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8076 Windward, Chesapeake Beach
$724,900
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, Chesapeake Beach

Listing courtesy of RE/MAX Realty Group. Contact:

13908 Victory Ln, Solomons
$649,000
3 Beds ⋅ 3 Baths
Only a few homes in this community come with an upper level with guest rooms and full bath (THIS IS ONE OF THEM). This home features on main level: Primary Suite with two walk in closets, Luxury full bath with Walk-in Glass shower, and separate sink vanities. The kitchen is complete with Stainless Steel appliances, granite counter tops, deep stainless steel sink, tile backsplash, center island with breakfast bar, upgraded 42"cabinetry and large pantry. The family room boasts a gas fireplace conveniently located off the kitchen and also a walk-out to the large screened-in porch with ceiling fan. On this level you will also find the separate formal dining room which is currently being used as a home office/library, a powder room for guests, a large laundry room with wash basin and entry to the two car garage with garage door opener. Hardwood flooring and upgraded lighting on both the main and upper levels of this home. The crown molding package throughout this home is incredible. Upstairs you will find additional living space with a flex room/loft area with two additional large bedrooms and a full bath. The lower basement level is ready for your finishing touches and does have a rough in for future full bath. Other features for this property are rear paver patio off screened-in porch, custom blinds and drapery, and lighting package throughout. Community amenities include a clubhouse, fitness center, swimming pool, community pier for fishing and crabbing, kayak/canoe launch, sidewalks, manicured common areas, and a marina offering discounted boat storage and slips. HOA fees also include personal lawn care, ensuring a truly maintenance-free lifestyle. Located in a 55+ community (with up to 20% of homes available for residents under 55 with other restrictions still applying), this home offers the perfect blend of comfort, convenience, and coastal charm. Enjoy close proximity to PAX River Naval Air Station, Historic Solomons Island, fine dining, beaches, boardwalks, shopping, parks, museums, concert venues, local wineries, and theaters—everything Southern Maryland has to offer. Every detail of this home reflects the builder’s pride and attention to excellence, making 13908 Victory Lane in Solomons a true showcase property.

13908 Victory Ln, Solomons

Listing courtesy of RE/MAX One. Contact:

11005 Poplar Dr, Lusby
$415,000
3 Beds ⋅ 4 Baths
Unique Coastal Opportunity – A Rare Find - Cove Point Beach! Discover the potential of this one-of-a-kind property, ideally situated on a desirable corner lot just one block from Cove Point Beach and the iconic Cove Point Lighthouse. Brimming with character and decades of cherished memories, this nostalgic family retreat offers two separate living spaces—perfect for extended family, rental income, or a private coastal getaway. The left side features a 2-bedroom, 1-bath apartment complete with an enclosed porch and a fireplace (unused in recent years). The right side includes a 1-bedroom apartment, enhanced by a permitted second-story addition (built in 2009). The upper level—designed as a spacious great room or creative studio—can be accessed via a spiral staircase or directly from the deck. (Note: no additional bedrooms were permitted on the second floor.) Additional highlights include: Detached garage—ideal for storing a golf cart or beach gear Classic “crab shack” perfect for entertaining, crab feasts, and gatherings Outdoor shower for easy beach living Shared central utility area with HVAC, propane heat, washer/dryer, and a functional half bath . Both main-level apartments have been rented independently in the past, offering excellent income potential.. An incredible opportunity to create your own coastal haven or investment property in a sought-after beachside location. Imagine the possibilities and start living the beach lifestyle you’ve always dreamed of !

11005 Poplar Dr, Lusby

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

12830 H G Trueman Rd, Solomons
$198,430
**Versatile Property in Solomons Town Center** Unlock a world of possibilities with this versatile property in the heart of Solomons Town Center. Ideal for multiple uses, this prime lot can accommodate commercial, residential, multi-family, and business opportunities. With public water and sewer hook-ups available, the infrastructure is in place to support a variety of developments. Located just over an hour from Washington, D.C., Virginia, and Baltimore, this property offers convenience and accessibility for both personal and professional endeavors. The owner is open to considering owner financing with the right terms and conditions, providing an excellent opportunity for those looking to invest. Don't miss out on the chance to create something extraordinary in one of Maryland's most vibrant communities. Feel free to tailor it further to meet your specific needs!

12830 H G Trueman Rd, Solomons

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

3971 Oyster House, Broomes Island
$259,900
5 Beds ⋅ 1 Baths
This distinctive A-frame property presents a compelling investment opportunity, ideally located near Island Creek—a peaceful canal that enhances the area’s charm and appeal. Offering 1,764 finished square feet, the home features five spacious bedrooms and one full bathroom, making it adaptable for a variety of uses, including long-term rentals or vacation stays. Situated on a generous 0.38-acre lot, the property includes a screened-in porch and ample outdoor space for relaxing or entertaining. The home is in need of significant renovations, providing the perfect canvas for investors or buyers with vision to restore and customize it to their preferences. While it is not directly waterfront, access to the nearby canal offers a unique advantage for outdoor enthusiasts and those seeking a serene environment. Properties near water often command higher interest, stronger rental potential, and long-term appreciation. Additional features such as the existing fireplace add character and warmth, while off-street parking ensures convenience for residents and guests. The aluminum siding contributes to lower maintenance requirements over time. Beyond its investment potential, this property also presents an excellent opportunity to be transformed into a private residence. With thoughtful updates and improvements, it can become a charming and personalized home in a desirable, nature-oriented setting. Whether pursuing rental income or creating a private retreat, this property offers substantial upside and long-term value. Property being sold AS IS.

3971 Oyster House, Broomes Island

Listing courtesy of Samson Properties. Contact:

3045 Holland Cliffs Rd, Huntingtown
$1,375,000
7 Beds ⋅ 4 Baths
Discover an extraordinary opportunity for waterfront living on the Patuxent River. This stunning brick-front residence offers 7 bedrooms, 4 full bathrooms, and a private 2-bedroom guest apartment with full kitchen and separate entry. Designed with comfort and accessibility in mind, the home features an elevator serving all three levels, expansive entertaining areas, and a sparkling pool with maintenance-free decking. An oversized 3-car garage, multiple sheds, and two laundry rooms provide outstanding functionality. The outdoor amenities are unmatched — a private paved access road leads to the shoreline with deep-water pier, dual boat lifts, and jet ski lift, ideal for boating enthusiasts. Additional highlights include an all-seasons room, wood-burning fireplace, new roof (2022), new hot water heater (2023), new septic system with nitrogen removal (2023), new well (2024), and a brand-new pool liner (2024). With panoramic river views, modern upgrades, and an incomparable setting, this property offers the perfect blend of luxury, versatility, and privacy — all just minutes from major commuter routes.

3045 Holland Cliffs Rd, Huntingtown

Listing courtesy of TTR Sotheby's International Realty. Contact:

3944, 3946, & 3935 Oyster House, Broomes Island
$1,900,000
MOTIVATED SELLER - BRING ALL OFFERS. Discover a premier investment opportunity in the heart of Broomes Island, offering a waterfront destination that perfectly embodies the Chesapeake lifestyle. Spanning over 3 acres across three separate tax parcels, this expansive mixed-use assembly overlooks the Patuxent River and Island Creek, situated just minutes from the Chesapeake Bay and the affluent D.C. market. The centerpiece at 3944 Oyster House Road features a 6,208 +/- SF full-service restaurant and 28-slip marina. The restaurant accommodates approximately 300 guests across multiple dining levels-including a loft and waterfront decks-and includes an outdoor "boat bar," extensive kitchen facilities with outdoor cold storage, and a large adjoining parking lot. All furniture, fixtures, and equipment are included in the sale. The potential for diverse revenue continues at 3946 Oyster House Road, a 1.39-acre waterfront commercial lot improved by a 5,000 +/- SF tented venue specifically designed for high-end events and parties, supported by a dedicated storage and cooking building. Complementing the commercial assets are two distinct residential properties: the fully furnished Broomes Island Inn, a two-story Bed & Breakfast featuring 4 bedrooms and dual kitchens/laundry facilities, and 3935 Oyster House Road, a furnished two-unit waterview home on a corner lot ideal for long-term rentals or staff housing. With multiple income streams and a dominant position in the local maritime landscape, this property offers unparalleled hyper-local authority for a savvy investor.

3944, 3946, & 3935 Oyster House, Broomes Island

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

11378 Sitting Bull Trl, Lusby
$5,100
INCREDIBLE LAND OPPORTUNITY – JUST $6,300! Looking for an affordable piece of land with potential building possibilities? Take a look at this approximately 0.23-acre residential lot in Chesapeake Ranch Estates! The property has a history of previous percolation testing, making it an interesting opportunity for someone looking to build in the future. Public water hookup is identified as available, and the property also offers a lake view and lake frontage. Whether you're a future homeowner, builder, or investor, this is an affordable opportunity to secure land in an established Lusby community. At just $6,300, don't overlook the possibilities! Previous perc history does not constitute current septic approval. Buyer to independently verify all information, including current perc/septic suitability, building feasibility, zoning, water hookup costs, HOA requirements, and all necessary county approvals.

11378 Sitting Bull Trl, Lusby

Listing courtesy of RE/MAX One. Contact:

5 Cross Point Dr, Owings
$1,100,000
6 Beds ⋅ 5 Baths
Rare opportunity! Former Kaine Homes model offering four finished levels, flexible living space, and an unbeatable location on the Calvert County / Anne Arundel County line. This impressive 6-bedroom, 4.5-bath home features a dramatic two-story foyer and family room with floor-to-ceiling windows and stone gas fireplace, hardwood floors, and a private library with French doors and built-ins. The gourmet kitchen opens to the family room and includes granite counters, gas cooktop, built in microwave and wall oven, dishwasher, two walk-in pantries, and generous counter seating, plus a breakfast room leading to maintenance-free decking overlooking trees. The main level also includes a formal dining room, elegant sitting area/living room, and convenient guest half bath, creating the perfect layout for everyday living and entertaining. The upper level primary suite offers a private bath, tray ceiling, sitting area with built-ins, walk-in closet plus two additional closets. Three additional spacious bedrooms complete the level, including two bedrooms connected by a Jack-and-Jill bath, each with walk-in closets. A unique four-level layout continues with a private fourth-level suite with bedroom, sitting area, built-ins, and full bath. The lower level apartment with separate entrance features a gourmet kitchen with Thermador commercial gas range, family room, dining area, bedroom, and full bath—ideal for multi-generational living, rental potential, or a home-based business. Don't miss the area off the main level with laundry and mud room, separate entrance and a second office and home gym offering even more potential. See floor plans for the full picture of the layout. Enjoy the wrap-around covered porch with gazebo, professional landscaping, spacious two-car garage, and ample concrete driveway parking. Located in the Northern High School district (Windy Hill Elementary & Middle) and convenient to DC, Annapolis, and Baltimore. Versatile, spacious, and beautifully designed—this home offers endless possibilities! 🏡

5 Cross Point Dr, Owings

Listing courtesy of Home Towne Real Estate. Contact:

8236 Bayside Rd, Chesapeake Beach
$549,000
4 Beds ⋅ 2 Baths
Beach living at its best in the heart of Chesapeake Beach, with bay views right from your deck. 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.

8236 Bayside Rd, Chesapeake Beach

Listing courtesy of Coldwell Banker Realty. Contact:

2160 Sixes Rd, Prince Frederick
$229,000
Exceptional opportunity to own 18.53 acres of perced land in beautiful Calvert County. This expansive parcel offers privacy, flexibility, and incredible long-term potential. Zoned RUR (Rural), the property may be used for agricultural purposes including farming, making it ideal for homesteading, recreational use, investment, or creating a private estate setting. Current zoning permits one dwelling per 20 acres. Buyers are encouraged to conduct their own due diligence with Calvert County regarding zoning regulations, land use, building restrictions, and the possibility of a variance. Seller financing available, providing flexible purchasing options. Very motivated seller — bring your offers! Whether you're looking to build, farm, invest, or secure acreage for the future, this property offers space, opportunity, and value.

2160 Sixes Rd, Prince Frederick

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

11624 Deadwood Dr, Lusby
$449,000
3 Beds ⋅ 3 Baths
Lakefront Living on a Spacious 18,000 Sq Ft Lot with Private Dock Access Welcome to this beautifully situated 3-bedroom, 3-bath lakefront rambler located in the amenity-rich community of Chesapeake Ranch Estates, offering low HOA fees and a true waterfront lifestyle. Set on an expansive 18,000 sq ft lot, this home features direct lake access with its own private dock equipped with a ladder for easy entry—perfect for swimming, fishing, kayaking, paddle boarding, or simply relaxing on the water. Enjoy serene lake views from the oversized deck, ideal for entertaining or taking in the natural surroundings, including sightings of osprey, eagles, and other migratory birds. A large paved driveway provides ample parking, while the lower-level patio offers additional outdoor space for barbecues and peaceful afternoons. Community amenities include access to two private beaches, a lakefront beach, playgrounds, community gardens, an airstrip, and year-round activities for residents. Conveniently located near schools, shopping, and restaurants, and approximately one hour from Joint Base Andrews, 15 minutes to Solomons Island, and close to Naval Air Station Patuxent River. Enjoy four seasons of waterfront living in a peaceful, resort-style setting. House is Virtually Staged.

11624 Deadwood Dr, Lusby

Listing courtesy of RLAH @properties. Contact:

2020 Chaneyville Rd, Owings
$700,000
Prime high visibility commercial opportunity located at a major stoplight with strong daily traffic counts from both local residents and visitors. Currently operated as a very successful automobile service business, this 2,400 square foot 40x60 building offers exceptional exposure and accessibility in a high traffic corridor. The building features three roll up service doors, welcoming main entrance space, private office, two bathrooms, and extensive upper level storage. Property is equipped with propane heat, air conditioning, and 200 amp electrical service. This unit is part of a condominium association with fee covering trash pick up, septic maintenance, well maintenance, snow removal, grass cutting, and exterior building insurance. Zoned RC Rural Commercial District, allowing flexible permitted and conditional uses including retail and personal service businesses, agricultural support enterprises, commercial greenhouses, agritourism ventures, professional offices, pet grooming, kennels, daycare operations, and online retail businesses. Seller is open to selling the building along with the auto repair equipment. List price reflects building only. Outstanding opportunity to grow or relocate your business in a highly visible, light controlled intersection with steady traffic and strong exposure.

2020 Chaneyville Rd, Owings

Listing courtesy of EXP Realty, LLC. Contact:

4180 Old Town Rd, Huntingtown
$399,999
High-Visibility Versatile Commercial Property | Close Highway Access Ideally situated for owner-users or investors, this 1948-built property offers a proven track record as a successful production and retail site. Former engraving, apparel printing, and embroidery business. Ready for its next chapter as a professional office, creative studio, light-production facility, or many other uses. Main Level: 4 rooms + half bath; ideal for showroom, reception, or primary workspace. Second Level: 3 private rooms + full bath; perfect for administrative offices or executive suites. Bonus Space: Large attic suitable for inventory storage or conversion to a creative loft. Parking & Access: Large dedicated parking pad for 5+ vehicles. Just off of Rt. 4 for easy client access or distribution.

4180 Old Town Rd, Huntingtown

Listing courtesy of RE/MAX One. Contact:

6045 Bayview Rd, Saint Leonard
$349,900
3 Beds ⋅ 2 Baths
*PRICE IMPROVEMENT! Nestled in a serene bayblock setting, this exquisite raised ranch, 3 bedroom, 1.5 bath home offers a harmonious blend of modern luxury and timeless comfort. With a major renovation completed in 2026, every corner of this residence has been thoughtfully designed to elevate your lifestyle. Step inside to discover an inviting open floor plan that seamlessly connects the living, dining, and kitchen areas. The spacious living room with heavy duty luxury vinyl tile flooring and recessed lighting, creates a warm ambiance perfect for both relaxation and entertaining. The gourmet kitchen is a chef's dream, featuring upgraded quartz countertops, an island for casual dining, and high-end stainless steel appliances, including a built-in microwave, dishwasher, and electric range. This home boasts three generously sized bedrooms, including a primary suite with an en-suite bath, ensuring privacy and comfort. An attic offers extra storage space, while the main floor laundry hookups add to the home's practicality. Outside, the property is equally enchanting. The 0.12-acre lot features a cleared front and rear yard, perfect for outdoor activities or simply enjoying the tranquility of your surroundings. Lush trees and manicured lawns provide a picturesque backdrop, while the bay views invite you to unwind and appreciate nature's beauty. Just two blocks away, the Chesapeake Bay offers private access for fishing enthusiasts and water lovers, enhancing your outdoor lifestyle. Located in a desirable area, this home combines the charm of a peaceful neighborhood with the allure of waterfront living. Enjoy leisurely strolls along the bay, or take advantage of the navigable waters for boating and exploration. On-street parking ensures convenience for you and your guests. This property is not just a home; it's a lifestyle. Experience the perfect blend of luxury, comfort, and nature in this stunning residence, where every detail has been curated for your enjoyment. Embrace the exclusive lifestyle that awaits you in this remarkable bayblock retreat.

6045 Bayview Rd, Saint Leonard

Listing courtesy of Five Star Real Estate. Contact:

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