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!

Call Chuck Mangold at 410-924-8832 with any questions or to schedule a private tour.

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7402 Kent Point Rd Stevensville MD 21666

Price$5,650,000

Est. Mortgage: $/month

MLS Number 1001760382

  • Single Family
  • LocationType Bay
  • Address 7402 Kent Point Rd
  • Bathroom 11
  • Bedrooms 8

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. All of this could be yours at PARADISE EAST on Kent Island.

Listed by Keller Williams Flagship of Maryland

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$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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: 4.28% last updated on Mar 21, 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
  • 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: 4.28% last updated on Mar 21, 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 Bay
  • Address 6520 Swan Creek Rd
  • Bathroom 7
  • Bedrooms 7

Located 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: 4.28% last updated on Mar 21, 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$3,900,000

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: 4.28% last updated on Mar 21, 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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144 Decoursey Cove Ln Queenstown MD 21658

Price$3,330,000

Est. Mortgage: $/month

MLS Number MDQA116358

  • Single Family
  • LocationType River
  • Bathroom 6
  • Bedrooms 5
  • Square Feet 5428

This home has a long and very interesting beginning as the Director's abode for the Aspen Institute. The Director's family and the Callahan's have been the only two inhabitants. The house was commercially built by Mr. Houghton whose pick of Architect was very influenced by Frank Lloyd Wright and was positioned very close to the Wye River which is unheard of now. When looking at comps realize that this property is closer to the water then most and has a high elevation from MLW. This provides for views from within the home that are unequalled in terms of water views. In fact some views are only of water giving the illusion that the home is actually built on the water. Breath taking. The short boating distance to the Chesapeake Bay thru Eastern Bay plus the sail boat depth water around Wye Island makes any boating possible. The pier is equipped with a power boat lift, jet ski lift and deep water for a large boat. Moreover the property is protected by Wye Island as a barrier to and along storms moving up the Bay. The views of Wye Island are unobstructed with Sunrises and Sunsets dancing off the water. The purchase of a contiguous 9.34 acres of land increases the nature appeal as well as privacy. Moreover, the land is contoured to easily contain a 5,000 SF pond that would be inviting to nature and man. The Landscaping provides a patio on the water side as well as a patio with an enclosed court yard looking out on the nature side. The inviting front circle drive can be a setting for a theme of whatever interest the new owner wishes. This home is located 5 miles from rout 50. Chesapeake College and an New Emergency Medical Center plus BWI Airport and Easton Airport are all very close plus 30 minutes to Annapolis or Easton and less then an hour to Washington DC. High speed Fiber Optics are now available. Buyer must promise to Dance the Moonlite nights away on the open deck off the Master Bedroom and enjoy the Beautiful Sun Rises. Simple stated enjoy all nature has to offer. Worth the visit.

Listed by EXIT On The Bay

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$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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$3,200,000

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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$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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 Bay
  • 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: 4.28% last updated on Mar 21, 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 Bay
  • 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: 4.28% last updated on Mar 21, 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: 4.28% last updated on Mar 21, 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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307 Queens Ct Stevensville MD 21666

Price$1,950,000

Est. Mortgage: $/month

MLS Number 1002485370

  • Single Family
  • LocationType Bay
  • Address 307 Queens Ct
  • Bathroom 7
  • Bedrooms 6

This stunning waterfront estate in Kent Island encompasses 2 houses overlooking the Chesapeake Bay on over one acre of land. The property includes a serene in-ground pool, beautiful hardscape, lush landscape, private dock with boat lift and jet ski lift, separate garage, two kitchens, two laundries, built in sound and security systems, and renovated finishes throughout the approximately 5,000 sqft

Listed by TTR Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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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20361 Glanville Ln Rock Hall MD 21661

Price$1,925,000

Est. Mortgage: $/month

MLS Number 1002343612

  • Single Family
  • LocationType Bay
  • Address 20361 Glanville Ln
  • Bathroom 2
  • Bedrooms 2

Architectural Masterpiece located just feet away from Chesapeake Bay! Designed and built in 2005/2006 with panoramic views of the Chesapeake Bay 365 days a year. Built as a getaway/executive retreat this house sits on just over 1 acre and includes the adjoin-able build-able 1 acre lot beside it also located directly on the Chesapeake Bay waterfront! Basement could be used for gym, etc.

Listed by ARE PROS.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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 March 25, 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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