About Cassidy O'Connor

Sales Associate - Osterville Office
812 Main Street, Osterville, MA 02655

Email: Casey.OConnor@Raveis.com | Cell: 774.269.4001


With a strong background in business, interior design consulting, and a deep love for coastal living, Cassidy O?Connor brings a unique, full-service approach to real estate across Boston and Cape Cod. Licensed in 2015, Cassidy quickly rose to success as Rookie of the Year and a multi-million-dollar producer, known for his sharp eye, strategic thinking, and personal touch.

Cassidy?s experience includes over seven years of interior design consulting for a boutique firm on the quay, as well as ownership of The Salty Pearl, a coastal-inspired lifestyle brand. This blend of creative vision and market knowledge gives clients a distinct advantage?whether they?re staging a home to sell or envisioning life in a new space.

Cassidy splits his time between South Boston and the Cape, staying fully immersed in both markets. He specializes in first-time buyers, vacation homes, and investment properties, and is respected industry-wide for his negotiating skills, client advocacy, and ability to win in competitive situations.

With a background in hospitality, a degree in communication, and a gift for making clients feel at ease, Cassidy approaches every transaction with care and dedication. His innovative marketing, tech-driven strategy, and trusted reputation make him a standout choice for buyers and sellers alike.

When not working, Cassidy enjoys summer days on Wings Neck in Pocasset and fall weekends on Nantucket with his German Shorthaired Pointer, Cisco. Whether you?re dreaming of a Cape escape or your first Boston condo, Cassidy O?Connor is the agent who will get you there?seamlessly and successfully.


Price Reduced

$4,999,900

5 beds

9 baths

7,354 sqft

444 Vineyard Road, Barnstable, (Cotuit), MA, 02635

$3,100,000

3 beds

4 baths

5,008 sqft

34 Farm Valley Road, Barnstable, (Osterville), MA, 02655

Upcoming Open House

Price Reduced

$2,000,000

4 beds

5 baths

4,009 sqft

498 Elliott Road, Barnstable, (Centerville), MA, 02632

$1,950,000

5 beds

6 baths

4,729 sqft

443 Elliott Road, Barnstable, (Centerville), MA, 02632

$1,254,999

4 beds

4 baths

3,101 sqft

26 Carlson Lane, Barnstable, (West Barnstable), MA, 02668

$1,200,000

3 beds

3 baths

2,246 sqft

40 Cocheset Path, Yarmouth, (West Yarmouth), MA, 02673

New Listing

$1,199,000

4 beds

3 baths

2,396 sqft

20 Howland Lane, Sandwich, (East Sandwich), MA, 02537

Upcoming Open House

$1,187,000

7 beds

6 baths

3,415 sqft

138 Chase Street, Barnstable, (Hyannis), MA, 02601

$1,187,000

7 beds

6 baths

3,500 sqft

138 Chase, Barnstable, MA, 02601

Price Reduced

$1,150,000

3 beds

2 baths

1,280 sqft

59 HOPE Lane, Dennis, MA, 02638

Upcoming Open House

Price Reduced

$1,050,000

5 beds

3 baths

2,470 sqft

32 NIAGARA Lane, Yarmouth, (West Yarmouth), MA, 02673

Upcoming Open House

$999,500

3 beds

2 baths

2,426 sqft

219 Pheasant Hill Circle, Barnstable, (Cotuit), MA, 02635

View All Office Listings