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

a view of a house with swimming pool and sitting area
a view of a dining room with furniture and window
a living room with furniture a fireplace and a flat screen tv
a living room with fireplace furniture and a large window
a view of a dining room with furniture and wooden floor
a living room with furniture and a window
a spacious bedroom with a large bed and a fireplace
a living room with furniture and a fireplace
a bathroom with a sink and a mirror
a bedroom with a bed and a window
a bathroom with a sink toilet and mirror
a bedroom with a bed and a window
a living room with furniture and a large window
a bedroom with a bed and with chair
a front view of a house with a yard swimming pool and outdoor seating
a view of a house with a yard and a large pool
an aerial view of a house with a yard and lake view
$4,995,000 | 40 Heath Hill, Brookline, MA 02445
$4,995,000 | 40 Heath Hill, Brookline, MA 02445
$4,995,000 | 40 Heath Hill, Brookline, MA 02445
$4,995,000 | 40 Heath Hill, Brookline, MA 02445
$4,995,000 | 40 Heath Hill, Brookline, MA 02445
$4,995,000 | 40 Heath Hill, Brookline, MA 02445
$4,995,000 | 40 Heath Hill, Brookline, MA 02445
$4,995,000 | 40 Heath Hill, Brookline, MA 02445
$4,995,000 | 40 Heath Hill, Brookline, MA 02445
$4,995,000 | 40 Heath Hill, Brookline, MA 02445
$4,995,000 | 40 Heath Hill, Brookline, MA 02445
$4,995,000 | 40 Heath Hill, Brookline, MA 02445
$4,995,000 | 40 Heath Hill, Brookline, MA 02445
$4,995,000 | 40 Heath Hill, Brookline, MA 02445
$4,995,000 | 40 Heath Hill, Brookline, MA 02445
$4,995,000 | 40 Heath Hill, Brookline, MA 02445
$4,995,000 | 40 Heath Hill, Brookline, MA 02445
$4,995,000 | 40 Heath Hill, Brookline, MA 02445
$4,995,000 | 40 Heath Hill, Brookline, MA 02445
$4,995,000 | 40 Heath Hill, Brookline, MA 02445
$4,995,000 | 40 Heath Hill, Brookline, MA 02445
$4,995,000 | 40 Heath Hill, Brookline, MA 02445
$4,995,000 | 40 Heath Hill, Brookline, MA 02445
1/40
Listed By Compass

$4,995,000

7
Bedrooms
6,560
Square Feet
0.72
Acres
$4,895,000 | 16 Merrill Road, Newton, MA 02459
$4,895,000 | 16 Merrill Road, Newton, MA 02459
$4,895,000 | 16 Merrill Road, Newton, MA 02459
$4,895,000 | 16 Merrill Road, Newton, MA 02459
$4,895,000 | 16 Merrill Road, Newton, MA 02459
$4,895,000 | 16 Merrill Road, Newton, MA 02459
$4,895,000 | 16 Merrill Road, Newton, MA 02459
$4,895,000 | 16 Merrill Road, Newton, MA 02459
$4,895,000 | 16 Merrill Road, Newton, MA 02459
$4,895,000 | 16 Merrill Road, Newton, MA 02459
$4,895,000 | 16 Merrill Road, Newton, MA 02459
$4,895,000 | 16 Merrill Road, Newton, MA 02459
$4,895,000 | 16 Merrill Road, Newton, MA 02459
$4,895,000 | 16 Merrill Road, Newton, MA 02459
$4,895,000 | 16 Merrill Road, Newton, MA 02459
$4,895,000 | 16 Merrill Road, Newton, MA 02459
$4,895,000 | 16 Merrill Road, Newton, MA 02459
$4,895,000 | 16 Merrill Road, Newton, MA 02459
$4,895,000 | 16 Merrill Road, Newton, MA 02459
$4,895,000 | 16 Merrill Road, Newton, MA 02459
$4,895,000 | 16 Merrill Road, Newton, MA 02459
$4,895,000 | 16 Merrill Road, Newton, MA 02459
$4,895,000 | 16 Merrill Road, Newton, MA 02459
$4,895,000 | 16 Merrill Road, Newton, MA 02459
$4,895,000 | 16 Merrill Road, Newton, MA 02459
$4,895,000 | 16 Merrill Road, Newton, MA 02459
$4,895,000 | 16 Merrill Road, Newton, MA 02459
1/27
Listed By CompassOpen: 4/26 12:00PM - 01:00PM

$4,895,000

6
Bedrooms
7,667
Square Feet
0.39
Acres
Contact Agent | 185 Warren Street, Brookline, MA 02445
Contact Agent | 185 Warren Street, Brookline, MA 02445
Contact Agent | 185 Warren Street, Brookline, MA 02445
Contact Agent | 185 Warren Street, Brookline, MA 02445
Contact Agent | 185 Warren Street, Brookline, MA 02445
Contact Agent | 185 Warren Street, Brookline, MA 02445
Contact Agent | 185 Warren Street, Brookline, MA 02445
Contact Agent | 185 Warren Street, Brookline, MA 02445
Contact Agent | 185 Warren Street, Brookline, MA 02445
Contact Agent | 185 Warren Street, Brookline, MA 02445
Contact Agent | 185 Warren Street, Brookline, MA 02445
Contact Agent | 185 Warren Street, Brookline, MA 02445
Contact Agent | 185 Warren Street, Brookline, MA 02445
Contact Agent | 185 Warren Street, Brookline, MA 02445
Contact Agent | 185 Warren Street, Brookline, MA 02445
Contact Agent | 185 Warren Street, Brookline, MA 02445
Contact Agent | 185 Warren Street, Brookline, MA 02445
Contact Agent | 185 Warren Street, Brookline, MA 02445
1/18
Compass Coming Soon

Contact Agent

5
Bedrooms
2,834
Square Feet
0.92
Acres
a living room with furniture and a large window
a view of furniture and a potted plant on a kitchen counter top
a bedroom with a bed and a window
a kitchen with stainless steel appliances granite countertop a stove and a sink
a kitchen with stainless steel appliances granite countertop a stove microwave and refrigerator
a bathroom with a granite countertop toilet a sink and a mirror
a bathroom with a granite countertop sink a toilet and a mirror
a view of a building
1/8
Listed By CompassUnder Agreement

$439,000

Studio
Bedrooms
407
Square Feet

Hilary Maddox’s Transactions

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

$7,250,000

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

$6,850,000

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

$6,675,000

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

$6,288,000

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

$6,000,008

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

$5,995,000

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

$5,700,000

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

$5,500,000

6
Bedrooms
6,313
Square Feet
0.81
Acres
a front view of a house with a yard and garage

$5,250,000

7
Bedrooms
6,193
Square Feet
0.96
Acres
$5,100,000 | 294 Buckminster Road, Brookline, MA 02445

$5,100,000

6
Bedrooms
8,475
Square Feet
0.65
Acres
a front view of a house with a yard

$4,825,000

6
Bedrooms
8,502
Square Feet
0.77
Acres
$4,800,000 | 13 Cazenove Street, Boston, MA 02116

$4,800,000

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

$4,700,000

7
Bedrooms
5,901
Square Feet
1.00
Acres

41 Codman Road, Brookline, MA 02445

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

$4,600,000

7
Bedrooms
4,227
Square Feet
1.42
Acres
a front view of a house with a yard

$4,500,000

6
Bedrooms
5,461
Square Feet
0.52
Acres
$4,500,000 | 321 Warren Street, Brookline, MA 02445

$4,500,000

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

$4,500,000

7
Bedrooms
6,637
Square Feet
1.00
Acres
Past Rentals
a front view of a house with garden

$9,000

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

$3,000

3
Bedrooms