Chesapeake Bay Waterfront Homes for Sale

Waterfront Home in MarylandMany 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! You may also want to view all Eastern Shore waterfront homes for sale.

Search Chesapeake Bay Waterfront Homes for Sale Maryland

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7402 Kent Point Rd Stevensville MD 21666

Stevensville, MD7402 Kent Point Rd

Price$5,500,000

Est. Mortgage: $/month

MLS Number 1001760382

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

Kent Island's 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: 3.66% last updated on Nov 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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6558 Bozman Neavitt Rd Neavitt MD 21652

Neavitt, MD6558 Bozman Neavitt Rd

Price$5,250,000

Est. Mortgage: $/month

MLS Number MDTA132860

  • Single Family
  • LocationType River
  • Bathroom 6
  • Bedrooms 5
  • Square Feet 7462

"Clear Waters at Turkey Neck Point" is located just 10 miles (

Listed by Benson & Mangold, LLC

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$
%
$/month over payments
Federal 30-year interest rate: 3.66% last updated on Nov 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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6201 Swan Creek Rd Rock Hall MD 21661

Rock Hall, MD6201 Swan Creek Rd

Price$4,490,000

Est. Mortgage: $/month

MLS Number 1000487872

  • Single Family
  • LocationType Bayside
  • Address 6201 Swan Creek Rd
  • Bathroom 8
  • Bedrooms 8

Live your dream and enjoy an elegant and serene waterfront estate nestled on 177+ acres of a private and secluded peninsula along Maryland's Eastern Shore. Delight in the commanding and expansive views of the surrounding farmland and the picturesque Chesapeake Bay. The views are rivaled only by the impressive and completely renovated 5,500+ square foot classic 19th-century farmhouse. This majestic property features beautiful 100-year-old reclaimed heart pine flooring, an open floor plan with an abundance of natural light, four master suites, two additional guest bedrooms, a powder room, and a home office with custom bookshelves. Enjoy many options for casual or formal entertaining inside the house, outside on the sprawling lawn or around the relaxing pool and hot tub. You or your guests can also retreat to the one bedroom cottage situated along the shoreline. Its oversized windows provide captivating panoramic views of the bay. No matter what you feel like doing, there is something for everyone. You might take a refreshing dip in the pool, barbecue with guests on the large side deck, play a few rounds of tennis on the fenced-in hardtop court, enjoy the sunset from a rocking chair on the front porch or stargaze from the widow's walk. The estate is also the ultimate retreat for outdoor sportsmen & enthusiasts. Boaters will appreciate the private pier tucked in a protective cove on Tavern Creek. It is the perfect place to fish and crab for the evening's meal. You may also launch boats from the property's boat lift, floating dock or cement boat ramp. Grab your kayak from the boathouse and spend the day watching ospreys and blue herons while exploring the bay and the surrounding waterways. With its ideal location, you are just minutes away from some of the Chesapeake Bay's finest marinas and authentic waterside restaurants. Private and remote while being close to major Mid-Atlantic metropolitan areas, this Eastern Shore jewel is sure to give you and your family a lifetime of memories. The Main House: This 1870s farmhouse had a complete renovation from the foundation up along with a major addition in 1998. 5,500+ sq. ft. - 6 bedrooms/5.5 bath home. 3 full levels w/ partly finished basement. 3 woodburning fireplaces / 2 propane. Widow's walk / sundeck with 360 degree views. Large, covered front porch. Designed for both formal entertaining and causal living. Reclaimed heart pine flooring throughout. Original staircase and mouldings. The Cottage on the water's edge: 1 bed/1 bath with expansive waterviews. Situated along the Chesapeake Bay and protected Tavern Creek. Large, waterside deck. Waterside patio. Wood flooring throughout. Open floorplan designed for every room to have a view of the water. The Accessory Structures: Garage with 1 bed/1 bath above, attached fenced in dog pen. Converted dairy barn with two levels of storage. Storage shed for fuel & decoys. Dry boat house with a cement ramp for ease of launching small boats and running water. Pier with electric boatlift, floating dock, power and running water located on Tavern Creek with easy access to the Chesapeake Bay. Heated inground pool with built-in hot tub. Tennis court - fenced-in hardtop. The Grounds & Property Features: Ultimate privacy on 177+ acre waterfront peninsula. Gated entrance providing additional privacy. Two waterfowl ponds & 3 duck blinds. More than 1.5 miles of waterfront shoreline. All 4 contiguous lots are waterfront and each have separate tax ID's. Lot 2 / 36.74 acres - Lot 3 / 22.28 acres - Lot 4 / 78.18 acres - Lot 5 - / 40.63 acres- Agricultural conservation easements are available for review by request.

Listed by Coldwell Banker Residential Brokerage

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$
%
$/month over payments
Federal 30-year interest rate: 3.66% last updated on Nov 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

Rock Hall, MD22598 Davis Creek Dr

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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$
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$/month over payments
Federal 30-year interest rate: 3.66% last updated on Nov 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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24528 Beverly Rd Saint Michaels MD 21663

Saint Michaels, MD24528 Beverly Rd

Price$4,150,000

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 The ONE Street Company

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$
%
$/month over payments
Federal 30-year interest rate: 3.66% last updated on Nov 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

Stevensville, MD1965 Love Point Rd

Price$3,999,999

Est. Mortgage: $/month

MLS Number MDQA140618

  • Single Family
  • LocationType Bayfront
  • 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 waiting 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 sure 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 is 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: 3.66% last updated on Nov 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

Rock Hall, MD6520 Swan Creek Rd

Price$3,950,000

Est. Mortgage: $/month

MLS Number 1009997570

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

NEW PRICE! 200K PRICE ADJUSTMENT! Amazing opportunity. 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: 3.66% last updated on Nov 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

Oxford, MD26108 Bachelors Harbor Dr

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. PRICED BELOW ASSESSED VALUE!!

Listed by Meredith Fine Properties

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$
%
$/month over payments
Federal 30-year interest rate: 3.66% last updated on Nov 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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314 Friendship Manor Dr Stevensville MD 21666

MLS Number MDQA141708

  • Single Family
  • LocationType River
  • Bathroom 7
  • Bedrooms 6
  • Square Feet 8494

Amazing Kent Island Estate! The beautiful main house built in 1991 sits on 57+acres with 2,800 feet of water-frontage on Warehouse Creek. This 6 bedroom, 6.5 bath home is ready for you to make it your own. Enjoy the large attached 3 car garage as well as the beautiful 4 car carriage house. Oversized in ground pool. Perfect location for boating, fishing, and hunting. Only a few minutes to Chesapeake Bay by boat! The treasure of this property is the exquisite historic home built in 1700 and on the MD historical society list! Ideal for Wedding parties, Hunting groups, and vacationers who appreciate being in one of the oldest homes in Maryland. It is currently on Air BnB as a source for extra income. This charming historic house has 4 bedrooms and 3 bathrooms. Take advantage of the amazing potential this property offers for a Family, Wedding Venue, Retreat Center, or Equestrian estate. The opportunities are endless with this gorgeous estate abundant with wildlife, deer, and fowl and two private docks along with many acres of farm land. 3 Miles to the Chesapeake Bay Beach club and the Bay Bridge Airport. Potential uses can include hunting lodge, wedding venue and Bed and Breakfast

Listed by Keller Williams Realty Centre

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$
%
$/month over payments
Federal 30-year interest rate: 3.66% last updated on Nov 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

Queenstown, MD3210 Bennett Point Rd

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 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: 3.66% last updated on Nov 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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128 Twin Cove Rd Stevensville MD 21666

Stevensville, MD128 Twin Cove Rd

Price$2,495,000

Est. Mortgage: $/month

MLS Number MDQA140468

  • Single Family
  • Address 128 Twin Cove Rd
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 6890

The quintessential Eastern Shore Estate. Uncompromising in every way, this listing has it all. Sunset views of the Chesapeake Bay from a fabulous 6,900 +/- square foot main residence featuring a massive primary level master suite, open concept living areas, beautiful, new in-ground pool and outdoor gathering area, separate detached climate controlled office, all on a very private 14.5 +/- acre estate parcel with high elevation. If you have been looking for a correctly priced, generously sized retreat with some land and privacy, this is it.

Listed by Benson & Mangold, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.66% last updated on Nov 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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8744 S Bayview Dr Chestertown MD 21620

Chestertown, MD8744 S Bayview Dr

Price$2,399,000

Est. Mortgage: $/month

MLS Number MDKE115970

  • Single Family
  • LocationType Bayfront
  • Address 8744 S Bayview Dr
  • Bathroom 6
  • Bedrooms 5

An exceptional architect-designed 6,105 square foot home perched 100 feet-high on a bluff overlooking the Chesapeake Bay - the Chesapeake/Delaware shipping channel in full view. Included in the sale is the adjacent .66 acre parcel, "LOT PAR 1-2 ON A PL S/S MONTGOMERY AVE." You'll never tire of watching the ships and daily sunsets through the floor to ceiling windows. Floors throughout are finished in quarter-sawn red oak. Bluestone surrounds the house and continues into the entryway that provides a dramatic dining space with a 17-foot ceiling and a waterview as the backdrop. Sweeping open floor plan is graceful and elegant in its simplicity - full of light, angles, white walls and stunning views from every window. Plenty of gallery-like spaces to display your art. A chef-designed gourmet kitchen is a cook's dream, complete with a Thermador gas cooktop and electric double oven, two Subzero refrigerators, a Subzero freezer, under-counter Subzero refrigerator drawers, granite counters, and adjoining butler's pantry and many more custom features. A must see. First floor master suite has two luxurious master bathrooms finished in limestone and two custom designed walk-in closets with built-ins. Nationally known artisan-designed cherry stair rail leads to the guest floor with four bedrooms, three full baths and a huge bonus room, which could make a wonderful studio or game room. There are never-ending bay views from almost every room in the house. Heating and cooling is provided by a geothermal system. A three-car garage continues the house exterior design with matching trim and cedar shingles. Dock your boat at the premier marina just a three minute drive away. Nearby is Rock Hall with more marinas, shops, restaurants, and a world-class jazz venue called the Mainstay. Twelve miles away is historic Chestertown with Washington College and more shops and restaurants. Within two hours to Philadelphia, Baltimore and DC. By appointment only. This is one of the finest designed homes on the Eastern Shore. Be sure to allow plenty of time for your tour.

Listed by Gunther-McClary Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.66% last updated on Nov 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 November 22, 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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