Hilary Maddox's Profile Photo

Hilary Maddox

Managing Director
hilary.maddox@compass.com
M: 617-646-9003

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 street view of a building
a dining room with furniture and wooden floor
a view of a workspace with furniture
a living room with furniture and book shelf
a view of a dining room with furniture and rug
a living room with furniture cabinets and book shelf
a view of a kitchen and dining room
a living room with furniture and a fireplace
a bedroom with a bed and a flat screen tv
a bathroom with a sink and a mirror
a bedroom with a bed and wooden floor
a bedroom with a bed and a book shelf
a bathroom with a sink mirror vanity and toilet
a bedroom with a bed and a window
a living room with furniture cabinets and window
a living room with fireplace furniture and a flat screen tv
a front view of a house with a yard
a view of a patio with table and chairs and potted plants
a view of a pathway both side of the house
a view of a multi story building with a yard
unknown
1/21
Compass Coming Soon

Contact Agent

5
Bedrooms
3,937
Square Feet
Unavailable
Acres

Address Upon Request, Boston, MA 02114

$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
$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

40 Heath Hill, Brookline, MA 02445

$4,800,000 | 50 Sumner Road, Brookline, MA 02445
$4,800,000 | 50 Sumner Road, Brookline, MA 02445
$4,800,000 | 50 Sumner Road, Brookline, MA 02445
$4,800,000 | 50 Sumner Road, Brookline, MA 02445
$4,800,000 | 50 Sumner Road, Brookline, MA 02445
$4,800,000 | 50 Sumner Road, Brookline, MA 02445
$4,800,000 | 50 Sumner Road, Brookline, MA 02445
$4,800,000 | 50 Sumner Road, Brookline, MA 02445
$4,800,000 | 50 Sumner Road, Brookline, MA 02445
$4,800,000 | 50 Sumner Road, Brookline, MA 02445
$4,800,000 | 50 Sumner Road, Brookline, MA 02445
$4,800,000 | 50 Sumner Road, Brookline, MA 02445
$4,800,000 | 50 Sumner Road, Brookline, MA 02445
$4,800,000 | 50 Sumner Road, Brookline, MA 02445
$4,800,000 | 50 Sumner Road, Brookline, MA 02445
$4,800,000 | 50 Sumner Road, Brookline, MA 02445
$4,800,000 | 50 Sumner Road, Brookline, MA 02445
$4,800,000 | 50 Sumner Road, Brookline, MA 02445
$4,800,000 | 50 Sumner Road, Brookline, MA 02445
$4,800,000 | 50 Sumner Road, Brookline, MA 02445
$4,800,000 | 50 Sumner Road, Brookline, MA 02445
$4,800,000 | 50 Sumner Road, Brookline, MA 02445
$4,800,000 | 50 Sumner Road, Brookline, MA 02445
$4,800,000 | 50 Sumner Road, Brookline, MA 02445
$4,800,000 | 50 Sumner Road, Brookline, MA 02445
$4,800,000 | 50 Sumner Road, Brookline, MA 02445
$4,800,000 | 50 Sumner Road, Brookline, MA 02445
$4,800,000 | 50 Sumner Road, Brookline, MA 02445
$4,800,000 | 50 Sumner Road, Brookline, MA 02445
$4,800,000 | 50 Sumner Road, Brookline, MA 02445
$4,800,000 | 50 Sumner Road, Brookline, MA 02445
$4,800,000 | 50 Sumner Road, Brookline, MA 02445
1/32
Listed By Compass

$4,800,000

5
Bedrooms
5,423
Square Feet
0.41
Acres

50 Sumner Road, Brookline, MA 02445

$3,295,000 | 185 Warren Street, Brookline, MA 02445
$3,295,000 | 185 Warren Street, Brookline, MA 02445
$3,295,000 | 185 Warren Street, Brookline, MA 02445
$3,295,000 | 185 Warren Street, Brookline, MA 02445
$3,295,000 | 185 Warren Street, Brookline, MA 02445
$3,295,000 | 185 Warren Street, Brookline, MA 02445
$3,295,000 | 185 Warren Street, Brookline, MA 02445
$3,295,000 | 185 Warren Street, Brookline, MA 02445
$3,295,000 | 185 Warren Street, Brookline, MA 02445
$3,295,000 | 185 Warren Street, Brookline, MA 02445
$3,295,000 | 185 Warren Street, Brookline, MA 02445
$3,295,000 | 185 Warren Street, Brookline, MA 02445
$3,295,000 | 185 Warren Street, Brookline, MA 02445
$3,295,000 | 185 Warren Street, Brookline, MA 02445
$3,295,000 | 185 Warren Street, Brookline, MA 02445
$3,295,000 | 185 Warren Street, Brookline, MA 02445
$3,295,000 | 185 Warren Street, Brookline, MA 02445
$3,295,000 | 185 Warren Street, Brookline, MA 02445
$3,295,000 | 185 Warren Street, Brookline, MA 02445
$3,295,000 | 185 Warren Street, Brookline, MA 02445
$3,295,000 | 185 Warren Street, Brookline, MA 02445
$3,295,000 | 185 Warren Street, Brookline, MA 02445
$3,295,000 | 185 Warren Street, Brookline, MA 02445
$3,295,000 | 185 Warren Street, Brookline, MA 02445
$3,295,000 | 185 Warren Street, Brookline, MA 02445
1/25
Listed By CompassOpen: 6/6 01:00PM - 02:00PM

$3,295,000

5
Bedrooms
2,834
Square Feet
0.92
Acres

185 Warren Street, Brookline, MA 02445

$3,200,000 | 80 Mason Terrace, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Brookline, MA 02446
1/25
Listed By CompassContingent

$3,200,000

5
Bedrooms
3,680
Square Feet
0.36
Acres

80 Mason Terrace, Brookline, MA 02446

$3,200,000 | 80 Mason Terrace, Unit 80, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Unit 80, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Unit 80, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Unit 80, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Unit 80, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Unit 80, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Unit 80, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Unit 80, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Unit 80, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Unit 80, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Unit 80, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Unit 80, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Unit 80, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Unit 80, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Unit 80, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Unit 80, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Unit 80, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Unit 80, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Unit 80, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Unit 80, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Unit 80, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Unit 80, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Unit 80, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Unit 80, Brookline, MA 02446
$3,200,000 | 80 Mason Terrace, Unit 80, Brookline, MA 02446
1/25
Listed By CompassContingent

$3,200,000

5
Bedrooms
3,680
Square Feet

80 Mason Terrace, Unit 80, Brookline, MA 02446

$2,850,000 | 401 Heath Street, Brookline, MA 02467
$2,850,000 | 401 Heath Street, Brookline, MA 02467
$2,850,000 | 401 Heath Street, Brookline, MA 02467
$2,850,000 | 401 Heath Street, Brookline, MA 02467
$2,850,000 | 401 Heath Street, Brookline, MA 02467
$2,850,000 | 401 Heath Street, Brookline, MA 02467
$2,850,000 | 401 Heath Street, Brookline, MA 02467
$2,850,000 | 401 Heath Street, Brookline, MA 02467
$2,850,000 | 401 Heath Street, Brookline, MA 02467
$2,850,000 | 401 Heath Street, Brookline, MA 02467
$2,850,000 | 401 Heath Street, Brookline, MA 02467
$2,850,000 | 401 Heath Street, Brookline, MA 02467
$2,850,000 | 401 Heath Street, Brookline, MA 02467
$2,850,000 | 401 Heath Street, Brookline, MA 02467
$2,850,000 | 401 Heath Street, Brookline, MA 02467
$2,850,000 | 401 Heath Street, Brookline, MA 02467
$2,850,000 | 401 Heath Street, Brookline, MA 02467
$2,850,000 | 401 Heath Street, Brookline, MA 02467
$2,850,000 | 401 Heath Street, Brookline, MA 02467
$2,850,000 | 401 Heath Street, Brookline, MA 02467
$2,850,000 | 401 Heath Street, Brookline, MA 02467
$2,850,000 | 401 Heath Street, Brookline, MA 02467
$2,850,000 | 401 Heath Street, Brookline, MA 02467
$2,850,000 | 401 Heath Street, Brookline, MA 02467
$2,850,000 | 401 Heath Street, Brookline, MA 02467
$2,850,000 | 401 Heath Street, Brookline, MA 02467
$2,850,000 | 401 Heath Street, Brookline, MA 02467
1/27
Listed By CompassOpen: 6/6 01:00PM - 02:00PM

$2,850,000

5
Bedrooms
4,028
Square Feet
0.30
Acres

401 Heath Street, Brookline, MA 02467

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

70 Park Street, Unit 17, Brookline, MA 02446

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

85 Sears Road, Brookline, MA 02445

a front view of a house with garden

$6,850,000

4
Bedrooms
4,647
Square Feet
0.16
Acres

11 Hemlock Road, Cambridge, MA 02138

$6,675,000 | 59 High Street, Brookline, MA 02445

$6,675,000

6
Bedrooms
7,450
Square Feet
0.50
Acres

59 High Street, Brookline, MA 02445

$6,288,000 | 99 Sargent Road, Brookline, MA 02445

$6,288,000

6
Bedrooms
8,841
Square Feet
1.44
Acres

99 Sargent Road, Brookline, MA 02445

a front view of a house with porch

$6,000,008

8
Bedrooms
6,535
Square Feet
0.89
Acres

388 Warren Street, Brookline, MA 02445

$5,995,000 | 248 Buckminster Road, Brookline, MA 02445

$5,995,000

7
Bedrooms
7,722
Square Feet
0.56
Acres

248 Buckminster Road, Brookline, MA 02445

a front view of a house with a yard

$5,700,000

7
Bedrooms
5,800
Square Feet
0.54
Acres

216 Tappan Street, Brookline, MA 02445

$5,500,000 | 96 Crafts Road, Brookline, MA 02467

$5,500,000

6
Bedrooms
6,313
Square Feet
0.81
Acres

96 Crafts Road, Brookline, MA 02467

$5,250,000 | 371 Walnut Street, Brookline, MA 02445

$5,250,000

7
Bedrooms
6,193
Square Feet
0.96
Acres

371 Walnut Street, Brookline, MA 02445

$5,100,000 | 294 Buckminster Road, Brookline, MA 02445

$5,100,000

6
Bedrooms
8,475
Square Feet
0.65
Acres

294 Buckminster Road, Brookline, MA 02445

$4,825,000 | 8 Holly Road, Newton, MA 02468

$4,825,000

6
Bedrooms
8,502
Square Feet
0.77
Acres

8 Holly Road, Newton, MA 02468

$4,800,000 | 13 Cazenove Street, Boston, MA 02116

$4,800,000

5
Bedrooms
3,518
Square Feet
0.03
Acres

13 Cazenove Street, Boston, MA 02116

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

59 Cramond Road, Brookline, MA 02467

a front view of a house with a yard

$4,500,000

6
Bedrooms
5,461
Square Feet
0.52
Acres

161 Pine Ridge Road, Waban, MA 02468

$4,500,000 | 41 Codman Road, Brookline, MA 02445

$4,500,000

7
Bedrooms
6,637
Square Feet
1.00
Acres

41 Codman Road, Brookline, MA 02445

$4,500,000 | 321 Warren Street, Brookline, MA 02445

$4,500,000

7
Bedrooms
6,176
Square Feet
0.82
Acres

321 Warren Street, Brookline, MA 02445

Past Rentals
a front view of a house with garden

$9,000

5
Bedrooms

20 Metacomet Road, Newton, MA 02468

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

$3,000

3
Bedrooms

22 Ackers Avenue, Unit 1, Brookline, MA 02445