Winter Park real estate, handled by the broker who has been here since 1986.

Michael O’Shaughnessy Inc. Real Estate Brokers serves the residential and commercial real estate needs of Central Florida: sales, property management, leasing, brokerage and investments, all from one downtown Winter Park office.

Call (407) 628-4430 Ask about a property

1986Established in Winter Park

Residential + CommercialSales, leasing & management

Central FloridaLocal knowledge, local contacts

Michael ☘
O’Shaughnessy

Real Estate Brokers

Management
Brokerage
Investments

Since 1986

The Canton Avenue sign, carried into the website.

What we do

Three ways we work for you

The same three words on the sign out front. Each one is a full service, run by a broker who knows this market street by street.

Management

Property management and leasing for owners who want their Central Florida property looked after by a local broker, not a call center.

Residential & commercial management
Leasing and tenant placement
One local point of contact

Brokerage

Residential and commercial sales backed by decades of local market knowledge and a proactive, aggressive approach to getting deals done.

Residential sales
Commercial sales
Marketing a property, start to close

A commercial building, the kind of asset investors buy in Central Florida

Investments

Help fine-tuning an investment strategy, analyzing scenarios, and locating opportunities across the Central Florida market.

Investment strategy
Scenario analysis
Locating opportunities

A Central Florida home on a quiet residential street

The approach

Local knowledge is the whole advantage

An established, reliable and aggressive real estate company, built on specialization in different parts of the industry and a true insider’s view of what is happening in this market.

Insider market knowledge

Decades in Central Florida mean pricing, timing and opportunities get read early, not late.

Specialists, not generalists

Different aspects of the industry, sales, management, leasing, investments, handled by people who focus on them.

Proactive, not passive

Professionalism and an aggressive, proactive approach in an age of instant results.

About Michael

The broker behind the sign

Michael O’Shaughnessy has run his brokerage from downtown Winter Park since 1986, setting higher standards for Central Florida sellers and investors: ease of mind, service, convenience, transaction expertise and market knowledge on every deal.

Off the clock, a world-record waterman

Michael is a UCF Athletics Hall of Fame member and holds four world records for the fastest crossings of the English Channel, the Irish Sea, Loch Ness, and Cuba to the USA on a traditional paddleboard. The same endurance that crosses oceans closes deals.

Where we work

Downtown Winter Park, serving Central Florida

Home base is Suite 44 at 201 W Canton Ave, a short walk from Park Avenue. The work covers homes, commercial property and investment deals across the region.

Winter ParkOrlandoMaitlandCentral FloridaResidentialCommercial

A modern Central Florida home — Homes bought and sold across Winter Park and Orlando

A home with a pool in the evening — Residential sales, leasing and management

A commercial office building — Commercial brokerage and investment property

Contact

Talk to Michael’s office

Buying, selling, leasing, or looking at an investment? One call reaches the broker directly.

Office

201 W Canton Ave, Suite 44
Winter Park, FL 32789

Phone(407) 628-4430

Email44@MichaelOShaughnessy.com

Services

Management · Brokerage · Investments
Residential & commercial sales and leasing