The Highlands Homes for Sale

Welcome to The Highlands, a picturesque subdivision nestled in the charming town of Chesapeake Beach, Maryland. Located in Calvert County, this serene community offers a perfect blend of natural beauty and modern living, making it an ideal destination for families, retirees, and anyone looking to escape the hustle and bustle of city life.

The Highlands boasts an array of stunning homes for sale, each designed to cater to diverse tastes and lifestyles. From cozy single-family homes to spacious modern residences, there’s something here for everyone. Many properties feature beautiful landscaping, contemporary finishes, and open-concept layouts that invite natural light and warmth. Imagine sipping your morning coffee on a sun-drenched porch or hosting gatherings in a spacious backyard surrounded by lush greenery.

One of the highlights of living in The Highlands is its proximity to the breathtaking Chesapeake Bay. Residents can enjoy a variety of outdoor activities, from boating and fishing to hiking along scenic trails. The nearby beaches provide an excellent spot for relaxation and family fun, making every day feel like a vacation.

Additionally, The Highlands is conveniently located near local shopping, dining, and entertainment options, ensuring you have everything you need within reach. With its friendly community atmosphere and beautiful surroundings, The Highlands is not just a place to live; it’s a place to thrive.

Explore our current listings and discover your dream home in The Highlands today! With homes for sale that offer both comfort and style, your perfect haven awaits in this idyllic Chesapeake Beach community.

Newest The Highlands Homes for Sale

$1,900,500

4 Beds ⋅ 4 Baths ⋅ PABU2130138 MLS ⋅ ACTIVE Status

This distinctive custom home is located just minutes from historic Newtown and Yardley Boroughs. It is part of an enclave of just 10 homes, offering a rare combination of space, natural beauty and convenience. You will know you are home as you enter the THE HIGHLANDS community. This exceptional homesite encompasses 10 beautiful acres in the heart of Upper Makefield. Take some time to sit on the covered front porch and enjoy the tranquil setting. Double front doors welcome you to a hardwood-floored entrance with an immediate view of the dramatic family room. This inviting gathering space features a soaring floor-to-ceiling stone fireplace and custom-designed book and display shelving with a library-style sliding ladder which adds warmth and character to this room. Direct access to the large deck creates an ideal setting for outdoor entertaining. From here, the home unfolds to the formal dining room. Generous in size, it is well suited for special holiday meals or spontaneous social gathering. A large box window overlooks the rear gardens. At the heart of the home is the beautifully updated kitchen, thoughtfully designed with multiple work areas, custom inset cabinetry, a large center island and two sink areas. High-end appliances include a Wolf six- burner range, Electrolux double oven, two Miele dishwashers and two refrigerators. A furniture-style cabinet with its own sink provides an ideal coffee station or serving bar for entertaining. Adjacent to the kitchen, the light-filled breakfast room offers wonderful views of the perennial gardens and ever-changing landscape beyond. Bring your first cup of coffee into this inviting room or step into the spacious screened porch to enjoy views across the open fields and your own private woodlands. The gracious living room features a floor-to-ceiling brick fireplace. A separate study with an additional fireplace provides another wonderful space for quiet retreat or entertaining. Together, these rooms bring the home’s total to three fireplaces. The FIRST- FLOOR primary bedroom suite creates a comfortable private retreat. It includes a specially designed dressing/makeup area, an updated en-suite bath and ample closet space. Direct access to the surrounding deck extends the living space outdoors. A recently updated powder room and generous laundry room with sink and cabinetry complete this portion of the main level. Convenient access to the side-entry four (4) car garage adds to the home's functionality. Upstairs are three additional bedrooms, abundant closet space, a separate makeup station with sink and a full bath with both walk-in shower and tub/shower. Also on this level is an expansive walk-in, floored unfinished attic with a cedar closet. It offers valuable, easily accessible storage today, along with possibilities for a future owner's needs and vision. The lower level is partially finished with game room, wet bar, half bath and generous storage space. Numerous improvements enhance the property. These include a newer roof, driveway, front walkway, kitchen/breakfast room, hardwood flooring, primary bath, powder room, carpeting, water softener and four garage doors. The acreage is a defining feature of this exceptional property. Open land, perennial gardens and mature woodlands create a peaceful setting. The homesite is enrolled in Pennsylvania's Act 319 Forestry program, providing preferential tax assessment while helping preserve the land’s natural character. With its distinctive architecture, thoughtful craftsmanship, flexible floor plan, extensive updates and expansive acreage, this is a property of uncommon presence and individuality. The landscape transforms beautifully each season from flowering gardens and open fields to mature woods and beyond. At the same time, the home remains close to all that the Newtown/Yardley area has to offer. Make this YOUR HOME.

1703 Scott Dr, Newtown

$449,999

5 Beds ⋅ 2 Baths ⋅ MDAA2156446 MLS ⋅ ACTIVE Status

Beautifully updated, thoughtfully customized, and exceptionally well maintained, this 5-bedroom, 2-full-bath home offers far more space, character, and functionality than you might expect. From the moment you step inside, the home has a warm, modern farmhouse feel, with great natural light, comfortable living spaces, and custom touches throughout. The kitchen is a standout, featuring distinctive concrete and epoxy countertops that give the space a handcrafted look you simply don't see every day. Updated bathrooms and numerous improvements throughout the home complement its character while keeping it fresh and move-in ready. With approximately 1,194 square feet above grade plus more than 700 square feet of finished living space on the lower level, there is room here to spread out. The lower level features an expansive living area, two additional bedrooms, a dedicated laundry area, and utility/storage space, creating tremendous flexibility for everyday living, guests, hobbies, a home office, or simply having room for everyone. Outside, the home continues to deliver. A large deck overlooks the spacious, fully fenced backyard, with enclosed storage beneath the deck plus additional dedicated storage. And parking? There's plenty of it approximately eight off-street spaces, with four in front and four additional spaces behind the fence. The brick-front exterior adds classic curb appeal, while the home's layout, abundant natural light, generous finished living space, outdoor areas, storage, and extensive parking make it as practical as it is inviting. This is a home that has been lovingly cared for, thoughtfully improved, and designed to be truly lived in. Now it's ready for its next owner to make it their own.

214 Cross Creek Dr, Glen Burnie

$495,000

5 Beds ⋅ 3 Baths ⋅ MDAA2153822 MLS ⋅ ACTIVE Status

7949 Elvaton Road checks all the boxes! This spacious five-bedroom, three-full-bath rancher offers an updated interior, an expansive finished lower level, and a large, fully fenced backyard—all in a convenient location close to major commuter routes and BWI Airport. Beautifully updated, the home combines modern finishes with plenty of flexible living space. Hardwood floors flow throughout the spacious living room, where abundant natural light creates a bright and inviting atmosphere, and continue into the dining area and stunning gourmet kitchen. Anchored by a large center island with granite countertops, stainless steel appliances, and ceiling-height cabinetry, the kitchen serves as the centerpiece of the home and provides a welcoming space for gatherings, entertaining, and everyday meals. The main-level primary bedroom offers a comfortable retreat complete with an ensuite bathroom featuring a double vanity and tiled shower. Two separate closets provide plenty of storage in the primary bedroom. Three additional bedrooms offer flexibility for family, guests, a home office, or other living needs, while a full hall bathroom conveniently serves the remainder of the main level. Larger than many homes in the neighborhood, the full lower level spans the entire footprint of the home and significantly expands the available living space. The spacious recreation area provides endless possibilities for a playroom, movie room, home gym, entertaining space, or a combination of uses. A wet bar makes the space even more functional, while a dedicated laundry area and generous storage provide everyday convenience. The fifth bedroom creates an additional private space ideal for guests, an office, or extended living arrangements, with another full bathroom nearby. Outside, the expansive, level backyard is fully fenced and ready for outdoor living and entertaining. A spacious deck provides plenty of room for grilling, dining, and relaxing, while the yard offers ample open space for recreation and includes play equipment, a storage shed for tools and outdoor equipment, and a dedicated garden area for growing vegetables, flowers, or creating your own backyard retreat. Additional features include an ADT security system and a convenient location near shopping, dining, recreation, BWI Airport, and major commuter routes. Served by the Old Mill school area, 7949 Elvaton Road offers the space, updates, and versatility to fit a variety of lifestyles. Come see everything this move-in-ready home has to offer!

7949 Elvaton Rd, Glen Burnie

$495,000

4 Beds ⋅ 3 Baths ⋅ MDGA2012624 MLS ⋅ ACTIVE UNDER CONTRACT Status

Space, efficiency, and even more room to grow! Set on 6+ beautifully landscaped and wooded acres, this impeccably maintained home features 4-beds, 3-baths, and approximately 4,400 total sq ft: roughly 2,200 sq ft finished upstairs and an additional 2,200 sq ft walk-out basement. Inside, skylights add warmth and character to the living room, with hardwood flooring extending through the living and dining areas. The kitchen features quartz countertops and opens to a newly enclosed patio - the perfect place to relax and take in the scenic views. Two bedrooms include private en-suite bathrooms, while the third full bath serves the remaining bedrooms and guests. The expansive walk-out basement is approximately half below grade and currently unfinished, offering great potential for additional living, recreation, hobby, or storage space, plus a bathroom rough-in. A geothermal heating and cooling system provides consistent comfort, energy efficiency, and lower operating costs. A pellet stove provides a valuable secondary heat source, and the generator is configured to power essential systems during an outage, including the pellet stove, water pump, refrigerator, microwave, and select lighting. Outside, thoughtful landscaping, established raised beds for flowers or vegetables, and a gently sloping yard create a peaceful setting with plenty of room to enjoy the outdoors. A separate tractor shed provides practical storage for lawn equipment, gardening tools, and recreational gear, while an attached two-car garage off the main level provides even more space. This low-maintenance dream home also includes durable HardiPlank siding, energy conscious 2x6 exterior-wall construction, and an attached two-car garage contribute to its comfort, efficiency, and low-maintenance appeal. With generous indoor and outdoor space, energy-efficient features, backup power capabilities, and great potential for future expansion, this exceptional property offers comfortable living today with plenty of possibilities for tomorrow.

137 Youngwood Ln, Grantsville

$585,000

4 Beds ⋅ 3 Baths ⋅ MDCA2029682 MLS ⋅ ACTIVE UNDER CONTRACT Status

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. Turn Key and Move right IN! 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! The county is working on getting public sewer in the neighborhood. It is still only in the planning phases. See Docs Section for all info we have on it and docs needed to make an offer. Septic just pumped May 2025.

8541 Saint Andrews Dr, Chesapeake Beach

$650,000

4 Beds ⋅ 4 Baths ⋅ MDCA2029500 MLS ⋅ COMING SOON Status

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

$450,000

5 Beds ⋅ 3 Baths ⋅ MDAA2150768 MLS ⋅ ACTIVE UNDER CONTRACT Status

Open House for August 29th, 2026 has been Cancelled! 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

$459,900

3 Beds ⋅ 2 Baths ⋅ MDCA2027878 MLS ⋅ ACTIVE Status

**LESS THAN 2 MILES TO THE CHESAPEAKE BAY!** 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! Live the Salt Life Year Round in Chesapeake Beach! Convenient to **D.C., Annapolis, Baltimore & Joint Base Andrews.** Great schools, great neighborhood, and your chance to enjoy affordable Chesapeake Beach living!

2811 Glasgow Way, Chesapeake Beach

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