The Highlands Homes for Sale

The Highlands Homes for Sale

Welcome to The Highlands, a picturesque subdivision nestled in the charming coastal town of Chesapeake Beach, Maryland. This delightful community offers a unique blend of tranquility and accessibility, making it the perfect place for families, retirees, and anyone looking to embrace a serene lifestyle by the bay.

The Highlands is characterized by its beautifully designed homes that seamlessly blend modern amenities with classic architectural charm. Whether you’re searching for a cozy cottage or a spacious family residence, you’ll find an array of homes for sale that cater to diverse tastes and lifestyles. Many properties feature stunning waterfront views, expansive backyards, and open-concept layouts that create an inviting atmosphere for entertaining or simply unwinding after a long day.

Living in The Highlands means enjoying the best of both worlds: a peaceful retreat just minutes away from the vibrant Chesapeake Beach community. Residents can indulge in a variety of local attractions, including sandy beaches, charming shops, and delectable dining options. Outdoor enthusiasts will appreciate the proximity to parks, hiking trails, and water activities, all set against the backdrop of the stunning Chesapeake Bay.

With a strong sense of community and a welcoming atmosphere, The Highlands is more than just a place to live; it’s a place to call home. If you’re ready to discover your dream home in this idyllic subdivision, explore the available homes for sale today and take the first step towards a lifestyle filled with comfort, beauty, and endless possibilities. Welcome to your new beginning in The Highlands!

Newest The Highlands Homes for Sale

4 Beds ⋅ 3 Baths

LIVE FOR SHOWINGS BEGINNING 7/31 * This home will WOW you from the moment you arrive! Located in The Highlands community of Chesapeake Beach, this beautifully remodeled home offers over 2,500 square feet of finished living space on more than 1/2 acre. Featuring 4 bedrooms, 3 full bathrooms, and a stunning list of updates, this is the home with all the FLASH your buyers have been waiting for! The beautifully renovated kitchen is the heart of the home, showcasing a gas range, oversized island, elegant quartzite countertops, and modern finishes throughout. Walk in Pantry * Built Ins * And a Primary Suite to Die For * Spa Like BA * Ceiling Fans * And Style the Likes of HGTV * The fully finished lower level provides additional living space and features a cozy pellet stove — perfect for relaxing evenings, movie nights, or entertaining guests. **See Doc Section for FULL LIST of UPDATES AND UPGRADES ** Step outside and enjoy the spacious composite deck overlooking the private yard, ideal for gatherings, grilling, and enjoying the peaceful surroundings. The exterior stands out with 4 garage spaces — including 2 attached garages plus an oversized detached garage/workshop offering endless possibilities for vehicles, hobbies, and storage. Nestled in a fantastic neighborhood with walking/riding paths, tot lot, Sport Courts, this home offers the perfect blend of comfort, convenience, and coastal living. HOA is only $85/Year * All THIS and Located less than a mile from the Chesapeake Bay and all that the Twin Beaches have to offer, enjoy nearby restaurants, shopping, excellent schools, public beaches, boardwalks, fishing piers, marinas, and Rod N Reel Resort & Spa. Live the Salt Life year-round while still enjoying an easy commute to Washington, DC, Annapolis, and Baltimore. Don’t miss this incredible opportunity to own a beautifully updated home in one of Chesapeake Beach’s most desirable communities!

8541 Saint Andrews Dr, Chesapeake Beach

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

4 Beds ⋅ 3 Baths

7935 Pipers Path, Glen Burnie

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

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

5 Beds ⋅ 3 Baths

Welcome to 222 Royal Arms Dle, a spacious and beautifully maintained single-family home in the heart of Glen Burnie, offering the perfect blend of comfort, functionality, and convenience—with no HOA restrictions. Boasting 5 bedrooms and 3 full bathrooms, this home provides ample space for growing families, multi-generational living, or those needing extra room for guests or a home office. The thoughtfully designed layout features bright and inviting living spaces, generous bedroom sizes, and versatile areas to fit your lifestyle. The lower level offers a cozy retreat complete with a charming fireplace, creating the perfect setting for movie nights, entertaining, or relaxing after a long day. Step outside to enjoy the spacious rear deck, ideal for summer barbecues, outdoor dining, or simply unwinding while overlooking the backyard. Conveniently located near shopping, dining, parks, and major commuter routes including I-97, Route 100, and Route 10, this home offers easy access to Baltimore, Annapolis, Fort Meade, and Washington, D.C. With its generous living space, desirable features, and no HOA, 222 Royal Arms Dle presents an incredible opportunity to enjoy the freedom of homeownership in a sought-after Glen Burnie location. Schedule your private tour today and discover all this exceptional property has to offer. **Solar Panels are leased.

222 Royal Arms Dle, Glen Burnie

Listing courtesy of Compass. Contact: (202) 386-6330

3 Beds ⋅ 2 Baths

Experience the Salt Life year-round on 1.28 private acres—where space, privacy, and coastal living come together. * This home offers a cozy blend of comfort, privacy, and convenience. Backing to woods and featuring a large, private backyard, it's a peaceful setting while remaining close to everything the area has to offer. And nestled in a Fantastic Neighborhood. Recent updates include: New Luxury Vinyl Plank (LVP) Flooring – June 2026; New Hot Water Heater – 2025; New Stainless Steel Kitchen Appliances – 2025; New Shed – 2024; New Heat Pump – 2022; Metal Roof – 2014 * Inside, you'll find new flooring throughout the main level and a finished lower-level offering additional living and entertaining space. LL flooring New in 2024. The Highlands feature walking trails, playgrounds, sports courts, only $85/year HOA. Less than 2 miles from the Twin Beaches, you'll love LIVING the coastal CHESAPEAKE BAY lifestyle this area provides, including public beaches, marinas, fishing piers, 3 boardwalks, a variety of local restaurants and pubs, the Rod 'N' Reel Resort & Spa, and the area's beautiful new public library * Weekly Farmers Market * Easy Commute to Washington, D.C., Annapolis, Baltimore, and Joint Base Andrews. Calvert County is known for the Best Schools

2811 Glasgow Way, Chesapeake Beach

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

3 Beds ⋅ 2 Baths

Fabulous opportunity to own this well-maintained 3-bedroom, 2-bath split foyer in the desirable Highlands community of Chesapeake Beach! Situated on one of the best lots in the neighborhood, this home backs to woods and features a large, level backyard fully fenced with a privacy wood fence and rear chain-link fence with gate—perfect for pets, play, and outdoor enjoyment. The updated kitchen offers white cabinetry, stainless steel appliances, LVP flooring, and access to the spacious rear deck overlooking the private backyard. Hardwood flooring extends throughout the living room, hallway, and bedrooms on the upper level. Two bedrooms and a full bath are located upstairs, while the lower level features a large third bedroom, and a second full bath with tiled walk-in shower. Lower level also has a laundry area with washer and dryer, and a spacious rec room with LVP flooring and newer sliding glass doors leading to the backyard. Additional features include a one-car garage, ample parking, and an unbeatable location within walking distance of the community recreation area that has a playground, basketball court, ball field, and walking/jogging trails. Conveniently located in an area of top-rated schools and just minutes from beaches, marinas, shopping, and restaurants. Easy commute—only approximately 35 minutes to Joint Base Andrews and Washington, D.C.!

2735 Braeburn Ln, Chesapeake Beach

Listing courtesy of Keller Williams Flagship. Contact:

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