Hilary Maddox Team's profile photo

Hilary Maddox Team

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 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
a front view of a house with a yard
a living room with furniture and a fireplace
a kitchen with stainless steel appliances kitchen island granite countertop a table chairs sink and cabinets
a large white kitchen with stainless steel appliances kitchen island granite countertop a sink and cabinets
a view of a kitchen with dining table and chairs
a living room with furniture and a couch
a living room with furniture and a large window
a view of a dining room with furniture window and wooden floor
a view of a dining room with furniture window and wooden floor
a living room with furniture and a fireplace
a bedroom with furniture and a large window
a view of entryway and hall with wooden floor
a bedroom with a bed and a window
a white bath tub sitting next to a bathroom
a bedroom with a bed and a dresser
a living room with furniture and a flat screen tv
a bathroom with a sink and a mirror
a bathroom with a sink a vanity and a bathtub
a view of entryway with a front door
a bedroom with a bed and a flat screen tv
a living room with furniture and window
a bathroom with a double vanity sink mirror and shower
a view of an entryway with workspace
a living room with furniture and a flat screen tv
a view of a building with a yard and sitting area
a view of a patio with table and chairs and potted plants
a view of a swimming pool with a patio
1/27
Listed By Compass

$4,895,000

6
Bedrooms
7,667
Square Feet
0.39
Acres
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
$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: 5/2 12:00PM - 01:00PM

$3,495,000

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 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
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
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