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Talbot County MD Homes for Sale with Basement

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  • /44

    $1,080,000

    • 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
  • /81

    $2,200,000 Open Sat 11:30AM - 1:30PM

    • 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
  • /7

    $1,250,000

    • 3 Beds
    • 1 Bath
    • 1,248 Sq Ft

    5850 Irish Creek Rd, Royal Oak, MD 21662

    Nestled on scenic Haskins Cove with direct access to Irish Creek and beyond, this charming 3-bedroom, 1-bath split-level home offers private waterfront living. Featuring gleaming hardwood floors on the main level, the home opens to an elevated deck with sweeping views of the tranquil water—ideal for relaxing or entertaining. A private pier provides easy access for boating, fishing, or simply

    Chuck Mangold Benson & Mangold, LLC

    5850 Irish Creek Rd, Royal Oak, MD 21662
  • /77

    $1,395,000

    • 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
  • /109

    $3,495,000

    • 4 Beds
    • 5 Baths
    • 5,207 Sq Ft

    26090 Royal Oak Rd, Easton, MD 21601

    This rare, historic, waterfront, Victorian estate combines privacy, nature, tranquility & excellent village location on Oak Creek in Royal Oak between St. Michaels & Easton. The treelined drive welcomes you to this one of a kind home built in 1890 and situated on 11.59 acres. Featuring stained glass transoms, the original staircase, heart pine wood floors, 10 foot ceilings, oversize windows,

    Kate Koeppen Chesapeake Bay Real Estate Plus, LLC

    26090 Royal Oak Rd, Easton, MD 21601
  • /68

    $3,350,000

    • 3 Beds
    • 3.5 Baths
    • 3,696 Sq Ft

    26333 Presquile Dr S, Easton, MD 21601

    Custom Contemporary on Wye River with Captivating Sunset Views. This solid one-story 3,700+/- sq ft brick rancher has been tastefully updated. Home sits on 5+/- acres and features high ceilings, Brazilian Cherry flooring, open floor plan with large kitchen with island, vaulted ceilings in the family room with fireplace, separate dining, sunroom, office/den/extra bedroom space, waterside primary

    Brian Gearhart Benson & Mangold, LLC

    26333 Presquile Dr S, Easton, MD 21601
  • /85

    $3,250,000

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

    7421 Quaker Neck Rd, Bozman, MD 21612

    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 experience with 4,352 square feet of main living space plus an additional 1,500

    Barbara McCaffrey Redfin Corp

    7421 Quaker Neck Rd, Bozman, MD 21612
  • /44

    $1,950,000

    • 3 Beds
    • 4 Baths
    • 2,568 Sq Ft

    6119 Country Club Dr, Easton, MD 21601

    Location, Location, Location!!! This recently renovated waterfront rancher on a 2+ acre, park-like lot is conveniently located next to Talbot Country Club, and off the Oxford Road corridor. This home features 3 bedrooms, 2 full and 2 - 1/2 baths, a large living room with fireplace, kitchen/family room combo with the kitchen featuring quartz counter tops, stainless steel appliances and custom

    Brian Gearhart Benson & Mangold, LLC

    6119 Country Club Dr, Easton, MD 21601
  • /75

    $1,350,000

    • 4 Beds
    • 4 Baths
    • 2,535 Sq Ft

    1026 Riverview Terrace, Saint Michaels, MD 21663

    Experience luxury living in this newly renovated coastal-style home in St. Michaels. Situated on a double lot, this is an exceptional and rare offering, combining water views and water access with a high quality home, redone with incredible attention to detail and livability. The exterior is tastefully appointed with painted brick and shingle-style siding, and an inviting covered front porch

    Carolina Barksdale Benson & Mangold, LLC

    1026 Riverview Terrace, Saint Michaels, MD 21663
  • /30

    $995,000

    • 3 Beds
    • 2.5 Baths
    • 2,324 Sq Ft

    219 S Harrison St, Easton, MD 21601

    Step into timeless elegance with this beautifully maintained 1900s home nestled in the heart of historic downtown Easton. Offering 3 bedrooms and 2.5 bathrooms, this residence seamlessly blends classic charm with modern comfort. Drenched in natural light, the inviting interior boasts a formal dining room, a cozy living room with a fireplace, and a spacious family room just off the kitchen. The

    Chuck Mangold Benson & Mangold, LLC

    219 S Harrison St, Easton, MD 21601
  • /39

    $675,000

    • 3 Beds
    • 2 Baths
    • 1,824 Sq Ft

    109 W Chew Ave, Saint Michaels, MD 21663

    Located in a prime location this 3-bedroom home is full of potential. Featuring a spacious yard, detached garage/workshop, and a breezy screened porch, it’s ready for your vision. Inside, you’ll find hardwood flooring, a beautiful formal dining room, den / office at the rear, and a eat-in kitchen with character-rich beamed ceilings. The second floor offers a large primary bedroom with private

    Barbara Watkins Benson & Mangold, LLC

    109 W Chew Ave, Saint Michaels, MD 21663
  • /38

    $565,000

    • 6 Beds
    • 3.5 Baths
    • 3,593 Sq Ft

    7080 Blackberry Ct, Easton, MD 21601

    Welcome to this spacious 3,852 sq ft home — a perfect blend of style, function, and endless possibilities! This 6-bedroom, 3.5-bath residence is packed with updates, including a brand-new roof (2023) and new HVAC system (2021), ensuring comfort and peace of mind for years to come.Inside, large windows flood the home with natural light, creating an inviting atmosphere throughout the main living

    Heather Brummell Shore Living Real Estate

    7080 Blackberry Ct, Easton, MD 21601
  • /69

    $615,000

    • 3 Beds
    • 2.5 Baths
    • 2,000 Sq Ft

    709 Elwood Ave, Easton, MD 21601

    Welcome to 709 Elwood Avenue — a meticulously maintained, solid brick home offering one-level living and a prime Easton location just moments from downtown, Idlewild Park, Rails-to-Trails, and more. Thoughtfully updated in 2015 and lovingly cared for ever since, this property blends classic charm with modern comforts, creating a rare opportunity for move-in ready living in one of Easton's most

    Julie Stevenson Shore Living Real Estate

    709 Elwood Ave, Easton, MD 21601
  • /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
  • /29

    $474,900

    • 4 Beds
    • 3.5 Baths
    • 2,036 Sq Ft

    202 Tubman Dr, Easton, MD 21601

    Beautifully maintained 4 bedroom, 3.5 bath home minutes to downtown Easton offering a rear two tiered deck, formal living and dining rooms, family room w/ wood floors, and open kitchen with island , newer built-in microwave, dishwasher, range, frig, and granite counters. Mostly finished basement has a full bath w/shower-tub. Laundry room (w/newer W/D) on 2nd floor where bedrooms and primary

    Craig Linthicum Benson & Mangold, LLC

    202 Tubman Dr, Easton, MD 21601
  • /71

    $599,000

    • 4 Beds
    • 4 Baths
    • 3,594 Sq Ft

    8658 Camac St, Easton, MD 21601

    Immaculate 4 Br 4 Ba 3600 + sq ft house in the desirable Hunter's Mill Community. The main level features a private in-law suite with full bath, ideal for guests or multigenerational living. The adjoining dining and living areas are filled with natural light and offer serene views of surrounding greenery. Upstairs, the primary suite includes a walk-in closet and access to a large attic space for

    Henry Gibbons-Neff Meredith Fine Properties

    8658 Camac St, Easton, MD 21601
  • /56

    $495,000

    • 3 Beds
    • 2 Baths
    • 2,288 Sq Ft

    8635 Brenton Dr, Easton, MD 21601

    Beautifully Updated 3 Bedroom, 2 Bath Home with Private Backyard Oasis in Easton!Welcome to your dream home! This stunning 3 bedroom, 2 bath residence offers the perfect blend of comfort, style and functionality. Situated on a nicely landscaped lot, the fully fenced in backyard is your own private oasis, complete with an in ground 18 x 36 saltwater pool, perfect for summer relaxation and

    Darlene Wheatley Benson & Mangold, LLC

    8635 Brenton Dr, Easton, MD 21601
  • /35

    $549,000

    • 3 Beds
    • 2 Baths
    • 1,674 Sq Ft

    400 Railroad Ave, Saint Michaels, MD 21663

    Nestled on a desirable corner lot in the historic waterfront town of St. Michaels, this 1930 bungalow blends classic architecture with modern comforts. Ideally located just a short distance from the Chesapeake Bay Maritime Museum, shops, restaurants, and the harbor, this home offers the best of in-town living. A spacious front porch welcomes you - perfect for morning coffee or casual

    Monica Penwell TTR Sotheby's International Realty

    400 Railroad Ave, Saint Michaels, MD 21663
  • /42

    $514,900

    • 4 Beds
    • 2.5 Baths
    • 2,540 Sq Ft

    29688 Tallulah Ln, Easton, MD 21601

    REDUCED! Sellers have found home of choice and want this sold! This lovely THREE level home has a total of almost 1000 more square ft. than the most recent sale in the community! Kick back and relax by the pool as the current owners have taken care of every other detail! New paint, flooring, window treatments and bathrooms in the last couple of months. Roof, tankless gas water heater,

    Mary Wagner Cummings & Co. Realtors

    29688 Tallulah Ln, Easton, MD 21601
  • /51

    $659,000

    • 3 Beds
    • 2 Baths
    • 1,660 Sq Ft

    901 S Talbot St, Saint Michaels, MD 21663

    St. Michaels English style Cottage – This Adorable 3-bedroom 2 bath home offers a first-floor primary bedroom, updated kitchen and baths, formal dining room, rear sunroom, and a fenced side and rear patio thoughtfully landscaped. The yard is irrigated. Long sweeping gables and roof peaks, prominent front facing chimney and entrance vestibule standout as architectural features of this 1930’s

    Barbara Watkins Benson & Mangold, LLC

    901 S Talbot St, Saint Michaels, MD 21663
  • /106

    $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
  • /88

    $2,950,000

    • 5 Beds
    • 4 Baths
    • 5,022 Sq Ft

    6549 Locust Grove Rd, Easton, MD 21601

    Discover the ultimate Eastern Shore retreat in the prestigious Baileys Neck community, just moments from Talbot Country Club. This exceptional waterfront estate sits on 5+ acres, offering breathtaking views of the river and a lifestyle of luxury and privacy. Recently renovated with the addition of a primary bedroom wing in 2019 and a brand new roof May 2025 . The main residence features 5

    Barbara Watkins Benson & Mangold, LLC

    6549 Locust Grove Rd, Easton, MD 21601
  • /44

    $2,650,000

    • 4 Beds
    • 5.5 Baths
    • 5,056 Sq Ft

    100 Beech Place, Easton, MD 21601

    Discover timeless elegance and refined living at Villa d’Avoncoeur, a striking 1925 landmark beautifully situated on a half-acre corner lot in the heart of downtown Easton. This fully renovated 5,056 sq ft residence offers 4–5 spacious bedrooms and 5.5 luxurious baths, blending historic charm with contemporary sophistication.From the moment you arrive, the home captivates with impeccable curb

    Laura Carney TTR Sotheby's International Realty

    100 Beech Place, Easton, MD 21601
  • /43

    $374,000

    • 2 Beds
    • 2 Baths
    • 1,222 Sq Ft

    8858 Howeth Rd, Wittman, MD 21676

    Welcome to this delightful cottage nestled in the historic village of Wittman. Situated on a charming corner lot, this home has been thoughtfully updated while preserving its historic character. The second level boasts a private en-suite primary bedroom, complete with a cozy nook ideal for a home office. On the main level, you’ll find a second bedroom, a versatile den or craft room with built-in

    Monica Penwell TTR Sotheby's International Realty

    8858 Howeth Rd, Wittman, MD 21676
  • /67

    $1,998,000

    • 4 Beds
    • 3 Baths
    • 2,628 Sq Ft

    7705 Quaker Neck Rd, Bozman, MD 21612

    This architecturally charming waterfront home sits on 5.6-acres of well-elevated land that offers an exceptional secluded setting and panoramic, wide views of Broad Creek. Located just minutes from Historic St. Michaels, this lovely home was thoughtfully expanded by the Easton architectural firm, Atelier 11 in a way that honors its distinctive New England “Bow House” architectural style while

    Eugene Smith TTR Sotheby's International Realty

    7705 Quaker Neck Rd, Bozman, MD 21612
  • /50

    $6,500,000

    • 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 baths,

    Laura Carney TTR Sotheby's International Realty

    11977 Billys Point Ln, Easton, MD 21601
  • /32

    $745,000

    • 3 Beds
    • 2 Baths
    • 1,440 Sq Ft

    27232 Hayward Trail, Easton, MD 21601

    First time offered in 50 years! Discover this hidden gem nestled along 200' of waterfrontage on Hayward Cove, opening onto the scenic Miles River. Located on at the end of the street, between Easton and St. Michaels this colonial style home is situated on a 1+ acre lot with mature trees, offering three bedrooms, two bathrooms, beautiful wood flooring, a cozy dining area accentuated by a free

    Barbara Watkins Benson & Mangold, LLC

    27232 Hayward Trail, Easton, MD 21601
  • /63

    $799,000

    • 4 Beds
    • 3.5 Baths
    • 2,737 Sq Ft

    8885 High Banks Dr, Easton, MD 21601

    This perfect three-level home offers breathtaking, unobstructed views of the majestic Choptank River. Designed to maximize its stunning setting, the main living areas are thoughtfully positioned to capture the serene water vistas, providing a tranquil backdrop for daily life. The heart of the home features an updated and remodeled kitchen, seamlessly flowing into open living spaces that are

    Connie Loveland Benson & Mangold, LLC

    8885 High Banks Dr, 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
  • /54

    $379,000

    • 6 Beds
    • 2.5 Baths
    • 3,448 Sq Ft

    4096 Main St, Trappe, MD 21673

    MAJOR PRICE IMPROVEMENT! First time offered for sale since its construction in 1918. Built by the Adams family, this Traditional Four Square with wrap around porch is a Trappe landmark. Conveniently located between Baltimore/DC and MD/DE beaches. Featuring 6 bedrooms and 2 1/2 bathrooms, there is plenty of room for a large family or possibly a Bed and Breakfast. A very well built home full of

    Andrew Beaven Wright Real Estate

    4096 Main St, Trappe, MD 21673
  • /30

    $495,000

    • 3 Beds
    • 3 Baths
    • 2,578 Sq Ft

    107 E Earle Ave, Easton, MD 21601

    Centrally located home near downtown, YMCA and the park. Two story with off street parking and a attached garage. Home has three bedrooms with the master on the first floor with bath. Large living room with fireplace, eat-in kitchen, enclosed porch and laundry room. This is an ideal home for buyers with a vision. Very nice yard and plantings. Home sits on a corner lot. Some of the back

    Mark Lappen Meredith Fine Properties

    107 E Earle Ave, Easton, MD 21601
  • /25

    $359,900

    • 3 Beds
    • 1.5 Baths
    • 2,268 Sq Ft

    7305 Frances St, Easton, MD 21601

    Spacious Stoney Ridge split foyer offering newer roof and HVAC. Offering 3 generous bedrooms with primary bath, open galley kitchen to spacious living and dining rooms. Kitchen leads to a composite rear deck with private, large fenced backyard. Full basement offering potential bonus/family room, utility room and workshop area and 1/2 bath. Property offers asphalt driveway, with potential room

    Bill Wieland Benson & Mangold, LLC

    7305 Frances St, Easton, MD 21601
  • /69

    $8,445,000

    • 4 Beds
    • 4.5 Baths
    • 9,117 Sq Ft

    5289 Ferry Neck Rd, Royal Oak, MD 21662

    This one of a kind property has it all-145 acres of farmland, pastures and farmland in sought after Royal Oak with a long view of Fox Hole Creek leading to the Tred Avon River. The stately paved driveway passes through the verdant landscape of broad vistas to three ponds, fields, pastures defined by white fences and a canopy of mature sawtooth oaks, until the Colonial style main house is

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    5289 Ferry Neck Rd, Royal Oak, MD 21662
  • /24

    $410,000

    • 3 Beds
    • 2.5 Baths
    • 3,456 Sq Ft

    29387 Stoney Ridge Cir, Easton, MD 21601

    This beautiful property is priced under appraised value which means immediate EQUITY for you AND the seller is offering $5000 in seller concessions which can be used toward rate buy-down, closing costs or property updates. Also, qualified borrowers are eligible for a $3000 grant from First Home Mortgage as well as both a reduced interest rate and reduced mortgage insurance. A MUST SEE! This

    Robin Gross Berkshire Hathaway HomeServices PenFed Realty

    29387 Stoney Ridge Cir, Easton, MD 21601
  • /52

    $679,950

    • 6 Beds
    • 3.5 Baths
    • 5,166 Sq Ft

    8677 Brenton Dr, Easton, MD 21601

    Don't miss this great opportunity to own this beautiful home located in "Mulberry Station" it has been completely remodel. The home features 6 bedroom, 3.5 bathrooms, numerous custom upgrades including new kitchen cabinets quartz counter tops, LVP flooring, it opens to great room and a separate dining room. There are 4 bedrooms located on the 2nd floor with a large primary bedroom with its own

    Daniel Foster Long & Foster Real Estate, Inc.

    8677 Brenton Dr, Easton, MD 21601
  • /20

    $329,000

    • 3 Beds
    • 2 Baths
    • 1,272 Sq Ft

    112 N Park St, Easton, MD 21601

    Beautiful, renovated colonial well appointed, large corner lot, 2 story garage/barn, small storage shed, features 3 bedrooms, (1 on entry level), 2 beds second floor, hardwood floors, stainless steel appliances, and large driveway for 6 car parking. Call for your private showing.

    Jana Meredith Meredith Fine Properties

    112 N Park St, Easton, MD 21601
  • /18

    $215,000

    • 3 Beds
    • 1.5 Baths
    • 1,584 Sq Ft

    13503 Main St, Queen Anne, MD 21657

    This is a fantastic opportunity for investors and home renovators: a handyman special. This property has 3 bedrooms and 1.5 bathrooms. Fenced-in yard with a shed. Off-street parking, a gravel driveway, a back deck and front porch. This 2-story has a lot of potential. The power is currently turned off. Well and septic exist. Being sold "As-IS".

    Peter Stark Benson & Mangold, LLC

    13503 Main St, Queen Anne, MD 21657
  • /23

    $562,500

    • 3 Beds
    • 2.5 Baths
    • 1,694 Sq Ft

    203 E Earle Ave, Easton, MD 21601

    A traditional home in the historic district w/ new roof and gutter, 2nd floor a/c, and window renovation. Great backyard w/patio and parking access from alley.

    Randy Staats Benson & Mangold, LLC

    203 E Earle Ave, Easton, MD 21601
  • /91

    $8,800,000

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

    27295 Southside Island Creek Rd, Trappe, MD 21673

    Wilderness Estate- This quintessential Eastern Shore farm is located along the Choptank River in Trappe, Maryland. Comprised of 47 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 farmland with proximity to Oxford, Easton,

    Coard Benson Benson & Mangold, LLC

    27295 Southside Island Creek Rd, Trappe, MD 21673
  • /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

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