Luxury homes for sale & real estate in Dorchester County, MD

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ABOUT THIS HOME
Luxury Home for sale in Dorchester County, MD:
Rare opportunity in Dorchester County to purchase 108 +/- acres on Pig Neck Road just outside of Cambridge. Estimated 93 +/- acres tillable with 11.9 acres +/- acres woodland. Gorgeous old home in need or major repair or tear down. Value is in the land only. Numerous outbuildings, 20 x20 garage is newer and in good shape. Please enter home at your own risk and call local health department and planning and zoning for potential uses of property.

$1,495,000

3 beds2 baths3,344 sq ft

2238 Pig Neck Rd, Cambridge, MD 21613

93 acres tillable • 11.9 acres woodland • 20 x20 garage

(410) 643-4663

ABOUT THIS HOME
Luxury Home for sale in Dorchester County, MD:
Prepare to fall in love! More than just a house- this is a home, lovingly cared for and thoughtfully designed. It offers the perfect blend of comfort, character and privacy. Experience the peace, and tranquility of this secluded, move-in-ready waterfront retreat. Ideally located, just a short distance from historic Cambridge, the Hyatt Regency Chesapeake Bay Golf Resort and within an easy reach of Easton, Oxford, and St. Michaels. Only minutes from Blackwater Wildlife Refuge, where you can explore the outdoors, spot eagles’ nests, or enjoy canoeing, biking, and hiking trails. Beautifully updated and meticulously maintained, this 3-bedroom, 2-bath home offers over 2,300 square feet of

$875,000

3 beds2 baths2,120 sq ft

1318 Bell Ln, Woolford, MD 21677

0.89 acre lot • 2 garage spots • Built 1950

(410) 673-3344

ABOUT THIS HOME
Luxury Home for sale in Dorchester County, MD:
Set on 10 private acres in Dorchester County’s Neck District, this 6BR/4.5BA custom-built home offers 4,500 sq. ft. of living space, a rip-rapped shoreline, and sweeping views of the Middle Chesapeake Bay. Here, every detail has been designed for comfort, entertaining, and connection with the natural beauty of Maryland’s Eastern Shore. Step inside to hardwood floors and an open, traditional floor plan. The foyer leads to a waterfront family room featuring a stone fireplace with wood-burning insert and French doors opening to both a screened porch and a covered deck. The center island kitchen with breakfast bar offers abundant cabinetry, pantry space, stainless steel appliances,

$1,500,000

6 beds4.5 baths4,488 sq ft

5332 Ragged Point Rd, Cambridge, MD 21613

Private acres • French doors • Screened porch

(410) 228-2525

ABOUT THIS HOME
Luxury Home for sale in Dorchester County, MD:
This is 1301 Broadview Drive — a rare waterfront sanctuary where timeless design and the beauty of Maryland’s Eastern Shore come together in perfect harmony. Set on its own private peninsula with over 1,100 feet of shoreline, this custom New England–inspired residence offers sweeping views of the Chesapeake Bay, Little Choptank River, and Fishing Creek. From sunrise over the water to golden-hour gatherings by the pool, every moment here feels like a retreat. Thoughtfully designed and masterfully crafted, the home embodies quiet sophistication. Classic white cedar shake siding, Boston blend stonework, and bluestone terraces set a tone of understated elegance. Inside, spacio

$2,500,000

4 beds3.5 baths4,736 sq ft

1301 Broadview Dr, Cambridge, MD 21613

Gas fireplace • Gourmet kitchen • Light filled rooms

(410) 228-2525

ABOUT THIS HOME
Luxury Home for sale in Dorchester County, MD:
WATERFRONT! WATERFRONT! Direct access to the Chesapeake Bay via Hudson Creek! This sprawling rancher offers 7, yes SEVEN, bedrooms, 3 full baths and 1 half bath. You will marvel at the expansive living and dining areas that flow seamlessly and offer expansive water views. All of this on a 1.84 +/-acre parcel with an in-ground pool, a boat dock and approximately 222' of waterfrontage. This unique property will not last long! Schedule a showing today! Equally impressive views are present from the HUGE recreational room. Restricted to owner-occupants, non-profits and government agencies through 11/07/2025. HUD Case #244-000054. Equal Housing Opportunity.

$860,000

7 beds3.5 baths3,218 sq ft

5608 Riverton Rd, Cambridge, MD 21613

In-ground pool • Boat dock • 1.84 acre lot

(855) 687-2765

Property at 5304 Cassons Neck Rd, Cambridge, MD 21613, 7 beds, 4.5 baths

$1,350,000

7 beds4.5 baths3,584 sq ft

5304 Cassons Neck Rd, Cambridge, MD 21613

(410) 525-5435

Property at 1308 Town Point Rd, Cambridge, MD 21613, 4 beds, 4 baths

$899,000

4 beds4 baths2,900 sq ft

1308 Town Point Rd, Cambridge, MD 21613

(410) 228-0800

Property at 2202 Jenkins Creek Rd, Cambridge, MD 21613, 3 beds, 2.5 baths

$1,300,000

3 beds2.5 baths2,195 sq ft

2202 Jenkins Creek Rd, Cambridge, MD 21613

(443) 225-4100

Property at 1307 Broadview Dr, Cambridge, MD 21613, 5 beds, 4.5 baths

$1,099,000

5 beds4.5 baths2,740 sq ft

1307 Broadview Dr, Cambridge, MD 21613

(410) 822-6665

Property at 2208 Horns Point Rd, Cambridge, MD 21613, 5 beds, 4.5 baths

$1,300,000

5 beds4.5 baths4,272 sq ft

2208 Horns Point Rd, Cambridge, MD 21613

(410) 228-0800

Property at 1826 Hoopersville, Fishing Creek, MD 21634, 2 beds, 2 baths

$870,000

2 beds2 baths1,200 sq ft

1826 Hoopersville, Fishing Creek, MD 21634

(410) 304-2011

Property at 2613 Hoopers Island Rd, Fishing Creek, MD 21634, 4 beds, 3 baths

$899,900

4 beds3 baths4,752 sq ft

2613 Hoopers Island Rd, Fishing Creek, MD 21634

(410) 864-5750

Property at 6011 Sunnyside Ct, East New Market, MD 21631, 4 beds, 2.5 baths

$925,000

4 beds2.5 baths2,636 sq ft

6011 Sunnyside Ct, East New Market, MD 21631

(410) 429-7425

Property at 5405 Wesley Rd, Hurlock, MD 21643

$975,000

— beds— baths— sq ft

5405 Wesley Rd, Hurlock, MD 21643

(410) 543-4545

Property at 1508 Hambrooks Blvd, Cambridge, MD 21613

$1,000,000

— beds— baths— sq ft

1508 Hambrooks Blvd, Cambridge, MD 21613

(410) 429-7425

Property at Griffith Neck Rd, Cambridge, MD 21613

$910,000

— beds— baths— sq ft

Griffith Neck Rd, Cambridge, MD 21613

(410) 543-4545

Property at 2745 Gypsy Hill Farm Rd, Cambridge, MD 21613

$990,000

— beds— baths— sq ft

2745 Gypsy Hill Farm Rd, Cambridge, MD 21613

(410) 543-2440

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ABOUT THIS HOME
Luxury Home for sale in Dorchester County, MD:
Beautiful 108-acre farm on Carroll Pond with limited access to the Chesapeake Bay. The original 1900s home has seen updates over the years and currently operates as an Airbnb (Trinity Oaks Farm). A hunter’s dream, private getaway, or ideal full-time homestead. The property includes 42 acres of forest, 33 acres of fields with 3 paddocks (with water and electric), and 32 acres of marsh and pond. Enjoy two ponds, wooded trails, abundant wildlife, and fenced areas for animals. The land is enrolled in a Preservation & Forestry Stewardship Plan. Several outbuildings provide additional utility. Kayak from the pond out to the bay and take in the peaceful, secluded setting. Cable has rec

$1,050,000

4 beds2.5 baths2,214 sq ft

49465 Demko Rd, Lexington Park, MD 20653

108.84 acre lot • 10 parking spots • Built 1900

(301) 862-2169

ABOUT THIS HOME
Luxury Home for sale in Dorchester County, MD:
Located in the heart of St. Michaels' historic district, this adorable cottage has a rare zoning that allows for short term vacation rental, and it has been a very successful one. The current owner has great reviews and reports revenues of $65,000 in 2025. There is excellent bedroom separation, with one bedroom on the first floor in the back, the other on the second floor in the front. The kitchen was recently renovated and the heating/air conditioning was replaced in 2024. The yard is spacious, with a fenced oyster shell yard featuring a firepit and off street parking for two cars. This home is turnkey - all furnishings and short term rental supplies included. Don't miss this rare opportun

$1,099,000

2 beds2.5 baths1,445 sq ft

100 Grace St, St Michaels, MD 21663

7,725 sq ft lot • 2 parking spots • Built 1890

(410) 745-0415

NEW CONSTRUCTION

ABOUT THIS HOME
Luxury Home for sale in Dorchester County, DE:
Experience the craftsmanship and quality of a to-be-built custom home by award-winning Bay to Beach Builders, celebrated for their Amish craftsmanship and exceptional attention to detail. The Sunnyside- a 2108 square foot ranch home features an open lay-out with three bedrooms, two baths and a two-car garage. Its open-concept floor plan connects the kitchen, dining, and great room for easy flow, and a spacious primary suite, ample storage, and optional design upgrades offer comfort, functionality, and timeless appeal. Located in Seaford, Delaware, this rare opportunity offers over five acres of prime, buildable land with city water, sewer, and utilities already in place, making it ready fo

$882,000

3 beds2 baths2,108 sq ft

70 South St, Seaford, DE 19973

Open lay-out • Sewer • Custom home

(302) 703-1144

ABOUT THIS HOME
Luxury Home for sale in Dorchester County, MD:
PROFESSIONAL PHOTOS COMING SOON. CHECK WITH LISTING AGENT FOR MORE DETAILS. A True Eastern Shore Estate! Experience unparalleled living at this magnificent 58+ acre Preston estate, an extraordinary opportunity to own a property that perfectly blends luxury, comfort, and versatility. The stately main residence features 5 bedrooms, 6 full and 3 half baths, and an impressive foyer with a grand double staircase. Entertain with ease in the gourmet kitchen with butler’s pantry, formal dining and living rooms, two offices, family room, indoor grill room, and a second-floor family room. Additional highlights include four fireplaces, a gym, laundry room, and attached 3-car and 4-car garages. A

$2,999,000

8 beds12 baths9,364 sq ft

4218 Harmony Rd, Preston, MD 21655

58.48 acre lot • 55 garage spots • Pool

(410) 543-4545

COMING SOON

ABOUT THIS HOME
Luxury Home for sale in Dorchester County, MD:
Spacious 3,000 sqft two-story waterfront home on 3/4 acre parcel on Harris Creek where it joins the Choptank River for an 11-mile view to Cambridge. House is brick and block on the first level with redwood siding on the second level in board and batten style. 150ft heavily built and reinforced bulkhead waterfront with recently renovated 75ft long dock. Second floor includes four bedrooms with water views and a bunk room all with oak flooring recently refinished, built-in chest of drawers and closets, built in desks and bookcases. Second floor includes a great room with cathedral ceiling and outside deck facing Harris Creek, a full bath and powder room, all tiled. First floor has open area k

$850,000

4 beds2.5 baths2,286 sq ft

5489 Rude Ave, Tilghman, MD 21671

0.74 acre lot • 2 garage spots • Built 1970

(410) 822-6272

3D WALKTHROUGH

ABOUT THIS HOME
Luxury Home for sale in Dorchester County, MD:
Welcome to an extraordinary Chesapeake Bay estate where more than 5,000 square feet of refined coastal living meet private beach access and sweeping water views that shape every moment. This custom-built five-bedroom, five-bath home blends timeless craftsmanship with the serenity of the shoreline, offering a lifestyle that feels both luxurious and effortlessly relaxed. A grand two-story foyer welcomes you with sunlight and soaring ceilings. To the right, a flexible guest suite or office offers privacy and comfort. To the left, a full bath is thoughtfully placed to serve the main level with ease. Continue forward and the home opens into an impressive gourmet kitchen designed for gathering an

$1,339,900

5 beds5 baths5,088 sq ft

3095 Calvert Blvd, Lusby, MD 20657

0.31 acre lot • 6 parking spots • Built 1984

(443) 968-9595

Property at 509 Tony Tank Ln, Salisbury, MD 21801, 3 beds, 3.5 baths

$975,000

3 beds3.5 baths3,325 sq ft

509 Tony Tank Ln, Salisbury, MD 21801

(410) 543-4545

Property at 25835 Turner Ave, Royal Oak, MD 21662, 3 beds, 2.5 baths

$942,900

3 beds2.5 baths2,200 sq ft

25835 Turner Ave, Royal Oak, MD 21662

(410) 822-6665

Property at 23961 Lynnewood Dr, Saint Michaels, MD 21663, 4 beds, 3.5 baths

$3,100,000

4 beds3.5 baths4,035 sq ft

23961 Lynnewood Dr, Saint Michaels, MD 21663

(410) 822-1415

Property at 24390 Oakwood Park Rd, Saint Michaels, MD 21663, 4 beds, 3.5 baths

$1,900,000

4 beds3.5 baths2,839 sq ft

24390 Oakwood Park Rd, Saint Michaels, MD 21663

(410) 745-0415

Property at 28701 Edgemere Rd, Easton, MD 21601, 3 beds, 2 baths

$1,390,000

3 beds2 baths4,008 sq ft

28701 Edgemere Rd, Easton, MD 21601

(410) 770-9255

Property at 28711 Hope Cir, Easton, MD 21601, 4 beds, 3.5 baths

$1,235,000

4 beds3.5 baths4,500 sq ft

28711 Hope Cir, Easton, MD 21601

(410) 822-6665

Property at 3547 Prchal Rd, Preston, MD 21655, 4 beds, 3 baths

$875,000

4 beds3 baths3,149 sq ft

3547 Prchal Rd, Preston, MD 21655

(410) 972-4000

Property at 5084 Ferry Neck Rd, Royal Oak, MD 21662, 4 beds, 3 baths

$4,395,000

4 beds3 baths7,903 sq ft

5084 Ferry Neck Rd, Royal Oak, MD 21662

(703) 319-3344

Property at 206 Harbor Dr, Lusby, MD 20657, 4 beds, 5.5 baths

$1,299,000

4 beds5.5 baths4,406 sq ft

206 Harbor Dr, Lusby, MD 20657

(301) 609-9000

Property at 21485 Island Club Rd, Tilghman, MD 21671, 5 beds, 4.5 baths

$2,499,000

5 beds4.5 baths4,303 sq ft

21485 Island Club Rd, Tilghman, MD 21671

(410) 822-6665

Property at 27473 Westpoint Rd, Easton, MD 21601, 4 beds, 5.5 baths

$4,250,000

4 beds5.5 baths3,700 sq ft

27473 Westpoint Rd, Easton, MD 21601

(410) 822-6272

Property at 28613 Lois Ln, Easton, MD 21601, 5 beds, 4.5 baths

$2,595,000

5 beds4.5 baths6,211 sq ft

28613 Lois Ln, Easton, MD 21601

(410) 822-6665

$2,500,000

— beds— baths— sq ft

Dover Rd, Easton, MD 21601

(410) 822-1980

Property at 0 N Market St, Seaford, DE 19973

$899,000

— beds— baths— sq ft

0 N Market St, Seaford, DE 19973

(302) 674-3400

Luxury Homes for Sale in Dorchester County

There are currently 17 luxury homes for sale in Dorchester County at a median listing price of $325K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Dorchester County stay on the market for 85 days and receive 1 offers. This map is refreshed with the newest listings in Dorchester County every 15 minutes.

In the past month, 40 homes have been sold in Dorchester County. In addition to houses in Dorchester County, there were also 13 condos, 35 townhouses, and 3 multi-family units for sale in Dorchester County last month. Find your dream home in Dorchester County using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Dorchester County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Dorchester County. If you're looking to sell your home in the Dorchester County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Dorchester County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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Luxury homes for sale & real estate in Dorchester County, MD

Luxury Homes for Sale in Dorchester County

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