Eastern Shore of Maryland Luxury Listings

Curated by Shane Hall. Last updated February 28
See what's out there in our most sought after neighborhoods throughout the areas of the Eastern Shore of Maryland that we service. Those areas include popular towns like Easton, Saint Michaels, Oxford, Stevensville, Queenstown, Chestertown and many more throughout Queen Annes, Talbot and Kent Counties. Each property in this collection is over $!M, not discerning of price or condition. This is one of the most popular searches for our clients and we review each property to make sure we have the most accurate information for it, up to the minute. Please reach out if anything catches your attention. We can put together a personalized list for you upon request, at no charge. Let's see if we can get you in to take a look at what your next chapter could be!
1/16
Active Under ContractVirtual Tour

$2,350,000

3
Bedrooms
3,280
Square Feet
0.1
Acres

Sunset Wharf, Stevensville, MD 21666

1/16
PendingVirtual Tour

$2,375,000

3
Bedrooms
3,280
Square Feet
0.1
Acres

Sunset Wharf, Stevensville, MD 21666

1/41
Open: 6/8 01:00PM - 03:00PM

$1,995,000

3
Bedrooms
3,562
Square Feet
4.82
Acres

7369 Drum Point Road, St. Michaels, MD 21663

$950,000 | 5092 Edwards Lane, Rock Hall, MD 21661
1/50
Closed 5/30/25

$950,000

1
Bedrooms
838
Square Feet
5.04
Acres

5092 Edwards Lane, Rock Hall, MD 21661

$1,294,000 | 214 South Washington Street, Easton, MD 21601
1/47
Closed 3/28/25

$1,294,000

4
Bedrooms
3,560
Square Feet
0.63
Acres

214 South Washington Street, Easton, MD 21601

an aerial view of a golf course with chairs
1/43
Virtual Tour

$1,450,000

3
Bedrooms
4,446
Square Feet

23393 Cacaway Farm Lane, Chestertown, MD 21620

$1,190,000 | 4938 Huntingfield Road, Rock Hall, MD 21661
1/36
Open: 6/7 10:00AM - 12:00PM

$1,190,000

5
Bedrooms
2,174
Square Feet
0.83
Acres

4938 Huntingfield Road, Rock Hall, MD 21661

$2,375,000 | Sunset Wharf, Stevensville, MD 21666
1/16
Coming SoonVirtual Tour

$2,375,000

3
Bedrooms
3,280
Square Feet
0.1
Acres

Sunset Wharf, Stevensville, MD 21666

$1,260,000 | 30154 Cods Point Road, Trappe, MD 21673
1/48
Closed 5/15/25

$1,260,000

3
Bedrooms
2,848
Square Feet
5.96
Acres

30154 Cods Point Road, Trappe, MD 21673

$1,399,000 | 450 Narrows Pointe Drive, Grasonville, MD 21638
1/81
Closed 6/6/25

$1,399,000

3
Bedrooms
3,000
Square Feet
Unavailable
Acres

450 Narrows Pointe Drive, Grasonville, MD 21638

$1,100,000 | 405 Cove Road, Queenstown, MD 21658
1/71
Closed 5/16/25Virtual Tour

$1,100,000

4
Bedrooms
4,750
Square Feet
1.43
Acres

405 Cove Road, Queenstown, MD 21658

$2,450,000 | 27303 Baileys Neck Road, Easton, MD 21601
1/84
Closed 3/14/25

$2,450,000

4
Bedrooms
3,544
Square Feet
4.3
Acres

27303 Baileys Neck Road, Easton, MD 21601

$2,350,000 | Sunset Wharf, Stevensville, MD 21666
1/16
Coming SoonVirtual Tour

$2,350,000

2
Bedrooms
3,280
Square Feet
0.1
Acres

Sunset Wharf, Stevensville, MD 21666

$795,000 | 4912 Bar Neck Road, Tilghman, MD 21671
1/78
Virtual Tour

$795,000

3
Bedrooms
1,550
Square Feet
3.13
Acres

4912 Bar Neck Road, Tilghman, MD 21671

a view of a house with a yard
1/85

$1,500,000

4
Bedrooms
4,600
Square Feet
20.97
Acres

105 Port Court, Grasonville, MD 21638

$2,995,000 | 9191 Deepwater Point Road, St. Michaels, MD 21663
1/103
Virtual Tour

$2,995,000

5
Bedrooms
5,088
Square Feet
12.55
Acres

9191 Deepwater Point Road, St. Michaels, MD 21663

$1,010,000 | 908 Monroe Manor Road, Stevensville, MD 21666
1/43
Closed 3/27/25

$1,010,000

4
Bedrooms
2,372
Square Feet
0.71
Acres

908 Monroe Manor Road, Stevensville, MD 21666

$1,445,000 | 8246 Ingleton Circle, Easton, MD 21601
1/41
Closed 3/7/25

$1,445,000

3
Bedrooms
3,186
Square Feet
2.13
Acres

8246 Ingleton Circle, Easton, MD 21601

$2,090,000 | 7701 Bloomfield Road, Easton, MD 21601
1/43
Closed 3/6/25

$2,090,000

6
Bedrooms
6,185
Square Feet
1.43
Acres

7701 Bloomfield Road, Easton, MD 21601

a front view of residential houses with yard and green space
1/50
Closed 4/3/25

$4,275,000

4
Bedrooms
4,458
Square Feet
4.22
Acres

7891 Fort Stokes Lane, Easton, MD 21601

$2,375,000 | Sunset Wharf, Stevensville, MD 21666
1/16
Coming SoonVirtual Tour

$2,375,000

4
Bedrooms
3,280
Square Feet
0.1
Acres

Sunset Wharf, Stevensville, MD 21666

$1,695,000 | 10425 Aberdeen Lane, Easton, MD 21601
1/81

$1,695,000

3
Bedrooms
2,951
Square Feet
9.85
Acres

10425 Aberdeen Lane, Easton, MD 21601

$1,899,000 | 216 East Chew Avenue, St. Michaels, MD 21663
1/56

$1,899,000

4
Bedrooms
3,575
Square Feet
0.34
Acres

216 East Chew Avenue, St. Michaels, MD 21663

a front view of house with yard and green space
1/76
Closed 4/22/25

$1,200,000

3
Bedrooms
2,708
Square Feet
21.76
Acres

4500 Grove Road, Trappe, MD 21673

$2,950,000 | 25320 White Hall Road, Royal Oak, MD 21662
1/30
Virtual Tour

$2,950,000

4
Bedrooms
2,784
Square Feet
99
Acres

25320 White Hall Road, Royal Oak, MD 21662

$1,700,000 | 5993 Hopkins Neck Road, Easton, MD 21601
Closed 5/30/25Virtual Tour

$1,700,000

4
Bedrooms
4,254
Square Feet
3.99
Acres

5993 Hopkins Neck Road, Easton, MD 21601

a front view of a house with a yard
1/25
New Construction

$999,900

3
Bedrooms
2,464
Square Feet
0.36
Acres

118 North Lake Drive, Stevensville, MD 21666

a view of an outdoor space with trees
1/63
Closed 3/14/25

$4,200,000

5
Bedrooms
8,453
Square Feet
5.32
Acres

6398 Hopkins Neck Road, Easton, MD 21601

an aerial view of a house with a yard and lake
1/65

$1,400,000

4
Bedrooms
2,986
Square Feet
55.94
Acres

1704 Busic Church Road, Marydel, MD 21649

a lake view with large trees
1/24
New Construction

$1,275,000

3
Bedrooms
Unavailable
Square Feet
4.14
Acres

715 Winchester Creek Road, Grasonville, MD 21638

front view of a house with a swimming pool
1/101
PendingVirtual Tour

$2,250,000

3
Bedrooms
4,114
Square Feet
2.05
Acres

365 Hemsley Drive, Queenstown, MD 21658

a view of a garden with plants and a bench
1/35

$1,950,000

6
Bedrooms
5,174
Square Feet
1.1
Acres

2817 Cox Neck Road, Chester, MD 21619

$19,995,000 | 5369 Morgans Point Drive, Oxford, MD 21654
1/50

$19,995,000

6
Bedrooms
24,767
Square Feet
6.86
Acres

5369 Morgans Point Drive, Oxford, MD 21654

$9,950,000 | 24629 Beverly Road, St. Michaels, MD 21663
1/92

$9,950,000

5
Bedrooms
10,309
Square Feet
9.72
Acres

24629 Beverly Road, St. Michaels, MD 21663

$2,400,000 | 6591 Cedar Cove Road, Royal Oak, MD 21662
1/105
Closed 4/3/25

$2,400,000

6
Bedrooms
5,018
Square Feet
8.78
Acres

6591 Cedar Cove Road, Royal Oak, MD 21662

$3,000,000 | 27919 Jarboe Drive, Easton, MD 21601
1/60
Closed 5/23/25

$3,000,000

4
Bedrooms
2,923
Square Feet
2.91
Acres

27919 Jarboe Drive, Easton, MD 21601

$8,800,000 | 27295 Southside Island Creek Road, Trappe, MD 21673
1/91
Virtual Tour

$8,800,000

6
Bedrooms
9,566
Square Feet
47.99
Acres

27295 Southside Island Creek Road, Trappe, MD 21673

a view of a green field
1/64
PendingVirtual Tour

$2,995,000

8
Bedrooms
8,107
Square Feet
12.71
Acres

8831 Quailsar Road, Easton, MD 21601

a front view of a house with a yard and garage
1/37
Virtual TourNew Construction

$1,499,900

5
Bedrooms
4,529
Square Feet
1.25
Acres

208 Tower Drive, Stevensville, MD 21666

$2,350,000 | 25839 Turner Avenue, Royal Oak, MD 21662
1/39
PendingNew Construction

$2,350,000

4
Bedrooms
3,085
Square Feet
1.51
Acres

25839 Turner Avenue, Royal Oak, MD 21662

a view of a lake with a mountain
1/62
Virtual Tour

$4,499,000

6
Bedrooms
3,700
Square Feet
4.48
Acres

27473 Westpoint Road, Easton, MD 21601

$9,900,000 | 6010 Shipyard Lane, Easton, MD 21601
1/71
Virtual TourNew Construction

$9,900,000

5
Bedrooms
14,935
Square Feet
13.02
Acres

6010 Shipyard Lane, Easton, MD 21601

Shane Hall

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