Headway Group's Profile Photo

Headway Group

headwaygroup@compass.com
M: 617-538-2239

Revenue

$100,000,000 + In Lifetime Sales Volume

Awards

2025: REAL Trends ‘America’s Best’ Real Estate Professionals List

Specialties

Development: Experience in deal sourcing, design and floor-plan support, pre-marketing 
Relocation - Specializing in full-service relocation for corporate transfers, Member of the Porchlight Preferred Partner Network 
First-Time-buyers
About Headway Group
Headway Group:

Making Headway requires a combination of patience, persistence, and adaptability. It's not always a smooth journey purchasing or selling a home, but with determination and a willingness to adjust course, we can navigate any Real Estate obstacle together.M

Meet the Founder:

Oliver is the founder and Team Lead of Headway Group and has been immersed in Real Estate for 12+ years, having worn many hats in that time from property management to brokerage and development. With a deep understanding of the construction process and as an architecture and interior design enthusiast Oliver is in a unique position to add value for developers. This "behind the walls" knowledge also lends itself well to working with non-builder sellers and buyers as it allows Oliver to help convey critical knowledge about home condition, renovation potential, and costs associated. Oliver loves to educate, and has a soft spot in his heart for ambitious first-time buyers.

When not on a project site or exploring a new neighborhood with clients, Oliver is likely by the water – an avid boater, he maintaining a slip in Charlestown and counts down the days till the season starts. He loves to cook and will often overlap those late-night client calls with an elaborate meal or a grill session on his headset. A graduate of Boston University's Questrom School of Business, fluent in both English and German, his native language. Oliver and his family reside in Cambridge.

Oliver is licensed to practice in Massachusetts. He is a member of the National Association of Realtors, Massachusetts Association of Realtors and the Greater Boston Association of Realtors.

Reach out - you wont regret it!

Team Agents

Headway Group’s Listings

$645,000 | 10 Alden Street, Ludlow, MA 01056
$645,000 | 10 Alden Street, Ludlow, MA 01056
$645,000 | 10 Alden Street, Ludlow, MA 01056
$645,000 | 10 Alden Street, Ludlow, MA 01056
$645,000 | 10 Alden Street, Ludlow, MA 01056
$645,000 | 10 Alden Street, Ludlow, MA 01056
$645,000 | 10 Alden Street, Ludlow, MA 01056
$645,000 | 10 Alden Street, Ludlow, MA 01056
$645,000 | 10 Alden Street, Ludlow, MA 01056
$645,000 | 10 Alden Street, Ludlow, MA 01056
$645,000 | 10 Alden Street, Ludlow, MA 01056
$645,000 | 10 Alden Street, Ludlow, MA 01056
$645,000 | 10 Alden Street, Ludlow, MA 01056
$645,000 | 10 Alden Street, Ludlow, MA 01056
$645,000 | 10 Alden Street, Ludlow, MA 01056
$645,000 | 10 Alden Street, Ludlow, MA 01056
$645,000 | 10 Alden Street, Ludlow, MA 01056
$645,000 | 10 Alden Street, Ludlow, MA 01056
$645,000 | 10 Alden Street, Ludlow, MA 01056
$645,000 | 10 Alden Street, Ludlow, MA 01056
$645,000 | 10 Alden Street, Ludlow, MA 01056
$645,000 | 10 Alden Street, Ludlow, MA 01056
$645,000 | 10 Alden Street, Ludlow, MA 01056
$645,000 | 10 Alden Street, Ludlow, MA 01056
$645,000 | 10 Alden Street, Ludlow, MA 01056
$645,000 | 10 Alden Street, Ludlow, MA 01056
$645,000 | 10 Alden Street, Ludlow, MA 01056
$645,000 | 10 Alden Street, Ludlow, MA 01056
$645,000 | 10 Alden Street, Ludlow, MA 01056
$645,000 | 10 Alden Street, Ludlow, MA 01056
$645,000 | 10 Alden Street, Ludlow, MA 01056
$645,000 | 10 Alden Street, Ludlow, MA 01056
$645,000 | 10 Alden Street, Ludlow, MA 01056
$645,000 | 10 Alden Street, Ludlow, MA 01056
$645,000 | 10 Alden Street, Ludlow, MA 01056
$645,000 | 10 Alden Street, Ludlow, MA 01056
$645,000 | 10 Alden Street, Ludlow, MA 01056
$645,000 | 10 Alden Street, Ludlow, MA 01056
$645,000 | 10 Alden Street, Ludlow, MA 01056
$645,000 | 10 Alden Street, Ludlow, MA 01056
$645,000 | 10 Alden Street, Ludlow, MA 01056
1/41
Listed By CompassUnder Agreement

$645,000

3
Bedrooms
2,607
Square Feet
1.01
Acres

10 Alden Street, Ludlow, MA 01056

$595,000 | 9 Medford Street, Unit 405, Somerville, MA 02143
$595,000 | 9 Medford Street, Unit 405, Somerville, MA 02143
$595,000 | 9 Medford Street, Unit 405, Somerville, MA 02143
$595,000 | 9 Medford Street, Unit 405, Somerville, MA 02143
$595,000 | 9 Medford Street, Unit 405, Somerville, MA 02143
$595,000 | 9 Medford Street, Unit 405, Somerville, MA 02143
$595,000 | 9 Medford Street, Unit 405, Somerville, MA 02143
$595,000 | 9 Medford Street, Unit 405, Somerville, MA 02143
$595,000 | 9 Medford Street, Unit 405, Somerville, MA 02143
$595,000 | 9 Medford Street, Unit 405, Somerville, MA 02143
$595,000 | 9 Medford Street, Unit 405, Somerville, MA 02143
$595,000 | 9 Medford Street, Unit 405, Somerville, MA 02143
$595,000 | 9 Medford Street, Unit 405, Somerville, MA 02143
$595,000 | 9 Medford Street, Unit 405, Somerville, MA 02143
$595,000 | 9 Medford Street, Unit 405, Somerville, MA 02143
$595,000 | 9 Medford Street, Unit 405, Somerville, MA 02143
$595,000 | 9 Medford Street, Unit 405, Somerville, MA 02143
$595,000 | 9 Medford Street, Unit 405, Somerville, MA 02143
$595,000 | 9 Medford Street, Unit 405, Somerville, MA 02143
$595,000 | 9 Medford Street, Unit 405, Somerville, MA 02143
$595,000 | 9 Medford Street, Unit 405, Somerville, MA 02143
$595,000 | 9 Medford Street, Unit 405, Somerville, MA 02143
$595,000 | 9 Medford Street, Unit 405, Somerville, MA 02143
$595,000 | 9 Medford Street, Unit 405, Somerville, MA 02143
$595,000 | 9 Medford Street, Unit 405, Somerville, MA 02143
$595,000 | 9 Medford Street, Unit 405, Somerville, MA 02143
$595,000 | 9 Medford Street, Unit 405, Somerville, MA 02143
$595,000 | 9 Medford Street, Unit 405, Somerville, MA 02143
$595,000 | 9 Medford Street, Unit 405, Somerville, MA 02143
$595,000 | 9 Medford Street, Unit 405, Somerville, MA 02143
$595,000 | 9 Medford Street, Unit 405, Somerville, MA 02143
$595,000 | 9 Medford Street, Unit 405, Somerville, MA 02143
$595,000 | 9 Medford Street, Unit 405, Somerville, MA 02143
$595,000 | 9 Medford Street, Unit 405, Somerville, MA 02143
1/34
Listed By CompassOpen: 4/4 11:00AM - 01:00PM

$595,000

1
Bedrooms
656
Square Feet

9 Medford Street, Unit 405, Somerville, MA 02143

Headway Group’s Transactions

Past Sales
$2,425,000 | 254 Commonwealth Avenue, Unit 4, Boston, MA 02116

$2,425,000

2
Bedrooms
1,471
Square Feet

254 Commonwealth Avenue, Unit 4, Boston, MA 02116

$1,740,000 | 24 Marlborough Street, Unit 2, Boston, MA 02116

$1,740,000

3
Bedrooms
1,338
Square Feet

24 Marlborough Street, Unit 2, Boston, MA 02116

$1,617,500 | 24 Old Barn Road, Hanover, MA 02339

$1,617,500

6
Bedrooms
9,612
Square Feet
3.33
Acres

24 Old Barn Road, Hanover, MA 02339

$1,550,000 | 11 Edge Hill Street, Boston, MA 02130

$1,550,000

4
Bedrooms
2,415
Square Feet
0.06
Acres

11 Edge Hill Street, Boston, MA 02130

$1,450,000 | 35 Kingston Street, Unit 3, Boston, MA 02111

$1,450,000

2
Bedrooms
1,803
Square Feet

35 Kingston Street, Unit 3, Boston, MA 02111

$1,435,000 | 16 Parkside Drive, Boston, MA 02130

$1,435,000

4
Bedrooms
2,624
Square Feet
0.23
Acres

16 Parkside Drive, Boston, MA 02130

$1,200,000 | 25 Everett Street, Unit 6, Boston, MA 02128

$1,200,000

2
Bedrooms
1,862
Square Feet

25 Everett Street, Unit 6, Boston, MA 02128

a front view of a house with a yard

$1,150,000

4
Bedrooms
4,500
Square Feet
1.04
Acres

45 Glen Road, Hopkinton, MA 01748

$1,149,000 | 24 Marlborough Street, Unit 2, Boston, MA 02116

$1,149,000

2
Bedrooms
1,338
Square Feet

24 Marlborough Street, Unit 2, Boston, MA 02116

$1,100,000 | 15 Forest Street, Medfield, MA 02052

$1,100,000

4
Bedrooms
2,648
Square Feet
1.33
Acres

15 Forest Street, Medfield, MA 02052

a front view of a house with garden

$1,100,000

3
Bedrooms
1,414
Square Feet
0.12
Acres

5 Cutting Street, Winchester, MA 01890

$1,090,000 | 8 Robeson Street, Unit 1, Boston, MA 02130

$1,090,000

3
Bedrooms
2,021
Square Feet

8 Robeson Street, Unit 1, Boston, MA 02130

$1,050,000 | 1442 Washington Street, Canton, MA 02021

$1,050,000

4
Bedrooms
3,544
Square Feet
0.65
Acres

1442 Washington Street, Canton, MA 02021

a front view of a house with a yard

$1,050,000

3
Bedrooms
2,221
Square Feet
0.39
Acres

142 Pinecrest Beach Drive, Falmouth, MA 02536

a view of a car parked in front of a house

$1,040,000

0.06
Acres

226 Havre Street, Boston, MA 02128

a front view of a house with a yard

$980,000

5
Bedrooms
2,606
Square Feet
0.10
Acres

18 Alpha Road, Boston, MA 02124

$960,000 | 14 Dana Street, Somerville, MA 02145

$960,000

6
Bedrooms
2,381
Square Feet
0.08
Acres

14 Dana Street, Somerville, MA 02145

$935,000 | 1088 Saratoga St | Boston

$935,000

7
Bedrooms

1088 Saratoga St

Boston

Past Rentals
$8,125 | 24 Marlborough Street, Unit 2, Boston, MA 02116

$8,125

3
Bedrooms

24 Marlborough Street, Unit 2, Boston, MA 02116

$6,950 | 158 Shaw Road, Brookline, MA 02467

$6,950

4
Bedrooms

158 Shaw Road, Brookline, MA 02467

a view of a white house with a big yard and potted plants

$5,300

5
Bedrooms

178 Willow Street, Stoughton, MA 02072

a view of a house with a yard

$4,800

3
Bedrooms

30 White Sisters Way, Canton, MA 02021

a living room with furniture and a large window

$4,600

2
Bedrooms

340 West 2nd Street, Unit PH23, Boston, MA 02127

a kitchen with stainless steel appliances granite countertop a stove a sink dishwasher a dining table and chairs with wooden floor

$4,350

3
Bedrooms

334 Mystic Street, Unit 334, Arlington, MA 02474

$4,200 | 40 Everett Street, Unit 40, Boston, MA 02128

$4,200

3
Bedrooms

40 Everett Street, Unit 40, Boston, MA 02128

a dining room with furniture and wooden floor

$3,950

2
Bedrooms

109 Rockview Street, Unit 3, Boston, MA 02130

$3,900 | 16-22 Reedsdale Street, Unit 18, Boston, MA 02134

$3,900

4
Bedrooms

16-22 Reedsdale Street, Unit 18, Boston, MA 02134

$3,800 | 150 West Broadway, Unit 205, Boston, MA 02127

$3,800

2
Bedrooms

150 West Broadway, Unit 205, Boston, MA 02127

a kitchen with granite countertop a refrigerator stove top oven and sink

$3,800

2
Bedrooms

76 Seaverns Avenue, Unit 76, Boston, MA 02130

a living room with furniture and a flat screen tv

$3,600

2
Bedrooms

11 South Mason Street, Unit 10, Salem, MA 01970

$3,542 | 89 E Dedham, Unit 928 | Greater Boston

$3,542

89 E Dedham, Unit 928

Greater Boston

$3,500 | 100 Shawmut Avenue, Unit 612, Boston, MA 02118

$3,500

1
Bedrooms

100 Shawmut Avenue, Unit 612, Boston, MA 02118

a view of front door

$3,500

2
Bedrooms

712-1/2 East 5th Street, Unit 2, Boston, MA 02127

$3,400 | 1060 Beacon Street, Unit 5, Brookline, MA 02446

$3,400

2
Bedrooms

1060 Beacon Street, Unit 5, Brookline, MA 02446

$3,277 | 250 N 1st St, Unit 514 | Burbank

$3,277

2
Bedrooms

250 N 1st St, Unit 514

Burbank

a kitchen with stainless steel appliances granite countertop a stove a sink dishwasher and microwave with wooden cabinets

$3,275

2
Bedrooms

232 Gold Street, Unit 2, Boston, MA 02127