Construction Estimator

About the Role

Waterstone Properties Group is seeking a Project Estimator to lead estimating efforts across a diverse and growing portfolio of retail-driven development projects.

This is a newly created, high-impact role where you will serve as the company’s primary estimator—owning the full lifecycle of project estimates from concept through construction execution. You will play a critical role in shaping how estimating is done within the organization, with significant influence over tools, processes, and best practices.

Key Responsibilities

• Lead end-to-end estimating across multiple projects, including: Conceptual / ROM estimates, Schematic estimates and Hard bids
• Analyze construction drawings, renderings, and project plans to develop accurate cost projections
• Evaluate labor, materials, timelines, and overall project feasibility across all phases of construction
• Collaborate closely with external general contractors and subcontractors to validate pricing and scope
• Perform quantity takeoffs and ensure estimate accuracy as an individual contributor
• Apply value engineering principles to optimize cost, materials, and construction approach
• Present estimates and recommendations to internal leadership, including principals and senior stakeholders
• Support broader project planning when needed (scheduling, coordination, and process improvement)
• Help design and implement estimating tools, systems, and workflows for the organization

Project Scope

• Primary focus on retail development projects, including major national tenants and mixed-use environments
• Additional exposure to:
• Multifamily housing
• Commercial projects (e.g., hotels, parking structures)
• Infrastructure elements (roads, site work)
• Manage estimating needs across multiple concurrent projects (typically ~5+), varying in size and complexity

What We’re Looking For

Must-Haves

• Proven experience in construction estimating across multiple trades/materials (not single-scope estimating)
• Ability to build full-cycle estimates from scratch, from concept through bid
• Strong understanding of construction methods, cost drivers, and project lifecycles
• Hands-on experience working with general contractors and interpreting subcontractor bids
• Ability to work as an independent contributor and own the estimating function end-to-end
• Strong Excel and analytical skills; comfort working from drawings, renderings, or incomplete project data

Preferred

• Background in retail or mixed-use development
• Experience in high-growth or entrepreneurial construction/development environments
• Familiarity with estimating software (or ability to help implement tools)
• Exposure to value engineering and cost optimization strategies
• Construction or trade background is a strong plus

Work Environment

• Hybrid role with flexibility, but must be able to:
• Attend in-person meetings
• Visit job sites when needed to inform estimates
• Open to candidates based in:
• Massachusetts
• New Hampshire
• Maine