31

Homes for Sale in Talbot County MD with 5-Bedrooms

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  • 28715 Jacks Field Rd, Wye Mills, MD 21679
    28715 Jacks Field Rd, Wye Mills, MD 21679
    28715 Jacks Field Rd, Wye Mills, MD 21679
    /27

    $949,000

    • 5 Beds
    • 3 Baths
    • 2,981 Sq Ft

    28715 Jacks Field Rd, Wye Mills, MD 21679

    Set on a peaceful two-acre lot in Wye Mills, 28715 Jacks Field Road has been thoughtfully updated from top to bottom, offering the space, functionality, and modern finishes today’s buyers are looking for. This spacious five-bedroom, three-bath home features a newly reimagined interior with new flooring throughout, custom blinds, and a series of high-impact upgrades that elevate both everyday

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (410) 593-1432

    28715 Jacks Field Rd, Wye Mills, MD 21679
  • 5559 Trafalgar Cir, Tilghman, MD 21671
    5559 Trafalgar Cir, Tilghman, MD 21671
    5559 Trafalgar Cir, Tilghman, MD 21671
    /75

    $569,000

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

    5559 Trafalgar Cir, Tilghman, MD 21671

    TILGHMAN ISLAND.Welcome to this beautiful and spacious 5-bedroom, 3.5-bath single-family home located in the highly sought-after Tilghman on Chesapeake community. Designed for modern comfort and relaxed island living, this home offers an open-concept floor plan filled with abundant natural light and elegant finishes throughout. The gourmet kitchen is a true centerpiece, featuring granite

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    (410) 834-0959

    5559 Trafalgar Cir, Tilghman, MD 21671
  • 228 Perry Cabin Dr Unit 228 / 226, Saint Michaels, MD 21663
    228 Perry Cabin Dr Unit 228 / 226, Saint Michaels, MD 21663
    228 Perry Cabin Dr Unit 228 / 226, Saint Michaels, MD 21663
    /119

    $1,995,000 Open Sat 10AM - 12PM

    • 6 Beds
    • 6 Baths
    • 4,089 Sq Ft

    228 Perry Cabin Dr Unit 228 / 226, Saint Michaels, MD 21663

    Check out the NEW aerial photos! An exceptional opportunity in The Homes at Perry Cabin -- a rare double residence offering approximately 4,000 square feet, six bedrooms, and six full baths in a premier Saint Michaels waterfront community. adjacent to the renowned Inn at Perry Cabin and overlooking Fogg Cove just off the Miles River. This turnkey home features expansive living areas and a

    Agent Photo

    Maureen McHugh

    Chesapeake Bay Real Estate Plus, LLC

    (877) 709-5322

    228 Perry Cabin Dr Unit 228 / 226, Saint Michaels, MD 21663
  • 8749 Harper Way Unit 36203248, Easton, MD 21601
    8749 Harper Way Unit 36203248, Easton, MD 21601
    8749 Harper Way Unit 36203248, Easton, MD 21601
    /44

    $454,990 New Construction

    • 5 Beds
    • 3 Baths
    • 2,511 Sq Ft

    HAYDEN Plan at Gannon Range, Easton, MD 21601

    The Hayden, a 2,511 square foot unique two-story home, offers five bedrooms, one located on the first floor, three full bathrooms, a flex room, a loft, and a two-car garage. The home’s welcoming foyer offers two coat closets and creates the perfect space to greet your guests. In the front of the home, the flex room with an abundance of natural light could be used as a home office or a den. Past

    D.R. Horton Builder
    8749 Harper Way Unit 36203248, Easton, MD 21601
  • 6010 Shipyard Ln, Easton, MD 21601
    6010 Shipyard Ln, Easton, MD 21601
    6010 Shipyard Ln, Easton, MD 21601
    /71

    $9,900,000

    • 5 Beds
    • 6 Baths
    • 14,935 Sq Ft

    6010 Shipyard Ln, Easton, MD 21601

    Situated on one of the finest residential parcels in the country, Ship’s Point, is an estate with few rivals anywhere, at any price. The completely private 13+/- acre estate includes a deep water pier, and 270-degree views at the confluence of Trippe’s Creek and the Tred Avon River. The south-west facing manor house has been meticulously renovated by renowned builder Winchester Construction. A

    Chuck Mangold Benson & Mangold, LLC

    6010 Shipyard Ln, Easton, MD 21601
  • 4108 Saulsbury Ln, Trappe, MD 21673
    4108 Saulsbury Ln, Trappe, MD 21673
    4108 Saulsbury Ln, Trappe, MD 21673
    /36

    $2,500,000

    • 5 Beds
    • 1 Bath

    4108 Saulsbury Ln, Trappe, MD 21673

    Discover one of Talbot Countys rare farms that combines productive farmland, waterfront, and exceptional recreational opportunities. This 105.72 acre agricultural property features approximately 80 acres of tillable ground and is well-suited for continued farming, income production, or long-term land investment. The open farmland is framed by wooded perimeter lines with a mixture of mature

    Casey Kennedy Whitetail Properties Real Estate

    4108 Saulsbury Ln, Trappe, MD 21673
  • 5995 Elston Shore Rd, Neavitt, MD 21652
    5995 Elston Shore Rd, Neavitt, MD 21652
    5995 Elston Shore Rd, Neavitt, MD 21652
    /42

    $3,295,000

    • 5 Beds
    • 4.5 Baths
    • 4,843 Sq Ft

    5995 Elston Shore Rd, Neavitt, MD 21652

    "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

    5995 Elston Shore Rd, Neavitt, MD 21652
  • 110 N Morris St, Oxford, MD 21654
    110 N Morris St, Oxford, MD 21654
    110 N Morris St, Oxford, MD 21654
    /65

    $1,295,000

    • 5 Beds
    • 5.5 Baths
    • 3,574 Sq Ft

    110 N Morris St, Oxford, MD 21654

    Incredible opportunity to own a circa 1875 home in Oxford's Historic District that has been renovated with a separate 2 bedroom apartment with views of Town Creek. Formerly a Bed and Breakfast, it features 2 first floor bedrooms with 1 and 1/2 baths and 3 second floor bedrooms each with its own full bath. Entire exterior has been newly painted and most of the windows have been replaced. A lovely

    Jane McCarthy Benson & Mangold, LLC

    110 N Morris St, Oxford, MD 21654
  • 6448 Partridge Ln, Royal Oak, MD 21662
    6448 Partridge Ln, Royal Oak, MD 21662
    6448 Partridge Ln, Royal Oak, MD 21662
    /49

    $3,495,000

    • 6 Beds
    • 6.5 Baths
    • 3,864 Sq Ft

    6448 Partridge Ln, Royal Oak, MD 21662

    SERENE VIEWS AWAIT YOU AT YOUR EXCLUSIVE WATERFRONT , GORGEOUS ACRES ON PRIVATE MAJESTIC PENINSULA IN BETWEEN THE COASTAL TOWNS ST MICHAELS , EASTON. JUST A SHORT DRIVE TO ITS SHOPS, RESTAURANTS, CAFES, MUSEUMS AND ALL THE AREA HAS TO OFFER.THIS FABULOUS PROPERTY LETS YOU EXPERIENCE EASTERN SHORE LIFE STYLE AS ITS BEST. OPERATED AS A SUCESSFUL VACATION RENTAL IT HAS GONE THRU VARIOUS

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    6448 Partridge Ln, Royal Oak, MD 21662
  • 9629 Bantry Rd, Easton, MD 21601
    9629 Bantry Rd, Easton, MD 21601
    9629 Bantry Rd, Easton, MD 21601
    /38

    $729,900

    • 5 Beds
    • 4 Baths
    • 3,328 Sq Ft

    9629 Bantry Rd, Easton, MD 21601

    Located in the desirable Bantry Community, this classic colonial sits on a 5± acre lot and offers a spacious, well-designed layout ideal for everyday living and entertaining. The home features five bedrooms, along with two full and two half baths. The main level offers hardwood flooring throughout most of the space, a formal dining room, and multiple inviting living areas highlighted by two

    Chuck Mangold Benson & Mangold, LLC

    9629 Bantry Rd, Easton, MD 21601
  • 26546 Presquile Dr N, Easton, MD 21601
    26546 Presquile Dr N, Easton, MD 21601
    26546 Presquile Dr N, Easton, MD 21601
    /97

    $8,400,000

    • 7 Beds
    • 8 Baths
    • 8,001 Sq Ft

    26546 Presquile Dr N, Easton, MD 21601

    Presquile Manor House, originally built by the Lloyd Family circa 1800 as one of their three Plantation Houses, sits up high on the Wye River with due West Exposure. The Main House has recently gone through a two-year renovation process from top to bottom by West & Callahan Construction and Peter Zimmerman Architects Inc, with much thought and care to keep all of the historic attributes that this

    Henry Gibbons-Neff Meredith Fine Properties

    26546 Presquile Dr N, Easton, MD 21601
  • 9180 Saint Michaels Rd, Saint Michaels, MD 21663
    9180 Saint Michaels Rd, Saint Michaels, MD 21663
    9180 Saint Michaels Rd, Saint Michaels, MD 21663
    /66

    $1,685,000 Open Sat 1PM - 2:45PM

    • 5 Beds
    • 5 Baths
    • 4,728 Sq Ft

    9180 Saint Michaels Rd, Saint Michaels, MD 21663

    UNIQUE PROPERTY RIGHT OUTSIDE OF HISTORIC ST MICHAELS TOWN LIMITS ACROSS THE LINK AT PERRY CABIN. THIS FABULOUS HOME OFFERS SPACE FOR GATHERINGS WITH FAMILY OR FRIENDS BUT ALSO FEELS COZY FOR EMPTY NESTERS THAT LOVE TO ENTERTAIN. THERE ARE NO RESTRICTIONS THAT PROHIBIT VACATION RENTAL, THERE SHOULD BE SPACE FOR AN INGROUND POOL .ORIGINALLY BUILD IN 1973 THE CURRENT OWNER GUTTED THE HOME, ALL

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    9180 Saint Michaels Rd, Saint Michaels, MD 21663
  • 21552 Chicken Point Rd, Tilghman, MD 21671
    21552 Chicken Point Rd, Tilghman, MD 21671
    21552 Chicken Point Rd, Tilghman, MD 21671
    /23

    $995,000

    • 5 Beds
    • 2 Baths
    • 2,655 Sq Ft

    21552 Chicken Point Rd, Tilghman, MD 21671

    Located minutes from St. Michaels this waterfront property is a boater's dream. Tilghman, is a small island big on history, nature and local lore. Situated just over the Knapps Narrows Bridge this home offers a main house with first floor master suite. The first floor is open with custom details and just perfect for hosting friends and family. A custom spiral staircase leads to a second floor

    Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

    21552 Chicken Point Rd, Tilghman, MD 21671
  • 205 Cherry St, St. Michaels, MD 21663
    205 Cherry St, St. Michaels, MD 21663
    205 Cherry St, St. Michaels, MD 21663
    /64

    $2,575,000

    • 5 Beds
    • 8.5 Baths
    • 4,394 Sq Ft

    205 Cherry St, St. Michaels, MD 21663

    205 Cherry Street is one of the most prestigious addresses in historic St. Michaels. Originally built as a single-family residence, it currently operates as an Inn. It is being marketed both as a 7 bedroom inn and also as a single family residence, offering 5 bedrooms (including the first floor primary bedroom suite). The original living room/office with fireplaces on the first floor are

    Robert Lacaze TTR Sotheby's International Realty

    205 Cherry St, St. Michaels, MD 21663
  • 4108 Saulsbury Rd, Trappe, MD 21673
    4108 Saulsbury Rd, Trappe, MD 21673
    4108 Saulsbury Rd, Trappe, MD 21673
    /32

    $2,500,000

    • 5 Beds
    • 1 Bath
    • 2,278 Sq Ft

    4108 Saulsbury Rd, Trappe, MD 21673

    Discover one of Talbot County’s rare farms that combines productive farmland, waterfront, and exceptional recreational opportunities. This 105.72-acre agricultural property features approximately 80± acres of tillable ground and is well suited for continued farming, income production, or long-term land investment. The open farmland is framed by wooded perimeter lines with a mixture of mature

    James Young VYBE Realty

    4108 Saulsbury Rd, Trappe, MD 21673
  • 4096 Main St, Trappe, MD 21673
    4096 Main St, Trappe, MD 21673
    4096 Main St, Trappe, MD 21673
    /69

    $364,900 Open Sat 10:30AM - 12:30PM

    • 6 Beds
    • 2.5 Baths
    • 3,446 Sq Ft

    4096 Main St, Trappe, MD 21673

    Historic Farmhouse with Significant Value-Add Potential Built in 1919 and offering approximately 3,448 square feet, this stately farmhouse sits on a .44-acre lot and presents a rare opportunity for investors or renovation enthusiasts to restore a historic property with substantial upside. The home features many original architectural elements, including hardwood floors, crown molding, multiple

    Donna Harrington Coldwell Banker Realty

    4096 Main St, Trappe, MD 21673
  • 22707 Marshall Ln, Wittman, MD 21676
    22707 Marshall Ln, Wittman, MD 21676
    22707 Marshall Ln, Wittman, MD 21676
    /43

    $1,995,000 Open Sat 10AM - 12PM

    • 5 Beds
    • 3.5 Baths
    • 4,310 Sq Ft

    22707 Marshall Ln, Wittman, MD 21676

    Private Harris Creek waterfront with pool, pier boat lift and deep water access—ideal for boating kayaking and quiet days on the water. Five bedrooms and three-and-a-half baths designed for a relaxed yet refined Eastern Shore lifestyle. Featuring sun-filled interiors feature red oak floors custom built-ins multiple fireplaces and wide water views. The kitchen is designed for gathering with

    Kathy Christensen TTR Sotheby's International Realty

    22707 Marshall Ln, Wittman, MD 21676
  • 7508 Cooper Point Rd, Bozman, MD 21612
    7508 Cooper Point Rd, Bozman, MD 21612
    7508 Cooper Point Rd, Bozman, MD 21612
    /116

    $7,500,000

    • 6 Beds
    • 8 Baths
    • 8,476 Sq Ft

    7508 Cooper Point Rd, Bozman, MD 21612

    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

    7508 Cooper Point Rd, Bozman, MD 21612
  • 26698 Arcadia Shores Rd, Easton, MD 21601
    26698 Arcadia Shores Rd, Easton, MD 21601
    26698 Arcadia Shores Rd, Easton, MD 21601
    /71

    $700,000

    • 5 Beds
    • 3.5 Baths
    • 2,306 Sq Ft

    26698 Arcadia Shores Rd, Easton, MD 21601

    Charming 5-Bedroom Cape Cod on 4 Private Acres with Pool, Sunroom & Endless Outdoor BeautyWelcome to your dream retreat! Tucked away on 4 private, park-like acres, this beautifully maintained 5-bedroom, 3.5-bath Cape Cod blends timeless charm with thoughtful modern updates. Relax or entertain with ease—whether you're enjoying summer afternoons by the in-ground pool (with a 20-year liner, only

    Becky Wibberley Coldwell Banker Realty

    26698 Arcadia Shores Rd, Easton, MD 21601
  • 21486 Mission Rd, Tilghman, MD 21671
    21486 Mission Rd, Tilghman, MD 21671
    21486 Mission Rd, Tilghman, MD 21671
    /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 originally used as a fishing lodge for many years. The property sits on 2 acres, has public sewer and well water and consists of three buildings which are: The original main building, the detached garage and a shed/storage building. The buildings hold virtually no value unless an extensive historic renovation were completed, but the

    Monica Penwell TTR Sotheby's International Realty

    21486 Mission Rd, Tilghman, MD 21671
  • 21485 Island Club Rd, Tilghman, MD 21671
    21485 Island Club Rd, Tilghman, MD 21671
    21485 Island Club Rd, Tilghman, MD 21671
    /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
  • 7049 & 7047 Acorn Aly, Royal Oak, MD 21662
    7049 & 7047 Acorn Aly, Royal Oak, MD 21662
    7049 & 7047 Acorn Aly, Royal Oak, MD 21662
    /40

    $2,095,000

    • 6 Beds
    • 3.5 Baths
    • 1,454 Sq Ft

    7049 & 7047 Acorn Aly, Royal Oak, MD 21662

    **Discover Your Waterfront Oasis in Royal Oak** Nestled in the charming town of Royal Oak, these exceptional waterfront properties present breathtaking views of Oak Creek, conveniently located near the Miles River and the renowned Chesapeake Bay. Positioned between the picturesque communities of Saint Michael’s and Easton, this rare gem boasts approximately 541 feet of pristine water frontage,

    Blaine Williamson McClain-Williamson Realty, LLC

    7049 & 7047 Acorn Aly, Royal Oak, MD 21662
  • 8781 Tilghman Island Rd, Wittman, MD 21676
    8781 Tilghman Island Rd, Wittman, MD 21676
    8781 Tilghman Island Rd, Wittman, MD 21676
    /60

    $3,650,000 Open House 4/11

    • 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
  • 5440 Ferry Neck Rd, Royal Oak, MD 21662
    5440 Ferry Neck Rd, Royal Oak, MD 21662
    5440 Ferry Neck Rd, Royal Oak, MD 21662
    /69

    $2,795,000

    • 5 Beds
    • 5.5 Baths
    • 4,602 Sq Ft

    5440 Ferry Neck Rd, Royal Oak, MD 21662

    Welcome to ‘Drake’s Landing’! Beautifully sited on 20 picturesque acres on the shores of Irish Creek, this 4,602 sq. ft .completely renovated (2021) waterfront estate offers the perfect blend of casual elegance and thoughtful design. The main level welcomes with expansive water views and features a guest bedroom with ensuite bath, a cozy family room (or den/office), and a gracious living room

    Laura Carney TTR Sotheby's International Realty

    5440 Ferry Neck Rd, Royal Oak, MD 21662
  • 21721 Heavenly Haven Rd, Sherwood, MD 21665
    21721 Heavenly Haven Rd, Sherwood, MD 21665
    21721 Heavenly Haven Rd, Sherwood, MD 21665
    /46

    $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
  • 7090 Cooper Point Rd, Bozman, MD 21612
    7090 Cooper Point Rd, Bozman, MD 21612
    7090 Cooper Point Rd, Bozman, MD 21612
    /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 by a

    Laura Carney TTR Sotheby's International Realty

    7090 Cooper Point Rd, Bozman, MD 21612
  • 8620 Bozman Neavitt Rd, Saint Michaels, MD 21663
    8620 Bozman Neavitt Rd, Saint Michaels, MD 21663
    8620 Bozman Neavitt Rd, Saint Michaels, MD 21663
    /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
  • 27295 Southside Island Creek Rd, Trappe, MD 21673
    27295 Southside Island Creek Rd, Trappe, MD 21673
    27295 Southside Island Creek Rd, Trappe, MD 21673
    /91

    $8,750,000

    • 6 Beds
    • 6 Baths
    • 9,566 Sq Ft

    27295 Southside Island Creek Rd, Trappe, MD 21673

    Wilderness Estate- REVISED OFFERING INCLUDES 5 PARCELS 6.27.25- This quintessential Eastern Shore farm is located along the Choptank River in Trappe, Maryland. Comprised of 234 acres, with original structures that are impeccably well-kept and improved with modern amenities, The Wilderness provides a unique opportunity to enjoy the best of the Eastern Shore. Surrounded by open space and preserved

    Coard Benson Benson & Mangold, LLC

    27295 Southside Island Creek Rd, Trappe, MD 21673
  • 607 A&B North St, Easton, MD 21601
    607 A&B North St, Easton, MD 21601
    607 A&B North St, Easton, MD 21601
    /34

    $924,000 Open Sat 10AM - 12PM

    • 6 Beds
    • 6 Baths
    • 3,400 Sq Ft

    607 A&B North St, Easton, MD 21601

    This custom-built duplex, located in the heart of historic Easton, is a one-of-a-kind investment opportunity. Featuring three bedrooms and two and a half baths in each home, the homes offer an ensuite primary bedroom complete with a walk-in closet and private bath. Designed with modern luxury in mind, it includes new stainless-steel appliances, Marvin windows, a rich wood front door, and high-end

    Jana Meredith Meredith Fine Properties

    607 A&B North St, Easton, MD 21601
  • 8612 Tilghman Island Rd, Wittman, MD 21676
    8612 Tilghman Island Rd, Wittman, MD 21676
    8612 Tilghman Island Rd, Wittman, MD 21676
    /76

    $7,900,000 Coming Soon

    • 8 Beds
    • 5.5 Baths
    • 9,051 Sq Ft

    8612 Tilghman Island Rd, Wittman, MD 21676

    "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

    8612 Tilghman Island Rd, Wittman, MD 21676
  • 5520 Leeward Ln, Tilghman, MD 21671
    5520 Leeward Ln, Tilghman, MD 21671
    5520 Leeward Ln, Tilghman, MD 21671
    /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
Maryland Talbot County

5-Bedroom Homes for Sale in Talbot County, MD

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