49

Ranch Style Homes for Sale in Talbot County MD

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  • 28715 Jacks Field Rd, Wye Mills, MD 21679
    28715 Jacks Field Rd, Wye Mills, MD 21679
    28715 Jacks Field Rd, Wye Mills, MD 21679
    /27

    $925,000

    $24K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,981 Sq Ft

    28715 Jacks Field Rd, Wye Mills, MD 21679

    Set on a peaceful two-acre lot in Wye Mills, 28715 Jacks Field Road has been thoughtfully updated from top to bottom, offering the space, functionality, and modern finishes today’s buyers are looking for. This spacious five-bedroom, three-bath home features a newly reimagined interior with new flooring throughout, custom blinds, and a series of high-impact upgrades that elevate both everyday

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (410) 593-1432

    28715 Jacks Field Rd, Wye Mills, MD 21679
  • 4794 Sailors Ln, Oxford, MD 21654
    4794 Sailors Ln, Oxford, MD 21654
    4794 Sailors Ln, Oxford, MD 21654
    /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
  • 3750 Windy Hill Rd, Trappe, MD 21673
    3750 Windy Hill Rd, Trappe, MD 21673
    3750 Windy Hill Rd, Trappe, MD 21673
    /53

    $1,900,000

    • 3 Beds
    • 2 Baths
    • 1,966 Sq Ft

    3750 Windy Hill Rd, Trappe, MD 21673

    Talbot County Farm With Country Home, Multiple Outbuildings And Tillable AcThis exceptional farm in Talbot County, Maryland, presents a rare opportunity to own a highly productive Eastern Shore property that combines agricultural value, quality improvements, and premier recreational appeal. Situated in a region known for its fertile soils and strong farming history, this 90 acre home farm

    James Young LPT Realty, LLC

    3750 Windy Hill Rd, Trappe, MD 21673
  • 5648 Trafalgar Cir, Tilghman, MD 21671
    5648 Trafalgar Cir, Tilghman, MD 21671
    5648 Trafalgar Cir, Tilghman, MD 21671
    /43

    $544,888

    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
  • 68 Park Ln, Easton, MD 21601
    68 Park Ln, Easton, MD 21601
    68 Park Ln, Easton, MD 21601
    /16

    $150,000

    • 2 Beds
    • 2 Baths
    • 1,352 Sq Ft

    68 Park Ln, Easton, MD 21601

    Priced below appraised value! Step into a new chapter of carefree living in the vibrant Hyde Park/ Sun Community located in Easton, MD. This home with 2 generously sized bedrooms and 2 full baths offers spacious, open living/dining /kitchen, separate laundry room and lots of closets. There is a bright three-seasons room—complete with separate side access. The open-concept living, dining, and

    Traci Jordan Meredith Fine Properties

    68 Park Ln, Easton, MD 21601
  • 818 Applewood Ct, Easton, MD 21601
    818 Applewood Ct, Easton, MD 21601
    818 Applewood Ct, Easton, MD 21601
    /16

    $334,000

    $35K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,566 Sq Ft

    818 Applewood Ct, Easton, MD 21601

    3 bedroom rancher conveniently located in town on quiet cul-de-sac. Large 1/3 acre lot with fenced in back yard, screened porch, deck ,and small storage shed. Quiet neighborhood. New roof 2021. Walking distance to Rails to-Trails and John Ford Park. Sold As Is. Priced below recent appraisal

    Carl Treat Meredith Fine Properties

    818 Applewood Ct, Easton, MD 21601
  • 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
  • 7049 & 7047 Acorn Aly, Royal Oak, MD 21662
    7049 & 7047 Acorn Aly, Royal Oak, MD 21662
    7049 & 7047 Acorn Aly, Royal Oak, MD 21662
    /40

    $2,095,000

    • 6 Beds
    • 3.5 Baths
    • 1,454 Sq Ft

    7049 & 7047 Acorn Aly, Royal Oak, MD 21662

    **Discover Your Waterfront Oasis in Royal Oak** Nestled in the charming town of Royal Oak, these exceptional waterfront properties present breathtaking views of Oak Creek, conveniently located near the Miles River and the renowned Chesapeake Bay. Positioned between the picturesque communities of Saint Michael’s and Easton, this rare gem boasts approximately 541 feet of pristine water frontage,

    Blaine Williamson McClain-Williamson Realty, LLC

    7049 & 7047 Acorn Aly, Royal Oak, MD 21662
  • 6524 Oxford Rd, Easton, MD 21601
    6524 Oxford Rd, Easton, MD 21601
    6524 Oxford Rd, Easton, MD 21601
    /72

    $799,999

    $95K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,891 Sq Ft

    6524 Oxford Rd, Easton, MD 21601

    Positioned along the picturesque 5th fairway of the prestigious Talbot Country Club, this comprehensively renovated Easton residence blends timeless Eastern Shore charm with elevated modern design. Privately set on beautifully landscaped grounds with sweeping golf course vistas, the property offers refined one-level living in one of Talbot County’s most desirable country club settings.

    Eddie Mangold Benson & Mangold, LLC

    6524 Oxford Rd, Easton, MD 21601
  • 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
  • 6608 Ocean Gateway, Easton, MD 21601
    6608 Ocean Gateway, Easton, MD 21601
    6608 Ocean Gateway, Easton, MD 21601
    /84

    $399,000

    • 3 Beds
    • 2 Baths
    • 1,756 Sq Ft

    6608 Ocean Gateway, Easton, MD 21601

    JUST REDUCED Seller offers 15,000.00 seller concession for home improvements, sale price to be SOLD AS IS . Waterfront Views on Peach Blossom Creek – 6608 Ocean Gateway, Easton, MDThis property presents a solid investment potential for those ready to customize and improve. The functional three-bedroom two bath configuration combined with outdoor amenities and proximity to Oxford, Saint

    Levin Elzey Long & Foster Real Estate, Inc.

    6608 Ocean Gateway, Easton, MD 21601
  • 21647 Camper Cir, Tilghman, MD 21671
    21647 Camper Cir, Tilghman, MD 21671
    21647 Camper Cir, Tilghman, MD 21671
    /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
  • 28567 Holden Rd, Easton, MD 21601
    28567 Holden Rd, Easton, MD 21601
    28567 Holden Rd, Easton, MD 21601
    /45

    $719,500

    $30K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft

    28567 Holden Rd, Easton, MD 21601

    Enjoy easy one-level living in this charming 3-bedroom home located in the highly desirable Oxford Road corridor, offering lovely views of Peachblossom Creek and access to private waterfront lot . Inside, the home features a bright open kitchen with a marble island and huge walk in pantry. The living room offers a cozy gas insert fireplace, while the foyer welcomes you with attractive tile

    Barbara Watkins Benson & Mangold, LLC

    28567 Holden Rd, Easton, MD 21601
  • 6976 Travelers Rest Cir, Easton, MD 21601
    6976 Travelers Rest Cir, Easton, MD 21601
    6976 Travelers Rest Cir, Easton, MD 21601
    /50

    $2,675,000

    Open Sun 12PM - 2PM
    • 3 Beds
    • 3 Baths
    • 7,949 Sq Ft

    6976 Travelers Rest Cir, Easton, MD 21601

    Welcome to Soleil on the Bay! Nestled on nearly 7 acres along the calm, deep waters of Maxmore Creek—just off the Tred Avon River—this exceptional west-facing waterfront property offers the most gorgeous sunsets and wide-open water views providing the perfect blend of privacy, natural beauty, and endless potential. Ideally located between Easton and St. Michaels, it provides easy access to the

    Clifford Meredith Meredith Fine Properties

    6976 Travelers Rest Cir, Easton, MD 21601
  • 4938 Old Trappe Rd, Trappe, MD 21673
    4938 Old Trappe Rd, Trappe, MD 21673
    4938 Old Trappe Rd, Trappe, MD 21673
    /10

    $329,000

    $21K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,378 Sq Ft

    4938 Old Trappe Rd, Trappe, MD 21673

    Situated on 2.6 private acres, this 3-bedroom, 2-bath Rancher offers peaceful country living with low-maintenance convenience. Recent updates include a newer roof and AC system, both only a few years old. The property provides plenty of space to enjoy the outdoors, with the added possibility of hunting right on your own land. A great opportunity for those seeking privacy, nature, and comfortable

    Eddie Matthews Benson & Mangold, LLC

    4938 Old Trappe Rd, Trappe, MD 21673
  • 28 Clay St, Easton, MD 21601
    28 Clay St, Easton, MD 21601
    28 Clay St, Easton, MD 21601
    /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
  • 29688 Shockley Ln, Cordova, MD 21625
    29688 Shockley Ln, Cordova, MD 21625
    /2

    $134,900

    $15K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,248 Sq Ft

    29688 Shockley Ln, Cordova, MD 21625

    Price Improvement!! Unlock the potential of this affordable 3- bedroom fixer upper on nearly a half acre! Nestled in a peaceful rural setting yet just minutes from in-town conveniences , this property offers the best of both worlds. Enjoy easy access to major highways , plus prime location only 25 minutes to the Bay Bridge and 40 minutes to Delaware. Whether you're an investor looking to create

    Myisha Walker Long & Foster Real Estate, Inc.

    29688 Shockley Ln, Cordova, MD 21625
  • 9108 Glebe Creek Rd, Easton, MD 21601
    9108 Glebe Creek Rd, Easton, MD 21601
    9108 Glebe Creek Rd, Easton, MD 21601
    /19

    $349,900

    • 3 Beds
    • 2 Baths
    • 1,467 Sq Ft

    9108 Glebe Creek Rd, Easton, MD 21601

    Opportunity meets lifestyle in this ideally located 3-bedroom, 2-bath residence just minutes from Easton. Set in a peaceful Eastern Shore setting, this home offers the rare chance to reimagine and elevate a property in a highly desirable area. Inside, a classic brick fireplace anchors the living space, ready to become the centerpiece of a thoughtfully redesigned interior. The home’s layout

    Michael Dillon Benson & Mangold, LLC

    9108 Glebe Creek Rd, Easton, MD 21601
  • 9829 Bantry Rd, Easton, MD 21601
    9829 Bantry Rd, Easton, MD 21601
    9829 Bantry Rd, Easton, MD 21601
    /66

    $499,900

    $50K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,888 Sq Ft

    9829 Bantry Rd, Easton, MD 21601

    Drive down a country lane surrounded by farmland & woods to the lovely neighborhood of Bantry. Enjoy your own 5+acres with a circular driveway & scenic surroundings. Welcome to your single level home w/ full front porch, lots of decking & a warm interior. Gather around the fireplace or enjoy a window filled great room w/ wood burning stove & access to extensive decking which overlooks the

    Barbara Best RE/MAX One

    9829 Bantry Rd, Easton, MD 21601
  • 225 Bethune Dr, Easton, MD 21601
    225 Bethune Dr, Easton, MD 21601
    225 Bethune Dr, Easton, MD 21601
    /32

    $399,000

    • 3 Beds
    • 2 Baths
    • 1,454 Sq Ft

    225 Bethune Dr, Easton, MD 21601

    Built in 2016, this well-maintained home offers comfortable one-level living with a bright, open floor plan. Featuring 9’ ceilings and laminate wood flooring throughout, the home welcomes you through a foyer that flows into the main living area. The kitchen is thoughtfully designed with granite countertops, stainless steel appliances, ample cabinetry, a pantry and an island with bar seating

    Kim Crouch Ozman Benson & Mangold, LLC

    225 Bethune Dr, Easton, MD 21601
  • 225 Tyler Ave, Saint Michaels, MD 21663
    225 Tyler Ave, Saint Michaels, MD 21663
    225 Tyler Ave, Saint Michaels, MD 21663
    /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
  • 29316 Will St, Easton, MD 21601
    29316 Will St, Easton, MD 21601
    29316 Will St, Easton, MD 21601
    /31

    $354,900

    $5K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,408 Sq Ft

    29316 Will St, Easton, MD 21601

    Cute as a button Updated Rancher Easton – 29316 Will Street Welcome to this adorable, move-in ready rancher that perfectly blends comfort, functionality, and style! Nestled in a convenient Easton location, this well-maintained home shines with thoughtful updates throughout.Step inside to discover a warm and inviting interior, ideal for everyday living or entertaining. Major improvements

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    29316 Will St, Easton, MD 21601
  • 8724 Harper Way, Easton, MD 21601
    8724 Harper Way, Easton, MD 21601
    8724 Harper Way, Easton, MD 21601
    /35

    $448,990

    New Construction
    • 4 Beds
    • 2 Baths
    • 1,774 Sq Ft

    8724 Harper Way, Easton, MD 21601

    Introducing 8724 Harper Way, a new home beginning construction in the Gannon Range community of Easton, MD. The Cali is a sizeable single-story home optimizing every bit of its 1,774 square feet with four bedrooms, two full baths, a covered back patio, and a two-car garage. As you enter the home, a guest bathroom sits conveniently between two secondary bedrooms. Continuing down the hallway, you

    Justin Wood D.R. Horton Realty of Virginia, LLC

    8724 Harper Way, Easton, MD 21601
  • 29311 Pin Oak Way, Easton, MD 21601
    29311 Pin Oak Way, Easton, MD 21601
    29311 Pin Oak Way, Easton, MD 21601
    /26

    $339,000

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft

    29311 Pin Oak Way, Easton, MD 21601

    Well-maintained and move-in ready, this charming 1,344± sqft home is located in the South Beechwood community and offers easy one-level living. Luxury vinyl plank flooring flows throughout, enhancing the home’s clean and modern feel. The spacious living room features a cozy wood stove with a white washed brick mantel and hearth, along with a large bay window that fills the space with natural

    Kim Crouch Ozman Benson & Mangold, LLC

    29311 Pin Oak Way, Easton, MD 21601
  • 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
  • 10640 Kittys Corner Rd, Cordova, MD 21625
    10640 Kittys Corner Rd, Cordova, MD 21625
    10640 Kittys Corner Rd, Cordova, MD 21625
    /20

    $383,980

    • 3 Beds
    • 2 Baths
    • 1,568 Sq Ft

    10640 Kittys Corner Rd, Cordova, MD 21625

    “This property has been recently updated with a new central air conditioning and heating system.” Welcome to your serene retreat on the Eastern Shore! This charming 3-bedroom, 2-bathroom home offers the perfect blend of comfort and tranquility, set on two acres of beautifully cleared land. The expansive land provides endless possibilities, providing ample room for outdoor activities, gardening,

    Euricka Pindell Berkshire Hathaway HomeServices PenFed Realty

    10640 Kittys Corner Rd, Cordova, MD 21625
  • 24390 Oakwood Park Rd, Saint Michaels, MD 21663
    24390 Oakwood Park Rd, Saint Michaels, MD 21663
    24390 Oakwood Park Rd, Saint Michaels, MD 21663
    /68

    $1,679,000

    • 4 Beds
    • 3.5 Baths
    • 2,839 Sq Ft

    24390 Oakwood Park Rd, Saint Michaels, MD 21663

    Significant price improvement! Welcome to your private waterfront retreat just minutes from the charming, historic town of St. Michaels, Maryland. Tucked away on a quiet cul-de-sac in the serene Oakwood Park community along San Domingo Creek, this one-story residence offers four bedrooms, three and a half baths, and a harmonious blend of space and comfort. With approximately 2,839 finished square

    Janet Larson Benson & Mangold, LLC

    24390 Oakwood Park Rd, Saint Michaels, MD 21663
  • 21869 Albie Rd, Sherwood, MD 21665
    21869 Albie Rd, Sherwood, MD 21665
    21869 Albie Rd, Sherwood, MD 21665
    /39

    $575,000

    • 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
  • 311 Choptank Ave, Easton, MD 21601
    311 Choptank Ave, Easton, MD 21601
    311 Choptank Ave, Easton, MD 21601
    /13

    $335,000

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,580 Sq Ft

    311 Choptank Ave, Easton, MD 21601

    Enjoy one-level living in a desirable neighborhood conveniently located near downtown Easton, the Rails-to-Trails, and with easy access to Route 50. This home offers 3 bedrooms, 2 full baths, and a spacious living room featuring a large picture window that fills the space with natural light. The kitchen and dining area are open to one another, creating a functional layout ideal for everyday

    Traci Jordan Meredith Fine Properties

    311 Choptank Ave, Easton, MD 21601
  • 30050 Beaver Dam Rd, Trappe, MD 21673
    30050 Beaver Dam Rd, Trappe, MD 21673
    30050 Beaver Dam Rd, Trappe, MD 21673
    /41

    $570,000

    Open Sat 11AM - 2PM Coming Soon
    • 3 Beds
    • 2 Baths
    • 2,489 Sq Ft

    30050 Beaver Dam Rd, Trappe, MD 21673

    Open House - 6/27 - 11:00am-2:00pm Nestled on just over 2 acres in Trappe, this spacious 3-bedroom, 2-bath home offers nearly 2,500 square feet of living space with room to grow, gather, and make lasting memories. Inside, you'll find a large eat-in kitchen with center island and abundant wine storage, separate dining room, family room, and living room—providing plenty of space for everyday life,

    Sara Reynolds Coldwell Banker Chesapeake Real Estate Company

    30050 Beaver Dam Rd, Trappe, MD 21673
  • 507 Hazelwood Dr, Easton, MD 21601
    507 Hazelwood Dr, Easton, MD 21601
    507 Hazelwood Dr, Easton, MD 21601
    /19

    $325,000

    • 3 Beds
    • 2 Baths
    • 1,246 Sq Ft

    507 Hazelwood Dr, Easton, MD 21601

    This charming ranch-style home in the Fausley subdivision offers a perfect blend of comfort and functionality. Built in 1983, this detached residence features a traditional floor plan with 1,246 sq. ft. of well-utilized space, ideal for modern living. The interior boasts three spacious bedrooms and two full bathrooms, and a four season sunroom providing ample room for relaxation and privacy. The

    James Bent Benson & Mangold, LLC

    507 Hazelwood Dr, Easton, MD 21601
  • 24555 Deepwater Point Dr, Saint Michaels, MD 21663
    24555 Deepwater Point Dr, Saint Michaels, MD 21663
    24555 Deepwater Point Dr, Saint Michaels, MD 21663
    /24

    $725,000

    $44K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,072 Sq Ft

    24555 Deepwater Point Dr, Saint Michaels, MD 21663

    This sturdy brick ranch sits on a premium lot backing up to The Links at Perry Cabin Golf Course in St. Michaels, MD. A park like setting with mature specimen trees and shrubs. It's a 4 BR, 3 full bath, one level for easy living. New updated flooring. The Martingham Subdivision provides a waterfront community lot to enjoy the Miles River constant boat shows. Wednesday night sailboat races, fourth

    Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

    24555 Deepwater Point Dr, Saint Michaels, MD 21663
  • 100 Bush Terrace, Saint Michaels, MD 21663
    100 Bush Terrace, Saint Michaels, MD 21663
    100 Bush Terrace, Saint Michaels, MD 21663
    /40

    $470,000

    $30K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft

    100 Bush Terrace, Saint Michaels, MD 21663

    This home allows for a 3.12% FHA Assumable Loan! Welcome to easy Eastern Shore living in the charming waterfront town of St. Michaels! This 3-bedroom, 2 bath, 1,232 sq. ft. home is located in the desirable community of Rio Vista offering direct access to the Miles River, complete with a community dock, boat slips, and boat ramp — perfect for boating, crabbing, paddleboarding, or sunset cruises.

    Cheri Bruce-Phipps TTR Sotheby's International Realty

    100 Bush Terrace, Saint Michaels, MD 21663
  • 127 Chapel Rd, Easton, MD 21601
    127 Chapel Rd, Easton, MD 21601
    127 Chapel Rd, 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
  • 3900 Harrison Cir, Trappe, MD 21673
    3900 Harrison Cir, Trappe, MD 21673
    3900 Harrison Cir, Trappe, MD 21673
    /23

    $329,000

    • 3 Beds
    • 1 Bath
    • 1,196 Sq Ft

    3900 Harrison Cir, Trappe, MD 21673

    This easy one level living rancher is located in a quiet neighborhood between Easton and Cambridge on the scenic eastern shore of Maryland. There is a pond and playground within the community for residents use. You will enjoy relaxing on the rear screened in deck that overlooks a generous backyard. Appliances, window treatments, and 2 outdoor storage sheds convey with sale. This would make a

    Jeremy McDonough Mr. Lister Realty

    3900 Harrison Cir, Trappe, MD 21673
  • 101 Brooks Ln, Saint Michaels, MD 21663
    101 Brooks Ln, Saint Michaels, MD 21663
    101 Brooks Ln, Saint Michaels, MD 21663
    /28

    $425,000

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft

    101 Brooks Ln, Saint Michaels, MD 21663

    Welcome to this beautifully updated cottage in the heart of St. Michaels—where modern comfort meets Eastern Shore charm. Perfectly situated within walking distance to the town’s shops, restaurants, Rails to Trails, and the renowned Maritime Museum, this single‐level home offers both convenience and a peaceful, private setting. Sitting on nearly a quarter acre, the property features a fully fenced

    Stacie Luhrman Benson & Mangold, LLC

    101 Brooks Ln, Saint Michaels, MD 21663
  • 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
  • 108 Miles, Saint Michaels, MD 21663
    108 Miles, Saint Michaels, MD 21663
    108 Miles, Saint Michaels, MD 21663
    /25

    $779,000

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,710 Sq Ft

    108 Miles, Saint Michaels, MD 21663

    A rare opportunity to pair a half-acre+ wooded in-town parcel with a thoughtfully designed single-level home concept in the heart of St. Michaels. This Concept A plan illustrates a 3-bedroom, 2-bath residence totaling approximately 1,710 square feet, featuring one-level living and an attached one-car garage. Designed to maximize functionality and flow, the concept offers flexible living spaces

    Chuck Mangold Benson & Mangold, LLC

    108 Miles, Saint Michaels, MD 21663
  • 29775 Wye Oak St, Easton, MD 21601
    29775 Wye Oak St, Easton, MD 21601
    29775 Wye Oak St, Easton, MD 21601
    /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
  • 29387 Stoney Ridge Cir, Easton, MD 21601
    29387 Stoney Ridge Cir, Easton, MD 21601
    29387 Stoney Ridge Cir, Easton, MD 21601
    /30

    $399,900

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

    29387 Stoney Ridge Cir, Easton, MD 21601

    BRAND NEW ROOF and additional upgrades in 2026! The impeccably well-maintained RAISED RAMBLER with a lower level and attached garage is deceptively spacious. The surprisingly large interior defies its smaller exterior appearance. Sitting on a picturesque half-acre lot and boasting over 3,450 sq. ft. of total living space. Perfectly designed to support MULTI-GENERATIONAL or ONE LEVEL LIVING. Get

    Robin Gross Berkshire Hathaway HomeServices PenFed Realty

    29387 Stoney Ridge Cir, Easton, MD 21601

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