Matthew Giangregorio Real Estate Page - Charlesgate Realty Group

Matthew Giangregorio Real Estate Page - Charlesgate Realty Group Full Service Real Estate Agent with Charlesgate Realty Group Matt takes pride in his profession and in representing his clients’ interests with integrity.

With fifteen years of experience in the real estate industry, Matthew Giangregorio is a trusted go to real estate professional, a top-producing senior agent, and a respected market expert in the Greater Boston Area. A lifelong resident of the Boston area, Matt offers a unique and versatile set of skills that have been honed from years of experience and immersion across a variety of different space

s in the real estate business. Beginning his career in 2010 leasing apartments, Matt quickly became one of the city’s top leasing agents before soon expanding into Residential Sales. This foundation led Matt to recognize and appreciate the powerful opportunities provided through owning real estate early in his career and inspired Matt to buy a 2-family property, which he owner occupied and has since used as a tool to acquire other properties. Matt has now been a residential landlord and investment property owner / operator for over a decade. In addition to an exceptional track record of successful condo and single family sales, Matt has experience and expertise brokering multi-family transactions, has worked in sourcing and evaluating value add, development, and entitlement deals for developers, has experience operating Commercial Property and in Commercial Brokerage, has experience in property management, and has worked as an award winning on-site sales director for multiple pre construction / new development projects ranging from 3 family condo conversions all the way up to 65 unit multi-million dollar new construction, luxury condominium building sell outs. A member of the Massachusetts and Greater Boston Association of Realtors, Matt takes pride in assisting his clients and customers in successfully navigating the real estate market and reaching their real estate goals. Working with home buyers, sellers, developers, investors, and landlords in Boston and The Greater Boston Area, Matt stays on top of real estate transactions from start until after closing to help ensure a smooth process while leveraging an edge in demonstrated market expertise, technology, sales skills, pricing strategy and analysis, marketing, professionalism, and customer service. His well-rounded background informs his client-focused approach, providing him with the insights and expertise to guide clients toward fulfilling their own real estate aspirations. Before working in real estate, Matt spent several years in the financial industry; he has a degree in Business from Salve Regina University, and is a Boston Latin School alumn. Outside of real estate, Matt enjoys staying on top of current events and finance, spending time with friends and family, and living a healthy, active lifestyle. For those seeking assistance from a dedicated professional market expert with proven results, Matt is ready to help you navigate the market and achieve your real estate goals.

Grateful to all of my trusted vendors, professional partners, and especially my clients for their continued trust and co...
05/04/2026

Grateful to all of my trusted vendors, professional partners, and especially my clients for their continued trust and confidence in me.
In this market, results are driven by strategy, precision, and strong ex*****on. When real estate is approached with intention, attention to detail, and a clear plan to deliver the best possible outcome, exceptional client results and a good start to the year personally are simply a by-product.

Just Listed on Beacon Hill17 Bowdoin Street Unit 4AB Boston, MA 02114$999,0002 Bedroom - 2 Bath Condo WITH PARKING890 Sq...
04/29/2026

Just Listed on Beacon Hill

17 Bowdoin Street Unit 4AB Boston, MA 02114

$999,000

2 Bedroom - 2 Bath Condo WITH PARKING

890 Square Feet - Elevator and Private Storage Unit

Fantastic opportunity to own a piece of Beacon Hill! Floor-through 2 Bedroom / 2 Bath condo with DEEDED OFF-STREET PARKING in an ELEVATOR Brownstone Building! Thoughtfully laid-out, this residence blends historic charm with modern, functional living; featuring a spacious living/dining area with custom built-ins, A/C, hardwood floors, and a full second bath. The updated kitchen offers granite counters, stainless steel appliances, and a breakfast bar that opens to the living space. The primary bedroom features an updated on-suite bath, and generous closet space; the second bedroom offers flexibility for guests or a home office. All of this in a professionally managed, pet friendly, brick building with private storage, and common laundry. Enjoy the best of Beacon Hill in this central location, in close proximity to MGH, The State House, Public Transit, and unparalleled access to everything Downtown Boston has to offer. Exceptional city living in one of Boston's most iconic neighborhoods!

Sold! It was a pleasure to have been able to bring this South Boston Multi-Generational 3 Family Asset / Development Opp...
04/21/2026

Sold! It was a pleasure to have been able to bring this South Boston Multi-Generational 3 Family Asset / Development Opportunity to market for the long time owners of this multifamily and to have the property successfully sold at top of market after a rigorous marketing and sales campaign. This was achieved while continuing to operate the fully leased building at full capacity and continue to produce strong income through the sales process for the sellers and for the new ownership as they go through the permitting process post closing!

  pleased to have helped my awesome, repeat buyer clients beat out multiple offers and secure this great home in a still...
04/09/2026

pleased to have helped my awesome, repeat buyer clients beat out multiple offers and secure this great home in a still very competitive suburban market!

Closing out 2025, the highest residential sale in Massachusetts for the year was 3 Sherburne Way - Nantucket, MA, a spec...
12/31/2025

Closing out 2025, the highest residential sale in Massachusetts for the year was 3 Sherburne Way - Nantucket, MA, a spectacular waterfront compound that sold for approximately $37.75 million 💰. This Nantucket estate, set on prized harborfront land, showcases classic island architecture, sweeping water views, and the kind of indoor–outdoor living that has made Nantucket one of New England’s most coveted summer destinations. 🌊✨

In addition to this record-setting home sale, the highest overall real estate transaction in Massachusetts in 2025 was the sale of 1 Lincoln Street in Boston 🏙️—a 36-story Class A office tower in the heart of Boston's Financial District. One Lincoln provides over 1.1 million square feet of premium office space and is Boston's 22nd tallest building. This recognizable landmark was actually sold at auction in a headline-making transaction of roughly $400 million. Despite the large sale amount, the outcome of the auction highlights the dramatic devaluation of some Downtown Boston office properties over the last few years. Previously known as the State Street Financial Center, One Lincoln underwent a major change in 2023 when State Street moved its headquarters to a newly constructed building in Government Center, the One Congress Tower. This left the property with a roughly 750,000-square-foot vacancy gap to fill at a point when most office tenants were looking to downsize or offload their real estate footprints. The tower was last acquired for just short of $900 million back when it was fully leased in late 2006. Just three years ago, the building’s former owner refinanced the property for $1 Billion. This decline in value - from a $1 billion refinancing to a $400 million foreclosure sale - underscores some of the ongoing struggles within the city's commercial real estate market , particularly in the wake of shifting work patterns and the ongoing impact of the COVID-19 pandemic.

 574 East 3rd Street - South Boston 3 Family$1,999,000Living Area - 3,639 Sq. Ft.Total Area - 5,043 Sq. Ft.Lot Size - 4,...
10/29/2025



574 East 3rd Street - South Boston 3 Family

$1,999,000

Living Area - 3,639 Sq. Ft.
Total Area - 5,043 Sq. Ft.
Lot Size - 4,800 Sq. Ft.

Large, Detached South Boston 3 Family! This “East Side” Southie multifamily property is fully rented with an annual gross income of $126,000 and all leases going until 8/31/26. This multi-generational, longtime family-owned home and income property has an outstanding rental history and presents an opportunity for a continued long-term hold (with TLC, as is, or with value-add renovations), a condo conversion, redevelopment, or eventual owner occupancy. Situated on a 4,800 sq. ft. lot with a large backyard, this building features an unfinished basement and three spacious 3 BR / 1 BA apartments with laundry in each unit, bay windows, hardwoods, back porches, and nicely sized bedrooms. Fantastic location in the heart of South Boston, in close proximity to the Edison Plant redevelopment, East Broadway, The Seaport, Castle Island, Carson Beach, the MBTA, and all that Southie and Boston have to offer. Outstanding opportunity in one of the nation’s most sought after multifamily markets!

  pleased to have helped my buyer clients beat out multiple offers and secure this great home in a super competitive sub...
10/18/2025

pleased to have helped my buyer clients beat out multiple offers and secure this great home in a super competitive suburban market!

Sold! Pleased to have helped my developer clients succesfully sell their latest new construction single family developme...
09/22/2025

Sold! Pleased to have helped my developer clients succesfully sell their latest new construction single family development in Norfolk, MA.

Address

Boston, MA
02116

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