Have you ever thought about leaving the Bay Area to be closer to your kids or to stretch your retirement dollars further? In this episode, I talk with Heather Williams, a Compass agent and former registered nurse who helps retirees and downsizers in New Castle County, Delaware.
Delaware may be small, but it offers a lot. There’s no sales tax, and property taxes are generally lower than in many parts of the country. Northern Delaware sits right along I-95, with easy access to Philadelphia, Baltimore, Washington, D.C., and even New York, plus Amtrak service from Wilmington. Major employers include ChristianaCare, DuPont, and JPMorgan Chase, and the University of Delaware is based in nearby Newark.
Life there comes with four real seasons, from humid summers in the 90s to colorful falls and the occasional snowy winter. Retirees enjoy golf, parks, biking and hiking trails, tax-free shopping, and beach towns like Rehoboth, Dewey, and Bethany. There are also plenty of 55-plus communities and one-level homes for those who want to avoid stairs.
What really stood out to me was the price of homes. Heather showed us a three-bedroom ranch near Wilmington listed at $285,000, with property taxes of about $1,750 a year. A newer four-bedroom home in a 55-plus community in Middletown was priced in the $600,000s, with HOA dues of $235 a month. And at the high end, $5 million could buy an estate on more than 120 acres with equestrian facilities.
Compare that with Santa Clara County, where the median home price recently came in around $1.85 million. For Bay Area homeowners, selling here and moving to northern Delaware could open the door to more space, lower taxes, and a very different lifestyle.
If you’re thinking about relocating out of state, the right plan starts with understanding both what your home is worth here and what your money can buy there.
Does your place need a little work?
Sell As-Is. Sell for More.
No remodel, no lowball investor offer. Most Bay Area sellers net more selling as-is, and I'll show you how to get full market value without fixing a thing.
Show Me How →
From the Bay Area Wayback Machine
California Voters Defeat the Briggs Initiative (November 7, 1978)
California voters rejected Proposition 6, known as the Briggs Initiative, by a margin of 58% to 42%. Sponsored by state legislator John Briggs, the measure would have allowed public schools to fire, or refuse to hire, teachers and staff who were gay or lesbian or who supported gay rights. In San Francisco, Supervisor Harvey Milk helped lead the campaign against it, and more than 75% of the city’s voters said no. Opposition came from across the political spectrum, including former Governor Ronald Reagan. The measure’s defeat became a landmark moment in the history of LGBTQ rights.
This Week in Silicon Valley
Silicon Valley Billionaires Spend Big to Defeat Proposition 40
Some of Silicon Valley‘s wealthiest residents are pouring money into the fight against Proposition 40, a statewide ballot measure that would impose a one-time 5% tax on billionaires. Supporters say it could raise up to $100 billion over five years for health care and other social services. The tax would affect about 200 California billionaires, most of them in the Bay Area.
Google co-founder Sergey Brin has put about $103 million into the opposition campaign, and former Google CEO Eric Schmidt has contributed more than $40 million. Other major donors include venture capitalist John Doerr, Stripe CEO Patrick Collison, and Vinod Khosla. The main opposition committee had spent about $140 million by late October, compared with roughly $33 million from supporters, led by the health care workers union SEIU-UHW.
Opponents, including Gov. Gavin Newsom, argue the tax could drive billionaires out of California and ultimately reduce state revenue. Supporters say it would help offset federal health care cuts. Two related measures, Props 41 and 42, would cancel the tax if they pass with more votes than Prop 40.
Accurate Home Price Data Is Just a Click Away!
Live MLS Data
What Are Homes Actually Selling For Right Now?
Median price, days on market, and how many homes are selling over asking, pulled straight from current MLS data for your neighborhood.
See the Live Sales Data →Medicare 2027: What’s Changing & What Are Your Options?
Date: Thursday, November 5
Time: 1:00 pm – 2:00 pm
Location: Willow Glen Community and Senior Center, 2175 Lincoln Avenue, San Jose
Medicare open enrollment is here, and 2027 brings plenty of changes. Bring a friend, neighbor, or family member to this relaxed, no-pressure community meeting with a local licensed Medicare broker, where you can ask questions, compare your options, and take home information to review at your own pace.
Mastering Medicare: Turn Confusion into Confidence
Date: Thursday, November 5
Time: 6:00 pm – 7:00 pm
Location: Mountain View Public Library, 585 Franklin Street, Mountain View
Whether you’re new to Medicare, nearing eligibility, or already enrolled, this friendly, beginner-focused session will help everything make sense. Learn how the different parts of Medicare fit together, what’s changing, and how to choose coverage with confidence, all explained in plain language by a certified financial planner.
Laughter is Good Medicine Gala: Dinner & Comedy Show
Date: Friday, November 6
Time: 5:30 pm – 9:30 pm
Location: Mexican Heritage Theater, 1700 Alum Rock Avenue, San Jose
Share a delicious dinner and plenty of laughs at the Indian Health Center of Santa Clara Valley’s annual gala, held in honor of American Indian Heritage Month. The evening features a special program, community stories, and a lively comedy show, all supporting care for thousands of patients across Santa Clara County.
Media, Information & AI Literacy: Navigating Our Changing Digital World
Date: Saturday, November 7
Time: 3:00 pm – 4:00 pm
Location: Mountain View Public Library, 585 Franklin Street, Mountain View
Ever wonder whether that photo, video, or headline is real? This interactive workshop helps you build practical skills for navigating today’s digital world, from understanding how social media decides what you see to spotting convincing AI-generated content. You’ll leave feeling more confident about what to trust online.
Time to talk to a REALTOR?
Senior Friendly Homes in Silicon Valley South
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
