This is a story about downsizing in San Diego County the hard way round — selling first, before buying — and how one negotiated term meant our client never had to move twice.
From Avocado Grove to Shadowridge Cottage
A wonderful lady reached out to us, asking if we could help her purchase a home in Ocean Hills Country Club—a community we know intimately. To make her next purchase, she also needed to sell her large property, which had once been an avocado grove.
That is a familiar shape for anyone leaving a large property behind. The acreage, the maintenance, and the upkeep that made sense for decades stop making sense, and a smaller single-story home starts to look like freedom rather than a compromise.
Overcoming Past Challenges
It quickly became clear that she had experienced some absolutely horrible situations in buying and selling real estate before. This history made her understandably reluctant to venture into the process again. We assured her that we would do everything in our power to change her perspective and help her feel good about working with real estate professionals once more.
Selling Her Home: A Twist of Fate
We got to work putting her home on the market and soon received several offers. She wanted the sale made contingent on finding somewhere to move to, and her first buyer agreed to give her that time.
Then the COVID-19 lockdown arrived and inventory vanished. As she put it in her review, all of a sudden there was nothing to buy. She had her heart set on Ocean Hills Country Club, and we viewed home after home, but there simply was not much on the market. Eventually her buyer decided to move on.
That felt like a setback. It turned out to be a blessing in disguise.
We went back on the market, this time without a contingency — a bold step in a market that was demanding cash buyers, and one she took with us. The property sold immediately, to a buyer who offered well above asking and was incredibly flexible about when they would take possession. That flexibility became a free rent-back, which let our client remain in her own home until we found the right next one.
The Free Rent-Back: Why This Detail Mattered More Than the Price
It is worth pausing on that arrangement, because it is the part most sellers never think to ask for.
A rent-back lets you sell your home and then stay in it, as a tenant of the new owner, for an agreed period after closing. In this case our client paid nothing for that time. She had her sale proceeds in hand, which made her a strong non-contingent buyer, and she stayed in her own home — her own bed, her own kitchen, her own garage full of things still to sort — while we found the right next place.
Without it, the alternative was moving into a rental, putting everything into storage, and then moving again a few months later. Two moves, two sets of costs, and an enormous amount of effort at exactly the wrong moment.
The lesson for anyone selling before they buy: possession timing is negotiable, and it can be worth more to you than price. A buyer offering slightly less but willing to give you sixty free days may serve you far better than a higher offer demanding keys at closing. That only works if it is raised during offer negotiations rather than discovered afterward.
Rent-backs, extended escrows, and the other ways to bridge the gap between two homes are covered in where to live between homes: temporary housing options for San Diego downsizers.
Finding the Perfect Home
We didn’t have to wait long. Soon, we found a charming single-story home in the Shadowridge neighborhood of Vista that was just right for her. Our offer was accepted, and we promptly ordered a general home inspection. We had also negotiated for the seller to deliver the home termite-free with all damages repaired—repairs that ended up costing over $5,000.
Worth noting that she began this search set on Ocean Hills Country Club and ended up somewhere different. That happens often, and it is a good argument for looking broadly before deciding. The right home is sometimes in the community you had not considered.
Negotiating for the Future
The general home inspection revealed significant roof issues, prompting us to bring in a professional roofer for a more detailed assessment. The roofer confirmed that the entire roof was past its useful life and recommended a replacement costing $12,880. We successfully negotiated for the seller to credit our client $13,885 to cover the roof replacement.
Combined with the termite work, that is nearly $19,000 in repairs and credits negotiated on her behalf — on a home she had not yet moved into, while living rent-free in the home she had already sold.
A Happy Ending in Shadowridge
Our client is now happily settled in her Shadowridge cottage, her forever home. We were thrilled to have played a part in changing her mind about real estate professionals and helping her through this important transition in her life.
In Our Client’s Own Words
Our client left this verified 5-star review on RateMyAgent after the move:
“Jean and Ken are exceptional realtors to work with.”
“We started out with my agricultural piece of property with home to sell and I wanted it contingent upon my finding another home to move into. We sold it and the buyer was willing to give me time to find another home. We were also in the midst of Covid19 lockdown. All of a sudden there was nothing to buy. I very much wanted to live in Ocean Hills and Ken and Jean were very patient with me in viewing many homes. There just wasn’t that much available. The buyer decided to move on and I went back on the market. This time I sold the property with no contingency and it sold immediately. The market really demanded a cash buyer and Ken and Jean took the big step with me and we did it.
Ken was able to find me the cutest cottage in Shadow ridge with the prettiest back yard you’ve ever seen at a reasonable price that met my goal. Writing a few paragraphs does not really illustrate how much time and effort Ken and Jean put into my ‘effort’. There were two escrows to contend with, Ken is a really heartfelt negotiator and goes to bat for you. I recommend Ken and Jean and I would use them again.”
Seller and Buyer, Bonsall to Shadowridge, Vista
Verified review: read this verified review on RateMyAgent, where it is independently hosted and verified. You can also see all our RateMyAgent reviews, our Zillow profile, or more client reviews.
Common Questions About Selling Before You Buy
What is a free rent-back, and how do you get one?
A free rent-back is an arrangement where a seller stays in the home after closing without paying rent to the new owner. It is offered by buyers as a concession, most often when they want to win a competitive property or when their own timeline is flexible. It is not standard, and it is rarely volunteered — it has to be requested as part of offer negotiations. Sellers who ask for it early, while multiple offers are in play, are far more likely to get it than sellers who raise it after accepting.
Should I take the highest offer or the most flexible one?
It depends on what the flexibility is worth to you. If a shorter-dated offer means moving into a rental, storing your belongings, and moving a second time, the real cost of that convenience gap can exceed the difference in price — in money, and considerably more in effort. Compare the offers on total outcome rather than on the top-line number alone. A good agent should present them that way.
What happens if my buyer backs out before I have found my next home?
It is unsettling, but it is not the disaster it feels like in the moment. A buyer withdrawing means the home returns to the market, and in an active market a replacement buyer frequently arrives quickly. In this case the second buyer offered well above asking and was more flexible on possession than the first. The important thing is to stay in your home, keep your options open, and avoid making a rushed purchase to fill a gap that may not materialize.
Can I sell first and still avoid moving twice?
Often, yes. A rent-back is the most common way, letting you stay in your home after closing while you find and close on the next one. An extended escrow achieves something similar by delaying the closing date itself, so you remain the owner until you are ready. A rent-back after closing also makes you a non-contingent buyer, which strengthens your position when you do make an offer. Both have to be negotiated into the contract rather than arranged afterward.
Who pays for problems found during the home inspection?
It is negotiable, and it is where an experienced agent earns their fee. A general inspection may flag an issue in general terms; bringing in a specialist to quantify it converts a vague concern into a specific number you can negotiate against. In this purchase, a roof flagged as problematic became a roofer’s written assessment of $12,880, which became a seller credit of $13,885. The specialist’s report is what made the credit possible.
Thinking About a Move Like This One?
Leaving a large property for something smaller and single-story is one of the most common moves we handle in North County San Diego. Here is what we have written about it:
- Downsizing in San Diego: the complete guide — when to start, Proposition 19 property taxes, buy-first versus sell-first, Senior Move Managers, and which communities suit downsizers
- Where to live between homes — rent-backs, extended escrows, and what to do with your belongings
- Don’t move twice: buy first, then sell
- All our downsizing articles
- Free home valuation — no obligation, and no follow-up campaign
Warm Invitation to Start Your Home Journey
At DreamWell Homes Realty, we’re passionate about helping you find your perfect home and ensuring that your real estate experience is positive and rewarding. Whether you’re buying or selling, we’re here to guide you every step of the way. Let us help you create your own success story and find the home of your dreams.
We look forward to helping you find a place you’ll love to call home!
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