30

5-Bedroom Homes for Sale in Talbot County MD

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  • 301 S Washington St, Easton, MD 21601
    301 S Washington St, Easton, MD 21601
    301 S Washington St, Easton, MD 21601
    /45

    $999,999

    • 5 Beds
    • 3.5 Baths
    • 2,625 Sq Ft

    301 S Washington St, Easton, MD 21601

    Welcome to Pin Oak House, an Easton Federal style white-washed brick property proud to feature the Grand Champion Pin Oak of Talbot County within the confines of its iron-fenced front yard. The spacious corner lot also offers fine gardens, providing colorful foliage nearly year-round. Roses, honeysuckle, tulips, a glorious crepe myrtle, gazebo, irises, stone hardscaping, and a koi pond with

    Agent Photo

    Tiffany Cloud

    Meredith Fine Properties

    (410) 755-7464

    301 S Washington St, Easton, MD 21601
  • 7392 Back St, Newcomb, MD 21653
    7392 Back St, Newcomb, MD 21653
    7392 Back St, Newcomb, MD 21653
    /56

    $725,000

    • 5 Beds
    • 3.5 Baths
    • 2,254 Sq Ft

    7392 Back St, Newcomb, MD 21653

    *Seller to include a 1 year American Home Shield Warranty "Complete" package which covers everything inside your home plus roof coverage!Coastal meets Victorian in this exquisitely renovated home in the quaint waterfront village of Newcomb! The open floor plan exudes a peaceful vibe in every room--airy, light color palette, incredible indoor-outdoor living spaces. This home is all about

    Agent Photo

    Tiffany Cloud

    Meredith Fine Properties

    (410) 304-7796

    7392 Back St, Newcomb, MD 21653
  • 7421 Quaker Neck Rd, Bozman, MD 21612
    7421 Quaker Neck Rd, Bozman, MD 21612
    7421 Quaker Neck Rd, Bozman, MD 21612
    /85

    $2,995,000

    • 6 Beds
    • 4.5 Baths
    • 4,352 Sq Ft

    7421 Quaker Neck Rd, Bozman, MD 21612

    Mortgage savings may be available for buyers of this listing. 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

    Barbara McCaffrey Redfin Corp

    7421 Quaker Neck Rd, Bozman, MD 21612
  • 28092 Glebe Rd, Easton, MD 21601
    28092 Glebe Rd, Easton, MD 21601
    28092 Glebe Rd, Easton, MD 21601
    /39

    $3,275,000

    • 7 Beds
    • 10 Baths
    • 7,077 Sq Ft

    28092 Glebe Rd, Easton, MD 21601

    Miles Away on Murphy’s Point – Discover an unparalleled waterfront retreat at 28092 Glebe Rd, Easton, MD, nestled on approximately ±2.7 picturesque acres. Thoughtfully designed for entertaining, relaxation, and convenient living, this luxurious estate offers expansive indoor and outdoor spaces, exceptional waterfront amenities, and easy access to nearby towns, beaches, and metropolitan

    Coard Benson Benson & Mangold, LLC

    28092 Glebe Rd, Easton, MD 21601
  • 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
  • 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
  • 27473 Westpoint Rd, Easton, MD 21601
    27473 Westpoint Rd, Easton, MD 21601
    27473 Westpoint Rd, Easton, MD 21601
    /62

    $4,499,000

    • 6 Beds
    • 9 Baths
    • 3,700 Sq Ft

    27473 Westpoint Rd, Easton, MD 21601

    Offered for the first time in nearly forty years, Swan Point is the quintessential Eastern Shore estate. Situated on 4.5 +/- acres, with westerly exposure on the Tred Avon River this estate has it all. Private pier with 4’+/- MLW and 400 +/- of waterfrontage. The main house is classically charming and takes full advantage of the sunset water views. Spacious kitchen is complete with high-end

    Chuck Mangold Benson & Mangold, LLC

    27473 Westpoint Rd, Easton, MD 21601
  • 10770 Rich Neck Rd, Claiborne, MD 21624
    10770 Rich Neck Rd, Claiborne, MD 21624
    10770 Rich Neck Rd, Claiborne, MD 21624
    /109

    $8,875,000

    • 7 Beds
    • 7.5 Baths
    • 10,240 Sq Ft

    10770 Rich Neck Rd, Claiborne, MD 21624

    Incredible 300+ acre landmark estate located 5 miles beyond St. Michaels. Over FOUR MILES OF SHORELINE on Eastern Bay, the Miles River and Tilghman Creek. Deep protected anchorage. High land. Sandy beaches. Very livable 10,000+ sq ft home that underwent two-year renovation 2005/2006. 13 ft ceilings on first story and almost10 ft on second story. Formal and informal living areas. Chef's kitchen

    Robert G. Shannahan Shoreline Realty

    10770 Rich Neck Rd, Claiborne, MD 21624
  • 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

    Laura Carney TTR Sotheby's International Realty

    7090 Cooper Point Rd, Bozman, MD 21612
  • 26546 Presquile Dr N, Easton, MD 21601
    26546 Presquile Dr N, Easton, MD 21601
    26546 Presquile Dr N, Easton, MD 21601
    /138

    $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

    Henry Gibbons-Neff Meredith Fine Properties

    26546 Presquile Dr N, Easton, MD 21601
  • 22540 Hardcastle Ln, Bozman, MD 21612
    22540 Hardcastle Ln, Bozman, MD 21612
    22540 Hardcastle Ln, Bozman, MD 21612
    /85

    $3,595,000

    • 5 Beds
    • 6.5 Baths
    • 4,711 Sq Ft

    22540 Hardcastle Ln, Bozman, MD 21612

    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

    22540 Hardcastle Ln, Bozman, MD 21612
  • 11470 Wye Heights Rd, Easton, MD 21601
    11470 Wye Heights Rd, Easton, MD 21601
    11470 Wye Heights Rd, Easton, MD 21601
    /55

    $3,495,000

    • 8 Beds
    • 9 Baths
    • 10,533 Sq Ft

    11470 Wye Heights Rd, Easton, MD 21601

    Nestled on a sprawling 42-acre estate adjacent to the historic Wye Heights Plantation, this stately 8-bedroom mansion offers an unparalleled blend of elegance, comfort, and tranquility. The grand interior is marked by soaring ceilings and meticulous detailing, with an elevator providing convenient access across multiple levels. The heart of the home is designed for both relaxation and

    Chuck Mangold Benson & Mangold, LLC

    11470 Wye Heights Rd, Easton, MD 21601
  • 6020 Sunset Ln, Tilghman, MD 21671
    6020 Sunset Ln, Tilghman, MD 21671
    6020 Sunset Ln, Tilghman, MD 21671
    /50

    $2,795,000

    • 7 Beds
    • 7 Baths
    • 6,377 Sq Ft

    6020 Sunset Ln, Tilghman, MD 21671

    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

    6020 Sunset Ln, Tilghman, MD 21671
  • 28838 Jennings Rd, Easton, MD 21601
    28838 Jennings Rd, Easton, MD 21601
    28838 Jennings Rd, Easton, MD 21601
    /85

    $2,499,900 New Construction

    • 5 Beds
    • 5.5 Baths
    • 5,002 Sq Ft

    28838 Jennings Rd, Easton, MD 21601

    Construction is complete on this beautiful new waterfront home by Laine Street Homes. With 5,000 + finished sqft, 480 sqft of cover outdoor living space, approx. 4.5 acres, and about 320 lnft of frontage on Peach Blossom Creek, with a main level owners suite this home is a must see. Luxury amenities include 7 1⁄2” wide high end wood floors, gourmet kitchen, 48” dual fuel range, built

    Michael Muren Long & Foster Real Estate, Inc.

    28838 Jennings Rd, Easton, MD 21601
  • 6561 Baileys Pond Rd, Easton, MD 21601
    6561 Baileys Pond Rd, Easton, MD 21601
    6561 Baileys Pond Rd, Easton, MD 21601
    /73

    $1,750,000

    • 5 Beds
    • 3.5 Baths
    • 4,919 Sq Ft

    6561 Baileys Pond Rd, Easton, MD 21601

    Welcome to this impeccably maintained and well appointed, five bedroom, approximate 5000 square foot, Colonial home with an interior that combines coastal character with elegant craftsmanship. Located in the sought-after Oxford corridor of Talbot County. This waterfront area invites a relaxed lifestyle with sunset strolls, golf cart rides to the country club, and bike trips to charming Oxford or

    Brian Petzold Benson & Mangold, LLC

    6561 Baileys Pond Rd, Easton, MD 21601
  • 27772 Sharp Rd, Easton, MD 21601
    27772 Sharp Rd, Easton, MD 21601
    27772 Sharp Rd, Easton, MD 21601
    /50

    $13,750,000

    • 5 Beds
    • 9 Baths
    • 13,228 Sq Ft

    27772 Sharp Rd, Easton, MD 21601

    Stock Range Farm spans 350 acres of prime waterfront and is available for purchase in its entirety or with reduced acreage including the main residence, if the buyer so chooses. The property is free of easements and includes development rights, subject to all applicable Talbot County zoning regulations.With vast working farmland and resort-style amenities, this rare gem truly combines

    Laura Carney TTR Sotheby's International Realty

    27772 Sharp Rd, Easton, MD 21601
  • 26698 Arcadia Shores Rd, Easton, MD 21601
    26698 Arcadia Shores Rd, Easton, MD 21601
    26698 Arcadia Shores Rd, Easton, MD 21601
    /61

    $750,000

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

    26698 Arcadia Shores Rd, Easton, MD 21601

    Charming 4-Bedroom Cape Cod on 4 Private Acres with Pool & Sunroom!Welcome to your dream retreat! This beautifully maintained Cape Cod offers 4 spacious bedrooms and 3.5 baths, set on a serene 4-acre lot. Enjoy summer days by the in-ground pool, or unwind in the sunny, four-season sunroom. The inviting living room features a cozy wood stove—perfect for cool evenings. The expansive primary

    Becky Wibberley Coldwell Banker Realty

    26698 Arcadia Shores Rd, Easton, MD 21601
  • 718 Wayside Ave, Easton, MD 21601
    718 Wayside Ave, Easton, MD 21601
    718 Wayside Ave, Easton, MD 21601
    /43

    $441,000

    • 5 Beds
    • 3 Baths
    • 1,950 Sq Ft

    718 Wayside Ave, Easton, MD 21601

    This 4-5 bedroom, 3 full bath Colonial is nestled in the highly sought-after Mecklenburg community, just minutes from downtown Easton and Route 50. The home has undergone numerous updates.As you enter, you'll be captivated by the open-concept design, enhanced by the installation of an industrial steel beam. The living room, featuring a beautiful bay window, boasts a newly rebuilt

    Amy Kling Meredith Fine Properties

    718 Wayside Ave, Easton, MD 21601
  • 7347 Shirley Dr, Easton, MD 21601
    7347 Shirley Dr, Easton, MD 21601
    7347 Shirley Dr, Easton, MD 21601
    /29

    $419,000

    • 5 Beds
    • 2 Baths
    • 2,344 Sq Ft

    7347 Shirley Dr, Easton, MD 21601

    Charming Five-Bedroom Home in Easton – Spacious & Inviting! This beautiful five-bedroom, two-bath home has a split level layout that makes sense for everyone! Enter into the foyer warm wood floors that flow through an inviting living room and dining area. You can access the patio and fenced in back yard for picnics and outdoor living. Head into the gallery kitchen with plenty of counter space

    Lisa Spicer ERA Martin Associates

    7347 Shirley Dr, Easton, MD 21601
  • 13543 Rustling Oaks Dr, Wye Mills, MD 21679
    13543 Rustling Oaks Dr, Wye Mills, MD 21679
    13543 Rustling Oaks Dr, Wye Mills, MD 21679
    /77

    $1,295,000

    • 5 Beds
    • 4.5 Baths
    • 7,166 Sq Ft

    13543 Rustling Oaks Dr, Wye Mills, MD 21679

    Five diamond resort living meets the Eastern Shore in a relaxed rural setting. This exquisite one-of-a-kind home is situated on just under an acre enveloped by luscious, manicured landscaping, towering pines and open field. Just minutes away provides boating with Wye River Landing, a large public boat ramp. Add the luxury of marina life just miles away at Kent Narrows, St Michaels, and Oxford.

    Judy Moore Benson & Mangold, LLC

    13543 Rustling Oaks Dr, Wye Mills, MD 21679
  • 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
  • 3860 Main St, Trappe, MD 21673
    3860 Main St, Trappe, MD 21673
    3860 Main St, Trappe, MD 21673
    /58

    $649,000 Open Sun 1PM - 4PM

    • 6 Beds
    • 3.5 Baths
    • 3,112 Sq Ft

    3860 Main St, Trappe, MD 21673

    Beautifully Restored 1890s Victorian in Trappe, MD - 6BR, 3.5BAStunning fully restored 1890s Victorian in the heart of Trappe. This spacious 6-bedroom, 3.5-bath home features a wraparound porch, formal living and dining rooms, a family room, and a marble primary bath. The home offers one gas fireplace for warmth and ambiance, plus four original decorative fireplaces that add timeless

    Gwen Eskridge Coldwell Banker Chesapeake Real Estate Company

    3860 Main St, Trappe, MD 21673
  • 5559 Trafalgar Cir, Tilghman, MD 21671
    5559 Trafalgar Cir, Tilghman, MD 21671
    5559 Trafalgar Cir, Tilghman, MD 21671
    /62

    $600,000

    • 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
  • 11977 Billys Point Ln, Easton, MD 21601
    11977 Billys Point Ln, Easton, MD 21601
    11977 Billys Point Ln, Easton, MD 21601
    /53

    $6,450,000

    • 6 Beds
    • 8 Baths
    • 9,595 Sq Ft

    11977 Billys Point Ln, Easton, MD 21601

    Welcome to Henry’s Retreat, an extraordinary 37-acre waterfront estate overlooking Quarter Cove off the Wye River. Offering over 2,700 feet of shoreline, this stunning property ensures ultimate privacy, breathtaking views, and unforgettable sunsets.Built in 2016, the 8,835 sq. ft. main residence is designed for luxurious living and seamless entertaining, featuring five bedrooms, six full

    Laura Carney TTR Sotheby's International Realty

    11977 Billys Point Ln, Easton, MD 21601
  • 132 S Harrison St, Easton, MD 21601
    132 S Harrison St, Easton, MD 21601
    132 S Harrison St, Easton, MD 21601
    /101

    $1,595,000

    • 5 Beds
    • 5.5 Baths
    • 3,995 Sq Ft

    132 S Harrison St, Easton, MD 21601

    Experience the allure of Chaffinch House nestled in the heart of Easton’s picturesque landscape. Dating back to 1893, this Queen Anne Victorian residence underwent meticulous restoration in 2019, preserving its timeless elegance. Situated on a prime corner lot, it boasts inviting porches ideal for relaxation and entertainment, including a screened-in dining area and a secluded rear porch

    Chuck Mangold Benson & Mangold, LLC

    132 S Harrison St, Easton, MD 21601
  • 29656 Meadow Gate Dr, Easton, MD 21601
    29656 Meadow Gate Dr, Easton, MD 21601
    29656 Meadow Gate Dr, Easton, MD 21601
    /41

    $525,000

    • 5 Beds
    • 3 Baths
    • 2,778 Sq Ft

    29656 Meadow Gate Dr, Easton, MD 21601

    Inviting Colonial presenting 2,778 square feet, 5 bedrooms, 3 full baths, and a 2-car garage in sought-after Bretridge. A charming front porch sets the tone as you enter the home, where laminate floors span the traditional main level. The grand foyer opens to a formal living room on one side and an elegant dining room on the other, adorned with wainscoting, chair rail details, and a modern

    Bob Lucido Keller Williams Lucido Agency

    29656 Meadow Gate Dr, Easton, MD 21601
  • 21486 Mission Rd, Tilghman, MD 21671
    21486 Mission Rd, Tilghman, MD 21671
    21486 Mission Rd, Tilghman, MD 21671
    /35

    $699,000

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

    21486 Mission Rd, Tilghman, MD 21671

    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

    21486 Mission Rd, Tilghman, MD 21671
  • 29890 Londyn Ln, Easton, MD 21601
    29890 Londyn Ln, Easton, MD 21601
    29890 Londyn Ln, Easton, MD 21601
    /45

    $458,990 New Construction

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

    29890 Londyn Ln, Easton, MD 21601

    Experience 29890 Londyn Lane, a new home in Easton, MD that is under-construction in the new community of Gannon Range. 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

    Justin K Wood D.R. Horton Realty of Virginia, LLC

    29890 Londyn Ln, Easton, MD 21601
  • 5520 Leeward Ln, Tilghman, MD 21671
    5520 Leeward Ln, Tilghman, MD 21671
    5520 Leeward Ln, Tilghman, MD 21671
    /83

    $1,375,000

    • 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
  • 5369 Morgans Point Dr, Oxford, MD 21654
    5369 Morgans Point Dr, Oxford, MD 21654
    5369 Morgans Point Dr, Oxford, MD 21654
    /50

    $8,025,000

    • 6 Beds
    • 12 Baths
    • 24,767 Sq Ft

    5369 Morgans Point Dr, Oxford, MD 21654

    Available for private agreement at auction price. This masterpiece of luxury living is set on nearly 7 acres along the picturesque Tred Avon River. The centerpiece is a magnificent 3-level palatial brick home with 6 bedrooms, 7 full baths, 5 half baths, and 7 gas fireplaces. Enjoy the private dock boasting 4 feet of mean low water (MLW), complete with 2 boat lifts, 4 jet ski lifts, and a

    Clifford Meredith Meredith Fine Properties

    5369 Morgans Point Dr, Oxford, MD 21654
Maryland Talbot County

5-Bedroom Homes for Sale in Talbot County, MD

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