Chesapeake Bay Waterfront Homes for Sale

Many of the waterfront homes on the Chesapeake Bay offer spectacular views and some of the best sunsets on the Eastern Shore. Whether you’re looking for a waterfront home in Stevensville, Queenstown, or another Eastern Shore town, you’ll find a variety of waterfront homes to choose from. Discover the latest waterfront homes for sale on the Chesapeake Bay right here!

Search Chesapeake Bay Waterfront Homes for Sale Maryland

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7402 Kent Point Rd Stevensville MD 21666

Price$5,650,000

Est. Mortgage: $/month

MLS Number 1001760382

  • Single Family
  • Address 7402 Kent Point Rd
  • Bathroom 11
  • Bedrooms 8
  • Square Feet 21200

Kent Islands most prestigious address. The epitome of estate living. Stunning views, majestic grounds, gracious and stylish home . Come home to PARADISE EAST - 22,000 sqft of superb living space on 30 gorgeous acres of Chesapeake Bay waterfront. Recently re-mastered with updates to the main level Master Suite, Atrium, Chef's Kitchen, Gathering Room, Main Great Room, Pool and Smart-Home technologies. You will fall in love with the Theatre with Balcony seating, Club Room, Billiards Room, Observatory with Widow's Walk, Fitness Room, Elevator, Safe Room, Huge Carriage House with Showroom and 3-bedroom Guest Quarters, Pool House with Full Kitchen and Bath, Pool, Fire Pit, Pier with Lifts. Your own private oasis, yet within easy reach of WASHINGTON DC, BALTIMORE, PHILADELPHIA, NEW YORK CITY, all major commuter lines and 3 major east coast airports - DULLES, BWI, REAGAN NATIONAL.

Listed by Keller Williams Flagship of Maryland

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$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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24528 Beverly Rd Saint Michaels MD 21663

Price$4,900,000

Est. Mortgage: $/month

MLS Number MDTA134992

  • Single Family
  • LocationType Creek/Stream
  • Address 24528 Beverly Rd
  • Bathroom 6
  • Bedrooms 5

Wake up to the sights and sounds of tranquil San Domingo Creek on this historic waterfront estate. Relax with your morning coffee in the rose garden or on the extended dock enjoying the privacy Beverly Manor offers. Spend the day walking around St. Michaels exploring the Chesapeake Bay Maritime Museum and boutique shops that dot the main strip. Kick back at a brewery, distillery, or winery if you~re looking to lighten things up. Retreat back to Beverly for lunch on the back porch, watching the boats cruising by, or hop on your own boat from your deep water dock. Welcome visitors to their well-appointed guest house. As dinner is prepared in the gourmet chef~s kitchen, relax in the adjacent family room with family and friends. When it is time to sit, choose from the elegant dining room or the enclosed rear porch. As the evening winds down, take in the sunset sitting on the patio or around a fire pit while enjoying the breeze off the water. Retire back to the sitting room for a few laughs before heading to bed. Then rise and repeat...

Listed by TTR Sotheby's International Realty

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$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1965 Love Point Rd Stevensville MD 21666

Price$4,285,000

Est. Mortgage: $/month

MLS Number 1002263584

  • Single Family
  • LocationType Bay
  • Address 1965 Love Point Rd
  • Bathroom 7
  • Bedrooms 4

You pull into your long driveway, noticing as if for the first time the beauty that is the Chesapeake Bay in the distance. Your eyes quickly avert to the grandeur of the luxury estate that is your home. You remember that your family is home, eagerly awaiting for your return. As you enter through your 11 foot steel doors, you take a deep breath and silently begin to take it all in, but quickly refocus. You find your favorite people relaxing in the private theatre room that is surely to be the envy of all that experience it.Soon after, more guests arrive, all in awe of the detail, the attention, the pure magnificence that is the space you are fortunate to call home. As you begin to tour your guests, each are astonished at all that your home is. All 18 of you settle in for dinner in your grand dining space, your private chef shares the particulars of the meal. After dinner, everyone heads to the rear patio and settles in around the fire pit with a glass of wine, some running through the expansive rear yard, waves crashing on the shoreline, in the distance the sun begins to set over the bay. The evening seems to be nearly perfect. Soon, those exhausted, find themselves back in the private theatre room, asleep to their favorite movie. Others full of love and peace, split up, some heading to the game room, others to the grand living room for conversation and laughs while the fire crackles in your carved stone fireplaces. As the evening comes to an end, you remember, you earned this, you deserve this, your life is what you dreamed it would become. Welcome Home.

Listed by Long & Foster Real Estate, Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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22598 Davis Creek Dr Rock Hall MD 21661

Price$4,250,000

Est. Mortgage: $/month

MLS Number MDKE100044

  • Single Family
  • LocationType Creek/Stream
  • Address 22598 Davis Creek Dr
  • Bathroom 4
  • Bedrooms 3

Enchanting Eastern Shore waterfront residence is nestled on 56-acres on Davis Creek in Rock Hall. Expert craftsmanship and style distinguish Winding Creek House, designed by Chestertown architect, Peter Newlin. A series of pavilions are linked to create an interior of inviting, flowing spaces. Each pavilion enjoys its own river views and landscape in perfect harmony with the tranquil and naturally beautiful eastern shore setting. A charming summer house (free-standing screen porch), 100~ dock (4-ft mlw) with boat ramp, floating dock and boathouse are lovely settings to enjoy outdoor activities. Outstanding features of the home include an elevator, exquisite wood trim detail, built-in cabinetry, radiant floor heat, soaring two story living room, copper roof, granite kitchen and relaxing sauna. The small waterfront town of Rock Hall located on the Chesapeake Bay offers shops and dining. Historic Chestertown, home to Washington College, is just 20-minutes away and boasts the Chester River Walk, brick sidewalks lined with18th century homes, galleries, live theater, boat tours, cafes and restaurants. It also has a vibrant arts community, outdoor educational programs and waterfront park. Chestertown is about 90-minutes from Washington and Philadelphia.

Listed by Coldwell Banker Chesapeake Real Estate Company

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$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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6520 Swan Creek Rd Rock Hall MD 21661

Price$4,100,000

Est. Mortgage: $/month

MLS Number 1009997570

  • Single Family
  • LocationType Bayfront
  • Address 6520 Swan Creek Rd
  • Bathroom 7
  • Bedrooms 7

OPEN HOUSE CANCELLED TODAY, MAY 5, 2019Located on the Chesapeake Bay, Rock Hall Stud is a 240 acre property featuring a 12,520 SF unique, waterfront main residence built in 1986, swimming pool, private beach, stud farm with facilities, and beautiful private and sub-dividable acreage. An outside observation deck that spans the entire length of the home's copper roof boasts panoramic views of Bay Bridge and Baltimore skyline.

Listed by TTR Sotheby's International Realty

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$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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26108 Bachelors Harbor Dr Oxford MD 21654

Price$3,495,000

Est. Mortgage: $/month

MLS Number 1001491018

  • Single Family
  • LocationType River
  • Bathroom 6
  • Bedrooms 4
  • Square Feet 5251

Practically an island located where Choptank and Tred Avon Rivers enter Chesapeake Bay. Big 180 degree water views with 660 ft. of riverfront and tidal sandy beach. Great terraces, rolling lawn, private dock, and above rip-rap sandy beach with firepit for entertaining and enjoying gorgeous year-round sunsets and summer sail races. Big sky and adjacent open land maximize space and privacy.

Listed by Meredith Fine Properties

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$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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3015 Bennett Point Rd Queenstown MD 21658

Price$2,950,000

Est. Mortgage: $/month

MLS Number 1009979502

  • Single Family
  • LocationType River
  • Bathroom 8
  • Bedrooms 5
  • Square Feet 6140

Exquisitely sited on the Wye River, a 16.3 mile tributary of the Chesapeake Bay, and overlooking the Wye Island Preserve, this home tells a story about a perfected luxury lifestyle. Sweeping water frontage, stone rip rap, a 200-foot private pier, deep water and multiple slips set the stage for serenity and activity all at once. Full scale entertaining begins with a welcoming paver-styled entry, stone garden walls capped with lantern lighting, and a private circular drive with a lovely paver-styled drop off. Inside the main house, a dramatic barrel vault unfolds into a two story entry foyer crowned with a cupula and clerestory windows. Water views will draw guests further into the extended foyer celebrated with atrium doors, windows, and transoms offering exposures to a waterside covered porch. Exotic cherry floors are a unifying element throughout the main level interior and continue on to a stunning winding stair, embellished with a truly exceptional artist-commissioned rod iron sculptural rail. The extended foyer is sided by a library, sitting room and wet bar with richly finished custom millwork, raised panel wainscoting, fireplace surround and built-ins. Thoughtful design incorporates a gracious open living room with spectacular water views as the main event, followed by a beamed ceiling and stone fireplace. Formal dining adjacent to the living room is presented with paired built-in cabinets, lighted glass shelves, and a tray ceiling with cove lighting. Elegance is consistently upheld by a nearby butler~s service pantry with custom cabinetry, wine cooler and wet bar. Panoramic river views take center stage enhancing the breakfast room and gourmet kitchen. Central to the full service gourmet kitchen, is a contrasting entertainer~s island customized with a built in microwave, breakfast bar and double ogee edge on the granite top. Custom cabinets surround professional appliances including a Wolf gas range and Sub Zero fridge and freezers clad in custom wood cabinetry panels. Inside the pocket door, an expansive pantry room is outfitted with custom built-in storage, drawers, window and coffee bar counter. Inspired main level living includes a luxurious master suite with stunning waterside views from the bedroom, sitting room, and dressing room. Enjoy a spa-like experience in the master bath suite offering separate vanities adorned with imported glass sink bowls, a towel warming drawer and a tank-less water heater with smart features that anticipate your needs. A separate walk-in shower and separate His and Her water closets complete the space.Gather well and gather often offering guests the finest accommodations. Two wings on the upper level provide all-inclusive suite bedrooms, each with a sitting room and walk-in closet in addition to a private attached bath. No detail or opportunity has been missed including generous garage parking for seven including an attached conditioned three-car garage, as well as a detached four-car garage with a dedicated powder room. Above the detached garage, a fully outfitted guest apartment provides luxury accommodations offering flexibility for every occasion. From start to finish, every detail of this distinctive home is customized with energy saving features, exceptional quality, and beauty to befit this majestic place on the water that accompanies it. A once in a lifetime opportunity awaits here at 3015 Prospect Point Road.

Listed by Northrop Realty, A Long & Foster Company

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$
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$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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23946 Mount Misery Rd Saint Michaels MD 21663

MLS Number MDTA134740

  • Single Family
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 4052
  • Year Built 1805

Classic Eastern Shore residence offering charm and comfort, in a private 4 acre country setting only two miles from St. Michaels (17th Century port town, with shops and restaurants, and home of the Chesapeake Bay Maritime Museum). "Mount Misery" is an historic brick residence built in 1805/1806 on land granted by Lord Baltimore in 1667. Original doors, floors, mantels in early section. 5 fireplaces. Cedar shingle roof. Residence restored in 1954 by Pittsburgh industrialist Ralph Tennant using plans drawn by H. Chandlee Forman, Ph. D, A.I.A. Residence expanded and greatly ungraded by current owner in 2004, plans by Paul Richard, A.I.A., with large modern bathrooms and closets. Landscape design by Barbara Paca, Ph. D., O.B.E. of Preservation Green, with flowering shrubs, patios, garden "rooms". Trails to explore, small woodland park, stream. Pool, sauna, tennis court. 135 ft pier with 5 ft MLW, water and electric, and two power boat hoists. Plenty of crabs, fish and oysters! 700 ft of stable shoreline on Rolle's Creek/San Domingo Creek, with easy access to the Chesapeake Bay. Beautiful water views with sunsets over the water. Easton, Baltimore and Wilmington each about 1 hr 45 min. Easton Airport, and Memorial Hospital .

Listed by Shoreline Realty

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$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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3210 Bennett Point Rd Queenstown MD 21658

Price$2,850,000

Est. Mortgage: $/month

MLS Number MDQA103620

  • Single Family
  • LocationType Bayfront
  • Bathroom 7
  • Bedrooms 4
  • Square Feet 6626

Stunning estate minutes to the Chesapeake Bay Bridge. Attention to detail found at every turn. Over 5 acres on Eastern Bay with beautiful sunsets and waterviews every where.Master suite with his and hers closets, fireplace and walk out to private patio. Three additional bedrooms with ensuite baths. 8 seat home theater with private bath and bar area. Gourmet kitchen with large island and butler pantries. Smart home system, geothermal HVAC system, and many more upgrades. Full basement with lots of storage. Three car attached garage AND a large detached garage with space for numerous cars, an RV or boats.Two deeded deep water slips on the Wye River on the community pier- just minutes from the house.This is what living on the Eastern Shore is all about.

Listed by Coldwell Banker Residential Brokerage-Annapolis

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$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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304 Cove Creek Rd Stevensville MD 21666

Price$2,495,000

Est. Mortgage: $/month

MLS Number 1001757620

  • Single Family
  • LocationType Bayfront
  • Address 304 Cove Creek Rd
  • Bathroom 6
  • Bedrooms 5

Spectacular Custom 5 Bedroom, 5.5 bath Waterfront home in exclusive Cove Creek Club on Kent Island. Situated 12 ft above flood plan on a protected 2.78 acre point of land with boat lift and 5 ft of MLW. Rip rapped shore line, 48x18 ft pool w/ sun shelf. Magnificent views across the Chesapeake Bay with western sunsets. 4 car finished garage w/ workshop and guest home above. Country Club Amenities!

Listed by TTR Sotheby's International Realty

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$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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28480 Granville Ln Trappe MD 21673

Price$2,449,000

Est. Mortgage: $/month

MLS Number MDTA126920

  • Single Family
  • LocationType River
  • Address 28480 Granville Ln
  • Bathroom 6
  • Bedrooms 5

Welcome to 28480 Granville, where timeless elegance meets quintessential Eastern Shore living. Located in a quiet enclave of waterfront estates, offering the perfect combination of privacy and the peace and mind of having neighbors. This magnificent home has all the features one would expect and desire, including 2 master suites including one on the main level with beautiful water views, a gourmet chef's kitchen, gorgeous hardwood flooring including 100 year old pine on the main level, a spectacular sunroom that's perfect for summer crab feasts, front and rear porches for relaxing in your rocking chair whether sunset or sundown, and even a separate guest/in law wing w/elevator. Throw in the in-ground swimming pool and detached pool house with full bath, and one can see why this is a considered an Eastern Shore classic. But what is living on the Shore without water access? How about your own dock with multiple slips on calm Latrappe Creek, with water depths of 4+ feet, providing quick and easy access to the Choptank River and onto the Chesapeake Bay? And with over 500 feet of private shoreline , your views go on, and on, and on. Come see this magnificent home today and make it yours...your Eastern Shore lifestyle awaits!

Listed by Coldwell Banker Residential Brokerage-Annapolis

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$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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27637 Parkway Rd Easton MD 21601

Price$1,995,000

Est. Mortgage: $/month

MLS Number MDTA135056

  • Single Family
  • Address 27637 Parkway Rd
  • Bathroom 5
  • Bedrooms 6
  • Square Feet 6607

A Rare Waterfront Offering in a class of its own. Experience the best of our Chesapeake Bay lifestyle at Huntington Point in Talbot County, Maryland. This extraordinary estate, ideally located between the Villages of Easton & St. Michaels, boasts roughly 460'' of water frontage on the Miles River**The property offers an unparalleled combination of Waterfront amenities only minutes from the finest restaurants, theaters, galleries, shopping & grocery stores on the shore**Property includes 3 separate living areas, would make an perfect family compound. Sited on over 7 well-elevated acres is a stunning one level 5000+/- sf open-concept main residence, originally built by a famous local home builder for his own family & recently remodeled by the current owners. Virtually every room has a killer view of the water; grandfathered in, the main residence and guest cottage are just steps away from the beautiful Miles River providing dynamic views of waterfowl of all kind including Osprey, Heron, and Bald Eagles. The main house includes 3+ bedrooms, an expansive Chef's kitchen with Viking range, high end SS appliances, 2 dishwashers, Leather Quartzite countertops, center island, skylight. The Living room & Dining Room have chestnut floors, share a lovely gas fireplace, soaring ceilings & views galore of the Miles River only steps away.**The Spa like Master retreat features a centered soaking tub & heated tile flooring, Toto bidet, spacious custom glass shower for two, huge bedroom with sitting area & cedar lined window seat, walk in closet, another cedar closet as well as off the charts views of the water outside. The various guest rooms have ensuite bathrooms, one which includes a steam feature. Trex decking out every door facing waterfront. Oversized 2 car garage. An attached private Guest Cottage, also located steps from the water, with its~ own parking area includes a full bath & kitchen with new appliances, Bedroom with cathedral ship lap ceiling, spacious family room with door leading out to the commercial sized dock . Down the driveway is an expansive high ceiling, drywalled Boat House which will store several boats or a car collection, cedar closet and an electric garage doors. Above is the 3rd residence, guest / rental Villa, 1600+/- SF, 2 bedroom apartment featuring 2 stories with soaring ceilings, great views of the water, 2 large bedrooms, newly renovated bathroom with , full Kitchen, expansive deck overlooking the horse pastures below while facing the Miles River. A barbecue patio area & ample parking for several cars & boats below. For the Equestrian in your life, lush fields for grazing with gorgeous oaks for shade. All 4 paddocks include oak 3 board Fencing. The front field provides one 24x12 run - in shed with metal roof & weathervane & one 12x12 stable with 4x12 adjoining storage. There is an extraordinary drive through RV / horse truck & trailer/ storage building with three electric garage doors, a heated & carpeted Tack room & an office with a dedicated entrance with parking. These two large accessory buildings provide endless possibilities for equestrian use, multiple boat/trailer storage, large workshop & studio space & could easily convert to stables.**The roughly 460 ft of water frontage is fully riprapped & includes a private commercial grade pier with deep water dockage & two operating lifts, one of which for up to 50,000 lbs. There is a cleaning kitchen station on the dock as well.**Come take a tour & find yourself enjoying the best the Eastern Shore has to offer!

Listed by Benson & Mangold, LLC

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$
%
$/month over payments
Federal 30-year interest rate: 4.07% last updated on May 16, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Copyright 2019 BRIGHT, All Rights Reserved.  Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Chuck Mangold participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.Data last updated May 19, 2019. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale.

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