Chesapeake Bay Property Listings

Waterfront property on the Chesapeake Bay and real estate in the surrounding area including Kent county, Rock Hall, Betterton, and Cecil County.

Chesapeake Bay

Rock Hall

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Located in the fun part of town, this is the perfect second home that is super easy to take care of. Very nice yard with space to enjoy a family gathering, and in walking distance to everything that makes Rock Hall one of Southern Living Magazine's Best Small Towns of the South. This charming cottage has been successfully used as a vacation rental. 

Price: $179,000

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Please call 410-639-2118 to speak with a representative about this property or fill out the form on the contact page.

Chesapeake Bay

Pearce Creek

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What a great combination of woods and open area for hay or crops and hunting. Great opportunity to either create a private oasis or continue with the subdivision that was started.  Need to call for deails. Access to the creek across Government Ground.

Price: $795,000

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Please call 410-275-2118 to speak with a representative about this property or fill out the form on the contact page.

Chesapeake Bay

Rock Hall

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Gracious and architecturally balanced home on an idyllic street along the Chesapeake Bay. The enclosed porch spanning the entire front of the house has an abundance of windows and a glimpse of the Bay across the street. The half acre yard is entirely fenced, and provides a park-like setting. There is also a detached two-car garage. Perfect for enjoying a water-oriented lifestyle in Rock Hall.

Price: $399,000

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Please call 410-639-2118 to speak with a representative about this property or fill out the form on the contact page.

Chesapeake Bay

Mouth of the Sassafras River

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A wonderful and well-maintained retreat for anyone looking to relax by the pool or enjoy the Upper Bay and sunsets from the screened porch. 150' of bulkhead and sandy beach offers more privacy to enjoy this spacious lot with beautiful mature trees. There are steps to access the Bay or go a short distance to the public beach located in the town of Betterton. Great area for outdoor activity and small town living.

Price: $545,000

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Please call 410-275-2118 to speak with a representative about this property or fill out the form on the contact page.

Chesapeake Bay/Still Pond Creek

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Idyllic setting on Still Pond Creek with a spectacular view of the water. 1.87 acres with 210 feet of waterfront and a 100 foot pier. Gorgeous water views from the wraparound deck on three sides of this striking chalet. 3 bedrooms, 3 full baths with a 392 sq. ft open area on the third level suitable for extra bedrooms or an office. Ceramic tile and parquet floors and ceiling fans in every room. Beautiful natural finished wood throughout the interior. Garage and workshop in the basement.

Price: $499,000

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Please call 410-639-2118 to speak with a representative about this property or fill out the form on the contact page.

Churn Creek

Kinnards Point

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Amazing panoramic water views surround this incredible property with almost 1000 feet of waterfront and is improved by a recently renovated home with water views from almost every room.  An ideally located screened porch, a guest house in like-new condition above the detached garage, mature trees and landscaping, hardscaping, a private dock and much more. One must see this property in person to appreciate all that it has to offer. 


Highlights of this property:

almost 1,000 feet of waterfront
separate guest home
private dock and deep water mooring
stone fireplace
cathedral ceiling
built-in bookcases
elevated deck and porch overlooking the water
prime location in Kinnairds Point
close to historic Chestertown

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Price: $1,100,000

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Please call 410-275-2118 to speak with a representative about this property or fill out the form on the contact page.

Still Pond Creek

Kinnairds Point

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First time offered. Handsomely crafted, custom built home in the treasured community of Kinnairds Point on Still Pond Creek. A spacious home with minimal maintenance which leaves time to enjoy the nicely landscaped two plus acres, beach and water activities of the community. So close to Chestertown where you find shopping, dining and entertainment. Don't miss the Saturday Farmers Market and the proximity of Washington College.

Price: $579,000

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Please call 410-275-2118 to speak with a representative about this property or fill out the form on the contact page.

Worton Creek/Tims Creek

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Privately located in a natural wonderland and close to Chestertown!  Relax and savor the water views from your deck, living room kitchen, bedroom, or from the separate cozy guest cottage filled with character and charm.  Deer, eagles, waterfowl can been seen from many places on this 7 acre property. The main residence and guest cottage have been recently updated and are very well maintained.  A private pier, canoe and kayak rack at water's edge and acres of mature woods just add to the value.


Highlights of this property:

separate guest home with vaulted ceilings and waterview deck
natural, wooded, private lot
deck overlooking the water
all new windows in both homes
private dock plus canoe and kayak rack

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Price: $725,000

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Please call 410-275-2118 to speak with a representative about this property or fill out the form on the contact page.

Chesapeake Bay

Kinnard's Point

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Last of the waterfront lots in Kinnaird Point, a  premier water oriented community with  access of 2 community areas, hosting beach access, small boat and kayak launch and boat ramp and picnic area at the other on Still Pond Creek. This 3 plus acre partially wooded lot  offers the choice of two different homesites and 200' plus of sandy beach frontage. Park your chair at the beach to watch the amazing sunset over the bay.

Price: $345,000

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Please call 410-275-2118 to speak with a representative about this property or fill out the form on the contact page.

Chesapeake Bay

Rock Hall

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Quality in-town home with bright gourmet kitchen and hardwood floors throughout. Close to the Bay. First floor bedroom with walk-in closet and attached bath could also be used as a den. Wonderful screened porch with a protected woodlands-view. Another pampering master suite on second floor plus two more bedrooms. Attached garage, ample for cars and toys. GREAT location.

Price: $265,000 (Under Contract)

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Please call 410-639-2118 to speak with a representative about this property or fill out the form on the contact page.

Fairlee Creek

Fairgale

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Located just outside of historic Chestertown, this three/four bedroom home provides a large kitchen overlooking the river, living room with fireplace, hardwood floors throughout, two decks, screened porch, lower level with an at-grade entrance, fully fenced yard, and includes a boat slip at the community dock on Fairlee Creek which provides easy access to the Chesapeake Bay.

Price: $535,000

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Please call 410-275-2118 to speak with a representative about this property or fill out the form on the contact page.

Chesapeake Bay

Rock Hall

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Beautiful coastal design for the discerning buyer. Hardwood floors, gourmet kitchen, delightful porches. Efficient Geothermal system. Gorgeous first-floor master bdrm, guest bdrm as well as a second floor family suite with wet-bar. Detached garage also has separate guest quarters with huge sauna, a wonderful artist's studio in attic. Terrific water views - Chesapeake Bay just across the street!

Price: $598,000

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Please call 410-639-2118 to speak with a representative about this property or fill out the form on the contact page.

Chesapeake Bay

Rock Hall

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Come check out the views and you will quickly see why home buyers LOVE Tilghman's Landing Condos in Rock Hall. Nicely updated kitchen,  open main level with hardwood floors. Decks facing the entrance o Swan Creek from The Chesapeake Bay. It's a Boat Parade all season long for you viewing pleasure! Condos include pool, spacious workshop and garage. Very well maintained and managed condo association.

Price: $349,000

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Please call 410-639-2118 to speak with a representative about this property or fill out the form on the contact page.

Chesapeake Bay

Swantown Creek

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5 acre lot with pond, rip-rapped shoreline, mostly open fields with some woods, & spectacular sunsets over the Bay. Located close to Rock Hall and it's many marinas and restaurants.

Price: $495,000

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Please call 410-275-2118 to speak with a representative about this property or fill out the form on the contact page.

Fairlee Creek

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This pristine contemporary is nestled on a partially wooded 3 plus acre lot with over 200’ of shoreline. Located in Fairgale, an upscale waterfront community just minutes from Chestertown, this property gives the feeling of a very special place. The home offers great space inside and out to entertain or to enjoy all the seasons of the year. Bristling with special features as beautiful wood throughout the house to exude warmth to a spacious deck to enjoy the wonderful setting. There is walk way to the water and a boat slip with lift at the community pier, which is only minutes to the Bay. Separate building to house all the toys for boating and other activity.

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Price: $898,000

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Please call 410-275-2118 to speak with a representative about this property or fill out the form on the contact page.

Elk River

Pond Creek

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Build your dream home on this 5 plus acre lot fronting on Pond Creek, tributuary off Chesapeake Bay. Access to dock and sandy beach at the community area. Deeded Boat Slip included.

Price: $348,000

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Please call 410-275-2118 to speak with a representative about this property or fill out the form on the contact page.

Mill Creek

Near Chestertown

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Beautiful 3 bedroom home nestled in a park like setting on Mill Creek.  This delightful property is in impeccable condition. Walkout lower level to a patio.  Decks above for wonderful views of the creek along with water access to Worton Creek.  Tiered walkway to a 55' pier with deck and dock.  Dredging project of this waterway is in the final stages of permitting and funding.

Price: $365,900

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Please call 410-275-2118 to speak with a representative about this property or fill out the form on the contact page.

Chesapeake Bay

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One of only two expanded 3 bedroom, 2 bath units in Rigbie Bluff offering a spacious living area, magnificent views of the upper Bay and piers, community pool, deep water boat slip with large lift and jet ski lift. This unit offers every amenity to enjoy waterfront living with the easy upkeep of a condominium. 

Price: $339,000

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Please call 410-275-2118 to speak with a representative about this property or fill out the form on the contact page.

Fairlee Creek

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A wooded and peaceful spot for relaxing, yet within walking, biking or boating distance to marinas, tennis, golf course, pool, restaurants and beach.  This 4 bedroom home has a great room full of windows facing the water, a fabulous deck, dock, plus a stone patio with built-in firepit.

Price: $ 597,000

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Please call 410-275-2118 to speak with a representative about this property or fill out the form on the contact page.

Chesapeake Bay

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Relax and take in an elevated panoramic view of the bay from the four-season wrap-around porch on this unique and rare offering on Beach Road. Fine finishings throughout define this modern beach house. The dock has two heavy-duty boat lifts on either side, and was built to withstand strong bay-front conditions. The property is protected with new bulk-heading.

Price: $ 899,999

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Please call 410-639-2118 to speak with a representative about this property or fill out the form on the contact page.

Chesapeake Bay

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Wonderful, private retreat with plenty of room inside and out for the whole family and situated on a beautiful Bayfront lot.  Unobstructed views of sunsets, rip rap shoreline with over 200' along the bay.

Price: $ 620,000

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Please call 410-275-2118 to speak with a representative about this property or fill out the form on the contact page.

Chesapeake Bay Boat Basin

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Wonderful opportunity to own a 30 slip marina located in the boat basin of Chesapeake City next to the Chesapeake Inn.  Plenty of transient business, both hourly and overnight.  1200 square foot shop, office, and bath house included.

Price: $ 1,200,000

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Please call 410-275-2118 to speak with a representative about this property or fill out the form on the contact page.

Sassafras River/Chesapeake Bay

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Huge sandy beach, panoramic sunset views, a 5 acre parcel surrounded by farm land, an elegant private entrance all combine to make this one of the finest homesites ever offered!

Price: $500,000

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Please call 410-275-2118 to speak with a representative about this property or fill out the form on the contact page.

Chesapeake Bay

Rock Hall

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Exceptional waterfront property with private beach and 264 ft. pier. There is 5ft. water depth at the end of the dock, which has 4 boat slips. Beautiful open floor plan was designed to maximize the incredible views of the Bay. There is a private guest suite on the first floor. Open floor plan, gorgeous library with built-in details, gourmet kitchen and stunning master suite.

Price: $945,000

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Please call 410-639-2118 to speak with a representative about this property or fill out the form on the contact page.