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Eastern Shore Waterfront Properties

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18 Owens Landing Ct, Perryville image
18 Owens Landing Ct, Perryville $420,000

Coming Soon- thank you for your patience as we prepare this home for listing. Professional photos, professional write up and update to the listing information all Coming ...

  • 2 Beds
  • 2 Baths
  • MDCC2023466 MLS
215 Alynn Way, Queenstown image
215 Alynn Way, Queenstown $2,795,000

Experience exceptional waterfront living on the Wye River in the prestigious Belle Point Farm community. Situated on 2.44 beautifully landscaped acres with approximately ...

  • 4 Beds
  • 6 Baths
  • MDQA2019002 MLS
25705 Edgeview Rd, Royal Oak image
25705 Edgeview Rd, Royal Oak $2,375,000

Solitude on Edge Creek with over 300+/- feet of tranquil waterfrontage and protected shoreline. Five-foot-wide pier with ample room for boats, substantial boat lift and 2...

  • 5 Beds
  • 5 Baths
  • MDTA2015336 MLS
28041 Old Country Club Rd, Easton image
28041 Old Country Club Rd, Easton $3,150,000

THE HELM – Spectacularly positioned on an elevated private point overlooking Peachblossom Creek, The Helm is an exceptional 5BR/4FB/2HB waterfront residence offering extr...

  • 5 Beds
  • 6 Baths
  • MDTA2015318 MLS
8242 Ingleton Cir, Easton image
8242 Ingleton Cir, Easton $2,750,000

Beautifully positioned on 2.41 acres overlooking the coveted Miles River, this exceptional 4BR/4.5BA coastal residence offers sweeping water views, light-filled interiors...

  • 4 Beds
  • 5 Baths
  • MDTA2015306 MLS
2703 Sherman Dr, Chester image
2703 Sherman Dr, Chester $699,000

Nestled in the serene Harbor View subdivision, this Colonial-style home offers a perfect blend of luxury and comfort. The interior features elegant bamboo and ceramic til...

  • 3 Beds
  • 3 Baths
  • MDQA2018980 MLS
1400 Town Point Rd, Chesapeake City image
1400 Town Point Rd, Chesapeake City $2,300,000

Some homes offer a place to live. This one offers a place to make memories. Set on approximately 11 acres in Chesapeake City, Maryland, this distinctive retreat combines...

  • 4 Beds
  • 5 Baths
  • MDCC2023346 MLS
269 E Main St, Elkton image
269 E Main St, Elkton $250,000

Nestled on a generous 1.03-acre Creek Front Double Lot, this exquisite Colonial residence exudes timeless charm and sophistication, offering a unique opportunity to embra...

  • 3 Beds
  • 3 Baths
  • MDCC2023348 MLS
22703 Emilys Ln, Wittman image
22703 Emilys Ln, Wittman $2,495,000

"Creekside" is a classic Eastern Shore Waterfront Retreat. Sited on 5 private, partially-wooded acres with extensive shoreline, the 3,800 sq ft main house provides panora...

  • 5 Beds
  • 5 Baths
  • MDTA2015284 MLS
104 Mariners Cir, Stevensville image
104 Mariners Cir, Stevensville $1,825,000

Set on more than three acres, this distinctive waterfront residence offers over 3,400 square feet of living space, sweeping water views and beautiful sunrises. From the m...

  • 4 Beds
  • 4 Baths
  • MDQA2018960 MLS
117 River Run, Queenstown image
117 River Run, Queenstown $1,300,000

Wye River Waterfront Living at Its Best! If you love boating, fishing, crabbing, and being on the water, this Cape Cod-style home on the Wye River may be just what you h...

  • 4 Beds
  • 3 Baths
  • MDQA2018938 MLS
210 Rowland Dr, Port Deposit image
210 Rowland Dr, Port Deposit $315,000

Nestled in the serene Tomes Landing community, this charming 3-bedroom, 2.5-bath condominium offers a perfect blend of comfort and convenience. Enjoy the modern kitchen e...

  • 3 Beds
  • 3 Baths
  • MDCC2023338 MLS
208 Widgeon Way, Chester image
208 Widgeon Way, Chester $599,900

New Listing! Bayside Condos * End Unit with Garage * Direct Water Views * Direct View of Castle Harbor Marina * Best Location in the Community* Potential to See Your Boat...

  • 3 Beds
  • 4 Baths
  • MDQA2018920 MLS
419 Craney Creek Rd, Stevensville image
419 Craney Creek Rd, Stevensville $3,495,000

Set on nearly **3 private acres with more than 300 feet of Chesapeake Bay waterfront**, 419 Craney Creek is a custom-built home designed to embrace its remarkable setting...

  • 4 Beds
  • 6 Baths
  • MDQA2018910 MLS
9338 Bantry Rd, Easton image
9338 Bantry Rd, Easton $2,999,999

Current owner/architect was in process of large upscale renovation when planes changed. The property has received Talbot County approval for a new 5-6 bedroom septic sy...

  • MDTA2015132 MLS
Little Harbor Way Unit 1, Chestertown image
Little Harbor Way Unit 1, Chestertown $1,800,000

**Price increase due to the home’s expanded footprint—over 1,200 additional square feet!** **To be built! Welcome to this beautifully designed 3,540 sq. ft. home in Ches...

  • 4 Beds
  • 4 Baths
  • MDKE2007154 MLS
1509 Calvert Rd, Chester image
1509 Calvert Rd, Chester $1,350,000

Coastal elegance meets effortless waterfront living on the sunrise side of Prospect Bay. From the moment you arrive, this exceptional home feels special. Ideally positio...

  • 4 Beds
  • 3 Baths
  • MDQA2018902 MLS
1007 Oyster Cove Dr, Grasonville image
1007 Oyster Cove Dr, Grasonville $1,199,000

SPECTACULAR WATERFRONT VIEWS OF A LIFETIME! Luxury and the Coveted "BIG SIX" Rare to Come on the Market * Full Water Access * Deeded 40' Deep Water Boat Slip * Attache...

  • 3 Beds
  • 4 Baths
  • MDQA2018818 MLS
9338 Bantry Rd, Easton image
9338 Bantry Rd, Easton $2,695,000

Significant price reduction! Holly House | Miles River Waterfront Holly House is a distinctive waterfront property on the Upper Miles River, set on five beautifully lan...

  • 4 Beds
  • 5 Baths
  • MDTA2015270 MLS
6136 Tilghman Island Rd, Tilghman image
6136 Tilghman Island Rd, Tilghman $300,000

REAL ESTATE AUCTION featuring ON SITE and SIMULCAST BIDDING!! Online Bidding Opens - Thursday, October 29, 2026. Live On Site Auction - Friday, October 30, 2026 at 12:00...

  • MDTA2015268 MLS
6016 Blue Heron Dr, East New Market image
6016 Blue Heron Dr, East New Market $1,495,000

Custom-built new construction on 3.73 acres along the Choptank River, offering a truly unique waterfront setting with views of the river, a peaceful backwater slough and ...

  • 3 Beds
  • 4 Baths
  • MDDO2013248 MLS
34 Queen Anne Way Unit A, Chester image
34 Queen Anne Way Unit A, Chester $570,000

The view is the main event. Homes throughout Queens Landing sit at varying distances from the waterfront, and it is hard to get closer than this. Positioned directly alon...

  • 2 Beds
  • 2 Baths
  • MDQA2018790 MLS
225 Hickory Ridge Dr, Queenstown image
225 Hickory Ridge Dr, Queenstown $1,195,000

A Private Wye River Sanctuary! Some properties offer a home. Others offer a lifestyle. This exceptional Wye River retreat offers both.Set along one of the Eastern Shore’...

  • 4 Beds
  • 3 Baths
  • MDQA2018866 MLS
251 Prospect Bay Dr W, Grasonville image
251 Prospect Bay Dr W, Grasonville $1,650,000

Enjoy broad water views and spectacular sunsets from this beautifully situated 1.02-acre waterfront property, with water views enjoyed throughout much of the home. Design...

  • 4 Beds
  • 4 Baths
  • MDQA2018878 MLS
162 Kirwans Landing Ln, Chester image
162 Kirwans Landing Ln, Chester $1,199,900

It's rare to find a designer home on a 1.4 acre lot with an in-ground saltwater pool and direct waterfront access on Kent Island at this price tag. From the moment you ar...

  • 5 Beds
  • 3 Baths
  • MDQA2018812 MLS
3118 Bay View Dr, Church Creek image
3118 Bay View Dr, Church Creek $724,950

Grand views come with this breathtaking waterfront home! Step inside to an inviting open floor plan featuring soaring cathedral ceilings, skylights, and floor-to-wall ...

  • 3 Beds
  • 2 Baths
  • MDDO2013174 MLS
12 Greenwood Shls, Grasonville image
12 Greenwood Shls, Grasonville $549,000

Enjoy easy one-level living in the highly desirable Prospect Bay community at 12 Greenwood Shoals. Set on just over an acre, this inviting three-bedroom, two-bath home of...

  • 3 Beds
  • 2 Baths
  • MDQA2018822 MLS
11 Ne 11 Ne Isle Drive Drive, North East image
11 Ne 11 Ne Isle Drive Drive, North East $597,000

Come enjoy this stunning waterfront 3 bedroom, 2 bath Twin/ townhome, minutes from quaint town of North East, now available in the community of North East Isle. This Twi...

  • 3 Beds
  • 2 Baths
  • MDCC2023064 MLS
property image
129 Wheelhouse Way Unit 21, Chester $1,439,999

Experience exceptional waterfront living in this stunning 3-bedroom, 2.5-bath condominium offering what are arguably the best views in the community. Positioned to captur...

  • 3 Beds
  • 3 Baths
  • MDQA2018858 MLS
129 Wheelhouse Way Unit 11, Chester image
129 Wheelhouse Way Unit 11, Chester $585,000

Priced well below market value! The builder can not compete with this price. Welcome to one of the most desirable locations in Four Seasons at Kent Island, where luxury,...

  • 2 Beds
  • 3 Baths
  • MDQA2018848 MLS
7 Queen Victoria Way Unit B, Chester image
7 Queen Victoria Way Unit B, Chester — Queens Landing $499,000

Welcome to 7B Queen Victoria Way at Queen’s Landing, a beautifully renovated waterfront residence w/ spectacular views of the marina basin, marina fairway, and Chester Ri...

  • 2 Beds
  • 3 Baths
  • MDQA2018794 MLS
  • Queens Landing Bldg.
Main Street, Neavitt image
Main Street, Neavitt $350,000

Residential lot available minutes from St Michaels. .56 of an acre with 200 feet water frontage. Public water and sewer hookup is available. Build your waterfront dream h...

  • MDTA2015212 MLS
2344 Hoopers Island Rd, Fishing Creek image
2344 Hoopers Island Rd, Fishing Creek $1,075,000

Welcome to the most private wooded parcel of land on Upper Hooper's island , accessed by a private road and bridge from Hooper's Island Road , to the exclusive 8 acres of...

  • 3 Beds
  • 3 Baths
  • MDDO2013210 MLS
6324 Quaker Neck Rd, Chestertown image
6324 Quaker Neck Rd, Chestertown $2,895,000

Discover 6324 Quaker Neck Road, an exceptional waterfront estate spanning over 5 acres along the East Fork of Langford Creek offering over 5 feet of water at low tide. Ov...

  • 5 Beds
  • 4 Baths
  • MDKE2007098 MLS
3313 Belfiore Rd, Church Creek image
3313 Belfiore Rd, Church Creek $575,000 ▼

Welcome to your own waterfront retreat in beautiful Church Creek! This unique property offers two lots and approximately 200 feet of Chesapeake Bay waterfront, giving you...

  • 3 Beds
  • 3 Baths
  • MDDO2013202 MLS
101 Main St, Secretary image
101 Main St, Secretary $355,000

Waterfront Living at Its Best! Enjoy low-maintenance living with beautiful water views and your own deeded boat slip with 45' shared pier, complete with a 3-year-old, 10,...

  • 3 Beds
  • 3 Baths
  • MDDO2013182 MLS
105 N Water St Unit 3, Chestertown image
105 N Water St Unit 3, Chestertown $489,000

Second story, waterfront condo in historic Chestertown. Comes with a private boat slip at the end of the dock. 2 bedrooms and 2 full baths. Spacious patio with a stunnin...

  • 2 Beds
  • 2 Baths
  • MDKE2007112 MLS
437 W Lewis Shore Rd, Elkton image
437 W Lewis Shore Rd, Elkton — None Available $340,000 ▼

Rarely available waterfront cottage in Lewis Shore! Tucked away beyond the woods and farmland on the outskirts of Elkton, this charming retreat offers the opportunity t...

  • 3 Beds
  • 2 Baths
  • MDCC2023160 MLS
  • None Available Bldg.
15 Qun Ann Way Unit E, Chester image
15 Qun Ann Way Unit E, Chester $539,000 ▼

Located in the beautiful Queens Landing community, this Spanish-style waterfront townhouse offers a luxurious lifestyle with stunning river views. The interior boasts an ...

  • 2 Beds
  • 3 Baths
  • MDQA2018746 MLS
5 Oakley St Unit 304/302, Cambridge image
5 Oakley St Unit 304/302, Cambridge — Oakley Beach Condominium $424,500

Nestled in the charming and historic West End of Cambridge, this delightful top floor 2-bedroom, 2-bathroom condominium at Oakley Beach offers a perfect blend of comfort ...

  • 2 Beds
  • 2 Baths
  • MDDO2013150 MLS
  • Oakley Beach Condominium Bldg.

Eastern Shore Waterfront Homes

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Taylor Properties
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