8421 Whale Watch Way
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8421 Whale Watch Way

Dbottom 20%

La Jolla, CA 92037

$20,500,000
STR-eligible · San Diego Tier 3 · TOT 12.75%

One license per person in San Diego: whether you can hold it depends on you, not only the home.

54 licensed short-term rentals within ½ mile (45 whole home), from the cities' license and permit lists of Nov 11, 2026.

Pass at asking: -$142,720/mo full cashflow at 20% down, 7.43% rate.

Works at $1,917,720 (91% under asking); even all cash loses money at asking.

Rent $19,128/mo from 9 leases of 5–7 bed houses within 2 mi, same school area ($15,262–$30,910).

Beds

6

Baths

7.5

Sqft

8,218

Year Built

2026

Days on Market

141

Property Type

Single Family

HOA/mo

N/A

MLS ID

260013853SD

This property is in La Jolla (92037). View neighborhood stats →

Virtual Tour

About This Property

A VIEW SO VAST, YOU FEEL LIKE YOU OWN THE SKY. This just-completed contemporary residence captures the breathtaking scale of the sweeping view panorama through retracting floor-to-ceiling walls of glass. Located in upper La Jolla Shores, this elevated sanctuary offers a fabulous resort-style lifestyle. On one of the most highly-desired streets, Whale Watch Way. VERY, VERY, VERY EXCITING. The massive great room has soaring ceilings that establish a grand, voluminous feel. A beautiful kitchen, with double center islands, features an open-concept layout that flows into living areas, while the discrete prep kitchen keeps all pristine. The delectable primary suite has amazing space, a luxury bath, huge walk-in closet, and decking from which to indulge in view gazing day and night. There is a second Primary on the entry level, two multi-purpose family/rec rooms, fabulous outdoor spaces including expansive decking, patios, an outdoor cooking/entertaining area and an infinity-edge saltwater pool, 4-car garage plus a 2-car which is double-height. In close proximity to the beach and all of La Jolla Shores' pleasures.

Mortgage Calculator

Est. Monthly Payment

$140,365

Principal & Interest$113,886
Property Tax$20,500
Insurance$5,979
%($4,100,000)
%
Loan Term

Location

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Zoned Schools

  • Elementary

    Torrey Pines Elementary · grades K-5 · San Diego Unified

  • Middle

    Muirlands Middle · grades 6-8 · San Diego Unified

  • High

    La Jolla High · grades 9-12 · San Diego Unified

The district's assigned schools for this parcel, from its attendance boundaries and rules. Boundaries change: confirm with the district before you buy.

Investment Score

0D
Est. Monthly Rent
$19,128

9 leases of 5–7 bed houses within 2 mi, same school area · $15,262–$30,910

Monthly Cashflow

Rent − PITIA

-$121,237
Full Cashflow

Incl. vacancy, PM, maint, capex

-$142,720

What would make this work?

$142,720/mo short at 20% down; +$185,351/mo rent closes it.

Break-even price

91% under asking

$1,917,720
Break-even rent

$185,351/mo above the estimate

$204,479/mo
Cashflow at 35% down
−$121,366/mo
Down payment to break even

Negative even all-cash

Not reachable
Rate to break even

Negative even at a 0% loan

Not reachable

Mortgage (P+I)
$113,886
Cap Rate
-1.63%
Cash-on-Cash
-41.77%
DSCR

Need ≥ 1.25 for DSCR loan

0.14

NOI (Annual)
-$334,528
Price-to-Rent

Lower = better for investors

89.3

* Modelled at 20% down, 7.43% rate, 30yr · vacancy 8% · PM 10% · capex 5% · maintenance 1%/yr.

Estimates only. Not financial advice. Verify all figures independently with a licensed professional before making any investment decision.

Open Full Calculator
DCashflow−$142,720/mo