St. Michaels, MD homes for sale & real estate

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23762 Mount Pleasant Lndg, Saint Michaels, MD 21663
23762 Mount Pleasant Lndg, Saint Michaels, MD 21663
23762 Mount Pleasant Lndg, Saint Michaels, MD 21663
ABOUT THIS HOME
St. Michaels, MD Homes for Sale
Coastal Point Perfection – A re-imagined, fully furnished, and turn-key, short-term rental, second home, or primary residence waterfront retreat opportunity within walking and biking distance of the Town of Saint Michael's. Tucked at the end of a private, tree-lined lane and wrapped in over 700 feet of panoramic waterfront, this exceptional property has been completely transformed from its 1965 brick ranch origins into a timeless coastal cottage retreat. Positioned on a prime point of land, this home offers the ultimate in privacy, waterfront lifestyle, and design sophistication. The exterior has been thoughtfully appointed with new board-and-batten siding, an architectural shingle ro

$2,995,000

4 beds4.5 baths2,649 sq ft

23762 Mount Pleasant Lndg, Saint Michaels, MD 21663

3.41 acre lot • Pool • Car-dependent

(443) 746-2090

24977 Back Creek Dr, Saint Michaels, MD 21663
24977 Back Creek Dr, Saint Michaels, MD 21663
24977 Back Creek Dr, Saint Michaels, MD 21663
ABOUT THIS HOME
St. Michaels, MD Homes for Sale
Discover this exquisite custom-built retreat in the serene St. Michaels community, a perfect blend of luxury and comfort with 4 spacious bedrooms and 3.5 well-appointed bathrooms, packed with premium features for an elevated lifestyle. Cozy up to the versatile gas fireplace, while enjoying a spacious layout enhanced with numerous built-ins for style and function. The expansive primary suite boasts a massive walk-in closet and an oversized bathroom with a huge custom shower and new faucets, complemented by a second-floor ensuite primary or guest suite for family or visitors. Step outside to the sprawling Trex deck with a Sunsetter awning, ideal for relaxing or entertaining, all within a full

$779,500

4 beds3.5 baths3,010 sq ft

24977 Back Creek Dr, Saint Michaels, MD 21663

0.27 acre lot • $100 HOA • 2 garage spots

(410) 822-6665

LISTED BY REDFIN3D WALKTHROUGH

1221 Washington, Saint Michaels, MD 21663
1221 Washington, Saint Michaels, MD 21663
1221 Washington, Saint Michaels, MD 21663
ABOUT THIS HOME
St. Michaels, MD Homes for Sale
ASSUMABLE USDA LOAN AT 3.25%! Charm meets modern luxury in this beautifully appointed Cape Cod nestled in the desirable Rio Vista community of historic Saint Michaels. This thoughtfully designed 4 bedroom, 3 full bath two-story home is situated on a . 34 acre setting and seamlessly blends traditional architecture with contemporary amenities, creating an inviting space perfect for both everyday living and entertaining. As you approach you'll be immediately captivated by the private setting. Nestled at the tranquil end of a street, the property offers an enviable sense of privacy and exclusivity. An expansive parking area greets you, generously accommodating multiple vehicles with ease &ndash

$515,000

4 beds3 baths1,848 sq ft

1221 Washington, Saint Michaels, MD 21663

0.34 acre lot • $4 HOA • Car-dependent

9791 Pintail Pl, Saint Michaels, MD 21663
9791 Pintail Pl, Saint Michaels, MD 21663
9791 Pintail Pl, Saint Michaels, MD 21663
ABOUT THIS HOME
St. Michaels, MD Homes for Sale
Welcome to Rivermark - a true waterfront retreat in St. Michaels on the Eastern Shore. This custom-built home is an artistic masterpiece with five octagonal interconnected wings, creating distinct yet flowing spaces and breathtaking panoramic views of Porters Creek, Miles River, Wye River and the Eastern Bay from every room. With architecture inspired by the French West Indies, this home has been thoughtfully designed with both entertainment and relaxation in mind. Entering through the foyer, the heart of the home is the Great Room which contains soaring ceilings. This opens to a sun-drenched solarium with travertine flooring and floor-to-ceiling windows that wrap around the interconnected

$3,475,000

5 beds5 baths7,300 sq ft

9791 Pintail Pl, Saint Michaels, MD 21663

2 acre lot • $15 HOA • 2 garage spots

(301) 298-1001

NEW CONSTRUCTION

110 Lee St, Saint Michaels, MD 21663
110 Lee St, Saint Michaels, MD 21663
110 Lee St, Saint Michaels, MD 21663
ABOUT THIS HOME
St. Michaels, MD Homes for Sale
Welcome to 110 Lee Street, a brand-new single-level home tucked away in the heart of charming St. Michaels, Maryland. Thoughtfully designed and just completed in 2024, this home captures the perfect balance of modern elegance and small-town warmth, offering a lifestyle that’s as relaxed as it is refined. Step inside and experience an open-concept floor plan that effortlessly connects the living, dining, and kitchen areas. Natural light fills the space, highlighting designer finishes and a welcoming atmosphere. The kitchen is a showstopper—equipped with sleek quartz countertops, stainless steel appliances, and custom cabinetry that make it both stylish and functional. A cozy gas

$495,000

3 beds2 baths1,500 sq ft

110 Lee St, Saint Michaels, MD 21663

7,767 sq ft lot • Somewhat walkable

(877) 366-2213

Property at 204 W Chew Ave, Saint Michaels, MD 21663, 3 beds, 2 baths

$699,000

3 beds2 baths1,500 sq ft

204 W Chew Ave, Saint Michaels, MD 21663

(410) 829-3603

Property at 205 E Chew, Saint Michaels, MD 21663, 2 beds, 1.5 baths

$1,349,000

2 beds1.5 baths1,780 sq ft

205 E Chew, Saint Michaels, MD 21663

(410) 822-6665

Property at 24749 Swan Rd, Saint Michaels, MD 21663, 3 beds, 2.5 baths

$720,000

3 beds2.5 baths2,496 sq ft

24749 Swan Rd, Saint Michaels, MD 21663

(410) 745-0415

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

$8,495,000

6 beds9 baths17,402 sq ft

8620 Bozman Neavitt, Saint Michaels, MD 21663

(202) 944-5000

Property at 103 W Marengo, Saint Michaels, MD 21663, 2 beds, 1.5 baths

$565,000

2 beds1.5 baths1,209 sq ft

103 W Marengo, Saint Michaels, MD 21663

(410) 745-2596

Property at 400 Railroad, Saint Michaels, MD 21663, 3 beds, 2 baths

$549,000

3 beds2 baths1,674 sq ft

400 Railroad, Saint Michaels, MD 21663

(410) 745-2596

Property at 901 S Talbot, Saint Michaels, MD 21663, 3 beds, 2 baths

$659,000

3 beds2 baths1,660 sq ft

901 S Talbot, Saint Michaels, MD 21663

(410) 822-1415

Property at 1026 Riverview Ter, Saint Michaels, MD 21663, 4 beds, 3 baths

$1,350,000

4 beds3 baths2,535 sq ft

1026 Riverview Ter, Saint Michaels, MD 21663

(410) 745-0415

Property at 9171 Deepwater Point Rd, Saint Michaels, MD 21663, 4 beds, 3.5 baths

$1,695,000

4 beds3.5 baths4,102 sq ft

9171 Deepwater Point Rd, Saint Michaels, MD 21663

(410) 228-0800

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

$649,900

2 beds1 bath1,200 sq ft

204 E Marengo, Saint Michaels, MD 21663

(410) 429-7425

Property at 112 Mitchell St, Saint Michaels, MD 21663, 3 beds, 1 bath

$299,000

3 beds1 bath1,368 sq ft

112 Mitchell St, Saint Michaels, MD 21663

(410) 829-3603

Property at 8034 Bozman Neavitt Rd, Bozman, MD 21612, 2 beds, 1 bath

$189,900

2 beds1 bath1,160 sq ft

8034 Bozman Neavitt Rd, Bozman, MD 21612

(443) 320-1344

Property at Lot 2 Meadow St, Saint Michaels, MD 21663, 4 beds, 3.5 baths

$889,800

4 beds3.5 baths3,100 sq ft

Lot 2 Meadow St, Saint Michaels, MD 21663

(410) 729-7700

Property at 103 Mulberry St, Saint Michaels, MD 21663, 4 beds, 1.5 baths

$875,000

4 beds1.5 baths1,596 sq ft

103 Mulberry St, Saint Michaels, MD 21663

(410) 745-0415

Property at 7369 Drum Point Rd, Saint Michaels, MD 21663, 3 beds, 2.5 baths

$1,995,000

3 beds2.5 baths3,562 sq ft

7369 Drum Point Rd, Saint Michaels, MD 21663

(410) 822-6272

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 216 Chew E, Saint Michaels, MD 21663, 4 beds, 3.5 baths

$1,899,000

4 beds3.5 baths3,575 sq ft

216 Chew E, Saint Michaels, MD 21663

(410) 745-2596

Property at 24560 Deepwater Pt #1, Saint Michaels, MD 21663, 2 beds, 2 baths

$369,000

2 beds2 baths1,296 sq ft

24560 Deepwater Pt #1, Saint Michaels, MD 21663

(410) 745-0415

Property at 25070 Hurley Ln, Saint Michaels, MD 21663, 3 beds, 2.5 baths

$475,000

3 beds2.5 baths1,505 sq ft

25070 Hurley Ln, Saint Michaels, MD 21663

(410) 770-3600

Property at 24629 Beverly Rd, Saint Michaels, MD 21663, 5 beds, 5.5 baths

$9,950,000

5 beds5.5 baths10,309 sq ft

24629 Beverly Rd, Saint Michaels, MD 21663

(410) 822-6272

Property at 108 Miles Ave, Saint Michaels, MD 21663

$495,000

— beds— baths— sq ft

108 Miles Ave, Saint Michaels, MD 21663

(410) 822-6272

Property at 402 Talbot, Saint Michaels, MD 21663

$140,000

— beds— baths— sq ft

402 Talbot, Saint Michaels, MD 21663

(302) 703-1144

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Average home prices near St. Michaels, MD

Cities

Zip Codes

21663 homes for sale
$875,000

St. Michaels, MD real estate trends

$1.82M

Sale price

+91.3%
since last year

$557

Sale $/sq ft

+37.3%
since last year

Under list price

Days on market

Down payment

—

Total homes sold

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