Homes for Sale near Chesapeake High School

• 

  

  

  /23

  $229,999

  • 3 Beds
  • 2.5 Baths
  • 1,452 Sq Ft

  958 Middleborough Rd, Essex, MD 21221

  This delightful three-level end-unit townhome is brimming with character, starting with its inviting front porch that boasts structurally reinforced integrity updated in 2026 for lasting peace of mind. As a coveted end unit, this home offers added privacy and a little extra outdoor space, all situated on a quiet, friendly street. The main level welcomes you with a spacious living room that

  Cory Flere Compass

  958 Middleborough Rd, Essex, MD 21221
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• 

  

  

  /65

  $746,520

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,195 Sq Ft

  2036 William Ave, Essex, MD 21221

  This brand-new Arlington Farmhouse by Greenspring Homes is officially finished and ready for an immediate move-in at Water’s Edge on Sue Creek. This home is crisp, modern, and waiting for its first owner. The layout features a high-end gourmet kitchen that flows into a firelit family room, plus a primary suite designed as a genuine retreat with a spa-style walk-in shower. Walk through the private

  Juna Korreta Monument Sotheby's International Realty

  2036 William Ave, Essex, MD 21221
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  /23

  $298,500

  • 3 Beds
  • 1.5 Baths
  • 1,080 Sq Ft

  403 Kosoak Rd, Middle River, MD 21220

  This stylishly updated three bedroom home is ready to impress from the moment you arrive. Fresh siding, new doors, and a new roof make this home standout. The beautifully landscaped front yard doesn't hurt either. Step inside to a welcoming entry featuring a striking accent wall, modern coordinating lighting, and updated entry steps that set the tone for the rest of the home. The kitchen offers

  James Boyd Real Estate Professionals, Inc.

  403 Kosoak Rd, Middle River, MD 21220
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  /61

  $550,000

  $35K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 2,157 Sq Ft

  21 Sidewell Ct, Essex, MD 21221

  *****BRING YOUR BOAT OR RV!****Tucked away on a quiet cul-de-sac along scenic Hopkins Creek, this beautifully updated home offers stunning water views and the perfect blend of comfort and versatility. Relax on the inviting front porch and take in peaceful creek views or unwind in the sunroom filled with natural light. The main home features 3 spacious bedrooms and 2 full baths upstairs, including

  Eileen Aubele Alberti Realty, LLC

  21 Sidewell Ct, Essex, MD 21221
• 

  

  

  /31

  $225,000

  • 4 Beds
  • 2 Baths
  • 2,088 Sq Ft

  1314 Cherry Garden Rd, Essex, MD 21221

  Welcome home to this tucked away residence in Essex. This is a great opportunity for primary residents who don't mind some repairs or for an investor who is seeking an investment opportunity. The exterior offers a large flat yard with over 1/2 an acre and lots of parking space. The property is located on a peaceful and quiet dead end road yet close to all amenities such as restaurants, beaches,

  Daniel Register Northrop Realty

  1314 Cherry Garden Rd, Essex, MD 21221
• 

  

  /14

  $285,000

  • 2 Beds
  • 1 Bath
  • 981 Sq Ft

  2023 Tred Avon Rd, Essex, MD 21221

  Unlock the potential of this 2-bedroom, 1-bath rancher situated on a spacious 0.72-acre lot in the water-oriented community of Middleborough. Offering some water views and endless possibilities, this property is ideal for, builders, or buyers seeking extra outdoor space and room to grow. While the home could benefit from some TLC, it features strong structural integrity.Property highlights

  April Chaney Iron Valley Real Estate Charm City

  2023 Tred Avon Rd, Essex, MD 21221
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  /34

  $389,900

  $9K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,320 Sq Ft

  1811 Cape May Rd, Essex, MD 21221

  Welcome home to this newly renovated 4-bedroom, 2.5-bath split-level located in the sought-after water oriented community on Cape May road. This move in ready property features a bright and modern kitchen with white cabinetry, granite countertops and stainless steel appliances, perfect for everyday living and entertaining. Step outside to the large backyard and expansive deck, ideal for outdoor

  sarah cruikshank Streett Hopkins Real Estate, LLC

  1811 Cape May Rd, Essex, MD 21221
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  /2

  $699,000

  Coming Soon

  • 4 Beds
  • 2.5 Baths
  • 2,229 Sq Ft

  2220 Silver Lane Rd, Essex, MD 21221

  Professional photos coming soon!Coastal Charm Meets Golf Cart Convenience!Welcome home to this stunning 4-bedroom, 2.5-bath Colonial, perfectly designed for modern living and an effortless resort lifestyle. Step inside to an expansive, sun-drenched open-concept main floor—the ultimate setup for entertaining friends or relaxing with family.The spacious primary suite is a true retreat,

  Michele Braun Keller Williams Flagship

  2220 Silver Lane Rd, Essex, MD 21221
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  /80

  $599,950

  $75K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,680 Sq Ft

  1452 Galena Rd, Essex, MD 21221

  Waterfront living at its finest. Welcome to 1452 Galena Road, a 3-bedroom, 2.5-bath home offering sweeping open water views, a private pier, and an exceptional outdoor entertaining setting. * Amazing 180 degree Water Views! Enjoy mornings on the expansive waterside deck, evenings in the gazebo overlooking the water, and direct access for boating, fishing, or simply unwinding along the shoreline.

  Skip Tolley EXP Realty, LLC

  1452 Galena Rd, Essex, MD 21221
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  /51

  $450,000

  $100K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 1,620 Sq Ft

  2224 Middleborough Rd, Essex, MD 21221

  Unfinished single-family home offering exceptional potential, with a possible layout of 5 bedrooms and 4.5 bathrooms. All construction permits are fully updated, and recent work completed in Fall 2025 provides a solid foundation to complete the project. Ideally located close to the water with partial water views, this property presents a rare opportunity to customize and add value in a desirable

  Catalina Sandoval RE/MAX Realty Centre, Inc.

  2224 Middleborough Rd, Essex, MD 21221
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  /41

  $719,900

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,684 Sq Ft

  2032 William Ave, Essex, MD 21221

  This brand-new Fairhaven Cape Cod by Greenspring Homes is officially finished and ready for a Spring move-in at Water’s Edge on Sue Creek. Designed for those who want to age in place without sacrificing style, this fresh build features a rare main-level primary suite and an additional first-floor bedroom/office. The open-concept interior flows from a gourmet kitchen with a large island into a

  Juna Korreta Monument Sotheby's International Realty

  2032 William Ave, Essex, MD 21221
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  /32

  $310,000

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft

  927 Homberg Ave, Essex, MD 21221

  Welcome home to this newly renovated 3-bedroom residence where modern upgrades and thoughtful improvements shine throughout. The updated kitchen features sleek stainless steel appliances, stunning granite countertops, and ample space for cooking and entertaining. The full bathroom has been tastefully remodeled with custom tile finishes and tile flooring, creating a fresh and stylish retreat.

  Monica Richardson Cummings & Co. Realtors

  927 Homberg Ave, Essex, MD 21221
• 

  

  /21

  $149,500

  • 2 Beds
  • 1 Bath
  • 739 Sq Ft

  2 Banyan Wood Ct Unit 304, Essex, MD 21221

  Welcome to 2 Banyan Wood Ct! This Penthouse condo breaths modernity into Essex MD. Step into your foyer to see clean LVP floors, quartz breakfast bar and recess lighting. As you stroll into the Kitchen, find your sleek quartz countertops, quality cabinets , finished backsplash and mostly stainless steel appliances. With a bedroom filled with natural light and walk in closet, mornings will seem

  Hunter DeCesare Berkshire Hathaway HomeServices PenFed Realty

  2 Banyan Wood Ct Unit 304, Essex, MD 21221
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  /11

  $149,900

  • 3 Beds
  • 1 Bath
  • 786 Sq Ft

  1260 Sugarwood Cir Unit 303, Essex, MD 21221

  Susan Shterengarts Long & Foster Real Estate, Inc.

  1260 Sugarwood Cir Unit 303, Essex, MD 21221
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  /17

  $219,900

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,302 Sq Ft

  1031 Foxwood Ln, Essex, MD 21221

  Reduced Price!! New price, better value at $219,900! Welcome to 1031 Foxwood Lane! This well-maintained 3-bedroom, 2 full-bath townhome offers comfortable living space and a convenient Essex location. The main level features a spacious living room, dining room, and plenty of natural light throughout. Upstairs, you'll find three generously sized bedrooms and a full bathroom.The fully finished

  Vida Kwateng-Pugh EXP Realty, LLC

  1031 Foxwood Ln, Essex, MD 21221
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  /3

  $160,000

  $25K PRICE DROP

  • Land
  • 29,185 Sq Ft
  • $238,806 per Acre

  830 Cedar Ave, Essex, MD 21221

  830 Cedar Avenue offers a .67 acre waterfront lot on Muddy Gut. This partially wooded lot is ready for the water and sewer hook up ( water and sewer already at the lot). Are you ready for the sun and the moon to create a constantly changing natural reflective canvas for your enjoyment? It is well documented that the soft flow of a river provides a tranquil soundtrack to daily life. Give yourself

  Sandra Hondroulis Long & Foster Real Estate, Inc.

  830 Cedar Ave, Essex, MD 21221
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  /50

  $515,000

  Open Sat 12PM - 2PM $15K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,450 Sq Ft

  1307 Nautical Cir, Essex, MD 21221

  Buyer finances fell through no fault of sellers. Pride of ownership shines throughout this beautifully updated home. Major improvements completed within the last 8 years including the Roof, AC, Furnace, Kitchen, Bathrooms, Flooring on the main, upstairs, and basement levels. Plus all major appliances including Refrigerator, Stove, Dishwasher, Microwave, Washer and Dryer. Simply unpack and enjoy

  Sohani Bhookmohan Samson Properties

  1307 Nautical Cir, Essex, MD 21221
• 

  

  /6

  $869,900

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,247 Sq Ft

  2027 William Ave, Essex, MD 21221

  WATERFRONT NEW CONSTRUCTION - "The Ellington” by Greenspring Homes at Water’s Edge on Sue Creek This adorable To-Be-Built home is waiting for you to make it your own - pick your favorite colors, finishes, and little details to create your dream space. The layout features 3 bedrooms, 2.5 baths and a bright, open floor plan perfect for relaxing or entertaining. The best part? Use your own private

  Claire Cianos Monument Sotheby's International Realty

  2027 William Ave, Essex, MD 21221
• 

  

  /56

  $590,000

  • 4 Beds
  • 1 Bath
  • 1,700 Sq Ft

  1315 Wildwood Beach Rd, Baltimore, MD 21221

  OPEN HOUSE EVERY DAY, call for times. Bright and spacious, recently updated, 2 story WATERFRONT home on the Back River in highly desirable Wildwood Beach waterfront community. 1700-1800 sf (tax records incorrect - it does not reflect the back addition) updated bungalow with new roof, SS appliances, quartz countertops kitchen and bathroom, new insulated siding, new 100' pier w/boat slip and jet

  Raimundas Valacka Keller Williams Gateway LLC

  1315 Wildwood Beach Rd, Baltimore, MD 21221
• 

  

  /20

  $524,950

  $75K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,056 Sq Ft

  215 Nanticoke Rd, Essex, MD 21221

  A unique opportunity to own a home that offers the kind of lifestyle people dream about—peaceful waterfront community living with a sense of calm that feels increasingly hard to find. Tucked away in an inviting setting, this home welcomes you with light-filled spaces, a comfortable flow, and an atmosphere that instantly feels like home. The living areas are designed for both everyday comfort and

  Skip Tolley EXP Realty, LLC

  215 Nanticoke Rd, Essex, MD 21221
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  /77

  $850,000

  • 4 Beds
  • 4 Baths
  • 2,619 Sq Ft

  2304 Poplar Rd, Essex, MD 21221

  Exceptional waterfront retreat on serene Sue Creek, boasting about 100 feet of pristine shoreline, a private dock with multiple boat slips and an electric boat lift. This rare offering provides effortless access to the water and an unparalleled setting for coastal living, entertaining, and recreation. The truly unique remarkable waterfront setting enjoys year-round panoramic views, from the first

  Xuri Wang Hometown Elite Realty LLC

  2304 Poplar Rd, Essex, MD 21221
• 

  

  /70

  $699,990

  $25K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,920 Sq Ft

  2222 Monocacy Rd, Essex, MD 21221

  Gorgeous 3 Bedroom 3 Full Bath Brick Front Rancher set on Double Lot, Features Kitchen with Center Island and Stainless Steel Appliances 3 years young, Floors 3 years, Family Room w/ Wood Burning Fireplace, French Doors Leading to Deck and Water, Carpet, Newer Bath w/Jacuzzi Tub, Skylight 1 year young, Full Attic w/pull down stairs, Side Porch, Trex Deck & Bulkhead 2 years young, Shed, Boat Lift,

  Darlene Tawney Samson Properties

  2222 Monocacy Rd, Essex, MD 21221

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