Talbot County MD Houses for Sale

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  /26

  $574,900

  • 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

  (443) 332-7340

  10490 Longwoods Rd, Easton, MD 21601
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  /25

  $439,900

  • 3 Beds
  • 2.5 Baths
  • 1,780 Sq Ft

  206 South St, Easton, MD 21601

  Beautifully renovated and ideally located in downtown Easton, this 3-bedroom, 2.5-bath home offers the perfect blend of historic charm and modern updates, all within close proximity to the town’s best shops, restaurants, galleries, theaters, and parks. Inside, the home features an open and functional floor plan centered around a renovated kitchen, ideal for both everyday living and entertaining.

  

  Brian Gearhart

  Benson & Mangold, LLC

  (443) 464-2789

  206 South St, Easton, MD 21601
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  /27

  $949,000

  • 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

  (410) 593-1432

  28715 Jacks Field Rd, Wye Mills, MD 21679
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  /64

  $1,199,000

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

  6670 Tilghman Island Rd, Sherwood, MD 21665

  New Price! Waterfront home situated on Back Creek in Sherwood, offering direct access to the Chesapeake Bay and Choptank Rivers. 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

  (410) 881-8730

  6670 Tilghman Island Rd, Sherwood, MD 21665
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  /75

  $569,000

  • 5 Beds
  • 3.5 Baths
  • 3,404 Sq Ft

  5559 Trafalgar Cir, Tilghman, MD 21671

  TILGHMAN ISLAND.Welcome to this beautiful and spacious 5-bedroom, 3.5-bath single-family home located in the highly sought-after Tilghman on Chesapeake community. Designed for modern comfort and relaxed island living, this home offers an open-concept floor plan filled with abundant natural light and elegant finishes throughout. The gourmet kitchen is a true centerpiece, featuring granite

  

  John McGlannan

  Meredith Fine Properties

  (410) 834-0959

  5559 Trafalgar Cir, Tilghman, MD 21671
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  /76

  $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

  (410) 650-6320

  11778 Old Skipton Rd, Cordova, MD 21625
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  /144

  $1,795,000

  • 4 Beds
  • 3.5 Baths
  • 3,575 Sq Ft

  216 E Chew Ave, Saint Michaels, MD 21663

  Don't miss this rare opportunity. This special home offers spectacular and picturesque views of the Saint Michaels Harbor in addition to its prime location on one of Saint Michaels most desirable streets. Conveniently located near all of the in-town amenities and walkable to great restaurants, shops, brewery, winery, gallery, seasonal farmer's market, museums and more. This home has received a

  

  Christopher Clinton

  Coldwell Banker Chesapeake Real Estate Company

  (855) 940-3395

  216 E Chew Ave, Saint Michaels, MD 21663
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  /50

  $779,900

  • 4 Beds
  • 2.5 Baths
  • 2,800 Sq Ft

  28309 Village Lake Way, Easton, MD 21601

  Reduced Price! Beautifully maintained 4-bedroom, 2.5 bath home in the highly desirable Easton Village community, offering a perfect blend of traditional style, modern comfort, and timeless charm. Step into a bright 2-story foyer with newly installed luxury vinyl plank (LVP) flooring that continues throughout much of the home. On either side, the formal living and dining rooms provide elegant

  

  Lori Woods-Fortney

  Berkshire Hathaway HomeServices Homesale Realty

  (410) 517-7606

  28309 Village Lake Way, Easton, MD 21601
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  /19

  $349,990 New Construction

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

  1686 Lake Placid Dr, Trappe, MD 21673

  This new two-story home features a bright and open first floor, where the kitchen, living, and dining areas flow seamlessly to create a flexible, spacious environment. Upstairs, two bedrooms and a luxurious owner’s suite are arranged around a versatile loft, perfect for work, study, or relaxation. The home is finished with a convenient two-car garage.

  

  Terri Hill

  Builder Solutions Realty

  1686 Lake Placid Dr, Trappe, MD 21673
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  /72

  $599,000

  • 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 affordable. Escape the city / suburbs and spend your weekends in the quintessential Eastern Shore town of St. Michaels, known for its picturesque streets, quaint shops, vibrant dining scene, wineries, and distilleries. This charming waterfront community has everything you need to relax, recharge, and truly enjoy life on Maryland’s Eastern Shore -

  

  Gretchen Wichlinski

  Compass

  (844) 461-3815

  204 E Marengo St, Saint Michaels, MD 21663
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  /72

  $759,000

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

  6660 Reeses Pride Rd, Sherwood, MD 21665

  Your Eastern Shore paradise awaits! This awesomely updated, meticulously maintained, classic colonial-style home is like a breath of fresh air. Located on a full 2 acre parcel, in the heart of the sought after Deep Harbour Farm community, custom features include a lovely private backyard oasis, designed around an 18’x32’ inground salt-water pool, and surrounded by all new, high-quality fencing,

  

  John McGlannan

  Meredith Fine Properties

  (410) 431-3957

  6660 Reeses Pride Rd, Sherwood, MD 21665
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  /61

  $469,000

  • 2 Beds
  • 2 Baths
  • 1,878 Sq Ft

  29580 Kent Ave, Easton, MD 21601

  Welcome to this beautifully appointed 2 bedroom, 2 bathroom single-level home in the sought-after Easton Club East community, offering natural light throughout. A welcoming foyer sets the tone, with an office/library on the right and dining room on the left, and the living room straight ahead, which impresses with a tray ceiling, crown molding, and classic wainscoting, creating an ideal space for

  

  Dustin Oldfather

  Compass

  (443) 363-5004

  29580 Kent Ave, Easton, MD 21601
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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

  (667) 242-9472

  5933 Tilghman Island Rd, Tilghman, MD 21671
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  /65

  $799,000 Open Sun 12PM - 2PM

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

  8050 Easton Village Dr, Easton, MD 21601

  Now Priced to reflect exceptional value in Easton Village This beautifully appointed Custom built four-bedroom, three-and-a-half bath home offers refined comfort and effortless Eastern Shore living in one of Easton’s most sought-after waterfront access communities. Built in 2014 and thoughtfully designed for today’s lifestyle, the kitchen features quartz countertops, abundant cabinetry, and

  

  Annie Witte Raymond

  Coldwell Banker Realty

  (443) 331-9589

  8050 Easton Village Dr, Easton, MD 21601
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  /10

  $374,990 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,170 Sq Ft

  1233 Lake Meade Dr, Trappe, MD 21673

  Quick move-in 4-bedroom, 3.5-bath home with a nice yard, great schools, and plenty of space for a family.

  

  Terri Hill

  Builder Solutions Realty

  (443) 249-9269

  1233 Lake Meade 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

  (410) 883-9692

  0 Morgans Point Dr Unit MDTA2012638, Oxford, MD 21654
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  /23

  $439,990 New Construction

  • 3 Beds
  • 1 Bath
  • 1,841 Sq Ft

  Matisse Plan at Lakeside at Trappe - Single Family Homes Collection, 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

  1254 Lake Michigan Unit 36578892, Trappe, MD 21673
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  /23

  $369,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,676 Sq Ft

  Alan Plan at Lakeside at Trappe - Signature, Trappe, MD 21673

  Designed for low-maintenance living, this new single-family home features a convenient, open-concept layout. Two secondary bedrooms frame the foyer to provide peaceful retreats, while down the hallway is the main living area. It showcases a fully equipped kitchen, dining room and a spacious Great Room with direct access to the backyard. In a corner is the owner’s suite with an attached bathroom

  Lennar Builder

  1258 Lake Michigan Unit 36949654, Trappe, MD 21673
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  /52

  $12,500,000

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

  6150 Oxford Rd, Easton, MD 21601

  Duvall Farm is a rare Eastern Shore offering — a 525± 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 30 recorded parcels, presenting long-term value and a wide range of opportunities. The land

  Coard Benson Benson & Mangold, LLC

  6150 Oxford Rd, Easton, MD 21601
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  /71

  $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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  /28

  $464,990 New Construction

  • 4 Beds
  • 1.5 Baths
  • 2,340 Sq Ft

  Torrington Plan at Lakeside at Trappe - Single Family Homes Collection, Trappe, MD 21673

  Step into refined living with The Torrington – an impeccably designed 2-level residence that seamlessly marries sophistication with functionality. A covered porch extends a gracious welcome. Upon entering is a living room that can be converted into a library or playroom to meet your needs. The heart of this residence lies in its open-concept kitchen, harmoniously connecting the dining room and

  Brookfield Residential Builder

  1254 Lake Michigan Unit 36578895, Trappe, MD 21673
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  /22

  $399,990 New Construction

  • 2 Beds
  • 1 Bath
  • 1,311 Sq Ft

  Douglas Plan at Lakeside at Trappe - Single Family Homes Collection, Trappe, MD 21673

  The Douglas offers an open concept and the convininece of main level living. The heart of the home is the stunning chef's kitchen, featuring Carrara Morro quartz countertops, and conveniently positioned between the dining room and cozy living room, fostering seamless flow for gatherings. 10' ceilings on the main level amplify the spaciousness of the home. A sliding door in the family room opens

  Brookfield Residential Builder

  1254 Lake Michigan Unit 36578897, Trappe, MD 21673
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  /27

  $514,990 New Construction

  • 4 Beds
  • 1.5 Baths
  • 3,241 Sq Ft

  Beckham Plan at Lakeside at Trappe - Single Family Homes Collection, Trappe, MD 21673

  Step into the two-story foyer of the Beckham and you’ll feel the unmatched luxury and comfort. The open floorplan creates an atmosphere that is both impressive and inviting. Use the library to work from home and be tucked away in the back of the home or choose to turn this into a main level guest suite. A large gourmet kitchen with center island and pantry are a chef’s delight and flow into the

  Brookfield Residential Builder

  1254 Lake Michigan Unit 36578896, Trappe, MD 21673
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  /80

  $1,250,000

  • 4 Beds
  • 3.5 Baths
  • 4,443 Sq Ft

  28028 Playtor Rd, Easton, MD 21601

  Welcome to this exceptional William Poole–designed Tidewater Colonial, gracefully sited on approximately 2.3 acres in the desirable community of Waverly Island Estates, just three miles from the Town of Easton. Offering a refined blend of classic coastal architecture and modern comfort, this property provides a private retreat on Maryland’s Eastern Shore. Inside, the home features a well-designed

  Coard Benson Benson & Mangold, LLC

  28028 Playtor Rd, Easton, MD 21601
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  /44

  $458,990 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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  /29

  Call for Price

  • 3 Beds
  • 2 Baths
  • 1,358 Sq Ft

  29181 Pin Oak Way, Easton, MD 21601

  Spacious 3 bedroom / 2 bath Rambler located in the convenient community of South Beechwood! Updated kitchen overlooks the large family room with small bar area, gas stove fireplace insert. Separate formal Living Room and Dining Room. Most rooms with new all new flooring Nice level lot with a fenced rear yard, fantastic maintenance free rear deck for outdoor entertaining! Attached garage with work

  Vincent Payne Realty Navigator

  29181 Pin Oak Way, Easton, MD 21601
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  /36

  $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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  /57

  $1,900,000

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

  3750 Windy Hill Rd, Trappe, MD 21673

  This 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 offers a balanced mix of tillable acreage, improved structures, and wildlife

  Casey Kennedy Whitetail Properties Real Estate

  3750 Windy Hill Rd, Trappe, MD 21673
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  /65

  $1,295,000

  • 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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  /52

  $849,900

  • 3 Beds
  • 2.5 Baths
  • 2,882 Sq Ft

  8006 Parrotts Lot Cir, Easton, MD 21601

  Perfectly positioned on a premier corner lot overlooking a tranquil park-like circle, ( Hollyday Park), this thoughtfully designed home blends refined finishes with effortless functionality. Framed by a welcoming front porch and complemented by a private side porch just off the sunlit Morning Room, this distinguished home captures the essence of relaxed coastal elegance.This 3 Bedroom 2-1/2

  Stephany Barrett Long & Foster Real Estate, Inc.

  8006 Parrotts Lot Cir, Easton, MD 21601
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  /38

  $729,900

  • 5 Beds
  • 4 Baths
  • 3,328 Sq Ft

  9629 Bantry Rd, Easton, MD 21601

  Located in the desirable Bantry Community, this classic colonial sits on a 5± acre lot and offers a spacious, well-designed layout ideal for everyday living and entertaining. The home features five bedrooms, along with two full and two half baths. The main level offers hardwood flooring throughout most of the space, a formal dining room, and multiple inviting living areas highlighted by two

  Chuck Mangold Benson & Mangold, LLC

  9629 Bantry Rd, Easton, MD 21601
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  /64

  $739,000

  • 4 Beds
  • 2.5 Baths
  • 2,798 Sq Ft

  24965 Back Creek Dr, Saint Michaels, MD 21663

  Tucked into the heart of Back Creek Landing, this home offers the kind of layout and setting that just works—comfortable, well thought out, and connected to both nature and town. The main living space is designed around how people actually live. The kitchen is open and inviting, with a bright eat-in area and an elevated counter with seating—perfect for morning coffee, casual meals, or simply

  Kathleen Coale Benson & Mangold, LLC

  24965 Back Creek Dr, Saint Michaels, MD 21663
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  /73

  $1,350,000

  • 4 Beds
  • 4.5 Baths
  • 3,528 Sq Ft

  114 W Chestnut St, St. Michaels, MD 21663

  Ideally located in the heart of the St. Michaels Historic District, this beautifully maintained three-story home offers exceptional walkability just a half block from the waterfront, scenic walking trail, public park and kayak launch, as well as the shops, restaurants, and other amenities that make St. Michaels such a sought-after place to live. A welcoming front porch introduces an inviting

  Wink Cowee Benson & Mangold, LLC

  114 W Chestnut St, St. Michaels, MD 21663
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  /39

  $1,325,000

  • 2 Beds
  • 2.5 Baths
  • 2,282 Sq Ft

  106 E Chestnut St, Saint Michaels, MD 21663

  Luxury Restoration in the Heart of Historic St. Michaels Welcome to 106 E. Chestnut Street, where historic charm and modern luxury come together in one of the Eastern Shore’s most beloved waterfront towns. Completely renovated down to the studs, this exceptional home has been thoughtfully reimagined to preserve its classic character while introducing high-end systems, refined finishes, and modern

  Justin Pokrywka Taylor Properties

  106 E Chestnut St, Saint Michaels, MD 21663
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  /25

  $799,000 New Construction

  • 4 Beds
  • 2.5 Baths

  Lot 16A Meadow St, Saint Michaels, MD 21163

  Welcome to the quaint town of St. Michaels. Waterfront dining, history and small town feel are combined to give you a perfect home for full time or vacation home.Lacrosse homes is proud to present The Pointe.Time to make your personal selections. Make this home your personal statement.Pick the exterior colors, interior feature such as flooring, cabinets, countertops and more.Make this

  George Bailey Keller Williams Flagship

  Lot 16A Meadow St, Saint Michaels, MD 21163
• 

  /2

  $1,095,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,780 Sq Ft

  0 Hope Cir, Easton, MD 21601

  Welcome to your future home in Cooke’s Hope, one of the Eastern Shore’s most desirable communities, ideally located along the scenic Oxford corridor. This to-be-built coastal style home will offer 3 to 4 bedrooms, 2.5 baths, and a spacious two-car attached garage. Built with high-quality materials the home will also include a conditioned crawlspace, brick veneer foundation, Hardie Plank siding,

  Chuck Mangold Benson & Mangold, LLC

  0 Hope Cir, Easton, MD 21601
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  /54

  $655,000 Open Sat 11AM - 1PM

  • 4 Beds
  • 5 Baths
  • 2,454 Sq Ft

  18 Londonderry Dr, Easton, MD 21601

  This charming Colonial home in the desirable Thread Haven community offers a perfect blend of comfort and style. With 2954sq. ft. (including the 2-car garage) of well-designed space, it features 4 spacious bedrooms and 2 full 2 half baths. The gourmet kitchen, complete with an island and modern appliances, is perfect for culinary enthusiasts. Enjoy cozy evenings by the gas fireplace in the

  James Campbell Benson & Mangold, LLC

  18 Londonderry Dr, Easton, MD 21601
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  /55

  $725,000

  • 3 Beds
  • 3 Baths
  • 2,103 Sq Ft

  28540 Holden Rd, Easton, MD 21601

  Just five minutes from downtown Easton, this beautifully maintained one-level home offers the perfect blend of comfort, style, and easy Eastern Shore living. With peaceful water views of Peachblossom Creek and access to a community landing for effortless kayak launching, this property truly embraces its setting.Inside, gleaming black walnut floors create a seamless flow from the spacious

  Shelley Baden Berkshire Hathaway HomeServices PenFed Realty

  28540 Holden Rd, Easton, MD 21601
• 

  

  /6

  $659,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,606 Sq Ft

  13 Sandy Ln, Easton, MD 21601

  The one-of-a-kind Ryan model is set to be the largest one-story home constructed on Sandy Lane, brought to life by Developer Sandy Lane, LLC and renowned local builders Stansbury and Sons. Like all ten homes in this thoughtfully designed new downtown Easton community, the Ryan will be a custom, stick-built residence backed by a one-year builder’s warranty and outfitted with brand-new appliances

  Janet Larson Benson & Mangold, LLC

  13 Sandy Ln, Easton, MD 21601
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  /45

  $719,500

  • 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

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