Hilary Maddox Team's profile photo

Hilary Maddox Team

hilarymaddoxteam@compass.com
M: 617-646-9003

Awards

2025: REAL Trends ‘America’s Best’ Real Estate Professionals List
About Hilary Maddox Team
Both 20+ year residents of Brookline, we specialize in advising clients from first-time buyers to seasoned sellers, primarily in Brookline and Newton markets. With Hilary’s background in investment banking and venture capital and Taylor's background in marketing and brand strategy, we offer our clients a specialized market perspective, strong negotiating skills, and a tireless work ethic (plus, we have a lot of fun in the process!). Additionally, with an eye for design and passion for restoration and renovation, we are a full-service team that helps our clients envision the possibilities of a home and connect them with the area’s leading providers.

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.

About Taylor


Born and raised in Brookline’s Fisher Hill, Taylor is a 20+ year resident of Brookline. Before transitioning into real estate, Taylor spent 10 years working at top marketing firms in Boston and New York City consulting for Fortune 100 brands.

Growing up in a family business of high-end decorative carpets, Taylor was constantly exposed to residential architecture and interior design at an early age, which developed her penchant for renovation and design, which she credits for ultimately leading her into real estate.

Through her experiences working in marketing and a family business, Taylor understands the importance of having a strong pulse on the market, its competition and trends, and brings a well-rounded business approach and specialized market perspective to buying and selling real estate. Taylor takes pride in urgency and the quality of her work as well as building long-term, trusted partnerships with her clients.

Taylor currently lives in Brookline with her husband and son.

Team Agents

Hilary Maddox Team’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 and a large window
a living room with furniture a fireplace and a flat screen tv
a living room with fireplace furniture and a large window
a living room with furniture fireplace and a flat screen tv
a bedroom with a bed and a fireplace
a view of a dining room with furniture window and wooden floor
a view of a living room with furniture and window
a dining room with furniture and wooden floor
a kitchen with granite countertop a refrigerator and a sink
a dining room with furniture window and outside view
a living room with furniture and a window
a living room with furniture and a window
a living room with furniture and a window
a living room with furniture a rug and a chandelier
a spacious bedroom with a large bed and a fireplace
a bathroom with a sink and a mirror
a living room with furniture 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 windows
a bathroom with a sink and a bathtub
a bedroom with a bed and wooden floor
a bedroom with a bed and a window
a living room with furniture and a large window
a room with pool table and flat screen tv
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 swimming pool with a table and chairs
a view of a patio with couches and potted plants
a view of a back yard
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
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

front view of a house with a street
a front view of a house with a yard
a living room with furniture and a fireplace
a living room with furniture fireplace and large windows
a dining room with wooden floor and furniture
a living room with furniture
a living room with furniture and a fireplace
a view of a dining room with furniture and a large window
a kitchen with stainless steel appliances granite countertop a stove and a sink
a large white kitchen with lots of counter top space
a living room with furniture and a large window
a bedroom with a bed chair and window
a view of a table and chairs in the garden
a yard with table and a chairs
an aerial view of a house
front view of a house with a yard
a front view of a house with a garden
a view of a house with a garden
1/18
Listed By Compass

$4,250,000

5
Bedrooms
6,419
Square Feet
1.03
Acres

540 Chestnut Hill Avenue, Brookline, MA 02445

$3,495,000 | 185 Warren Street, Brookline, MA 02445
$3,495,000 | 185 Warren Street, Brookline, MA 02445
$3,495,000 | 185 Warren Street, Brookline, MA 02445
$3,495,000 | 185 Warren Street, Brookline, MA 02445
$3,495,000 | 185 Warren Street, Brookline, MA 02445
$3,495,000 | 185 Warren Street, Brookline, MA 02445
$3,495,000 | 185 Warren Street, Brookline, MA 02445
$3,495,000 | 185 Warren Street, Brookline, MA 02445
$3,495,000 | 185 Warren Street, Brookline, MA 02445
$3,495,000 | 185 Warren Street, Brookline, MA 02445
$3,495,000 | 185 Warren Street, Brookline, MA 02445
$3,495,000 | 185 Warren Street, Brookline, MA 02445
$3,495,000 | 185 Warren Street, Brookline, MA 02445
$3,495,000 | 185 Warren Street, Brookline, MA 02445
$3,495,000 | 185 Warren Street, Brookline, MA 02445
$3,495,000 | 185 Warren Street, Brookline, MA 02445
$3,495,000 | 185 Warren Street, Brookline, MA 02445
$3,495,000 | 185 Warren Street, Brookline, MA 02445
$3,495,000 | 185 Warren Street, Brookline, MA 02445
$3,495,000 | 185 Warren Street, Brookline, MA 02445
$3,495,000 | 185 Warren Street, Brookline, MA 02445
$3,495,000 | 185 Warren Street, Brookline, MA 02445
$3,495,000 | 185 Warren Street, Brookline, MA 02445
$3,495,000 | 185 Warren Street, Brookline, MA 02445
$3,495,000 | 185 Warren Street, Brookline, MA 02445
1/25
Listed By CompassOpen: 5/23 01:00PM - 02:00PM

$3,495,000

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 Compass

$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 Compass

$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: 5/23 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 Team’s Transactions

Past Sales
Photo of Home

$10,375,000

255 Dudley

Brookline

$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

a front view of a house with a yard table and chairs

$5,500,000

6
Bedrooms
6,313
Square Feet
0.81
Acres

96 Crafts Road, Brookline, MA 02467

a front view of a house with a yard and garage

$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

a front view of a house with a yard

$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 | 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