Talbot County MD Houses for Sale

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  /26

  $550,000

  $25K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,252 Sq Ft

  10490 Longwoods Rd, Easton, MD 21601

  Tucked away in a quiet country setting just minutes from downtown Easton and convenient access to Rt. 50, this well-maintained Cape Cod offers the perfect balance of privacy and accessibility. Set on a .63-acre lot backing to open space, the home features a bright and inviting main living area with wood flooring, a wood-burning fireplace, and soaring cathedral ceilings that create an open, airy

  

  Brian Gearhart

  Benson & Mangold, LLC

  10490 Longwoods Rd, Easton, MD 21601
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  /41

  $1,995,000

  • 5 Beds
  • 3.5 Baths
  • 3,906 Sq Ft

  5698 Leeward Ln, Tilghman, MD 21671

  Experience sweeping western-facing views of the Chesapeake Bay from this beautifully renovated waterfront retreat in Tilghman Island. Thoughtfully redesigned and updated in 2023, this exceptional property seamlessly blends refined coastal living with the tranquility and natural beauty of its extraordinary waterfront setting.Inside, the light-filled great room is the heart of the home, with

  

  Brian Gearhart

  Benson & Mangold, LLC

  5698 Leeward Ln, Tilghman, MD 21671
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  /56

  $2,995,000

  • 3 Beds
  • 5 Baths
  • 4,305 Sq Ft

  6906 Travelers Rest Cir, Easton, MD 21601

  "Cypress Lodge" - Tucked away on a private waterfront lot along the Tred Avon River, this striking contemporary-style residence offers expansive water views, exceptional privacy, and thoughtfully designed indoor-outdoor living. The 3-bedroom, 5-bath home features an open floorplan filled with natural light, highlighted by soaring vaulted cathedral ceilings and clean architectural lines that

  

  Brian Gearhart

  Benson & Mangold, LLC

  6906 Travelers Rest Cir, Easton, MD 21601
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  /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

  

  Brian Gearhart

  Benson & Mangold, LLC

  28715 Jacks Field Rd, Wye Mills, MD 21679
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  /35

  $1,095,000

  • 3 Beds
  • 2.5 Baths
  • 2,242 Sq Ft

  100 W Pier St, Oxford, MD 21654

  Waterfront, a deeded boat slip, off-street parking, and a single-car garage with additional storage set the stage for this thoughtfully redesigned coastal retreat in the heart of Oxford. Completely renovated from top to bottom, this 3 bedroom, 2.5 bathroom home blends timeless Eastern Shore charm with luxury finishes and exceptional boating amenities. Every detail has been carefully curated, from

  

  Brian Gearhart

  Benson & Mangold, LLC

  100 W Pier St, Oxford, MD 21654
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  /67

  $1,625,000

  • 3 Beds
  • 3 Baths
  • 3,606 Sq Ft

  32137 Discovery Dr, Easton, MD 21601

  Welcome to White Barn at Middlespring, a remarkable 8-acre Eastern Shore estate offering the perfect blend of historic charm, modern updates, privacy, and country living. Set at the end of a quarter-mile private drive surrounded by picturesque farmland, this exceptional property features three distinctive structures: a beautifully restored 1824 manor home, a 3-car detached garage with finished

  

  Brian Gearhart

  Benson & Mangold, LLC

  32137 Discovery Dr, Easton, MD 21601
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  /64

  $1,099,000

  • 3 Beds
  • 3 Baths
  • 3,853 Sq Ft

  6670 Tilghman Island Rd, Sherwood, MD 21665

  Reduced Price! Amazing opportunity to be on the water in Talbot County. Waterfront home situated on Back Creek in Sherwood. Conveniently located near St Michaels and Tilghman Island, the property includes views of sunsets over Poplar Island and is located minutes from restaurants, and shopping. Interior features include hickory hardwood floors, custom built-ins, crown molding, and recessed

  

  Larry Brennan

  TTR Sotheby's International Realty

  6670 Tilghman Island Rd, Sherwood, MD 21665
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  /73

  $5,045,000

  $200K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 4,172 Sq Ft

  8051 Leehaven Rd, Easton, MD 21601

  8051 Leehaven Road is the only property of its kind on the Eastern Shore right now — a custom-built waterfront estate move-in ready, and available today. This is not a project. It is not a renovation waiting to happen. It is +/-4,800 square feet of considered, uncompromising construction sitting on a private waterfront lot with direct access to the Chesapeake Bay, a Gunite saltwater pool with

  

  Tracy Higgs-Wagner

  Meredith Fine Properties

  8051 Leehaven Rd, Easton, MD 21601
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  /75

  $564,000

  $5K PRICE DROP

  • 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

  

  John McGlannan

  Meredith Fine Properties

  5559 Trafalgar Cir, Tilghman, MD 21671
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  /73

  $395,000

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft

  11778 Old Skipton Rd, Cordova, MD 21625

  Online Bidding Open: High Visibility Corner Property on Busy Route 50 - Perfect for Living & Business! Exceptional Opportunity in Cordova, MD! This stunning corner property boasts almost 1.5 acres of land on Route 50, offering high visibility and traffic flow.This renovated home is perfect for owner living and operating a good-sized low profile retail business, such as a real estate,

  

  Jane Gharfeh

  Taylor Properties

  11778 Old Skipton Rd, Cordova, MD 21625
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  /39

  $849,000

  Open Sat 2PM - 4PM

  • 3 Beds
  • 2 Baths
  • 1,288 Sq Ft

  803 New Ln, Saint Michaels, MD 21663

  Thoughtfully reimagined from the studs out, this exceptional residence offers the character of an in-town cottage with the quality, comfort, and finishes of a newly constructed home. Every detail has been carefully considered, creating a seamless blend of timeless charm and modern design. A welcoming front porch with a classic porch swing sets the tone before stepping inside to a light-filled

  

  Larry Brennan

  TTR Sotheby's International Realty

  803 New Ln, Saint Michaels, MD 21663
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  /45

  $950,000

  $55K PRICE INCREASE

  • 4 Beds
  • 3 Baths
  • 2,850 Sq Ft

  4938 Fairbank Rd, Tilghman, MD 21671

  *INCOME PRODUCING* 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

  

  Tracy Higgs-Wagner

  Meredith Fine Properties

  4938 Fairbank Rd, Tilghman, MD 21671
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  /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.

  

  Elizabeth Tryon

  Coldwell Banker Realty

  7316 Casey Ave, Easton, MD 21601
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  /28

  $372,000

  $18K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,880 Sq Ft

  29331 Fourth St, Easton, MD 21601

  Welcome to 29331 Fourth Street! This charming split level 3 bedroom 2 bath house is situated on a well shaded lot perfect for outdoor entertaining. The beautifully updated kitchen has an entire wall of cabinets and eating area. Open living area, with a family room in the basement. Basement also has a large laundry area with great storage. Short walk to the community park!

  

  Elizabeth Tryon

  Coldwell Banker Realty

  29331 Fourth St, Easton, MD 21601
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  /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

  

  John McGlannan

  Meredith Fine Properties

  21406 Dogwood Cove Rd, Tilghman, MD 21671
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  /134

  $7,800,000

  • 4 Beds
  • 4.5 Baths
  • 7,407 Sq Ft

  22101 Grafton Manour Ln, Wittman, MD 21676

  Grafton Manour Estate—A Rare Chesapeake Waterfront Legacy. Embrace the quiet grandeur of Grafton Manour Estate, an 86±-acre peninsula wrapped by approximately 1.5± miles of shoreline with panoramic water views in every direction. Bordered by Briary Cove to the east, Harris Creek to the southeast, and Waterhole Cove to the west, this extraordinary property blends pastoral elegance with true

  

  Tracy Higgs-Wagner

  Meredith Fine Properties

  22101 Grafton Manour Ln, Wittman, MD 21676
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  /72

  $549,999

  $25K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft

  204 E Marengo St, Saint Michaels, MD 21663

  Priced to sell! 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,

  

  Gretchen Wichlinski

  Compass

  204 E Marengo St, Saint Michaels, MD 21663
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  /35

  $475,000

  • 3 Beds
  • 2.5 Baths
  • 2,072 Sq Ft

  5933 Tilghman Island Rd, Tilghman, MD 21671

  Unique, one-of-a-kind property located in the heart of Tilghman Island, offering unparalleled tranquility and breathtaking water views overlooking Dogwood Harbor. Welcome to your private Eastern Shore retreat! This beautifully updated water-view home captures the essence of coastal living with sweeping views of the harbor and surrounding wildlife. Enjoy stunning sunsets and peaceful mornings from

  

  John McGlannan

  Meredith Fine Properties

  5933 Tilghman Island Rd, Tilghman, MD 21671
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  /77

  $799,000

  $26K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,648 Sq Ft

  8050 Easton Village Dr, Easton, MD 21601

  Luxury resort-style living in the prestigious waterfront community of Easton Village! This spacious 4-bedroom, 3.5-bath home features a rare dual primary suite layout—with options on both the first and second floors—complemented by a $5,000 seller allowance to choose your own brand-new flooring.The light-filled interior has been freshly painted throughout and features a versatile

  

  Annie Witte Raymond

  Coldwell Banker Realty

  8050 Easton Village Dr, Easton, MD 21601
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  /15

  $359,990

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,600 Sq Ft

  1680 Lake Placid Dr, Trappe, MD 21673

  MOVE-IN-READY Home with Quartz Designer countertops and stainless steel appliances.

  

  Mrs. Terri E Hill

  Builder Solutions Realty

  1680 Lake Placid Dr, Trappe, MD 21673
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  /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 by award-winning firm - Pacquin Design Build, 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

  

  Gil Poudrier

  TTR Sotheby's International Realty

  0 Morgans Point Dr Unit MDTA2012638, Oxford, MD 21654
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  /18

  $784,990

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,690 Sq Ft

  Dover Plan at The Preserve at Wye Mills, Wye Mills, MD 21679

  Koch Homes Builder

  13505 Rustling Oaks Dr Unit 41012100, Wye Mills, MD 21679
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  /41

  $704,990

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 3,118 Sq Ft

  Greenbrier Plan at The Preserve at Wye Mills, Wye Mills, MD 21679

  Koch Homes Builder

  13505 Rustling Oaks Dr Unit 41012070, Wye Mills, MD 21679
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  /53

  $2,495,000

  • 3 Beds
  • 2.5 Baths
  • 2,472 Sq Ft

  26282 Deep Water Harbor Rd, Easton, MD 21601

  Tucked away on approximately 3 private acres along Plaindealing Creek just off the Tred Avon River, this striking waterfront retreat offers the perfect blend of Mid-Century Modern style, open-concept living, and exceptional Eastern Shore lifestyle amenities. With approximately 5’ MLW, a private dock with boat lift and floating dock, and sweeping water views from nearly every room, this property

  Chuck Mangold Benson & Mangold, LLC

  26282 Deep Water Harbor Rd, Easton, MD 21601
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  /32

  $1,049,000

  • 4 Beds
  • 3 Baths
  • 2,250 Sq Ft

  109 W Marengo St, Saint Michaels, MD 21663

  This thoughtfully designed 4-bedroom, 3-bathroom home features an open-concept floor plan ideal for both everyday living and entertaining. The main-level primary suite provides a private retreat with a spacious walk-in closet and an en-suite bath complete with a double vanity and glass-enclosed shower. The living room is anchored by a cozy gas fireplace and flows seamlessly into the dining area

  Chuck Mangold Benson & Mangold, LLC

  109 W Marengo St, Saint Michaels, MD 21663
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  /101

  $2,895,000

  • 4 Beds
  • 5 Baths
  • 3,589 Sq Ft

  4440 Baildon Rd, Trappe, MD 21673

  With sweeping sunset views, this picturesque estate—perfectly situation on a deepwater point with a private dock on Island Creek just off the Choptank River—offers the rare combination of privacy, acreage, and refined Eastern Shore living. Just ten minutes from Easton, Oxford, and Cambridge, the property features an impressive two‐story Tidewater Colonial of approximately 3,500± fsf that includes

  Janet Larson Benson & Mangold, LLC

  4440 Baildon Rd, Trappe, MD 21673
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  /16

  $689,990

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,685 Sq Ft

  Madison Plan at The Preserve at Wye Mills, Wye Mills, MD 21679

  Koch Homes Builder

  13505 Rustling Oaks Dr Unit 41012050, Wye Mills, MD 21679
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  /13

  $814,990

  New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,736 Sq Ft

  Brentwood Plan at The Preserve at Wye Mills, Wye Mills, MD 21679

  Koch Homes Builder

  13505 Rustling Oaks Dr Unit 41012111, Wye Mills, MD 21679
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  /63

  $9,900,000

  • 5 Beds
  • 6 Baths
  • 14,935 Sq Ft

  6010 Shipyard Ln, Easton, MD 21601

  Situated on one of the finest residential parcels in the country, Ship’s Point, is an estate with few rivals anywhere, at any price. The completely private 13+/- acre estate includes a deep water pier, and 270-degree views at the confluence of Trippe’s Creek and the Tred Avon River. The south-west facing manor house has been meticulously renovated by renowned builder Winchester Construction. A

  Chuck Mangold Benson & Mangold, LLC

  6010 Shipyard Ln, Easton, MD 21601
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  /41

  $3,495,000

  $300K PRICE DROP

  • 4 Beds
  • 5 Baths
  • 6,404 Sq Ft

  24678 New Post Rd, Saint Michaels, MD 21663

  Rare opportunity to acquire a well-appointed home with immense views and convenient proximity to St Michaels. Ideally located by land and sea in Chance Hope Farm on the Miles River at the confluence of Eastern Bay, this stunning, classic eastern shore brick colonial has everything the most decerning buyer needs. This Daffin custom-built home features a generous, main-level primary suite featuring

  Chuck Mangold Benson & Mangold, LLC

  24678 New Post Rd, Saint Michaels, MD 21663
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  /51

  $6,375,000

  • 2 Beds
  • 3 Baths
  • 2,388 Sq Ft

  0 Oxford Rd Unit MDTA2014582, Easton, MD 21601

  Duvall Farm is a rare Eastern Shore offering — a 408± acre farm that blends meaningful conservation efforts with immense easement potential, productive farmland, and refined residential improvements in a location between Easton and Oxford. Significant in both scale and character, the farm is comprised of 20 recorded parcels, presenting long-term value and a wide range of opportunities. The land

  Coard Benson Benson & Mangold, LLC

  0 Oxford Rd Unit MDTA2014582, Easton, MD 21601
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  /44

  $466,990

  New Construction

  • 5 Beds
  • 3 Baths
  • 2,511 Sq Ft

  HAYDEN Plan at Gannon Range, Easton, MD 21601

  The Hayden, a 2,511 square foot unique two-story home, offers five bedrooms, one located on the first floor, three full bathrooms, a flex room, a loft, and a two-car garage. The home’s welcoming foyer offers two coat closets and creates the perfect space to greet your guests. In the front of the home, the flex room with an abundance of natural light could be used as a home office or a den. Past

  D.R. Horton Builder

  8749 Harper Way Unit 36203248, Easton, MD 21601
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  /91

  $5,995,000

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

  27293 Southside Island Creek Rd, Trappe, MD 21673

  Wilderness Estate- This quintessential Eastern Shore farm is located along the Choptank River in Trappe, Maryland. Comprised of 47± acres, with original structures that are impeccably well-kept and improved with modern amenities, The Wilderness provides a unique opportunity to enjoy the best of the Eastern Shore. Surrounded by open space and preserved farmland with proximity to Oxford, Easton,

  Coard Benson Benson & Mangold, LLC

  27293 Southside Island Creek Rd, Trappe, MD 21673
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  /46

  $2,500,000

  • 5 Beds
  • 1 Bath

  4108 Saulsbury Ln, Trappe, MD 21673

  Discover one of Talbot Countys rare farms that combines productive farmland, waterfront, and exceptional recreational opportunities. This 105.72 acre agricultural property features approximately 80 acres of tillable ground and is well-suited for continued farming, income production, or long-term land investment. The open farmland is framed by wooded perimeter lines with a mixture of mature

  Casey Kennedy Whitetail Properties Real Estate

  4108 Saulsbury Ln, Trappe, MD 21673
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  /72

  $5,995,000

  • 8 Beds
  • 5.5 Baths
  • 9,051 Sq Ft

  8612 Tilghman Island Rd, Wittman, MD 21676

  See listing MDTA2012146 which includes an adjacent 37+-acre waterfront parcel which has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. "Bolton Farm", available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new

  Laura Carney TTR Sotheby's International Realty

  8612 Tilghman Island Rd, Wittman, MD 21676
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  /29

  $476,990

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,892 Sq Ft

  1553 Lake Tahoe Dr, Trappe, MD 21673

  Experience the epitome of modern living in the Matisse. This thoughtfully designed home offers main-level living at its finest, providing unparalleled comfort and flexibility to suit your unique lifestyle. The heart of the home is an open-concept haven, seamlessly blending a gourmet kitchen, dining room, and spacious family room. The kitchen, a chef's dream, features a functional island, abundant

  Brookfield Residential Builder

  1553 Lake Tahoe Dr, Trappe, MD 21673
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  /25

  $295,000

  Open Sat 10AM - 12PM

  • 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
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  /65

  $1,195,000

  $100K PRICE DROP

  • 5 Beds
  • 5.5 Baths
  • 3,574 Sq Ft

  110 N Morris St, Oxford, MD 21654

  Incredible opportunity to own a circa 1875 home in Oxford's Historic District that has been renovated with a separate 2 bedroom apartment with views of Town Creek. Formerly a Bed and Breakfast, it features 2 first floor bedrooms with 1 and 1/2 baths and 3 second floor bedrooms each with its own full bath. Entire exterior has been newly painted and most of the windows have been replaced. A lovely

  Henry Hale Benson & Mangold, LLC

  110 N Morris St, Oxford, MD 21654
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  /87

  $5,000,000

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

  5499 Anderby Hall Rd, Royal Oak, MD 21662

  Now offered at an improved price of $5,000,000. Excellent opportunity to own your own private Eastern Shore estate in Royal Oak. Anderby Hall, part of an original 1680 land grant, spans a breathtaking 12+/- acre parcel featuring 3,260’+/- of rip-rapped shoreline. This exceptional property includes a tidal pond, a private cove, and an exclusive island peninsula accessed by bridge. Pass through the

  Valerie Brown Coldwell Banker Realty

  5499 Anderby Hall Rd, Royal Oak, MD 21662
• 

  

  /97

  $7,950,000

  $450K PRICE DROP

  • 7 Beds
  • 9 Baths
  • 8,001 Sq Ft

  26546 Presquile Dr N, Easton, MD 21601

  Presquile Manor House, originally built by the Lloyd Family circa 1800 as one of their three Plantation Houses, sits up high on the Wye River with due West Exposure. The Main House has recently gone through a two-year renovation process from top to bottom by West & Callahan Construction and Peter Zimmerman Architects Inc, with much thought and care to keep all of the historic attributes that this

  Henry Gibbons-Neff Meredith Fine Properties

  26546 Presquile Dr N, Easton, MD 21601

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