Waterside Group LLC develops and manages a broad range of private real estate, lifestyle, and entertainment companies.

With a team of seasoned professionals and partners, we leverage industry knowledge with insight and innovation to create vibrant communities and elevated experiences.

Committed to the highest quality in everything we do, Waterside Group specializes in sustainable, long-term results that maintain a high value. Our development and management staff provide an extraordinary mix of expertise, creativity, enthusiasm, and talent to ensure the success of our holdings.

Featured Brands & Holdings

Longfellow Design Build

Falmouth, MA – An award-winning design-build firm providing integrated architectural design & building construction for new homes, renovations, and additions for homeowners on Cape Cod, Greater Boston, and Lincoln, NH. Office and showroom locations include Falmouth, Osterville, Sandwich, Boston/ South End in MA, and South Peak Resort on Loon Mountain in NH.

Falmouth Tides Hotel

Falmouth, MA – The newly renovated Falmouth Tides Hotel is at the entrance to Falmouth Harbor and has breathtaking 360-degree views, including both Vineyard Sound and Martha’s Vineyard. The property includes twenty-nine rooms with an award-winning design, a private beach, and a roof deck.

South Peak Resort

Lincoln, NH – South Peak Resort is the private ski-on, ski-off homeowner community at the base of Loon Mountain in Lincoln, New Hampshire. South Peak offers both mountain and river view home lots and condominium opportunities available for sale with private chair lifts and trails maintained and groomed by Loon Mountain Resort. Both South Peak and Loon Mountain have robust master plans for continued development that includes additional trails, amenities and a village with restaurants and retail shopping to the area.

Alpine Adventures

Lincoln, NH – Alpine Adventures offers guided outdoor tours on 300 acres of privately owned land in the heart of New Hampshire’s White Mountains in Lincoln, New Hampshire. Open year-round, Alpine Adventures tours include an off-road tour in Austrian all-terrain vehicles, zip-line tours that reach speeds of 60 mph and climb 250′ above the forest floor, and a self-guided aerial challenge course that includes bridges, cargo nets, rope ladders, and a heated treehouse. In the winter season, Alpine Adventures also offers snowshoe tours.

Whales Tale Waterpark

Lincoln, NH – Whale’s Tale is a 17-acre water park located in Lincoln, NH with an industry-leading blend of water slides and attractions including Akua Beach, a simulated surfing wave pool, cabanas, and live music – All nestled within New Hampshire’s White Mountains. Whales Tale is New England’s most visited waterpark and has been in business for more than 30 years.

Flying Bridge Restaurant

Falmouth, MA – Voted ‘Best Waterfront Restaurant 2024’ by Cape Cod Life Magazine readers. The Flying Bridge is Cape Cod’s destination for outdoor dining, weddings, events and live music on Falmouth Harbor. A local favorite for traditional New England seafood with a contemporary flair, sushi and delicious craft cocktails./p>

Longfellow Design Build

Falmouth, MA – Located on Falmouth’s deep water harbor, the Flying Bridge Marina has quick access to some of the world’s best fishing and cruising. Halfway between Newport, RI, and Nantucket Island, Falmouth provides quick access to Woods Hole, Buzzards Bay, and the islands of Martha’s Vineyard and Nantucket. The Flying Bridge is a full-service marina adjacent to the award-winning Flying Bridge Restaurant. Marina services include engine sales, re-powers, maintenance, repairs, and dry storage. The Flying Bridge is also the regional dealer for HCB Yachts, Chris-Craft, and Inmar Inflatable Boats.

Timber Axe Bar & Bowl

Falmouth, MA—Axe-throwing, Candlepin Bowling, a Delicious Menu of Bar Bites, Creative Cocktails, and live Entertainment.

Lighthouse Station at Woods Hole

Woods Hole, MA – Thirty-nine unique water-view residences located on a natural bluff overlooking Vineyard Sound with views of Martha’s Vineyard and the Elizabeth Islands, Lighthouse Station is an extraordinary opportunity to own a luxury, ocean-view residence in the vibrant, year-round village of Woods Hole.

Ricks Outboard Marine

Fairhaven, MA – For over 30 years, Rick’s Outboard Marine has provided expert marine maintenance and repair services, including engine sales & repowers, diagnostics, electronics, and boat storage.

Three Suns Captiva

Newly renovated from top to bottom, Three Suns Captiva is the ultimate luxury vacation home rental on Florida’s Captiva Island. This six-bedroom home has an unbeatable oceanfront location, modern coastal decor, and a wide variety of amenities and activities catering to every family member.


Services provided by our development team include:

  • Real Estate Development

  • Architectural Design

  • Building Construction

  • Engineering

  • Property Management

  • Business Strategy

  • Team Development

  • Core Business Operations

  • Accounting & Internal Controls

  • Marketing & Branding

  • Marketing Content Development


To contact The Waterside Group, please call (774) 255-1709 or use the form below.