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!

Search Chesapeake Bay Waterfront Homes for Sale Maryland

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7402 Kent Point Rd Stevensville MD 21666

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: 3.73% last updated on Sep 19, 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

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: 3.73% last updated on Sep 19, 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: 3.73% last updated on Sep 19, 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

Price$4,490,000

Est. Mortgage: $/month

Open House

MLS Number 1000487872

  • Single Family
  • Next Open House: Sat 28th 10:00 am - 3:00 pm
  • LocationType Bayside
  • Address 6201 Swan Creek Rd
  • Bathroom 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: 3.73% last updated on Sep 19, 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: 3.73% last updated on Sep 19, 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$3,900,000

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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$3,499,999

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: 3.73% last updated on Sep 19, 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. PRICED BELOW ASSESSED VALUE!!

Listed by Meredith Fine Properties

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$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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 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: 3.73% last updated on Sep 19, 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

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

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$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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: 3.73% last updated on Sep 19, 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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25883 Goose Neck Rd Royal Oak MD 21662

Price$2,249,000

Est. Mortgage: $/month

MLS Number MDTA136452

  • Single Family
  • LocationType Creek/Stream
  • Address 25883 Goose Neck Rd
  • Bathroom 5
  • Bedrooms 5

Welcome to Iron Gate - your tranquil oasis on Tar Creek in Royal Oak, MD. Enjoy spectacular sunsets under the shade of your beautiful mature trees and take in the refreshing prevailing breeze on Tar Creek. Full of history and architectural charm, this home longs to be a character in the next journey of your life. Located on 2.64 acres, this home features 5 bedrooms, 4 ~ baths, a grand dining room, chef~s kitchen, numerous multi-use rooms, 3 woodburning fireplaces, a waterfront gunite pool and patio, and a dock with boat lift and 4~ - 5~ mean low depth. Built in 1910, the home and pool~s footprint is only steps from the water offering a unique water~s edge living experience. Refreshing breezes can be enjoyed year-round from your waterfront patio and master bedroom balcony. Almost every room in the home has beautiful views of the water. The long lane offers you privacy as you are greeted with a beautifully landscaped ~secret garden~ welcoming you home. Enjoy outside spaces including your workshop and bike shed. Upon entry, you can immediately envision dinner parties in your dining room and cocktails in a formal sitting area. Sunlit from all angles, the next room can be used as an office or a solarium. Down just a few stairs, enjoy your library and informal sitting room. The chef~s kitchen and breakfast area are lit by sunshine. As you prepare luxurious meals in your gourmet kitchen, take in the stunning water views, sunrises, and sunsets. Stainless steel appliances, a 6-burner GE Monogram stove, double oven, subzero refrigerator, wet bar, granite countertops, and custom island offer a true chef~s experience. On the second level, there are three suites, each offering their own sitting rooms, bedrooms, bathrooms, and ample closet space. The master suite offers a large balcony with water views, and a master bath with a soaking tub, shower, double vanities, and water closet. On the third level, two more bedrooms, a full bathroom, and large closets add even more options for this spectacular home! Via water, you can easily boat to Oxford within 10 minutes, as well as Easton, St. Michaels, Cambridge, and other beautiful spots along the Chesapeake Bay. Also close to major metropolitan areas such as Washington DC, and with the local Easton airport, you will learn why the area is being hailed as the ~New Hamptons.~ Via boat or car, come experience the luxurious but laid-back feel of your new home!

Listed by Engel & Volkers Annapolis

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$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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 September 20, 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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