Annapolis, Maryland Businesses for Sale

Discover the charm of owning a beautiful 70-foot schooner and its thriving charter business, available for the first time in over 30 years. This turnkey operation boasts prime city center dock space in historic ports, offering unforgettable day sailing cruises in the NE and Mid-Atlantic regions. With a solid book of business and 27 years of successful sailing, this custom-designed vessel promises an independent lifestyle and excellent income potential for an owner-operator.In 2023, there were approximately 154 trips with a total of 5,223 passengers or roughly 34 people per trip. The crew consists of the boat captain plus one, but typically is the captain plus two crew members. The maximum crew is 3-4 at any one time and there is someone who helps with parking when the boat is in New England. The crew is all seasonal and there is also one person who assists with reservations in the summer and marketing in the off-season.

Cash Flow $100,000

Revenue $347,000

Business Opportunity

Min. Cash Req: $75,000

Broadway Joe's SportsPicks & Predictions

Offer of the Year! The North American fantasy sports market is expected to reach $24.2 billion by 2029. This is a low-cost opportunity with over 62 million fantasy sports players in the USA and Canada alone! Learn more now.

Asking Price: $195,000

Painting Business for Sale - Annapolis, MD

Annapolis, MD

Anne arundel County

Established and successful Residential and Commercial Painting business franchise for sale in the Annapolis, Maryland territory. Business was started in 2023 and had Annualized Gross Revenues of approximately $400k in 2025. This is a well known nationwide painting company with excellent reviews and ratings. Turn-key business includes: two trained employees ( sub-contracted painters), all painting supplies, office equipment, furniture, signage and vehicles included. (Note - business owners do not do the painting - your painting crew handles all of the painting services.) Owner motivated to sell!

Cash Flow $50,000

Revenue $400,000

Franchise Opportunity

Min. Cash Req: $100,000

Batteries Plus

Over 30 years of consistent growth. Ongoing support. Multiple revenue streams. Whether you’re looking into owning your very first store, or you’re interested in adding to your existing franchise portfolio, Batteries Plus is here to help. Learn more about the costs, benefits, and available locations today!

Asking Price: $2,900,000

Daycare, CHildcare

Not Disclosed, MD

Not disclosed

This is one of the highest income-producing daycare centers in the nation. The center is exceptionally well-managed with a loyal team in place, including the Center Director, Assistant Director, Teachers, Floaters, and Administrative staff. It benefits from a significantly low Rent-to-Revenue ratio and very attractive lease terms. The center serves children from infancy through school age and is located in a thriving community surrounded by single-family homes, townhouses, apartment complexes, shopping centers and commercial buildings. Furniture, kitchen equipment, and playground facilities are in like-new condition. In addition, management has implemented state-of-the-art technology for security, CRM, and networking, ensuring both operational efficiency and peace of mind.

Cash Flow $775,000

Revenue $2,804,000

Business Opportunity

Min. Cash Req: $60,000

Wealth Automators

Click the video below to learn how Wealth Automators’ eCommerce stores provide bi-weekly income for the store owner by selling only USA products on Amazon, Walmart, TikTok Shop, and Facebook Marketplace. We use the same business model as the largest stores on Amazon earning $110 Million monthly revenue. Individuals own their stores 100%, while Wealth Automators handles all day-to-day operations in return for a profit split. Business owners achieve 12–29% ROI monthly within 60 days.

Asking Price: $650,000

Thriving auto body repair business

Not Disclosed, MD

Anne arundel County

Thriving auto body repair business, Drive your own success!For 33 years, this family-owned auto body shop in Anne Arundel County has been a trusted name in vehicle repair, serving Baltimore and surrounding areas since 1991. Specializing in vehicle painting, mechanical repair, and frame straightening, this shop has built a stellar reputation for quality workmanship, attracting a loyal customer base. Consistently generating over $1,200,000 in annual sales, the business is a proven success. The highly skilled trained staff, as well as EPA and PPG certified painters, ensures top-tier service. This is a rare opportunity to acquire a thriving business with a strong foundation for continued growth.

Cash Flow $263,391

Revenue $1,427,167

Franchise Opportunity

Min. Cash Req: $150,000

Spherion Staffing & Recruiting

Generate $5.6 million in annual revenue with America’s most-awarded staffing and recruiting franchise. Our network of independent, locally owned franchise offices delivers staffing solutions that matter: temporary, temp-to-hire, direct hire, and on-premise workforce services that connect more than 3,000 businesses with exceptional talent every day. Advance your goals empowered by our vibrant, supportive corporate team and franchise community.

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Annapolis, Maryland Businesses For Sale

8 Annapolis Business For Sale Listings Found