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Outrange at Blue Heron Farm

Enjoy the peace and tranquillity at “Outrange,” Blue Heron Farm’s recently updated cabin. This unique and rustic 2 bedroom, 1 bath home was designed by architect Randy Wagner and built in 1978. Tucked away on a 126 acre fourth-generation organic waterfront farm, Outrange is a private getaway situated just 15 minutes from historic Chestertown. With views of the Chester River and access to the farm’s private dock, Outrange is a magical getaway for anyone that loves the beauty of the Eastern Shore.

Waterfront Paradise w/ Pier - kayak to Chestertown

Escape to our private paradise where you can enjoy breathtaking sunsets from our pier, catch your own fish/crabs, sit around the fire pit by our 200+ foot private beach while gazing at countless stars, try our outdoor sauna w/panoramic view. It's a destination you can enjoy all year. Our home is located a short bike ride to Historic Chestertown, or you can take one of our kayaks in while you enjoy the Chester River. Bedroom 1: king bed+daybed w/trundle Bedroom 2: Queen Bedroom 3: Queen & bunkbed

Water Views in Rock Hall

Brand new, custom built home featuring a wall of windows with water views of The Haven on Swan Creek. 3 bedrooms, 3 full baths. Enjoy the screened in porch, sunning yourself on the deck or warming up by the wood stove in the wintertime. Fun tile work in the bathrooms, a giant soaker tub, built in bunk beds (full size), rugs imported from Morocco & lots of original art, brings this home to life! This house is playful & has lots of personality. Walk or bike to all the marinas & eateries in town!

Beautiful Kent Island Getaway with Pool

PRIME LOCATION! This home offers 4 bedrooms 3 1/2 baths with a spacious bonus room for all your family entertaining. You will love the open floor plan with cathedral ceilings with a beautiful stone fireplace. The Master bedroom with jacuzzi tub. Surround sound music system. Desk with computer. Separate pool house with kitchen and bathroom great for entertaining. Outside features includes a Concrete saltwater pool (not heated) with huge fenced in backyard and KOI pond. Porches back and front.

Cottage by the Bay in Rock Hall, MD

Sunny cottage in quiet waterside town of Rock Hall. Easy walk into downtown: grocery store, cafe, gift shop with beautiful housewares, gifts and jewelry, styling salon, quilt shop, ice cream shop, and local produce market. Gas fireplace, screened porch, stone patio, deck, several bicycles, tv for dvd's. Restaurants, crabs, Eastern Neck Wildlife Refuge, and nearby Tolchester and downtown Chestertown. Public pool, small beach (& picnic gazebos), bike around town...come to relax year round!

Chestertown Private cottage with NFL Sun Ticket

Escape to a secluded, romantic studio hideaway in the middle of Chestertown. Private parking, and over 1 acre of gardens to call your own. Relax in front of the fire with views of gardens in the windows. Kitchenette has extra large toaster oven, two burner hot plate, microwave, fridge, and Keurig/drip coffee makers. King bed with 100% cotton 1000 thread count linens and deluxe mattress, kitchenette, and washer dryer. We also host ‘Wren Retweet”, a house in front of the carriage house.

Magnolia House: walk to shops, restaurants, river

Historic details abound in this 1750s colonial gem surrounded by inviting gardens and located in the heart of historic Chestertown. 2 blocks from the scenic Chester River, and just steps away from High Street's (aka Chestertown's "Main Street") Saturday Farmer's Market, bakery, historic soda fountain, shopping, art galleries, dining, and downtown community events. As described by the New York Times: "This house is one of the contributing buildings in the town's historic district..."

Cabin on the Creek ~ Kayaks and Fire Pit

Unwind in our cabin tucked away on a private lane mins from Chestertown. We are situated on 6.5 wooded acres, perched up on 100’ bluff overlooking Churn Creek, a tributary off the Chesapeake Bay. Idyllic water views framed by a canopy of oak trees. Enjoy nature as you relax outside by the fire pit or stroll down to the ‘point’ to take in wildlife, or take a kayak out to explore the creek and water fowl. Deer come up through the woods and are often spotted on the property.

Chesapeake Bay Retreat W/Breathtaking Views

Escape to serenity on the shores of Chesapeake Bay! This luxurious, multimillion-dollar waterfront retreat offers sweeping water views, upscale furnishings, and timeless historic charm. Minutes from vibrant Rock Hall and Chestertown. Relax on the deck with morning coffee, stroll or bike the scenic waterfront paths, enjoy sun dips at Ferry Park beach, catch live performances at The Mainstay, or explore birdwatching trails at Eastern Neck Wildlife Refuge.

Relaxing Waterfront - Golf Course & Sunset Views

Our home away from home in Chestertown is truly an extraordinary property. Water and golf course views from every room. And wildlife! Some of the birds and animals we've seen: - blue herons - bald eagles - ospreys - ducks - turtles - otters Inside, there's room enough for 8, with 3 bedrooms and 3 full bathrooms, including one of each on the main level. Just one mile from downtown Chestertown, and a short walk to Chester River Yacht & Country Club

Down by the River

Relax while taking in the beautiful river views in this bright and welcoming home. Walk to town to enjoy all the delights of charming historic Chestertown. Kayak on the river, unwind on the dock, cook a gourmet meal in the huge open kitchen, relax by the fire-pit. This fully updated, light, and open home is a calming oasis and welcoming gathering place for family and friends. Fully accessible as well.

Waterfront house with private dock & kayaks!

Escape to tranquility at Mill Creek House, a contemporary waterfront sanctuary just 15 mins from Chestertown. Enjoy sunset views from the private dock, watch wildlife, and explore the creek with kayaks. Modern amenities like central AC, WiFi, and a gas grill ensure a comfortable stay. With 2 bedrooms and water views from nearly every room, it's the perfect retreat for relaxation and exploration.