368

Talbot County MD Homes for Sale

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  • /45

    $795,000

    • 4 Beds
    • 4 Baths
    • 2,900 Sq Ft

    28713 Emanuel St, Easton, MD 21601

    This two-story Charleston-style Colonial is located in the desirable Cooke’s Hope Village community and sits on an oversized lot with a fenced side and rear yard. The property includes a spacious entry-level side porch, second-level balcony, lush seasonal gardens, and a private fenced brick courtyard with built-in speakers for music and a retractable awning—perfect for outdoor entertaining.

    Chuck Mangold Benson & Mangold, LLC

    28713 Emanuel St, Easton, MD 21601
  • /2

    $425,000

    • 4 Beds
    • 2.5 Baths
    • 2,112 Sq Ft

    8804 Roundhouse Cir, Easton, MD 21601

    Welcome to an exceptional opportunity to own a home in the highly sought‐after Mulberry Station community. This spacious 4‐bedroom, 2.5‐bath residence offers one of the neighborhood’s most desirable floor plans, set on nearly a half‐acre—one of the largest lots in the community—and backing to peaceful open farmland for added privacy and views. Inside, the home features a welcoming flow with a

    Stacie Luhrman Benson & Mangold, LLC

    8804 Roundhouse Cir, Easton, MD 21601
  • /40

    $499,990

    New Construction
    • 3 Beds
    • 3 Baths
    • 2,401 Sq Ft

    8699 Harper Way, Easton, MD 21601

    Discover the charm of 8699 Harper Way, a new home in Gannon Range, ideally located minutes away from downtown Easton, MD, boasting serene surroundings and convenient proximity to Route 50. This 2,401 square foot, open concept two-story home offers three bedrooms, including a first-floor primary, a flex room, three full bathrooms, 9’ ceilings, a loft, and a two-car garage. A welcoming foyer leads

    D.R. Horton Builder
    8699 Harper Way, Easton, MD 21601
  • /79

    $1,450,000

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

    208 Factory St, Oxford, MD 21654

    Beyond the white picket fence, a storybook garden unfolds—lush, curated, and unmistakably Oxford. Perfectly positioned just moments from the beach, ferry, and waterfront park, 208 Factory Street offers a rare blend of timeless village charm and sophisticated modern comfort. Thoughtfully enhanced with updated mechanical systems since 2019, this three-bedroom residence has been meticulously

    Chuck Mangold Benson & Mangold, LLC

    208 Factory St, Oxford, MD 21654
  • /29

    $569,000

    • 3 Beds
    • 2.5 Baths
    • 2,739 Sq Ft

    29825 Hillary Ave, Easton, MD 21601

    Easy Eastern Shore living in the highly sought-after 55+ section of Easton Club East! This beautifully maintained and updated home features formal living and dining rooms, a spacious family room with gas fireplace and a sunroom overlooking the beautifully landscaped rear yard and pond. The custom remodeled kitchen features Cambria quartz countertops, custom cabinetry, GE Advantium appliances and

    Barbara Watkins Benson & Mangold, LLC

    29825 Hillary Ave, Easton, MD 21601
  • /72

    $2,795,000

    • 4 Beds
    • 3.5 Baths
    • 3,500 Sq Ft

    200 West St, Oxford, MD 21654

    Perfectly positioned along the prestigious shores of the Tred Avon River, this extraordinary waterfront estate offers breathtaking water views from nearly every room and an unparalleled blend of luxury, craftsmanship, and cutting-edge sustainability.Designed to embrace its spectacular setting, the three-level main residence features exceptional attention to detail throughout, including rich

    Chuck Mangold Benson & Mangold, LLC

    200 West St, Oxford, MD 21654
  • /43

    $630,000

    Open Sun 11AM - 1PM
    • 4 Beds
    • 2.5 Baths
    • 2,841 Sq Ft

    9206 Martingham Dr, Saint Michaels, MD 21663

    NEW PRICE — EXCEPTIONAL VALUE IN DESIRABLE MARTINGHAM!Welcome to 9206 Martingham Drive, a truly distinctive contemporary residence offering spacious living, abundant natural light, and timeless architectural character in one of Saint Michaels' most sought-after communities. Competitively priced and thoughtfully designed, this unique home features an open floor plan, soaring vaulted ceilings,

    Salar Hakimi Samson Properties

    9206 Martingham Dr, Saint Michaels, MD 21663
  • /32

    $449,000

    • 4 Beds
    • 2.5 Baths
    • 1,508 Sq Ft

    312 Spring Dr, Easton, MD 21601

    NEW LISTING! Perfectly situated on a cul-de-sac in Charlestown Village, one of downtown Easton’s most desirable neighborhoods, this four‐bedroom home offers an inviting blend of comfort and style. The open floor plan flows seamlessly from the kitchen to the dining area and into the living room. A broad, covered mahogany front porch provides the perfect spot to relax, while the large rear deck is

    Janet Larson Benson & Mangold, LLC

    312 Spring Dr, Easton, MD 21601
  • /4

    $1,595,000

    • 4 Beds
    • 3 Baths
    • 2,852 Sq Ft

    28674 Edgemere Rd, Easton, MD 21601

    If you are one who expects the unexpected, this waterfront property in Easton will not disappoint. From the one-hundred-year-old oak standing sentinel over Peachblossom Creek to the 42 solar panels creating minimal power bills, this “issue free” home is unexpected, if not actually startling. Ideally located along the desirable Oxford Road corridor, the property offers convenient access to both

    Barbara Watkins Benson & Mangold, LLC

    28674 Edgemere Rd, Easton, MD 21601
  • /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
  • /25

    $350,000

    • 3 Beds
    • 1 Bath
    • 1,262 Sq Ft

    21647 Camper Cir, Tilghman, MD 21671

    Welcome to 21647 Camper Circle in the charming waterfront community of Tilghman Island. This well-maintained home offers a peaceful Eastern Shore lifestyle with easy access to boating, fishing, crabbing, local marinas, and waterfront dining. Enjoy the relaxed island atmosphere while still being just a short drive from historic St. Michaels and other nearby amenities. The property features

    Heather Brummell Keller Williams Realty

    21647 Camper Cir, Tilghman, MD 21671
  • /37

    $499,000

    • 3 Beds
    • 3 Baths
    • 2,414 Sq Ft

    28542 Congressional Ct, Easton, MD 21601

    Beautiful end-unit townhome in desirable Easton Club, offering a rare combination of natural light, flexible living space, and sweeping, peaceful nature views. Thoughtfully positioned on one of the larger lots among the original Easton Club townhomes, this home features added side windows that bring in wonderful natural light while capturing the surrounding nature views. The main level offers an

    Laura Anderson Coldwell Banker Realty

    28542 Congressional Ct, Easton, MD 21601
  • /14

    $629,990

    New Construction $40K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 2,493 Sq Ft

    29405 Jobes St, Easton, MD 21601

    Home office with sliding doors off the foyer.Great room & dining area connect by striking vaulted ceiling.Elegant fireplace with hearth adds charm to the great room.Kitchen with Ash Grey cabinetry & pendant lights.Screened patio extends living space outdoors.Primary suite & private bath with dual freestanding vanities.Attached 3-car garage for added storage & parking.

    K. Hovnanian Homes Builder
    29405 Jobes St, Easton, MD 21601
  • /34

    $589,990

    New Construction $70K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,772 Sq Ft

    29339 Blackiston St, Easton, MD 21601

    Beautiful kitchen with Chestnut Brown cabinetry & quartz countertops.Inviting great room featuring cozy fireplace & stained ceiling beams.Serene primary suite with stylish feature wall.Refreshing primary bath with dual vanities & matte black finishes.Private Extra Suite for overnight guests.Functional laundry room with washer & dryer included.Peaceful screened patio for

    K. Hovnanian Homes Builder
    29339 Blackiston St, Easton, MD 21601
  • /28

    $669,990

    New Construction $50K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 2,963 Sq Ft

    29401 Jobes St, Easton, MD 21601

    Elegant kitchen with Pewter Grey cabinetry & center island.Open concept living areas featuring cozy fireplace & vaulted ceiling.Lavish primary suite & bath with generous walk-in closet.Secluded home office, perfect for working remotely.Functional laundry room with washer & dryer included.Peaceful screened patio for relaxing with friends.Attached 2-car garage with

    K. Hovnanian Homes Builder
    29401 Jobes St, Easton, MD 21601
  • /35

    $425,000

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

    29152 Holly Rd, Easton, MD 21601

    Welcome to this spacious Cape Cod home featuring three bedrooms and two and a half bathrooms. Enjoy a welcoming front porch, an attached garage, and a generous yard perfect for outdoor enjoyment. A rear porch provides opportunity for outdoor dining and evening relaxation. Inside, the great room impresses with vaulted ceilings, and the primary bathroom offers a Jacuzzi tub and separate shower.

    Henry Hale Benson & Mangold, LLC

    29152 Holly Rd, Easton, MD 21601
  • /68

    $410,000

    • 4 Beds
    • 2.5 Baths
    • 1,920 Sq Ft

    21406 Dogwood Cove Rd, Tilghman, MD 21671

    Experience authentic Eastern Shore living in this peaceful Chesapeake Bay retreat, located just steps from historic Dogwood Harbour, home to the Skipjacks—the last working commercial sailing fleet in the United States. This charming home features three first-floor bedrooms and a full bath, providing comfortable one-level living for family and guests. The remodeled eat-in kitchen showcases granite

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    (667) 446-1685

    21406 Dogwood Cove Rd, Tilghman, MD 21671
  • /55

    $925,000

    Coming Soon
    • 3 Beds
    • 2 Baths
    • 1,780 Sq Ft

    228 South St, Oxford, MD 21654

    The Rose Cottage was first built in 1890 and owned by a waterman. With barely 1,200 square feet, the house served many generations of Oxford families. Fast forward for about 100 years, the house was raised and the foundation was modernized in the late 1990s. With plumbing and electrical upgrades, the house became a modern historical home. When the current owners bought the Cottage in 2004, they

    Henry Hale Benson & Mangold, LLC

    228 South St, Oxford, MD 21654
  • /3

    $575,000

    Coming Soon
    • 3 Beds
    • 2 Baths
    • 1,352 Sq Ft

    225 Tyler Ave, Saint Michaels, MD 21663

    Nestled beneath a cathedral of mature trees in sought-after Rio Vista, this beautifully updated home offers the perfect blend of privacy, convenience, and future potential. Extensively renovated between 2020 and 2024, the home features a well-appointed kitchen, spacious living areas, and a stunning screened porch that creates inviting spaces for everyday living and entertaining. The wooded

    Maureen McHugh Chesapeake Bay Real Estate Plus, LLC

    225 Tyler Ave, Saint Michaels, MD 21663
  • /2

    $1,995,000

    Coming Soon
    • 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
  • /2

    $160,000

    • Land
    • 3,920 Sq Ft
    • $1,777,778 per Acre

    20 S Aurora St, Easton, MD 21601

    Lot has been approved by the Historic commission and exterior plans available , Easton Board of zoning appeal is approved for Variances to lot lines setback and approved for Duplex of up to 1200 feet per unit .Off street parking approved by BOZA for two cars.. Lane Engineering approved drawings available...Easton Utilities has approved all services to lot......Sidewalks and curb already completed

    Zebulon Stafford Stafford-Stafford Real Estate

    20 S Aurora St, Easton, MD 21601
  • /47

    $540,000

    • 3 Beds
    • 3 Baths
    • 3,506 Sq Ft

    7316 Casey Ave, Easton, MD 21601

    Hillsboro model in the desirable Easton Club East Community. Corner lot! Over 3000sqft with a thoughtful floor plan. The first floor boasts 2 bedrooms and 2 bathrooms, an office/library, family room off of the eat in kitchen, living and dining room and laundry room. Upstairs is a large loft area with a 3rd bedroom and bathroom. New HVAC in 2022, New roof in 2023.

    Agent Photo

    Elizabeth Tryon

    Coldwell Banker Realty

    (410) 431-0963

    7316 Casey Ave, Easton, MD 21601
  • /68

    $995,000

    • 3 Beds
    • 2.5 Baths
    • 2,016 Sq Ft

    8684 Sewell Point Rd, Wittman, MD 21676

    Affordable Talbot County, MD waterfront home. Just a 12-minute drive beyond St. Michaels, this well-built 3 bedroom, 2.5 bath home faces west across the waters of Cummings Creek. Great sunset views from the waterside screened porch! The 1.92-acre lot is well-elevated (flood insurance is not required by mortgage lenders). The house features generous-sized rooms, including a spacious kitchen/dining

    Tom Crouch Benson & Mangold, LLC

    8684 Sewell Point Rd, Wittman, MD 21676
  • /27

    $565,000

    • 3 Beds
    • 1 Bath
    • 1,873 Sq Ft

    6026 Ocean Gateway, Trappe, MD 21673

    Some properties sell a lifestyle. This one sells a legacy. Positioned on 10.7 acres along Route 50 in Talbot County with A2 zoning, this is one of the Eastern Shore's most compelling land opportunities for the entrepreneur or farmer ready to build something that lasts. Permitted uses by right include farm market, winery, cidery, distillery, aquaculture, and commercial storage. Special exception

    Sandra Bradley Keller Williams Select Realtors of Easton

    6026 Ocean Gateway, Trappe, MD 21673
  • /8

    $975,000

    $80K PRICE INCREASE Coming Soon
    • 4 Beds
    • 3 Baths
    • 2,850 Sq Ft

    4938 Fairbank Rd, Tilghman, MD 21671

    Tucked away in the charming Fairbank community on Tilghman Island, this delightful waterfront home captures the very best of Eastern Shore living. Overlooking the serene waters of Blackwalnut Cove with approximately 3’ MLW, the property blends classic cottage character with thoughtful modern enhancements. The original portion of the home reflects its roots as a cozy summer cottage, complete with

    Agent Photo

    Tracy Higgs-Wagner

    Meredith Fine Properties

    (667) 282-1801

    4938 Fairbank Rd, Tilghman, MD 21671
  • /2

    $325,000

    Coming Soon
    • 2 Beds
    • 1 Bath
    • 1,302 Sq Ft

    347 N Washington St, Easton, MD 21601

    Charming, updated Cape Cod just minutes walking distance from downtown Easton! Enjoy beautiful hardwood floors, a bright kitchen, and a spacious second floor featuring a large bedroom, office area, walk-in closet, and abundant storage. Relax on the welcoming front porch with swing, or enjoy the large, landscaped backyard with new deck and patio and a large storage shed with rear access too. New

    Pamela Devlin Long & Foster Real Estate, Inc.

    347 N Washington St, Easton, MD 21601
  • /4

    $814,990

    New Construction Coming Soon
    • 4 Beds
    • 4.5 Baths
    • 3,736 Sq Ft

    0000 Rustling Oaks Dr, Wye Mills, MD 21679

    The Brentwood: True Executive-Style Luxury on the Eastern ShoreExperience unparalleled scale and sophisticated design in the Brentwood, a magnificent 3,736-square-foot executive residence designed for modern luxury living. Set within a premier community featuring expansive, large home sites, this estate offers a rare and highly coveted feature for the Eastern Shore: a massive, full unfinished

    Mike Boryk Koch Realty, Inc.

    0000 Rustling Oaks Dr, Wye Mills, MD 21679
  • /64

    $1,300,000

    • 3 Beds
    • 2.5 Baths
    • 1,836 Sq Ft

    344 Perry Cabin Dr, Saint Michaels, MD 21663

    Maureen McHugh Chesapeake Bay Real Estate Plus, LLC

    344 Perry Cabin Dr, Saint Michaels, MD 21663
  • /72

    $574,999

    • 2 Beds
    • 1 Bath
    • 1,200 Sq Ft

    204 E Marengo St, Saint Michaels, MD 21663

    The perfect weekend getaway does exist—and it's more attainable than you might think. Escape the city and discover the charm of St. Michaels, one of the Eastern Shore's most beloved waterfront towns. Known for its picturesque streets, waterfront dining, boutique shopping, wineries, marinas, and laid-back coastal lifestyle, St. Michaels offers the perfect place to relax, recharge, and enjoy a

    Agent Photo

    Gretchen Wichlinski

    Compass

    (855) 695-6072

    204 E Marengo St, Saint Michaels, MD 21663
  • /25

    $219,900

    • 3 Beds
    • 1 Bath
    • 1,075 Sq Ft

    28 Clay St, Easton, MD 21601

    CALLING ALL INVESTORS! This property in Easton is the one you have been waiting for! This one will not last! This Property is being sold As-Is condition. Buyer is responsible for all certifications. Seller never occupied. Neither the seller or listing agent make any representation as to the accuracy of any information contained herein. Buyer must conduct their own due diligence, verification,

    Simran Dheer Tesla Realty Group, LLC

    28 Clay St, Easton, MD 21601
  • /10

    $280,000

    • 2 Beds
    • 1 Bath
    • 1,170 Sq Ft

    127 Chapel Rd, Easton, MD 21601

    2 bedroom 1 bath (possibility for third bedroom in attic) fixer upper with lots of potential. Centrally located in Easton with close access to Rails to Trails. Make this home your own or renovate as an investment property. Sold AS IS.

    rachael harrison Coldwell Banker Realty

    127 Chapel Rd, Easton, MD 21601
  • /25

    $639,900

    • 3 Beds
    • 3 Baths
    • 1,986 Sq Ft

    4794 Sailors Ln, Oxford, MD 21654

    Nestled on 2± acres, this inviting property offers a peaceful setting surrounded by mature trees that provide shade and natural beauty throughout the seasons. A circular driveway creates a welcoming approach and allows for easy access to the home and detached two-car garage, which also offers excellent potential as a workshop, studio, or hobby space. Inside, hardwood flooring extends throughout

    Chuck Mangold Benson & Mangold, LLC

    4794 Sailors Ln, Oxford, MD 21654
  • /28

    $384,900

    • 3 Beds
    • 2.5 Baths
    • 2,266 Sq Ft

    29053 Superior Cir, Easton, MD 21601

    Enjoy low-maintenance living in this well-maintained 3-bedroom, 2.5-bath townhome located in the desirable Lakelands community. Offering a spacious and versatile floor plan, the kitchen is equipped with stainless steel appliances and opens seamlessly to the main living area, with a cozy gas fireplace. The first-floor primary suite provides easy main-level living and features a private full bath

    Alicia Gannon Dulin Benson & Mangold, LLC

    29053 Superior Cir, Easton, MD 21601
  • /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
  • /3

    $285,000

    Coming Soon
    • 4 Beds
    • 2 Baths
    • 1,894 Sq Ft

    29775 Wye Oak St, Easton, MD 21601

    Great Rancher located in Matthewstown Run! Needs some TLC to make it shine again! Fenced in back yard, 2 car garage and great location make this a must see!

    Karla Wieland-Cherry Meredith Fine Properties

    29775 Wye Oak St, Easton, MD 21601
  • /77

    $1,165,000

    • 2 Beds
    • 2 Baths
    • 2,024 Sq Ft

    107 E Chestnut St, Saint Michaels, MD 21663

    Welcome to 107 E. Chestnut, a beautifully restored circa-1870 residence nestled in the heart of St. Michaels. From the moment you step inside, you are greeted by the perfect blend of timeless character and modern sophistication, where original architectural details have been thoughtfully preserved and seamlessly integrated with extensive renovations. The spacious entry combines an elegant living

    Monica Penwell TTR Sotheby's International Realty

    107 E Chestnut St, Saint Michaels, MD 21663
  • /14

    $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. More info and photos to follow.

    Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

    21441 Dogwood Cove Rd, Tilghman, MD 21671
  • /24

    $585,990

    New Construction
    • 5 Beds
    • 1.5 Baths
    • 4,031 Sq Ft

    1935 Silver Lake Ln, Trappe, MD 21673

    The Kendrick manages to create the best of both worlds with its thoughtfully designed layout. It maintains the timeless spaces like formal living and dining rooms, but incorporates them within an open, livable design. The great room, kitchen and breakfast area are open to each other, creating easy communication and a connected environment for your family. The main level can be expanded to include

    Brookfield Residential Builder
    1935 Silver Lake Ln, Trappe, MD 21673
  • /29

    $499,000

    • 3 Beds
    • 2 Baths
    • 1,574 Sq Ft

    934 Calvert Ave, Saint Michaels, MD 21663

    Welcome to this charming 3-bedroom, 2-bath home located on the edge of St. Michaels at the end of a quiet street. Thoughtfully maintained and updated, this property features a new roof, new downstairs HVAC system, updated appliances, and a spacious screened porch perfect for relaxing and entertaining.The main level includes a private office with its own exterior entrance, offering excellent

    Will Stone Benson & Mangold, LLC

    934 Calvert Ave, Saint Michaels, MD 21663
  • /43

    $425,000

    • 3 Beds
    • 2.5 Baths
    • 1,572 Sq Ft

    27990 Woods Rd, Easton, MD 21601

    Welcome to 27990 Woods Road! Situated on approximately 1/2 acre lot, this home and property has much to offer. A new fully fenced backyard offers privacy to the large back yard with a generous sized deck making it perfect for entertaining, enjoying relaxing time in the hot tub or tinkering in the shed. This split-level style home has 3 bedrooms and 2.5 bathrooms, a primary bedroom with an

    Marla Baines Meredith Fine Properties

    27990 Woods Rd, Easton, MD 21601

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