Talbot County MD Homes for Sale

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  /38

  $2,250,000

  • 3 Beds
  • 2.5 Baths
  • 2,284 Sq Ft

  222 E Chestnut St, Saint Michaels, MD 21663

  A unique opportunity to own a completely renovated home in the heart of town featuring four deep-water, dedicated boat slips. Located at the end of one of the most coveted, tree-lined streets in St. Michaels, this home is surrounded by beautifully restored historic properties and offers incredible views of St. Michaels Harbor. The current owners have thoughtfully renovated this 3-bedroom,

  

  Brian Gearhart

  Benson & Mangold, LLC

  (844) 651-2546

  222 E Chestnut St, Saint Michaels, MD 21663
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  /44

  $1,895,000

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

  6119 Country Club Dr, Easton, MD 21601

  Location, Location, Location!!! This recently renovated waterfront rancher on a 2+ acre, park-like lot is conveniently located next to Talbot Country Club, and off the Oxford Road corridor. This home features 3 bedrooms, 2 full and 2 - 1/2 baths, a large living room with fireplace, kitchen/family room combo with the kitchen featuring quartz counter tops, stainless steel appliances and custom

  

  Brian Gearhart

  Benson & Mangold, LLC

  (410) 941-0437

  6119 Country Club Dr, Easton, MD 21601
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  /23

  $2,900,000

  • 3 Beds
  • 3 Baths
  • 1,973 Sq Ft

  26396 St Michaels Rd, Newcomb, MD 21653

  Generational Waterfront Farm. Magnificent Building site on the Miles River on 50+ acres. Private tree-lined driveway passing through productive fields, mature evergreen and deciduous trees. There is a brick cape cod on the property and an outbuilding that should be considered a footprint for future development. Existing well, pier and bulkhead area on the cove (Newcomb Creek). Over 1500 of

  

  Brian Gearhart

  Benson & Mangold, LLC

  (410) 618-4530

  26396 St Michaels Rd, Newcomb, MD 21653
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  /41

  $450,000

  • 3 Beds
  • 2.5 Baths
  • 1,512 Sq Ft

  5744 Johns Way, Tilghman, MD 21671

  2 year old cottage located on Tilghman Island. 3 bedrooms and 2.5 baths, this property is perfect for full time residents or for weekend getaways. Property is located on a quite cul-de-sac and backs up to trees. Large open living room, dining area and kitchen provides enough space for family gatherings or entertaining friends. Kitchen has granite counters and stainless appliances along with a

  Rebecca Biggs

  Tilghman Island Realty Inc

  (667) 245-9539

  5744 Johns Way, Tilghman, MD 21671
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  /31

  $469,000

  • 4 Beds
  • 2.5 Baths
  • 2,277 Sq Ft

  8388 Colony Cir, Easton, MD 21601

  Welcome to 8388 Colony Circle, a charming Juniper model offering 4 bedrooms, 2.5 bathrooms, and timeless traditional style just minutes from downtown Easton. This well maintained two-story home features a new roof, hardwood floors throughout the main level, a cozy fireplace, and custom built-ins that add warmth and character to the living space. The eat-in kitchen flows seamlessly into a spacious

  

  Brian Gearhart

  Benson & Mangold, LLC

  (443) 733-4941

  8388 Colony Cir, Easton, MD 21601
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  /17

  $349,900

  • 3 Beds
  • 2 Baths
  • 1,259 Sq Ft

  106 Sycamore Ave, Easton, MD 21601

  Recently renovated rancher located in close proximity to downtown Easton. This 3-bedroom, 2-bath home offers a bright and open floor plan with fresh paint, new flooring throughout, new washer and dryer and both bathrooms updated. The layout includes a dining area and breakfast nook, creating a functional flow ideal for everyday living. Situated on a quiet street with a nicely sized yard, paved

  

  Brian Gearhart

  Benson & Mangold, LLC

  (410) 261-4318

  106 Sycamore Ave, Easton, MD 21601
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  /72

  $765,000

  • 3 Beds
  • 2.5 Baths
  • 2,240 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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  /31

  $675,000

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

  101 Sinclair St, Oxford, MD 21654

  Discover the perfect blend of comfort and coastal charm in this captivating 3-bedroom, 2.5-bath Colonial nestled on a fenced corner lot in the heart of Oxford. From its classic architecture to the inviting indoor and outdoor living spaces, this home is an ideal retreat for year-round living or a weekend escape.Step into the welcoming foyer, where you'll be greeted by spacious living and

  

  John McGlannan

  Meredith Fine Properties

  (410) 324-6472

  101 Sinclair St, Oxford, MD 21654
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  /50

  $810,000

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

  28309 Village Lake Way, Easton, MD 21601

  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 spaces for

  

  Lori Woods-Fortney

  Berkshire Hathaway HomeServices Homesale Realty

  (410) 517-7606

  28309 Village Lake Way, Easton, MD 21601
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  /39

  $575,000

  • 3 Beds
  • 3 Baths
  • 2,548 Sq Ft

  28642 Clubhouse Dr, Easton, MD 21601

  Come see this fantastic home at The Easton Club off the Oxford Corridor. House goes ACTIVE this Saturday and there is an Open House this Saturday from 12pm to 2pm. Photos will be up soon. Welcome to this beautifully designed two-level home in the sought-after Eastern Club community along Easton’s desirable Oxford corridor. Built in 1995 with timeless appeal, this residence combines modern comfort

  

  Martha Suss

  Coldwell Banker Realty

  (410) 593-1549

  28642 Clubhouse Dr, Easton, MD 21601
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  /32

  $350,000

  • 3 Beds
  • 1.5 Baths
  • 1,363 Sq Ft

  6827 Bellevue Rd, Royal Oak, MD 21662

  Charming One-Story Royal Oak Retreat – Minutes from St. Michaels Welcome to this impeccably maintained 3-bedroom, 1.5-bath home in the heart of Royal Oak, just minutes from the shops, restaurants, and waterfront of historic St. Michaels. This charming one-story residence offers beautiful hardwood floors, an updated full bath, and a warm, inviting layout perfect for everyday living or weekend

  

  Angela Simonelli

  Compass

  (410) 200-0414

  6827 Bellevue Rd, Royal Oak, MD 21662
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  /31

  $365,000

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft

  6135 Summit St, Tilghman, MD 21671

  Welcome to your Eastern Shore getaway, located at 6135 Summit Street, Tilghman, Maryland. This charming property is just a short walk from Tilghman Island's best waterfront attractions, including two marinas and three excellent dining options. This two-bedroom, one-bath home reflects pride of ownership and has been well maintained, making it ready for you to enjoy a slower pace of life on

  

  John McGlannan

  Meredith Fine Properties

  (410) 593-3451

  6135 Summit St, Tilghman, MD 21671
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  /25

  $295,000

  • 3 Beds
  • 1 Bath
  • 1,224 Sq Ft

  21749 Camper Cir, Tilghman, MD 21671

  A fantastic opportunity awaits at 21749 Camper Circle in Tilghman, Maryland. This home is perfect for first-time buyers or investors looking for great value at an affordable price. It features central heating and air conditioning, three spacious bedrooms, and one full bathroom. Enjoy a large sunroom with tile flooring that is conveniently located next to the kitchen. The hardwood floors

  

  John McGlannan

  Meredith Fine Properties

  (410) 498-8659

  21749 Camper Cir, Tilghman, MD 21671
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  /53

  $850,000

  • 4 Beds
  • 3.5 Baths
  • 2,869 Sq Ft

  11 Brookletts Ave, Easton, MD 21601

  Fabulous Victorian in Historic Easton, Circa 1910 Step into timeless elegance just a block from the heart of Easton's vibrant downtown—home to the famous Plein Air Festival, Crackerjacks, The Avalon Theatre, Legal Assets, Doc’s Downtown Grille, Vintage Books, charming boutiques, and art galleries galore. This stunning 4–5 bedroom, 3,800+ sq ft Victorian beauty offers classic character with modern

  

  Martha Suss

  Coldwell Banker Realty

  (410) 892-1360

  11 Brookletts Ave, Easton, MD 21601
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  /78

  $495,000

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

  11778 Old Skipton Rd, Cordova, MD 21625

  *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. The renovated home is perfect for living and operating a small business, such as a real estate office, insurance agency, or other low profile retails

  

  Jane Gharfeh

  Ace Realty & Property Management, LLC.

  (410) 650-6320

  11778 Old Skipton Rd, Cordova, MD 21625
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  /24

  $174,900

  • Land
  • 2.49 Acres
  • $70,241 per Acre

  0 Holly Woods Rd, 5, Bay Hundred, MD 21665

  Deep Harbour Farm Sherwood 2.49. Acre Building Lot.This is one of the last remaining building lots available in this wonderful water privileged community.Located at the end of a cul-de-sac on Holly Woods Road just steps away from the community waterfront pier & boat dock. Great opportunity to build the home of your own design now or in the future.

  

  John McGlannan

  Meredith Fine Properties

  (667) 222-5571

  0 Holly Woods Rd, 5, Bay Hundred, MD 21665
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  /10

  $80,000

  • Land
  • 0.3 Acre
  • $266,667 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

  (667) 382-8747

  21472 Willey Rd, Tilghman, MD 21671
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  /13

  $899,000

  • Land
  • 2.09 Acres
  • $430,144 per Acre

  0000 Sailors Retreat Rd, Oxford, MD 21654

  Explore an exceptional investment opportunity with this 2.09+/- acre waterfront lot in Sailors Retreat. With approximately 189 feet of water frontage on Island Creek and a six-bedroom perc approval, this property is primed for development. Its high elevation and protected shoreline, complemented by mature oak trees, offer a serene environment just minutes away from local amenities in Oxford and

  

  Brian Gearhart

  Benson & Mangold, LLC

  (667) 303-2608

  0000 Sailors Retreat Rd, Oxford, MD 21654
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  /12

  $75,000

  • Land
  • 0.3 Acre
  • $250,000 per Acre

  0 Sinclair Rd, Tilghman Island, MD 21671

  Sinclair Ave. Tilghman Island. Clear level building lot with public sewer. This lot is ready for you to make your dream of island life come true.Enjoy the best sunsets at the end of the street at Sinclair Community Park .

  

  John McGlannan

  Meredith Fine Properties

  (667) 297-6839

  0 Sinclair Rd, Tilghman Island, MD 21671
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  /5

  $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

  (443) 205-7213

  0 Unionville Rd Unit MDTA2008824, Easton, MD 21601
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  /42

  $434,000

  • 3 Beds
  • 2.5 Baths
  • 2,066 Sq Ft

  29184 Corbin Pkwy, Easton, MD 21601

  NEW ROOF -- NEW CARPET-- ALL NEW INSULATION AND FLOOR VAPOR BARRIER IN CRAWL SPACE-- NEW PAINT IN UPSTAIRS HALL, STAIR WAY , FOYER, KITCHEN AND FAMILY ROOM !! Welcome to 29184 Corbin Parkway located in Easton Maryland. Colonial offering a lovely sunroom with tray ceiling and tile floors and door to the back patio. Family room with gas fireplace. Kitchen with sile stone counter tops. The master

  

  Joanne Brown

  Meredith Fine Properties

  (410) 469-8790

  29184 Corbin Pkwy, Easton, MD 21601
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  /9

  $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

  (410) 421-7750

  0 St Michaels Rd Unit MDTA2012442, Newcomb, MD 21653
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  /19

  $397,440 New Construction

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

  1213 Loch Ness Ln, Trappe, MD 21673

  New Luxury 3 Bedroom spacious 3 level Townhome with a 2 car garage. Designer counter tops. Move in ready for July 2025. Photos are for illustration purposes. Agents must accompany buyer during first visit to the community.

  

  Terri Hill

  Builder Solutions Realty

  (443) 806-8828

  1213 Loch Ness Ln, Trappe, MD 21673
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  /18

  $294,990 New Construction

  • 2 Beds
  • 2.5 Baths
  • 1,798 Sq Ft

  1431 Lake Geneva Dr, Trappe, MD 21673

  Devonshire Townhouse front load garage July delivery! Open plan kitchen with stainless steel appliances. Photos are for illustration purposes. Agents must accompany buyer during first visit to the community.

  

  Terri Hill

  Builder Solutions Realty

  (443) 347-5819

  1431 Lake Geneva Dr, Trappe, MD 21673
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  /19

  $340,940 New Construction

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

  1219 Loch Ness Ln, Trappe, MD 21673

  Brand New - July delivery 3 bedroom townhouse,2 car garage and all appliances included. Photos are for illustration purposes. Agents must accompany buyer during first visit to the community.

  

  Terri Hill

  Builder Solutions Realty

  (443) 244-6808

  1219 Loch Ness Ln, Trappe, MD 21673
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  /18

  $284,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,798 Sq Ft

  1435 Lake Geneva Dr, Trappe, MD 21673

  Move in ready for a July delivery! New Devonshire Townhouse, Open plan kitchen. Photos are for illustration purposes. Agents must accompany buyer during first visit to the community.

  

  Terri Hill

  Builder Solutions Realty

  (443) 241-2483

  1435 Lake Geneva Dr, Trappe, MD 21673
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  /19

  $334,290 New Construction

  • 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

  (443) 407-8476

  1217 Loch Ness Ln, Trappe, MD 21673
• 

  

  /19

  $319,840 New Construction

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

  1215 Loch Ness Ln, Trappe, MD 21673

  Brand New Luxury Townhome in Lakeside at Trappe - Move into this lovely Elmwood Model 2,254 Upgraded kitchen with stainless steel appliances. This is a great home for entertaining. Photos are for illustration purposes. Agents must accompany buyer during first visit to the community.

  

  Terri Hill

  Builder Solutions Realty

  (443) 332-7874

  1215 Loch Ness Ln, Trappe, MD 21673
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  /17

  $359,990 New Construction

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

  1666 Lake Placid Dr, Trappe, MD 21673

  Don't miss out on this lovely, 3-bedroom, one story home! You will also love the community of Lakeside at Trappe for its convenient amenities and picturesque wooded areas. Photos are for illustration purposes. Agents must accompany buyer during first visit to the community.

  

  Terri Hill

  Builder Solutions Realty

  (443) 332-9488

  1666 Lake Placid Dr, Trappe, MD 21673
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  /29

  $385,000

  • 3 Beds
  • 2 Baths
  • 1,408 Sq Ft

  7384 Brett Rd, Easton, MD 21601

  ***Mortgage savings may be available for buyers of this listing*** Built in 1984, this single-level home has been fully renovated with thoughtful updates throughout. Recent improvements include fresh interior paint and a brand-new patio, perfect for outdoor living. Inside, you’ll find wood flooring across the main spaces and a modern, neutral color palette. The open kitchen is equipped with

  Barbara McCaffrey Redfin Corp

  7384 Brett Rd, Easton, MD 21601
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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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  /80

  $1,250,000

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

  28028 Playtor Rd, Easton, MD 21601

  Welcome to this stunning William Poole-designed Tidewater Colonial, nestled on approximately 2.3 acres in the serene neighborhood of Waverly Island Estates, just three miles from the vibrant Town of Easton. This exceptional property blends classic architecture with modern amenities, offering a peaceful retreat on the Eastern Shore of Maryland. Step inside to discover a thoughtfully designed floor

  Coard Benson Benson & Mangold, LLC

  28028 Playtor Rd, Easton, MD 21601
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  /32

  $420,000

  • 4 Beds
  • 3.5 Baths
  • 2,036 Sq Ft

  202 Tubman Dr, Easton, MD 21601

  Beautifully maintained 4 bedroom, 3.5 bath home minutes to downtown Easton offering a rear two tiered deck, formal living and dining rooms, family room w/ wood floors, and open kitchen with island , newer built-in microwave, dishwasher, range, frig, and granite counters. Mostly finished basement has a full bath w/shower-tub. Laundry room (w/newer W/D) on 2nd floor where bedrooms and primary

  Craig Linthicum Benson & Mangold, LLC

  202 Tubman Dr, Easton, MD 21601
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  /51

  $422,000

  • 3 Beds
  • 2 Baths
  • 1,540 Sq Ft

  29345 Greenfield Ave, Trappe, MD 21673

  OPEN HOUSE, Saturday, October 25, 11am - 1pm...Motivated Seller...Huge Price Improvement!...Welcome to your new home with no HOA in the charming town of Trappe, where serenity meets modern comfort! Nestled on a nearly half-acre corner lot, this beautiful ranch home is the perfect blend of spaciousness and light. The open floor plan and vaulted ceilings immediately captivate, creating an inviting

  Darlene Winegardner RE/MAX Executive

  29345 Greenfield Ave, Trappe, MD 21673
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  /91

  $8,750,000

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

  27295 Southside Island Creek Rd, Trappe, MD 21673

  Wilderness Estate- REVISED OFFERING INCLUDES 5 PARCELS 6.27.25- This quintessential Eastern Shore farm is located along the Choptank River in Trappe, Maryland. Comprised of 234 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

  Coard Benson Benson & Mangold, LLC

  27295 Southside Island Creek Rd, Trappe, MD 21673
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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
• 

  

  /23

  $419,990 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
• 

  

  /27

  $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
• 

  

  /21

  $449,990 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
• 

  

  /25

  $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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