Sherwood MD Real Estate & Commercial for Sale

*A Once-in-a-Lifetime Chesapeake Bay Waterfront Offering - The Iconic Tilghman Island Inn* Welcome to a rare opportunity to own one of the most beautiful, fully reimagined waterfront hospitality properties on Marylands Eastern Shore. Set on five acres with sweeping views of the Chesapeake Bay, the Tilghman Island Inn is that extraordinary blend of romance, lifestyle, and investment that rarely becomes available. Established more than 50 years ago, the Inn has been transformed from top to bottom through a meticulous, comprehensive renovation. Today, it lives as a boutique luxury retreat with 20 uniquely designed guest rooms (five with gas fireplaces), a full-service waterfront restaurant and bar, expansive outdoor dining terraces, a sparkling 20' x 40' pool, lush gardens, and expansive private docking with the relaxed charm and quiet sophistication that define the Chesapeake Bay. Guests return year after year for the Inns serenity, sunset views, on-site dining, and proximity to St. Michaels, Easton, and Annapolis. For buyers, the value is just as clear: major improvements are already complete, systems are up to date, and recent guest ratings average about 95% across major travel platforms. Whether you envision this as a turnkey boutique hotel, a private family compound, a luxury event destination, or a future waterfront condominium development, the property is positioned for success. The Inn is legally configured as 20 residential condominium units offering flexibility. Property Features: 5-acre waterfront property, 15,000+ sq. ft. hotel and restaurant, 345 ft. vinyl seawall, 20 x 30 ft. T-Dock, 175 ft. floating dock with 7 additional boat slips, 20 uniquely designed guest rooms, 20 x 40 ft. in-ground pool, 30 x 12 ft. fully functional greenhouse, and Lush ornamental and raised bed vegetable gardens For investors seeking a premier turnkey hospitality venture or a high-value waterfront development opportunity, the Tilghman Island Inn presents a rare chance to own an Eastern Shore gem with limitless potential. **NOTE: FOR BROCHURE & VIDEO CONTACT AGENT**

The former "Bozman General Store and Post Office," is located just 5 miles outside St. Michaels. Zoned Village Commercial, this high-visibility property offers many potential commercial uses: General store; construction contractor's office; boat or auto repair; private office; etc. There is an existing modern well and an older septic system. Public sewer connection projected to be available in 2026. The 1,200 sq ft block building was constructed in 1965. In 2025, the old floors were removed and new floor joists and subfloor were installed. At the same time, the roof rafters were sistered and the ceiling height raised to 9 ft., with all-new ceiling rafters. The building is offered in "as-is" condition.

Rental Opportunity in Wittman, MD Positioned in the desirable community of Wittman, this 3 bedroom, 2 bath home on 0.84± commercially zoned acreage with premier road frontage presents a compelling opportunity for investors seeking rental income in Talbot County. The property offers comfortable living space, a rural Eastern Shore setting, and proximity to key employment, recreation, and service hubs. In addition to the primary residence, the property includes two detached outbuildings. One is ideal for storage or retail use, and another is suited for workshop or auto repair. The lot provides open space with ample parking and a private setting while remaining conveniently located near St. Michaels, Easton, and Tilghman Island. Investment Highlights � 3 Bedrooms 2 Bathrooms split between two units � 0.84± acre parcel with generous yard space � Two accessory structures (retail/storage in need of repair + versatile workshop ) � Strong long-term rental market supported by local workforce and regional amenities � Minutes to marinas, dining, recreation, and Chesapeake Bay attractions � Quiet rural location with easy access to surrounding towns and services An excellent offering for investors seeking a stable rental property in the Eastern Shores highly regarded Talbot County market. Property is being sold As-Is. Showings by appointment only. BUYER RESPONSIBILITY TO PERFORM DUE DILIGENCE REGARDING PROPERTY LOCATION, USE, RESTRICTIONS, AND TAXES.

Located in the heart of St. Michaels' historic district, this adorable cottage has rare central commercial 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!

Rare opportunity to own a commercial property in the heart of historic downtown St Michaels. Situated on a prime, high-visibility corner lot, this turn-of-the-century building offers approximately 2,100+/- square feet of space with strong foot traffic and excellent exposure. Off-street parking and climate controlled outbuilding for additional storage adds convenience. Enjoy flexibility for a variety of uses.

Prime and rare opportunity to locate your business on the main entrance to St. Michaels. High visibility, excellent access and plenty of parking. Zoned "General Commercial" with 3 separate buildings totaling over 9,678+/- sf. Possible expansion, no town taxes.

Well established restaurant in the Busy Easton Marketplace Shopping Center. Strong track record with a well known location and product. All furniture fixtures and equipment convey.

One of a kind beautifully maintained building in St. Michaels, Renovated and enlarged in 2002 . First floor offers 4 office suites, workroom, conference room, 2 bathrooms and kitchen/break room. ADA compliant Second floor has 2 separate outside entrances , multiple offices, conference area, and 2 bathrooms. There is paved parking for 30+cars. Designed by Christine Dayton and built by Peter Hanlon, CG zoning offers many possibilities like Healthcare, medical, dental, private offices , convenience store, food services, Day Care, Church, Government offices, etc. Buyers to confirm with Talbot County Planning & Zoning regarding the permitted uses.

The Historic Robert Morris Inn - Americas Oldest Full-Service Inn Waterfront Hospitality Legacy Oxford, Maryland Est. 1710 Step into history with the Robert Morris Inn, Americas oldest full-service inn, perfectly situated on the Tred Avon River in the heart of Oxford-a picturesque seaport town founded in 1666. Built as River View House in 1710 and operating as an inn since 1800, this landmark property is named for Robert Morris Jr., a Founding Father and financier of the American Revolution. Directly across from the historic Oxford-Bellevue Ferry, the inn combines colonial charm with modern amenities and ongoing upgrades-creating a truly unique and successful waterfront destination. Property Highlights: 14 guest rooms, all with private en suite baths, including several suites. Newly renovated private suite with luxury finishes and expansive river views. The Financier Restaurant - a beloved, full-service dining venue with historic character. New bar, banquet room, and private dining room - ideal for events and group bookings. Elegant public spaces with fireplaces, original woodwork, and broad water views. Located on prime Waterview lot with potential for future expansion or retail use. Situated in affluent Talbot County, a premier Eastern Shore destination. Recent Improvements: Extensive upgrades to the commercial kitchen. New bar, banquet, and private dining rooms to expand hospitality offerings. New boiler for heat and hot water. All guest rooms have been refreshed. Fresh paint and updated furnishings in several public spaces. Ongoing cosmetic and infrastructure improvements. This is a rare chance to own a thriving, historically significant inn and restaurant with unmatched character and commercial opportunity. The Robert Morris Inn is not just a property-its a living piece of American history and a turnkey business ready for its next visionary steward.

Great Investment for first time investor. Reduced $20,000.Great Investmemt. USPS renting Building. They pay taxes and utilities. Long term Lease United States Post Office in Churchton, MD 20733 Private Owner/Licensed Broker In the State of Maryland. Great rental and investment. Subject to 1031 exchange. 1 Acre of commercial land and building.

Well established restaurant in the Busy Easton Marketplace Shopping Center. Strong track record with a well known location and product.

The Hollyday House - A Rare Historic Opportunity in Downtown Easton Just one block from the heart of Downtown Easton, this historic gem offers exceptional potential for commercial or residential use. Situated on a spacious 1/4-acre lot, the property provides room for expansion of the existing structure or the addition of accessory buildings (subject to zoning and approvals). Currently configured as a commercial building, The Hollyday House is ideal for a business seeking a charming and highly visible location, or for a buyer looking to transform a piece of history into a unique private residence close to Eastons vibrant shops, restaurants, and cultural venues. Whether you're an investor, entrepreneur, or preservation-minded homeowner, this is a rare chance to own a storied property in one of Easton's most desirable neighborhoods.

Substantial building right in the middle of all the action of Downtown Easton and the bustling Amish Market is just across the street. This former Veterinary Clinic has a large reception area and check in area, a variety of offices, rooms and garages and several high quality kennels remain on site too. This is quite a value for what is being offered. Owner may make some improvements if requested.

499 Idlewild Ave., Easton, MD Is a unique opportunity to own recently built, triple-net, commercial real estate in the Easton medical and professional corridor. This acquisition provides investors with an income-producing property consisting of a 20,000 square foot building constructed in 2019, offering 100% occupancy. Present tenants all exceed five-year terms with strong financial and tenancy records. This property has the potential to provide a significant Return on Investment within the first few years of ownership, following a projected Pro Forma which reflects market rate and standard escalation and terms in the Easton professional space market. Acquiring this property provides investors with 20,000 square feet of Class A medical and professional office, constructed to exceed building efficiency code requirements and provide ample parking. This building's proximity to Route 50, the University of Maryland Shore Medical Center (0.50 miles), and downtown Easton offers easily-accessed amenities and quality restaurant options, making this an attractive option for any tenant seeking space within this market

Unique parcel of ground in Easton. Sale does NOT include cell tower which will be sold separately. It is in the PRD District but is zoned BC by the Town of Easton with residential as a permitted use. Survey available. The property is not in the Town Historic District. Feel free to ride on the property but no access until January.

Dont miss out on this rare opportunity to transform this 56+/ -acre parcel into a premier development project. This expansive property offers a blend of zoning options and fantastic exposure on Route 50, making it an ideal investment for developers. The property is well-suited for high-visibility projects including home improvement stores, pad sites, restaurants, and so much more. All utilities are at the site. Located in the prime area of Easton with easy access to major roads and amenities. Owner will consider all reasonable offers. Owner will develop for a credit tenant. This offering includes Tax Map 100, Parcel 0420 Chapel Road, Easton. Located in Eastons Opportunity Zone! Contact us today to start turning your vision into reality! Available for Sale or Lease - call for additional information.

Final section of Lakelands subdivision! Previously approved for up to 48 lots, road cut thru, some water & sewer installed. PUD approved by Town in 2010. See agent for plats, engineering and current status. Unique opportunity! Wetlands needs to be updated with possible additional land becoming available. Road needs completion. Some Capital fees already paid. Water lines partially installed along with sewer lines. Water lines needs upgrading for sprinklers.

Two story Tavern/Restaurant with approximately 600 sq. ft. deck on back on 23,723 SF of land with approximately 25 parking spaces. Tenant has full liquor license with on/off premises sales, keno, drive up window. Major renovation in 1998 included updating windows, insulation, wiring, roof and septic. Renovation was started but not completed therefor this property is being sold as-is at an objectively reduced price.

Multi tenant building - prime location, zoned general commercial, completely fenced yard, all public utilities.

Competitively priced professional space located in Easton, MD just off Route 50. The interior offers itself as existing medical use but could easily be converted to general office or retail. This unit currently features four existing exam rooms with reception, office, and common area. This condo property is well maintained and offers private entry and substantial at large parking in a private lot. This unit is also available for lease at $14 per square foot, NNN. Contact the listing advisor for additional details.

Great Investment Opportunity - This 5500+/- sq ft Commercial Condo has a long term Lease with a well-established Tenant. Zoned Commercial, ideal for Medical or related Business. Excellent condition, great visibility and plenty of parking. NNN Lease with Automatic Renewals. 6.75% CAP at $1,595,000.

Located in the heart of Eastons medical and healthcare district-and just moments from Route 50-this 1,500± sq. ft. end-unit commercial condo offers an exceptional opportunity for medical, dental, or professional office use. If youre ready to own instead of rent, this space delivers the flexibility, infrastructure, and location your business needs. Thoughtfully designed with a highly functional layout, the unit features a welcoming waiting room, dedicated reception area, two restrooms, five office/exam rooms, break room, equipment room, sterilization area, and mechanical room. Every treatment room includes a sink and is fully plumbed for dental chairs with water, suction, and air at both ends. Wiring is already in place for digital dentistry, panoramic X-ray, and data systems. All rooms also include Radon fans installed during COVID to create negative pressure-an added layer of safety and value. Additional perks include 220V service for autoclaves and laundry hookups. Interior walls can be easily reconfigured to suit your practice or workflow. Recent updates include a new roof and freshly repaved parking lot. Shared operating costs-trash, lawn care, landscaping, and water-are divided among the four units based on square footage.With ample parking and a prime location surrounded by established healthcare providers, this space is a rare chance to elevate your business while building equity. Perfect for medical, dental, therapy, or professional users looking to stop paying rent and secure a smart long-term investment. Bring your buyers. Bring your business. This opportunity wont last.

Two RT 50 parcels located in Easton on sought after O.C. bound side at corner of Rt 50 and Dutchman s Lane. Office on property in good condition but sold as-is. Zoned General Commercial with all utilities available at site.

Rare investment opportunity! This 12,000 sq. ft. warehouse, located on a prime piece of real estate along westbound Route 50 in Easton, MD, offers unmatched visibility and accessibility. Featuring two separate structures on the property, this versatile space is ideal for a variety of uses including warehousing, storage, light manufacturing, or more. With its strategic location in a high-traffic area, this property is perfect for businesses looking to capitalize on exposure and convenience. Whether you're expanding your operations or looking for a smart investment, this is an opportunity you don't want to miss

Recently renovated high visibility and high traffic count highway corner location. Sky is the limit on this newly renovated restaurant Corner Lot on US 50 (Ocean Gateway). 35,000 cars go by the front and 11,000 cars go by the side of this property everyday. 3,850 square foot building with a large kitchen with multiple Hoods, Walk Ins - Refrigerator and Freezer, and Sinks. More than ample electrical supply, two large commercial bathrooms, and an accessory storage building make this property "Turn Key" for the next operator. Fresh opportunity for a Mexican / Italian operator to step right in and take over a corner location in Easton MD.