A middle-aged man smiling, wearing a blue Polo shirt with "Shepard Construction" logo, standing outdoors with a blurred background of greenery and a building.

Meet Bob Shepard

Builder. Visionary. Trusted Partner.

Owner/Principal, Shepard Construction & Development LLC

With over 45 years in construction, development, and project management, Bob Shepard has built more than structures—he’s built a reputation for excellence, leadership, and trust. As founder and principal of Shepard Construction and Development LLC, he brings deep industry expertise to every residential and commercial project.

Previously, Bob served as Senior Vice President of Modern Continental Enterprises, where he helped grow the firm into one of Massachusetts’ top five homebuilders and led major commercial and marine projects, including Independence Wharf in Boston and the Caribbean Jewel Beach Resort in St. Lucia.

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Over his career, he has overseen the construction of more than 1,700 homes and managed over one million square feet of property, from custom luxury builds and complex renovations to mixed-use developments and marine construction. Known for his collaborative, honest approach, Bob is valued by clients for clear communication and steady leadership through challenges.

An active member of the Builders and Remodelers Association of Greater Boston, he has served on state and local boards, chaired committees, and was honored as Builder of the Year. Licensed in both construction supervision and remodeling, Bob continues to lead with professionalism, humility, and a passion for building meaningful projects and lasting client relationships.

Meet the Team

  • A woman with blonde hair smiling and standing outdoors in front of a background of green and yellow autumn foliage. She is wearing a navy vest with a logo that reads "Shepard Construction & Development" over a black long sleeve shirt.

    Caitlyn Huskins

    CONTROLLER

  • Smiling older man wearing sunglasses, a blue polo shirt with a company logo, and beige pants, standing outdoors with blurred green trees in the background.

    Tim Grandy

    SENIOR PROJECT MANAGER

  • Smile of a man with crossed arms outdoors with green blurred trees in background.

    Rob Maskell

    ROJECT MANAGER

  • A smiling middle-aged man with glasses and short gray hair, wearing a navy blue polo shirt with a logo that reads "Sheppard Construction & Development" and beige pants, standing outdoors with a blurred background of green and yellow autumn leaves.

    Brian Lynch

    PROJECT MANAGER

  • A smiling young man with brown hair, wearing a navy polo shirt with a logo and text, standing outdoors with green trees in the background.

    Patrick Driscoll

    PROJECT MANAGER

  • Man smiling in front of a corporate sign with the company's logo and name.

    Jonathan Shepard

    ASSISTANT PROJECT MANAGER

  • Adult man standing outdoors on a sunny day with trees in the background, smiling and wearing a navy polo shirt and blue jeans.

    Jerry Price

    PROJECT MANAGER

  • A young man with glasses and short brown hair smiling with arms crossed, standing outdoors in front of a green leafy background.

    Brendan Hunt

    ESTIMATOR

  • A woman with dark hair smiling outdoors with green foliage in the background, wearing a navy blue vest over a white long sleeve shirt.

    Karen Ashmont

    ADMINISTRATIVE ASSISTANT