Josh Stiles

Josh Stiles

Vice President
josh.stiles@compass.com
M: 617-581-5907

Specialties

Seller Representative Specialist®
Accredited Buyer's Representative®
Greater Boston Association of REALTORS® Committee Member

Charity

Tenacity- Tenacity provides a Pathway to Post Secondary Success for underserved Boston students through education, fitness, and life skills programs.

Social Media

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Testimonials


About Josh
Josh Stiles specializes in Boston and Greater Boston residential real estate, luxury homes, and investment properties. Josh is recognized as a Boston Magazine Top Producer with over $200 million sold. He was awarded national recognition as 2019's Realtor Magazine's 30 under 30. Josh is a Seller's and Buyer’s Specialist®, and Committee member of the Greater Boston Association of REALTORS®.

As a highly motivated, resourceful, and exceptionally friendly Realtor®, Josh is always committed to his clients. His goal is to listen closely to his clients’ needs and connect them with opportunities that best match, and exceed, those needs.

Josh resides in Brookline with his wonderful family and their furry dog, Theo. During his free time, he is either playing tennis or paddle, traversing Boston for the next best meal, or spending time with family and friends in Provincetown, Cape Cod.

Josh graduated from Kenyon College with a Bachelors of Arts in Economics. As a collegiate athlete and team captain, he helped lead his team to 4 NCAA quarterfinals, 1 NCAA National Runner-Up Finish, and 1 NCAA National Indoor Championship.

Josh Stiles’ Listings

Contact Agent | 666 Massachusetts Avenue, Boston, MA 02118
Contact Agent | 666 Massachusetts Avenue, Boston, MA 02118
Contact Agent | 666 Massachusetts Avenue, Boston, MA 02118
Contact Agent | 666 Massachusetts Avenue, Boston, MA 02118
Contact Agent | 666 Massachusetts Avenue, Boston, MA 02118
Contact Agent | 666 Massachusetts Avenue, Boston, MA 02118
Contact Agent | 666 Massachusetts Avenue, Boston, MA 02118
Contact Agent | 666 Massachusetts Avenue, Boston, MA 02118
Contact Agent | 666 Massachusetts Avenue, Boston, MA 02118
Contact Agent | 666 Massachusetts Avenue, Boston, MA 02118
Contact Agent | 666 Massachusetts Avenue, Boston, MA 02118
Contact Agent | 666 Massachusetts Avenue, Boston, MA 02118
Contact Agent | 666 Massachusetts Avenue, Boston, MA 02118
Contact Agent | 666 Massachusetts Avenue, Boston, MA 02118
Contact Agent | 666 Massachusetts Avenue, Boston, MA 02118
Contact Agent | 666 Massachusetts Avenue, Boston, MA 02118
Contact Agent | 666 Massachusetts Avenue, Boston, MA 02118
Contact Agent | 666 Massachusetts Avenue, Boston, MA 02118
Contact Agent | 666 Massachusetts Avenue, Boston, MA 02118
Contact Agent | 666 Massachusetts Avenue, Boston, MA 02118
Contact Agent | 666 Massachusetts Avenue, Boston, MA 02118
Contact Agent | 666 Massachusetts Avenue, Boston, MA 02118
Contact Agent | 666 Massachusetts Avenue, Boston, MA 02118
Contact Agent | 666 Massachusetts Avenue, Boston, MA 02118
Contact Agent | 666 Massachusetts Avenue, Boston, MA 02118
Contact Agent | 666 Massachusetts Avenue, Boston, MA 02118
Contact Agent | 666 Massachusetts Avenue, Boston, MA 02118
Contact Agent | 666 Massachusetts Avenue, Boston, MA 02118
Contact Agent | 666 Massachusetts Avenue, Boston, MA 02118
Contact Agent | 666 Massachusetts Avenue, Boston, MA 02118
Contact Agent | 666 Massachusetts Avenue, Boston, MA 02118
Contact Agent | 666 Massachusetts Avenue, Boston, MA 02118
Contact Agent | 666 Massachusetts Avenue, Boston, MA 02118
Contact Agent | 666 Massachusetts Avenue, Boston, MA 02118
Contact Agent | 666 Massachusetts Avenue, Boston, MA 02118
Contact Agent | 666 Massachusetts Avenue, Boston, MA 02118
1/36
Compass Coming Soon

Contact Agent

9
Bedrooms
5,050
Square Feet
Unavailable
Acres

666 Massachusetts Avenue, Boston, MA 02118

$1,650,000 | 2 Laurel Street, Lexington, MA 02421
$1,650,000 | 2 Laurel Street, Lexington, MA 02421
$1,650,000 | 2 Laurel Street, Lexington, MA 02421
$1,650,000 | 2 Laurel Street, Lexington, MA 02421
$1,650,000 | 2 Laurel Street, Lexington, MA 02421
$1,650,000 | 2 Laurel Street, Lexington, MA 02421
$1,650,000 | 2 Laurel Street, Lexington, MA 02421
$1,650,000 | 2 Laurel Street, Lexington, MA 02421
$1,650,000 | 2 Laurel Street, Lexington, MA 02421
$1,650,000 | 2 Laurel Street, Lexington, MA 02421
$1,650,000 | 2 Laurel Street, Lexington, MA 02421
$1,650,000 | 2 Laurel Street, Lexington, MA 02421
$1,650,000 | 2 Laurel Street, Lexington, MA 02421
$1,650,000 | 2 Laurel Street, Lexington, MA 02421
$1,650,000 | 2 Laurel Street, Lexington, MA 02421
$1,650,000 | 2 Laurel Street, Lexington, MA 02421
$1,650,000 | 2 Laurel Street, Lexington, MA 02421
$1,650,000 | 2 Laurel Street, Lexington, MA 02421
$1,650,000 | 2 Laurel Street, Lexington, MA 02421
$1,650,000 | 2 Laurel Street, Lexington, MA 02421
$1,650,000 | 2 Laurel Street, Lexington, MA 02421
$1,650,000 | 2 Laurel Street, Lexington, MA 02421
$1,650,000 | 2 Laurel Street, Lexington, MA 02421
$1,650,000 | 2 Laurel Street, Lexington, MA 02421
$1,650,000 | 2 Laurel Street, Lexington, MA 02421
$1,650,000 | 2 Laurel Street, Lexington, MA 02421
$1,650,000 | 2 Laurel Street, Lexington, MA 02421
$1,650,000 | 2 Laurel Street, Lexington, MA 02421
$1,650,000 | 2 Laurel Street, Lexington, MA 02421
$1,650,000 | 2 Laurel Street, Lexington, MA 02421
$1,650,000 | 2 Laurel Street, Lexington, MA 02421
$1,650,000 | 2 Laurel Street, Lexington, MA 02421
$1,650,000 | 2 Laurel Street, Lexington, MA 02421
$1,650,000 | 2 Laurel Street, Lexington, MA 02421
$1,650,000 | 2 Laurel Street, Lexington, MA 02421
$1,650,000 | 2 Laurel Street, Lexington, MA 02421
$1,650,000 | 2 Laurel Street, Lexington, MA 02421
$1,650,000 | 2 Laurel Street, Lexington, MA 02421
$1,650,000 | 2 Laurel Street, Lexington, MA 02421
$1,650,000 | 2 Laurel Street, Lexington, MA 02421
$1,650,000 | 2 Laurel Street, Lexington, MA 02421
$1,650,000 | 2 Laurel Street, Lexington, MA 02421
$1,650,000 | 2 Laurel Street, Lexington, MA 02421
1/43
Compass Coming SoonVirtual Tour

$1,650,000

4
Bedrooms
2,544
Square Feet
0.39
Acres

2 Laurel Street, Lexington, MA 02421

$1,250,000 | 17 High Street, Unit 2, Brookline, MA 02445
$1,250,000 | 17 High Street, Unit 2, Brookline, MA 02445
$1,250,000 | 17 High Street, Unit 2, Brookline, MA 02445
$1,250,000 | 17 High Street, Unit 2, Brookline, MA 02445
$1,250,000 | 17 High Street, Unit 2, Brookline, MA 02445
$1,250,000 | 17 High Street, Unit 2, Brookline, MA 02445
$1,250,000 | 17 High Street, Unit 2, Brookline, MA 02445
$1,250,000 | 17 High Street, Unit 2, Brookline, MA 02445
$1,250,000 | 17 High Street, Unit 2, Brookline, MA 02445
$1,250,000 | 17 High Street, Unit 2, Brookline, MA 02445
$1,250,000 | 17 High Street, Unit 2, Brookline, MA 02445
$1,250,000 | 17 High Street, Unit 2, Brookline, MA 02445
$1,250,000 | 17 High Street, Unit 2, Brookline, MA 02445
$1,250,000 | 17 High Street, Unit 2, Brookline, MA 02445
$1,250,000 | 17 High Street, Unit 2, Brookline, MA 02445
$1,250,000 | 17 High Street, Unit 2, Brookline, MA 02445
$1,250,000 | 17 High Street, Unit 2, Brookline, MA 02445
$1,250,000 | 17 High Street, Unit 2, Brookline, MA 02445
$1,250,000 | 17 High Street, Unit 2, Brookline, MA 02445
$1,250,000 | 17 High Street, Unit 2, Brookline, MA 02445
$1,250,000 | 17 High Street, Unit 2, Brookline, MA 02445
$1,250,000 | 17 High Street, Unit 2, Brookline, MA 02445
1/22
Listed By CompassVirtual Tour

$1,250,000

4
Bedrooms
1,825
Square Feet

17 High Street, Unit 2, Brookline, MA 02445

$949,000 | 34 Station Street, Unit 3, Brookline, MA 02445
$949,000 | 34 Station Street, Unit 3, Brookline, MA 02445
$949,000 | 34 Station Street, Unit 3, Brookline, MA 02445
$949,000 | 34 Station Street, Unit 3, Brookline, MA 02445
$949,000 | 34 Station Street, Unit 3, Brookline, MA 02445
$949,000 | 34 Station Street, Unit 3, Brookline, MA 02445
$949,000 | 34 Station Street, Unit 3, Brookline, MA 02445
$949,000 | 34 Station Street, Unit 3, Brookline, MA 02445
$949,000 | 34 Station Street, Unit 3, Brookline, MA 02445
$949,000 | 34 Station Street, Unit 3, Brookline, MA 02445
$949,000 | 34 Station Street, Unit 3, Brookline, MA 02445
$949,000 | 34 Station Street, Unit 3, Brookline, MA 02445
$949,000 | 34 Station Street, Unit 3, Brookline, MA 02445
$949,000 | 34 Station Street, Unit 3, Brookline, MA 02445
$949,000 | 34 Station Street, Unit 3, Brookline, MA 02445
$949,000 | 34 Station Street, Unit 3, Brookline, MA 02445
$949,000 | 34 Station Street, Unit 3, Brookline, MA 02445
$949,000 | 34 Station Street, Unit 3, Brookline, MA 02445
$949,000 | 34 Station Street, Unit 3, Brookline, MA 02445
$949,000 | 34 Station Street, Unit 3, Brookline, MA 02445
$949,000 | 34 Station Street, Unit 3, Brookline, MA 02445
$949,000 | 34 Station Street, Unit 3, Brookline, MA 02445
$949,000 | 34 Station Street, Unit 3, Brookline, MA 02445
$949,000 | 34 Station Street, Unit 3, Brookline, MA 02445
$949,000 | 34 Station Street, Unit 3, Brookline, MA 02445
$949,000 | 34 Station Street, Unit 3, Brookline, MA 02445
1/26
Listed By CompassContingent

$949,000

2
Bedrooms
1,250
Square Feet

34 Station Street, Unit 3, Brookline, MA 02445

$615,000 | 20 Connecticut Avenue, Unit 2, Somerville, MA 02145
$615,000 | 20 Connecticut Avenue, Unit 2, Somerville, MA 02145
$615,000 | 20 Connecticut Avenue, Unit 2, Somerville, MA 02145
$615,000 | 20 Connecticut Avenue, Unit 2, Somerville, MA 02145
$615,000 | 20 Connecticut Avenue, Unit 2, Somerville, MA 02145
$615,000 | 20 Connecticut Avenue, Unit 2, Somerville, MA 02145
$615,000 | 20 Connecticut Avenue, Unit 2, Somerville, MA 02145
$615,000 | 20 Connecticut Avenue, Unit 2, Somerville, MA 02145
$615,000 | 20 Connecticut Avenue, Unit 2, Somerville, MA 02145
$615,000 | 20 Connecticut Avenue, Unit 2, Somerville, MA 02145
$615,000 | 20 Connecticut Avenue, Unit 2, Somerville, MA 02145
$615,000 | 20 Connecticut Avenue, Unit 2, Somerville, MA 02145
$615,000 | 20 Connecticut Avenue, Unit 2, Somerville, MA 02145
$615,000 | 20 Connecticut Avenue, Unit 2, Somerville, MA 02145
$615,000 | 20 Connecticut Avenue, Unit 2, Somerville, MA 02145
$615,000 | 20 Connecticut Avenue, Unit 2, Somerville, MA 02145
$615,000 | 20 Connecticut Avenue, Unit 2, Somerville, MA 02145
$615,000 | 20 Connecticut Avenue, Unit 2, Somerville, MA 02145
$615,000 | 20 Connecticut Avenue, Unit 2, Somerville, MA 02145
$615,000 | 20 Connecticut Avenue, Unit 2, Somerville, MA 02145
$615,000 | 20 Connecticut Avenue, Unit 2, Somerville, MA 02145
$615,000 | 20 Connecticut Avenue, Unit 2, Somerville, MA 02145
$615,000 | 20 Connecticut Avenue, Unit 2, Somerville, MA 02145
1/23
Listed By CompassUnder Agreement

$615,000

3
Bedrooms
950
Square Feet

20 Connecticut Avenue, Unit 2, Somerville, MA 02145

Josh Stiles’ Transactions

Past Sales
$10,200,000 | 2 Avery Street, Unit PH 2A, Boston, MA 02111

$10,200,000

5
Bedrooms
4,703
Square Feet

2 Avery Street, Unit PH 2A, Boston, MA 02111

$4,360,000 | 666 Massachusetts Avenue, Boston, MA 02118

$4,360,000

9
Bedrooms
5,335
Square Feet
0.04
Acres

666 Massachusetts Avenue, Boston, MA 02118

$4,000,000 | 104 Prince Street, Boston, MA 02113

$4,000,000

10
Bedrooms
5,334
Square Feet
0.03
Acres

104 Prince Street, Boston, MA 02113

$4,000,000 | 96 Dean Road, Brookline, MA 02445

$4,000,000

6
Bedrooms
5,106
Square Feet
0.23
Acres

96 Dean Road, Brookline, MA 02445

$3,280,000 | 14 Green Street, Unit PH1, Brookline, MA 02446

$3,280,000

3
Bedrooms
2,056
Square Feet

14 Green Street, Unit PH1, Brookline, MA 02446

$3,100,000 | 21 Wellington Lane, Belmont, MA 02478

$3,100,000

4
Bedrooms
5,199
Square Feet
0.48
Acres

21 Wellington Lane, Belmont, MA 02478

$2,725,000 | 476 Beacon St Unit 2 | Back Bay

$2,725,000

2
Bedrooms
2
Bathrooms

476 Beacon St Unit 2

Back Bay

a car parked in front of a building

$2,325,000

5
Bedrooms
2,940
Square Feet
0.05
Acres

21 Wellington Street, Boston, MA 02118

$2,200,000 | 4 Fayette Park, Cambridge, MA 02139

$2,200,000

6
Bedrooms
3,025
Square Feet
0.06
Acres

4 Fayette Park, Cambridge, MA 02139

Front courtyard leading to complex front entryway

$2,150,000

3
Bedrooms
3
Bathrooms

88 Wharf St, Unit 602

a view of an empty room with a fireplace

$2,100,000

2
Bedrooms
1,531
Square Feet

50 Rutland Square, Unit PH5, Boston, MA 02118

$1,950,000 | 24 Bowdoin Street, Cambridge, MA 02138

$1,950,000

3
Bedrooms
2,308
Square Feet
0.06
Acres

24 Bowdoin Street, Cambridge, MA 02138

front view of a house

$1,915,000

6
Bedrooms
3,493
Square Feet
0.20
Acres

228 Langley Road, Newton, MA 02459

$1,895,000 | 50 West Side Road, Milton, MA 02186

$1,895,000

4
Bedrooms
2,620
Square Feet
0.28
Acres

50 West Side Road, Milton, MA 02186

$1,830,000 | 20 Hamlet Street, Unit 20, Newton, MA 02459

$1,830,000

3
Bedrooms
3,669
Square Feet

20 Hamlet Street, Unit 20, Newton, MA 02459

a view of a patio with a table and chairs

$1,825,000

4
Bedrooms
1,762
Square Feet

11 Flagg Street, Unit 2, Cambridge, MA 02138

a front view of a house with plants

$1,825,000

3
Bedrooms
3,669
Square Feet

20 Hamlet Street, Unit 1, Newton, MA 02459

an aerial view of a house with a yard

Contact Agent

5
Bedrooms
4,500
Square Feet
0.38
Acres

11 Craig Hill Lane, Milton, MA 02186

Past Rentals
$8,900 | 40 Foley Beach Road, Hingham, MA 02043

$8,900

4
Bedrooms

40 Foley Beach Road, Hingham, MA 02043

a kitchen with stainless steel appliances a refrigerator sink and stove

$6,250

3
Bedrooms

45 Clarendon Street, Unit 1, Boston, MA 02116

$6,000 | 755 Boylston Street, Unit 804, Boston, MA 02116

$6,000

2
Bedrooms

755 Boylston Street, Unit 804, Boston, MA 02116

$5,950 | 84 Pemberton Street, Cambridge, MA 02140

$5,950

4
Bedrooms

84 Pemberton Street, Cambridge, MA 02140

$5,300 | 2 Avery Street, Unit 24H, Boston, MA 02111

$5,300

2
Bedrooms

2 Avery Street, Unit 24H, Boston, MA 02111

a living room with furniture and a fireplace

$5,200

2
Bedrooms

243 West Newton Street, Unit 1, Boston, MA 02116

a living room with furniture and a fireplace

$5,000

3
Bedrooms

152 Warren Avenue, Unit PH, Boston, MA 02116

$4,900 | 323 Boylston Street, Unit 201, Brookline, MA 02445

$4,900

2
Bedrooms

323 Boylston Street, Unit 201, Brookline, MA 02445

a living room with furniture and a large window

$4,800

2
Bedrooms

424 Massachusetts Avenue, Unit 202, Boston, MA 02118

$4,300 | 9 Hanover Avenue, Unit 3, Boston, MA 02109

$4,300

3
Bedrooms

9 Hanover Avenue, Unit 3, Boston, MA 02109

a front view of a house with a yard

$4,200

3
Bedrooms

4 Fayette Park, Unit 2, Cambridge, MA 02139

$4,200 | 97 Waltham Street, Unit 6, Boston, MA 02118

$4,200

2
Bedrooms
705
Square Feet

97 Waltham Street, Unit 6, Boston, MA 02118

a view of a house with a large windows

$4,200

2
Bedrooms

384 Windsor Street, Unit 2, Cambridge, MA 02141

$4,200 | 6 Wellington Street, Unit 4, Boston, MA 02118

$4,200

1
Bedrooms

6 Wellington Street, Unit 4, Boston, MA 02118

a kitchen with kitchen island a refrigerator a stove a sink and a oven with wooden floor

$4,100

2
Bedrooms

666 Massachusetts Avenue, Unit 2, Boston, MA 02118

a front view of a building

$4,000

2
Bedrooms

31 Millmont Street, Unit 1, Boston, MA 02119

a kitchen with kitchen island a refrigerator a stove a sink and a oven with wooden floor

$4,000

2
Bedrooms

666 Massachusetts Avenue, Unit 2, Boston, MA 02118

$3,900 | 104 Prince Street, Unit 5, Boston, MA 02113

$3,900

2
Bedrooms

104 Prince Street, Unit 5, Boston, MA 02113