Sherwood, MD Homes for Sale with Acreage

Welcome to this extraordinary waterfront estate, gracefully sited on 6.92 lush, landscaped acres with sweeping views of Leadenham Creek. Designed by architect Alan Meyers, constructed by Ilex Construction, and masterfully styled by interior designer Skip Sroka, this 10,000+/-sq. ft. residence is a showcase of timeless craftsmanship and elevated design. The custom brick exterior is crowned by a

Laura Carney TTR Sotheby's International Realty

Set along the peaceful waters of Caulk Cove, this extraordinary waterfront estate offers luxury, privacy and natural beauty across more than 10 acres. The property features open farm fields and professionally landscaped, park-like grounds, with a tree-lined driveway creating a breathtaking approach to the residence. Built in 2013, the custom-designed home encompasses nearly 8,500 square feet of

Kim Crouch Ozman Benson & Mangold, LLC

Located within 2 miles of historic St. Michaels this exceptional waterfront estate blends timeless elegance with a resort-style setting. This 4,200± sq. ft. custom, single-level all brick residence showcases soaring ceilings, an abundance of natural light, and panoramic views of Broad Creek from almost every room. A huge great room featuring a large brick fireplace and open living / dining

Barbara Watkins Benson & Mangold, LLC

"Fox Haven" Privately sited on almost 10 acres with 900+ feet of protected waterfront, this impressive retreat captures breathtaking wide water views from nearly every vantage point. Offering approximately 4,800 square feet of living space across three finished levels, the home is designed for comfort and versatility, with wood flooring, a well-appointed kitchen with island, and distinct living

Wink Cowee Benson & Mangold, LLC

A magnificent, stately, Daffin-built, Chesapeake Bay Brick Estate exudes excellent design and craftsmanship in this 5 bedroom (suites) , 5.5 bath 6,500 sq. ft brick home that majestically sits on 21.7 acres facing the Chesapeake Bay. Excellent construction quality and design are evident throughout this magnificent estate. Geothermal system on 1st and 2nd floors; Heat Pump for the 3rd floor;

Robert Lacaze TTR Sotheby's International Realty

"Bolton Farm", available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 115-acre waterfront estate with two deeded lots has breathtaking western views across the Chesapeake Bay. A gated

Laura Carney 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

Barely lived in totally maintenance free rancher on a 3+/- acre lot with broad water views. Freshly painted with new landscaping it is vacant and available for immediate occupancy! Main area has beautiful wood laminate flooring with carpet in all bedrooms. Bonus room to be used as an office/family room, granite counters with wine refrigerator and all nearly new appliances with utility room and

Bill Wieland Benson & Mangold, LLC

Offered for the first time in over 50 years, this 13+/- acre waterfront property on Broad Creek presents arare opportunity to own an expansive estate with exceptional shoreline frontage. With more than960+/- feet of waterfront, the setting provides unobstructed water views and a private pier, offeringdirect access to the creek and surrounding natural landscape. A tree-lined private

Chuck Mangold Benson & Mangold, LLC

Nestled along the peaceful waters of Swan Cove with access to Harris Creek, this circa 1890 farmhouse is full of Eastern Shore character and charm. Set on 1.38 private acres, the property offers the peace and serenity you’re seeking. The spacious enclosed front porch is accented with wood floors and a wood ceiling setting the tone of this charming home. The inviting foyer features original

Kim Crouch Ozman Benson & Mangold, LLC

Harris Creek Waterfront. This 3 bedroom, 2 bath well maintained brick one story house is the perfect getaway. Nestled on 1.63+/- acres it is the perfect blend of privacy and community. This home features a large kitchen with several entertaining areas including a cozy living room complete with a fireplace and a large living room that overlooks the huge screen porch and Harris Creek and a gracious

Jim Corson Benson & Mangold, LLC

Nestled on over 2 acres in the desirable water access community of Deep Harbor Farm, this beautiful Cape Cod beams with natural light. The home features over 2,400 sqft with 4 bedrooms and 2.5 baths. The welcoming foyer overlooks a spacious dining room and leads to an open kitchen complete with white cabinetry, stainless steel appliances, breakfast bar and a large table space. Just off the

Kim Crouch Ozman Benson & Mangold, LLC

Set on 19.5 private acres just minutes from historic waterfront Saint Michaels, this exceptional 4,492 sq ft residence offers the perfect blend of space, privacy, and convenience. The home features four bedrooms and two and a half baths, with expansive living areas ideal for both everyday living and entertaining, including a well-appointed chef's kitchen. The thoughtfully designed layout includes

Cheri Bruce-Phipps TTR Sotheby's International Realty

GENEROUS PRICE REDUCTION!!!! This remarkable property has it all. Private 15 plus acres. Beautiful views overlooking Dunn's Cove sunrises. A shore sportsman's dream. Partially wooded, fields of crops, hunting blind and a pier for your fishing vessel. This was a large compound with the Main house, in-law wing and a separate 2 BR guest house w/fireplace and large screened porch. Waterside in-ground

Dawn Lednum Chesapeake Bay Real Estate Plus, LLC