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Matthew Giangregorio Real Estate Page - Charlesgate Realty Group

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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.

09/08/2026

42 Chauncy Street - Unit 4C
Boston, MA 02111

Offered at $699,000

838 Square Feet

Open Concept Studio Condominium

Condo Fee: $552

Experience true urban lifestyle living in this open-concept studio condo! Exceptional Opportunity in Boston’s Vibrant “Midtown” / Downtown Crossing! Located in The Edison, a historic former Edison Electric Co. building that was converted to a boutique, Manhattan-style, industrial loft condo building in 2001, this 838 Sq. Ft., 4th floor residence offers a flexible open floor plan with endless layout design possibilities. This condo features painted brick, gas cooking, a striking brushed stainless-steel backsplash rising from counter-to-ceiling & Laundry in Unit. Elevator building with authentic, chic & stylish industrial common areas with polished concrete floors & a Butterfly intercom system. Economical condo fee includes Heat, HW, gas cooking & Central Air. Located close to Millennium Tower, The Common, South Station & all that Downtown Boston has to offer. Rental garage parking across the street. A rare opportunity in one of Boston’s most desirable and rapidly rising neighborhoods! Reach Out For More Info! Boston Drone Video

09/07/2026

42 Chauncy Street - Unit 4C Boston, MA 02111

For Sale in Downtown Boston :

42 Chauncy Street - Unit 4C
Boston, MA 02111

Offered at $699,000

838 Square Feet

Open Concept Studio Condominium

Condo Fee: $552

Experience true urban lifestyle living in this open-concept studio condo! Exceptional Opportunity in Boston’s Vibrant “Midtown” / Downtown Crossing! Located in The Edison, a historic former Edison Electric Co. building that was converted to a boutique, Manhattan-style, industrial loft condo building in 2001, this 838 Sq. Ft., 4th floor residence offers a flexible open floor plan with endless layout design possibilities. This condo features painted brick, gas cooking, a striking brushed stainless-steel backsplash rising from counter-to-ceiling & Laundry in Unit. Elevator building with authentic, chic & stylish industrial common areas with polished concrete floors & a Butterfly intercom system. Economical condo fee includes Heat, HW, gas cooking & Central Air. Located close to Millennium Tower, The Common, South Station & all that Downtown Boston has to offer. Rental garage parking across the street. A rare opportunity in one of Boston’s most desirable and rapidly rising neighborhoods! Reach Out For More Info!

09/04/2026

338 Marlborough Street - Unit 2. Boston, MA

For Sale in Boston’s Back Bay:

338 Marlborough Street - Unit 2 Boston, MA

Offered at $949,000

820 Square Feet

1 Bedroom - 1 Bath Condominium

Condo Fee: $433

Exceptional Opportunity on one of Boston’s most prestigious streets! Set within a distinguished, classic Brownstone, this charming, floor-through 1BR / 1BA residence offers quintessential Back Bay living & architecture with one of Boston’s most coveted addresses. Blending timeless character with modern sensibility, this second-floor condominium opens into a spacious living / dining space framed by grand bay windows overlooking iconic, tree-lined Marlborough Street. High ceilings, rich hardwood floors, period details, abundant natural light, & decorative fireplaces establish a sense of timeless sophistication and appeal. The kitchen opens to the living area with a breakfast bar and features granite counters, SS appliances, exposed brick, and built-in w**e storage. Retreat to a generous bedroom and an adjacent bath with in-unit laundry. The best of a refined city living lifestyle, just moments to all that makes the historic Back Bay one of the nation’s most sought after neighborhoods. Reach Out For More Info!

Boston Drone Video

09/02/2026

For Sale in Boston’s Back Bay:
338 Marlborough Street - Unit 2 Boston, MA

Offered at $949,000

820 Square Feet

1 Bedroom - 1 Bath Condominium

Condo Fee: $433

Exceptional Opportunity on one of Boston's most prestigious streets! Set within a distinguished, classic Brownstone, this charming, floor-through 1BR / 1BA residence offers quintessential Back Bay living & architecture with one of Boston’s most coveted addresses. Blending timeless character with modern sensibility, this second-floor condominium opens into a spacious living / dining space framed by grand bay windows overlooking iconic, tree-lined Marlborough Street. High ceilings, rich hardwood floors, period details, abundant natural light, & decorative fireplaces establish a sense of timeless sophistication and appeal. The kitchen opens to the living area with a breakfast bar and features granite counters, SS appliances, exposed brick, and built-in w**e storage. Retreat to a generous bedroom and an adjacent bath with in-unit laundry. The best of a refined city living lifestyle, just moments to all that makes the historic Back Bay one of the nation’s most sought after neighborhoods. Reach Out For More Info!

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.

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!

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!

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!

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02116

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