Talbot County MD Homes for Sale

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  /37

  $499,000

  • 2 Beds
  • 1 Bath
  • 1,080 Sq Ft

  105 Seymour Ave, Saint Michaels, MD 21663

  St. Michaels Charmer! Welcome Home to this Cozy Cottage perfectly situated in the desirable, walkable Historic Town of St. Michaels! Full of natural light and warmth, this inviting home offers comfortable living spaces and thoughtful updates. Spacious .25 acre lot with mature trees and flower gardens. Step inside to find a welcoming living room with real hardwood floors and a wood-burning brick

  Pamela Ackermann-Doll RE/MAX Executive

  105 Seymour Ave, Saint Michaels, MD 21663
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  /26

  $89,990

  • 3 Beds
  • 1 Bath
  • 1,166 Sq Ft

  13510 Main St, Queen Anne, MD 21657

  Welcome to 13510 Main Street in Queen Anne, Maryland—an opportunity wrapped in potential and priced with intention. This is an as-is sale, a true handyman special, and exactly the kind of investment property that experienced buyers, savvy renovators, and vision-driven homeowners are constantly searching for. If you have been waiting for a property with room to add value, build equity, and shape

  Evan Weissman Real Broker, LLC

  13510 Main St, Queen Anne, MD 21657
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  /37

  $525,000

  • 3 Beds
  • 2.5 Baths
  • 2,264 Sq Ft

  7184 Oxford Rd, Easton, MD 21601

  If privacy just minutes from everything is what you want—LOOK NO FURTHER • 3 acres of privacy while staying close to Easton’s shopping, dining, schools, and everyday essentials • Fully renovated throughout—everything is done and move-in ready • Main-level primary suite with a sitting room • Large fenced in area perfect for dogs & kids • Outbuilding with electric—ideal for a studio, office, or

  Kara Shaffer Engel & Völkers Annapolis

  7184 Oxford Rd, Easton, MD 21601
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  /3

  $295,000

  • Land
  • 0.55 Acre
  • $536,364 per Acre

  108 Miles, Saint Michaels, MD 21663

  A rare opportunity in the heart of St. Michaels: this half-acre+ wooded parcel offers the privacy of a tucked-away retreat with the everyday convenience of an in-town location. Restaurants, shops, seasonal events, waterfront parks, and the character of the historic district are all close at hand, yet the setting feels quiet and natural. Approximately three times the size of a typical in-town lot,

  Chuck Mangold Benson & Mangold, LLC

  108 Miles, Saint Michaels, MD 21663
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  /76

  $5,575,000

  • 5 Beds
  • 5.5 Baths
  • 7,287 Sq Ft

  9170 Hunting Creek Ln, Easton, MD 21601

  Set on 31 private acres along the peaceful waters of Hunting Creek, this exceptional Eastern Shore estate combines timeless architecture with modern sophistication. With over 1,000 feet of waterfront and approximately 6 feet of mean low water, the property offers deep-water access, stunning views, and an unmatched sense of privacy. The five-bedroom, five-and-a-half-bath residence has been

  Brad Kappel TTR Sotheby's International Realty

  9170 Hunting Creek Ln, Easton, MD 21601
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  /81

  $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
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  /68

  $1,900,000

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

  24390 Oakwood Park Rd, Saint Michaels, MD 21663

  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 feet, all on the main level,

  Janet Larson Benson & Mangold, LLC

  24390 Oakwood Park Rd, Saint Michaels, MD 21663
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  /36

  $385,000

  • 2 Beds
  • 1.5 Baths
  • 1,364 Sq Ft

  8805 Cummings Rd, Wittman, MD 21676

  Located in the waterfront village of Wittman, close to the public landing and county park, this beautifully crafted two-story cottage blends charm and character with thoughtful design. The home features 2 bedrooms, 1.5 baths, multiple living areas, 2 office spaces, and generous storage. Open beams, wood floors, and architectural details create a warm, inviting atmosphere throughout. Elevated and

  Wink Cowee Benson & Mangold, LLC

  8805 Cummings Rd, Wittman, MD 21676
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  /24

  $249,900

  • 2 Beds
  • 2 Baths
  • 1,368 Sq Ft

  125 S Higgins St, Easton, MD 21601

  Fully remodeled home. This 2 bedroom, 2 bathroom home in Easton’s Historic District has been completely remodeled and is ready for move in. With approximately 1,368 sqft +/-, this property features brand-new bathrooms, kitchen, appliances, flooring, carpeting, and fresh paint throughout. Situated on a corner lot, it offers a bright, open layout and modern finishes, making it ideal for first-time

  Peter Stark Benson & Mangold, LLC

  125 S Higgins St, Easton, MD 21601
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  /58

  $4,395,000

  • 4 Beds
  • 4 Baths
  • 7,903 Sq Ft

  5084 Ferry Neck Rd, Royal Oak, MD 21662

  Tucked within a canopy of trees along Maryland’s Eastern Shore, this remarkable home rests quietly beside the Choptank River. The setting feels worlds away, eighty acres of meadows and woodland that open gently to more than 1,800 feet of private shoreline, where a western exposure captures breathtaking sunsets reflected across the water. The residence at 5084 Ferry Neck Road was shaped by owners

  Ron Mangas TTR Sothebys International Realty

  5084 Ferry Neck Rd, Royal Oak, MD 21662
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  /72

  $1,235,000

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

  28711 Hope Cir, Easton, MD 21601

  Approximately 4500 square feet +/- , 3 Level, newly updated, 4/5-bedroom, Federal style home on a quiet circle. Newer kitchen and first floor owner's en suite, new sun room and finished third floor office/additional living space. Second floor includes two spacious bedrooms, two baths (one en suite); plus, private bonus/storage room which could easily be converted to a 6th bedroom or in-law suite.

  Brian Petzold Benson & Mangold, LLC

  28711 Hope Cir, Easton, MD 21601
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  /39

  $1,390,000

  • 3 Beds
  • 2 Baths
  • 4,008 Sq Ft

  28701 Edgemere Rd, Easton, MD 21601

  Privately situated along the Oxford Road corridor, Heron Rest is a custom Pam Gardner–designed waterfront home that beautifully blends Eastern Shore charm with modern functionality. Built in 1995 and set on approximately two acres overlooking Peachblossom Creek, this property embodies the essence of relaxed waterfront living.The home features cathedral ceilings and hardwood floors throughout

  Coard Benson Benson & Mangold, LLC

  28701 Edgemere Rd, Easton, MD 21601
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  /37

  $175,000

  • 2 Beds
  • 2 Baths
  • 1,357 Sq Ft

  3 Park Ln, Easton, MD 21601

  Two Bedroom, Two Full Bathroom in the Home in Sought-After Hyde Park 55+ Community Welcome to 3 Park Lane, a beautiful open floor double modular home nestled in the highly desired Hyde Park community of Easton, Maryland. This home is completely move in ready! Step inside to the bright, inviting open floor plan, the interior features all-new carpet and tile flooring (2025), updated light fixtures,

  Erene Katris Coldwell Banker Realty

  3 Park Ln, Easton, MD 21601
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  /26

  $250,000

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft

  305 Port St, Easton, MD 21601

  Constructed in 1948 this 2-bedroom, 1-bathroom brick bungalow has not been available on the market since 1989. The current tenants have resided in the property for over 20 years, indicating its strong appeal and potential. This residence is ideally suited for first-time buyers as well as investors seeking a valuable addition to their portfolio.Situated on a substantial corner lot, the home

  Nicole Clemente Keller Williams Realty

  305 Port St, Easton, MD 21601
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  /56

  $4,250,000 Open Sat 1PM - 3PM

  • 4 Beds
  • 7 Baths
  • 3,700 Sq Ft

  27473 Westpoint Rd, Easton, MD 21601

  Swan Point is an exquisite waterfront estate set on approximately 4.5 acres, offering sweeping westerly views across the Tred Avon River. A gated, paved driveway with cobblestone curbs welcomes you to this private retreat. This stately Colonial features 4 bedrooms, 4 full baths, and 3 half baths, thoughtfully designed for both intimate living and grand entertaining. The formal living room,

  Clifford Meredith Meredith Fine Properties

  27473 Westpoint Rd, Easton, MD 21601
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  /83

  $2,499,000

  • 5 Beds
  • 4.5 Baths
  • 4,303 Sq Ft

  21485 Island Club Rd, Tilghman, MD 21671

  Discover the essence of refined Eastern Shore living in this meticulously renovated contemporary waterfront retreat, gracefully set along the tranquil shores of Harris Creek and looking out to the Choptank River. Every detail of this remarkable home exemplifies elegance. Step inside to a breathtaking panorama of water views framed by expansive windows that fill the home with ethereal lighting.

  Alicia Gannon Dulin Benson & Mangold, LLC

  21485 Island Club Rd, Tilghman, MD 21671
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  /23

  $450,000

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  507 Bainbridge Place, Easton, MD 21601

  Very nice one story rancher style house with attached one car garage and additional pole building shed with concrete floors. This home is a perfect blend of style, comfort, and convenience, offering an exceptional opportunity in a prime location. Easton, Maryland, known as the New Hamptons of the Chesapeake Bay by Forbes Magazine, is conveniently located 1.5 hours from D.C. and Baltimore, and 2

  Edward Roe Meredith Fine Properties

  507 Bainbridge Place, Easton, MD 21601
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  /44

  $519,000

  • 3 Beds
  • 3 Baths
  • 2,990 Sq Ft

  29621 Charles Dr, Easton, MD 21601

  Located in the desirable non-age restricted section of Easton Club East, this spacious Vanderbuilt model offers 3 bedrooms, 3 bathrooms, and a versatile loft/bonus room. The main level features a bedroom suite with tray ceiling, a large walk-in closet, and a luxurious bathroom with Jacuzzi tub. Additional highlights include an office/library with built-ins, a formal dining room, and an eat-in

  Barbara Watkins Benson & Mangold, LLC

  29621 Charles Dr, Easton, MD 21601
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  /38

  $775,000

  • 3 Beds
  • 2.5 Baths
  • 2,819 Sq Ft

  28959 Jasper Ln, Easton, MD 21601

  Totally renovated and in perfect move in condition this private end unit in The Galloways is available for immediate occupancy! Recently remodeled with a sun room addition and beautiful pergola and deck along with a new HVAC compressor in needs absolutely nothing. As an end unit with excellent privacy it offers a 2 car garage, spacious foyer, office with cherry cabinetry, half bath, new kitchen

  Bill Wieland Benson & Mangold, LLC

  28959 Jasper Ln, Easton, MD 21601
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  /14

  $325,000

  • 3 Beds
  • 2 Baths
  • 3,924 Sq Ft

  22314 Pot Pie Rd, Wittman, MD 21676

  Rental Opportunity in Wittman, MD Positioned in the desirable community of Wittman, this 3 bedroom, 2 bath home situated on 0.84± commercially zoned acreage and premier road frontage presents a compelling opportunity for investors seeking potential rental income in Talbot County. The property offers comfortable living space, a rural Eastern Shore setting, and proximity to key employment,

  Shawn Moore Meredith Fine Properties

  22314 Pot Pie Rd, Wittman, MD 21676
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  /49

  $384,990

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

  305 Choptank Ave, Easton, MD 21601

  See the recent appraisal report uploaded to the listing. Discover exceptional value in the heart of Easton! This move-in-ready home offers effortless single-level living with a bright, open feel throughout. The spacious living area flows into a functional kitchen, perfect for everyday comfort and easy entertaining. Each bedroom provides generous space, natural light, and flexibility for guests, a

  Von Kirchhoff EXP Realty, LLC

  305 Choptank Ave, Easton, MD 21601
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  /32

  $399,900

  • 3 Beds
  • 2 Baths
  • 2,018 Sq Ft

  29202 Holly Rd, Easton, MD 21601

  Merry Christmas to YOU! This lovely home has living space for everyone to have separate space but still be together. Family room, finished sun room, all conveniently located minutes from downtown Easton. Sel One level living all on one level. This beautifully renovated 3-bedroom, 2-bath rancher is conveniently located in the desirable neighborhood of South Beechwood. Thoughtfully updated with

  Connie Loveland Benson & Mangold, LLC

  29202 Holly Rd, Easton, MD 21601
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  /39

  $749,500

  • 4 Beds
  • 2.5 Baths
  • 2,615 Sq Ft

  28872 Jasper Ln, Easton, MD 21601

  Discover time elegance and modern convenience in this beautifully appointed 4-bedroom, 2.5 bath end-unit townhome, perfectly positioned between Easton and Oxford in one of the area's most desirable and established communities. Surrounded by scenic walking trails, tranquil ponds, a dog park, tennis courts and more, this residence offers a lifestyle of comfort and community. Step inside to find

  Monica Penwell TTR Sotheby's International Realty

  28872 Jasper Ln, Easton, MD 21601
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  /30

  $439,000

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

  29736 Tallulah Ln, Easton, MD 21601

  Nestled in the serene community of Matthewstown Run, this exquisite Colonial-style residence offers a harmonious blend of elegance and comfort. Built in 2003, this meticulously maintained home spans 1,920 sq ft and is set on a 0.29-acre lot that backs to lush trees, providing a tranquil backdrop for your everyday life. Step inside to discover a warm and inviting interior that boasts an open floor

  James Bent Benson & Mangold, LLC

  29736 Tallulah Ln, Easton, MD 21601
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  /44

  $1,195,000

  • 3 Beds
  • 3 Baths
  • 2,085 Sq Ft

  24318 Oakwood Park Rd, Saint Michaels, MD 21663

  Welcome to Old House Cove Waterfront Retreat in St. Michaels, MDNestled on nearly half an acre with scenic frontage along Old House Cove, this quintessential Eastern Shore property offers a rare combination of waterfront serenity, literary history, and timeless design. The expansive parcel provides privacy in a highly desirable location, just minutes from the heart of St. Michael’s—one of

  Kathleen Eder Compass

  24318 Oakwood Park Rd, Saint Michaels, MD 21663
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  /19

  $325,000

  • 3 Beds
  • 1 Bath
  • 1,196 Sq Ft

  713 Howard St, Easton, MD 21601

  Charming 3-bedroom, 1-bath rancher conveniently located in Easton, MD—just minutes from town amenities, shopping, and dining. This 1,196± sq. ft. home offers easy, one-floor living with beautiful wood floors throughout and a large, fenced rear yard perfect for outdoor enjoyment includes storage shed. The spacious attic provides excellent storage options. Features include newer appliances, gas

  Barbara Watkins Benson & Mangold, LLC

  713 Howard St, Easton, MD 21601
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  /69

  $499,000

  • 4 Beds
  • 3.5 Baths
  • 4,304 Sq Ft

  29798 Captain Adamouski St, Easton, MD 21601

  4 BR 3 1/2 BA LOCATED IN HUNTER'S MILL WITH A FULLY FINISHED BASEMENT AND FENCED IN BACK YARD!

  Henry Gibbons-Neff Meredith Fine Properties

  29798 Captain Adamouski St, Easton, MD 21601
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  /31

  $349,900

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

  9134 Honeysuckle Dr, Easton, MD 21601

  Located in the Chapel East neighborhood, this split-level home offers a practical and inviting layout. The main-level features an open floor plan with the kitchen flowing into the living room, and updated flooring extends throughout the main-level and the finished basement. The basement provides a versatile space ideal for a recreation room, home office, or hobby area. Upstairs, there are three

  Chuck Mangold Benson & Mangold, LLC

  9134 Honeysuckle Dr, Easton, MD 21601
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  /27

  $425,000

  • 2 Beds
  • 1.5 Baths
  • 1,728 Sq Ft

  28538 Edgemere Rd, Easton, MD 21601

  Nestled in the charming Oxford Road neighborhood, this exquisite Cape Cod residence offers a harmonious blend of classic elegance and modern comfort. Built in 1951, this is an Estate Sale occupied by the same family since 1967. Three children were raised in this home, all currently solid and involved members of Talbot County. The design of this home showcases its timeless architectural style

  James Bent Benson & Mangold, LLC

  28538 Edgemere Rd, Easton, MD 21601
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  /37

  $515,000

  • 3 Beds
  • 2 Baths
  • 1,704 Sq Ft

  27240 Hayward Trail, Easton, MD 21601

  Exceptionally well-maintained rancher located on a quiet residential street (Hayward Trail) in the Doncaster community between Easton and St. Michaels. The 3-bedroom, 2-bath home features a spacious dining/family room addition w/fireplace and cathedral ceiling. A breezeway connects the house to a 2-car garage. The back yard is special, with a beautiful swimming pool and covered Tiki Bar/sitting

  Tom Crouch Benson & Mangold, LLC

  27240 Hayward Trail, Easton, MD 21601
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  /32

  $385,000

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

  9545 Quail Hollow Dr Unit 205, Saint Michaels, MD 21663

  Desirable Martingham Community is the location of this fabulous Quail Hollow unit nestled within the famous "links at Perry Cabin " , one of the few units with a screened porch . Enjoy the beautiful golf course views from the second floor, the first floor is private with its landscaping. Bathroom and kitchen countertops are granite, the kitchen has a space for a breakfast table, Living and

  Cornelia Heckenbach Long & Foster Real Estate, Inc.

  9545 Quail Hollow Dr Unit 205, Saint Michaels, MD 21663
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  /40

  $749,000

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

  9059 High Banks Dr, Easton, MD 21601

  Waterfront Cottage with Deep Water Dock on 2.3 Private Acres Beautifully maintained one-level waterfront cottage offering privacy, deep-water access, and Eastern Shore charm. Set on 2.3 wooded acres, this home features 3 bedrooms, 2 full baths, and an open, comfortable layout. Freshly painted and inspected, the home is move-in ready. The spacious kitchen opens to a large waterside family room

  Debbie Lipscomb Benson & Mangold, LLC

  9059 High Banks Dr, Easton, MD 21601
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  /71

  $705,000

  • 4 Beds
  • 3 Baths
  • 2,184 Sq Ft

  12654 Ocean Gateway, Cordova, MD 21625

  4 BR 3 BA HOUSE, ATTACHED 2 CAR GARAGE ON 5.8 ACRES! THIS PROPERTY IS IMPROVED BY A 5 STALL HORSE BARN WITH AN ADDITIONAL FOALING STALL, THREE BIG PATURES AND AN ADDITIONAL LARGE METAL BUILDING! THE NEIGHBORING PROPERTY LINE AND THE FRONT OF THE PROPERTY HAVE BEEN LINED WITH YOUNG CRAPE MYRTLE TREES. SINCE THE OWNER PURCHASED THIS PROPERTY, THEY HAVE PUT ON NEW SIDING, NEW WINDOWS, A NEW ROOF,

  Henry Gibbons-Neff Meredith Fine Properties

  12654 Ocean Gateway, Cordova, MD 21625
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  /37

  $419,000

  • 4 Beds
  • 2 Baths
  • 2,020 Sq Ft

  304 W Oak Ave, Easton, MD 21601

  Built in 1959 and enhanced with a spacious primary suite addition in 1995, this 3–4 bedroom, 2-bath home provides generous living space and a comfortable layout. The front covered porch leads into a bright living room with large windows overlooking the front yard. Beautiful original hardwood floors carry throughout much of the home. The open kitchen overlooks the dining area and sunroom. The home

  Kim Crouch Ozman Benson & Mangold, LLC

  304 W Oak Ave, Easton, MD 21601
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  /87

  $6,000,000

  • 3 Beds
  • 4 Baths
  • 5,921 Sq Ft

  5499 Anderby Hall Rd, Royal Oak, MD 21662

  Royal Oak - escape to your own Eastern Shore estate. Anderby Hall is part of an original 1680 land grant. This 12 +/- acre parcel features 3,260' +/- of shoreline (mostly rip rapped) including a tidal pond and island (accessed by bridge)to a private peninsula and private cove. The gated driveway leads to the main house- a 3000 +/- sq.ft. Colonial featuring a great room with fireplace, charming

  Valerie Brown Coldwell Banker Realty

  5499 Anderby Hall Rd, Royal Oak, MD 21662
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  /40

  $2,295,000

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

  7049 & 7047 Acorn Alley, 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 Alley, Royal Oak, MD 21662
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  /34

  $440,000

  • 3 Beds
  • 2 Baths
  • 2,032 Sq Ft

  8160 Ethan Ave, Easton, MD 21601

  Motivated seller - Welcome to this beautifully maintained 3-bedroom, 2-bathroom home nestled in the desirable Waylands community. Boasting over 2,000 square feet of freshly painted living space all on one level, this property offers the perfect blend of comfort, style, and functionality. Step into a welcoming foyer that opens into a bright, open-concept kitchen and living area. Gorgeous hardwood

  Stacie Luhrman Benson & Mangold, LLC

  8160 Ethan Ave, Easton, MD 21601
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  /44

  $780,000

  • 3 Beds
  • 2.5 Baths
  • 2,065 Sq Ft

  0 Lot 16 N Unit MDTA2012070, Easton, MD 21601

  Discover the charm of historic Easton in this thoughtfully designed new construction home, perfectly situated within walking distance to the heart of town. This custom-built residence blends modern living with timeless appeal, featuring a desirable main-level primary bedroom, spacious two-car garage, inviting backyard, and the opportunity to personalize finishes to your taste. Enjoy the

  Jana Meredith Meredith Fine Properties

  0 Lot 16 N Unit MDTA2012070, Easton, MD 21601
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  /53

  $1,750,000

  • 4 Beds
  • 6 Baths
  • 4,399 Sq Ft

  28630 Edgemere Rd, Easton, MD 21601

  Designed by William Draper Brinckloe, one of Easton’s best early 20th Century architects, this Mission house, “Edgemar”, is nestled on a private 4.5-acre double lot and offers an exceptional blend of character, comfort, and serenity. The property boasts a dock with a highly coveted boathouse (that can no longer be built), a natural shoreline, and mature landscaping highlighted by 100-year-old

  Clifford Meredith Meredith Fine Properties

  28630 Edgemere Rd, Easton, MD 21601
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  /60

  $3,795,000

  • 5 Beds
  • 5.5 Baths
  • 6,487 Sq Ft

  8781 Tilghman Island Rd, Wittman, MD 21676

  A magnificent, stately, Daffin-built, Chesapeake Bay Brick Estate exudes excellent design and craftsmanship in this 5 bedroom (suites) , 5.5 bath 6,500 sq. ft brick home that majestically sits on 21.7 acres facing the Chesapeake Bay. Excellent construction quality and design are evident throughout this magnificent estate. Geothermal system on 1st and 2nd floors; Heat Pump for the 3rd floor;

  Robert Lacaze TTR Sotheby's International Realty

  8781 Tilghman Island Rd, Wittman, MD 21676

Showing Results 81 - 120, Page 3 of 8