Homes for Sale near Chesapeake High School

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  $299,899

  • 3 Beds
  • 1.5 Baths
  • 1,742 Sq Ft

  947 Martin Rd, Essex, MD 21221

  Exceptional Properties. Exceptional Clients. Step inside this truly unique property that perfectly blends character, comfort, and flexibility. Featuring three bedrooms and one full bath, this home offers a spacious and adaptable layout ideal for everyday living.As you walk up the spacious deck and through the front door, you’re welcomed into a bright and inviting space that can easily serve

  Natasha Lasek Keller Williams Gateway LLC

  947 Martin Rd, Essex, MD 21221
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  /15

  $1,199,900 New Construction

  • 5 Beds
  • 4.5 Baths
  • 4,627 Sq Ft

  1158 E Riverside Ave, Essex, MD 21221

  CONSTRUCTION IS UNDERWAY ON THIS REMARKABLE CUSTOM WATERFRONT HOME ON BACK RIVER NESTLED ON OVERSIZED 1/2 ACRE DOUBLE LOT WITH DEEP WATER PIER & BOAT LIFT - this home will feature over 4600 sq ft of finished living space on 4 levels offering the buyer the opportunity to customize colors and finishes throughout as they work with the builder to completion. Standard features for this home include a

  Andrew Lehr LPT Realty, LLC

  1158 E Riverside Ave, Essex, MD 21221
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  /35

  $359,900

  • 3 Beds
  • 2.5 Baths
  • 1,690 Sq Ft

  2203 Middleborough Rd, Essex, MD 21221

  Welcome to 2203 Middleborough Rd in Essex, MD - a beautifully maintained home that perfectly blends comfort, style, and convenience! This spacious home has plenty of room for everyone to live and entertain comfortably! Featuring an open-concept living and dining area, modern kitchen with contemporary finishes, stainless steel appliances, 3 bedrooms plus a versatile bonus room (ideal for a home

  Debbie Spivey Hyatt & Company Real Estate, LLC

  2203 Middleborough Rd, Essex, MD 21221
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  $2,595,000

  • 5 Beds
  • 5.5 Baths
  • 7,700 Sq Ft

  605 Rockaway Beach Ave, Essex, MD 21221

  Experience extraordinary waterfront living in this custom coastal residence, perfectly positioned on high elevation overlooking Middle River with sweeping unobstructed views stretching to the Chesapeake Bay and Eastern Shore. Built in 2015 and designed for both elegant everyday living and grand-scale entertaining, this exceptional 5-bedroom home offers rare craftsmanship, timeless finishes, and

  Skip Tolley EXP Realty, LLC

  605 Rockaway Beach Ave, Essex, MD 21221
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  $746,520 Open Sun 12PM - 4PM

  • 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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  /22

  $131,900

  • 2 Beds
  • 1 Bath
  • 776 Sq Ft

  4 Banyan Wood Ct Unit 203, Essex, MD 21221

  Cute 2-bedroom, 2nd-floor condo offered at an exceptional value! Enjoy peaceful views from your private balcony overlooking the water, the perfect spot to relax with your morning coffee.This well-maintained unit has been tastefully updated throughout with neutral tones, updated cabinets, modern counters, and durable laminate flooring. Spacious bedrooms provide comfortable living, with the

  Michelle Cannon Coldwell Banker Realty

  4 Banyan Wood Ct Unit 203, Essex, MD 21221
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  /17

  $345,000

  • 4 Beds
  • 3 Baths
  • 2,120 Sq Ft

  19 Springtide Ct, Middle River, MD 21220

  All new flooring and painting. Carpet free. End unit with fenced yard.

  Ruohong Liu UnionPlus Realty, Inc.

  19 Springtide Ct, Middle River, MD 21220
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  $275,000

  • 3 Beds
  • 1.5 Baths
  • 1,444 Sq Ft

  4069 Rustico Rd, Middle River, MD 21220

  3-bedroom, 1 full and 1 half bath traditional interior townhome in Carroll Crest with over 1,300 square feet, a freshly refinished lower level, and a private wooded backdrop that adds rare outdoor appeal. Recent updates include the lower level refinished in January 2026 with new carpet and an updated half bath, creating flexible finished space for a second living area, office, gym, or hobby room.

  Lee Tessier EXP Realty, LLC

  4069 Rustico Rd, Middle River, MD 21220
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  $399,000

  • 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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  /22

  $349,999

  • 3 Beds
  • 2 Baths
  • 1,442 Sq Ft

  2210 Monocacy Rd, Essex, MD 21221

  .Nestled in the charming tree-lined neighborhood of Middleborough Landing, this sun-filled as-is, two-bedroom, two-bath split foyer home. The landscaped front lawn beckons you into a foyer with high ceiling.The adjacent dining room is perfect for hosting festive gatherings, and it seamlessly connects to an expansive covered porch offering glimpses of the river—a serene backdrop of nature. Step

  Gloria Rosas Samson Properties

  2210 Monocacy Rd, Essex, MD 21221
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  $649,950

  • 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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  $450,000

  • 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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  $719,900 Open Sun 12PM - 4PM

  • 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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  /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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  /18

  $339,900

  • 3 Beds
  • 1.5 Baths
  • 1,500 Sq Ft

  945 Homberg Ave, Essex, MD 21221

  Looking for space that fits your lifestyle? This 1,656 sq ft home offers room to live, work, and unwind. From spacious living areas to versatile bonus space, every square foot is designed with comfort and flexibility in mind. Perfect for entertaining, growing, or simply spreading out—this home checks all the boxes. Currently the home is configured as two spacious primary suites but can easily be

  Carrie Dowd Douglas Realty, LLC

  945 Homberg Ave, Essex, MD 21221
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  /3

  $185,000

  • Land
  • 29,185 Sq Ft
  • $276,119 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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  /31

  $269,980

  • 3 Beds
  • 2.5 Baths
  • 1,530 Sq Ft

  112 Villa Capri Cir, Essex, MD 21221

  Discover the breathtaking water views from every level (without flood insurance premiums), where each day begins and ends with the beauty of the water. Spanning three levels of living space, this townhome offers over 1,800 square feet 3 Bedrooms, 2.5 Baths, and three expansive decks, perfectly positioned to capture stunning sunrises and unforgettable sunsets. Freshly painted with new carpet and

  Jaime Gervasi Keller Williams Gateway LLC

  112 Villa Capri Cir, Essex, MD 21221
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  /7

  $149,000

  • 3 Beds
  • 1 Bath
  • 1,152 Sq Ft

  1003 Bayner Rd, Essex, MD 21221

  Welcome to 1003 BAYBER—an incredibly affordable opportunity to own. Great renovation opportunity on a quiet block . Interior unit rowhome in need of cosmetic renovation and is perfect for for resale or rehab for rental. Strong rental market in the area. This home offers multiple exit strategies for the right buyer. 3 generous sized bedrooms up along with a full bath, separate dining room, large

  Anna Kosoy Kosoy Realty

  1003 Bayner Rd, Essex, MD 21221
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  /31

  $305,000

  • 3 Beds
  • 1 Bath
  • 1,410 Sq Ft

  945 Kinwat Ave, Essex, MD 21221

  WELCOME HOME TO THIS BEAUTIFULLY MAINTAINED 3- BEDROOM 1 BATH CAPE COD IN ESSEX, SH0WCASING TRUE PRIDE OF OWNERSHIP, THE MAIN LEVEL FEATURES A SPACIOUS PRIMARY BEDROOM AND A FULLY REOVATED BATHROOM. HARDWOOD FLOORS RUN THROUGHOUT , ADDING WARMTH AND CHARM. MAJOR UPDATES INCLUDE A( 2026 NEW ROOF HVAC AND HOT WATER HEATER!) NEWER APPLIANCES , WASHER , DRYER AND NEW REFRIGERATOR. THE KITCHEN HAS 2

  Francis Johns Cummings & Co. Realtors

  945 Kinwat Ave, Essex, MD 21221
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  /39

  $414,900

  • 5 Beds
  • 3 Baths
  • 1,794 Sq Ft

  511 Riverside Dr, Essex, MD 21221

  Newly remodeled 5BR/3BA expanded colonial situated on a spacious corner lot in the water oriented community near Cox's Point Park! Pull into the newly paved driveway and step inside a home designed for both comfort and style. The interior is filled with natural light and features blond luxury flooring, new carpeting, a freshly painted soft neutral palette, an open main-level layout, and numerous

  Stephen Pipich LPT Realty, LLC

  511 Riverside Dr, Essex, MD 21221
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  $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
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  $465,000

  • 2 Beds
  • 1 Bath
  • 1,515 Sq Ft

  2200 Poplar Rd, Essex, MD 21221

  Tucked away in the lovely Cedar Beach community, this private waterfront, of impeccable maintenance, offers a blend of sunny lawns, water views, and mature trees for refreshing shade. Step inside this turnkey main level living home, and see it open up! With many spaces to entertain work and play, the home has 2 bedrooms, a spacious bathroom with soaking tub and separate shower, plus immense

  Lisa Carlisle EXP Realty, LLC

  2200 Poplar Rd, Essex, MD 21221
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  /39

  $415,000

  • 4 Beds
  • 2 Baths
  • 1,845 Sq Ft

  1510 Denton Rd, Essex, MD 21221

  .Waterfront living meets everyday comfort at 1510 Denton Road.Direct waterfront views off the porch with a 100 foot pier and 50 feet of water frontage. Currently set up as 2 apartments. Dividing wall can be removed to access upstairsExterior highlights include a private pier with boat lift, an oversized heated garage,This is a level lot with a fenced back yard and close to local

  ed zebeck Douglas Realty, LLC

  1510 Denton Rd, Essex, MD 21221
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  $850,000 Open Sun 1PM - 3PM

  • 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
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  $725,000 Coming Soon

  • 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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