Josh Stiles's profile photo

Josh Stiles

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

Awards

RealTrends Verified, 2025

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 $150 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

$4,500,000 | 666 Massachusetts Avenue, Boston, MA 02118
1/30
Listed By CompassVirtual Tour

$4,500,000

Bedrooms
9
Bathrooms
7
Square Feet
5,050
Acres
Unavailable

666 Massachusetts Avenue, Boston, MA 02118

a kitchen with granite countertop a table chairs sink and cabinets
1/34
Listed By CompassUnder Agreement

$1,900,000

Bedrooms
4
Bathrooms
2
Square Feet
2,204

48 Marshal Street, Unit C, Brookline, MA 02446

Josh Stiles’ Transactions

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

$10,200,000

Bedrooms
5
Bathrooms
6
Square Feet
4,703

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

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

$4,360,000

Bedrooms
9
Bathrooms
7
Square Feet
5,335
Acres
0.04

666 Massachusetts Avenue, Boston, MA 02118

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

$4,000,000

Bedrooms
6
Bathrooms
5
Square Feet
5,106
Acres
0.23

96 Dean Road, Brookline, MA 02445

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

$4,000,000

Bedrooms
10
Bathrooms
10
Square Feet
5,334
Acres
0.03

104 Prince Street, Boston, MA 02113

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

$2,725,000

Bedrooms
2

476 Beacon St Unit 2

Back Bay

a car parked in front of a building

$2,325,000

Bedrooms
5
Bathrooms
4
Square Feet
2,940
Acres
0.05

21 Wellington Street, Boston, MA 02118

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

$2,200,000

Bedrooms
6
Bathrooms
3
Square Feet
3,025
Acres
0.06

4 Fayette Park, Cambridge, MA 02139

a view of an empty room with a fireplace

$2,100,000

Bedrooms
2
Bathrooms
2
Square Feet
1,531

50 Rutland Square, Unit PH5, Boston, MA 02118

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

$1,950,000

Bedrooms
3
Bathrooms
3
Square Feet
2,308
Acres
0.06

24 Bowdoin Street, Cambridge, MA 02138

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

$1,830,000

Bedrooms
3
Bathrooms
4
Square Feet
3,669

20 Hamlet Street, Unit 20, Newton, MA 02459

a view of a patio with a table and chairs

$1,825,000

Bedrooms
4
Bathrooms
3
Square Feet
1,762

11 Flagg Street, Unit 2, Cambridge, MA 02138

a living room with furniture and a large window

$1,754,000

Bedrooms
4
Bathrooms
5
Square Feet
3,635

222 Austin Street, Unit 222, Newton, MA 02465

a living room with furniture and a large window

$1,700,000

Bedrooms
2
Bathrooms
3
Square Feet
1,573

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

a front view of a house with garden

$1,700,000

Bedrooms
6
Bathrooms
3
Square Feet
4,340
Acres
0.12

30-32 Goodrich Road, Boston, MA 02130

$1,675,000 | 10 Hill Street, Winchester, MA 01890

$1,675,000

Bedrooms
5
Bathrooms
5
Square Feet
3,600
Acres
0.15

10 Hill Street, Winchester, MA 01890

a front view of a house with garden

$1,550,000

Bedrooms
6
Bathrooms
5
Square Feet
4,705
Acres
0.96

59 Crestview Road, Milton, MA 02186

a living room with furniture and a large window

$1,495,000

Bedrooms
2
Bathrooms
2
Square Feet
1,730

8 Museum Way, Unit 1706, Cambridge, MA 02141

an aerial view of a house with a yard

Contact Agent

Bedrooms
5
Bathrooms
4
Square Feet
4,500
Acres
0.38

11 Craig Hill Lane, Milton, MA 02186

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

$8,900

Bedrooms
4
Bathrooms
4

40 Foley Beach Road, Hingham, MA 02043

a kitchen with stainless steel appliances a refrigerator sink and stove

$6,250

Bedrooms
3
Bathrooms
3

45 Clarendon Street, Unit 1, Boston, MA 02116

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

$5,950

Bedrooms
4
Bathrooms
2

84 Pemberton Street, Cambridge, MA 02140

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

$5,300

Bedrooms
2
Bathrooms
2

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

a living room with furniture and a fireplace

$5,200

Bedrooms
2
Bathrooms
3

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

a living room with furniture and a fireplace

$5,000

Bedrooms
3
Bathrooms
2

152 Warren Avenue, Unit PH, Boston, MA 02116

a living room with furniture and a large window

$4,800

Bedrooms
2
Bathrooms
2

424 Massachusetts Avenue, Unit 202, Boston, MA 02118

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

$4,300

Bedrooms
3
Bathrooms
2

9 Hanover Avenue, Unit 3, Boston, MA 02109

a view of a house with a large windows

$4,200

Bedrooms
2
Bathrooms
2

384 Windsor Street, Unit 2, Cambridge, MA 02141

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

$4,200

Bedrooms
1
Bathrooms
1

6 Wellington Street, Unit 4, Boston, MA 02118

a front view of a house with a yard

$4,200

Bedrooms
3
Bathrooms
1

4 Fayette Park, Unit 2, Cambridge, MA 02139

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

$4,200

Bedrooms
2
Bathrooms
1
Square Feet
705

97 Waltham Street, Unit 6, Boston, MA 02118

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

$4,100

Bedrooms
2
Bathrooms
2

666 Massachusetts Avenue, Unit 2, Boston, MA 02118

a front view of a building

$4,000

Bedrooms
2
Bathrooms
2

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

Bedrooms
2
Bathrooms
2

666 Massachusetts Avenue, Unit 2, Boston, MA 02118

a living room with furniture and a flat screen tv

$3,900

Bedrooms
2
Bathrooms
2

104 Prince Street, Unit 4, Boston, MA 02113

$3,900 | 130 St Marys Street, Unit 1, Boston, MA 02215

$3,900

Bedrooms
2
Bathrooms
2

130 St Marys Street, Unit 1, Boston, MA 02215

a living room with furniture and a fireplace

$3,850

Bedrooms
2
Bathrooms
1

34 Station Street, Unit 2, Brookline, MA 02445