Sherwood, MD Homes for Sale

Picturesque Waterfront Cottage minutes from St. Michaels! This craftsman is the perfect “Get-Away” nestled on Grace Creek with plenty of privacy and surrounded by nature. Home has been beautifully maintained and updated featuring all of the amenties you would expect including knotty pine flooring throughout, kitchen with center island, granite tops, huge 6-burner Viking Stove and oven, Subzero

Brian Gearhart Benson & Mangold, LLC

For the first time in over half a century, an extraordinary opportunity presents itself—a chance to claim a piece of history that has remained in the loving stewardship of one family for generations. Nestled on over 13 private acres, this breathtaking 6-bedroom, 4.5-bath waterfront estate offers an unparalleled living experience with 4,352 square feet of main living space plus an additional 1,500

Barbara McCaffrey Redfin Corp

PUBLIC SEWER COMING THIS YEAR! Immerse yourself in luxurious Eastern Shore living at this breathtaking waterfront retreat! Expertly designed by renowned local architect Pam Gardener, this four-bedroom, two-bath sanctuary rests at the end of a private road on a .92-acre lot, perfectly balancing tranquil seclusion with panoramic beauty. Showcasing 78 feet of riprap-protected shoreline along

Barbara McCaffrey Redfin Corp

Enjoy this picturesque waterfront cottage nestled in historic Neavitt, minutes from St. Michaels. Unique and private this property is overlooking Duck Cove and Balls Creek situated at the end of Duck Cove . This cottage is unique it has 8 boats slips with all new finger piers, 1 boat lift rated at 1500lbs, a davit for jet skis also rated at 1500lbs, bulkheading, water, and lighting . The dock

Jana Meredith Meredith Fine Properties

WATERFRONT CHARM! This home was built by Peninsula Construction with care in 2001 for the original and only owners! It boasts an open floor plan with hardwood floors throughout except the carpeted 3 bedrooms. The water views are captivating of Cummings Creek from the the open floor plan of the home but you will also enjoy the waterside screened porch with amazing views of the the quiet

Leslie Stevenson Shore Living Real Estate

This beautifully renovated waterfront rancher is nestled in the quaint village of Neavitt. Perfectly sited on Duck Cove with views extending to the Creek. A newly constructed front porch with a vaulted ceiling creates a welcoming focal point—an ideal space to unwind while taking in the serene water views. Inside, the open floor plan beams with natural light and features luxury vinyl plank

Kim Crouch Ozman Benson & Mangold, LLC

Welcome to 5520 Leeward Lane, a private waterfront estate tucked away at the end of a quiet, tree-lined drive on Tilghman Island—a rare opportunity to own a stunning piece of Maryland’s Eastern Shore. This expansive home features panoramic water views from almost every room and delivers the ultimate blend of luxury, comfort, and natural beauty. The grand foyer sets a graceful tone, leading into a

Samantha Jackson Keller Williams Realty

PARADISE FOUND! 3.5 Acres surrounded on 3 sides by water at the end of a private Cul-de-sac teeming with wildlife and immersed in the scenic beauty of mature trees and wetland grasses.  Enjoy morning coffee and watch the eagles, osprey and turtles nest in your backyard from your kitchen table!  The two-slip pier offers opportunities to fish and crab and serves as a gateway to time on the water

George Howard George Howard Real Estate Inc.

Welcome to this architecturally designed waterfront retreat, thoughtfully created to capture broad, breathtaking views and harmonize with its natural surroundings. Set in a quiet village near historic St. Michaels, this home offers a rare blend of tranquility, comfort, and convenience—just minutes from a public park and landing. Inside, the home features 3 spacious bedrooms, an office, and

Wink Cowee Benson & Mangold, LLC

History:"The Elms" is located on the Northeast corner of Mission Road and Route 33 in the village of Tilghman on Tilghman Island, Talbot County, MD. The house faces west, with the gable oriented on a north/south axis. Built around 1893. The Elms is clad in weatherboard and supported by a brick pier foundation. The roof of this two story frame home is covered in asphalt shingles. The five bay

Daphne Cawley TTR Sotheby's International Realty

The Ultimate Harris Creek Retreat—Unrivaled Views. Room to Spread Out. Sunsets You’ll Never Forget. FYI - Silt fence has been removed that appears in some photos)Welcome to your family’s forever getaway: a fully renovated waterfront estate on 2.4 acres with 240+ feet of direct water frontage. Perfectly positioned for stunning western views over Harris Creek, this exceptional property

Mark Meyerdirk Urban Brokers, LLC

CHARMING SHERWOOD VILLAGE WITH ITS RICH HISTORY. ONE OF THE BEST KEPT SECRETS.STEP BACK IN TIME, WONDER PAST BEAUTIFUL GARDENS UNDER SHADE TREES, GET GREETED BY THE PEACEFUL SETTING . THE COMMUNITY DOCK WITH MULTIPLE SLIPS AND FLOATING DOCK , THE KAYAK LANDING, IS A NEIGHBORHOOD HANG OUT, VERY POPULAR AT SUNSET TIME TO ENJOY GLORIOUS SUNSETS WITH WIDE OPEN VIEWS OVER HARRIS CREEK.THIS HOME HAS

Cornelia Heckenbach Long & Foster Real Estate, Inc.

Please don’t enter the home. The value is in the land.

Lesley Jackson EXIT Sunshine Realty

Located in the historic village of Neavitt, this charming house was built in 1890. It was thoroughly renovated in 2011 and the layout adapted for modern living, with light-filled rooms and a cleverly updated floor plan. The first-floor public spaces include a sitting room/office/entry, a generous living/dining room combination, and a handsome kitchen with water views, terrific storage, and room

Joan Wetmore TTR Sotheby's International Realty

NEW PRICE! Located minutes from downtown St. Michaels, “Aqua Vitae” the waters of life, sits on 8.6 private acres on Harris Creek, a Chesapeake Bay tributary. This custom-built offering w/ over 400’ of direct water frontage is comprised of 3 magnificent structures: a grand main residence, guest cottage, & “party barn” all highlighted by a waterside pool, pier w/ 4’ MLW, pine grove, putting green,

Doc Keane Washington Fine Properties, LLC

Welcome to Tilghman Landing on the Chesapeake Bay! This unique waterfront property offers an incredible opportunity, featuring three separate homes, two of which include garages, as well as a charming crab shack and private dock, all situated on .625 acres of Chesapeake Bay shoreline.Home #1: 6020 Sunset LaneThis spacious residence offers breathtaking, unobstructed views of the Bay. It includes 3

Melissa Tippett TTR Sotheby's International Realty

Enjoy peaceful water views and classic Eastern Shore charm in this well-maintained home in the village of Neavitt, just minutes from St. Michaels. Step into the open-concept great room, where hardwood floors, soaring ceilings, and a pellet stove create a warm and inviting living space. Floor-to-ceiling windows capture stunning views of Duck Cove and lead directly to a large deck—ideal for

Wink Cowee Benson & Mangold, LLC

Welcome to this beautiful, spacious 5-bedroom, 3 1/2-bathroom single-family home located in the sought-after Tilghman on Chesapeake community. This property offers the perfect blend of modern comfort and serene island living, featuring an open-concept floor plan with plenty of natural light and elegant finishes. Each bedroom offers ample space and comfort with the Primary Suite offering 2

Becky Wibberley Coldwell Banker Realty

It doesn't get any better than this ! Stunning brand-new ,one-story coastal residence with a contemporary flair! As soon as you enter this magnificent home, you will be captivated by 20'+ ceilings, superb craftsmanship , an extremely well-designed open floor-plan; breathtaking water-views on Dun Cove and a luxurious yet inviting kitchen. There are a total of 3 en-suite bedrooms as well as an

Robert Lacaze TTR Sotheby's International Realty

If you like old houses, you will love this one! Built by the Neavitt family c. 1870, it has been fully renovated but retains its original charm. The light-filled first floor boasts a charming living room with built-ins, spacious dining room, small sunny bedroom/office, full bath, and cathedral-ceilinged kitchen opening to a patio. A spacious bedroom with a glimpse of Balls Creek is on the second

Joan Wetmore TTR Sotheby's International Realty

The Nottingham, (elevation Z) is a modern ranch-style home with 3 bedrooms, 2.5 baths, and a 2-car garage with entry through a mudroom that leads to an expansive Great Room area that opens to the Kitchen. The Kitchen is ready for entertaining and cooking comforting meals for family and friends. An open dinette and large kitchen island offer a plethora of space for informal dining. You can take

Stacie Luhrman Benson & Mangold, LLC

Great opportunity to buy below market value. House needs work, but opportunity is endless. Sold strictly AS IS. Seller and listing agent do not guarantee accuracy in this listing. Buyer must do their own due diligence before submitting an offer. Cash or Hard Money only. Seller prefers New World Title Company.

Alex Fox Allfirst Realty, Inc.

Rustic Charm on Balls Creek - Wake up to sunrise views over Balls Creek from this charming 2-bedroom waterfront cottage. With nearly 200 feet of water frontage and a private pier, this serene retreat is perfect for weekend escapes filled with fishing, kayaking, or simply unwinding by the water’s edge. The cozy, nostalgic layout features a living room with wood floors, a dining area, and an

Kathy Christensen TTR Sotheby's International Realty

PRICED TO SELL!!Step into waterfront luxury with the spectacularly reimagined 4 bedroom, 3 bath custom home on Harris Creek meticulously remodeled by RBCI, Inc., an award-winning custom home builder. No expense was spared in creating this 2,731 sq. ft. masterpiece on over 1.5 acres of magnificent waterfront living. New flooring, counter tops, appliances, garage floor, extended

Ann Holtz Coldwell Banker Realty

.2 +/- acres located off of Cabin Ln in Sherwood, Md. Located 10 minutes from St. Michaels, MD and 5 minutes from Tilghman, MD.BUYER RESPONSIBILITY TO PERFORM DUE DILIGENCE REGARDING PROPERTY LOCATION, USE, RESTRICTIONS, AND TAXES.

Shawn Moore Meredith Fine Properties

.8 +/- acres located off of Punch Point Rd. Approximately 2.5 miles from Tilghman, Md.BUYER RESPONSIBILITY TO PERFORM DUE DILIGENCE REGARDING PROPERTY LOCATION, USE, RESTRICTIONS, AND TAXES.

Shawn Moore Meredith Fine Properties

Welcome to this beautifully updated 3-bedroom, 1.5-bath home, offering both charm and versatility. The home features three spacious bedrooms, including one with an attached area that can serve as a walk-in closet, nursery, or home office—perfect for adapting to your needs. With 1.5 bathrooms, you'll enjoy the convenience of a full bath and an additional half bath, ideal for family living or

Katie Mister Keller Williams Select Realtors of Cambridge

Discover peaceful country living at 8898 New Rd. This thoughtfully refreshed 3‑bed, 2‑bath ranch boasts a modern kitchen, an open floor plan, and natural light throughout. The primary suite offers comfort and privacy, while two extra bedrooms are perfect for family, guests, or a home office. Situated on a nearly half‑acre lot, the private backyard offers a relaxing escape or entertaining space.

BJ Kilby EXIT On The Bay

8.037 Acres located just west of St. Michaels, MD. All wooded and has been used primarily for hunting and fire wood. There is one and possibly two approved perc sites though they may need to be updated. Access off of New Road and Walkers Turn road, there may be an opportunity to subdivide but would need to be discussed with County Planning and Zoning. Opportunity to build your home with a lot of

James Bent Benson & Mangold, LLC

THIS HOME IS UNDER CONSTRUCTION!Welcome to Sussex, the epitome of modern rancher living! This single-level floor plan has captured the hearts of many, and it's not hard to see why. With stunning curb appeal and thoughtfully designed features and finishes, the Sussex offers versatility to suit any modern lifestyle. Step into an open-concept floor plan that seamlessly connects the Kitchen,

Mary Ann Hammel Mary Ann Hammel

ONLINE AUCTION: Bidding begins 7/16/2025 @ 10:00 AM. Bidding ends 7/18/2025 @ 11:50 AM. List Price is Suggested Opening Bid. Lot of Land located in Wittman, Maryland within Talbot County. Property is in close proximity to the many attractions in St. Michaels, Maryland. Easy Access to Major Traffic Artery Tilghman Island Road. Deposit: $7,500.

Adam Shpritz Ashland Auction Group LLC

Price adjustment! Opportunity abounds in this lovely 2 Bedroom 1 Bath detached home located in the picturesque waterfront town of Neavitt. This home boasts central air, attic space, a large yard, a shed and much more. Close to St. Michales and Tilghman Island this is a boaters and bird lovers paradise with a public boat ramp about a 1/2 mile away plus stores, shops , dining and

Richard Perrera Century 21 Downtown

.8 +/- private acres located in Sherwood, MD. Located 10 minutes from St. Michaels, MD and 5 minutes from Tilghman, MD.BUYER RESPONSIBILITY TO PERFORM DUE DILIGENCE REGARDING PROPERTY LOCATION, USE, RESTRICTIONS, AND TAXES.

Shawn Moore Meredith Fine Properties

.2 +/- private acres located in Sherwood, MD. Located 10 minutes from St. Michaels, MD and 5 minutes from Tilghman, MD.BUYER RESPONSIBILITY TO PERFORM DUE DILIGENCE REGARDING PROPERTY LOCATION, USE, RESTRICTIONS, AND TAXES.

Shawn Moore Meredith Fine Properties