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Robert Chestnut

Realtor® | DRE# 02157059

Specialties

Buyer's Agent, Listing Agent; Relocation, Luxury, Coastal, Probate, Trust & Estate
Client Testimonials

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★★★★★
" My wife and I met Robert in June 2023 while in a search of a new home. Robert showed us a home in a nice area of Watsonville that my wife and liked. 17 days later we owned that property. Thanks to Robert’s diligence and deep Understanding of his craft we owe him no less than 5 ⭐️⭐️⭐️⭐️⭐️’s for his hard work and honesty throughout the process. P.S. THANK YOU ROBERT "-Joseph & Andrea D., Buyers
★★★★★
" Please let this letter service as 5 Star recommendation for Robert Chestnut. We engaged Robert in October 2022 for the sale of our property after our mother had passed away the previous August. Robert immediately jumped into action guiding us as to what needed to be done to the house before putting it on the market. He is driven to do a great job for clients always focused on getting the best possible sales price. After  getting the house ready he carefully gauged the market and determined the very best time to put the house on the MLS. I am pleased to say that with a very successful open house on the very first weekend we got an amazing offer and closed in 10 days. This was absolutely due to Robert’s efforts to time the market and knowing the other houses we were competing against. In addition, Robert has very deep knowledge regarding handling offers and working with them to get the best price. It also helped that Robert has relationships with many of the local agents. I am speaking for my family when I say I would highly recommend Robert to anyone selling or purchasing a property. His pleasant personality and driven work attitude all add up to a great agent in every respect. We are incredibly pleased. "-Daniel A., Seller
★★★★★
" Robert is the real estate agent you wish you had. Robert helped us secure our dream place in December of 2022. What makes him unique is a number of traits that made this process a joy:He knows Santa Cruz inside and out, local knowledge you can rely on.He goes above and beyond. In every way. He checked countless times on the house while we were going through the negotiation process. It rained, he went there to check if and where water might have come in. There were questions about permits, he went to the city to meet with the associates there to get more insight. He organized various contractor visits to get assessments and quotes for work that needs to be done, from contractors he trusts – and multiple sources on top of that. And he was there to meet with them. He just managed all that for us.He was a great partner in the negotiations with the seller which weren’t easy, to say the least, but we ended up getting our dream place for a fair price.Best of all: once the deal was signed, he didn’t consider his job to be done. He is still there to this day helping us get started and getting the place ready which includes that we have all the quotes and contacts for contractors to get the work needed done thanks to his organizing this earlier.I can wholeheartedly recommend Robert to anyone looking to buy a property in the Santa Cruz or Monterey Counties."-Jan K., Buyer
★★★★★
" Robert is very nice."Jim T., Buyer

About Robert

Robert Chestnut is a luxury coastal real estate professional serving the Monterey Bay, Carmel, and Santa Cruz markets. Licensed since 2021, he represents notable coastal and estate properties throughout Santa Cruz County and the greater Central Coast. With family roots on the Monterey Bay spanning five generations, Robert offers clients a deep, authentic understanding of the communities he serves.

Before entering real estate, Robert built a distinguished career in film and television, appearing in national commercial campaigns for leading Fortune 500 brands including Pepsi, Coca‑Cola, Ford, McDonald’s, Anheuser‑Busch, and IBM. His work earned multiple industry recognitions for performance and professionalism. In real estate, Robert is a recipient of the Presidents Club Award, reflecting his commitment to client service and consistent results. He also serves as President of SAG‑AFTRA San Francisco–Northern California, underscoring his leadership, advocacy, and ethical approach.

Robert’s background extends into motorsports, where he has supported professional sportscar racing, NHRA Drag Racing, NASCAR, and youth programs. He founded multiple apparel and lifestyle brands — including a motorsports‑focused female empowerment line — and has sponsored groundbreaking all‑girls racing teams, including the first National Jr. Drag Racing Team and National BMX all‑girls team. Laguna Seca Raceway remains his home track and a central part of his connection to the sport.

Clients appreciate Robert’s strategic approach, polished communication, and calm execution. Fellow agents value his reliability, leadership, and respect for the collaborative nature of real estate.

Robert Chestnut’s Transactions

Past Sales
a front view of a house with garden

$2,828,000

4
Bedrooms
2,893
Square Feet
0.18
Acres
$2,200,000 | 24735 Dolores Street, Carmel, CA 93923

$2,200,000

2
Bedrooms
1,396
Square Feet
0.09
Acres
front view of a house

$1,740,000

2
Bedrooms
1,490
Square Feet
0.09
Acres
$1,740,000 | 0 Southeast 4th Avenue, Carmel, CA 93923

$1,740,000

2
Bedrooms
1,490
Square Feet
0.09
Acres
a front view of a house with a yard and potted plants

$1,550,000

3
Bedrooms
1,572
Square Feet
0.22
Acres
a front view of a house with a yard

$1,408,000

3
Bedrooms
1,701
Square Feet
1.86
Acres
a front view of a house with a garden

$1,330,000

4
Bedrooms
2,037
Square Feet
0.09
Acres
$1,265,000 | 3035 Andesite Drive, Marina, CA 93933

$1,265,000

3
Bedrooms
2,403
Square Feet
0.15
Acres
a front view of a house with a yard and garage

$1,240,000

5
Bedrooms
3,818
Square Feet
0.50
Acres
a front view of a house with a yard and garage

$689,000

3
Bedrooms
1,345
Square Feet
0.11
Acres
$452,000 | 14410 Big Canyon Road, Middletown, CA 95461

$452,000

4
Bedrooms
1,900
Square Feet
160
Acres
front view of a house with a yard

$325,000

3
Bedrooms
1,396
Square Feet
0.18
Acres