Talbot County MD Homes for Sale

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  /54

  $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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  /57

  $1,650,000

  $75K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 3,078 Sq Ft

  602 Landing Rd, Saint Michaels, MD 21663

  Welcome to waterfront living in the heart of St. Michaels. This fully renovated 3-bedroom plus office, 2.5-bath home offers a thoughtful blend of modern updates and coastal charm, all set against expansive views of the Miles River. The first-floor primary suite is a true retreat, featuring a custom California Closet system and a beautifully updated bath with a walk-in shower, freestanding tub,

  

  Brian Gearhart

  Benson & Mangold, LLC

  602 Landing Rd, Saint Michaels, MD 21663
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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

  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

  206 South St, 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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  /29

  $365,000

  $10K 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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  /144

  $1,595,000

  $200K PRICE DROP

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

  216 E Chew Ave, Saint Michaels, MD 21663

  PRICE REDUCED: 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

  

  Christopher Clinton

  Coldwell Banker Chesapeake Real Estate Company

  216 E Chew Ave, Saint Michaels, MD 21663
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  /45

  $975,000

  $80K PRICE INCREASE Coming Soon

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

  4938 Fairbank Rd, Tilghman, MD 21671

  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 cottage, complete with

  

  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

  $379,000

  $11K 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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  /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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  /72

  $749,000

  • 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

  6660 Reeses Pride Rd, Sherwood, MD 21665
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  /6

  $845,000

  $50K PRICE DROP

  • Land
  • 2 Acres
  • $422,500 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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  /45

  $328,000

  $7K 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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  /7

  $1,250,000

  • Land
  • 47.52 Acres
  • $26,305 per Acre

  0 Unionville Rd Unit MDTA2008824, Easton, MD 21601

  Presenting 47+ acres of stunning land just minutes from Easton, perfectly positioned at the intersectionof Unionville Road and Miles River Road, extending along Anchorage Road. This expansive property iscurrently leased for farming and hunting, offering both income potential and recreational opportunities.While it has not been perc tested, the property holds potential for multiple

  

  Tracy Higgs-Wagner

  Meredith Fine Properties

  0 Unionville Rd Unit MDTA2008824, Easton, MD 21601
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  /72

  $574,999

  • 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 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, and enjoy a

  

  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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  /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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  /5

  $2,250,000

  • Land
  • 4.18 Acres
  • $538,278 per Acre

  0 Morgans Point Dr Unit MDTA2012470, Oxford, MD 21654

  Discover the rare opportunity to own one of the Eastern Shore's finest waterfront parcels: Lot 5, an exceptional 4.18-acre homesite in the exclusive Morgan's Point community of Oxford, Maryland. This home site has an approved prec, and flood insurance is not required. Tucked along the serene Tred Avon River, this buildable waterfront gem offers expansive privacy and boundless potential, thanks to

  

  Gil Poudrier

  TTR Sotheby's International Realty

  0 Morgans Point Dr Unit MDTA2012470, Oxford, MD 21654
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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

  $75,000

  • Land
  • 13,068 Sq Ft
  • $250,000 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

  $945,000

  $50K PRICE DROP

  • Land
  • 2.18 Acres
  • $433,486 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

  $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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  /27

  $1,795,000

  • Land
  • 20 Acres
  • $89,750 per Acre

  0 St Michaels Rd Unit MDTA2012442, Newcomb, MD 21653

  20 acres off St Michaels Rd overlooking Newcomb Creek and out to the Miles River. Partially cleared shoreline offering expansive views of the water with beautiful sandy beaches and high elevation. During the summer, enjoy a quick boat ride to St. Michaels and all that the town has to offer. In the fall and winter, enjoy great goose and duck hunting. Approved for 6 bedroom SDA.

  

  Brian Gearhart

  Benson & Mangold, LLC

  0 St Michaels Rd Unit MDTA2012442, Newcomb, MD 21653
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  /18

  $324,990

  New Construction

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

  1410 Lake Geneva Dr, Trappe, MD 21673

  August Delivery! Discover the Elmwood, a luxury three-story townhome offering 2,254 square feet of thoughtfully designed living space in Lakeside at Trappe. This move-in ready home features 3 bedrooms, 2.5 baths, and a 2-car garage with a private driveway. The entry level includes a spacious recreation room with direct access to the outdoor patio, providing the perfect space for entertaining or

  

  Terri Hill

  Builder Solutions Realty

  1410 Lake Geneva 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
• 

  

  /18

  $328,940

  New Construction Open Sat 11AM - 3PM

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

  1416 Lake Geneva Dr, Trappe, MD 21673

  Backing to open space for added privacy, this beautiful new construction townhome offers the perfect blend of comfort, style, and convenience. Residents enjoy exceptional community amenities, including a clubhouse, resort-style swimming pool, fitness center, walking and biking trails, playground/tot lot, pickleball and multi-sport courts, dog park, and a scenic lake woven throughout the

  

  Terri Hill

  Builder Solutions Realty

  1416 Lake Geneva Dr, Trappe, MD 21673
• 

  

  /18

  $403,540

  New Construction Open Sat 11AM - 3PM

  • 5 Beds
  • 2 Baths
  • 2,238 Sq Ft

  1467 Lake George Ln, Trappe, MD 21673

  The Richmond by Lennar is a popular new construction home on Maryland’s Eastern Shore, offering approximately 2,238 square feet of thoughtfully designed living space. This spacious floor plan features 5 bedrooms and 3 full bathrooms, providing plenty of room for family, guests, or a home office. The open-concept layout showcases a large kitchen and dining area, highlighted by elegant quartz

  

  Terri Hill

  Builder Solutions Realty

  1467 Lake George Ln, Trappe, MD 21673
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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.

  

  Terri Hill

  Builder Solutions Realty

  1680 Lake Placid Dr, Trappe, MD 21673
• 

  

  /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.

  

  Terri Hill

  Builder Solutions Realty

  1217 Loch Ness Ln, 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
• 

  

  /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
• 

  

  /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
• 

  

  /25

  $639,900

  • 3 Beds
  • 3 Baths
  • 1,986 Sq Ft

  4794 Sailors Ln, Oxford, MD 21654

  Nestled on 2± acres, this inviting property offers a peaceful setting surrounded by mature trees that provide shade and natural beauty throughout the seasons. A circular driveway creates a welcoming approach and allows for easy access to the home and detached two-car garage, which also offers excellent potential as a workshop, studio, or hobby space. Inside, hardwood flooring extends throughout

  Chuck Mangold Benson & Mangold, LLC

  4794 Sailors Ln, Oxford, MD 21654
• 

  

  /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
• 

  

  /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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