Newest Homes for Sale in Sherwood, MD

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  /25

  $850,000 Coming Soon

  • 4 Beds
  • 2.5 Baths
  • 2,286 Sq Ft

  5489 Rude Ave, Tilghman, MD 21671

  Spacious 3,000 sqft two-story waterfront home on 3/4 acre parcel on Harris Creek where it joins the Choptank River for an 11-mile view to Cambridge. House is brick and block on the first level with redwood siding on the second level in board and batten style. 150ft heavily built and reinforced bulkhead waterfront with recently renovated 75ft long dock. Second floor includes four bedrooms with

  Leo Kuneman Meredith Fine Properties

  5489 Rude Ave, Tilghman, MD 21671
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  /81

  $3,100,000

  • 4 Beds
  • 3.5 Baths
  • 4,035 Sq Ft

  23961 Lynnewood Dr, Saint Michaels, MD 21663

  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

  23961 Lynnewood Dr, Saint Michaels, MD 21663
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  /36

  $385,000

  • 2 Beds
  • 1.5 Baths
  • 1,364 Sq Ft

  8805 Cummings Rd, Wittman, MD 21676

  Located in the waterfront village of Wittman, close to the public landing and county park, this beautifully crafted two-story cottage blends charm and character with thoughtful design. The home features 2 bedrooms, 1.5 baths, multiple living areas, 2 office spaces, and generous storage. Open beams, wood floors, and architectural details create a warm, inviting atmosphere throughout. Elevated and

  Wink Cowee Benson & Mangold, LLC

  8805 Cummings Rd, Wittman, MD 21676
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  /32

  $549,000

  • 9 Beds
  • 2.5 Baths
  • 5,389 Sq Ft

  21486 Mission Rd, Tilghman, MD 21671

  This historic property known as "The Elms" was built in 1900 and used as a fishing lodge for many years. The property sits on 2 acres, has public sewer and well water. The buildings hold virtually no value unless and extensive historic renovation were completed. Tilghman is an historic waterfront town that features a waterman's museum, marina, many restaurants, established

  Monica Penwell TTR Sotheby's International Realty

  21486 Mission Rd, Tilghman, MD 21671
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  /83

  $2,499,000

  • 5 Beds
  • 4.5 Baths
  • 4,303 Sq Ft

  21485 Island Club Rd, Tilghman, MD 21671

  Discover the essence of refined Eastern Shore living in this meticulously renovated contemporary waterfront retreat, gracefully set along the tranquil shores of Harris Creek and looking out to the Choptank River. Every detail of this remarkable home exemplifies elegance. Step inside to a breathtaking panorama of water views framed by expansive windows that fill the home with ethereal lighting.

  Alicia Gannon Dulin Benson & Mangold, LLC

  21485 Island Club Rd, Tilghman, MD 21671
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  /14

  $325,000

  • 3 Beds
  • 2 Baths
  • 3,924 Sq Ft

  22314 Pot Pie Rd, Wittman, MD 21676

  Potential Rental Opportunity in Wittman, MD Positioned in the desirable community of Wittman, this 3 bedroom, 2 bath home on 0.84± acres presents a compelling opportunity for investors seeking potential rental income in Talbot County. The property offers comfortable living space, a rural Eastern Shore setting, and proximity to key employment, recreation, and service hubs. In addition to the

  Shawn Moore Meredith Fine Properties

  22314 Pot Pie Rd, Wittman, MD 21676
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  /72

  $765,000

  • 3 Beds
  • 2.5 Baths
  • 2,240 Sq Ft

  6660 Reeses Pride Rd, Sherwood, MD 21665

  Your Eastern Shore paradise awaits! This awesomely updated, meticulously maintained, classic colonial-style home is like a breath of fresh air. Located on a full 2 acre parcel, in the heart of the sought after Deep Harbour Farm community, custom features include a lovely private backyard oasis, designed around an 18’x32’ inground salt-water pool, and surrounded by all new, high-quality fencing,

  

  John McGlannan

  Meredith Fine Properties

  (410) 431-3957

  6660 Reeses Pride Rd, Sherwood, MD 21665
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  /44

  $1,195,000

  • 3 Beds
  • 3 Baths
  • 1,612 Sq Ft

  24318 Oakwood Park Rd, Saint Michaels, MD 21663

  Welcome to Old House Cove Waterfront Retreat in St. Michaels, MDNestled on nearly half an acre with scenic frontage along Old House Cove, this quintessential Eastern Shore property offers a rare combination of waterfront serenity, literary history, and timeless design. The expansive parcel provides privacy in a highly desirable location, just minutes from the heart of St. Michael’s—one of

  Kathleen Eder Compass

  24318 Oakwood Park Rd, Saint Michaels, MD 21663
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  /49

  $499,888 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
• 

  

  /43

  $544,888 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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  /60

  $3,795,000

  • 5 Beds
  • 5.5 Baths
  • 6,487 Sq Ft

  8781 Tilghman Island Rd, Wittman, MD 21676

  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

  8781 Tilghman Island Rd, Wittman, MD 21676
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  /44

  $318,000

  • 3 Beds
  • 1.5 Baths
  • 1,376 Sq Ft

  10437 Main St, Claiborne, MD 21624

  BEST KEPT SECRET OF THE EASTERN SHORE ! CHARMING WATERFRONT VILLAGE WITH COMMUNITY CENTER AND FABULOUS WATER ACCESS JUST 4 MILES FROM HISTORIC ST MICHAELS. THE HISTORIC STEAMBOAT LANDING IS THE VILLAGERS WATERFRONT HANG OUT. THERE IS ALSO A POPLUAR SANDY BEACH TO ENJOY THE BAY.THIS SPACIOUS SOLID HOME HAS BEEN UPDATED WITH REPLACMENT WINDOWS, NEW SIDING, HVAC. THE INTERIOR IS IN NEED OF SOME

  Cornelia Heckenbach Long & Foster Real Estate, Inc.

  10437 Main St, Claiborne, MD 21624
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  /43

  $2,595,000

  • 3 Beds
  • 3.5 Baths
  • 2,400 Sq Ft

  6060 Elston Shore Rd, Neavitt, MD 21652

  This extraordinary 10.6± acre property on the Choptank River and Harris Creek has been fully renovated, offering 1,500± feet of waterfrontage, a private 172’ L-shaped pier with boat lift, and sweeping views from nearly every room. The home’s interiors balance craftsmanship with modern convenience. The first-floor kitchen features Kraft Maid cabinetry, granite countertops, and stainless steel

  Chuck Mangold Benson & Mangold, LLC

  6060 Elston Shore Rd, Neavitt, MD 21652
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  /23

  $495,500

  • 2 Beds
  • 1 Bath
  • 960 Sq Ft

  6343 Bozman Neavitt Rd, Neavitt, MD 21652

  UNIQUE COTTAGE IN A GREAT VILLAGE SETING WITH A DOCK PROVIDING ACCESS TO BALL CREEK AND QUICK ACCES TO THE CHESAPEAKE WITH GREAT FISHING AND SAILING! Ready for an updating with good bones this would be a wonderful weekender or short term rental. Typical Eastern Shore rural village with great folks it can even be replaced with the home of your dreams.Dock offers a 3 foot channel and has

  Bill Wieland Benson & Mangold, LLC

  6343 Bozman Neavitt Rd, Neavitt, MD 21652
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  /89

  $2,998,000

  • 4 Beds
  • 6 Baths
  • 5,400 Sq Ft

  9262 Macks Ln, McDaniel, MD 21647

  Just 5-miles outside historic St. Michaels, MD...Classic "Eastern Shore Waterfront Retreat," featuring a substantial 5,400+ sq. ft. home, thoughtfully designed to capture cooling SW summer breezes and spectacular sunset views across the sparkling waters of Harris Creek. Sited on 8.26 private acres w/over 300' of natural "living Shoreline," features of the brick home include high ceilings

  Tom Crouch Benson & Mangold, LLC

  9262 Macks Ln, McDaniel, MD 21647
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  /64

  $1,299,000

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

  6670 Tilghman Island Rd, Sherwood, MD 21665

  Waterfront home situated on Back Creek in Sherwood, offering direct access to the Chesapeake Bay and Choptank Rivers. 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 lighting.

  Larry Brennan TTR Sotheby's International Realty

  6670 Tilghman Island Rd, Sherwood, MD 21665
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  /41

  $575,000

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft

  21869 Albie Rd, Sherwood, MD 21665

  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

  21869 Albie Rd, Sherwood, MD 21665
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  /13

  $164,900

  • 2 Beds
  • 1 Bath
  • 1,540 Sq Ft

  22381 Cooper Ln, Wittman, MD 21676

  Very private setting. Just 10 minutes south of St. Michaels. Make this into a perfect weekend get away home. Conveniently sandwiched between St. Michael's and Tilgman Island and just right off of route 33, you will find this wonderful little opportunity to create your secluded seasonal hideout where you can enjoy all the Eastern Shore has to offer. Fishing, crabbing and swimming are just the

  Joseph Craig Cummings & Co. Realtors

  22381 Cooper Ln, Wittman, MD 21676
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  /50

  $1,200,000

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

  21477 Island Club Rd, Tilghman, MD 21671

  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 and outdoor

  Cheri Bruce-Phipps TTR Sotheby's International Realty

  21477 Island Club Rd, Tilghman, MD 21671
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  /22

  $245,000

  • 2 Beds
  • 1 Bath
  • 1,270 Sq Ft

  22349 Cooper Ln, Wittman, MD 21676

  Charming farmhouse with approximately 1300 sq feet of living space on a large, picturesque lot. Perfect weekend retreat close to St. Michaels, investment property or full time residence. The second level has two bedrooms, walk-in closet, a cozy nook ideal for a home office and a recently fully renovated bathroom. First floor includes a front room suited for an office or additional full bathroom.

  Brian Petzold Benson & Mangold, LLC

  22349 Cooper Ln, Wittman, MD 21676
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  /31

  $365,000

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft

  6135 Summit St, Tilghman, MD 21671

  Welcome to your Eastern Shore getaway, located at 6135 Summit Street, Tilghman, Maryland. This charming property is just a short walk from Tilghman Island's best waterfront attractions, including two marinas and three excellent dining options. This two-bedroom, one-bath home reflects pride of ownership and has been well maintained, making it ready for you to enjoy a slower pace of life on

  

  John McGlannan

  Meredith Fine Properties

  (410) 593-3451

  6135 Summit St, Tilghman, MD 21671
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  /25

  $295,000

  • 3 Beds
  • 1 Bath
  • 1,224 Sq Ft

  21749 Camper Cir, Tilghman, MD 21671

  A fantastic opportunity awaits at 21749 Camper Circle in Tilghman, Maryland. This home is perfect for first-time buyers or investors looking for great value at an affordable price. It features central heating and air conditioning, three spacious bedrooms, and one full bathroom. Enjoy a large sunroom with tile flooring that is conveniently located next to the kitchen. The hardwood floors

  

  John McGlannan

  Meredith Fine Properties

  (410) 498-8659

  21749 Camper Cir, Tilghman, MD 21671
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  /74

  $1,250,000

  • 3 Beds
  • 3 Baths
  • 3,232 Sq Ft

  6050 Sunset Ln, Tilghman, MD 21671

  Exquisitely designed renovation incorporating high end finishes makes this waterfront 3BR, 3B cottage the perfect retreat! Large great room w/dining area, fireplace & multiple seating areas gives you ample spaces to enjoy the broad, westerly views of the bay. The gourmet kitchen & pantry is a chef's dream. Screen room, private pier, separate garage w/ guest house.

  Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

  6050 Sunset Ln, Tilghman, MD 21671
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  /46

  $4,750,000

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

  21721 Heavenly Haven Rd, Sherwood, MD 21665

  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 pool and children's play

  Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

  21721 Heavenly Haven Rd, Sherwood, MD 21665
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  /86

  $7,500,000

  • 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

  Laura Carney TTR Sotheby's International Realty

  7090 Cooper Point Rd, Bozman, MD 21612
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  /94

  $1,995,000

  • 4 Beds
  • 3.5 Baths
  • 2,250 Sq Ft

  23857 Ebb Point Rd, Bozman, MD 21612

  Experience elevated coastal living in this impeccably renovated 2,250 sq ft post-and-beam home, reimagined as a coastal modern contemporary masterpiece by interior designer Hollace Kutay. Known as Oyster Cove for its picturesque 2.5 acre location on Broad Creek, this home is perfectly situated for boaters and kayakers seeking both adventure and tranquility. Enjoy expansive water views from nearly

  Hollace Kutay Meredith Fine Properties

  23857 Ebb Point Rd, Bozman, MD 21612
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  /56

  $585,000

  • 3 Beds
  • 2 Baths
  • 1,761 Sq Ft

  8000 Bozman Neavitt Rd, Bozman, MD 21612

  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

  8000 Bozman Neavitt Rd, Bozman, MD 21612
• 

  $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
• 

  $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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  /35

  $425,000

  • 2 Beds
  • 2 Baths
  • 1,776 Sq Ft

  7651 Main St, Sherwood, MD 21665

  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

  Cornelia Heckenbach Long & Foster Real Estate, Inc.

  7651 Main St, Sherwood, MD 21665
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  /83

  $1,200,000

  • 5 Beds
  • 2.5 Baths
  • 4,214 Sq Ft

  5520 Leeward Ln, Tilghman, MD 21671

  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

  5520 Leeward Ln, Tilghman, MD 21671
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  /3

  $92,000

  • 2 Beds
  • 1 Bath
  • 920 Sq Ft

  9681 Macks Ln, McDaniel, MD 21647

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

  Lesley Jackson EXIT Sunshine Realty

  9681 Macks Ln, McDaniel, MD 21647
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  /57

  $1,150,000

  • 3 Beds
  • 2 Baths
  • 2,642 Sq Ft

  22860 Middle Point Rd, Neavitt, MD 21652

  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

  22860 Middle Point Rd, Neavitt, MD 21652
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  /31

  $469,500

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

  6403 Bozman Neavitt Rd, Neavitt, MD 21652

  Neavitt is a village of +/-seventy houses located at the end of a peninsula surrounded by water. About 11 miles from the shops and restaurants of St Michaels, it is in another, much more peaceful world, with its own park and playground, a public landing with a launch for canoes, and an active community association. Most residents have retired or plan to retire from professional jobs in

  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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  /47

  $1,745,000

  • 6 Beds
  • 6 Baths
  • 4,397 Sq Ft

  6020 Sunset Ln, Tilghman, MD 21671

  Welcome to Tilghman Landing on the Chesapeake Bay! This unique waterview property offers an incredible opportunity, featuring two separate homes with garages with unbelievable views of the Bay!Home #1: 6020 Sunset LaneThis spacious residence offers breathtaking, unobstructed views of the Bay. It includes 3 bedrooms and 2.5 bathrooms, and showcases an open-concept main level with a living

  Melissa Tippett TTR Sotheby's International Realty

  6020 Sunset Ln, Tilghman, MD 21671
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  /24

  $174,900

  • Land
  • 2.49 Acres
  • $70,241 per Acre

  0 Holly Woods Rd, 5, Bay Hundred, MD 21665

  Deep Harbour Farm Sherwood 2.49. Acre Building Lot.This is one of the last remaining building lots available in this wonderful water privileged community.Located at the end of a cul-de-sac on Holly Woods Road just steps away from the community waterfront pier & boat dock. Great opportunity to build the home of your own design now or in the future.

  

  John McGlannan

  Meredith Fine Properties

  (667) 222-5571

  0 Holly Woods Rd, 5, Bay Hundred, MD 21665
• 

  

  /62

  $575,000

  • 5 Beds
  • 3.5 Baths
  • 3,404 Sq Ft

  5559 Trafalgar Cir, Tilghman, MD 21671

  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

  5559 Trafalgar Cir, Tilghman, MD 21671
• 

  

  /10

  $80,000

  • Land
  • 0.3 Acre
  • $266,667 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

  (667) 382-8747

  21472 Willey Rd, Tilghman, MD 21671
• 

  

  /34

  $259,900

  • 3 Beds
  • 1.5 Baths
  • 1,336 Sq Ft

  21907 Sherwood Landing Rd, Sherwood, MD 21665

  First time offered in 60 years! Nestled in the heart of a charming waterfront village, this classic 3-bedroom, 1.5-bath Eastern Shore home exudes timeless appeal. With rich historic character and warm wood floors throughout, it’s ready for your personal touch to bring it back to life. Enjoy partial water views and the convenience of a county pier and kayak launch just down the street, providing

  Wink Cowee Benson & Mangold, LLC

  21907 Sherwood Landing Rd, Sherwood, MD 21665

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