Hilary Maddox's Profile Photo

Hilary Maddox

Managing Director

Awards

2025: REAL Trends ‘America’s Best’ Real Estate Professionals List

Education

B.A. Princeton University - Majored in History of Science
Princeton Womens Lacrosse - 1996-2000 (Captain); National Championship Runner-Up (2000)

Charity

Proudly Supports:

Camp Harborview
The Brookline Teen Center
Brookline Youth Lacrosse - Youth Boys Coach
About Hilary
A 15+ year resident of Brookline, Hilary Maddox has high energy, a knack for numbers, and a passion for real estate. Hilary began her career in finance, spending six years in investment banking and venture capital before deciding to get out from behind the desk. She now uses her problem-solving skills, specialized market knowledge, and negotiating skills to help her clients' meet their real estate needs. Hilary is known for her enthusiasm, strong work ethic, trustworthiness and winning attitude.

Hilary grew up in a family that loves renovating. She has always had an an eye for design and a deep appreciation for the architectural integrity of a house. She also loves the challenge of a project: she completed a gut renovation of her 1890’s Pill Hill home, where she now lives with her two sons.

Hilary moved to Brookline at the age of six, where she attended the Park School before Groton School and Princeton University. At Princeton, she captained the Women’s Lacrosse team, leading the team to the National Championship Finals. Hilary brings the same high standards of leadership, dedication and teamwork to her real estate practice. She is committed to working hard, while having fun in the process. When she's not working or playing with her kids, Hilary loves wearing through her running shoes, exploring new restaurants, and finding the next best place to travel.

Hilary Maddox’s Listings

$5,250,000 | 8 Holly Road, Newton, MA 02468
1/36
Listed By CompassUnder Agreement

$5,250,000

Bedrooms
6
Bathrooms
6
Square Feet
8,502
Acres
0.77
a front view of a house with yard and green space
1/35
Listed By Compass

$5,250,000

Bedrooms
7
Bathrooms
6
Square Feet
6,193
Acres
0.96
$2,995,000 | 7 Dana Street, Brookline, MA 02445
1/28
Listed By CompassUnder Agreement

$2,995,000

Bedrooms
5
Bathrooms
3
Square Feet
3,315
Acres
0.12
$2,770,000 | 291 Goddard Avenue, Unit 291, Brookline, MA 02445
1/20
Listed By Compass

$2,770,000

Bedrooms
3
Bathrooms
4
Square Feet
3,209
Acres
Unavailable

Hilary Maddox’s Transactions

Past Sales
$7,250,000 | 85 Sears Road, Brookline, MA 02445

$7,250,000

Bedrooms
9
Bathrooms
7
Square Feet
8,482
Acres
1.13
a front view of a house with garden

$6,850,000

Bedrooms
4
Bathrooms
4
Square Feet
4,647
Acres
0.16
$6,675,000 | 59 High Street, Brookline, MA 02445

$6,675,000

Bedrooms
6
Bathrooms
8
Square Feet
7,450
Acres
0.50
$6,288,000 | 99 Sargent Road, Brookline, MA 02445

$6,288,000

Bedrooms
6
Bathrooms
7
Square Feet
8,841
Acres
1.44
a front view of a house with porch

$6,000,008

Bedrooms
8
Bathrooms
6
Square Feet
6,535
Acres
0.89
$5,995,000 | 248 Buckminster Road, Brookline, MA 02445

$5,995,000

Bedrooms
7
Bathrooms
6
Square Feet
7,722
Acres
0.56
a front view of a house with a yard

$5,700,000

Bedrooms
7
Bathrooms
6
Square Feet
5,800
Acres
0.54
a front view of a house with a yard table and chairs

$5,500,000

Bedrooms
6
Bathrooms
5
Square Feet
6,313
Acres
0.81
$5,100,000 | 294 Buckminster Road, Brookline, MA 02445

$5,100,000

Bedrooms
6
Bathrooms
8
Square Feet
8,475
Acres
0.65
$4,800,000 | 13 Cazenove Street, Boston, MA 02116

$4,800,000

Bedrooms
5
Bathrooms
5
Square Feet
3,518
Acres
0.03
a view of a volley ball court

$4,700,000

Bedrooms
7
Bathrooms
6
Square Feet
5,901
Acres
1.00

41 Codman Road, Brookline, MA 02445

a view of a big house with a big yard and large trees

$4,600,000

Bedrooms
7
Bathrooms
6
Square Feet
4,227
Acres
1.42
$4,500,000 | 321 Warren Street, Brookline, MA 02445

$4,500,000

Bedrooms
7
Bathrooms
6
Square Feet
6,176
Acres
0.82
$4,500,000 | 41 Codman Road, Brookline, MA 02445

$4,500,000

Bedrooms
7
Bathrooms
5
Square Feet
6,637
Acres
1.00
$4,400,000 | 375 Lee Street, Brookline, MA 02445

$4,400,000

Bedrooms
5
Bathrooms
6
Square Feet
6,829
Acres
1.02
$4,188,888 | 45 Warren Street, Brookline, MA 02445

$4,188,888

Bedrooms
7
Bathrooms
5
Square Feet
4,525
Acres
0.76
Past Rentals
a front view of a house with garden

$9,000

Bedrooms
5
Bathrooms
5
$3,000 | 22 Ackers Avenue, Unit 1, Brookline, MA 02445

$3,000

Bedrooms
3
Bathrooms
1