Today we’d like to introduce you to Madeline Yankee

Hi Madeline, we’re thrilled to have a chance to learn your story today. So, before we get into specifics, maybe you can briefly walk us through how you got to where you are today?

I originally went to school to become a geologist, but life had other plans. My mother, Cynthia, a realtor in Sonoma Valley, saw the potential in vacation rentals and founded Woodfield Properties, the first vacation rental company in the area. As the vacation rental industry grew, so did our business, with my mom’s real estate referrals complementing our growth.

In 2013, my parents needed assistance with the company, and I decided to change my career path and help them out. This decision turned out to be a blessing for our family. My husband, who suffered a back injury and could no longer work in his trade, joined me after obtaining his real estate and broker’s licenses. Together, we transformed a small family operation into a thriving business.

Initially, it was just me running everything, but now we have multiple full-time employees and have expanded our services across Sonoma County. This business has been a labor of love, supported by a dedicated team of strong, independent women and my husband, our acting broker. Our journey has been exciting and full of potential for growth.

I’m sure it wasn’t obstacle-free, but would you say the journey has been fairly smooth so far?

We’ve faced our share of challenges, but each one has been an opportunity for growth and resilience. The COVID-19 pandemic and wildfires were significant obstacles, but we adapted and focused on supporting our community. Personally, my son’s bone marrow transplant and my mom’s battle with dementia were tough, but our team’s support and resilience saw us through. Despite these personal hardships, we’ve always prioritized our families and health, which has strengthened our bond and commitment to our work.

Great, so let’s talk business. Can you tell our readers more about what you do and what you think sets you apart from others?

Woodfield Properties is a family-run business with deep roots in the Sonoma Valley community. We offer a range of vacation rentals, from cozy cottages to luxurious estates, all managed with a personal touch and a commitment to kindness. We treat our guests, property owners, and neighbors like family, always ensuring everyone feels welcome and cared for.

This is the community where I was raised and where I am raising my kids, so I want the best future for everyone here. We support local businesses and promote responsible tourism, helping our guests experience the true spirit of Sonoma Valley while respecting our neighbors and environment. Our team, including my husband and I, work closely with local contractors to maintain high standards for our properties.

We strive to manage our properties in a way that integrates seamlessly with the community, ensuring a harmonious relationship between our guests and local residents. We blend our community roots with modern practices to provide an exceptional experience for our guests, always with a focus on kindness, human touch, and genuine care. This approach keeps us a beloved part of the Sonoma Valley community.

What quality or characteristic do you feel is most important to your success?

The most important quality to our success has been adaptability. My mother, Cynthia, founded Woodfield Properties with a pioneering spirit, and when I took over, I introduced modern technology to help the business evolve with the times. This blend of entrepreneurial drive and innovation has allowed us to grow and thrive.

Our adaptability means we can navigate industry changes and challenges while maintaining our commitment to personalized service and community values. This flexibility, combined with our genuine care for our guests, property owners, and neighbors, has been key to our success. We treat everyone like family, ensuring they feel welcome and valued, which has built strong, lasting relationships and trust.

Contact Info:

• Website: https://www.woodfieldproperties.com/
• Instagram: https://www.instagram.com/winecountryrentals/
• Facebook: https://www.facebook.com/woodfieldproperties/

Image Credits

707 Photography, SeaTimber Media, Rachael Hairston Photography