From development to delivery – we create opportunity and growth through real estate projects that leave a lasting mark.
Through projects led by our developer partners
From historic renovations to new multi-unit developments
With a track record of building where it matters most
Our approach is straightforward: identify opportunities, partner with experienced developers, and deliver projects that create lasting value.
We focus on building long‑term value for communities, partners, and lenders alike.
Over 60 successfully completed projects with consistent returns and value creation for all stakeholders.
Strategic approach to project selection and execution, ensuring sustainable growth and minimal exposure.
Focus on building long-term value through quality developments that serve communities and investors alike.
Located near Boston’s prestigious Harvard University, this striking new 43-unit residential building blends modern design with the energy of the neighborhood.
Thoughtfully crafted for contemporary living, this exciting project will deliver spacious, light-filled homes just steps from Harvard’s campuses, parks, and vibrant Boston amenities.
This 38,000 square foot building is targeted for completion in late 2028 -early 2029.
Located in Boston’s Newmarket Square industrial district, this 56,000 square foot brick and beam mill building sat vacant for nearly five years before being purchased by in the Winter of 2013. In addition to the mill building, the sale also included an adjacent ½ acre parking lot.
The project was completed in the Fall of 2016.
56,000 sq ft
23 Office Suites
Vanko Studio
Beginning in the Fall of 2016, D² Development began permitting a three unit, five story, 5,500 square foot condominium building with four garage spaces. All units feature direct elevator access, have at least two bedrooms with two bathrooms, high end finishes and outdoor space. Construction began in the Winter of 2020 with an anticipated delivery date of Spring, 2022.
5,500 SQ. FT.
2020–2022
Salem 5 Bank
Located in Boston’s historic North End, 55 Hull street was dilapidated row home that sat vacant for decades. This two family was ready for conversion the day it was purchased. D² Development began construction in the Spring of 2017 on two luxurious, two bedroom duplex units that feature outdoor space, European designed kitchens, and high end finishes. This project delivered in the Summer of 2018.
2 Duplex Units
Spring 2017 – Summer 2018
North End, Boston
A thoughtful renovation of a historic downtown property, transforming it into modern mixed-use space while preserving its architectural character. This project combines 24 residential units with ground-floor retail, creating a vibrant community hub.
24 months | Est. completion Q2 2026
$8.2M total development cost
Joint venture with Thompson Development Group
Real estate development offers unique advantages that few other opportunities can match
Real estate provides physical, income-generating assets that appreciate over time and offer protection against inflation.
Property investments add stability to portfolios with lower correlation to stock market volatility and consistent returns.
Every project contributes to neighborhood vitality, creating spaces where people live, work, and build their futures.
Experienced professionals committed to building value and lasting relationships.
At age 20, Timothy Penso launched his insurance career and became the youngest recipient ever of the industry’s prestigious Blue Jacket—awarded annually to just one agent for explosive growth among 5,000 peers. As an Elite Producer, he scaled his agencies to high six-figure revenue in record time through innovative systems and high-performance team leadership.
While guiding clients toward financial protection, Timothy saw a recurring gap: interest in real estate exposure without the headaches of ownership. By 24, he bought his first investment property in Salem, MA. Shortly after he had personally executed or partnered in over eight figures in real estate transactions, including syndications where he serves as General Partner. His portfolio now spans student rentals in Upstate NY, ground-up developments in Binghamton and Greater Boston, and limited-partner stakes in Tennessee.
This dual mastery—insurance discipline + real estate execution created InsureRealty.
Raised in humble circumstances, Timothy’s passion with how money works fuels his mission: teach everyday Americans to maximize returns with their own money, using the same collateral-backed, GP-led strategies that built his own wealth. Hundreds of clients later, he remains the trusted bridge between financial security and real estate opportunity.
Years Experience
Client Satisfaction
Value Created
Whether you’re exploring partnerships or simply want to understand our process better – we’re happy to walk you through what we do, how we do it, and what’s coming next.
Whether you’re a lender, developer, or community partner we’d love to explore how we can create value together.
256 Hanover Street, Suite 2R, Boston, MA 02113
