27

Sherwood, MD Homes for Sale with Garage

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  • 5698 Leeward Ln, Tilghman, MD 21671
    5698 Leeward Ln, Tilghman, MD 21671
    5698 Leeward Ln, Tilghman, MD 21671
    /41

    $1,995,000

    • 5 Beds
    • 3.5 Baths
    • 3,906 Sq Ft

    5698 Leeward Ln, Tilghman, MD 21671

    Experience sweeping western-facing views of the Chesapeake Bay from this beautifully renovated waterfront retreat in Tilghman Island. Thoughtfully redesigned and updated in 2023, this exceptional property seamlessly blends refined coastal living with the tranquility and natural beauty of its extraordinary waterfront setting.Inside, the light-filled great room is the heart of the home, with

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    5698 Leeward Ln, Tilghman, MD 21671
  • 5559 Trafalgar Cir, Tilghman, MD 21671
    5559 Trafalgar Cir, Tilghman, MD 21671
    5559 Trafalgar Cir, Tilghman, MD 21671
    /75

    $564,000

    $5K PRICE DROP
    • 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

    5559 Trafalgar Cir, Tilghman, MD 21671
  • 6660 Reeses Pride Rd, Sherwood, MD 21665
    6660 Reeses Pride Rd, Sherwood, MD 21665
    6660 Reeses Pride Rd, Sherwood, MD 21665
    /72

    $749,000

    • 3 Beds
    • 2.5 Baths
    • 2,840 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,

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    6660 Reeses Pride Rd, Sherwood, MD 21665
  • 6670 Tilghman Island Rd, Sherwood, MD 21665
    6670 Tilghman Island Rd, Sherwood, MD 21665
    6670 Tilghman Island Rd, Sherwood, MD 21665
    /64

    $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

    Agent Photo

    Larry Brennan

    TTR Sotheby's International Realty

    6670 Tilghman Island Rd, Sherwood, MD 21665
  • 5648 Trafalgar Cir, Tilghman, MD 21671
    5648 Trafalgar Cir, Tilghman, MD 21671
    5648 Trafalgar Cir, Tilghman, MD 21671
    /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
  • 7090 Cooper Point Rd, Bozman, MD 21612
    7090 Cooper Point Rd, Bozman, MD 21612
    7090 Cooper Point Rd, Bozman, MD 21612
    /86

    $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
  • 21642 Chicken Point Rd, Tilghman, MD 21671
    21642 Chicken Point Rd, Tilghman, MD 21671
    21642 Chicken Point Rd, Tilghman, MD 21671
    /144

    $2,475,000

    $220K PRICE DROP
    • 7 Beds
    • 5.5 Baths
    • 4,151 Sq Ft

    21642 Chicken Point Rd, Tilghman, MD 21671

    Tranquil Waters” is a rare Chesapeake Bay waterfront retreat on Tilghman Island, comprehensively renovated to the highest standard and designed to capture panoramic water views from nearly every room. This extraordinary residence blends refined coastal architecture with the relaxed elegance of Eastern Shore living. Dramatic walls of glass, soaring ceilings, and open living spaces flood the home

    Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

    21642 Chicken Point Rd, Tilghman, MD 21671
  • 7543 Bozman Neavitt Rd, Bozman, MD 21612
    7543 Bozman Neavitt Rd, Bozman, MD 21612
    7543 Bozman Neavitt Rd, Bozman, MD 21612
    /104

    $2,750,000

    • 4 Beds
    • 3 Baths
    • 6,361 Sq Ft

    7543 Bozman Neavitt Rd, Bozman, MD 21612

    This stunning waterfront estate is located just minutes from Historic downtown St. Michaels and offers breathtaking views across Leadenham Creek. Set on 47± picturesque acres, the property combines a beautifully renovated main residence, guest house, private dock, waterside pool and expansive open land in one exceptional Eastern Shore offering. Renovated in 2017, the 3,500± sqft brick residence

    Kim Crouch Ozman Benson & Mangold, LLC

    7543 Bozman Neavitt Rd, Bozman, MD 21612
  • 8658 Cummings Rd, Wittman, MD 21676
    8658 Cummings Rd, Wittman, MD 21676
    8658 Cummings Rd, Wittman, MD 21676
    /45

    $495,000

    • 3 Beds
    • 2 Baths
    • 1,664 Sq Ft

    8658 Cummings Rd, Wittman, MD 21676

    Enjoy the ease of one-level living in this well-maintained rancher, built in 2002 and situated on 2+/- acres in the quaint village of Wittman. Offering 1,662+/- sqft, this 3-bedroom, 2-bath home provides comfortable living with plenty of room to enjoy both inside and out. Hardwood flooring welcomes you into the foyer, which opens to a spacious living room. The kitchen features ample cabinetry,

    Kim Crouch Ozman Benson & Mangold, LLC

    8658 Cummings Rd, 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
  • 9020 Bozman Neavitt Rd, Saint Michaels, MD 21663
    9020 Bozman Neavitt Rd, Saint Michaels, MD 21663
    9020 Bozman Neavitt Rd, Saint Michaels, MD 21663
    /37

    $1,995,000

    • 4 Beds
    • 2.5 Baths
    • 3,028 Sq Ft

    9020 Bozman Neavitt Rd, Saint Michaels, MD 21663

    Just 4 miles (five minutes) outside the historic town of St. Michaels, MD, this 15-acre property is located in an area of large, private waterfront estates. Over 300 ft. of protected shoreline. Westerly exposure...Exceptional Sunset views across the sparkling waters of Harris Creek! 120' x 6' pile-driven pier provides approximately 4' MLW. Sited near the water at the end of a long, tree-lined

    Tom Crouch Benson & Mangold, LLC

    9020 Bozman Neavitt Rd, Saint Michaels, MD 21663
  • 23961 Lynnewood Dr, Saint Michaels, MD 21663
    23961 Lynnewood Dr, Saint Michaels, MD 21663
    23961 Lynnewood Dr, Saint Michaels, MD 21663
    /68

    $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
  • 21485 Island Club Rd, Tilghman, MD 21671
    21485 Island Club Rd, Tilghman, MD 21671
    21485 Island Club Rd, Tilghman, MD 21671
    /83

    $1,950,000

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

    21485 Island Club Rd, Tilghman, MD 21671

    Back on the market due to Buyers unable to fulfill home sale contingency- 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

    Alicia Gannon Dulin Benson & Mangold, LLC

    21485 Island Club Rd, Tilghman, MD 21671
  • 7421 Quaker Neck Rd, Bozman, MD 21612
    7421 Quaker Neck Rd, Bozman, MD 21612
    7421 Quaker Neck Rd, Bozman, MD 21612
    /59

    $1,995,000

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

    7421 Quaker Neck Rd, Bozman, MD 21612

    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

    7421 Quaker Neck Rd, Bozman, MD 21612
  • 8090 Bozman Neavitt Rd, Bozman, MD 21612
    8090 Bozman Neavitt Rd, Bozman, MD 21612
    8090 Bozman Neavitt Rd, Bozman, MD 21612
    /33

    $993,000

    • 3 Beds
    • 2 Baths
    • 1,362 Sq Ft

    8090 Bozman Neavitt Rd, Bozman, MD 21612

    Nestled in the serene enclave of Bozman, this exquisite 1940s bungalow seamlessly blends coastal charm with modern luxury, offering an unparalleled lifestyle for discerning buyers. Spanning 1,362+/- square feet, this detached residence boasts three spacious bedrooms and two elegantly appointed bathrooms, each designed with high-end finishes that elevate everyday living. The country-style kitchen

    Bill Wieland Benson & Mangold, LLC

    8090 Bozman Neavitt Rd, Bozman, MD 21612
  • 21477 Island Club Rd, Tilghman, MD 21671
    21477 Island Club Rd, Tilghman, MD 21671
    21477 Island Club Rd, Tilghman, MD 21671
    /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
  • 5654 Trafalgar Cir, Tilghman, MD 21671
    5654 Trafalgar Cir, Tilghman, MD 21671
    5654 Trafalgar Cir, Tilghman, MD 21671
    /49

    $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
  • 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
  • 23776 Mount Pleasant Landing Cir, Saint Michaels, MD 21663
    23776 Mount Pleasant Landing Cir, Saint Michaels, MD 21663
    23776 Mount Pleasant Landing Cir, Saint Michaels, MD 21663
    /85

    $1,995,000

    • 3 Beds
    • 2 Baths
    • 2,160 Sq Ft

    23776 Mount Pleasant Landing Cir, Saint Michaels, MD 21663

    A wonderful opportunity to purchase an amazing one story waterfront home on an expansive 2.5 acre lot with western exposure on Broad Creek. Many upgrades have been done to make this a special home to enjoy your life of relaxation and pure enjoyment on the Eastern Shore of Maryland! Mount Pleasant is a very sought after St Michaels neighborhood with close proximity to the downtown historic area of

    Leslie Stevenson Shore Living Real Estate

    23776 Mount Pleasant Landing Cir, Saint Michaels, MD 21663
  • 21441 Dogwood Cove Rd, Tilghman, MD 21671
    21441 Dogwood Cove Rd, Tilghman, MD 21671
    21441 Dogwood Cove Rd, Tilghman, MD 21671
    /119

    $1,350,000

    • 3 Beds
    • 2.5 Baths
    • 2,477 Sq Ft

    21441 Dogwood Cove Rd, Tilghman, MD 21671

    Unique Tilghman Island Property. Zoned Residential-Commercial. Situated on a 2.74 acre fenced yard. This 2450 sq ft Stone Rancher has many upgrades, new 2 car garage and 24 new commercial slips. The possibilities are endless....... Vacation Rental, 24 brand new slips, typically rent from 175.00-225.00 monthly. Develop a new fishing center, crabbing tours, sunsets cruises. Let's see what you can

    Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

    21441 Dogwood Cove Rd, Tilghman, MD 21671
  • 9251 Mallard Point Ct, McDaniel, MD 21647
    9251 Mallard Point Ct, McDaniel, MD 21647
    9251 Mallard Point Ct, McDaniel, MD 21647
    /52

    $1,295,000

    $155K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,816 Sq Ft

    9251 Mallard Point Ct, McDaniel, MD 21647

    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

    9251 Mallard Point Ct, McDaniel, MD 21647
  • 6705 Tilghman Island Rd, Sherwood, MD 21665
    6705 Tilghman Island Rd, Sherwood, MD 21665
    6705 Tilghman Island Rd, Sherwood, MD 21665
    /41

    $575,000

    $10K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,424 Sq Ft

    6705 Tilghman Island Rd, Sherwood, MD 21665

    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

    6705 Tilghman Island Rd, Sherwood, MD 21665
  • 7909 Church Neck Rd, Saint Michaels, MD 21663
    7909 Church Neck Rd, Saint Michaels, MD 21663
    7909 Church Neck Rd, Saint Michaels, MD 21663
    /50

    $2,100,000

    $500K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 4,492 Sq Ft

    7909 Church Neck Rd, Saint Michaels, MD 21663

    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

    7909 Church Neck Rd, Saint Michaels, MD 21663
  • 8781 Tilghman Island Rd, Wittman, MD 21676
    8781 Tilghman Island Rd, Wittman, MD 21676
    8781 Tilghman Island Rd, Wittman, MD 21676
    /68

    $2,995,000

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

    8781 Tilghman Island Rd, Wittman, MD 21676

    8781 Tilghman Island Road presents a rare opportunity to own a custom-designed, Daffin-built Chesapeake Bay estate set on 21±acres between historic St. Michaels and Tilghman Island. Constructed with a timeless brick exterior and encompassing approximately 6,500± square feet, this five-bedroom, five-and-a-half-bath residence was thoughtfully designed to embrace its extraordinary waterfront

    Chuck Mangold Benson & Mangold, LLC

    8781 Tilghman Island Rd, Wittman, MD 21676
  • 22314 Pot Pie Rd, Wittman, MD 21676
    22314 Pot Pie Rd, Wittman, MD 21676
    22314 Pot Pie Rd, Wittman, MD 21676
    /14

    $295,000

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

    22314 Pot Pie Rd, Wittman, MD 21676

    Rental Opportunity in Wittman, MD Positioned in the desirable community of Wittman, this 3 bedroom, 2 bath home situated on 0.84± commercially zoned acreage and premier road frontage 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,

    Shawn Moore Meredith Fine Properties

    22314 Pot Pie Rd, Wittman, MD 21676
Maryland Talbot County Sherwood

Homes for Sale with Garage in Sherwood, MD

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In Sherwood, there are currently 27 homes for sale with a garage. Meeting the needs of buyers seeking secure parking and extra storage, these homes offer various garage options. Whether it's a property featuring a practical two-car garage or a larger residence with a sought-after three-car garage, these homes provide the convenience and flexibility desired by many homeowners. Additionally, some properties come with detached garages, offering ample space while ensuring privacy. Explore the selection of homes for sale with a garage in Sherwood, MD and find the perfect place to call home.

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