perfectly situated in new 4 lot community ready for your custom dream home. Imagine weekends spent exploring the boardwalk, beaches, crabbing, charter boat fishing or just enjoying the many local restaurants. Bring your builder and start experiencing the Chesapeake Bay lifestyle you've always imagined.

Lot 22R Block 8, 18th St, Chesapeake Beach

Listing courtesy of RE/MAX One. Contact: 4105356291

$99,000

Your chance to build your dream home above it all. Perched on a hill in the coveted Chesapeake Beach area, this nearly 1/2 acre lot offers an unparalleled lifestyle. You're just minutes to the Boardwalks, beach, resort style dining, charter fishing, and more! Don't miss this rare opportunity. Come see the potential for yourself.

Lot 22R Block 7, 18th St, Chesapeake Beach

Listing courtesy of RE/MAX One. Contact: 4105356291

$199,000

Your Private Sanctuary Awaits! Escape to this exclusive, wooded retreat. Imagine building your dream home nestled among mature trees, just moments from the best of the Chesapeake Bay. Whether it's a morning stroll on the boardwalk, a day of crabbing and fishing or an evening of dining and entertainment, everything is at your fingertips. This is more than a lot; it's your gateway to endless coastal fun. Previous Percs but will need new. Buyer to confirm all with county.

Lot 30 A, Block 6, 18th Street, Chesapeake Beach

Listing courtesy of RE/MAX One. Contact: 4105356291

$699,999

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.

4 Beds ⋅ 3 Baths

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.

8314 Bayside Rd, Chesapeake Beach

Listing courtesy of JPAR Real Estate Professionals. Contact: 3016844895

$165,000

PRICE IMPROVEMENT on this amazing lot in Chesapeake Beach. Rare opportunity to build your custom home on a prime lot with Chesapeake Bay views. Located at 8314 Bayside Road, this property offers year-round water views, coastal charm, and the convenience of public water, sewer hookups, and electric availability. Relax on your new front porch soaking in the bay breeze and peaceful surroundings. Enjoy easy access to the North Beach boardwalk, marinas, Brownie’s Beach, and local restaurants. Create your ideal waterfront lifestyle while remaining conveniently located near Annapolis, Washington, D.C., Andrews AFB, Baltimore, and Northern Virginia. Build your vision in Chesapeake Beach!

8314 Bayside Rd, Chesapeake Beach

Listing courtesy of JPAR Real Estate Professionals. Contact: 3016844895

$390,000

This is the chance to own your own private woodland sanctuary at the end of a peaceful, quiet cul-de-sac. This enchanting home is truly an artist’s dream, bathed in dappled sunshine and offering a level of tranquility that is hard to find. The interior serves as a creative canvas, currently featuring vibrant custom murals that can remain to inspire the next owner or be returned to a neutral palette��the choice is yours. Beyond its charming exterior, the home offers significantly more space than appears, boasting a versatile layout with two distinct living areas: a shared living space on the upper level and a spacious secondary living room downstairs. The heart of the home is the beautifully updated kitchen, complete with modern stainless steel appliances and stylish finishes. Durable LVP flooring flows throughout the main living areas, while carpeting adds comfort to the bedrooms. This expansive floor plan includes six true bedrooms with two separate living spaces. The upper level features three bedrooms, including a primary suite that serves as a private getaway with its own turf-covered walk-out deck overlooking the trees. For added convenience, the laundry is also located on the upper bedroom level. The lower level provides excellent separation of space with three additional spacious rooms that can be used for sleeping or are perfect for a home office, playroom, or studio. There is a wet bar rough-in in the lower family room to make this a great hangout spot, or create another Kitchen for a basement apartment with private rear entrance. Major updates provide peace of mind, including two updated bathrooms and a brand-new well pump installed in 2024. Outside, the backyard is primed and ready for a custom patio, offering the perfect spot to host gatherings or simply enjoy the surrounding nature. Combining modern updates, significant financial value, and a serene atmosphere, this home is a rare find for those seeking both function and inspiration.

6 Beds ⋅ 2 Baths

This is the chance to own your own private woodland sanctuary at the end of a peaceful, quiet cul-de-sac. This enchanting home is truly an artist’s dream, bathed in dappled sunshine and offering a level of tranquility that is hard to find. The interior serves as a creative canvas, currently featuring vibrant custom murals that can remain to inspire the next owner or be returned to a neutral palette��the choice is yours. Beyond its charming exterior, the home offers significantly more space than appears, boasting a versatile layout with two distinct living areas: a shared living space on the upper level and a spacious secondary living room downstairs. The heart of the home is the beautifully updated kitchen, complete with modern stainless steel appliances and stylish finishes. Durable LVP flooring flows throughout the main living areas, while carpeting adds comfort to the bedrooms. This expansive floor plan includes six true bedrooms with two separate living spaces. The upper level features three bedrooms, including a primary suite that serves as a private getaway with its own turf-covered walk-out deck overlooking the trees. For added convenience, the laundry is also located on the upper bedroom level. The lower level provides excellent separation of space with three additional spacious rooms that can be used for sleeping or are perfect for a home office, playroom, or studio. There is a wet bar rough-in in the lower family room to make this a great hangout spot, or create another Kitchen for a basement apartment with private rear entrance. Major updates provide peace of mind, including two updated bathrooms and a brand-new well pump installed in 2024. Outside, the backyard is primed and ready for a custom patio, offering the perfect spot to host gatherings or simply enjoy the surrounding nature. Combining modern updates, significant financial value, and a serene atmosphere, this home is a rare find for those seeking both function and inspiration.

6337 Dory Ct, Chesapeake Beach

Listing courtesy of Hyatt & Company Real Estate LLC. Contact: 4107056296

$55,000

This Does have a old well on it. It will need to be perc for septic. Nice flat lot to build on close to the beach in Randle Cliff area. Close to shopping/beach/ waterpark.

4200 Chesapeake Ave, Chesapeake Beach

Listing courtesy of Samson Properties. Contact: 4439757555

$136,900

Beach and pier access on the Chesapeake Bay. Wooded 1.75± acre homesite with a partial water view. Located in an established waterfront community offering natural privacy and coastal ambiance.

4685 Camp Roosevelt Dr, Chesapeake Beach

Listing courtesy of Home Towne Real Estate. Contact: 8882252736

$90,000

Incredible value in Northern Calvert County! Priced aggressively at $90,000, this perced and private 3 acre lot offers a rare chance to secure a buildable homesite well below market value. To achieve a fully buildable status, the buyer will need to complete the final subdivision process (estimated at $25k and roughly 12 months to process) and handle the TDR allocation (estimated at $30k). With an all-in land investment of approximately $145,000, the equity potential here is unmatched for the northern end of the county. Perfect for a savvy buyer or builder looking to lock in a great price now while finalizing their custom home plans over the next year.

3164 Dalrymple Rd, Chesapeake Beach

Listing courtesy of RE/MAX One. Contact: 4105356291