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2025: REAL Trends ā€˜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 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
$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 CompassUnder Agreement

$4,995,000

7
Bedrooms
6,560
Square Feet
0.72
Acres
$4,650,000 | 50 Sumner Road, Brookline, MA 02445
$4,650,000 | 50 Sumner Road, Brookline, MA 02445
$4,650,000 | 50 Sumner Road, Brookline, MA 02445
$4,650,000 | 50 Sumner Road, Brookline, MA 02445
$4,650,000 | 50 Sumner Road, Brookline, MA 02445
$4,650,000 | 50 Sumner Road, Brookline, MA 02445
$4,650,000 | 50 Sumner Road, Brookline, MA 02445
$4,650,000 | 50 Sumner Road, Brookline, MA 02445
$4,650,000 | 50 Sumner Road, Brookline, MA 02445
$4,650,000 | 50 Sumner Road, Brookline, MA 02445
$4,650,000 | 50 Sumner Road, Brookline, MA 02445
$4,650,000 | 50 Sumner Road, Brookline, MA 02445
$4,650,000 | 50 Sumner Road, Brookline, MA 02445
$4,650,000 | 50 Sumner Road, Brookline, MA 02445
$4,650,000 | 50 Sumner Road, Brookline, MA 02445
$4,650,000 | 50 Sumner Road, Brookline, MA 02445
$4,650,000 | 50 Sumner Road, Brookline, MA 02445
$4,650,000 | 50 Sumner Road, Brookline, MA 02445
$4,650,000 | 50 Sumner Road, Brookline, MA 02445
$4,650,000 | 50 Sumner Road, Brookline, MA 02445
$4,650,000 | 50 Sumner Road, Brookline, MA 02445
$4,650,000 | 50 Sumner Road, Brookline, MA 02445
$4,650,000 | 50 Sumner Road, Brookline, MA 02445
$4,650,000 | 50 Sumner Road, Brookline, MA 02445
$4,650,000 | 50 Sumner Road, Brookline, MA 02445
$4,650,000 | 50 Sumner Road, Brookline, MA 02445
$4,650,000 | 50 Sumner Road, Brookline, MA 02445
$4,650,000 | 50 Sumner Road, Brookline, MA 02445
$4,650,000 | 50 Sumner Road, Brookline, MA 02445
$4,650,000 | 50 Sumner Road, Brookline, MA 02445
$4,650,000 | 50 Sumner Road, Brookline, MA 02445
$4,650,000 | 50 Sumner Road, Brookline, MA 02445
1/32
Listed By Compass

$4,650,000

5
Bedrooms
5,423
Square Feet
0.41
Acres
$4,250,000 | 540 Chestnut Hill Avenue, Brookline, MA 02445
$4,250,000 | 540 Chestnut Hill Avenue, Brookline, MA 02445
$4,250,000 | 540 Chestnut Hill Avenue, Brookline, MA 02445
$4,250,000 | 540 Chestnut Hill Avenue, Brookline, MA 02445
$4,250,000 | 540 Chestnut Hill Avenue, Brookline, MA 02445
$4,250,000 | 540 Chestnut Hill Avenue, Brookline, MA 02445
$4,250,000 | 540 Chestnut Hill Avenue, Brookline, MA 02445
$4,250,000 | 540 Chestnut Hill Avenue, Brookline, MA 02445
$4,250,000 | 540 Chestnut Hill Avenue, Brookline, MA 02445
$4,250,000 | 540 Chestnut Hill Avenue, Brookline, MA 02445
$4,250,000 | 540 Chestnut Hill Avenue, Brookline, MA 02445
$4,250,000 | 540 Chestnut Hill Avenue, Brookline, MA 02445
$4,250,000 | 540 Chestnut Hill Avenue, Brookline, MA 02445
$4,250,000 | 540 Chestnut Hill Avenue, Brookline, MA 02445
$4,250,000 | 540 Chestnut Hill Avenue, Brookline, MA 02445
$4,250,000 | 540 Chestnut Hill Avenue, Brookline, MA 02445
$4,250,000 | 540 Chestnut Hill Avenue, Brookline, MA 02445
$4,250,000 | 540 Chestnut Hill Avenue, Brookline, MA 02445
1/18
Listed By Compass

$4,250,000

5
Bedrooms
6,419
Square Feet
1.03
Acres
$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 Compass

$3,295,000

5
Bedrooms
2,834
Square Feet
0.92
Acres
$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 CompassUnder Agreement

$3,200,000

5
Bedrooms
3,680
Square Feet
0.36
Acres
$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 CompassUnder Agreement

$3,200,000

5
Bedrooms
3,680
Square Feet
$2,765,000 | 401 Heath Street, Brookline, MA 02467
$2,765,000 | 401 Heath Street, Brookline, MA 02467
$2,765,000 | 401 Heath Street, Brookline, MA 02467
$2,765,000 | 401 Heath Street, Brookline, MA 02467
$2,765,000 | 401 Heath Street, Brookline, MA 02467
$2,765,000 | 401 Heath Street, Brookline, MA 02467
$2,765,000 | 401 Heath Street, Brookline, MA 02467
$2,765,000 | 401 Heath Street, Brookline, MA 02467
$2,765,000 | 401 Heath Street, Brookline, MA 02467
$2,765,000 | 401 Heath Street, Brookline, MA 02467
$2,765,000 | 401 Heath Street, Brookline, MA 02467
$2,765,000 | 401 Heath Street, Brookline, MA 02467
$2,765,000 | 401 Heath Street, Brookline, MA 02467
$2,765,000 | 401 Heath Street, Brookline, MA 02467
$2,765,000 | 401 Heath Street, Brookline, MA 02467
$2,765,000 | 401 Heath Street, Brookline, MA 02467
$2,765,000 | 401 Heath Street, Brookline, MA 02467
$2,765,000 | 401 Heath Street, Brookline, MA 02467
$2,765,000 | 401 Heath Street, Brookline, MA 02467
$2,765,000 | 401 Heath Street, Brookline, MA 02467
$2,765,000 | 401 Heath Street, Brookline, MA 02467
$2,765,000 | 401 Heath Street, Brookline, MA 02467
$2,765,000 | 401 Heath Street, Brookline, MA 02467
$2,765,000 | 401 Heath Street, Brookline, MA 02467
$2,765,000 | 401 Heath Street, Brookline, MA 02467
$2,765,000 | 401 Heath Street, Brookline, MA 02467
$2,765,000 | 401 Heath Street, Brookline, MA 02467
1/27
Listed By Compass

$2,765,000

5
Bedrooms
4,028
Square Feet
0.30
Acres

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

$5,500,000

6
Bedrooms
6,313
Square Feet
0.81
Acres
$5,250,000 | 371 Walnut Street, Brookline, MA 02445

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

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

$4,500,000

7
Bedrooms
6,176
Square Feet
0.82
Acres
a front view of a house with a yard

$4,500,000

6
Bedrooms
5,461
Square Feet
0.52
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