Ann (Ruby) Conrad, Realtor/Owner
CONRAD Development
ruby@conraddevelopment.com
608.770.0212
Ruby Conrad’s perspective on housing- in terms of scale, affordability, and carbon footprint- is informed by extensive world travel and living in several major cities.
After graduating from UW-Madison in 1999, living in the Lakeshore dorms and Rochdale Coop, Ruby’s pursuit of a TV writing career took her to San Francisco, Los Angeles, New York City, and Mumbai, India. Her Emmy Award winning shows include “Ruby’s Studio” (Amazon Prime) and “Growing Up Creepie” (Discovery Kids).
During those years, she lived in a 420 square foot Artist Loft in Marin County, followed by a low income studio apartment for creatives in a Downtown Los Angeles apartment building, a women’s housing project in Chelsea followed by a 214 square foot coop studio pied a terre in the East Village.
Returning home to Wisconsin in 2008, Ruby designed a 232 square foot tiny home which she built (with the help of Amish builders) and lived in for two years on her family’s land in Riley.
Ruby entered the Madison Real Estate scene in 2013 after buying her own home in the Bay Creek Neighborhood as a single, self-employed woman, writing and attending women in childbirth as a doula. Her doula clients eventually needed bigger houses, and with their trust of Ruby and support through a major life event, many of them choose her as their Realtor. Sometimes called ‘the house doula’ Ruby uses her skills of advocacy, deep listening, and guidance to come alongside her clients’ dreams and visions to buy, sell, or build.
Ruby sees the demand, low inventory and extremely competitive market for first-time home buyers, down-sizers, and retirees in the Madison area as a call to create solutions. She acknowledges the systemic racism that makes homeownership more challenging for people of color and the advantage that many white buyers have due to family inheritance or financial gifting. Fluent in Spanish, and the former lower-school Spanish teacher at Madison Country Day School (MCDS), Ruby is helping the La Jornada effort at the National Youth Advocacy Program (NYAP) with their Transitional Foster Care program for unaccompanied children and youth from around the world . She also enjoys kayaking on area lakes and rivers, and is a member of the Clean Lakes Alliance. Ruby joined the Board of Directors of Madison Ballet in the Fall of 2025, and is a cast member of The Nutcracker with her husband Chris and daughter Naomi.