Newest Homes for Sale in Sherwood, MD

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  $489,888

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,710 Sq Ft

  5654 Trafalgar Cir, Tilghman, MD 21671

  Kim Crouch Ozman Benson & Mangold, LLC

  5654 Trafalgar Cir, Tilghman, MD 21671
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  /43

  $529,888

  New Construction

  • 3 Beds
  • 2 Baths
  • 2,068 Sq Ft

  5648 Trafalgar Cir, Tilghman, MD 21671

  Built in 2025, this new construction home offers the best of Eastern Shore living in the water-privileged community of Tilghman on the Chesapeake. Enjoy the ease of one-level living and a thoughtfully designed split-bedroom floor plan. The welcoming covered front porch opens to a bright entry foyer leading to the spacious, open-concept living area. The kitchen boasts granite countertops, a center

  Kim Crouch Ozman Benson & Mangold, LLC

  5648 Trafalgar Cir, Tilghman, MD 21671
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  $1,099,000

  • 3 Beds
  • 3 Baths
  • 3,853 Sq Ft

  6670 Tilghman Island Rd, Sherwood, MD 21665

  Reduced Price! Amazing opportunity to be on the water in Talbot County. Waterfront home situated on Back Creek in Sherwood. Conveniently located near St Michaels and Tilghman Island, the property includes views of sunsets over Poplar Island and is located minutes from restaurants, and shopping. Interior features include hickory hardwood floors, custom built-ins, crown molding, and recessed

  

  Larry Brennan

  TTR Sotheby's International Realty

  6670 Tilghman Island Rd, Sherwood, MD 21665
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  /50

  $1,150,000

  • 4 Beds
  • 2.5 Baths
  • 3,040 Sq Ft

  21477 Island Club Rd, Tilghman, MD 21671

  PRICE IMPROVEMENT*** Welcome to waterfront living at its finest on picturesque Tilghman Island! This beautifully maintained 3,040 sq ft Colonial offers stunning open water views and a lifestyle of comfort, elegance, and ease. Boasting four spacious bedrooms and two and a half baths, this home features a flowing floor plan with natural light, generous living spaces, and a perfect blend of indoor

  Cheri Bruce-Phipps TTR Sotheby's International Realty

  21477 Island Club Rd, Tilghman, MD 21671
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  $3,700,000

  • 5 Beds
  • 7 Baths
  • 5,554 Sq Ft

  21721 Heavenly Haven Rd, Sherwood, MD 21665

  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

  21721 Heavenly Haven Rd, Sherwood, MD 21665
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  $6,800,000

  $700K PRICE DROP

  • 5 Beds
  • 6 Baths
  • 10,000 Sq Ft

  7090 Cooper Point Rd, Bozman, MD 21612

  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

  7090 Cooper Point Rd, Bozman, MD 21612
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  $554,990

  New Construction

  • 3 - 4 Beds
  • 2 - 3 Baths
  • 1,795+ Sq Ft

  Sussex Plan at Tilghman on Chesapeake, Tilghman Island, MD 21671

  Gemcraft Homes Builder

  21600 Island Club Rd Unit 36449305, Tilghman Island, MD 21671
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  $509,990

  New Construction

  • 3 - 4 Beds
  • 2 Baths
  • 1,710+ Sq Ft

  New Castle Plan at Tilghman on Chesapeake, Tilghman Island, MD 21671

  Gemcraft Homes Builder

  21600 Island Club Rd Unit 36475353, Tilghman Island, MD 21671
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  /30

  $435,500

  Open Sat 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,834 Sq Ft

  6403 Bozman Neavitt Rd, Neavitt, MD 21652

  Located about 12 miles from St Michaels, this home is in Neavitt, a charming village of 60+ houses at the end of a peninsula. It's in another, quieter world. The village has its own park and playground, a public landing with a launch for canoes, and an active community association. 6403 was renovated and expanded in 2011 and the layout adapted for modern living, with light-filled rooms, a

  Joan Wetmore TTR Sotheby's International Realty

  6403 Bozman Neavitt Rd, Neavitt, MD 21652
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  /60

  $8,495,000

  • 6 Beds
  • 11 Baths
  • 17,402 Sq Ft

  8620 Bozman Neavitt Rd, Saint Michaels, MD 21663

  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

  8620 Bozman Neavitt Rd, Saint Michaels, MD 21663
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  /10

  $72,500

  $8K PRICE DROP

  • Land
  • 13,068 Sq Ft
  • $241,667 per Acre

  21472 Willey Rd, Tilghman, MD 21671

  Tilghman Island. Clear level building lot with public sewer available. The perfect spot for your new vacation / retirement home. Excellent opportunity to make your island dream come true.

  

  John McGlannan

  Meredith Fine Properties

  21472 Willey Rd, Tilghman, MD 21671

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