Eastern Shore Waterfront Homes

CAPTIVATING CHESTER RIVER PRIVILEGED COLONIAL close to beaches, pier & playground! Sprawling rear yard inviting picnics, pets & play! Meticulously maintained brick/sidi...

Located in the small, private peninsula of fine properties in Serenity Farms, this absolutely gorgeous waterfront home is situated on just under 4 beautiful acres! A w...

Stunning classic Eastern Shore estate with approximately 4,000 ft of shoreline on the Miles River and Gulley’s Cove. “Little Ashby” is situated on nearly 40 acres of pri...

Extraordinary Eastern Shore waterfront home for sale. From its perch above the water, this thoughtfully designed home enjoys lovely broad views of the Chester River and v...

RINASCERE Glebe Creek Waterfront has it all! Spacious Brick home with 8 Bedrooms and 4.5 Baths on 3 levels. 12.7 Acres with gated entry, totally fenced in with mature t...

Located just ten minutes from historic Chestertown this is your chance to own an amazing property, with panoramic views, perched above the coveted "Fairlee Creek"! Enjoy...

**REDUCED!!** The price is now at the value of the LAND ALONE!! Remove the existing home of roll up your sleeves and bring this 3 bedroom, 2-1/2 bath home back to l...

Waterfront Lot on the Wye River. Highly coveted location with spectacular views, amazing elevation and mature trees. Previously part of the Wye Institute's Wye Woods prop...

Fabulous, mid-century modern house overlooking a tranquil river in Talbot County. Professionally decorated creating the perfect balance for the incredible architecture yo...

Your Oasis awaits at this spectacular Kent Island Estate. Friendship Manor singularly connects the past and present offering a myriad of possibilities on a grand scale fo...

Verified proof of funds or registration form required to show the property. 24+ hour notice required. Escape to another world with this striking New England-inspired wat...

New to the market for the first time in over 14 years! Prime Bailey's Neck property on the Oxford corridor and minutes to all that Easton has to offer. Beautiful 5+ acr...

Open Sunday 1-3PM WOW is what you will say from the moment you step inside and throughout this beautifully updated Queens Landing waterfront end unit townhome. Welcome to...

Three levels of magnificent water views! This 3br/2ba/2 half bath colonial has been meticulously maintained and shows pride of ownership! Nothing to do but move in and s...

A Private setting on a a Deep water Private Lake. Looking for a paradise with a private pond and a private lake make this your remote getaway.

Protected waterfront on Cox Creek. Blue Heron II to be built. Personalize this home to your taste. 3 story with waterfront decks, luxury finishes, and more. Join us to en...

Waterfront with endless views and a sandy beach. Blue Heron II model to be built. Chose your finishes to personalize your home. Kent Island Etsates is the 1st exit over t...

"Wakefield Farm", a unique almost 80-acre waterfront property centrally located just minutes to Easton & St. Michaels. The property itself is a rare opportunity for any ...

Available all weekend for showings !! Sept 24,25,26 OPEN ON SATURDAY 11-1:00 !! This property is a gift from nature, nestled on 3.7 acres of mature hardwoods at the h...

Irish Tides is brimming with classic Eastern Shore luxury. With gorgeous views of the Miles River from nearly every room on the property, this 4 bedroom 5.5 half bathroom...

A rare Bennett Point Waterfront is ready for its next owner! This idyllic location on Greenwood Creek offers unparalleled views, and exceptional navigable water with gre...

Wind Song is conveniently located between Easton and St. Michaels and enjoys some of the most spectacular water views in Talbot County with 7 Miles of Southwest exposure...

"Widehall" is the most acclaimed historic downtown waterfront estate in Chestertown MD, since 1769. The many stewards of this magnificent residence, including two Maryla...

Island Resort Style Living and Maintenance Free!!! Renovated Waterfront End Unit Townhouse...cozy living room with fireplace and french doors leading to back deck overlo...

Welcome to Gliding Gander located on the Chesapeake Bay! This spectacular waterfront property is simply one of a kind. Offering 117.57 acres with 100 acres of open land, ...

Spring Cove Manor! Currently this 7.99+/- acre waterfront property is operated as a country inn with daily and weekly rentals for the many visitors of Rock Hall. The mai...

Welcome to Gliding Gander located on the Chesapeake Bay! This spectacular waterfront property is simply one of a kind. Offering 117.57 acres with 100 acres of open land, ...

Over 1 acre, in-town waterfront property located next to popular Haven Harbour Resorts, this property would make a great B&B or nice family compound. There's lots of room...

Chesapeake Bay front beach home at historic Tolchester Beach, Maryland. Original owner for the past fifty-three years, BayCliffe is now available! Beautiful 200' private ...

DAVIS CREEK FARM- This property consists of a total of 217 acres in three separate lots which makes it perfect for a family compound or donated Conservation Easement oppo...

Unique opportunity to build on this Waterfront lot! This floor plan is the Puccini II, by Caruso homes designed for the current price point. You can pick your house plan...

A stunning representation of the eastern shore lifestyle situated on the Peachblossom Creek in the sought after Cookes Hope community. This 5 bedroom 4 full/1 half bathro...

Stripped out and complete renovation with the highest quality materials and craftsmanship available. Gleaming Brazilian Cherry floors in the main level, marble counter t...

Run! Don't miss the chance to scoop up this home on Cox Creek! Seller had appraisal done at end of June 2021 and it came in at $525k, provided upon request. First time...

Incredible opportunity to own one of the last buildable waterfront properties on exclusive Wye Island. 5 acres with over 450' of sandy shoreline with deep water anchorag...

This very well maintained home overlooking the Broad Chesapeake Bay is in a great condition with a semi-private location between Chestertown and Rock Hall, private but no...

Welcome to 28029 Holly Road! Waterfront rancher with easy access to Glebe Creek. Seller has enjoyed this home for nearly 25 years and now its time for the next owner to...

THE COVE - 385 feet of waterfront shoreline, wrapping around two sides of this property, located in a premier boating destination. Large rancher, one-floor living on Lo...

SPRAWLING KENT ISLAND CAPE COD WITH COX CREEK PIER on IDYLLIC 22 ACRES ! Pristine wooded acreage with pond . Deeded access to riprapped shoreline with pier/lift . 40...

Waterfront Lot with dilapidated residence. Existing well and septic.