25

Sherwood, MD Homes for Sale with Acreage

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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
  • 22101 Grafton Manour Ln, Wittman, MD 21676
    22101 Grafton Manour Ln, Wittman, MD 21676
    22101 Grafton Manour Ln, Wittman, MD 21676
    /133

    $7,800,000

    • 4 Beds
    • 4.5 Baths
    • 7,407 Sq Ft

    22101 Grafton Manour Ln, Wittman, MD 21676

    Grafton Manour Estate—A Rare Chesapeake Waterfront Legacy. Embrace the quiet grandeur of Grafton Manour Estate, an 86±-acre peninsula wrapped by approximately 1.5± miles of shoreline with panoramic water views in every direction. Bordered by Briary Cove to the east, Harris Creek to the southeast, and Waterhole Cove to the west, this extraordinary property blends pastoral elegance with true

    Agent Photo

    Tracy Higgs-Wagner

    Meredith Fine Properties

    22101 Grafton Manour Ln, Wittman, MD 21676
  • 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
  • 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
  • 0 Cooper Point Rd Unit MDTA2014078, Bozman, MD 21612
    0 Cooper Point Rd Unit MDTA2014078, Bozman, MD 21612
    0 Cooper Point Rd Unit MDTA2014078, Bozman, MD 21612
    /25

    $550,000

    • Land
    • 2.45 Acres
    • $224,490 per Acre

    0 Cooper Point Rd Unit MDTA2014078, Bozman, MD 21612

    Just 7 miles (10 -12 minute drive) outside historic St. Michaels, MD: Rare 2.44-acre waterfront building lot with 600' of stable shoreline along the waters of Grace Creek, a scenic tributary of Broad Creek. Outstanding sunrise views looking directly down the creek! Actually, this offering includes 2 separate lots of record....a 2-acre lot and a .4-acre lot. The larger parcel features higher

    Tom Crouch Benson & Mangold, LLC

    0 Cooper Point Rd Unit MDTA2014078, Bozman, MD 21612
  • 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
  • 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
  • 0 Quaker Neck Rd, Bozman, MD 21612
    0 Quaker Neck Rd, Bozman, MD 21612
    0 Quaker Neck Rd, Bozman, MD 21612
    /6

    $800,000

    • Land
    • 10.48 Acres
    • $76,336 per Acre

    0 Quaker Neck Rd, Bozman, MD 21612

    This exceptional 10.48 acre parcel of land offers a rare opportunity to embrace an exclusive lifestyle. With an impressive 461+/- feet of waterfront along the picturesque Sandy Point Cove leading to Broad Creek, this property is a haven for privacy. Enjoy private access to the water, ideal for fishing, canoeing, and kayaking. The expansive lot offers ample space for the creation of a luxurious

    Melissa Tippett TTR Sotheby's International Realty

    0 Quaker Neck 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
  • 9818 Tilghman Island Rd, McDaniel, MD 21647
    9818 Tilghman Island Rd, McDaniel, MD 21647
    9818 Tilghman Island Rd, McDaniel, MD 21647
    /38

    $449,900

    • 4 Beds
    • 2.5 Baths
    • 1,876 Sq Ft

    9818 Tilghman Island Rd, McDaniel, MD 21647

    The Perfect Blend of Space & Proximity. Loved by one family, this 4 bedroom 2 1/2 bath home is ready for the next owner. Situated on a beautiful1-acre parcel, this property is framed by magnificent, beautifully spaced mature trees and a cool gazebo to enjoy the park-like setting. Located in desirable McDaniel, you enjoy the ultimate Eastern Shore lifestyle: peaceful rural privacy, no HOA, and a

    Valerie Brown Coldwell Banker Realty

    9818 Tilghman Island Rd, McDaniel, MD 21647
  • 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
  • 21869 Albie Rd, Sherwood, MD 21665
    21869 Albie Rd, Sherwood, MD 21665
    21869 Albie Rd, Sherwood, MD 21665
    /39

    $519,000

    $56K PRICE DROP
    • 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
  • 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
  • 8000 Bozman Neavitt Rd, Bozman, MD 21612
    8000 Bozman Neavitt Rd, Bozman, MD 21612
    8000 Bozman Neavitt Rd, Bozman, MD 21612
    /57

    $499,000

    $91K PRICE DROP
    • 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
  • 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

    • 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
  • 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
  • 21721 Heavenly Haven Rd, Sherwood, MD 21665
    21721 Heavenly Haven Rd, Sherwood, MD 21665
    21721 Heavenly Haven Rd, Sherwood, MD 21665
    /149

    $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
Maryland Talbot County Sherwood

Homes for Sale with Acreage in Sherwood, MD

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In Sherwood, there are currently 25 homes for sale with acreage, providing ample space for homeowners to customize their living environment, whether for expansive gardens, outdoor entertaining, or enhanced privacy. Whether you're in search of a spacious family home with plenty of room to roam, a property ripe for development, or simply seeking space and tranquility, homes for sale with acreage in Sherwood, MD offer the flexibility to tailor your living experience to your preferences. Browse the selection of homes for sale with land in Sherwood and discover the potential and freedom that comes with owning your own piece of property.

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