Features & Amenities

Interior

  • Other Interior Features

    Eat-in Kitchen, Built-in Features

  • Total Bedrooms

    2

  • Bathrooms

    2

  • 1/2 Bathrooms

    1

  • Above Grade Finished Area

    1445.0

  • Basement YN

    NO

  • Cooling YN

    YES

  • Cooling

    Central Air, Electric

  • Fireplace YN

    YES

  • Heating YN

    YES

  • Heating

    Electric, Heat Pump

  • Main Level Bedrooms

    1

  • Pet friendly

    N/A

Exterior

  • Garage

    No

  • Construction Materials

    Asbestos, Shingle Siding

  • Other Exterior Features

    Barbecue

  • Parking

    Off Street

  • Pool

    Yes

  • Pool Features

    None

  • Waterfront YN

    NO

Area & Lot

  • Lot Size(acres)

    0.18

  • Property Type

    Residential

  • Property Sub Type

    Single Family Residence

  • Architectural Style

    Cottage

Price

  • Sales Price

    $1,099,000

  • Tax Amount

    5764.0

  • Sq. Footage

    1, 445

  • Price/SqFt

    $760

HOA

  • Association

    No

School District

  • Elementary School

    N/A

  • Middle School

    N/A

  • High School

    N/A

Property Features

  • Senior Community YN

    NO

  • Sewer

    Public Sewer

  • Water Source

    Public

Schedule a Showing

Showing scheduled successfully.

<
>
IN PERSON
VIA CHAT

What is 3 + 4 ?


Change time

Mortgage calculator

Estimate your monthly mortgage payment, including the principal and interest, property taxes, and HOA. Adjust the values to generate a more accurate rate.

Your payment

Principal and Interest:

$

Property taxes:

$

HOA fees:

$

Total loan payment:

$

Total interest amount:

$

Location

County

TALBOT

Elementary School

Middle School

High School

Listing Courtesy of Debra S Crouch , Benson & Mangold, LLC

RealHub Information is provided exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All information deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change or withdrawal. RealHub website owner shall not be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless.

Agent CatieSnider

AGENT

CatieSnider

Call Catie today to schedule a private showing.


* Listings on this website come from the FMLS IDX Compilation and may be held by brokerage firms other than the owner of this website. The listing brokerage is identified in any listing details. Information is deemed reliable but is not guaranteed. If you believe any FMLS listing contains material that infringes your copyrighted work please click here to review our DMCA policy and learn how to submit a takedown request.© 2024 FMLS.
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 opportunity!

100 GRACE STREET

Message successfully sent.

What would you like to know?

What is 3 + 4 ?

Related Properties

Welcome to Old House Cove Waterfront Retreat  in St. Michaels, MD
Nestled on nearly half an acre with scenic frontage along Old House Cove, this quintessential Eastern Shore property offers a rare combination of waterfront serenity, literary history, and timeless design. The expansive parcel provides privacy in a highly desirable location, just minutes from the heart of St. Michael’s—one of Maryland’s most beloved waterfront towns.
Formerly owned by the poet and author Gilbert Byron who was often called “the Chesapeake Thoreau,” it is easy to see how the tranquil setting on Old House Cove inspired much of his writing. Originally built in 1965, the main house has been thoughtfully updated to blend classic Eastern Shore style with relaxed modern comfort. The open-concept kitchen, dining, and living area centers around a gas fireplace - all with sweeping water views. Added in 1993, the spacious primary suite features a walk-in closet and en-suite bath. The waterside screened porch is the perfect place to unwind, enjoy the gentle breeze off the water and watch sailboats glide across the cove toward San Domingo Creek. 
Connected to the main home by a charming pergola walkway, the large carriage house and garage—also constructed in 1993 —includes two bays, one with double doors for boat access. The upper-level guest suite feels like a private treehouse retreat, complete with its own deck and sweeping views of the cove. Together, the main residence and guest suite create an ideal opportunity to expand the property and craft the waterfront home of your dreams—offering privacy, flexibility, and direct access to the property’s stunning setting.
Outdoor living is a true highlight of this property. A generous brick terrace provides the perfect space for alfresco dining or entertaining just steps from the water’s edge. The property features approximately 130 feet of rip-rapped shoreline, a sandy kayak launch area, and a private pier equipped with one slip and 2.5’ MLW—ideal easy access to the Bay.
Beautiful mature trees, lush landscaping, and a circular drive create an estate-like approach. The property is served by two wells and two septic systems, and sits comfortably in Flood Zone X (no flood insurance required). The area has been approved for public sewer hookup, offering excellent potential for future expansion or reconfiguration to suit your vision.
This is a rare opportunity to own a timeless waterfront retreat—where Eastern Shore charm, literary heritage, and modern comfort come together just minutes from the world-class dining, sailing, and small-town allure of St. Michaels, Maryland.
#MDTA2012154

SAINT MICHAELS

24318 OAKWOOD PARK ROAD

3 Beds

3 Baths

2,085 Sq.Ft.

$1,195,000

MLS#: MDTA2012154

Fabulous St. Michaels location near Miles River, St. Michaels Marina, Inn & Spa, St, Michael’s Winery, area schools and so much more! Enjoy all the benefits of a coastal lifestyle in this charming & scenic historic town. Build your dream home on a attractive homesite minutes from everything and everywhere you want to be.
The Pointe offers an impressive open kitchen with island, pantry and large dining area perfect for all those gatherings and get-togethers. A very spacious great room is adjacent to the cooking and dining area. The main level also offers a welcoming foyer and 2-car garage. Upstairs you’ll find a tranquil owner’s suite with a large walk-in closet and bath featuring dual sinks, soaking tub and walk-in shower. Three additional bedrooms, hall bath and laundry room complete the second floor. An optional full basement provides ample living and storage space including an opt. rec room, opt. media room, opt. fifth and sixth bedrooms, and a third or fourth full bath!
#MDTA2009828

SAINT MICHAELS

704 MEADOW STREET

4 Beds

3 Baths

3,100 Sq.Ft.

$889,800

MLS#: MDTA2009828

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 internet—allowing 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 Shore’s most sought-after communities: space, privacy, and the freedom to design a home that reflects your vision. 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.
#MDTA2012368

SAINT MICHAELS

108 MILES AVENUE

3 Beds

2 Baths

N/A

$999,000

MLS#: MDTA2012368

New on site 4 days ago
Welcome to this luxurious, waterfront townhouse in the beautiful town of St. Michaels!  This is the absolute total package, offering turn key comfort in a centralized location, allowing you to maximize everything the eastern shore has to offer.  Enjoy the views of the majestic Miles River, boating from your personal, deeded boat slip, or walk across the street to the Eastern Shore's most premier golf course!  This expansive unit offers premium upgraded finishes, a first floor ensuite bedroom, fireplace, and endless enhancements, including new windows and completely new HVAC system.  Minutes to town for shopping or award winning dining experiences.  This is truly the perfect waterfront, low maintenance getaway that is sure to check all of the boxes of a dream home!
#MDTA2012490

SAINT MICHAELS

9792 MARTINGHAM CIRCLE B-4

3 Beds

3 Baths

2,135 Sq.Ft.

$975,000

MLS#: MDTA2012490

St. Michaels charm in this Circa 1870 Certified Plaque home, although historical data reflects original construction between 1805-1820.Updates include plumbing ,wiring, New upstairs HVAC, encapsulated crawl space, kitchen ,upgraded light fixtures, motorized window shades and many architectural details, freshly painted in 2024 . Recently upgraded Primary bedroom window seats with cushions, built-ins and storage. Magnificent main level 2 story glass enclosed solarium! This home has been meticulously  maintained  and cared for. Enjoy evenings on the front porch or on the rear screen porch overlooking the gardens. The rear yard also has an old time boat house/shed which is insulated and heated and the current owners have gone through the local Historic approvals to renovate the boathouse/shed into a guest house. See documents for plans and drawings. Convenient walking distance to St. Michaels Harbor, Chesapeake Bay Maritime Museum, and numerous shops and great restaurants. This home is Gem so don't miss out on this opportunity!
#MDTA2011802

SAINT MICHAELS

107 E CHESTNUT STREET

2 Beds

2 Baths

2,024 Sq.Ft.

$1,195,000

MLS#: MDTA2011802

 - property

Send a message

Message successfully sent.

Your message

What is 3 + 4 ?

Reason for contacting?

Sign Out

Virtual Assistant

Would you like to take the next step with this property? We can help you schedule a showing or virtual tour, or send you more details.

Yes, I would like more information.

Thank You for Your Reply, One of Our Agents will contact you as soon as possible

No, maybe later.

Thank you, you can always contact me via email, phone number or through the contact form.

Realhub AI

Lucy - Your AI-Powered Realtor

Update Your Temporary Password

Personalize your search

Enter your email and we'll notify you immediately when new listings match what you're looking for.

or enter email address

Already have an account ? Login here

Continue your home search

Already have an account ? Login here

We use cookies

We use cookies primarily for analytics to enhance your experience. By accepting, you agree to our use of these cookies. You can manage your preferences or learn more about our cookies policy.