Josh Stiles

(617) 581-5907

Office

126 Newbury St #5
Boston MA, 02116

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  • Top Boston Real Estate Expert

    Josh Stiles

Trusted. Experienced. Professional.

Red-brick house with arched windows, landscaped gardens, and a curved stone-paved driveway.

Buy

 Elegant entry hall with arched windows, ornate molding, a long rug, and an upholstered bench.

Let's Connect

 Furnished living room with a tall white brick fireplace, chandelier, and built-in shelves.

Sell
Josh Stiles Boston, MA Real Estate Agent Headshot

Meet Josh

Josh Stiles | Boston & Greater Boston Real Estate Agent

Josh Stiles is a top-producing Boston real estate agent specializing in luxury homes, condominiums, residential real estate, and investment properties throughout Boston and Greater Boston, Massachusetts. With over $200 million in real estate sales, Josh represents buyers, sellers, and investors across some of Boston's most desirable neighborhoods and communities.

Josh's real estate expertise spans Boston, Back Bay, Beacon Hill, Downtown Boston, the South End, North End, Seaport District, Jamaica Plain, South Boston, Brookline, Newton, Milton, Cambridge, and Somerville. From luxury condominiums in Back Bay and Beacon Hill to historic brownstones in the South End, waterfront residences in the Seaport District, and single-family homes in Brookline, Newton, and Milton, Josh provides personalized guidance tailored to each client's goals.

Recognized as a Boston Magazine Top Producer and nationally honored as one of REALTOR® Magazine's 2019 30 Under 30, Josh brings a proven track record, local market knowledge, and a client-first approach to every transaction.

As a Seller's and Buyer's Specialist® and committee member of the Greater Boston Association of REALTORS®, Josh provides strategic advice on property pricing, luxury home marketing, real estate negotiations, investment opportunities, and navigating Boston's competitive housing market.

Whether helping homeowners sell luxury properties, assisting buyers in finding their ideal Boston home, advising real estate investors, or guiding clients relocating to Greater Boston, Josh is known for his responsiveness, resourcefulness, and personalized service.

Josh believes successful real estate transactions begin with understanding each client's individual needs. His approach combines local market insight, thoughtful strategy, and strong relationships to help clients make confident real estate decisions.

For those looking to buy, sell, or invest in Boston or Greater Boston real estate, Josh Stiles offers extensive experience, proven results, and dedicated representation.

Proven Record

12+

YEARS OF EXPERIENCE

200+

CLOSED SALES

$200+M

TOTAL VALUE

Featured Listings

  • 4 Woodland Road For Sale

    $900,000

    4 Woodland Road, Georgetown, MA 01833

    • 4 Beds
    • 3 Baths
    • 2,464 Sq.Ft.
  • Kitchen with a wood island, stainless-steel appliances, and stairs opening to a furnished living area. Active Under Contract

    $899,000

    127 Winthrop Road # 1A, Brookline, MA 02445

    • 2 Beds
    • 2 Baths
    • 1,095 Sq.Ft.
  • Open-plan living and dining room with white kitchen cabinetry, a black dining table, and green ottomans. For Lease

    $10,500/mo

    222 Austin St # 222, Newton, MA 02465

    • 4 Beds
    • 5 Baths
    • 3,635 Sq.Ft.
  • Blue multi-story house with white trim, bay windows, and a covered front porch. For Lease

    $4,300/mo

    4 Fayette Park # 2, Cambridge, MA 02139

    • 3 Beds
    • 1 Bath
    • 1,050 Sq.Ft.
  • Bright living room with a blue sofa, hardwood floors, and glass-paneled doors. For Lease

    $3,500/mo

    1228 Cambridge Street Unit: 2, Cambridge, MA 02139

    • 3 Beds
    • 1 Bath
    • 895 Sq.Ft.
  • Bedroom with a white metal bed, blue accents, and two shuttered windows. For Lease

    $2,000/mo

    31 1/2 Englewood Ave # 5, Brookline, MA 02445

    • 2 Beds
    • 1 Bath
    • 792 Sq.Ft.
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Success Stories

In addition to Josh being a consummate professional – reliable, respectful, being available 24(well, almost)/7, etc. - it was his pleasant and easy-going attitude that I benefited from in no small measure because it made me feel more relaxed about the whole process. Even with a deadline looming, I never doubted that he would find the right apartment for me - and he did. Would I recommend him to my friends? Not only that, when the time comes for me to move again, Josh, I'll be looking for you!
In addition to Josh being a consummate professional – reliable, respectful, being available 24(well, almost)/7, etc. - it was his pleasant and easy-going attitude that I benefited from in no small measure because it made me feel more relaxed about the whole process. Even with a deadline looming, I never doubted that he would find the right apartment for me - and he did. Would I recommend him to my friends? Not only that, when the time comes for me to move again, Josh, I'll be looking for you!
Rudy M.
We recently spent 2 and a half days in the Boston and Cambridge area searching for a starter apartment. Josh was instrumental in helping us navigate this whirlwind search. Of course, Josh helped us set up appointments to see apartments on very short notice. More importantly, he helped us by becoming a neighborhood tour guide so that we could narrow down our search on a dime. We would highly recommend working with Josh. It was a true pleasure!
We recently spent 2 and a half days in the Boston and Cambridge area searching for a starter apartment. Josh was instrumental in helping us navigate this whirlwind search. Of course, Josh helped us set up appointments to see apartments on very short notice. More importantly, he helped us by becoming a neighborhood tour guide so that we could narrow down our search on a dime. We would highly recommend working with Josh. It was a true pleasure!
Tamar H.
Josh is a responsive, reliable, and energetic broker who will do what it takes to find you the home or apartment you want. He took our needs into account and made sure we saw properties that matched our criteria. He was quick to make appointments and manage paperwork. He is also very pleasant and unfailingly polite. I recommend him highly.
Josh is a responsive, reliable, and energetic broker who will do what it takes to find you the home or apartment you want. He took our needs into account and made sure we saw properties that matched our criteria. He was quick to make appointments and manage paperwork. He is also very pleasant and unfailingly polite. I recommend him highly.
Marsha M.
Josh is a great realtor, and we are very happy to have worked with him and found our new place! Communication with Josh was fast and efficient, and we were able to see many places in a short period of time. We were new to the process, and Josh helped us all the way to signing the lease, explaining the intricacies and making us feel confident in our choice. We strongly recommend his services.
Josh is a great realtor, and we are very happy to have worked with him and found our new place! Communication with Josh was fast and efficient, and we were able to see many places in a short period of time. We were new to the process, and Josh helped us all the way to signing the lease, explaining the intricacies and making us feel confident in our choice. We strongly recommend his services.
Dor A.
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Neighborhood Guides

  • Back Bay
  • South End
  • Bay Village
  • Beacon Hill
  • Seaport District
  • Brookline
  • Newton
  • Cambridge
  • Somerville
  • Milton
  • Boston’s Back Bay skyline above a leafy park, including glass towers and historic brick buildings.

    Explore Back Bay

    42.35071° N, -71.07973° W

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  • Boston skyline beyond South End brick row houses in golden-hour light.

    Explore South End

    42.33964° N, -71.07453° W

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  • Red-brick townhouses with dark shutters and dormer windows behind a fenced lawn and mature trees.

    Explore Bay Village

    42.34841° N, -71.06931° W

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  • Beacon Hill street with brick buildings, iron fire escapes, and a traditional streetlamp.

    Explore Beacon Hill

    42.3598° N, -71.0662° W

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  • Boston Seaport waterfront with glass office towers, a bridge, and a rowing shell.

    Explore Seaport District

    42.34810° N, -71.04043° W

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  • Red-brick house with a slate roof, arched windows, and a landscaped front yard.

    Explore Brookline

    42.332218° N, -71.121483° W

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  • Aerial view of a leafy town center with a historic stone church and a lake in the distance.

    Explore Newton

    42.341042° N, -71.217133° W

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  • Aerial view of a red-brick complex with a red-domed cupola, courtyard, and Cambridge skyline.

    Explore Cambridge

    42.373611° N, -71.110558° W

    Read More
  • Aerial view of Somerville neighborhoods with the Boston skyline in the distance.

    Explore Somerville

    42.387959° N, -71.103088° W

    Read More
  • Autumn trees and blue sky reflected in a calm lake.

    Explore Milton

    42.250683° N, -71.071663° W

    Read More
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Josh Stiles

(617) 581-5907

126 Newbury St #5 Boston MA 02116

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Josh Stiles

(617) 581-5907

126 Newbury St #5 Boston MA 02116