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What experiences and perspectives would you contribute to the Planning Board?
Over the past four years, I have worked on bringing mixed-use developments to Winchester. In 2024, I was part of the board that unanimously approved the affordable housing mixed-use development at Waterfield. Following that, I worked on new zoning to comply with the state's MBTA 3A requirements and new zoning for North Main Street. A focus for me was on crafting design standards to help guide new development. That zoning prioritizes inclusionary housing and mixed-use development to enliven the neighborhood, encourage appropriate density, and increase the town's tax base.
As we move forward, experienced and committed Board members are essential to ensure that new buildings complement Winchester's established character. Thoughtful design review is not automatic — it requires diligence, knowledge, and persistence.
I grew up in Winchester and graduated from Winchester High School in 1984. My interest in the town's historic design began in 1978 during a unit on Winchester's architectural styles at McCall Junior High School, and it has remained a lifelong passion. Professionally, I work as a fractional CFO for life sciences companies, bringing financial discipline and analytical rigor to my work. In my spare time, I design and build furniture from rough-cut lumber — a hands-on craft that deepens my appreciation for materials, proportion, and detail.
I bring to the Planning Board both technical expertise and a deep personal connection to Winchester's history and character.
What are two or three issues facing Winchester, related to town planning, that you think are most important and what are your positions on them?
HOUSING AFFORDABILITY AND DIVERSITY OF HOUSING TYPES
At the top of the list is affordability. Many people simply cannot afford to live here. Winchester lacks smaller, apartment-sized residences that would allow young professionals, downsizing seniors, and middle-income families to remain in town.
At the same time, many residential teardowns are replaced by 5,000- to 6,000-square-foot single-family homes, further narrowing affordability. If we want a vibrant, economically diverse community, we must create housing options beyond large single-family homes.
STRENGTHENING THE COMMERCIAL TAX BASE
We need to encourage thoughtful business growth to generate revenue and support town services. The North Main Street zoning is an important step, but it is only a step. We must continue to negotiate carefully and strategically to ensure that new development benefits the town — economically and aesthetically.
PRESERVING WINCHESTER'S HISTORIC CHARACTER WHILE ALLOWING GROWTH
Growth and preservation are not mutually exclusive. However, achieving both requires experience, judgment, and sustained effort. Maintaining the look and feel of Winchester while accommodating necessary development is not a "slam dunk" — it takes committed oversight.
Please comment on the pros and cons of new development that includes mixed use and affordable/low income housing.
Mixed-use and affordable housing developments offer significant benefits. They promote downtown vibrancy by increasing foot traffic, supporting local businesses, and creating opportunities for residents to downsize and age in place. They can also generate needed tax revenue for the town.
I spent many years living in an apartment in the city and valued the diversity, walkability, and access to amenities. People from all walks of life lived side by side. Restaurants, shops, and services were within walking or biking distance. That kind of vitality strengthens a community.
Importantly, we do not have to sacrifice our historic downtown character to achieve these goals. In fact, traditional New England streetscapes were often more walkable and vibrant than what we have become accustomed to today. With the right expertise and attention to design, we can achieve both economic vitality and architectural harmony.
We are also making steady progress toward our Chapter 40B (SHI) goals, a commitment I strongly support.
What predominant factor would lead you to support or oppose mixed use and affordable/low income housing?
The most important factor is whether a proposal expands meaningful housing options while respecting Winchester's architectural character. I support mixed use and affordable/low income housing because I want Winchester to be a place where people of all ages and income levels can live.
My mother, who is 86, is beginning to wonder how long she can remain in her single-family home. Yet there are limited alternatives in town that would allow her to downsize while staying in the community she loves.
Winchester can readily accommodate high-income professionals — doctors, lawyers, bankers, developers — and they make important contributions. But we struggle to accommodate teachers, artists, academic scholars, police officers, firefighters, and others who enrich our community in different ways.
The Planning Board can influence outcomes by ensuring new buildings are attractive, well-designed, and harmonious with Winchester's historic downtown. Beautiful, thoughtfully designed buildings become desirable places to live, creating a virtuous cycle that encourages further high-quality, inclusive development. I intend to continue working closely with the Design Review Committee and to give meaningful weight to its recommendations.
Why should voters elect you to the Planning Board?
As a current Board Member, I am part of a strong, experienced and committed team. This experience has shaped my thinking and made me open to diverse perspectives. The current Planning Board team members complement one another in important ways. Currently we have a developer, an engineer, and a former conservation commission member among other skills. Losing any of those team members could adversely impact our ability to complete reviews already in progress – particularly in the areas of achieving architectural harmony and preserving historic downtown character – areas in which I excel. I understand what it takes to move complex projects forward and have the discipline to follow through in advancing Winchester's goals.
I will work proactively to guide necessary growth so that it enhances — rather than detracts from — the beauty and historic character of our town. Achieving that balance requires experience, financial judgment, design sensitivity, and strong working relationships — including with the Design Review Committee and Historical Commission — all of which I bring to the role.
My allegiance is to Winchester and its residents, not to any special interests. I view service on the Planning Board as a serious responsibility and a public trust.
How would you like voters to contact you? nrossettos2@outlook.com
