Chuck Gillooley Real Estate

Chuck Gillooley Real Estate I am the CEO and founder of Ektra Real Estate, a Realtor serving the Mid-Peninsula, and the author of the popular White Oaks Blog.

Set on a beautifully landscaped, nearly half-acre gated lot, this elegant 5-bedroom, 4.5-bath home offers exceptional pr...
09/09/2026

Set on a beautifully landscaped, nearly half-acre gated lot, this elegant 5-bedroom, 4.5-bath home offers exceptional privacy and space.

Inside, a private upstairs primary suite with dual walk-in closets is complemented by two additional en-suite bedrooms downstairs.

The gourmet kitchen features high-end appliances and opens to generous living spaces, including separate formal dining, living, and family rooms. Soaring ceilings and expansive windows fill the home with natural light, complemented by beautifully refinished maple hardwood floors.

Outside, mature heritage trees surround the property, creating a private setting for the in-ground pool, spa, and built-in barbecue.

A rare opportunity to enjoy space, privacy, and modern luxury in a prime Atherton location.

đź“Ť 28 HOLBROOK LANE, ATHERTON
5 Beds | 4.5 Baths | 3,765 Sq Ft
Offered at $5,888,000

OPEN HOUSES:
Sat, Sept 12 | 1–4 PM
Sun, Sept 13 | 1–4 PM
Tues, Sept 15 | 10 AM–1 PM

For more photos, videos, floor plans, a 3D tour, open house dates, and full property details, visit the property website.

www.28holbrookln.com

The Mid-Peninsula housing market rebounded strongly in August, with buyers returning ahead of the traditional start of t...
09/09/2026

The Mid-Peninsula housing market rebounded strongly in August, with buyers returning ahead of the traditional start of the fall market.

Menlo Park, San Mateo, and San Carlos were among the standouts, with all three seeing significant gains in average sales price, new listings, and closed sales.

Swipe through for a closer look at August market activity in Burlingame, San Mateo, Belmont, San Carlos, Redwood City, Menlo Park, and Palo Alto.

đź“© Have questions about what these numbers mean for your neighborhood? Reach out anytime.

Closing the 700 block of Laurel Street made a lot of sense in 2020. But six years later, is permanently closing and rede...
09/06/2026

Closing the 700 block of Laurel Street made a lot of sense in 2020. But six years later, is permanently closing and redesigning the street still the right decision for downtown San Carlos?

As the City’s plans move forward, there are legitimate questions about parking, outdoor dining, the cost of the project, and most importantly, the impact on the longtime businesses that make Laurel Street what it is.

I took a closer look at the plans, the concerns being raised by local business owners, and whether there might be a better path forward.

Whether you agree or disagree, I think it’s a conversation San Carlos needs to have.

Read the full article and share your thoughts on The White Oaks Blog:
https://www.whiteoaksblog.com/2026/08/13/is-closing-laurel-street-still-a-good-idea/

It was a wild week in the San Carlos real estate market.Eleven homes closed last week, and there were some pretty dramat...
09/02/2026

It was a wild week in the San Carlos real estate market.

Eleven homes closed last week, and there were some pretty dramatic swings in the prices buyers were willing to pay. Six of those homes sold for at least $300,000 over asking, including one that blew past its list price by more than $900,000. On the other end of the spectrum, two homes needed six-figure reductions to close.

What makes all of this even more interesting is that these homes went under contract in late July and early August, historically one of the quieter stretches of the summer market. Instead, this summer has been unusually active in San Carlos.

Seven new listings also came to market last week, which could be an early indication that we’re in for a busy fall as we head into September.

Catch up on last week’s sales, pending homes, new listings, and the latest San Carlos market activity:
https://www.whiteoaksblog.com/2026/08/31/san-carlos-real-estate-08-31-2026/

08/26/2026

Take a look inside this beautifully updated home in San Carlos’ Alder Manor neighborhood.

With 4 bedrooms and 3 full bathrooms across 2,120 sq ft, the home features a versatile floor plan with two en-suite bedrooms on separate levels, including a private primary suite upstairs. An updated chef’s kitchen, kitchen nook, formal dining, and beautifully refreshed interiors add to the home’s appeal.

Tucked away on a quiet cul-de-sac just blocks from Eaton Park, this is a rare opportunity in a sought-after San Carlos neighborhood.

đź“Ť 2872 ROLAND AVE, SAN CARLOS
Offered at $2,398,000

For more photos, videos, floor plans, a 3D tour, open house dates, and full property details, visit the property website.

www.2872rolandave.com

Tucked away on a quiet cul-de-sac in the Alder Manor neighborhood, this beautifully updated 4-bedroom, 3-bath home offer...
08/21/2026

Tucked away on a quiet cul-de-sac in the Alder Manor neighborhood, this beautifully updated 4-bedroom, 3-bath home offers a thoughtfully designed layout in a prime San Carlos location.

Inside, two of the four bedrooms are en suite, including a private upstairs primary suite. The chef’s kitchen features a gas cooktop, brand-new double oven, and plenty of counter space, with both a cozy kitchen nook and formal dining room just steps away. Restored hardwood floors, new carpet, fresh interior paint, central heat and A/C, and dual-pane windows round out the home.

Located close to schools and just a couple of blocks from the Eaton Park trailhead, the home offers convenient access to one of San Carlos’ great neighborhood hiking spots.

A rare opportunity in a sought-after San Carlos neighborhood, this home is one you won’t want to miss.

2872 Roland Avenue | San Carlos
4 Beds | 3 Baths | 2,120 Sq Ft
Offered at: $2,398,000

Open Houses:
Sat 8/22 | 1–4 PM
Sun 8/23 | 1–4 PM
Tues 8/25 | 10–1 PM

For more photos, videos, floor plans, and full property details, visit the property website:
www.2872rolandave.com

The summer slowdown may officially be coming to an end.With schools back in session and summer vacations wrapping up, th...
08/18/2026

The summer slowdown may officially be coming to an end.

With schools back in session and summer vacations wrapping up, this is typically when real estate activity begins to pick up again in San Carlos. After a quieter few weeks, we could be looking at the unofficial start of the fall market.

Catch up on last week’s sales, pending homes, new listings, and the latest San Carlos market activity.

Read the full report on the White Oaks Blog. Link in bio.

Welcome to the last installment of our San Carlos Neighborhood Spotlight series.This week, we’re taking a closer look at...
08/17/2026

Welcome to the last installment of our San Carlos Neighborhood Spotlight series.

This week, we’re taking a closer look at Alder Manor, one of San Carlos’ most overlooked neighborhoods. While much of the neighborhood falls within the Redwood City School District, Alder Manor remains one of the city’s most expensive neighborhoods thanks to its larger lots, spacious homes, and desirable hillside locations. For buyers who prioritize a San Carlos address over school boundaries, it can offer exceptional value.

In the latest report, I take a closer look at:ďż˝
• Home prices and market performance�
• Sales activity over the past five years�
• How Alder Manor compares to other San Carlos neighborhoods
• The characteristics that make this overlooked neighborhood unique

If you live in Alder Manor, what do you love most about the neighborhood? Let us know in the comments below.

For the complete neighborhood report and additional market data, visit the White Oaks Blog.
https://www.whiteoaksblog.com/2026/07/31/2026-san-carlos-neighborhood-check-in-alder-manor/

As summer vacations wind down and schools head back into session, the Peninsula real estate market is preparing to shift...
08/11/2026

As summer vacations wind down and schools head back into session, the Peninsula real estate market is preparing to shift into its fall season.

Unlike the spring, the fall market is condensed into just 2.5 months. That shorter window means the timing of a listing has to be much more precise: not too early that it gets lost in the back-to-school rush, but not too late that it’s still sitting on the market when November arrives.

If historical patterns repeat, we should see a solid surge of new listings just after Labor Day weekend. The other challenge facing sellers this fall is interest rates, which have quietly climbed back to levels we haven’t seen in more than a year.

We’re planning to get ahead of both the fall rush and rising rates with a beautiful four-bedroom home coming to market next week in San Carlos’ Alder Manor neighborhood. More details coming soon!

See the full review on the White Oaks Blog.
https://www.whiteoaksblog.com/2026/08/10/san-carlos-real-estate-08-10-2026/

July is usually one of the slower months of the real estate calendar along the Peninsula since many buyers put their sea...
08/05/2026

July is usually one of the slower months of the real estate calendar along the Peninsula since many buyers put their search on hold and take a vacation, and many sellers choose to wait until the fall to list their homes.

Despite that historical expectation, San Carlos and Menlo Park both had an impressive month for new listings, with San Carlos posting the strongest July for new listings in four years.

The average days on market for all of the communities featured increased from June, as homes that remain on the market over the summer months generally take a little longer to sell. That will improve once the buyers return from vacation and the fall market commences.

If you would like more context on what this means for your specific neighborhood, feel free to reach out.

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San Carlos, CA
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