A Smart Exit Strategy for Long-Time Property Owners - A Case Study


We showed buyers a lot of homes this week from Encinitas to Point Loma and also launched a couple of exciting new listings. Don’t miss our picks and insights below.

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A Case Study

A local client owns several investment properties that have appreciated substantially over time. They have been strong rental properties for many years, but after reviewing the portfolio alongside the client’s financial team, it became clear that repositioning some of the equity outside of real estate could make sense for several reasons.

This is part of the big-picture planning we regularly discuss with our clients. We do far more with our lifelong clients than simply “buy” and “sell” homes. This particular scenario is actually quite common, so we wanted to share some of the thought process and analysis behind it.

Property Profile

The properties were built in 1969, so naturally they require ongoing maintenance. Every repair, capital improvement, or unexpected expense cuts into cash flow. The client has had the same property manager for years and has been very happy with the relationship.

The properties have provided stable, reliable income since the day they were purchased. Recently, however, one of the tenants gave notice, making it the perfect opportunity to evaluate whether it made more sense to rent the property again or consider selling.

Financial Analysis

The properties were purchased many years ago and therefore have a very low cost basis. With little to no mortgage remaining, the owner is no longer benefiting significantly from amortization or depreciation, which are two of the major financial advantages of owning investment real estate.

The properties were also originally purchased with a spouse who has since passed away. This is an important detail because of the stepped-up basis rule, which allows the cost basis to be adjusted to current market value at the date of death. This was the key factor in the analysis. In this case, the properties could potentially be sold with little to no capital gains tax exposure.

But does it actually make sense?

To answer that question, we calculated the cash yield, or net return on equity. Here is an example of how the numbers might look:

• $1 million net equity after commissions and closing costs
• Approximately $38,000 net annual rental income after property taxes, HOA fees, and management expenses
• Approximately $38,000 in annual income taxes owed on the rental income

That equates to roughly a 3.8% return on equity.

After consulting with both the CPA and financial advisor, the client recognized that capital gains exposure could potentially be minimal, while the proceeds could be repositioned into investments more aligned with current lifestyle goals and overall financial planning.

At the end of the day, it comes back to the math. In this case, the math made sense.

Additional benefits included improved liquidity, increased diversification, and potentially higher income with fewer management responsibilities. The owner no longer has to deal with tenants, insurance claims, HOA issues, or calls from the property manager about major capital expenses.

There are many strategies and benefits to acquiring real estate, but there can also be significant benefits to strategically planning an exit.

**Bonus: Even without a stepped-up basis, there are still excellent options available for long-time landlords looking for a way out of active property management. If you would like to discuss your situation or long-term plan, give us a call.

Olde Del Mar

386 13th Street

3 BD | 3 BA | 1,520 SF

$3,950,000

Ocean views, oversized corner lot, and a walk-to-everything address in Olde Del Mar. This classic beach bungalow sits on a fully usable 9,100+ sq ft corner lot with only one shared property line, delivering more yard, natural light, and a level of privacy rarely found this close to the beach.

Bird Rock | La Jolla

5383 Chelsea

2 BD | 2 BA | 1,868 SF

$1,998,000

Amazing Panoramic Ocean Views Enhanced with Sounds of the Ocean. Within 2 blocks from the Pacific Ocean! Conveniently close to Tourmaline Beach, Calumet Park, Bird Rock Award Winning Restaurants, Bakery, local Shopping, Wine, & Coffee Shops.

Country Club

7784 Lookout Drive

5 BD | 4 BA | 3,597 SF

$4,689,000

MOTIVATED Sellers! A premium opportunity in La Jolla Shores, this light-filled residence captures sweeping ocean views from multiple levels, with view-forward living spaces that open to generous terraces for effortless indoor-outdoor living and entertaining.

Solana Beach

353 Glenmont

3 BD | 3 BA | 3,927 SF

$4,750,000

FIRST TIME ON THE MARKET: Solana Beach artists Wayne & Barbara Chapman commissioned architect Kendrick Bangs Kellogg to reimagine their modest 1960s home and its surroundings. In a manner characteristic of Kellogg’s collaborations with his clients, the architect provided the vision while the clients took an active role in bringing it to life.

Kate Sessions

1726 Archer

3 BD | 2 BA | 1,708 SF

$1,999,000

This once-in-a-generation opportunity is not one to pass up. Custom-built in 1959 by a well-known local family and cherished by the same family ever since, this property is a rare time capsule of old Pacific Beach. What was simply stylish then is now celebrated as mid-century modern

Moonlight Beach | Encinitas

112 La Veta Avenue

4 BD | 4 BA | 3,427 SF

$30,000,000

Location is everything! Blocks from Moonlight Beach and historic downtown Encinitas, this is an exquisite property. The unique architectural details, exceptional amenities, and skillfully designed lot give it a tranquil, secluded feel.

4081 Morrell Street
Crown Point | Pacific Beach
$1,459,000

3 BED | 3 BATH | 1,698 SF

Experience timeless Tuscan-inspired design paired with the relaxed elegance of Pacific Beach living. From the tranquil courtyard waterfall entry to the panoramic rooftop views, every detail of this residence was thoughtfully curated for elevated coastal living.

15823 The River Trail
Rancho Santa Fe
Price Improvement! Now $4,975,000

5 BED | 4 BATH | 4,087 SF | 1.89 Acre Lot

An incredible opportunity to make this exquisite resort-style property in the esteemed River Estates neighborhood of Rancho Santa Fe yours!

147 S Rios Ave | Solana Beach

6 BED | 8 BATH | 5,143 SF

$9,050,000

Buyer Representation

Congrats to our clients on closing on their amazing new construction home right in the heart of Solana Beach. This home offers a lifestyle that is hard to beat.


The Ultimate Neighborhood Guide to La Jolla

Via Modern Luxury San Diego

With seven square miles of coastal beauty, La Jolla is one of San Diego’s most striking seaside cities. Whether you’re a local or just passing through, here is where to stay, savor and soak it all in.

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This report features an in-depth market analysis from Compass Chief Economist, Mike Simonsen, paired with national ultra-luxury sales data and firsthand insights from Compass real estate professionals nationwide. Together, these perspectives offer a clear picture of the ultra-luxury market in 2025, predictions for 2026, and market-specific insights shaping luxury real estate nationwide.

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Ryan Mathys & Tracie Kersten
Compass La Jolla
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Tracie@LaJollaAgent.com
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Compass is a real estate broker licensed by the State of California operating under multiple entities. License Numbers 01991628, 1527235, 1527365, 1356742, 1443761, 1997075, 1935359, 1961027, 1842987, 1869607, 1866771, 1527205, 1079009, 1272467. All material is intended for informational purposes only and is compiled from sources deemed reliable but is subject to errors, omissions, changes in price, condition, sale, or withdrawal without notice. No statement is made as to the accuracy of any description or measurements (including square footage). This is not intended to solicit property already listed. No financial or legal advice provided. Equal Housing Opportunity. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions.

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Ryan & Tracie

Whether you're buying, selling, or simply exploring the San Diego market, this is your go-to resource for strategic real estate guidance, tax-smart planning tips, and a curated look at the best homes across the county. As longtime local experts with decades of experience, we share real-world strategies we use with our clients every day, plus honest opinions on property values, neighborhood insights from true locals, and smart advice for those looking to invest in coastal San Diego.

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