Browse Middle Market Businesses for Sale in Ontario

Looking for Ontario middle-market businesses for sale? DealStream’s curated marketplace features vetted mid-sized companies—manufacturing, distribution, professional services and more—across Toronto, Ottawa, Hamilton and beyond. Compare valuations, review confidential information and connect directly with sellers to streamline your M&A journey. Explore Ontario’s top middle-market opportunities on DealStream today and take the first step toward your next strategic acquisition!

All Matching Deals

Toronto, ON

Our client engages in sales of new and used die casting and foundry related machinery. They manufacture and sell their own new machines and buy and sell used machines. Our client offers two interrelated companies as part of this sale. Together, these companies offer new industrial machinery and...

$5,000,000
Cash Flow: $527,088
Details
Windows and Railings Manufacturer in GTA: Retire
Ontario

Booming Manufacturing business in the Heart of Toronto Industry Focus: Specializes in the design, manufacturing, and installation of aluminum railings and windows for high-rise buildings. Established: Business was founded in 2003, with a window division launched in 2021 to complement the railing...

$7,229,830
($10,000,000 CAD)
Cash Flow: $1,952,054 ($2,700,000 CAD)
Details
Canada-based iGaming Studio
Toronto, ON

A well-established, Canada-based iGaming studio offering dual-certified portfolios: - Class II: 70+ NIGC-certified bingo-style titles (largest global catalog) - Class III: 80+ GLI-19-certified RNG slot and table games Built on a Java/Apache backend with an HTML5 frontend, API-first (JSON/REST)...

$6,000,000
Details
Ontario

Being offered for sale is a digital marketing platform with a primary focus providing brand-focused go-to-market (GTM) campaign strategies A dynamic and innovative online platform that has established itself as a leading player in the digital space. With a robust and user-friendly interface, This...

$5,000,000
Cash Flow: $1,272,212
Details
Rapidly Growing Drilling Business in Ontario
Ontario

Rapid Growth & Strong Reputation The business is a specialized provider of Horizontal Directional Drilling (HDD) services for essential utility infrastructure and has built a strong reputation as a reliable, rapidly growing company trusted by contractors, utilities, and local governments. This reputation...

$8,675,796
($12,000,000 CAD)
Cash Flow: $1,373,667 ($1,900,000 CAD)
Details
Est. Frozen Food Mfg- 30+ Yrs. Nat’l Distribution
Ontario

This is a rare opportunity to acquire a well-established and highly reputable frozen food manufacturing business with over 30 years of proven success. Specializing in a beloved staple with wide consumer appeal, this company has built a strong reputation for delivering consistent, high-quality products...

$5,422,372
($7,500,000 CAD)
Cash Flow: $318,032 ($439,890 CAD)
Details
Personal Care & Wellness Business with Real Estate
Ottawa, ON

An exceptional opportunity to acquire a well-established and highly reputable group of businesses operating in the personal care and wellness industry. This offering includes three synergistic locations operating under one respected brand, combining full-service hair and spa salons with a rapidly growing...

$5,060,881
($7,000,000 CAD)
Details
20-Year-Old Digital & Physical Server Hosting Co.
Ontario

20-Year-Old Digital & Physical Server Hosting Company This 20-Year-Old Digital & Physical Server Hosting Company infrastructure provider has been a key player in high-performance hosting solutions for over two decades. Specializing in empowering businesses with robust and reliable IT infrastructure,...

$14,000,000
Details
Landmark Wheel and Tire Business with Property
Ontario

Acquire a reputable automotive retailer specializing in rims and tires. Since 2007, this business has provided exceptional products and services to a large customer base. With a dedication to customer satisfaction, the business maintains loyal relationships with its clients, ensuring profitability and...

$6,579,145
($9,100,000 CAD)
Cash Flow: $305,821 ($423,000 CAD)
Details
Winery, Vineyard & Event Centre
Leamington, ON

This is an Asset Sale. Vineyard, winery, retail store and 8,000 sq.ft. events venue on 20+ acres in Southwestern Ontario is for sale as a turnkey business. Included is an established vineyard, developed buildings and event centre, parking and natural outdoor seating and park landscape, equipment and...

$6,145,355
($8,500,000 CAD)
Details
Toronto, ON

Business Overview This is a rare opportunity to acquire a profitable and rapidly scalable franchising business in the fast-casual dining sector, offering a mix of traditional storefronts and innovative ghost kitchens across Ontario. The company is a well-loved brand for its healthy, customizable,...

$5,060,881
($7,000,000 CAD)
Cash Flow: $744,672 ($1,030,000 CAD)
Details
Profitable Established Roofing Contractor
Ontario

Highly Profitable Roofing Business in Eastern Ontario for Sale. Successful Roofing Contractor for Sale in Ontario. This business offers a variety of roofing services for residential, commercial, and industrial clients, including new installation, repairs, replacements, and maintenance. With a team of...

$5,000,000
Cash Flow: $1,580,000
Details
Profitable Personal Care & Wellness Business with Property
Ontario

An exceptional opportunity to acquire a thriving and well-established group of businesses in the personal care and wellness industry. This offering features three complementary locations operating under one respected brand, seamlessly integrating full-service hair and spa salons with a fast-growing...

$7,000,000
Cash Flow: $854,000
Details
Air Service /  Aircraft Charter & Outfitter
Hearst, ON

Aircraft Charter services year round on floats and wheel skis. Operating 2 aircraft, DeHavilland Beaver and Turbo Beaver. Property with 2 large hangars, staff residence, 3600' runway, large dock, full service AMO onsite. Tourist outfitter of 50 years with 5 fly-in outpost camps, custom river trips,...

$5,241,626
($7,250,000 CAD)
Details
Injection Mold Parts Manufacturer
Ontario

Highly experienced parts manufacturer specializing in plastic mold parts, and polyurethane foam mold parts with strong production staff and management in place. The business well positioned for many more years of success. Whether you need a mold designed, prototypes made, trial runs (hundreds),...

$5,783,864
($8,000,000 CAD)
Cash Flow: $1,156,772 ($1,600,000 CAD)
Details
Motel for Sale in Niagara Falls, Ontario
Toronto, ON

Location: Niagara Falls, Ontario Asking Price: $8,050,000 Don't miss this incredible opportunity to own a motel in the heart of Niagara Falls! Located just minutes from one of the world's most famous natural attractions , this property is a prime choice for tourists visiting year-round. Whether...

$5,820,013
($8,050,000 CAD)
Details
Toronto, ON

Multi service business with large well established customer base. 2023 revenue of $17 million and $4.1 million EBITDA. Services include excavation, site remediation, street sweeping, waste disposal, sand and gravel slinger service, site drain and waterline maintenance, construction support services

$11,567,728
($16,000,000 CAD)
Details
Big Data SaaS - FoodTech/Restaurant Profitable/M&A
Toronto, ON

Strategic Acquisition Only 85% Profit Margins (can improve/scale) Growth Stage - Ready to scale Major Partnerships Name Brand (recognizable) Turn-Key - Highly Automated Profitable $200k/EBITDA Ready for Growth Competitors SOLD $35MM - $800MM Domain Name alone is valued over $2MM Pricing...

$10,000,000
Cash Flow: $200,000
Details

Tips for Buying A Middle-Market Business

Understand the True Value of the Business

When buying a middle-market business, it’s essential to understand the company’s real value—not just what’s listed in the financial statements. Go beyond surface-level numbers and conduct thorough due diligence, which includes reviewing audited financials, assessing recurring revenue streams, and analyzing customer concentration. Make sure you use multiple valuation methods, such as EBITDA multiples, discounted cash flow (DCF) analysis, and comparisons to industry benchmarks. This multi-faceted approach helps you avoid overpaying and uncovers potential issues that might affect the business’s future performance.

Assess Leadership and Key Staff

Middle-market companies often rely heavily on their management team and key employees. During your evaluation, identify individuals critical to the business’s day-to-day operations and long-term success. Assess whether they intend to stay on after the sale, and look into existing employment agreements. Consider structuring your offer to include retention incentives for these key staff members, as their knowledge and relationships are often integral to maintaining business continuity through ownership transition.

You’ll want to understand not only the business itself but also the broader market in which it operates. Analyze industry trends, such as shifting customer preferences, emerging competitors, and regulatory changes, to assess potential risks and growth opportunities. Talk to industry insiders and professionals, and review market research reports to gain a comprehensive perspective. A strong grasp of the competitive landscape and future industry projections will allow you to make more informed decisions and plan for sustainable post-acquisition growth.