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Talbot County MD Homes for Sale

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  • /2

    $525,000

    • 3 Beds
    • 2.5 Baths
    • 2,110 Sq Ft

    5582 Trafalgar Cir, Tilghman, MD 21671

    (More photos coming soon!) Welcome to 5582 Trafalgar Cir (truh-FAL-gar), a beautifully maintained single-level, 3-bedroom, 2.5-bath home located in the desirable Tilghman on Chesapeake community. Built in 2023 and offering 2,110 square feet of thoughtfully designed living space, this home has been lived in for only about a year and truly shows better than new. The seller’s meticulous care and

    BJ Kilby Eastern Shore Real Estate, LLC

    5582 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
  • /2

    $499,900 Open Sun 11AM - 1PM

    • 3 Beds
    • 3 Baths
    • 2,342 Sq Ft

    29709 Lyons Dr, Easton, MD 21601

    Lovely corner-lot home offering 2,342 square feet of thoughtfully designed living space. A welcoming entry showcases beautiful architectural details and sets the tone for this well-appointed residence. The separate dining room features an elegant tray ceiling, perfect for hosting gatherings.The bright and spacious kitchen includes an island, pantry, and ample room for a casual dining table.

    Jimmy White Long & Foster Real Estate, Inc.

    29709 Lyons Dr, Easton, MD 21601
  • /2

    $425,000 Open Fri 3PM - 5PM

    • 3 Beds
    • 2.5 Baths
    • 1,825 Sq Ft

    7144 Fir St, Easton, MD 21601

    Your beautifully updated 3 bed, 2.5 bath home awaits at the end of a private, tranquil cul-du-sac, conveniently located just minutes from Route 50, Easton's historic district, schools, shopping, restaurants and medical centers. Welcome to 7144 Fir Street, located in The Woods at Stoney Ridge. This traditional/colonial property offers tremendous curb appeal from the front and a private backyard

    Tiffany Cloud Meredith Fine Properties

    7144 Fir St, Easton, MD 21601
  • /130

    $11,000,000

    • 4 Beds
    • 5 Baths
    • 6,000 Sq Ft

    29245 Howell Point Rd, Trappe, MD 21673

    Presenting "Middleville" (est. 1880), one of the largest waterfront farm and residential estates currently available in the State of Maryland. Spanning over 662 pristine acres in Talbot County, this once-in-a-lifetime landholding features 1.8 miles of shoreline and a world-class infrastructure for luxury living and elite conservation. The Residences & Amenities: The centerpiece of the Estate is

    Jay Phillips Holiday Real Estate

    29245 Howell Point Rd, Trappe, MD 21673
  • /57

    $470,000

    • 3 Beds
    • 3 Baths
    • 1,800 Sq Ft

    9529 Quail Hollow Dr Unit 504, Saint Michaels, MD 21663

    Kate Koeppen Chesapeake Bay Real Estate Plus, LLC

    9529 Quail Hollow Dr Unit 504, Saint Michaels, MD 21663
  • /12

    $469,990 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,978 Sq Ft

    7853 Ward Brothers Cir, Easton, MD 21601

    Kitchen with quartz central island highlighted by matte black pendant lighting. Great room & dining area share a cohesive ceiling treatment. Concrete patio off the great room for easy outdoor living. Primary suite with ceiling treatment adds refined detail. Primary bath with dual sinks & glass shower enclosure. Second-floor loft offers flexible extra living space.

    K. Hovnanian Homes Builder
    7853 Ward Brothers Cir, Easton, MD 21601
  • /16

    $644,990 New Construction

    • 2 Beds
    • 2 Baths
    • 1,385 Sq Ft

    29403 Jobes St, Easton, MD 21601

    The Pacifica offers a thoughtfully designed open-concept layout infused with modern Elements design, with a projected settlement of January 2026. Featuring 2 bedrooms, 2 baths, and a 2-car garage, this home is ideal for comfortable, low-maintenance living. A screened patio extends the living space outdoors, creating the perfect spot to relax and unwind. Inside, luxury vinyl plank flooring

    Mary Anne Kowalewski KOVO Realty

    29403 Jobes St, Easton, MD 21601
  • /38

    $295,000

    • 2 Beds
    • 1.5 Baths
    • 1,248 Sq Ft

    29595 Dutchmans Ln Unit 42/701, Easton, MD 21601

    Come and visit this spacious Townhome in the Stoney Ridge Farm Community. This lovely 2 bedroom end unit townhome has been attractively renovated and is ready to be called “home”. Updates include new windows, new carpet, luxury plank flooring, a new half bath in the basement, recessed lighting, and fresh paint throughout. The kitchen features brand new cabinets, stainless steel appliances, and an

    Marla Baines Meredith Fine Properties

    29595 Dutchmans Ln Unit 42/701, Easton, MD 21601
  • /44

    $799,000

    • 4 Beds
    • 2 Baths
    • 1,724 Sq Ft

    22769 Almost Neavitt Rd, Bozman, MD 21612

    THE BEST EASTERN SHORE WATERFRONT VALUEWhere mornings begin by the water and plans tend to follow the tide, this Eastern Shore retreat blends relaxed waterfront living with thoughtful design by respected local architect Pam Gardener. Warm woods and a naturally flowing layout create easy and inviting view-filled spaces where you’ll prep picnics and gather for afternoons in. Comfortable for

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    22769 Almost Neavitt Rd, Bozman, MD 21612
  • /50

    $419,000

    • 4 Beds
    • 3.5 Baths
    • 2,786 Sq Ft

    29119 Superior Cir, Easton, MD 21601

    This updated end-unit townhome offers 4 bedrooms and 3 full baths with a spacious layout. The first-floor primary suite features a full bath and a walk-in closet, providing convenient main-level living. The kitchen boasts stainless steel appliances and opens to the main living area with a gas fireplace and first floor office.Upstairs are three generously sized bedrooms and a large loft ideal

    Alicia Gannon Dulin Benson & Mangold, LLC

    29119 Superior Cir, Easton, MD 21601
  • /41

    $824,900

    • 3 Beds
    • 3.5 Baths
    • 2,088 Sq Ft

    406 S Morris St, Oxford, MD 21654

    406 South Morris Street is a lovely home located in the Historic District of Oxford. She has 3 bedrooms each include en-suite bath. The layout of this home is smartly designed, and the owners describe it as “an easy home to love” and adore its location between Doc’s Sunset Grill, Pope's Tavern, the Scottish Highland Creamery, Town Park and the Pickle Ball Courts and more. In recent years they

    Will Stone Benson & Mangold, LLC

    406 S Morris St, Oxford, MD 21654
  • /78

    $699,900 Open Sat 10AM - 12PM

    • 4 Beds
    • 2.5 Baths
    • 2,220 Sq Ft

    13468 Rustling Oaks Dr, Wye Mills, MD 21679

    (Open House: Sat Jan 24th from 10-12) Welcome home to this Colonial located in the highly sought-after community of The Preserve at Wye Mills. Offering 2,220 square feet of finished living space plus an additional 1,140 sq ft unfinished basement, this home provides generous room to live, grow, and customize. The home features 4 spacious bedrooms, including an impressive primary suite with a

    Lona Todd Taylor Properties

    13468 Rustling Oaks Dr, Wye Mills, MD 21679
  • /55

    $597,500

    • 3 Beds
    • 1.5 Baths
    • 1,976 Sq Ft

    807 S Morris St, Oxford, MD 21654

    Charming Cape Cod on a corner lot in the heart of Oxford, Maryland’s Eastern Shore. This 3-bedroom, 1.5-bath home at 807 South Morris Street offers glimpses of the Tred Avon River from multiple rooms. Walk across the street to enjoy sunsets, sandy beach views, and peaceful water scenes from a nearby bench. The home features formal and informal living areas on the first floor, a spacious laundry

    Traci Jordan Meredith Fine Properties

    807 S Morris St, Oxford, MD 21654
  • /29

    $335,000

    • 4 Beds
    • 2.5 Baths
    • 2,002 Sq Ft

    305 Bethune Dr, Easton, MD 21601

    Welcome to this spacious end-unit townhouse offering 4 bedrooms and 2.5 bathrooms, providing plenty of room for comfortable living. The main level features a bright and open layout with abundant natural light, ideal for everyday living and entertaining. The kitchen opens to the main living areas, creating a functional and inviting space. Upstairs, you’ll find generously sized bedrooms, including

    Katie Moore Coldwell Banker Chesapeake Real Estate Company

    305 Bethune Dr, Easton, MD 21601
  • /16

    $450,000

    • 4 Beds
    • 2.5 Baths
    • 2,700 Sq Ft

    29141 Superior Cir, Easton, MD 21601

    Great location off Rt 50 in Lakelands in Easton, spacious 4br end unit with fully fenced backyard and open farmland views. 1st floor primary with full bath and large walk-in closet plus 3brs up, family room with gorgeous floors & gas fireplace, kitchen with granite tops & breakfast bar, den/office & spacious upstairs tv/playroom. 2 car garage and separate laundry with washer & dryer. Access to

    Janet Larson Benson & Mangold, LLC

    29141 Superior Cir, Easton, MD 21601
  • /55

    $3,250,000

    • 5 Beds
    • 5.5 Baths
    • 4,665 Sq Ft

    8515 Deep Cove Rd, Easton, MD 21601

    Beautifully sited on 17.7 acres along the Miles River in one of Easton’s most coveted locations, this quintessential coastal property embodies the essence of Eastern Shore living - casual elegance, timeless architecture, and a seamless connection to the water from nearly every vantage point. The 4,665 sq. ft. residence offers 4–5 bedrooms and 5.5 baths, with formal dining and living rooms, and a

    Laura Carney TTR Sotheby's International Realty

    8515 Deep Cove Rd, Easton, MD 21601
  • /20

    $435,000

    • 4 Beds
    • 2.5 Baths
    • 2,700 Sq Ft

    29181 Superior Cir, Easton, MD 21601

    Spacious four bedroom 2700+ fsf end unit town home in Easton's prized Lakelands subdivision 5 minutes from downtown and all its' amenities. New roof 2025, granite kitchen with stainless appliances,1st floor primary suite with private bath & large walk-in closet, living room w/fireplace, dining, area, powder room, 1st floor light filled den/office, two car garage and separate laundry with linen

    Janet Larson Benson & Mangold, LLC

    29181 Superior Cir, Easton, MD 21601
  • /2

    $18,900

    • Land
    • 0.17 Acre
    • $111,176 per Acre

    0 Newtown Village Rd, Cordova, MD 21625

    PROPERTY WAS BOUGHT AT TAX SALE, NO CURRENT PERC ON THE PROPERTY, VACANT LOT.

    Henry Gibbons-Neff Meredith Fine Properties

    0 Newtown Village Rd, Cordova, MD 21625
  • /8

    $5,350,000 New Construction

    • 4 Beds
    • 5.5 Baths
    • 6,184 Sq Ft

    0 Morgans Point Dr Unit MDTA2012638, Oxford, MD 21654

    Envisioned for a premier waterfront setting along the Tred Avon River, this exceptional TO-BE-BUILT coastal residence presents a rare opportunity to create a refined Eastern Shore retreat on a remarkable 4.18-acre homesite within the exclusive Morgan’s Point community of Oxford. Thoughtfully designed in classic shingle-style architecture, the proposed home is perfectly oriented to capture

    Agent Photo

    Gil Poudrier

    TTR Sotheby's International Realty

    (410) 883-9692

    0 Morgans Point Dr Unit MDTA2012638, Oxford, MD 21654
  • /42

    $524,995

    • 3 Beds
    • 2.5 Baths
    • 2,729 Sq Ft

    7371 Michael Ave, Easton, MD 21601

    Welcome to Easton Club East, one of the area's most sought-after 55+ communities. This beautifully cared-for Merion model, with 3 bedrooms, 2.5 baths, 2700+ sq.ft. of open living space, is situated on a premier lot backing to trees. The foyer sets a welcoming tone, leading into the formal dining area, sun-bathed sitting room, and the main living spaces. The two-story great room with fireplace

    Doc Keane Washington Fine Properties, LLC

    7371 Michael Ave, Easton, MD 21601
  • /3

    $49,900

    • Land
    • 1.28 Acres
    • $38,984 per Acre

    0 Ocean Gateway Unit MDTA2012696, Trappe, MD 21673

    1.28 Acres of vacant land on Route 50 Eastbound between Almshouse Road and Sanderstown Road. Undergrowth and small trees have been cleared and woodchips spread for easy access. Property does not have a SDA and therefore is not a buildable lot at this time. A 3 bedroom SDA application has been made for this 2026 wet season testing. Property will also need a driveway connection to Route 50 (an

    Holly Anderson Long & Foster Real Estate, Inc.

    0 Ocean Gateway Unit MDTA2012696, Trappe, MD 21673
  • /23

    $249,000

    • 3 Beds
    • 1 Bath
    • 1,240 Sq Ft

    305 Brookletts Ave, Easton, MD 21601

    GREAT CONVENIENT IN TOWN LOCATION FOR THE HANDY HOMEOWNER OR INVESTOR. LOTS OF POTENTIAL!INTERIOR NEEDS WORK, HARDIPLANK SIDING IS NEW. SPACIOUS LOT WITH BACK ALLEY ACCESS FOR PARKING . EASTON WALKING TRAIL IS JUST DOWN THE ROAD.EASY TO SHOW, APPRAISAL ON FILE.

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    305 Brookletts Ave, Easton, MD 21601
  • /55

    $505,000

    • 3 Beds
    • 3 Baths
    • 2,342 Sq Ft

    7344 Casey Ave, Easton, MD 21601

    Chesapeake By Del Webb. Popular 2 story Wittman model. Great room with gas fireplace, dining room, large eat-in kitchen with breakfast nook and center island, sunroom, office, 1st floor primary suite with walk-in closet and bath with walk-in shower and soaking tub, guest bedroom, hall bath and laundry. 2nd floor is perfect for guests with a loft, bedroom and bath. Features a 2 car rear loading

    Judy Moore Benson & Mangold, LLC

    7344 Casey Ave, Easton, MD 21601
  • /69

    $389,000 Pre-Foreclosure

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

    4096 Main St, Trappe, MD 21673

    Built in 1919 and offering approximately 3,448 square feet of living space, this stately farmhouse sits on a generous .44-acre lot and is filled with timeless architectural details and remarkable potential to be restored to its original beauty. A spacious front foyer welcomes you inside and offers the perfect place for a coat nook or shoe station, all while framing a stunning view of the home’s

    Donna Harrington Coldwell Banker Realty

    4096 Main St, Trappe, MD 21673
  • /45

    $695,000 Coming Soon

    • 4 Beds
    • 2.5 Baths
    • 3,886 Sq Ft

    1009 S Washington St, Easton, MD 21601

    Nestled in one of downtown Easton’s most coveted neighborhoods, this expansive four-bedroom residence offers an unparalleled blend of classic Eastern Shore charm and modern peace of mind. The location is truly unbeatable, placing you just a short stroll from the scenic trails of Idlewild Park, the YMCA, and the vibrant shopping and dining scene of historic downtown Easton. From the moment you

    Barbara Watkins Benson & Mangold, LLC

    1009 S Washington St, Easton, MD 21601
  • /32

    $315,000

    • 3 Beds
    • 1 Bath
    • 1,092 Sq Ft

    16 Willis Ave, Easton, MD 21601

    Charming 3-Bedroom Rancher in an Ideal Easton Location! Nestled in a prime Easton location, 16 Willis Avenue offers the perfect combination of comfort, convenience, and charm. This well-maintained 3-bedroom, 1-bath rancher is situated on a desirable corner lot, just a stone's throw from the heart of Easton. Whether you're looking for a great starter home or a cozy space to downsize, this property

    Jen Voshell Coldwell Banker Chesapeake Real Estate Company

    16 Willis Ave, Easton, MD 21601
  • /3

    $150,000

    • Land
    • 0.36 Acre
    • $416,667 per Acre

    220 W Dover St, Easton, MD 21601

    Rare land development opportunity in the heart of Easton’s Central Business District. This ±0.36 acre parcel is ideally positioned within the Town of Easton PUD infill area, offering a highly desirable location for a variety of potential development concepts, including a multi-unit structure (subject to Town approvals). The property benefits from close proximity to Easton’s renowned historic

    Shawn Moore Meredith Fine Properties

    220 W Dover St, Easton, MD 21601
  • /73

    $515,000

    • 3 Beds
    • 2.5 Baths
    • 3,052 Sq Ft

    29754 Hillary Ave, Easton, MD 21601

    Exceptional Home located in the desirable Easton Club East +55 Community. Three bedroom, Two-Story McDaniel Model boasts over 3,000 sqft. Welcoming Front Porch - with peaceful views. Large Foyer welcomes guests, including Formal Dining and Living Room. Expansive Family Room with two story ceilings, Custom Bookshelves surround Cozy Gas Fireplace. The bright Sunroom walks out to the outdoor Patio

    April Heim Rosendale Realty

    29754 Hillary Ave, Easton, MD 21601
  • /67

    $1,299,000

    • 3 Beds
    • 2.5 Baths
    • 2,840 Sq Ft

    7605 Pendleton Farm Ln, Easton, MD 21601

    Experience exceptional waterfront living in this custom-built home set on a private, 3-acre lot. Designed to maximize comfort and connection to the outdoors. The spacious floor plan includes a dedicated office, a cozy den and a gourmet kitchen. The oversized garage and separate laundry room are an added bonus to this perfect property. This custom designed and built - one of a kind home is

    Connie Loveland Benson & Mangold, LLC

    7605 Pendleton Farm Ln, Easton, MD 21601
  • /43

    $2,195,000

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

    22707 Marshall Ln, Wittman, MD 21676

    Exceptional custom waterfront home on Harris Creek offering an ideal setting for boating, kayaking, paddleboarding and relaxed days on the water. Perfectly suited for a discerning second-home buyer or full-time Eastern Shore living, this five-bedroom, three-and-a-half-bath residence blends thoughtful design with an effortless waterfront lifestyle. A dramatic two-story foyer welcomes you into

    Kathy Christensen TTR Sotheby's International Realty

    22707 Marshall Ln, Wittman, MD 21676
  • /34

    $420,000

    • 3 Beds
    • 2 Baths
    • 2,200 Sq Ft

    9116 Camelia Dr, Easton, MD 21601

    Beautifully updated, this stylish split-level residence blends thoughtful design with everyday comfort, offering a home that feels both welcoming and well cared for. Numerous upgrades can be found throughout, including updated light fixtures, crown molding, wainscoting, newer roof installed in 2025 with transferable warranty, a fully renovated kitchen, and many additional enhancements that

    Candis Williamson Northrop Realty

    9116 Camelia Dr, Easton, MD 21601
  • /69

    $769,999

    • 4 Beds
    • 2.5 Baths
    • 2,876 Sq Ft

    28241 Knapps Lot St, Easton, MD 21601

    Ideally located in the highly sought-after waterfront community of Easton Village, this beautifully maintained home offers nearly 3,000 square feet of refined living just minutes from downtown Easton, St. Michaels, and Oxford, and conveniently close to Easton Airport with jet service—perfect for those seeking an effortless Eastern Shore lifestyle. Set on a premier, oversized corner lot, the

    Eddie Mangold Benson & Mangold, LLC

    28241 Knapps Lot St, Easton, MD 21601
  • /2

    $350,000

    • 4 Beds
    • 3.5 Baths
    • 2,040 Sq Ft

    29487 Hemlock Ln, Easton, MD 21601

    Investor special! Home has had very little use and was mostly used as a storage unit over the last 6 years. Please contact listing agent with any questions you may have.

    Pasquale Carannante RE/Max Experience

    29487 Hemlock Ln, Easton, MD 21601
  • /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
  • /38

    $335,000

    • 4 Beds
    • 2.5 Baths
    • 1,916 Sq Ft

    505 Wheatley Dr, Easton, MD 21601

    Move-in ready, one-owner end-unit townhome built in 2022, proudly owner-occupied and meticulously maintained, located in the desirable Patriot Square community. This home offers 4 bedrooms and 2.5 bathrooms, with a primary suite and private bathroom on the main level, along with a convenient half bath—perfect for main-level living. The upper level features three additional bedrooms and one full

    Shay Prattis Keller Williams Realty

    505 Wheatley Dr, Easton, MD 21601
  • /7

    $475,000

    • 3 Beds
    • 2.5 Baths
    • 2,676 Sq Ft

    7364 Ocean Gateway, Easton, MD 21601

    Beautifully Updated Split-Level Retreat on Nearly an Acre Along Route 50! Set back on a private, wooded lot just under an acre, this beautifully remodeled 3-bedroom, 2.5-bath split-level home offers the perfect blend of comfort, style, and outdoor enjoyment. A long circular driveway welcomes you home, setting the tone for the peaceful setting that surrounds this 2,676 sq. ft. property. Inside,

    Stacie Luhrman Benson & Mangold, LLC

    7364 Ocean Gateway, Easton, MD 21601
  • /4

    $324,040 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,254 Sq Ft

    1221 Loch Ness Ln, Trappe, MD 21673

    Welcome to 1221 Loch Ness Lane, located in the desirable Lakeside at Trappe community. This Elmwood front-load garage townhome (Homesite #C467) offers 3 bedrooms, 2.5 baths, and 2,254 square feet of open-concept living designed for comfort and low-maintenance living. The home includes a 2-car front-load garage and an HOA of $85/month. The kitchen is thoughtfully designed with granite or quartz

    Shay Prattis Keller Williams Realty

    1221 Loch Ness Ln, Trappe, MD 21673
  • /47

    $389,000

    • 2 Beds
    • 2.5 Baths
    • 1,486 Sq Ft

    24700 Deepwater Point Dr Unit 1, Saint Michaels, MD 21663

    Inviting townhouse in the St. Michaels Martingham community with views across the Links at Perry Cabin fairway, offering easy Eastern Shore living. From the upstairs living areas, enjoy lovely, elevated views, abundant natural light, and a sense of openness that enhances the home’s warm, inviting feel. The upper-level living area features shining hardwood floors, and the home has been recently

    Agent Photo

    Maureen McHugh

    Chesapeake Bay Real Estate Plus, LLC

    (888) 352-1904

    24700 Deepwater Point Dr Unit 1, Saint Michaels, MD 21663
  • /3

    $250,000

    • Land
    • 2 Acres
    • $125,000 per Acre

    0 Black Dog Aly Unit MDTA2012546, Easton, MD 21601

    Quaint 2 +/- acre country lot in prime location close to downtown Easton. Perc has been approved for 3 bedrooms and was recently re-evaulated by the TCEHD.

    Alicia Gannon Dulin Benson & Mangold, LLC

    0 Black Dog Aly Unit MDTA2012546, Easton, MD 21601

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