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A rare opportunity in the heart of St. Michaels: this half-acre+ wooded parcel offers the privacy of a tucked-away retreat with the everyday convenience of an in-town location. Restaurants, shops, seasonal events, waterfront parks, and the character of the historic district are all close at hand, yet the setting feels quiet and natural. Approximately three times the size of a typical in-town lot, the property provides remarkable flexibility for home placement, architectural style, and outdoor living spaces. The generous buildable envelope allows for a variety of layouts, and driveway access can be configured from Miles Avenue, Canton Street, or both, depending on the design. Infrastructure upgrades are already complete, including paved roads, a State-approved gravel extension, town water, county sewer, electric service, and fiber-optic internetallowing for a smoother path from planning to construction. With the appropriate Town approvals, the parcel also offers future subdivision potential. Adjacent to the scenic Rails-to-Trails corridor and near San Domingo Creek, the Miles River, and multiple neighborhood parks, the location provides access to nature and open space without giving up the benefits of being in town. Architectural concept drawings illustrating one potential approach to the site will convey to the new owner, with the option to continue working with the original architect if desired. A unique chance to create something truly exceptional in one of the Eastern Shores most sought-after communities: space, privacy, and the freedom to design a home that reflects your visionBy Vehicle: A portion of Canton St is a one-way and Miles Ave is not a completely through Street from Railroad Ave. It is recommended to head north on Talbot St., turn left on Railroad Ave., then left on Glory Ave (also known as Gloria), and right on Canton St. Proceed a short way to the corner of the lot at Miles Ave. & Canton St.
By Vehicle: A portion of Canton St is a one-way and Miles Ave is not a completely through Street from Railroad Ave. It is recommended to head north on Talbot St., turn left on Railroad Ave., then left on Glory Ave (also known as Gloria), and right on Canton St. Proceed a short way to the corner of the lot at Miles Ave. & Canton St.
Source: School Digger
St. Michaels Elementary School
Public • PK - 5 • Serves this home
Distance
St. Michaels Middle/high School
Public • 6 - 12 • Serves this home
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Public • 9 - 12 • Serves this home
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St. Michaels Elementary School
Public • PK - 5 • Serves this home
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Chapel District Elementary School
Public • PK - 5
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St. Michaels Middle/high School
Public • 6 - 12 • Serves this home
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Public • 6 - 8
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Public • 9 - 12 • Serves this home
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Source: Public Records
| Street Address | Beds | Baths | Sold Date | List Price | Valuation Date | Valuation Price |
|---|---|---|---|---|---|---|
| 132 TALBOT ROAD | 3 | 2 | Nov 18, 2025 | $315,000 | Nov 25, 2025 | - |
| 418 NORTH STREET | Listing | 3 | 2 | Nov 11, 2025 | $295,000 | Mar 21, 2024 | $272,456 |
| 602 S TALBOT STREET | Listing | 4 | 3 | Oct 03, 2025 | $800,000 | Mar 21, 2024 | $254,634 |
| 28799 SPRINGFIELD DRIVE | 5 | 5 | Oct 29, 2025 | $1,795,000 | Nov 25, 2025 | - |
| 1 LEE TERRACE | Listing | - | 0 | Oct 29, 2025 | $849,900 | Mar 21, 2024 | $332,322 |
| 103 WRIGHTSON AVENUE | Listing | 2 | 1 | Oct 29, 2025 | $350,000 | Mar 21, 2024 | $336,609 |
| 25070 HURLEY LANE | 3 | 3 | Nov 10, 2025 | $439,999 | Nov 25, 2025 | - |
| 11 SANDY LN | 3 | 2 | Oct 18, 2025 | $675,000 | Nov 25, 2025 | - |
| 9175 MALLARD POINT COURT | 4 | 3 | Oct 09, 2025 | $1,499,900 | Nov 25, 2025 | - |
| 311 SALMON AVENUE | 3 | 2 | Oct 18, 2025 | $415,000 | Nov 25, 2025 | - |
Source: Sperling's Best Places
| Zip | City | County | National | |
|---|---|---|---|---|
| Population | 3,325 | 3,325 | 38,548 | 335,858,263 |
| Population Density | 282 | 282 | 144 | 95 |
| People per Household | 2.1 | 2.1 | 2.3 | 2.6 |
| Median Age | 59.6 | 59.6 | 48.4 | 39.1 |
| Median Income | $79,912 | $79,912 | $76,468 | $66,222 |
| Average Income | $63,198 | $63,198 | $48,812 | $35,475 |
| Cost of Living Index | 81 | 81 | 88 | 100 |
| Zip | City | County | National | |
|---|---|---|---|---|
| January Avg. High Temp | 28.4°F | 28.4°F | 28.4°F | 22.6°F |
| July Avg. High Temp | 88°F | 88°F | 88°F | 86.2°F |
| Annual Precipitation | 45.87" | 45.87" | 45.87" | 38" |
8/100
Walk Score ®
47/100
Bike Score ®
The average walkability score in the surrounding area is Walk Score: 3/100, Transit Score: 0/100, Bike Score: 28/100.
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4 bds • 3 ba • 1,957 sqft
408 SPINNAKER LANE, SAINT MICHAELS, MD 21663
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3 bds • 2 ba • 1,932 sqft
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4 bds • 3 ba • sqft
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4 bds • 4 ba • 3100 sqft
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3 bds • 3 ba • 3166 sqft
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3 bds • 3 ba • 2496 sqft
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3 bds • 2 ba • 1761 sqft
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26972 TUNIS MILL ROAD
Source: Realty.com
108 MILES AVENUE, SAINT MICHAELS, MD 21663 is a Single Family 1,710 sq. ft. home listed for sale. Realty.com has 6 photos available of this 3 bed, 2 bath house, listed at $779,000. View sales and tax history, use our mortgage calculator and more on Realty.com
Realty.com has 6 photos of 108 MILES AVENUE.
The full address for this home is 108 MILES AVENUE, SAINT MICHAELS, MD 21663.
108 MILES AVENUE has been listed on Realty.com since Thu November 20, 2025
Almost all errands require a car. It is possible to get on a bus. Minimal bike infrastructure.
The average walkability score in the surrounding area is Walk Score: 3/100, Transit Score: 0/100, Bike Score: 28/100.
There are 3 schools assigned to this home. Check out the schools near 108 MILES AVENUE. St. Michaels Elementary School (Grades: PK - 5), St. Michaels Middle/high School (Grades: 6 - 12), Easton High School (Grades: 9 - 12)
Listing provided courtesy of:
Benson & Mangold, Llc
(tel: 410-770-9255)
Listing agent:
Chuck Mangold Jr.
(tel: 410-924-8832)
(#67893)
This content last refreshed on 2025-11-25 16:36:27. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.
Export listing data of 108 MILES AVENUE, SAINT MICHAELS, MD 21663 : MLS# MDTA2012358