Talbot County MD Homes for Sale

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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 on 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. Offered fully furnished, the home provides a truly turnkey opportunity,

  

  Brian Gearhart

  Benson & Mangold, LLC

  5698 Leeward Ln, Tilghman, MD 21671
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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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  /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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  /25

  $419,000

  $21K PRICE DROP

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

  206 South St, Easton, MD 21601

  **House was under contract with a home sale contingency** 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

  

  Brian Gearhart

  Benson & Mangold, LLC

  206 South St, Easton, MD 21601
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  /31

  $375,000

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

  24362 Widgeon Place Unit 5, Saint Michaels, MD 21663

  Tucked away in the quiet Widgeon Place community, this meticulously maintained 2-bedroom, 2.5-bath townhome offers comfort, privacy, and inviting living spaces throughout. The galley kitchen features a charming breakfast nook and flows into the dining and living area, highlighted by a wood-burning fireplace. Just beyond, a cozy sitting area opens to a brick patio overlooking a lovely backyard

  

  Tracy Higgs-Wagner

  Meredith Fine Properties

  24362 Widgeon Place Unit 5, Saint Michaels, MD 21663
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  /10

  $72,500

  $8K PRICE DROP

  • Land
  • 13,068 Sq Ft
  • $241,667 per Acre

  21472 Willey Rd, Tilghman, MD 21671

  Tilghman Island. Clear level building lot with public sewer available. The perfect spot for your new vacation / retirement home. Excellent opportunity to make your island dream come true.

  

  John McGlannan

  Meredith Fine Properties

  21472 Willey Rd, Tilghman, MD 21671
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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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  /6

  $800,000

  $95K PRICE DROP

  • Land
  • 2 Acres
  • $400,000 per Acre

  0 I Way Court Lot #9 Unit MDTA2013178, Easton, MD 21601

  A prime commercial opportunity awaits at Easton Technology Park. This fully cleared 2-acre lot comes with all utilities — water, sewer, electric, and gas — already brought to the curb, making it truly move-in ready for your business. Zoned BC (Business Commercial), the property offers exceptional visibility and accessibility with direct access from Route 50. Situated directly across from Easton

  

  Tracy Higgs-Wagner

  Meredith Fine Properties

  0 I Way Court Lot #9 Unit MDTA2013178, Easton, MD 21601
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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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  /45

  $323,000

  $12K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,360 Sq Ft

  7407 Tour Dr, Easton, MD 21601

  Step inside to an inviting open-concept main level, where a spacious great room flowsseamlessly to a 15' deck overlooking two serene ponds and wooded views—a rare backdropthat makes everyday living feel like a retreat.Upstairs, you’ll find two private primary suites, each with its own full bath, walk-in closet, andgleaming hardwood floors. The rear suite offers especially stunning

  

  John McGlannan

  Meredith Fine Properties

  7407 Tour Dr, Easton, MD 21601
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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,

  

  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

  Covell custom built home, featuring 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 cash bonus flooring design credit.The light-filled interior has been freshly painted throughout and features a

  

  Annie Witte Raymond

  Coldwell Banker Realty

  8050 Easton Village 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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  /37

  $370,000

  $10K PRICE DROP

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

  408 Crowberry Cir, Easton, MD 21601

  Welcome to 408 Crowberry Circle, where convenience, comfort, and exceptional value come together in one of Easton's most desirable communities. Offering nearly 1,900 square feet of living space, this beautifully maintained end-unit townhome delivers outstanding value with the space and features today's buyers are searching for. Featuring 3 bedrooms, 2.5 bathrooms, a two-car garage, and a

  

  Brian Gearhart

  Benson & Mangold, LLC

  408 Crowberry Cir, Easton, MD 21601
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  /10

  $68,500

  $7K PRICE DROP

  • Land
  • 13,068 Sq Ft
  • $228,333 per Acre

  0 Sinclair Ave, Tilghman Island, MD 21671

  Build your dream home on beautiful Tilghman Island! This ideally located lot is within walkingdistance of Sinclair Community Park, local marinas, charming shops, and popular waterfrontrestaurants. Stroll to the end of your street to enjoy stunning Chesapeake Bay sunsets from thepark’s scenic shoreline.Tilghman Island is a beloved Eastern Shore destination known for its rich

  

  John McGlannan

  Meredith Fine Properties

  0 Sinclair Ave, Tilghman Island, MD 21671
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  /6

  $900,000

  $95K PRICE DROP

  • Land
  • 2.18 Acres
  • $412,844 per Acre

  0 I-Way Court Lot #10, Easton, MD 21601

  A prime commercial opportunity awaits at Easton Technology Park. This fully cleared 2.185-acre lot comes with all utilities — water, sewer, electric, and gas — already brought to the curb, making it truly move-in ready for your business. Zoned BC (Business Commercial), the property offers exceptional visibility and accessibility with direct access from Route 50. Situated directly across from

  

  Tracy Higgs-Wagner

  Meredith Fine Properties

  0 I-Way Court Lot #10, Easton, MD 21601
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  /75

  $550,000

  $19K 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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  /29

  $359,000

  $16K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,487 Sq Ft

  24700 Deepwater Unit 23, Saint Michaels, MD 21663

  Escape to the sought-after Swan Road Villa Townhomes, where low-maintenance living meets comfort, convenience, and lifestyle. This bright and inviting reverse-living townhome offers 2 bedrooms, 2.5 baths, and a thoughtfully designed floor plan that appeals to both full-time residents and weekend retreat seekers alike. The upper level serves as the heart of the home, featuring an open-concept

  

  Tracy Higgs-Wagner

  Meredith Fine Properties

  24700 Deepwater Unit 23, Saint Michaels, MD 21663
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  /39

  $795,000

  $54K PRICE DROP

  • 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

  

  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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  /2

  $599,000

  • Land
  • 19.82 Acres
  • $30,222 per Acre

  26383 Royal Oak Rd, Easton, MD 21601

  Discover the perfect blend of privacy, space, and location with this exceptional 20± acre parcel ideally situated between Easton and St. Michaels. Offering a peaceful rural setting while remaining just minutes from shopping, dining, and waterfront attractions, this property presents a rare opportunity to build your dream home or invest in future development potential. With approximately 20 acres

  

  BJ Kilby

  Eastern Shore Real Estate, LLC

  26383 Royal Oak Rd, 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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  /19

  $334,290

  New Construction $45K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,254 Sq Ft

  1217 Loch Ness Ln, Trappe, MD 21673

  Large 3 bed Townhouse 2,254 sq ft - July Delivery! Open plan kitchen, Stainless steel appliances. Photos are for illustration purposes. Agents must accompany buyer during first visit to the community.

  

  Mrs. Terri E Hill

  Builder Solutions Realty

  1217 Loch Ness Ln, Trappe, MD 21673
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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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  /25

  $599,900

  $40K PRICE DROP

  • 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
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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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  /32

  $739,900

  $39K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,531 Sq Ft

  28816 Jasper Ln, Easton, MD 21601

  Welcome to 28816 Jasper Lane in the highly sought-after Cooke’s Hope community. This beautifullymaintained end-unit townhome offers 4 bedrooms and 2.5 baths, including a convenient main-level primary suite complete with a walk-in closet and relaxing soaking tub. The light-filled living roomfeatures a dramatic vaulted ceiling and cozy gas fireplace, creating the perfect space to unwind

  Chuck Mangold Benson & Mangold, LLC

  28816 Jasper Ln, Easton, MD 21601
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  /20

  $359,900

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

  9531 Quail Hollow Dr Unit 402, Saint Michaels, MD 21663

  Located in the desirable Martingham community, this two-bedroom, two-and-a-half-bath condominium offers comfortable living just minutes from historic downtown St. Michaels. The main level features a spacious living room with hardwood flooring and a wood-burning fireplace, a convenient half bath, and a full-season sunroom overlooking the backyard with direct access to the outdoor space. A detached

  Chuck Mangold Benson & Mangold, LLC

  9531 Quail Hollow Dr Unit 402, Saint Michaels, MD 21663
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  /51

  $6,375,000

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

  6150 Oxford Rd, 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

  6150 Oxford Rd, 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

  D.R. Horton Builder

  8749 Harper Way Unit 36203248, Easton, MD 21601
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /46

  $469,000

  • 3 Beds
  • 2 Baths
  • 1,916 Sq Ft

  29786 Standish St, Easton, MD 21601

  Well-maintained 3 bedroom 2 bathroom rancher in the desirable Matthewstown Run community offering comfortable one-level living on a spacious corner lot. Inside, you'll find engineered hardwood floors, granite countertops, and a bright sunroom with sliding doors and plenty of natural light, making it a great space to relax or entertain. The large primary suite features a walk-in closet and a

  Jason French Benson & Mangold, LLC

  29786 Standish St, Easton, MD 21601

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