St. Michaels, MD homes for sale & real estate

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NEW 18 HRS AGO

ABOUT THIS HOME
St. Michaels, MD Homes for Sale
Located in Bentley Hay and within walking distance of Historic St. Michaels, this charming cottage would make an exceptional pied-à-terre. Enjoy two bedrooms and two bathrooms on separate levels, with tremendous privacy and rear alley access. Easy access to nearby parks is perfect for leisurely strolls. Convenient public services and amenities are just a stone's throw away, making daily errands a breeze. Whether you're exploring local shops or enjoying a meal nearby, you'll find everything you need within reach.

$525,000

2 beds2 baths851 sq ft

806 Calvert Ave, St Michaels, MD 21663

Nearby parks • Rear alley access • Public services

(410) 822-1415

OPEN SAT, 10AM TO 12PMFLOOR PLAN

$795,000

4 beds3.5 baths2,955 sq ft

7964 Pond Haven Ct, St Michaels, MD 21663

0.39 acre lot • 2 garage spots • Built 2004

(410) 745-0283

ABOUT THIS HOME
St. Michaels, MD Homes for Sale
This property has been gutted and the floor joists replaced, new Advantac subfloor installed, drywall removed, new interior framing, new roof, insulation, new electric and a new sewer line to the street. . The hard work has been done. It's ready for you to make it your own. Off street parking and large rear yard. Please be careful showing as there is still building materials on the property.

$329,000

3 beds1.5 baths1,312 sq ft

409 Railroad Ave, St Michaels, MD 21663

7,405 sq ft lot • Built 1957 • Listed 2 days

(410) 829-3603

NEW 9 HRS AGO

$279,000

3 beds2 baths1,340 sq ft

210 Brooks Ln, St Michaels, MD 21663

Vinyl siding • 0.17-acre lot • Outdoor space

(410) 745-8060

ABOUT THIS HOME
St. Michaels, MD Homes for Sale
Extraordinary waterfront living on 3+ acres with more than 500 feet of stunning water views—offering the privacy of being miles from civilization, yet just 1 mile from famed, historic downtown St. Michaels. Extensively renovated and meticulously cared for, this exceptional one-level living residence provides relaxed comfort, thoughtful design and effortless living in a a resort-like setting. Its westerly orientation delivers spectacular sunsets every evening, complemented by expansive water views and abundant wildlife. Offered completely turnkey—furnishings, linens, fully equipped kitchen and everything shown in the photographs convey. Additional features include a saltwater poo

$3,000,000

4 beds3 baths2,815 sq ft

23820 Mount Pleasant Lndg, St Michaels, MD 21663

Saltwater pool • Pool house • 3.4 acres

(443) 292-6767

Property at 301 Lincoln Ave, St Michaels, MD 21663, 3 beds, 2 baths

$474,900

3 beds2 baths1,472 sq ft

301 Lincoln Ave, St Michaels, MD 21663

(443) 274-1900

Property at 111 Chesapeake Ave, St Michaels, MD 21663, 4 beds, 2.5 baths

$949,000

4 beds2.5 baths2,168 sq ft

111 Chesapeake Ave, St Michaels, MD 21663

(410) 822-6272

Property at 105 Marengo St, St Michaels, MD 21663, 3 beds, 1 bath

$299,900

3 beds1 bath1,656 sq ft

105 Marengo St, St Michaels, MD 21663

(410) 544-2931

Property at 114 W Chestnut St, St Michaels, MD 21663, 4 beds, 4 baths

$1,195,000

4 beds4 baths3,528 sq ft

114 W Chestnut St, St Michaels, MD 21663

(410) 745-2596

Property at 214 Madison Ave, St Michaels, MD 21663, 4 beds, 2 baths

$375,000

4 beds2 baths1,743 sq ft

214 Madison Ave, St Michaels, MD 21663

(410) 266-0600

Property at 407 Seymour Ave, St Michaels, MD 21663, 4 beds, 3.5 baths

$799,950

4 beds3.5 baths2,154 sq ft

407 Seymour Ave, St Michaels, MD 21663

(410) 822-1415

Property at 9521 Quail Hollow Dr #605, St Michaels, MD 21663, 3 beds, 3 baths

$490,000

3 beds3 baths1,752 sq ft

9521 Quail Hollow Dr #605, St Michaels, MD 21663

(410) 745-0415

Property at 7963 Pond Haven Ct, St Michaels, MD 21663, 3 beds, 2.5 baths

$655,000

3 beds2.5 baths3,010 sq ft

7963 Pond Haven Ct, St Michaels, MD 21663

(410) 745-0283

Property at 202 E Chestnut St, St Michaels, MD 21663, 3 beds, 3 baths

$1,250,000

3 beds3 baths2,052 sq ft

202 E Chestnut St, St Michaels, MD 21663

(410) 745-0415

Property at 104 Mulberry St, Saint Michaels, MD 21663, 3 beds, 2.5 baths

$1,399,000

3 beds2.5 baths1,938 sq ft

104 Mulberry St, Saint Michaels, MD 21663

(410) 224-4400

Property at 24362 Widgeon Pl #5, St Michaels, MD 21663, 2 beds, 2 baths

$368,000

2 beds2 baths1,800 sq ft

24362 Widgeon Pl #5, St Michaels, MD 21663

(410) 745-8060

Property at 204 E Marengo St, St Michaels, MD 21663, 2 beds, 1 bath

$539,900

2 beds1 bath1,200 sq ft

204 E Marengo St, St Michaels, MD 21663

(410) 429-7425

Property at 8000 Bozman Neavitt Rd, Bozman, MD 21612, 3 beds, 2 baths

$439,000

3 beds2 baths1,761 sq ft

8000 Bozman Neavitt Rd, Bozman, MD 21612

(410) 745-0415

Property at 101 Mulberry St, St Michaels, MD 21663, 4 beds, 2.5 baths

$1,129,000

4 beds2.5 baths1,500 sq ft

101 Mulberry St, St Michaels, MD 21663

(410) 822-6272

Property at 8090 Bozman Neavitt Rd, Bozman, MD 21612, 3 beds, 2 baths

$939,000

3 beds2 baths1,362 sq ft

8090 Bozman Neavitt Rd, Bozman, MD 21612

(410) 822-6665

Property at 104 Madison Ave, St Michaels, MD 21663, 4 beds, 3 baths

$459,900

4 beds3 baths2,420 sq ft

104 Madison Ave, St Michaels, MD 21663

(410) 822-6665

Property at 303 Manor, St Michaels, MD 21663, 3 beds, 3 baths

$1,950,000

3 beds3 baths2,622 sq ft

303 Manor, St Michaels, MD 21663

(410) 745-2596

Property at 24700 Deepwater Pt #20, St Michaels, MD 21663, 2 beds, 2.5 baths

$385,000

2 beds2.5 baths1,477 sq ft

24700 Deepwater Pt #20, St Michaels, MD 21663

(410) 745-2596

Property at 9531 Quail Hollow Dr #405, St Michaels, MD 21663, 2 beds, 2.5 baths

$339,900

2 beds2.5 baths1,800 sq ft

9531 Quail Hollow Dr #405, St Michaels, MD 21663

(410) 822-6665

Property at 807 Radcliff Ave, St Michaels, MD 21663, 3 beds, 2.5 baths

$775,000

3 beds2.5 baths2,027 sq ft

807 Radcliff Ave, St Michaels, MD 21663

(301) 945-9010

Property at 228 Perry Cabin Dr Unit 228 / 226, St Michaels, MD 21663, 6 beds, 6 baths

$1,945,000

6 beds6 baths4,089 sq ft

228 Perry Cabin Dr Unit 228 / 226, St Michaels, MD 21663

(410) 829-3603

Property at 109 W Marengo St, St Michaels, MD 21663, 4 beds, 3 baths

$995,000

4 beds3 baths2,250 sq ft

109 W Marengo St, St Michaels, MD 21663

(410) 822-6665

Property at 9020 Bozman Neavitt Rd, St Michaels, MD 21663, 4 beds, 2.5 baths

$1,995,000

4 beds2.5 baths3,028 sq ft

9020 Bozman Neavitt Rd, St Michaels, MD 21663

(410) 745-0415

Property at 204 Lincoln, St Michaels, MD 21663, 3 beds, 2 baths

$598,000

3 beds2 baths2,348 sq ft

204 Lincoln, St Michaels, MD 21663

(410) 745-0283

Property at 9180 Saint Michaels, St Michaels, MD 21663, 5 beds, 5 baths

$1,685,000

5 beds5 baths4,728 sq ft

9180 Saint Michaels, St Michaels, MD 21663

(410) 745-0283

Property at 7909 Church Nck, St Michaels, MD 21663, 4 beds, 2.5 baths

$2,000,000

4 beds2.5 baths4,492 sq ft

7909 Church Nck, St Michaels, MD 21663

(410) 745-2596

Property at 8620 Bozman Neavitt, St Michaels, MD 21663, 6 beds, 9 baths

$8,495,000

6 beds9 baths17,402 sq ft

8620 Bozman Neavitt, St Michaels, MD 21663

(202) 944-5000

Property at 108 Miles Ave, St Michaels, MD 21663, 3 beds, 2 baths

$779,000

3 beds2 baths1,710 sq ft

108 Miles Ave, St Michaels, MD 21663

(410) 822-6665

Property at 9518 Quail Holw #702, St Michaels, MD 21663, 3 beds, 3 baths

$455,000

3 beds3 baths1,800 sq ft

9518 Quail Holw #702, St Michaels, MD 21663

(410) 822-1415

Property at 7865 Pea Nck, St Michaels, MD 21663, 4 beds, 3.5 baths

$1,379,800

4 beds3.5 baths3,332 sq ft

7865 Pea Nck, St Michaels, MD 21663

(410) 822-6272

Property at 1215 Washington, St Michaels, MD 21663, 4 beds, 3 baths

$499,000

4 beds3 baths2,420 sq ft

1215 Washington, St Michaels, MD 21663

(410) 745-0283

Property at 1211 Washington, St Michaels, MD 21663, 4 beds, 3 baths

$499,000

4 beds3 baths2,420 sq ft

1211 Washington, St Michaels, MD 21663

(410) 745-0283

Property at Lot 16A Meadow St, Saint Michaels, MD 21663, 4 beds, 2.5 baths

$799,000

4 beds2.5 baths— sq ft

Lot 16A Meadow St, Saint Michaels, MD 21663

(410) 729-7700

Property at 912 Calvert Ave, St Michaels, MD 21663

$199,000

Land0.25 acre (lot)

912 Calvert Ave, St Michaels, MD 21663

(410) 745-0415

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Average home prices near St. Michaels, MD

Cities

Zip Codes

21663 homes for sale
$799,000

St. Michaels, MD real estate trends

All Home Types trends in St. Michaels, MD

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$1,309,134

+127.7% YoY | Aug 2026

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Aug 2026

Growth

% YoY

St. Michaels, MD

$1,309,134

+127.7%

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